Synthesis and radical scavenging activity of 6-hydroxyl-4-methylcoumarin and its derivatives

NASA Astrophysics Data System (ADS)

Jumal, Juliana; Ayomide, Adetunji Fridaos

2018-06-01

Four compounds of coumarin derivatives namely 6-hydroxyl-4-methylcoumarin (I), 6-hydroxyl-4-methyl-5-(p-nitrophenyl azocoumarin) (II), 6-hydroxyl-4-methyl-5,7-(bis-p-nitrophenyl azocoumarin) (III) and 6-hydroxyl-4-methyl-5,7-(bis-p-chlorophenyl azocoumarin) (IV) were successfully synthesized. These compounds were prepared by reacting hydroquinone with ethylacetoacetate and selected anilines which are chloro and nitro aniline. All synthesized compounds were characterized by CHN micro-elemental analysis, 1H Nuclear Magnetic Resonance (NMR) and Fourier Transform Infrared (FTIR) spectroscopic methods. The infrared spectra of these compounds exhibited five important stretching vibrations: ʋ(-OH), ʋ(C=O), ʋ(C=C), ʋ(C-O) and ʋ(C-N) at 3441-3359 cm-1, 1604-1632 cm-1, 1581-1496 cm-1, 1331-1225 cm-1, 1251-1109 cm-1, respectively. 1H NMR spectra of these compounds show the presence of proton aromatic, proton methyl and proton pyrone ring with the chemical shift at δH 7.00-8.70 ppm, δH 2.20-2.50 ppm and δH 6.10-6.90 ppm, respectively. CHN analysis results of all compounds are in good agreement with the calculated values. All the synthesized compounds were evaluated for their antioxidant activity using DPPH method and ascorbic acid used as the standard. UV-Vis spectroscopic technique was used to investigate the absorbance of these compounds. Compound (II) shows high antioxidant activities compared to compound (I), (III) and (IV) which show moderate to low activities.

Two new compounds from Xanthium strumarium.

PubMed

Yin, Rong-Hua; Bai, Xue; Feng, Tao; Dong, Ze-Jun; Li, Zheng-Hui; Liu, Ji-Kai

2016-01-01

One new lignan, fructusol A (1), and one new thiazine derivative, 2-hydroxy-xanthiazone (2), along with eight known ones, were isolated from the seeds of Xanthium strumarium. The structures of new compounds were elucidated on the basis of extensive spectroscopic methods. Meanwhile, compounds 1-3 were tested for their antifungal activities against Candida albicans (ATCC 10231) in vitro. No one showed obvious inhibitions (MIC90 > 128 μg/ml).

Novel skeleton sesquiterpenoids isolated from guava leaves.

PubMed

Ouyang, Wen; Zhu, Xiao-ai; Wang, Wei; Chen, Xue-Xiang; Chen, Yun-Jiao; Cao, Yong

2016-01-01

A chemical investigation of the plant Psidium guajava L., collected in Guangdong province, afforded two novel skeleton sesquiterpenoids 1 and 2. Compound 2 also known as isocaryolan-9-one was a new natural product. The structure of the novel compound 1 was determined as guavacid A by various spectroscopic methods. A possible biosynthetic pathway for 1 and 2 was proposed.

Novel potato micro-tuber-inducing compound, (3R,6S)-6-hydroxylasiodiplodin, from a strain of Lasiodiplodia theobromae.

PubMed

Li, Peng; Takahashi, Kosaku; Matsuura, Hideyuki; Yoshihara, Teruhiko

2005-08-01

A novel potato micro-tuber-inducing compound was isolated from the culture broth of Lasiodiplodia theobromae Shimokita 2. The structure of the isolated compound was determined as (3R,6S)-6-hydroxylasiodiplodin by means of spectroscopic analyses, the modified Mosher method, and chemical conversion. The compound showed potato micro-tuber-inducing activity at a concentration of 10(-4) M, using the culture of single-node segments of potato stems in vitro.

New antioxidants from the culture broth of Hericium coralloides.

PubMed

Kim, Ji-Yul; Woo, E-Eum; Lee, In-Kyoung; Yun, Bong-Sik

2018-05-17

In our effort to find antioxidants from the higher fungi, we isolated three new compounds (1-3) with a known compound, spirobenzofuran (4), from the culture broth of Hericium coralloides. Bioassay-guided fractionation led to the isolation of these compounds, and we determined the chemical structures through spectroscopic methods. These compounds exhibited antioxidant activity in the range of IC 50 values of 29-66 μM in the 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical-scavenging assay.

Chemical constituents of the root of Jasminum giraldii.

PubMed

Yue, Zhenggang; Qin, Hui; Li, Yuhua; Sun, Yang; Wang, Zhipeng; Yang, Tiehong; Liu, Li; Wang, Minchang; Feng, Feng; Mei, Qibing

2013-04-22

Two new compounds, ethylconiferin and (-)-lariciresinol 4-(6'''-O-cinnamyl-β-D-glucopyranoside), along with the three known compounds (+)-pinoresinol, (+)-cycloolivil, nobiletin, were isolated from the root of Jasminum girialdii. All these compounds were isolated for the first time from this source. Their structures were elucidated on the basis of extensive spectroscopic analysis and chemical methods. In addition, the in vitro cytotoxic activity of these compounds was evaluated. The results showed that none of the compounds had any significant inhibitory activities on the proliferation of HCT-116 and SW-620 cells.

Water-soluble constituents of the root barks of Fraxinus rhynchophylla (Chinese drug Qinpi).

PubMed

Xiao, Kai; Song, Qing-Hong; Zhang, Shu-Wei; Xuan, Li-Jiang

2008-01-01

Chemical studies on the roots of Fraxinus rhynchophylla led to the isolation of fraxisecoside (1), a novel coumarin-secoiridoid hybrid glycoside, namely, fraxetin-8-O-[11'-methyl-oleosidyl-(7'-->6'')]-beta-D-glucopyranoside and 14 known compounds. Their structures were elucidated based on chemical evidence and spectroscopic analysis, including extensive 2D NMR methods. Compound 2 was first isolated as a pure compound. Compound 1 exhibited moderate PTP1B inhibition activity. Compounds 1 and 2 showed inhibition activity against B- and T-cell proliferation, without cytotoxicity.

Direct Identification of On-Bead Peptides Using Surface-Enhanced Raman Spectroscopic Barcoding System for High-Throughput Bioanalysis

PubMed Central

Kang, Homan; Jeong, Sinyoung; Koh, Yul; Geun Cha, Myeong; Yang, Jin-Kyoung; Kyeong, San; Kim, Jaehi; Kwak, Seon-Yeong; Chang, Hye-Jin; Lee, Hyunmi; Jeong, Cheolhwan; Kim, Jong-Ho; Jun, Bong-Hyun; Kim, Yong-Kweon; Hong Jeong, Dae; Lee, Yoon-Sik

2015-01-01

Recently, preparation and screening of compound libraries remain one of the most challenging tasks in drug discovery, biomarker detection, and biomolecular profiling processes. So far, several distinct encoding/decoding methods such as chemical encoding, graphical encoding, and optical encoding have been reported to identify those libraries. In this paper, a simple and efficient surface-enhanced Raman spectroscopic (SERS) barcoding method using highly sensitive SERS nanoparticles (SERS ID) is presented. The 44 kinds of SERS IDs were able to generate simple codes and could possibly generate more than one million kinds of codes by incorporating combinations of different SERS IDs. The barcoding method exhibited high stability and reliability under bioassay conditions. The SERS ID encoding based screening platform can identify the peptide ligand on the bead and also quantify its binding affinity for specific protein. We believe that our SERS barcoding technology is a promising method in the screening of one-bead-one-compound (OBOC) libraries for drug discovery. PMID:26017924

Direct identification of on-bead peptides using surface-enhanced Raman spectroscopic barcoding system for high-throughput bioanalysis.

PubMed

Kang, Homan; Jeong, Sinyoung; Koh, Yul; Geun Cha, Myeong; Yang, Jin-Kyoung; Kyeong, San; Kim, Jaehi; Kwak, Seon-Yeong; Chang, Hye-Jin; Lee, Hyunmi; Jeong, Cheolhwan; Kim, Jong-Ho; Jun, Bong-Hyun; Kim, Yong-Kweon; Hong Jeong, Dae; Lee, Yoon-Sik

2015-05-28

Recently, preparation and screening of compound libraries remain one of the most challenging tasks in drug discovery, biomarker detection, and biomolecular profiling processes. So far, several distinct encoding/decoding methods such as chemical encoding, graphical encoding, and optical encoding have been reported to identify those libraries. In this paper, a simple and efficient surface-enhanced Raman spectroscopic (SERS) barcoding method using highly sensitive SERS nanoparticles (SERS ID) is presented. The 44 kinds of SERS IDs were able to generate simple codes and could possibly generate more than one million kinds of codes by incorporating combinations of different SERS IDs. The barcoding method exhibited high stability and reliability under bioassay conditions. The SERS ID encoding based screening platform can identify the peptide ligand on the bead and also quantify its binding affinity for specific protein. We believe that our SERS barcoding technology is a promising method in the screening of one-bead-one-compound (OBOC) libraries for drug discovery.

A new hydroxychavicol dimer from the roots of Piper betle.

PubMed

Lin, Chwan-Fwu; Hwang, Tsong-Long; Chien, Chun-Chien; Tu, Huei-Yu; Lay, Horng-Liang

2013-02-26

A new hydroxychavicol dimer, 2-(g'-hydroxychavicol)-hydroxychavicol (1), was isolated from the roots of Piper betle Linn. along with five known compounds, hydroxychavicol (2), aristololactam A II (3), aristololactam B II (4), piperolactam A (5) and cepharadione A (6). The structures of these isolated compounds were elucidated by spectroscopic methods. Compounds 1 and 2 exhibited inhibitory effects on the generation of superoxide anion and the release of elastase by human neutrophils.

New pregnane glycosides from Gymnema sylvestre.

PubMed

Xu, Rui; Yang, Yu; Zhang, Yang; Ren, Fengxia; Xu, Jinlong; Yu, Nengjiang; Zhao, Yimin

2015-02-12

Four new pregnane glycosides 1-4 were isolated from the ethanol extract of the stem of Gymnema sylvestre and named gymsylvestrosides A-D. Hydrolysis of compound 1 under the catalysis of Aspergilus niger β-glucosidase afforded compound 5 (gymsylvestroside E). Their structures were determined by spectroscopic methods such as HRESIMS, 1D and 2D NMR, as well as HMQC-TOCSY experiment. Compounds 1-4 were screened for Saccharomyces cerevisiae α-glucosidase inhibitory activity.

Chemical constituents and biological activities from branches of Colubrina asiatica.

PubMed

Sangsopha, Watchara; Kanokmedhakul, Kwanjai; Lekphrom, Ratsami; Kanokmedhakul, Somdej

2018-05-01

Sixteen compounds were isolated from a Thai medicinal plant, Colubrina asiatica. The isolated compounds were elucidated on the basis of spectroscopic methods (IR, 1D and 2D NMR) as six triterpene acids (1-6), five steroids (7-11), one benzoic acid derivative (12), two peptides (13 and 14), one sesquiterpenoid (15) and one jujubogenin (16). Compounds 3 and 10 showed antimalarial activity against Plasmodium falciparum. Compound 5 showed antimycobacterial activity. Moreover, compounds 3, 5, 6, 10 and 14 exhibited weak cytotoxicity against cancer cell lines. Compounds 1-15 have been isolated for the first time from this plant.

Polyphenolic compounds with antioxidant potential and neuro-protective effect from Cimicifuga dahurica (Turcz.) Maxim.

PubMed

Qin, Rulan; Zhao, Ying; Zhao, Yudan; Zhou, Wanrong; Lv, Chongning; Lu, Jincai

2016-12-01

Three new phenolic compounds (1-3), along with five known compounds (4-8) were isolated from the rhizome of Cimicifuga dahurica (Turcz.) Maxim. Their structures were elucidated by spectroscopic methods including 1D-NMR, 2D-NMR and HR-MS techniques. DPPH method and protective effect on PC12 cells against H 2 O 2 -induced oxidative damage model were carried to evaluate the antioxidant capability of these compounds. Compound 5 showed significant antioxidant activity with IC 50 values 9.33μM in DPPH assay and compound 2 displayed marked neuro-protective effect with 87.65% cell viability at the concentration of 10μM. Additionally, the possible structure-activity relationships of these phenolic compounds were tentatively discussed. Copyright © 2016 Elsevier B.V. All rights reserved.

A new flavanolignan and a new alkane from the Stem bark of Newtonia griffoniana.

PubMed

Kinyok, Mc Jesus; Bonnet, Susan; Noté, Olivier Placide; Ngo Mbing, Joséphine; Kamto, Eutrophe Ledoux; Van der Westhuizen, Jan Hendrik; Pegnyemb, Dieudonné Emmanuel

2017-10-01

Two new compounds a flavanolignan (1), and an alkane (2) along with four known compounds including two fatty acid esters (3-4) and two isocoumarins (5-6) were isolated from the methanolic extract of the stem bark of Newtonia griffoniana. Their structures were elucidated using spectroscopic methods including extensive 1-D and 2-D NMR experiments.

Sesquiterpenoids and phenolics from roots of Taraxacum udum.

PubMed

Michalska, Klaudia; Marciniuk, Jolanta; Kisiel, Wanda

2010-07-01

From roots of Taraxacum udum, two new and four known sesquiterpene lactones were isolated, together with five known phenolic compounds. The new compounds were characterized as 11beta, 13-dihydrotaraxinic acid and taraxinic acid 6-O-acetyl-beta-glucopyranosyl ester by spectroscopic methods, especially 1D and 2D NMR, and by comparison with structurally related compounds. The plant material was shown to be a good source of taraxinic acid derivatives. Copyright 2009 Elsevier B.V. All rights reserved.

[Polyphenol compounds from Hamamelis virginiana L].

PubMed

Kostálová, D; Misíková, E; Gáborová, G

2001-01-01

Two phenolic acids and two flavone aglycones were isolated from the aboveground part of Hamamelis virginiana L. and identified with the use of thin-layer chromatography, melting points, and spectroscopic methods as gallic acid, ethyl gallate, quercetin, and kaempferol.

Computational and spectroscopic studies of a new Schiff base 3-hydroxy-4-methoxybenzylidene(2-hydroxyphenyl)amine and molecular structure of its corresponding zwitterionic form.

PubMed

Habibi, Mohammad Hossein; Shojaee, Elahe; Ranjbar, Mahnaz; Memarian, Hamid Reza; Kanayama, Akihiko; Suzuki, Takayoshi

2013-03-15

Computational and spectroscopic properties of a novel Schiff base compound, 3-hydroxy-4-methoxybenzylidene(2-hydroxyphenyl)amine were studied. The crystal structures of the title compound and its corresponding zwitterionic form were analyzed by X-ray diffraction. The presence of N-H, C-O and C=N stretching vibrations in IR spectrum strongly suggest that the title compound has zwitterionic form in the solid state. Molecular geometry of the title compound in the ground state has been calculated using the density functional method (DFT) at B3LYP 6-31++G(d,p) basis set and was compared with the experimental data. The calculated results of the title compound show that the optimized geometry can well reproduce the crystal structure. The molecule shows absorption bands at 345 and 363 nm in EtOH. The shoulder-shaped bands at 415 nm can be assigned to n→π(*) transitions. The absorption band is observed at 285 nm in EtOH corresponds to the π→π(*) transitions. Copyright © 2012 Elsevier B.V. All rights reserved.

The study of interaction between PFOA/PFOS and uracil by topology quality and spectroscopic analysis

NASA Astrophysics Data System (ADS)

Xu, Hui-Ying; Zhu, Jian-Qing; Wang, Wei; Xu, Xiao-Lu; Lu, Yin

2014-02-01

It has been established that perfluorooctanoic acid (PFOA) and perfluorooctane sulfonate (PFOS) can be considered as emerging persistent organic pollutants. In recent years, there was increasing distribution of PFOA/PFOS in environmental systems, and accumulation and toxic effects of PFOA/PFOS in human body. In this paper, quantum chemistry methods were employed to study the interaction between perfluorinated organic pollutants and base (uracil). The results showed that there were four stable binding modes between the two perfluorinated compounds with uracil, especially the second mode which caused the most detrimental physiological functional response. NBO analysis showed that reactive hydrogen in the two perfluorinated compounds had the greatest effect on the hydrogen bond. The nature of the hydrogen bond formed between the two perfluorinated compounds and base was investigated using the AIM theory. The changes of spectroscopic properties in complexes were analyzed by IR and NMR spectra.

Rapid, convenient method for screening imidazole-containing compounds for heme oxygenase inhibition.

PubMed

Vlahakis, Jason Z; Rahman, Mona N; Roman, Gheorghe; Jia, Zongchao; Nakatsu, Kanji; Szarek, Walter A

2011-01-01

Sensitive assays for measuring heme oxygenase activity have been based on the gas-chromatographic detection of carbon monoxide using elaborate, expensive equipment. The present study describes a rapid and convenient method for screening imidazole-containing candidates for inhibitory activity against heme oxygenase using a plate reader, based on the spectroscopic evaluation of heme degradation. A PowerWave XS plate reader was used to monitor the absorbance (as a function of time) of heme bound to purified truncated human heme oxygenase-1 (hHO-1) in the individual wells of a standard 96-well plate (with or without the addition of a test compound). The degradation of heme by heme oxygenase-1 was initiated using l-ascorbic acid, and the collected relevant absorbance data were analyzed by three different methods to calculate the percent control activity occurring in wells containing test compounds relative to that occurring in control wells with no test compound present. In the cases of wells containing inhibitory compounds, significant shifts in λ(max) from 404 to near 412 nm were observed as well as a decrease in the rate of heme degradation relative to that of the control. Each of the three methods of data processing (overall percent drop in absorbance over 1.5h, initial rate of reaction determined over the first 5 min, and estimated pseudo first-order reaction rate constant determined over 1.5h) gave similar and reproducible results for percent control activity. The fastest and easiest method of data analysis was determined to be that using initial rates, involving data acquisition for only 5 min once reactions have been initiated using l-ascorbic acid. The results of the study demonstrate that this simple assay based on the spectroscopic detection of heme represents a rapid, convenient method to determine the relative inhibitory activity of candidate compounds, and is useful in quickly screening a series or library of compounds for heme oxygenase inhibition. Copyright © 2010 Elsevier Inc. All rights reserved.

[Chemical constituents of Cocculus orbiculatus var. mollis root].

PubMed

Liao, Jing; Lei, Yu; Wang, Jian-Zhong

2014-02-01

To study the chemical constituents in the root of Cocculus orbiculatus var. mollis. The compounds were isolated by silica gel chromatography, their structures were established by spectroscopic methods. Eleven compounds were isolated and identified as wattisine A (I), O-methylcocsoline (II), (+) cocsoline (III), (+) cocsuline (IV), magnoflorine (V), sino-coculine (VI), isosinococuline (VII), (-) coclaurine (VIII), daucosterol (IX), beta-sitosterol (X) and 1-oleioyl-3-(9Z, 12Z-arachoyl) glycerol (XI). Compound I is isolated from this genus for the first time,and compound II - XI are isolated from this plant for the first time.

Metabolites from the endophytic fungus Penicillium sp. FJ-1 of Ceriops tagal.

PubMed

Jin, Peng-fei; Zuo, Wen-jian; Guo, Zhi-kai; Mei, Wen-li; Dai, Hao-fu

2013-11-01

To investigate the chemical constituents of the endophytic fungus Penicillium sp. FJ-1 of Ceriops tagal, the chemical constituents were isolated by column chromatography on silica gel and Sephadex LH-20. Their structures were elucidated on the basis of spectroscopic analysis. Their antibacterial activity was tested by paper disco diffusion method. Two compounds were isolated and identified as 7-hydroxy-deoxytalaroflavone (1), and deoxytalaroflavone (2). Compound 1 is a new compound, and compounds 1 and 2 showed weak activity against Staphylococcus aureus and methicillin-resistant Staphylococcus aureus.

A new Secondary metabolites of the crinoid (Comanthina schlegeli) associated fungus Alternaria brassicae 93.

PubMed

Zhang, Liu-Hong; Wang, Hong-Wei; Xu, Jia-Yi; Li, Jing; Liu, Lan

2016-10-01

Fungus Alternaria brassicae 93 isolated from crinoid (Comanthina schlegeli), which was collected from the South China Sea. Six compounds were isolated from A. brassicae 93, including one new compound (1), along with five known compounds, ochratoxin A methyl ester (2), cis-4-hydroxym-ellein (3), (R)-7-hydroxymellein (4), trans-2-anhydromevalonic (5) and protocatechuic acid (6). Their structures were determined by spectroscopic methods and comparison with reported data. Cytotoxicity against two human cancer cell lines and antibacterial activity against twelve aquatic bacteria of compound 1 were also tested.

Cyathane diterpenoids and nitrogenous terphenyl derivative from the fruiting bodies of basidiomycete Phellodon niger.

PubMed

Fang, Sheng-Tao; Zhang, Ling; Li, Zheng-Hui; Li, Bo; Liu, Ji-Kai

2010-09-01

Two new cyathane-type diterpenoids, nigernin A and B (1, 2), one new nitrogenous terphenyl derivative, phellodonin (3), together with three known compounds, 2',3'-diacetoxy-3,4,5',6',4''-pentahydroxy-p-terphenyl, grifolin, and 4-O-methylgrifolic acid, were isolated from the fruiting bodies of basidiomycete Phellodon niger. The structures of these new compounds were elucidated by spectroscopic methods and comparison with the data of known compounds in the literature. All these compounds were isolated from this fungus for the first time.

Phytochemical, cytotoxic and chemotaxonomic study on Ajuga forrestii Diels (Labiatae).

PubMed

Chen, Tong; Diao, Qing-Yan; Yu, Hai-Zhou; Jiao, Chun-Li; Ruan, Jian

2018-04-01

A phytochemical investigation of Ajuga forrestii Diels led to the isolation of 14 compounds, including eight neo-clerodane diterpenes (1-8), two phytoecdysteroids (9, 11), one stigmastane sterol (10) and three iridoid glycosides (12-14). The structures of these compounds were identified by spectroscopic methods and a comparison of their data with those reported in the literature. This is the first report of compounds 1-14 from A. forrestii. The cytotoxic activities of the aqueous extract of A. forrestii and several compounds have been studied and the chemotaxonomic significance of isolated compounds has also been summarised.

Two new compounds from an endophytic fungus Pestalotiopsis heterocornis.

PubMed

Xing, Jian-Guang; Deng, Hui-Ying; Luo, Du-Qiang

2011-12-01

Two new compounds, 7-hydroxy-5-methoxy-4,6-dimethyl-7-O-α-L-rhamnosyl-phthalide and 7-hydroxy-5-methoxy-4,6-dimethyl-7-O-β-D-glucopyranosyl-phthalide, along with one known and related metabolite 7-hydroxy-5-methoxy-4,6-dimethylphthalide were isolated from the EtOAc extract of fermentation broth of an endophytic fungus Pestalotiopsis heterocornis. The structures of these compounds were elucidated on the basis of spectroscopic methods (UV, IR, HR-ESI-MS, 1D NMR, and 2D NMR).

A new dihydrochalcone glycoside from the stems of Homalium stenophyllum.

PubMed

Wu, Shou-Yuan; Fu, Yan-Hui; Zhou, Qi; Bai, Meng; Chen, Guang-Ying; Han, Chang-Ri; Song, Xiao-Ping

2018-04-01

A new dihydrochalcone glycoside, phloretin-4-O-β-D-glucopyranoside (1), together with seven known flavonoids (2-8), were isolated from the stems of Homalium stenophyllum. The structure of 1 was elucidated by extensive spectroscopic methods and the known compounds were identified by comparisons with data reported in the literature. The known compounds (2-8) were isolated from the genus Homalium for the first time. All compounds were evaluated for their antibacterial activities against six pathogenic bacteria in vitro.

Two new compounds from the fruits of Arctium lappa.

PubMed

He, Jun; Huang, Xiao-Ying; Yang, Ya-Nan; Feng, Zi-Ming; Jiang, Jian-Shuang; Zhang, Pei-Cheng

2016-05-01

Phytochemical investigation of the extract of Arctii Fructus led to the isolation and characterization of two new compounds, named arctiisesquineolignan B (1) and arctiiphenolglycoside A (2). Their structures were elucidated by means of spectroscopic methods (UV, IR, HR-ESI-MS, 1D and 2D NMR) and chemical evidence, as well as by comparison with known analogs in the literature. Compound 2 exhibited stronger antioxidant activity than the positive control ascorbic acid at a concentration of 10 μM.

Multicomponent quantitative spectroscopic analysis without reference substances based on ICA modelling.

PubMed

Monakhova, Yulia B; Mushtakova, Svetlana P

2017-05-01

A fast and reliable spectroscopic method for multicomponent quantitative analysis of targeted compounds with overlapping signals in complex mixtures has been established. The innovative analytical approach is based on the preliminary chemometric extraction of qualitative and quantitative information from UV-vis and IR spectral profiles of a calibration system using independent component analysis (ICA). Using this quantitative model and ICA resolution results of spectral profiling of "unknown" model mixtures, the absolute analyte concentrations in multicomponent mixtures and authentic samples were then calculated without reference solutions. Good recoveries generally between 95% and 105% were obtained. The method can be applied to any spectroscopic data that obey the Beer-Lambert-Bouguer law. The proposed method was tested on analysis of vitamins and caffeine in energy drinks and aromatic hydrocarbons in motor fuel with 10% error. The results demonstrated that the proposed method is a promising tool for rapid simultaneous multicomponent analysis in the case of spectral overlap and the absence/inaccessibility of reference materials.

[Studies on chemical constituents of Illicium simonsii].

PubMed

Shang, Xiao-Ya; Guo, Miao-Ru; Zhao, Cong-Wei; Li, Shuai

2008-11-01

To study the chemical constituents from the active fractions against HIV in vitro, a crude ethanolic extract of Illicium simonsii. The compounds were isolated with column chromatography methods. MS and NMR spectroscopic methods were used to determine the structures of the compounds. Seven compounds were isolated from the active fractions against HIV in vitro of the 90% ethanol extract and their structures were elucidated as (+)-catechin (1), (-)-epicatechin (2), (+)-catechin 3-O-alpha-L-rhamnopyranoside (3), kaempferol 3-O-alpha-L-rhamnopyranoside (4), quercetin 3-O-alpha-L-rhamnopyranoside (5), erigeside C (6) and daucosterol (7). Seven compounds were isolated from this plant for the first time, but none of them exhibited active against HIV in vitro. Compounds 3 and 6 were isolated from this genus for the first time.

Two new phenolic constituents from the root bark of Morus alba L. and their cardioprotective activity.

PubMed

Cao, Yan-Gang; Zheng, Xiao-Ke; Yang, Fang-Fang; Li, Fang; Qi, Man; Zhang, Yan-Li; Zhao, Xuan; Kuang, Hai-Xue; Feng, Wei-Sheng

2018-02-01

A new biphenyl-furocoumarin, named morescoumarin A (1), and a new prenylated flavanone, named morflavanone A (2) were isolated from the root bark of Morus alba L., together with four known compounds (3-6). Their structures were determined by extensive spectroscopic analyses and comparison with literature data. The cardioprotective effects of these compounds against doxorubicin-induced cell death were evaluated by MTT method.

Bioactive metabolites from biotransformation of paeonol by the white-rot basidiomycete Coriolus versicolor.

PubMed

Li, Xiao-Jun; Shi, Xin-Wei; Shuai, Qi; Gao, Jin-Ming; Zhang, An-Ling

2011-08-01

Biotransformation of paeonol (1) with the white-rot basidiomycete Coriolus versicolor afforded two metabolites, 2,4-dihydroxyacetophenone (2) and 2,5-dihydroxy-4-methoxyacetophenone (3), which were identified by spectroscopic methods. Compound 3 showed higher antioxidative, antibacterial, antifungal activities than 1 or 2. The results demonstrate for the first time that C. versicolor has the capacities to catalyze hydroxylation and demethylation reactions on the aromatic compound.

Spectroscopic characteristic (FT-IR, FT-Raman, UV, 1H and 13C NMR), theoretical calculations and biological activity of alkali metal homovanillates

NASA Astrophysics Data System (ADS)

Samsonowicz, M.; Kowczyk-Sadowy, M.; Piekut, J.; Regulska, E.; Lewandowski, W.

2016-04-01

The structural and vibrational properties of lithium, sodium, potassium, rubidium and cesium homovanillates were investigated in this paper. Supplementary molecular spectroscopic methods such as: FT-IR, FT-Raman in the solid phase, UV and NMR were applied. The geometrical parameters and energies were obtained from density functional theory (DFT) B3LYP method with 6-311++G** basis set calculations. The geometry of the molecule was fully optimized, vibrational spectra were calculated and fundamental vibrations were assigned. Geometric and magnetic aromaticity indices, atomic charges, dipole moments, HOMO and LUMO energies were also calculated. The microbial activity of investigated compounds was tested against Bacillus subtilis (BS), Pseudomonas aeruginosa (PA), Escherichia coli (EC), Staphylococcus aureus (SA) and Candida albicans (CA). The relationship between the molecular structure of tested compounds and their antimicrobial activity was studied. The principal component analysis (PCA) was applied in order to attempt to distinguish the biological activities of these compounds according to selected band wavenumbers. Obtained data show that the FT-IR spectra can be a rapid and reliable analytical tool and a good source of information for the quantitative analysis of the relationship between the molecular structure of the compound and its biological activity.

[Study on Chemical Constituents from Roots of Lonicera macranthoides].

PubMed

Liu, Wen-juan; Chen, Yu; Ma, Xin; Zhao, You-yi; Feng, Xu

2014-12-01

To study chemical constituents of the roots of Lonicera macranthoides. The chemical constituents were isolated and purified by means of several chromatographic techniques and their structures were elucidated by spectroscopic methods. Seven compounds were isolated and identified as ribenol (1), excoecarin C (2), 18-hydroxy-13-epi-manoyloxide (3), asiatic acid (4), oleanolic acid (5), β-sitosterol (6) and β-daucosterol (7). Compounds 1-4 are obtained from this genus for the first time. Compound 5 is obtained from this plant for the first time. All the compounds are found from the roots of Lonicera mac- ranthoides for the first time.

[Study on the chemical constituents from Melicope ptelefolia].

PubMed

Xie, Yu-Feng; Liang, Yue; Du, Qing-Tao; Guo, Li-Bing

2011-03-01

To study the chemical constituents from Melicope ptelefolia. Several chromatographic methods were applied to isolate and purify compounds. Their structures were identified on the basis of physicochemical properties and spectroscopic data. Seven compounds were isolated and elucidated as n-octadecanyl palmitate (I), beta-sitosterol (II), palmitic acid (III), 3, 5,3'-trihydroxy-8,4'-dimethoxy-7-(3-methylbut-2-enyloxy) flavone (IV), daucosterol (V), salylic acid (VI), kaempferol-3-O-alpha-D-arabinpyranoside (VII). Compound VII is isolated from the genus for the first time, Compounds V and VI are isolated from Melicope ptelefolia for the first time.

Five new compounds from the fungus Ganoderma petchii.

PubMed

Dai, Wei-Feng; Guo, Ping-Xia; Tu, Zheng-Chao; Li, Rong-Tao; Cheng, Yong-Xian

2015-10-01

The fungal species of the genus Ganoderma attracted great interest in the last decades. Our recent investigation on Ganoderma petchii afforded five new compounds, (-)-petchioics A and B (1 and 2), petchiates A and B (3 and 4), petchine (5), and a known compound. The structures of the new compounds were elucidated on the basis of spectroscopic data. The absolute configurations of 1 and 2 were assigned by computational methods. Biological activities of these isolates towards human cancer cells, COX-1/2, and influenza virus were evaluated. Copyright © 2015 Elsevier B.V. All rights reserved.

Statin-like principles of bergamot fruit (Citrus bergamia): isolation of 3-hydroxymethylglutaryl flavonoid glycosides.

PubMed

Di Donna, Leonardo; De Luca, Giuseppina; Mazzotti, Fabio; Napoli, Anna; Salerno, Raffaele; Taverna, Domenico; Sindona, Giovanni

2009-07-01

The 3-hydroxy-3-methylglutaryl neohesperidosides of hesperetin (brutieridin, 1) and naringenin (melitidin, 2) were isolated and detected from the fruits of bergamot (Citrus bergamia). The structures of these compounds were determined by spectroscopic and chemical methods.

Choerosponins A and B, Two New Cytotoxic Bridged-Ring Ketones and the Determination of Their Absolute Configurations.

PubMed

Li, Chang-Wei; Han, Bing; Cai, Bing; Cui, Cheng-Bin

2017-03-27

Bioactivity-directed fractionation of antitumor compounds from the stem barks of Choerospondias axillaries (Roxb.) Burtt et Hill (Anacardiaceae) afforded two new cytotoxic bridged-ring ketones, choerosponins A ( 1 ) and B ( 2 ), and their structures were elucidated by spectroscopic methods; their stereochemistry was determined by NOE difference experiments, CD spectra and the modified Mosher's method. Compound 1 has a rare dioxatricyclo skeleton. Flow cytometry and SRB methods were employed to evaluate the antitumor activity of the two compounds against tsFT210, HCT-15, HeLa, A2780 and MCF-7 cell lines, and both of them showed strong cytotoxicity. MTT and paper disc methods were also used to evaluate their anti-hypoxia and antibacterial activities, and both of them showed no apparent activities.

Simple spectroscope used with solid state image amplifier over wide spectral range

NASA Technical Reports Server (NTRS)

Brown, R. L., Sr.

1971-01-01

Prism plus image amplifier panel provides visual image of many infrared spectral lines from carbon arc impregnated with metal compound. Different metal compounds generate various desired spectra. Panel also aligns and focuses simple spectroscopes for detecting spectral lines inside and outside visible region.

Hepatitis C virus inhibitory hydrolysable tannins from the fruits of Terminalia chebula.

PubMed

Ajala, Olusegun S; Jukov, Azzaya; Ma, Chao-Mei

2014-12-01

Two new hydrolysable tannins, chebumeinin A (1) and chebumeinin B (2), together with eight known related compounds (3-10), were isolated from the fruits of Terminalia chebula. The new compounds were structurally determined by analysis of their spectroscopic data and the known compounds characterized by comparing their spectroscopic data with literature values. All isolates were evaluated by an HCV protease inhibition assay, and some compounds were found to be potently active. Copyright © 2014 Elsevier B.V. All rights reserved.

Sesquiterpene-derived metabolites from the deep water marine sponge Poecillastra sollasi.

PubMed

Killday, K B; Longley, R; McCarthy, P J; Pomponi, S A; Wright, A E; Neale, R F; Sills, M A

1993-04-01

Six sesquiterpene-derived compounds, 1-6, which we call sollasins a-f, have been isolated from a deep water specimen of the sponge Poecillastra sollasi. The structures were elucidated by comparison of spectral data to related metabolites and confirmed using spectroscopic methods. The compounds inhibit the growth of the pathogenic fungi Candida albicans and Cryptococcus neoformans and the P-388 and A-549 tumor cell lines. Compounds 3 and 4 show weak inhibition of binding of [125I] angiotensin II to rat aorta smooth muscle cell membranes.

Cytotoxic deoxybenzoins and diphenylethylenes from Arundina graminifolia.

PubMed

Hu, Qiu-Fen; Zhou, Bin; Ye, Yan-Qing; Jiang, Zhi-Yong; Huang, Xiang-Zhong; Li, Yin-Ke; Du, Gang; Yang, Guang-Yu; Gao, Xue-Mei

2013-10-25

Eight new C-4-alkylated deoxybenzoins (1-8), three new diphenylethylenes (9-11), and five known diphenylethylenes were isolated from Arundina graminifolia. The structures of 1-11 were elucidated by spectroscopic methods including extensive 1D and 2D NMR techniques. Compounds 9-11 are the first naturally occurring diphenylethylenes possessing a hydroxyethyl unit. Compounds 1-11 were evaluated for cytotoxicity against five human tumor cell lines. Compounds 4, 5, and 9-11 showed significant cytotoxicity against five cancer cell lines, with IC50 values ranging from 1.8 to 8.7 μM.

Terpenoids and norlignans from Metasequoia glyptostroboides.

PubMed

Dong, Liao-Bin; He, Juan; Wang, Yuan-Yuan; Wu, Xing-De; Deng, Xu; Pan, Zheng-Hong; Xu, Gang; Peng, Li-Yan; Zhao, Yu; Li, Yan; Gong, Xun; Zhao, Qin-Shi

2011-02-25

Four new terpenoids, metaseglyptorin A (1), metasequoic acid C (2), 12α-hydroxy-8,15-isopimaradien-18-oic acid (3), and (-)-acora-2,4(14),8-trien-15-oic acid (4), and three new norlignans, metasequirins D-F (5-7), were isolated from Metasequoia glyptostroboides, together with 15 known compounds. Structures of the new compounds were determined by analysis of their spectroscopic data, and the absolute configuration of 7 was established by the modified Mosher method. All of the compounds were evaluated for cytotoxicity against five human tumor cell lines.

Application of Spectroscopic Methods for Structural Analysis of Chitin and Chitosan

PubMed Central

Kumirska, Jolanta; Czerwicka, Małgorzata; Kaczyński, Zbigniew; Bychowska, Anna; Brzozowski, Krzysztof; Thöming, Jorg; Stepnowski, Piotr

2010-01-01

Chitin, the second most important natural polymer in the world, and its N-deacetylated derivative chitosan, have been identified as versatile biopolymers for a broad range of applications in medicine, agriculture and the food industry. Two of the main reasons for this are firstly the unique chemical, physicochemical and biological properties of chitin and chitosan, and secondly the unlimited supply of raw materials for their production. These polymers exhibit widely differing physicochemical properties depending on the chitin source and the conditions of chitosan production. The presence of reactive functional groups as well as the polysaccharide nature of these biopolymers enables them to undergo diverse chemical modifications. A complete chemical and physicochemical characterization of chitin, chitosan and their derivatives is not possible without using spectroscopic techniques. This review focuses on the application of spectroscopic methods for the structural analysis of these compounds. PMID:20559489

Nuclear blebbing of biologically active organoselenium compound towards human cervical cancer cell (HeLa): in vitro DNA/HSA binding, cleavage and cell imaging studies.

PubMed

Rizvi, Masood Ahmad; Zaki, Mehvash; Afzal, Mohd; Mane, Manoj; Kumar, Manjeet; Shah, Bhahwal Ali; Srivastav, Saurabh; Srikrishna, Saripella; Peerzada, Ghulam Mustafa; Tabassum, Sartaj

2015-01-27

New pharmacophore organoselenium compound (1) was designed, synthesized and characterized by various spectroscopic methods (IR, ESI-MS, (1)H, (13)C and (77)Se NMR) and further confirmed by X-ray crystallography. Compound 1 consists of two 3,5-bis(trifluoromethyl)phenyl units which are connected to the selenium atom via the organometallic C-Se bond. In vitro DNA binding studies of 1 was investigated by absorption and emission titration methods which revealed that 1 recognizes the minor groove of DNA in accordance with molecular docking studies with the DNA duplex. Gel electrophoretic assay demonstrates the ability of 1 to cleave pBR322 DNA through hydrolytic process which was further validated by T4 religation assay. To understand the drug-protein interaction of which ultimate molecular target was DNA, the affinity of 1 towards HSA was also investigated by the spectroscopic and molecular modeling techniques which showed hydrophobic interaction in the subdomain IIA of HSA. Furthermore, the intracellular localization of 1 was evidenced by cell imaging studies using HeLa cells. Copyright © 2014 Elsevier Masson SAS. All rights reserved.

Phytoconstituents from Vitex agnus-castus fruits

PubMed Central

Chen, Shao-Nong; Friesen, J. Brent; Webster, Donna; Nikolic, Dejan; van Breemen, Richard B.; Wang, Z. Jim; Fong, Harry H.S.; Farnsworth, Norman R.; Pauli, Guido F.

2011-01-01

A new labdane-diterpene, viteagnusin I (1), together with 23 known phytoconstituents were isolated from the fruits of Vitex agnus-castus L, and their structures characterized by spectroscopic method (NMR and MS). The known compounds include ten flavonoids, five terpenoids, three neolignans, and four phenolic compounds, as well as one glyceride. Biological evaluation identified apigenin, 3-methylkaempferol, luteolin, and casticin as weak ligands of delta and mu opioid receptors, exhibiting dose-dependent receptor binding. PMID:21163339

Detection and Monitoring of Neurotransmitters - a Spectroscopic Analysis

NASA Astrophysics Data System (ADS)

Manciu, Felicia; Lee, Kendall; Durrer, William; Bennet, Kevin

2012-10-01

In this work we demonstrate the capability of confocal Raman mapping spectroscopy for simultaneously and locally detecting important compounds in neuroscience such as dopamine, serotonin, and adenosine. The Raman results show shifting of the characteristic vibrations of the compounds, observations consistent with previous spectroscopic studies. Although some vibrations are common in these neurotransmitters, Raman mapping was achieved by detecting non-overlapping characteristic spectral signatures of the compounds, as follows: for dopamine the vibration attributed to C-O stretching, for serotonin the indole ring stretching vibration, and for adenosine the adenine ring vibrations. Without damage, dyeing, or preferential sample preparation, confocal Raman mapping provided positive detection of each neurotransmitter, allowing association of the high-resolution spectra with specific micro-scale image regions. Such information is particularly important for complex, heterogeneous samples, where modification of the chemical or physical composition can influence the neurotransmission processes. We also report an estimated dopamine diffusion coefficient two orders of magnitude smaller than that calculated by the flow-injection method.

Ultrasonic promoted synthesis of novel s-triazine-Schiff base derivatives; molecular structure, spectroscopic studies and their preliminary anti-proliferative activities

NASA Astrophysics Data System (ADS)

El-Faham, Ayman; Soliman, Saied M.; Ghabbour, Hazem A.; Elnakady, Yasser A.; Mohaya, Talal A.; Siddiqui, Mohammed R. H.; Albericio, Fernando

2016-12-01

Novel series of s-triazine-Schiff base derivatives were synthesized employing ultrasonic irradiation and characterized by NMR (1H and 13C), FT-IR, and elemental analysis. The use of ultrasonic irradiation has allowed the preparation of the target products with better yields in shorter reaction time and excellent purities compared to the conventional heating. X-ray single crystal diffraction experiments verified the molecular structure of four from the new prepared s-triaizne-Schiff base derivatives. The molecular structures of the studied compounds are computerized using DFT/B3LYP method. The effects of substituent at the triazine and phenyl ring on the electronic and spectroscopic properties of the studied compounds were also investigated. The natural atomic charges showed that pipridino-s-triazine derivatives are richer in electrons than those having morpholino derivatives. The anti-proliferative effects for the prepared compounds were tested against three different cancer cell lines.

Three new alkaloids from the fruits of Morus alba.

PubMed

Wang, Xin; Kang, Jie; Wang, Hong-Qing; Liu, Chao; Li, Bao-Ming; Chen, Ruo-Yun

2014-01-01

From the fruits of Morus alba, three new alkaloids, mulbaines A (1), B (2), and C (3) were isolated. The structures of these compounds were elucidated on the basis of spectroscopic methods (UV, IR, HR-ESI-MS, 1D, and 2D NMR).

[Chemical constituents from stems of Ilex pubescens].

PubMed

Xing, Xian-dong; Zhang, Qian; Feng, Feng; Liu, Wen-yuan

2012-09-01

To study the chemical constituents from the stems of Ilex pubescens Hook. et Am. The chemical constituents were isolated and purified by various column chromatographic methods with diatomite, silica gel, ODS and Sephadex LH-20. Their structures were identified on physical properties and spectroscopic methods. Nine compounds were isolated and determined as luteolin(1), quercetin(2), hyperoside(3), rutin(4), 1, 5-dihydroxy-3-methyl-anthraquinone(5),3,5-dimethoxy-4-hydroxy-benzoic acid-1-O-beta-D-glucoside(6), hexadecanoic acid(7), stearic acid(8), n-tetratriacontanol(9), respectively. All the compounds are isolated from this plant for the first time, and compounds 5 and 6 are isolated from this genus for the first time.

Structural and spectroscopic characterization, reactivity study and charge transfer analysis of the newly synthetized 2-(6-hydroxy-1-benzofuran-3-yl) acetic acid

NASA Astrophysics Data System (ADS)

Murthy, P. Krishna; Krishnaswamy, G.; Armaković, Stevan; Armaković, Sanja J.; Suchetan, P. A.; Desai, Nivedita R.; Suneetha, V.; SreenivasaRao, R.; Bhargavi, G.; Aruna Kumar, D. B.

2018-06-01

The title compound 2-(6-hydroxy-1-benzofuran-3-yl) acetic acid (abbreviated as HBFAA) has been synthetized and characterized by FT-IR, FT-Raman and NMR spectroscopic techniques. Solid state crystal structure of HBFAA has been determined by single crystal X-ray diffraction technique. The crystal structure features O-H⋯O and C-H⋯O intermolecular interactions resulting in a two dimensional supramolecular architecture. The presence of various intermolecular interactions is well supported by the Hirshfeld surface analysis. The molecular properties of HBFAA were performed by Density functional theory (DFT) using B3LYP/6-311G++(d,p) method at ground state in gas phase, compile these results with experimental values and shows mutual agreement. The vibrational spectral analysis were carried out using FT-IR and FT-Raman spectroscopic techniques and assignment of each vibrational wavenumber made on the basis of potential energy distribution (PED). And also frontier orbital analysis (FMOs), global reactivity descriptors, non-linear optical properties (NLO) and natural bond orbital analysis (NBO) of HBFAA were computed with same method. Efforts were made in order to understand global and local reactivity properties of title compound by calculations of MEP, ALIE, BDE and Fukui function surfaces in gas phase, together with thermodynamic properties. Molecular dynamics simulation and radial distribution functions were also used in order to understand the influence of water to the stability of title compound. Charge transfer between molecules of HBFAA has been investigated thanks to the combination of MD simulations and DFT calculations.

Phytochemical Investigations on Chemical Constituents of Achillea tenuifolia Lam

PubMed Central

Moradkhani, Shirin; Kobarfard, Farzad; Ayatollahi, Seyed Abdol Majid

2014-01-01

Achillea tenuifolia Lam. (Asteraceae) afforded a methanolic extract from which after fractionation in solvents with different polarities, two known flavones 3’, 5- dihydroxy- 4’, 6, 7- trimethoxy flavone (eupatorine, compound 3), 5- hydroxy- 3’,4’, 6, 7- tetramethoxyflavone (compound 4), besides stearic acid (compound 1), lupeol (compound 2), daucosterol (β- sitosterol 3-O- β- D- glucopyranoside, compound 5), 2, 4- dihydroxy methyl benzoate (compound 6) were isolated for the first time. The structure of isolated compounds was elucidated by means of different spectroscopic methods such as UV, IR, Mass and 1H- NMR (1D and 2D) and 13C-NMR. For further confirming the structures of isolated compounds, comparison of the spectral data of them with those reported in the litratures have been done. PMID:25276207

New cytotoxic and anti-inflammatory compounds isolated from Morus alba L.

PubMed

Qin, Jing; Fan, Min; He, Juan; Wu, Xing-De; Peng, Li-Yan; Su, Jia; Cheng, Xiao; Li, Yan; Kong, Ling-Mei; Li, Rong-Tao; Zhao, Qin-Shi

2015-01-01

Six Diels-Alder adducts (1-6) and nine prenylated flavanones (7-15) were isolated from the root bark of Morus alba L. Among them, soroceal B (1) and sanggenol Q (7) were new compounds. Their structures were elucidated on the basis of extensive spectroscopic methods, including 1D and 2D NMR techniques. Compounds 1-3, 9, 10, 12, 13 and 15 exhibited cytotoxic activity against five human tumour lines and compound 2 inhibited significantly selective cytotoxic activities towards HL-60 and AGS cells with IC50 of 3.4 and 3.6 μM. Compounds 3, 5, 9 and 12 exhibited moderate inhibitory activity against nitric oxide production in LPS-activated RAW264.7.

Facile synthesis and antibacterial, antitubercular, and anticancer activities of novel 1,4-dihydropyridines.

PubMed

Sirisha, Kalam; Achaiah, Garlapati; Reddy, Vanga Malla

2010-06-01

A series of twenty new 4-substituted-2,6-dimethyl-3,5-bis-N-(heteroaryl)-carbamoyl-1,4-dihydropyridines have been prepared from a three-component one-pot condensation reaction of N-heteroaryl acetoacetamide, an aromatic/heteroaromatic aldehyde, and ammonium acetate under four different experimental conditions. Except for the conventional method, all the experimental conditions were simple, eco-friendly, economical, and the reactions were rapid and high-yielding. The methods employed have been compared in terms of yields, cost, and simplicity. The synthesized compounds were characterized by different spectroscopic techniques and evaluated for their in-vitro anticancer, antibacterial, and antitubercular activities. Amongst the compounds tested, compound 25 exhibited the highest anticancer activity while compounds 14 and 18 exhibited significant antibacterial and antitubercular activities.

Poecillastrin D: a new cytotoxin of the chondropsin class from marine sponge Jaspis serpentina.

PubMed

Takemoto, Daisaku; Takekawa, Yoshihiko; Soest, Rob W M van; Fusetani, Nobuhiro; Matsunaga, Shigeki

2007-11-01

Poecillastrin D (2) was isolated together with poecillastrin C (1) from the deep sea sponge, Japsis serpentina. Its structure was elucidated to be that of a macrolide lactam by spectroscopic methods. These compounds showed potent cytotoxicity against various tumor cell lines.

Synthesis, spectroscopic, crystal structure, biological activities and theoretical studies of 2-[(2E)-2-(2-chloro-6-fluorobenzylidene)hydrazinyl]pyridine

NASA Astrophysics Data System (ADS)

Dilek Özçelik, Nefise; Tunç, Tuncay; Çatak Çelik, Raziye; Erzengin, Mahmut; Özışık, Hacı

2017-05-01

We report in this paper the synthesis, spectroscopic, crystal structure, biological activities and theoretical results of the title compound. The crystal structure was defined by the X-ray diffraction (XRD) method. In addition, this newly synthesized hydrazone derivative was also subjected to its possible antioxidant activity with free radical scavenging ability of 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals using butylated hydroxytoluene (BHT) as standard antioxidant. The structural calculations were performed by the density functional theory using the B3LYP method with 6-311++G(2d,2p) basis set. The calculated values were compared with experimental results.

Synthesis, crystal structure investigation, spectroscopic characterizations and DFT computations on a novel 1-(2-chloro-4-phenylquinolin-3-yl)ethanone

NASA Astrophysics Data System (ADS)

Murugavel, S.; Stephen, C. S. Jacob Prasanna; Subashini, R.; Reddy, H. Raveendranatha; AnanthaKrishnan, Dhanabalan

2016-10-01

The title compound 1-(2-chloro-4-phenylquinolin-3-yl)ethanone (CPQE) was synthesised effectively by chlorination of 3-acetyl-4-phenylquinolin-2(1H)-one (APQ) using POCl3 reagent. Structural and vibrational spectroscopic studies were performed by utilizing single crystal X-ray diffraction, FTIR and NMR spectral analysis along with DFT method utilizing GAUSSIAN‧ 03 software. Veda program has been employed to perform a detailed interpretation of vibrational spectra. Mulliken population analyses on atomic charges, MEP, HOMO-LUMO, NBO, Global chemical reactivity descriptors and thermodynamic properties have been examined by (DFT/B3LYP) method with the 6-311G(d,p) basis set level.

Vitiquinolone--a quinolone alkaloid from Hibiscus vitifolius Linn.

PubMed

Ramasamy, D; Saraswathy, A

2014-02-15

Phytochemical investigations of the powdered root of Hibiscus vitifolius Linn. (Malvaceae) was extracted successively with n-hexane and chloroform. Analysis of the n-hexane extract by GC-MS led to the identification of twenty-six components by comparison of their mass spectra with GC-MS library data. A novel quinolone alkaloid, vitiquinolone (5) together with eight known compounds viz. β-Amyrin acetate (1), n-octacosanol (2), β-Amyrin (3), stigmasterol (4), xanthyletin (6), alloxanthoxyletin (7), xanthoxyletin (8) and betulinic acid (9) were isolated from chloroform extract by column chromatography over silica gel. The structure of vitiquinolone was established on the basis of spectroscopic methods including UV, IR, 1D, 2D NMR and ESI-MS. The known compounds were identified on the basis of their physical and spectroscopic data as reported in the literature. Copyright © 2013 Elsevier Ltd. All rights reserved.

Optical Sensing Properties of Pyrene-Schiff Bases toward Different Acids.

PubMed

Babgi, Bandar A; Alzahrani, Asma

2016-07-01

A set of (4-substituted-phenyl)-pyren-1-ylmethylene-amine (PMA) was prepared by the reaction of pyrene-1-carboxaldehyde and the corresponding 4-substituted aniline. The structure of the PMA compounds were confirmed by spectroscopic data (IR, (1)HNMR, (13)CNMR, ISI-MS and elemental analysis. The structure of (4-bromo-phenyl)-pyren-1-ylmethylene-amine (BrPMA) was further confirmed by the single X-ray crystallography. The absorption and emission spectroscopic behaviors were investigated in variant acids. The compounds showed dramatic spectroscopic changes upon acidifying with strong acids and negligible effects when weak acids are used in the acidifications. Hence, the PMA compounds can be used as sensors to distinguish between weak and strong acids.

Spectroscopic, electrochemical DNA binding and in vivo anti-inflammatory studies on newly synthesized Schiff bases of 4-aminophenazone.

PubMed

Arshad, Nasima; Ahmad, Mukhtar; Ashraf, Muhammad Zaman; Nadeem, Humaira

2014-09-05

4-Aminophenazone (Ap-1) Schiff bases i.e., 4-{(3,4,5-trimethoxybenzylidine) amino}phenazone (Ap-2), 4-{(2-chlorobenzylidine) amino}phenazone (Ap-3) and 4-{(4-chlorobenzylidine)amino} phenazone (Ap-4) were synthesized and characterized by different spectroscopic techniques. Interaction of these compounds with ds.DNA was investigated through UV-Visible spectroscopy, fluorescence spectroscopy and cyclic voltammetry at stomach (4.7) and blood (7.4) pH under 37 °C (human body temperature). Instrumental findings were further quantified both kinetically and thermodynamically. Results obtained through these techniques inferred intercalative mode of binding of all the compounds with DNA. The binding constant data, "Kb", and free energy change, ΔG, indicated comparatively greater binding affinity and more spontaneity of binding of compounds with DNA at stomach pH (4.7), respectively. However, among these compounds, Ap-4 showed comparatively greater binding at both the pH. Formation of compound-DNA complex was further confirmed through the decrease in diffusion rates after the addition of DNA. The in vivo anti-inflammatory activity of the compounds was evaluated using the carrageenan-induced hind paw edema method. The results revealed that among all the compounds, Ap-4 showed greater percentage of edema inhibition compared to standard drug. Copyright © 2014 Elsevier B.V. All rights reserved.

[Chemical constituents from supercritical CO2 extraction of Schisandra chinensis].

PubMed

Zhu, Hong-yan; Lin, Hai-cheng; Wang, Guo-li; Zhang, Lian-xue

2014-11-01

To study the chemical constituents from the supercritical CO2 extraction of Schisandra chinensis. The compounds were separated and purified by conventional column chromatography and their structures were identified by spectroscopic methods. Nine compounds were isolated from the supercritical CO2 extraction of Schisandra chinensis, and their structures were identified as chrysophanol(1),schisandrin B(2), β-sitosterol(3), schisandrin C(4),schisandrol A(5), angeloylgomisin H(6), daucosterol(7) 1, 5-dimethyl citrate (8), and shikimic acid (9). Compounds 1, 8 and 9 are isolated from Schisandra chinensis for the first time,and compound 1 as an anthraquinone is isolated from this genus for the first time.

Chemical constituents of the aerial part of Taraxacum mongolicum and their chemotaxonomic significance.

PubMed

Li, Wei; Lee, Changyeol; Kim, Young Ho; Ma, Jin Yeul; Shim, Sang Hee

2017-10-01

A phytochemical investigation of Taraxacum mongolicum led to the isolation of 24 compounds, including six flavonoids (1-6), four sesquiterpenes (7-10), two sphingolipids (11 and 12), six glycerols (13-18) and six triterpenoids and sterols (19-24). The structures of these compounds were identified by spectroscopic methods, and their data compared with those reported in the literature. This is the first report of compounds 11-19 from T. mongolicum and the genus Taraxacum, and compounds 11, 12, 15, 16, 18 and 19 from the Asteraceae family. The chemotaxonomic relationship between T. mongolicum and other Taraxacum species is also discussed.

Three new biflavonoids from the branches and leaves of Cephalotaxus oliveri and their antioxidant activity.

PubMed

Xiao, Shu; Mu, Zhen-Qiang; Cheng, Chun-Ru; Ding, Jie

2018-03-15

Three new biflavonoids, named oliveriflavones A-C (1-3), together with two known flavonoids (quercetin (4) and rutin (5)), were isolated from the endangered plant Cephalotaxus oliveri. The chemical structures of these compounds were elucidated by comprehensive spectroscopic methods including NMR, HRESIMS, IR, UV, and CD spectra. Compounds 1-5 were first isolated from the genus Cephalotaxus. All the compounds were tested for their antioxidant activity. Compounds 4 and 5 showed excellent activity with IC 50 values of 0.03 ± 0.06 μM and 0.02 ± 0.10 μM, respectively.

Aromatic hydrazones derived from nicotinic acid hydrazide as fluorimetric pH sensing molecules: Structural analysis by computational and spectroscopic methods in solid phase and in solution

NASA Astrophysics Data System (ADS)

Benković, T.; Kenđel, A.; Parlov-Vuković, J.; Kontrec, D.; Chiş, V.; Miljanić, S.; Galić, N.

2018-02-01

Structural analyses of aroylhydrazones were performed by computational and spectroscopic methods (solid state NMR, 1 and 2D NMR spectroscopy, FT-IR (ATR) spectroscopy, Raman spectroscopy, UV-Vis spectrometry and spectrofluorimetry) in solid state and in solution. The studied compounds were N‧-(2,3-dihydroxyphenylmethylidene)-3-pyridinecarbohydrazide (1), N‧-(2,5-dihydroxyphenylmethylidene)-3-pyridinecarbohydrazide (2), N‧-(3-chloro-2-hydroxy-phenylmethylidene)-3-pyridinecarbohydrazide (3), and N‧-(2-hydroxy-4-methoxyphenyl-methylidene)-3-pyridinecarbohydrazide (4). Both in solid state and in solution, all compounds were in ketoamine form (form I, sbnd COsbnd NHsbnd Ndbnd Csbnd), stabilized by intramolecular H-bond between hydroxyl proton and nitrogen atom of the Cdbnd N group. In solid state, the Cdbnd O group of 1-4 were involved in additional intermolecular H-bond between closely packed molecules. Among hydrazones studied, the chloro- and methoxy-derivatives have shown pH dependent and reversible fluorescence emission connected to deprotonation/protonation of salicylidene part of the molecules. All findings acquired by experimental methods (NMR, IR, Raman, and UV-Vis spectra) were in excellent agreement with those obtained by computational methods.

Pericocins A-D, New Bioactive Compounds from Periconia sp.

PubMed

Wu, Yue-Hua; Xiao, Gao-Keng; Chen, Guo-Dong; Wang, Chuan-Xi; Hu, Dan; Lian, Yun-Yang; Lin, Feng; Guo, Liang-Dong; Yao, Xin-Sheng; Gao, Hao

2015-12-01

One new dihydroisocoumarin, pericocin A (1), one new chromone, pericocin B (2), and two new α-pyrone derivatives, pericocins C-D (3-4), together with two known compounds, 3-(2-oxo-2H-pyran-6-yl)propanoic acid (5) and (E)-3-(2-oxo-2H-pyran-6-yl)acrylic acid (6), were isolated from the culture of the endolichenic fungus Periconia sp.. Their structures were elucidated by spectroscopic methods. All these compounds are derived from the polyketone biosynthetic pathway. Compound 1 was obtained as a mixture of enantiomers. The antimicrobial activity of compounds 1-5 was tested against Escherichia coli, Staphylococcus aureus, Aspergillus niger, and Candida albicans. Compounds 1-5 showed moderate antimicrobial activity against A. niger and weak activity against C. albicans.

[Studies on bioactive constituents of whole herbs of Vernonia cinerea].

PubMed

Zhu, Hua-xu; Tang, Yu-ping; Pan, Lin-mei; Min, Zhi-da

2008-08-01

To study the constituents of the whole herbs of Vernonia cinerea. by bio-activity guided isolation with PC-12 model. The constituents were separated by column chromatography and the structures were elucidated by spectroscopic methods. Four compounds were identified to be (+)-lirioresinol B (1), stigmasterol (2), stigmasterol-3-O-beta-D-glucoside (3), 4-sulfo-benzocyclobutene (4), and their NGF inducing activity were also investigated. Compounds 1, 3, 4 were isolated from this genus for the first time, and compound 4 was identified as a new natural product. Compounds 1, 3, 4 showed cytotoxicity on PC-12, and compounds 2, 3, 4 showed inhibition activity. Compound 4 showed a specific effect on the survival of TrkA fibroblasts, and resulted in the inducing NGF activity.

Spectroscopic analysis of 8-hydroxyquinoline derivatives and investigation of its reactive properties by DFT and molecular dynamics simulations

NASA Astrophysics Data System (ADS)

Sureshkumar, B.; Mary, Y. Sheena; Resmi, K. S.; Panicker, C. Yohannan; Armaković, Stevan; Armaković, Sanja J.; Van Alsenoy, C.; Narayana, B.; Suma, S.

2018-03-01

Two 8-hydroxyquinoline derivatives, 5,7-dichloro-8-hydroxyquinoline (57DC8HQ) and 5-chloro-7-iodo-8-hydroxy quinoline (5CL7I8HQ) have been investigated in details by means of spectroscopic characterization and computational molecular modelling techniques. FT-IR and FT-Raman experimental spectroscopic approaches have been utilized in order to obtain detailed spectroscopic signatures of title compounds, while DFT calculations have been used in order to visualize and assign vibrations. The computed values of dipole moment, polarizability and hyperpolarizability indicate that the title molecules exhibit NLO properties. The evaluated HOMO and LUMO energies demonstrate the chemical stability of the molecules. NBO analysis is made to study the stability of the molecules arising from hyperconjugative interactions and charge delocalization. DFT calculations have been also used jointly with MD simulations in order to investigate in details global and local reactivity properties of title compounds. Also, molecular docking has been also used in order to investigate affinity of title compounds against decarboxylase inhibitor and quinoline derivatives can be a lead compounds for developing new antiparkinsonian drug.

Sesquiterpenes from the east African sandalwood Osyris tenuifolia.

PubMed

Kreipl, Andreas Th; König, Wilfried A

2004-07-01

The essential oil of the east African sandalwood Osyris tenuifolia was investigated by chromatographic and spectroscopic methods. Beside several already known sesquiterpenes four new compounds could be isolated by preparative gas chromatography and their structures investigated by mass spectroscopy and NMR techniques. Two of the new compounds--tenuifolene (17) and ar-tenuifolene (15)--show a new sesquiterpene backbone. 2,(7Z,10Z)-Bisabolatrien-13-ol (23) and the cyclic ether lanceoloxide (21) belong to the bisabolanes.

Flavonoids from Ulex airensis and Ulex europaeus ssp. europaeus.

PubMed

Máximo, Patrícia; Lourenço, Ana; Feio, Sónia Savluchinske; Roseiro, José Carlos

2002-02-01

From the dichloromethane extract of Ulex airensis three new isoflavonoids, ulexin C (1), ulexin D (2), and 7-O-methylisolupalbigenin (3), were isolated and characterized by spectroscopic methods. Ulexin D (2) was also identified from the dichloromethane extract of Ulex europaeus ssp. europaeus. Together with these new metabolites, 18 compounds of previously known structures were isolated and identified from both species. The antifungal activity of these compounds was tested against Cladosporium cucumerinum by a bioautographic TLC assay.

A benzil and isoflavone derivatives from Derris scandens Benth.

PubMed

Mahabusarakam, W; Deachathai, S; Phongpaichit, S; Jansakul, C; Taylor, W C

2004-04-01

A benzil derivative: scandione, 2',2"-dihydroxy-4'-methoxy-4",5"-methylenedioxybenzil and two isoflavones: scandenal, 3'-formyl-4',5-dihydroxy-2",2"-dimethylchromeno-[6,7:5",6"]isoflavone and scanderone, 4',5-dihydroxy-3'-prenyl-2",2"-dimethylchromeno-[7,8:6",5"]isoflavone together with fifteen known compounds were isolated from the stem of D. scandens. Their structures were determined by spectroscopic methods. Radical scavenging, antibacterial and hypertensive activities of some of the compounds were investigated.

Ten new withanolides from Physalis peruviana.

PubMed

Fang, Sheng-Tao; Liu, Ji-Kai; Li, Bo

2012-01-01

Ten new withanolides, including four perulactone-type withanolides, perulactones E-H (1-4), three 28-hydroxy-withanolides, withaperuvins I-K (5-7), and three other withanolides, withaperuvins L-N (8-10), together with six known compounds (11-16) were isolated from the aerial parts of Physalis peruviana. The structures of these compounds were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, IR, HR-MS) and chemical methods. Copyright © 2011 Elsevier Inc. All rights reserved.

Four new spiroaxane sesquiterpenes and one new rosenonolactone derivative from cultures of Basidiomycete Trametes versicolor.

PubMed

Wang, Su-Rui; Zhang, Ling; Chen, He-Ping; Li, Zheng-Hui; Dong, Ze-Jun; Wei, Kun; Liu, Ji-Kai

2015-09-01

Four new spiroaxane sesquiterpenes, tramspiroins A-D (1-4), one new rosenonolactone 15,16-acetonide (5), and the known drimane sesquiterpenes isodrimenediol (6) and funatrol D (7) have been isolated from the cultures of Basidiomycete Trametes versicolor. The structures of new compounds were elucidated by means of spectroscopic methods. Compounds 1-7 were investigated for their cytotoxicities against five human cancer cell lines. Copyright © 2015 Elsevier B.V. All rights reserved.

Application of correlation constrained multivariate curve resolution alternating least-squares methods for determination of compounds of interest in biodiesel blends using NIR and UV-visible spectroscopic data.

PubMed

de Oliveira, Rodrigo Rocha; de Lima, Kássio Michell Gomes; Tauler, Romà; de Juan, Anna

2014-07-01

This study describes two applications of a variant of the multivariate curve resolution alternating least squares (MCR-ALS) method with a correlation constraint. The first application describes the use of MCR-ALS for the determination of biodiesel concentrations in biodiesel blends using near infrared (NIR) spectroscopic data. In the second application, the proposed method allowed the determination of the synthetic antioxidant N,N'-Di-sec-butyl-p-phenylenediamine (PDA) present in biodiesel mixtures from different vegetable sources using UV-visible spectroscopy. Well established multivariate regression algorithm, partial least squares (PLS), were calculated for comparison of the quantification performance in the models developed in both applications. The correlation constraint has been adapted to handle the presence of batch-to-batch matrix effects due to ageing effects, which might occur when different groups of samples were used to build a calibration model in the first application. Different data set configurations and diverse modes of application of the correlation constraint are explored and guidelines are given to cope with different type of analytical problems, such as the correction of matrix effects among biodiesel samples, where MCR-ALS outperformed PLS reducing the relative error of prediction RE (%) from 9.82% to 4.85% in the first application, or the determination of minor compound with overlapped weak spectroscopic signals, where MCR-ALS gave higher (RE (%)=3.16%) for prediction of PDA compared to PLS (RE (%)=1.99%), but with the advantage of recovering the related pure spectral profile of analytes and interferences. The obtained results show the potential of the MCR-ALS method with correlation constraint to be adapted to diverse data set configurations and analytical problems related to the determination of biodiesel mixtures and added compounds therein. Copyright © 2014 Elsevier B.V. All rights reserved.

Dracophane, a metacyclophane derivative from the resin of Dracaena cinnabari Balf.

PubMed

Veselá, Dagmar; Marek, Radek; Ubik, Karel; Lunerová, Kamila; Sklenár, Vladimír; Suchý, Václav

2002-12-01

Dracophane, a novel structural derivative of metacyclophane, was isolated from the resin of Dracaena cinnabari Balf. The structure of this compound was determined by spectroscopic methods to be 3,12,21-trihydroxy-1,10,19-tris(4-hydroxyphenyl)-5,14,23-trimethoxy[3.3.3]metacyclophane.

[Chemical constituents of the roots of Vaccinium bracteatum].

PubMed

Lv, Xiao-Lan; Mai, Xi; Guo, Hui; Lai, Xiao-Ping

2012-06-01

To study the chemical constituents of the roots of Vaccinium bracteatum. The constituents were separated and purified with chromatographic methods (including silica gel, Sephadex LH-20 and RP-18 column chromatography), and their structures were determined by spectroscopic methods (including MS, 1H-NMR and 13C-NMR). 10 compounds were isolated from the roots of Vaccinium bracteatu and were elucidated as chlorogenic acid (1), pinoresinol (2), ferulic acid (3), kaempferol (4), trans-caffeic acid (5), beta-sitosterol (6), quercetin (7), oleanolic acid (8), apigenin (9) and luteolin (10). Compounds 1 -3 are obtained from this plant for the first time.

Chiral lactic hydrazone derivatives as potential bioactive antibacterial agents: Synthesis, spectroscopic, structural and molecular docking studies

NASA Astrophysics Data System (ADS)

Noshiranzadeh, Nader; Heidari, Azam; Haghi, Fakhri; Bikas, Rahman; Lis, Tadeusz

2017-01-01

A series of novel chiral lactic-hydrazone derivatives were synthesized by condensation of (S)-lactic acid hydrazide with salicylaldehyde derivatives and characterized by elemental analysis and spectroscopic studies (FT-IR, 1H NMR and 13C NMR spectroscopy). The structure of one compound was determined by single crystal X-ray analysis. Antibacterial activity of the synthesized compounds was studied against Staphylococcus aureus, Streptococcus pneumonia, Escherichia coli and Pseudomonas aeruginosa as bacterial cultures by broth microdilution method. All of the synthesized compounds showed good antibacterial activity with MIC range of 64-512 μg/mL. Compounds (S,E)-2-hydroxy-N-(2-hydroxy-5-nitrobenzylidene)propanehydrazide (5) and (S,E)-2-hydroxy-N-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)propanehydrazide (7) were the most effective antibacterial derivatives against S. aureus and E. coli respectively with a MIC value of 64 μg/mL. Bacterial biofilm formation assay showed that these compounds significantly inhibited biofilm formation of P. aeruginosa. Also, in silico molecular docking studies were performed to show lipoteichoic acid synthase (LtaS) inhibitory effect of lactic hydrazone derivatives. The association between electronic and structural effects of some substituents on the benzylidene moiety and the biological activity of these chiral compounds were studied. Structural studies show that compound with higher hydrogen bonding interactions show higher antibacterial activity. The results show chiral hydrazone derivatives based on lactic acid hydrazide could be used as potential lead compounds for developing novel antibacterial agents.

Spectroscopic investigation, hirshfeld surface analysis and molecular docking studies on anti-viral drug entecavir

NASA Astrophysics Data System (ADS)

Fathima Rizwana, B.; Prasana, Johanan Christian; Abraham, Christina Susan; Muthu, S.

2018-07-01

Entecavir, a new deoxyguanine nucleoside analogue, is a selective inhibitor of the replication of the hepatitis B virus. In the present study, Quantum mechanical approach was carried out on the title compound to study the vibrational spectrum, the stability of the compound, the intermolecular and intramolecular interactions by using Density Functional Theory (DFT) with B3LYP 6-311++G(d,p) basis set. The B3LYP/DFT method was chosen because diverse studies have shown that the results obtained with it are in good agreement with those determined by other costly computational methods. The computational methods were aided by the experimental spectroscopic techniques, namely FTIR and FT Raman spectroscopies. The optimized molecular geometry, vibrational wavenumbers, infrared intensities and Raman scattering activities were calculated. The calculated HOMO and LUMO energies were found to be -6.397 eV and -1.504 eV which indicate the charge transfer within the molecule. The maximum absorption wavelength and the band gap energy of the title compound were obtained from the UV absorption spectrum computed theoretically. Natural Bond Orbital analysis has been carried out to explain the charge transfer (or) delocalization of charge due to the intra molecular interactions. The molecule orbital contributions are studied by using the total (TDOS), partial (PDOS), and overlap population (OPDOS) density of states. Molecular electrostatic potential (MEP), First order hyperpolarizability, Hirshfield surface analysis and Fukui functions calculation were also performed. From the calculations the first order hyperpolarizability was found to be 2.3854 × 10-30 esu. The thermodynamic properties (heat capacity, entropy, and enthalpy) of the title compound at different temperatures have been calculated. Molecular docking studies were made on the title compound to study the hydrogen bond interactions and the minimum binding energy was calculated.

Exploring the structural basis of the selective inhibition of monoamine oxidase A by dicarbonitrile aminoheterocycles: role of Asn181 and Ile335 validated by spectroscopic and computational studies.

PubMed

Juárez-Jiménez, Jordi; Mendes, Eduarda; Galdeano, Carles; Martins, Carla; Silva, Daniel B; Marco-Contelles, José; do Carmo Carreiras, Maria; Luque, F Javier; Ramsay, Rona R

2014-02-01

Since cyanide potentiates the inhibitory activity of several monoamine oxidase (MAO) inhibitors, a series of carbonitrile-containing aminoheterocycles was examined to explore the role of nitriles in determining the inhibitory activity against MAO. Dicarbonitrile aminofurans were found to be potent, selective inhibitors against MAO A. The origin of the MAO A selectivity was identified by combining spectroscopic and computational methods. Spectroscopic changes induced in MAO A by mono- and dicarbonitrile inhibitors were different, providing experimental evidence for distinct binding modes to the enzyme. Similar differences were also found between the binding of dicarbonitrile compounds to MAO A and to MAO B. Stabilization of the flavin anionic semiquinone by monocarbonitrile compounds, but destabilization by dicarbonitriles, provided further support to the distinct binding modes of these compounds and their interaction with the flavin ring. Molecular modeling studies supported the role played by the nitrile and amino groups in anchoring the inhibitor to the binding cavity. In particular, the results highlight the role of Asn181 and Ile335 in assisting the interaction of the nitrile-containing aminofuran ring. The network of interactions afforded by the specific attachment of these functional groups provides useful guidelines for the design of selective, reversible MAO A inhibitors. Copyright © 2013 Elsevier B.V. All rights reserved.

Chemical components of the roots of Noni (Morinda citrifolia) and their cytotoxic effects.

PubMed

Lv, Lishuang; Chen, Huadong; Ho, Chi-Tang; Sang, Shengmin

2011-06-01

Roots of Morinda citrifolia (Noni or Yor in Thai) have been used traditionally for thousands of years to treat chronic diseases such as cancer and heart disease. In this study, three new anthraquinones together with 15 known compounds were isolated from the roots of M. citrifolia (Rubiaceae). Their structures were established by spectroscopic methods, particularly 1D and 2D NMR techniques. Six known compounds, together with two new compounds (2 and 3) showed significant inhibitory effects on the proliferation of human lung and colon cancer cells. Copyright © 2011 Elsevier B.V. All rights reserved.

(-)-Xanthienopyran, a new inhibitor of superoxide anion generation by activated neutrophils, and further constituents of the seeds of Xanthium strumarium.

PubMed

Lee, Chia-Lin; Huang, Po-Ching; Hsieh, Pei-Wen; Hwang, Tsong-Long; Hou, Yu-Yi; Chang, Fang-Rong; Wu, Yang-Chang

2008-08-01

The dried seeds of XANTHIUM STRUMARIUM (Asteraceae) are used after thorough stir-frying as an ingredient in traditional Chinese medicines for relieving allergy. Two new compounds, xanthialdehyde ( 2) and (-)-xanthienopyran ( 7), as well as 26 known compounds were isolated in the present study. The structures of the isolates were elucidated by spectroscopic methods. Among them, compound 7 exhibited significant selective inhibition of superoxide anion generation by human neutrophils induced by formyl- L-methionyl- L-leucyl- L-phenylalanine, with an IC50 value of 1.72 microg/mL.

Plant growth activities of aspyran, asperentin, and its analogues produced by the fungus Aspergillus sp.

PubMed

Kimura, Yasuo; Shimomura, Naomi; Tanigawa, Fumiaki; Fujioka, Shozo; Shimada, Atsumi

2012-01-01

Aspyran (1), a novel compound, and the known isocoumarin asperentin (2), also known as cladosporin, together with its analogues 3-6 were isolated from Aspergillus sp. and their structures established by spectroscopic methods including 2D NMR spectroscopy. The effects of 1-6 on plant growth were examined by bioassays using lettuce and rice seedlings. Compounds 1 and 3 promoted the root growth of the seedlings, while 2 and 5 were inhibitory. Compounds 4 and 6 did not show any effect on the growth of lettuce and rice seedlings, respectively.

[Chalcones from Bauhinia glauca subsp. pernervosa].

PubMed

Wu, Zengbao; Wang, Bin; Zhao, Yuying; Yang, Xiuwei; Liang, Hong

2009-07-01

To study the chemical constituents of Bauhinia glauca subsp. pernervosa. The coulis of B. glauca subsp. pernervosa were extracted with 95% EtOH at room temperature. The compounds were isolated and separated by chromatographic techniques, and structures were identified by spectroscopic methods. Seven chalcones were isolated and identified: butein-4-methyl ether (1), isoliquiritigenin (2), butein (3), isoliquiritigenin-2'-methyl ether (4), 2',4'-dihydroxychalcone (5), isoliquiritigenin-4-methyl ether (6), 4-hydroxy-2',4'-dimethoxychalcone (7). Compounds 1, 3, and 7 were isolated from the genus Bauhinia for the first time, the other compounds were obtained from this plant for the first time.

Triterpenes and saponins from Rudgea viburnioides.

PubMed

Young, M C; Araújo, A R; da Silva, C A; Lopes, M N; Trevisan, L M; Bolzani, V S

1998-07-01

A novel triterpene, viburgenin (1), has been isolated from an extract of the ripe fruit rinds of Rudgea viburnioides, together with the known saponins, arjunglucoside I and trachelosperosides B-1 and E-1, and the triterpenes trachelosperogenin B (2) and arjungenin. Compound 2 was previously obtained as a product from enzymatic hydrolysis, and it is reported for the first time as a natural product. The structure of compound 1 was determined as 2alpha,3beta, 19alpha,23,24-pentahydroxyurs-12-ene by extensive use of 1D and 2D NMR spectroscopic methods. Compound 1 exhibited moderate antifungal activity against Cladosporium cladosporioides.

[Non-alkaloid components from Sophora flavescens].

PubMed

Zhang, Chi; Ma, Yue; Gao, Hui-Min; Liu, Xiao-Qian; Chen, Liang-Mian; Zhang, Qi-Wei; Wang, Zhi-Min; Li, An-Ping

2013-10-01

Five compounds were obtained from the stems and leaves of Sophora flavescens Ait. and ten compounds were obtained from the roots of S. flavescens by various chromatography methods including silica gel column chromatography and preparative HPLC. Their structures were identified on the basis of spectroscopic methods including 1H-NMR, 13C-NMR and ESI-MS, as corchionoside C (1), syringing (2), 2'-deoxythymidin (3), coniferin (4), benzyl O-beta-D-glucopyranoside (5), piscidic acid (6), trifolirhizin (7), kurarinone (8), trifolirhizin-6'-monoacetate (9), sophoraflavanone G (10), isoxanthohumol (11), noranhydroicaritin (12), 4'-methoxyisoflavone-7-O-beta-D-apiofuranosyl-(1 --> 6)-beta-D-glucopyranoside (13), kushenol O (14) and 6"-beta-D-xylopyranosylgenistin (15). Compounds 1-6 were isolated from the Sophora genus for the first time.

The spectroscopic properties of anticancer drug Apigenin investigated by using DFT calculations, FT-IR, FT-Raman and NMR analysis

NASA Astrophysics Data System (ADS)

Mariappan, G.; Sundaraganesan, N.; Manoharan, S.

2012-09-01

The FT-Raman and FT-Infrared spectra of solid Apigenin sample were measured in order to elucidate the spectroscopic properties of title molecule in the spectral range of 3500-50 cm-1 and 4000-400 cm-1, respectively. The recorded FT-IR and FT-Raman spectral measurements favor the calculated (by B3LYP/6-31G(d,p) method) structural parameters which are further supported by spectral simulation. Additional support is given by the collected 1H and 13C NMR spectra recorded with the sample dissolved in DMSO. The predicted chemical shifts at the B3LYP/6-31G(d) level obtained using the Gauge-Invariant Atomic Orbitals (GIAO) method with and without inclusion of solvent using the Polarizable Continuum Model (PCM). By using TD-DFT method, electronic absorption spectra of the title compound have been predicted and a good agreement with the TD-DFT method and the experimental one is determined. The UV-visible absorption spectra of the compound that dissolved in Ethanol, Methanol and DMSO were recorded in the range of 800-200 nm. The formation of hydrogen bond and the most possible interaction are explained using natural bond orbital (NBO) analysis. In addition, the molecular electrostatic potential (MEP), frontier molecular orbitals (FMO) analysis and atomic charges of the title compound were investigated using theoretical calculations. The results are discussed herein and compared with similar molecules whenever appropriate.

Synthesis, Structural and Antioxidant Studies of Some Novel N-Ethyl Phthalimide Esters

PubMed Central

Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun

2015-01-01

A series of N-ethyl phthalimide esters 4(a-n) were synthesized and characterized by spectroscopic studies. Further, the molecular structure of majority of compounds were analysed by single crystal X-ray diffraction studies. The X-ray analysis revealed the importance of substituents on the crystal stability and molecular packing. All the synthesized compounds were tested for in vitro antioxidant activity by DPPH radical scavenging, FRAP and CUPRAC methods. Few of them have shown good antioxidant activity. PMID:25742494

Phytoconstituents from Vitex agnus-castus fruits.

PubMed

Chen, Shao-Nong; Friesen, J Brent; Webster, Donna; Nikolic, Dejan; van Breemen, Richard B; Wang, Z Jim; Fong, Harry H S; Farnsworth, Norman R; Pauli, Guido F

2011-06-01

A new labdane-diterpene, viteagnusin I (1), together with 23 known phytoconstituents were isolated from the fruits of Vitex agnus-castus L, and their structures characterized by spectroscopic methods (NMR and MS). The known compounds include ten flavonoids, five terpenoids, three neolignans, and four phenolic compounds, as well as one glyceride. Biological evaluation identified apigenin, 3-methylkaempferol, luteolin, and casticin as weak ligands of delta and mu opioid receptors, exhibiting dose-dependent receptor binding. Copyright © 2011 Elsevier B.V. All rights reserved.

Five New Guanacastane-Type Diterpenes from Cultures of the Fungus Psathyrella candolleana.

PubMed

Yin, Xia; Feng, Tao; Li, Zheng-Hui; Leng, Ying; Liu, Ji-Kai

2014-06-01

Five new guanacastane-type diterpenes, named guanacastepenes P-T (1-5), were isolated from cultures of the fungus Psathyrella candolleana. Their structures were elucidated on the basis of extensive spectroscopic methods. All of the compounds were tested for their 11β-hydroxysteroid dehydrogenase (11β-HSD1) inhibitory activity. Compound 3 exhibited inhibitory activity against both human and mouse isozymes of 11β-HSD1 with IC50 values of 6.2 and 13.9 μM, respectively.

New insecticidal bufadienolide, bryophyllin C, from Kalanchoe pinnata.

PubMed

Supratman, U; Fujita, T; Akiyama, K; Hayashi, H

2000-06-01

Two insecticidal bufadienolides (1 and 2) were isolated from a methanol extract of the leaves of Kalanchoe pinnata by bioassay-guided fractionation. Compound 1 was identified as known bryophyllin A (bryotoxin C). The structure of new bufadienolide 2, named bryophyllin C, was determined by spectroscopic methods and the chemical transformation of 1. Compounds 1 and 2 showed strong insecticidal activity against third instar larvae of the silkworm (Bombyx mori), their LD50 values being evaluated as 3 and 5 microg/g of diet, respectively.

Synthesis, structural and antioxidant studies of some novel N-ethyl phthalimide esters.

PubMed

Chidan Kumar, C S; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun

2015-01-01

A series of N-ethyl phthalimide esters 4(a-n) were synthesized and characterized by spectroscopic studies. Further, the molecular structure of majority of compounds were analysed by single crystal X-ray diffraction studies. The X-ray analysis revealed the importance of substituents on the crystal stability and molecular packing. All the synthesized compounds were tested for in vitro antioxidant activity by DPPH radical scavenging, FRAP and CUPRAC methods. Few of them have shown good antioxidant activity.

Labdane diterpenes from Juniperus communis L. berries.

PubMed

Martin, Anne Marie; Queiroz, Emerson Ferreira; Marston, Andrew; Hostettmann, Kurt

2006-01-01

A phytochemical study of the methanol extract of Juniperus communis berries was undertaken. The crude extract was analysed by HPLC-UV and the isolation of the minor compounds was performed by centrifugal partition chromatography. By this means, five diterpenes were isolated, one of which was a new labdane diterpene 15,16-epoxy-12-hydroxy-8(17),13(16),14-labdatrien-19-oic acid. The structures of the isolated compounds were elucidated by spectroscopic methods, including UV, NMR, MS and HR-MS.

Triterpenoid saponins from Dianthus versicolor.

PubMed

Ma, Li; Gu, Yu-Cheng; Luo, Jian-Guang; Wang, Jun-Song; Huang, Xue-Feng; Kong, Ling-Yi

2009-04-01

Seven new pentacyclic triterpenoid saponins, named dianversicosides A-G (1-7), together with nine known compounds, were isolated from the aerial parts of Dianthus versicolor. The structures of 1-7 were elucidated on the basis of spectroscopic data and chemical evidence. The absolute configuration of the 3-hydroxyl-3-methylglutaryl (HMG) group in 1-4 was ascertained by chemical analysis combined with a chiral HPLC method. Cytotoxic activities of the isolated compounds were evaluated against a small panel of cancer and other cell lines.

Lanostane triterpenoids from Ganoderma hainanense J. D. Zhao.

PubMed

Peng, XingRong; Liu, JieQing; Xia, JianJun; Wang, CuiFang; Li, XuYang; Deng, YuanYuan; Bao, NiMan; Zhang, ZhiRun; Qiu, MingHua

2015-06-01

Chemical investigation of the fruiting bodies of Ganoderma hainanense resulted in isolation of fourteen lanostane triterpenoids, including nine ganoderma acids and five ganoderma alcohols, together with five known compounds. Structural elucidation was determined using extensive spectroscopic technologies, Mosher's method and X-ray single crystal diffraction. Three of the compounds showed inhibitory activities against HL-60, SMMC-7721, A-549 and MCF-7 cells with IC50 values of 15.0-40.0 μM. Copyright © 2014 Elsevier Ltd. All rights reserved.

Trichoharzianol, a new antifungal from Trichoderma harzianum F031.

PubMed

Jeerapong, Chotika; Phupong, Worrapong; Bangrak, Phuwadol; Intana, Warin; Tuchinda, Patoomratana

2015-04-15

A new decalin derivative, trichoharzianol (1), together with three known compounds, eujavanicol A (2), 5-hydroxy-3-hydroxymethyl-2-methyl-7-methoxychromone (3), and 4,6-dihydroxy-5-methylphthalide (4), were isolated from Trichoderma harzianum F031. For the first time, compounds 2-4 were reported from the Trichoderma species. Their structures were characterized by spectroscopic methods. Trichoharzianol (1) showed the highest antifungal activity against Colletotrichum gloeosporioides, with a minimum inhibitory concentration (MIC) of 128 μg/mL.

Infrared and Raman Spectroscopic Studies of the Antimicrobial Effects of Garlic Concentrates and Diallyl Constituents on Foodborne Pathogens

PubMed Central

Lu, Xiaonan; Rasco, Barbara A.; Kang, Dong-Hyun; Jabal, Jamie M.F.; Aston, D. Eric; Konkel, Michael E.

2012-01-01

The antimicrobial effects of garlic (Allium sativum) extract (25, 50, 75, 100, and 200 μl/ml) and diallyl sulfide (5, 10 and 20 μM) on Listeria monocytogenes and Escherichia coli O157:H7 cultivated in tryptic soy broth at 4, 22 and 35°C for up to 7 days were investigated. L. monocytogenes was more resistant to garlic extract and diallyl compounds treatment than E. coli O157:H7. Fourier transform Infrared (FT-IR) spectroscopy indicated that diallyl constituents contributed more to the antimicrobial effect than phenolic compounds. This effect was verified by Raman spectroscopy and Raman mapping on single bacteria. Scanning electron microscope (SEM) and transmission electron microscope (TEM) showed cell membrane damage consistent with spectroscopic observation. The degree of bacterial cell injury could be quantified using chemometric methods. PMID:21553849

Bioactive Eunicellin-Based Diterpenoids from the Soft Coral Cladiella krempfi

PubMed Central

Tai, Chi-Jen; Su, Jui-Hsin; Huang, Ming-Shyan; Wen, Zhi-Hong; Dai, Chang-Feng; Sheu, Jyh-Horng

2011-01-01

Four new eunicellin-based diterpenoids, krempfielins A–D (1–4), along with two known compounds (5 and 6) have been isolated from a soft coral Cladiella krempfi. The structures of the new metabolites were elucidated by extensive spectroscopic analysis and by comparison with spectroscopic data of related known compounds. Compounds 5 and 6 were shown to exhibit cytotoxicity against a limited panel of cancer cell lines. Furthermore, compounds 2, 3, 5 and 6 were shown to exert significant in vitro anti-inflammatory activity against LPS-stimulated RAW264.7 macrophage cells. PMID:22073008

Chemical components and tyrosinase inhibitors from the twigs of Artocarpus heterophyllus.

PubMed

Zheng, Zong-Ping; Chen, Sibao; Wang, Shiyun; Wang, Xia-Chang; Cheng, Ka-Wing; Wu, Jia-Jun; Yang, Dajiang; Wang, Mingfu

2009-08-12

An HPLC method was developed and validated to compare the chemical profiles and tyrosinase inhibitors in the woods, twigs, roots, and leaves of Artocarpus heterophyllus . Five active tyrosinase inhibitors including dihydromorin, steppogenin, norartocarpetin, artocarpanone, and artocarpesin were used as marker compounds in this HPLC method. It was discovered that the chemical profiles of A. heterophyllus twigs and woods are quite different. Systematic chromatographic methods were further applied to purify the chemicals in the twigs of A. heterophyllus. Four new phenolic compounds, including one isoprenylated 2-arylbenzofuran derivative, artoheterophyllin A (1), and three isoprenylated flavonoids, artoheterophyllin B (2), artoheterophyllin C (3), and artoheterophyllin D (4), together with 16 known compounds, were isolated from the ethanol extract of the twigs of A. heterophyllus. The structures of compounds 1-4 were elucidated by spectroscopic analysis. However, the four new compounds did not show significant inhibitory activities against mushroom tyrosinase compared to kojic acid. It was found that similar compounds, such as norartocarpetin and artocarpesin in the twigs and woods of A. heterophyllus, contributed to their tyrosinase inhibitory activity.

[Chemical constituents in aerial part of Reineckea carnea].

PubMed

Xu, Xin; Fu, Hong-Zheng

2008-10-01

To study the chemical constituents in the aerial part of Reineckea carnea. The compounds were isolated by extraction, silica gel, gel, and reversed-phase silica gel coloum chromatography, and high-performance liquid chromatography. The structures were identified by various spectroscopic methods including 1D and 2D NMR spectrum, MS, IR, etc. Six compounds were isolated and identified as 1alpha, 3beta-dihydroxy-5beta-pregn-16-en-20-one-3-O-beta-D-glucopyranoside (1), syringaresinol-beta-D-glucoside (2), sophoraflavone B (3), stigmast-5, 22-dien-3-O-beta-D-glucopyranoside (4), daucosterol (5), a-D-glucose (6). Compound 1 was a new compound, coumpounds 2-6 were obtained from the plant for the first time.

Antioxidant neolignans from Cordia americana.

PubMed

Fernández, Lucía R; Cirigliano, Adriana; Fabani, María P; Lima, Beatriz; Alberti, Sebastián; Kramer, Fernando; Tapia, Alejandro A; Cabrera, Gabriela; Palermo, Jorge A; Sánchez, Marianela

2013-12-01

Five new neolignans with a bicyclo[2.2.2]octene framework were isolated from an ethanolic extract of the bark of Cordia americana. The structures and relative configurations of the compounds were elucidated by a combination of spectroscopic methods. All the isolated compounds showed good antioxidant activities in the DPPH radical scavenging (0.5-100 µg/mL) and Ferric-reducing antioxidant power (FRAP, 1-100 µg/mL) assays. One of the compounds displayed mild fungistatic activity at 0.1 µmol/spot against Fusarium virguliforme while, at the same time, all compounds were inactive against several strains of Gram (+) and Gram (-) bacteria at all assayed concentrations (10-1,000 µg/mL). Georg Thieme Verlag KG Stuttgart · New York.

The antioxidant effect of derivatives pyroglutamic lactam

NASA Astrophysics Data System (ADS)

Rohadi, Atisya; Lazim, Azwani Mat; Hasbullah, Siti Aishah

2013-11-01

Diphenylpicrylhydrazyl (DPPH) is widely used for quickly accessing the ability of polyphenols to transfer labile H atoms to radicals. The antioxidant activity of all the synthesized compounds was screened by DPPH method. Compound (4) showed 54% antioxidant potential while all other compounds were found to have moderate to have moderate to mild antioxidant activity ranging from 47-52%. Pyroglutamic lactams have been synthesized stereoselectively in racemic form from levulinic acid as bifunctional adduct using convertible isocyanide in one-pot Ugi 4-center-3-component condensation reaction (U-4C-3CR). The product formed provides biologically interesting products in excellent yields in a short reaction time. The structures of the synthesized compounds were elucidated using spectroscopic data and elemental analysis.

Three New Highly Oxygenated Germacranolides from Carpesium Divaricatum and Their Cytotoxic Activity.

PubMed

Zhang, Tao; Si, Jin-Guang; Zhang, Qiu-Bo; Chen, Jia-Huan; Ding, Gang; Zhang, Hong-Wu; Jia, Hong-Mei; Zou, Zhong-Mei

2018-05-03

Three new highly oxygenated ( 2 ⁻ 4 ), and two known ( 1 and 5 ) germacranolides, were isolated from the whole plant of Carpesium divaricatum . The planar structures and relative configurations of the new compounds were determined by detailed spectroscopic analysis. The absolute configuration of 1 was established using the circular dichroism (CD) method and X-ray diffraction, and the stereochemistry of the new compounds 2 ⁻ 4 were determined using similar CD spectra with 1 . The new compound 2 and the known compound 5 exhibited potent cytotoxicity against hepatocellular cancer (Hep G2) and human cervical cancer (HeLa) cells, superior to those of the positive control cis -platin.

Isolation, characterization, spectroscopic properties and quantum chemical computations of an important phytoalexin resveratrol as antioxidant component from Vitis labrusca L. and their chemical compositions.

PubMed

Güder, Aytaç; Korkmaz, Halil; Gökce, Halil; Alpaslan, Yelda Bingöl; Alpaslan, Gökhan

2014-12-10

In this study, isolation and characterization of trans-resveratrol (RES) as an antioxidant compound were carried out from VLE, VLG and VLS. Furthermore, antioxidant activities were evaluated by using six different methods. Finally, total phenolic, flavonoid, ascorbic acid, anthocyanin, lycopene, β-carotene and vitamin E contents were carried out. In addition, the FT-IR, (13)C and (1)H NMR chemical shifts and UV-vis. spectra of trans-resveratrol were experimentally recorded. Quantum chemical computations such as the molecular geometry, vibrational frequencies, UV-vis. spectroscopic parameters, HOMOs-LUMOs energies, molecular electrostatic potential (MEP), natural bond orbitals (NBO) and nonlinear optics (NLO) properties of title molecule have been calculated by using DFT/B3PW91 method with 6-311++G(d,p) basis set in ground state for the first time. The obtained results show that the calculated spectroscopic data are in a good agreement with experimental data. Copyright © 2014 Elsevier B.V. All rights reserved.

Isolation, characterization, spectroscopic properties and quantum chemical computations of an important phytoalexin resveratrol as antioxidant component from Vitis labrusca L. and their chemical compositions

NASA Astrophysics Data System (ADS)

Güder, Aytaç; Korkmaz, Halil; Gökce, Halil; Alpaslan, Yelda Bingöl; Alpaslan, Gökhan

2014-12-01

In this study, isolation and characterization of trans-resveratrol (RES) as an antioxidant compound were carried out from VLE, VLG and VLS. Furthermore, antioxidant activities were evaluated by using six different methods. Finally, total phenolic, flavonoid, ascorbic acid, anthocyanin, lycopene, β-carotene and vitamin E contents were carried out. In addition, the FT-IR, 13C and 1H NMR chemical shifts and UV-vis. spectra of trans-resveratrol were experimentally recorded. Quantum chemical computations such as the molecular geometry, vibrational frequencies, UV-vis. spectroscopic parameters, HOMOs-LUMOs energies, molecular electrostatic potential (MEP), natural bond orbitals (NBO) and nonlinear optics (NLO) properties of title molecule have been calculated by using DFT/B3PW91 method with 6-311++G(d,p) basis set in ground state for the first time. The obtained results show that the calculated spectroscopic data are in a good agreement with experimental data.

Synthesis, spectroscopic, and molecular structure characterizations of some azo derivatives of 2-hydroxyacetophenone

NASA Astrophysics Data System (ADS)

Albayrak, Çiğdem; Gümrükçüoğlu, İsmail E.; Odabaşoğlu, Mustafa; İskeleli, Nazan Ocak; Ağar, Erbil

2009-08-01

Some novel azo compounds were prepared by the reaction of 2-hydroxyacetophenone with aniline and its substituted derivatives. The structures of synthesized azo compounds were determined by IR, UV-Vis, 1H NMR and 13C NMR spectroscopic techniques and the structures of some of these compounds were also determined by X-ray diffraction studies. Structural analysis using IR in solid state shows that the azo form is favoured in the azo compounds whereas UV-Vis analysis of the azo compounds in solution has shown that there is a azo and ionic form. The azo compounds in the basic solvents dimethylformamide (DMF) and dimethylsulfoxide (DMSO) are both azo and ionic form while these compounds in ethyl alcohol (EtOH) and chloroform (CHCl 3) are only azo form.

Oligomeric secoiridoid glucosides from Jasminum abyssinicum.

PubMed

Gallo, Francesca Romana; Palazzino, Giovanna; Federici, Elena; Iurilli, Raffaella; Monache, Franco Delle; Chifundera, Kusamba; Galeffi, Corrado

2006-03-01

From the root bark of Jasminum abyssinicum (Oleaceae) collected in Congo was isolated tree oligomeric secoiridoid glucosides named craigosides A-C. The three compounds are esters of a cyclopentanoid monoterpene with an iridane skeleton, esterified with three, two and two, respectively, units of oleoside 11-methyl ester. The structures were elucidated by spectroscopic methods and chemical correlations.

Polybrominated diphenyl ethers from the marine organisms Lendenfeldia dendyi and Sinularia dura with anti-MRSa activity

USDA-ARS?s Scientific Manuscript database

Bioassay-guided fractionation of the marine sponge Lendenfeldia dendyi and the soft coral Sinularia dura resulted in the isolation of five polybrominated diphenyl ethers (1-5). The structures of the isolated compounds were determined using spectroscopic methods(lD and 2D NMR) and HRMS analyses. The ...

Phellodonic acid, a new biologically active hirsutane derivative from Phellodon melaleucus (Thelephoraceae, Basidiomycetes).

PubMed

Stadler, M; Anke, T; Dasenbrock, J; Steglich, W

1993-01-01

A new hirsutane derivative, phellodonic acid (1), has been isolated from fermentations of Phellodon melaleucus strain 87113. Its structure was elucidated by spectroscopic methods. The compound exhibits antibiotic activities towards bacteria and fungi. 1 is the first bioactive metabolite from cultures of a species belonging to the family Thelephoraceae.

Phenolic compounds from the flowers of Nepalese medicinal plant Aconogonon molle and their DPPH free radical-scavenging activities.

PubMed

Joshi, Khem Raj; Devkota, Hari Prasad; Watanabe, Takashi; Yahara, Shoji

2014-01-01

Eleven phenolic compounds, quercetin (1), quercetin 3-O-β-d-galactopyranoside (2), quercetin 3-O-(6″-O-galloyl)-β-d-galactopyranoside (3), quercetin 3-O-(6″-O-caffeoyl)-β-d-galactopyranoside (4), quercetin 3-O-β-d-glucopyranoside (5), rutin (6) quercetin 3-O-α-l-arabinopyranoside (7), quercetin 3-O-α-l-arabinofuranoside (8), protocatechulic acid (9), gallic acid (10) and chlorogenic acid (11), were isolated from the flowers of Aconogonon molle, a Nepalese medicinal plant. Structures of these compounds were elucidated on the basis of spectroscopic methods. All these compounds were isolated for the first time from flowers, and five compounds (4, 5, 8, 9 and 11) were isolated for the first time from A. molle. All of these isolated compounds were evaluated for their in vitro antioxidant activity by using the 1,1-diphenyl-2-picrylhydrazyl radical-scavenging method. Quercetin (1), quercetin glycosides (2-8) and gallic acid (10) exhibited potent antioxidant activity.

The crystallographic, spectroscopic and theoretical studies on (E)-2-(((4-chlorophenyl)imino)methyl)-5-(diethylamino)phenol and (E)-2-(((3-chlorophenyl)imino)methyl)-5-(diethylamino)phenol molecules

NASA Astrophysics Data System (ADS)

Demirtaş, Güneş; Dege, Necmi; Ağar, Erbil; Uzun, Sümeyye Gümüş

2018-01-01

Two new salicylideneaniline (SA) derivative compounds (E)-2-(((4-chlorophenyl)imino)methyl)-5-(diethylamino)phenol, compound (I), and (E)-2-(((3-chlorophenyl)imino)methyl)-5-(diethylamino)phenol, compound (II), have been synthesized and characterized by single crystal X-ray diffraction, IR spectroscopy, 1H NMR, 13C NMR and theoretical methods. Both of the compounds which are Schiff base derivatives are isomer of each other. While the compound (I) crystallizes in centrosymmetric monoclinic space group P 21/c, the compound (II) crystallizes in orthorhombic space group P 212121. The theoretical parameters of the molecules have been calculated by using Hartree-Fock (HF) and density functional theory (DFT/B3LYP) with 6-31G (d,p) basis set. These theoretical parameters have been compared with the experimental parameters obtained by XRD. The experimental geometries of the compounds have been superimposed with the theoretical geometries calculated by HF and DFT methods. Furthermore, the theoretical IR calculations, molecular electrostatic potential maps (MEP) and frontier molecular orbitals have been created for the compounds.

Influence of fused aromatic ring on the stability of charge transfer complex between iodine and some five membered heterocyclic molecules through ultrasonic and spectral studies

NASA Astrophysics Data System (ADS)

Ulagendran, V.; Balu, P.; Kannappan, V.; Kumar, R.; Jayakumar, S.

2017-08-01

The charge transfer (CT) interaction between two fused heterocyclic compounds with basic pyrrole group as donors, viz., indole (IND) and carbazole (CAR), and iodine (acceptor) in DMSO medium is investigated by ultrasonic and UV-visible spectral methods at 303 K. The formation of CT complex in these systems is established from the trend in acoustical and excess thermo acoustical properties with molar concentration. The frequency acoustic spectra (FAS) is also carried out on these two systems for two fixed concentrations 0.002 M and 0.02 M, and in the frequency range 1 MHz-10 MHz to justify the frequency chosen for ultrasonic study. The absorption coefficient values in solution are computed and discussed. The formation constants of these complexes are determined using Kannappan equation in ultrasonic method. The formation of 1:1 complexes between iodine and IND, CAR was established by the theory of Benesi - Hildebrand in the UV-visible spectroscopic method. The stability constants of the CT complexes determined by spectroscopic and ultrasonic methods show a similar trend. These values also indicate that the presence of fused aromatic ring influences significantly when compared with K values of similar CT complexes of parent five membered heterocyclic compound (pyrrole) reported by us earlier.

[Chemical Constituents of Ethyl Acetate Fraction of Suaeda glauca].

PubMed

Qiu, Ping; Wang, Qi-zhi; Yin, Min; Wang, Ming; Zhao, You-yi; Shan, Yu; Feng, Xu

2015-04-01

To study the chemical constituents of Suaeda glauca. The chemical constituents were isolated and purified with several separation and purification techniques. Their structures were identified by physicochemical properties and various spectroscopic methods. Ten compounds were isolated from the ethyl acetate fraction as lignoceric acid (1), β-amyrin-n-nonyl ether(2), β-sitosterol(3), β-daucosterol(4), quercetin(5), luteolin(6), luteolin-7-O-β-D-glucoside(7), isorhamnetin(8), scopoletin (9) and stigmasterol(10). Compounds 1, 2, 6, 7, 8, 9 and 10 are isolated from Suaeda genus for the first time and compounds 3 - 5 are isolated from this plant for the first time.

[Study on chemical constituents from leaves of Tripterygium wilfordii].

PubMed

Cao, Xu; Li, Chuangjun; Yang, Jingzhi; Wei, Baixing; Luo, Yongming; Zhang, Dongming

2011-04-01

In order to study the chemical constituents of the leaves of Tripterygium wilfordii and provide references for the bio-active study, we isolated nine compounds from the dried leaves of Tripterygium wilfordii. Their structures were determined by application of spectroscopic (NMR, MS) and chemical methods. These compounds were isolated and identified as (+)-lyoniresinol (1), (+)-isolariciresinol (2), burselignan (3), dibutyl phthalate (4), cyclo-(S-Pro-R-Phe) (5), cyclo-(S-Pro-R-Leu) (6), cyclo-(S-Pro-S-Ile) (7), 3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone (8) and daucosterol (9). Compounds 1-3, 5-8 were isolated from this plant for the first time.

Two new flavanone glycosides of Jasminum lanceolarium and their anti-oxidant activities.

PubMed

Sun, Jia-Ming; Yang, Jun-Shan; Zhang, Hui

2007-03-01

Two new flavanone glucosides, (2S)-5,7,3',5'-tetrahydroxy-flavanone 7-O-beta-D-allopyranoside (1) and (2S)-5,7,3',5'-tetrahydroxy-flavanone 7-O-beta-D-glucopyranosie (2) were isolated from the stems and leaves of Jasminum lanceolarium, along with five known compounds: Betulinaldehyde (3), betulinic acid (4), betulin (5), syringin (6) and Liriodendrin (7). Their structures were determined on the basis of spectroscopic and chemical methods. The isolated compounds were screened for their in vitro antioxidant activity through DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging assay. Compounds 2 demonstrated significant radical scavenging activity.

New sesquiterpenoids from the edible mushroom Pleurotus cystidiosus and their inhibitory activity against α-glucosidase and PTP1B.

PubMed

Tao, Qiao-Qiao; Ma, Ke; Bao, Li; Wang, Kai; Han, Jun-Jie; Zhang, Jin-Xia; Huang, Chen-Yang; Liu, Hong-Wei

2016-06-01

Nine new sesquiterpenoids, clitocybulol derivatives, clitocybulols G-O (1-9) and three known sesquiterpenoids, clitocybulols C-E (10-12), were isolated from the solid culture of the edible fungus Pleurotus cystidiosus. The structures of compounds 1-12 were determined by spectroscopic methods. The absolute configurations of compounds 1-9 were assigned via the circular dichroism (CD) data analysis. Compounds 1, 6 and 10 showed moderate inhibitory activity against protein tyrosine phosphatase-1B (PTP1B) with IC50 values of 49.5, 38.1 and 36.0μM, respectively. Copyright © 2016. Published by Elsevier B.V.

A new flavonoid from Sophora flavescens Ait.

PubMed

Huang, Rong; Liu, Yi; Zhao, Lin-Lin; Chen, Xi-Xin; Wang, Feng; Cai, Wei; Chen, Lei

2017-10-01

A new flavonoid, 8-(3-hydroxymethyl-2-butenyl)-5,7,2',4'-tetrahydroxyflavanone (1), along with seven known compounds, (2R)-3α,7,4'-Trihydroxy -5-methoxy-8-prenylflavanone (2), (2R)-3β,7,4'- Trihydroxy-5-methoxy-8-prenylflavanone (3), 3,7-dihydroxycoumarin (4), Shandougenines B (5), Specionin (6), Kushenol N (7) and Kushenol I (8) were isolated from the roots of Sophora flavescens. Among them, Compound 5 was isolated from Leguminous plants, and compounds 4 and 6 were isolated from Sophora flavescens for the first time. Their structures were elucidated by the aid of NMR, HRMS, HMBC and CD spectroscopic methods.

Spectroscopic methods for the photodiagnosis of nonmelanoma skin cancer.

PubMed

Drakaki, Eleni; Vergou, Theognosia; Dessinioti, Clio; Stratigos, Alexander J; Salavastru, Carmen; Antoniou, Christina

2013-06-01

The importance of dermatological noninvasive imaging techniques has increased over the last decades, aiming at diagnosing nonmelanoma skin cancer (NMSC). Technological progress has led to the development of various analytical tools, enabling the in vivo/in vitro examination of lesional human skin with the aim to increase diagnostic accuracy and decrease morbidity and mortality. The structure of the skin layers, their chemical composition, and the distribution of their compounds permits the noninvasive photodiagnosis of skin diseases, such as skin cancers, especially for early stages of malignant tumors. An important role in the dermatological diagnosis and disease monitoring has been shown for promising spectroscopic and imaging techniques, such as fluorescence, diffuse reflectance, Raman and near-infrared spectroscopy, optical coherence tomography, and confocal laser-scanning microscopy. We review the use of these spectroscopic techniques as noninvasive tools for the photodiagnosis of NMSC.

Spectroscopic methods for the photodiagnosis of nonmelanoma skin cancer

NASA Astrophysics Data System (ADS)

Drakaki, Eleni; Vergou, Theognosia; Dessinioti, Clio; Stratigos, Alexander J.; Salavastru, Carmen; Antoniou, Christina

2013-06-01

The importance of dermatological noninvasive imaging techniques has increased over the last decades, aiming at diagnosing nonmelanoma skin cancer (NMSC). Technological progress has led to the development of various analytical tools, enabling the in vivo/in vitro examination of lesional human skin with the aim to increase diagnostic accuracy and decrease morbidity and mortality. The structure of the skin layers, their chemical composition, and the distribution of their compounds permits the noninvasive photodiagnosis of skin diseases, such as skin cancers, especially for early stages of malignant tumors. An important role in the dermatological diagnosis and disease monitoring has been shown for promising spectroscopic and imaging techniques, such as fluorescence, diffuse reflectance, Raman and near-infrared spectroscopy, optical coherence tomography, and confocal laser-scanning microscopy. We review the use of these spectroscopic techniques as noninvasive tools for the photodiagnosis of NMSC.

One-Pot Synthesis, Spectroscopic and Physicochemical Studies of Quinoline Based Blue Emitting Donor-Acceptor Chromophores with Their Biological Application.

PubMed

Asiri, Abdullah M; Khan, Salman A; Al-Thaqafya, Saad H

2015-09-01

Blue emitting cyano substituted isoquinoline dyes were synthesized by one-pot multicomponent reactions (MCRs) of aldehydes, malononitrile, 6-methoxy-1,2,3,4-tetrahydro-naphthalin-1-one and ammonium acetate. Results obtained from spectroscopic (FT-IR, (1)H-NMR, (13)C-NMR, EI-MS) and elemental analysis of synthesized compounds was in good agreement with their chemical structures. UV-vis and fluorescence spectroscopy measurements proved that all compounds are good absorbent and fluorescent. Fluorescence polarity study demonstrated that these compounds were sensitive to the polarity of the microenvironment provided by different solvents. In addition, spectroscopic and physicochemical parameters, including electronic absorption, excitation coefficient, stokes shift, oscillator strength, transition dipole moment and fluorescence quantum yield were investigated in order to explore the analytical potential of synthesized compounds. The anti-bacterial activity of these compounds were first studied in vitro by the disk diffusion assay against two Gram-positive and two Gram-negative bacteria then the minimum inhibitory concentration (MIC) was determined with the reference of standard drug chloramphenicol. The results displayed that compound 3 was better inhibitors of both types of the bacteria (Gram-positive and Gram-negative) than chloramphenicol. Graphical Abstract ᅟ.

Theoretical, spectroscopic and antioxidant activity studies on (E)-2-[(2-fluorophenylimino)methyl]-4-hydroxyphenol and (E)-2-[(3-fluorophenylimino)methyl]-4-hydroxyphenol compounds

NASA Astrophysics Data System (ADS)

Alaşalvar, Can; Güder, Aytaç; Gökçe, Halil; Albayrak Kaştaş, Çiğdem; Çatak Çelik, Raziye

2017-04-01

We studied synthesis and characterization of the title compounds by using X-ray crystallographic technique, FT-IR spectroscopy, UV-Vis spectroscopy and Density functional method. Optimized geometry, vibrational frequencies and UV-Vis parameters of the title compounds in the ground state have been calculated by using B3LYP with the 6-311G+ (d,p) basis set. HOMO - LUMO energy gap, Non-linear optical properties are performed at B3LYP/6-311G+(d,p) level. For determination of antioxidant properties of the title compounds (CMPD1 and CMPD2) have been investigated by using different methods, i.e. ferric reducing antioxidant power (FRAP), hydrogen peroxide scavenging (HPSA), free radical scavenging (FRSA) and ferrous ion chelating activities (FICA). In comparison with standard antioxidants (BHA, BHT, and α-tocopherol), CPMD1 and CMPD2 have influential FRAP, HPSA, FRSA and FICA.

Protoberberine alkaloids and their reversal activity of P-gp expressed multidrug resistance (MDR) from the rhizome of Coptis japonica Makino.

PubMed

Min, Yong Deuk; Yang, Min Cheol; Lee, Kyu Ha; Kim, Kyung Ran; Choi, Sang Un; Lee, Kang Ro

2006-09-01

Six protoberberine alkaloids were isolated from the chloroform layer of the rhizome of Coptis japonica Makino (Ranunculaceae). The structures of the isolated compounds were determined to be 6-([1,3]dioxolo[4,5-g]isoquinoline-5-carbonyl)-2,3-dimethoxy-benzoic acid methyl ester (1), oxyberberine (2), 8-oxo-epiberberine (3), 8-oxocoptisine (4), berberine (5) and palmatine (6) by physicochemical and spectroscopic methods. The compound 3 (8-oxo-epiberberine) was first isolated from natural sources. The compounds were tested for cytotoxicity against five tumor cell lines in vitro by SRB method, and also tested for the MDR reversal activities. Compound 4 was of significant P-gp MDR inhibition activity with ED50 value 0.018 microg/mL in MES-SA/DX5 cell and 0.0005 microg/mL in HCT15 cell, respectively.

[Study on secondary metabolites of marine fungus Penicillium sp. FS60 from the South China Sea].

PubMed

Zhang, Ling; Li, Dong-Li; Chen, Yu-Chan; Tao, Mei-Hua; Zhang, Wei-Min

2012-07-01

To study the secondary metabolites of the marine fungus Penicillium sp. FS60 from the South China Sea and their cytotoxicities. The compounds were isolated from the culture of strain FS60 by various chromatographic methods (silica gel, reverse silica gel, Sephadex-LH20, preparative TLC, HPLC and PTLC) and recrystallization. Their structures were identified by extensive analysis of their spectroscopic data. Compounds were tested for their cytotoxicities against SF-268, MCF-7, and NCI-H460 cell lines by SRB method. While, Compounds were tested for their antibacterial activities against S. aureus, E. coli and P. aeruginosa. Seven compounds were isolated from the culture and identified as methyl 2,4-dihydroxy-3,5,6-trimethylbenzoate (1), 4-hydroxyacetophenone (2), 5-hydroxymethyl-furoic acid (3), isochromophilones VIII (4), ergosterol (5), ergosterol peroxide (6), and cerevisterol (7). Compound 1 is isolated from the genus Penicillium for the first time. Compound 3 is demonstrated to have significant inhibition against S. aureus and P. aeruginosa. Compound 4 is demonstrated to have significant inhibition against the three cell lines.

Isolation, identification and antioxidant activity of bound phenolic compounds present in rice bran.

PubMed

Wang, Wei; Guo, Jia; Zhang, Junnan; Peng, Jie; Liu, Tianxing; Xin, Zhihong

2015-03-15

The bound phenolic compounds in rice bran were released and extracted with ethyl acetate based on alkaline digestion. An investigation of the chemical constituents of EtOAc extract has led to the isolation of a new compound, para-hydroxy methyl benzoate glucoside (8), together with nine known compounds, cycloeucalenol cis-ferulate (1), cycloeucalenol trans-ferulate (2), trans-ferulic acid (3), trans-ferulic acid methyl ester (4), cis-ferulic acid (5), cis-ferulic acid methyl ester (6), methyl caffeate (7), vanillic aldehyde (9) and para-hydroxy benzaldehyde (10). The structures of these compounds were determined using a combination of spectroscopic methods and chemical analysis. Among the compounds isolated, compound 3, 5 and 7 exhibited strong DPPH and ABTS(+) radical scavenging activities, followed by compounds 4 and 6. Compound 1 and 2 showed potent DPPH and ABTS(+) radical scavenging activities, compound 8 displayed moderate antioxidant activity against ABTS(+) radical, whereas compound 9 and 10 showed weak antioxidant activity. Copyright © 2014 Elsevier Ltd. All rights reserved.

Steroidal glycosides from the roots of Asclepias curassavica.

PubMed

Warashina, Tsutomu; Noro, Tadataka

2008-03-01

Twenty-six new acylated-oxypregnane glycosides were obtained along with three known cardenolide glycosides from the roots of Asclepias curassavica (Asclepiadaceae). The new compounds were confirmed to contain 12-O-benzoylsarcostin, 12-O-benzoyldeacylmetaplexigenin, kidjolanin, and 12-O-benzoyltayloron, and one new acylated-oxypregnane, 12-O-(E)-cinnamoyltayloron, as their aglycones, using both spectroscopic and chemical methods.

Chemistry of Amadori rearrangement products: analysis, synthesis, kinetics, reactions, and spectroscopic properties.

PubMed

Yaylayan, V A; Huyghues-Despointes, A

1994-01-01

The chemistry of the key intermediate in the Maillard reaction, the Amadori rearrangements product, is reviewed covering the areas of synthesis, chromatographic analyses, chemical and spectroscopic methods of characterization, reactions, and kinetics. Synthetic strategies involving free and protected sugars are described in detail with specific synthetic procedures. GC- and HPLC-based separations of Amadori products are discussed in relation to the type of columns employed and methods of detection. Applications of infrared (IR) and nuclear magnetic resonance (NMR) spectroscopy for structural elucidation of Amadori products are also reviewed. In addition, mass spectrometry of free, protected, and protein-bound Amadori products under different ionization conditions are presented. The mechanism of acid/base catalyzed thermal degradation reactions of Amadori compounds, as well as their kinetics of formation, are critically evaluated.

New phenylpropanoid and 6H-dibenzo[b,d]pyran-6-one derivatives from the stems of Dasymaschalon rostratum.

PubMed

Yu, Zhang-Xin; Niu, Zhi-Gang; Li, Xiao-Bao; Zheng, Cai-Juan; Song, Xin-Ming; Chen, Guang-Ying; Song, Xiao-Ping; Han, Chang-Ri; Wu, Shu-Xian

2017-04-01

Three new phenylpropanoid derivatives, dasymaroacid A (1), dasymaroesters B and C (2 and 3), and one new polyoxygenated 6H-dibenzo[b,d]pyran-6-one derivative dasymarolactone D (4), together with seven known compounds (5-11), were isolated from the stems of Dasymaschalon rostratum Merr. Compounds 1 and 2 are unusual phenylpropanoid derivatives with a polymethyl substituted cyclopentene conjugated diketone as a substituent, and 3 is a unique cinnamic acid detective with a polymethyl substituted cyclohexene conjugated triketone as a substituent. Their structures were elucidated by extensive spectroscopic methods and chemical method, and 4 was further confirmed by the single crystal X-ray diffraction method. Compounds 1-4 and 7 showed weak anti-HIV-1 activities with EC 50 values ranged from 16.44 to 25.91μM. Copyright © 2017 Elsevier B.V. All rights reserved.

Two new coumarins from Micromelum falcatum with cytotoxicity and brine shrimp larvae toxicity.

PubMed

Luo, Xiongming; He, Weihong; Yin, Hao; Li, Qingxin; Liu, Qiao; Huang, Yongzhong; Zhang, Si

2012-06-06

Two new coumarins, 7-methoxy-8-(2-hydroxmethyl-1-O-isovaleryl-4-butenyl)-coumarin (1) and 7-methoxy-8-(1-hydroxy-2-O-β-glucopyranosyl-3-methyl-4-butene-1-yl)coumarin (2), and twelve known coumarins 3-14 were isolated from the stem bark of Micromelum falcatum. The structures of compounds 1-14 were elucidated by extensive spectroscopic data analyses. The toxicity of compounds 1-14 was tested using a brine shrimp assay and in vitro antiproliferative assay against mammary cancer (F10) and lung cancer (HvEvc) cell lines by the MTT method. Some compounds had moderate activities. All compounds were also tested against the microorganisms Bacillus subtilis, Bacillus thuringiensis and Escherichia coli, but no activity was observed.

The antioxidant effect of derivatives pyroglutamic lactam

DOE Office of Scientific and Technical Information (OSTI.GOV)

Rohadi, Atisya; Lazim, Azwani Mat; Hasbullah, Siti Aishah

Diphenylpicrylhydrazyl (DPPH) is widely used for quickly accessing the ability of polyphenols to transfer labile H atoms to radicals. The antioxidant activity of all the synthesized compounds was screened by DPPH method. Compound (4) showed 54% antioxidant potential while all other compounds were found to have moderate to have moderate to mild antioxidant activity ranging from 47–52%. Pyroglutamic lactams have been synthesized stereoselectively in racemic form from levulinic acid as bifunctional adduct using convertible isocyanide in one-pot Ugi 4-center-3-component condensation reaction (U-4C-3CR). The product formed provides biologically interesting products in excellent yields in a short reaction time. The structures ofmore » the synthesized compounds were elucidated using spectroscopic data and elemental analysis.« less

Heptyl vicianoside and methyl caramboside from sour star fruit.

PubMed

Yang, Dan; Jia, Xuchao; Xie, Haihui

2018-04-23

Two new alkyl glycosides, heptyl vicianoside (1) and methyl 2-O-β-d-fucopyranosyl-α-l-arabinofuranoside (methyl caramboside, 4), were isolated from the sour fruit of Averrhoa carambola L. (Oxalidaceae), along with octyl vicianoside (2), cis-3-hexenyl rutinoside (3), and methyl α-d-fructofuranoside (5). Their structures were determined by spectroscopic and chemical methods. Compounds 2, 3, and 5 were obtained from the genus Averrhoa for the first time. All the compounds were evaluated for in vitro α-glucosidase, pancreatic lipase, and acetylcholinesterase inhibitory activities, but none of them were potent.

A new p-hydroxybenzoic acid derivative from an endophytic fungus Penicillium sp. of Nerium indicum.

PubMed

Ma, Yang-Min; Qiao, Ke; Kong, Yang; Guo, Lin-Xin; Li, Meng-Yun; Fan, Chao

2017-12-01

A new p-hydroxybenzoic acid derivative named 4-(2'R, 4'-dihydroxybutoxy) benzoic acid (1) was isolated from the fermentation of Penicillium sp. R22 in Nerium indicum. The structure was elucidated by means of spectroscopic (HR-ESI-MS, NMR, IR, UV) and X-ray crystallographic methods. The antibacterial and antifungal activity of compound 1 was tested, and the results showed that compound 1 revealed potent antifungal activity against Colletotrichum gloeosporioides, Alternaria alternata, and Alteranria brassicae with MIC value of 31.2 μg/ml.

A new nortriterpenoid and an ergostane-type steroid from the fruiting bodies of the fungus Ganoderma resinaceum.

PubMed

Chen, Xian-Qiang; Chen, Ling-Xiao; Li, Shao-Ping; Zhao, Jing

2017-12-01

One new expoxy nortriterpenoid (1) and one new ergostane-type steroid (2), together with seven known steroids (3-9), were obtained from the fruiting bodies of the fungus Ganoderma resinaceum. The new compounds were elucidated on the basis of extensive spectroscopic data (MS, NMR, IR, and UV) and the known compounds were identified by comparing spectroscopic data with those reported in literature.

Synthesis, spectroscopic characterization and computational chemical study of 5-cyano-2-thiouracil derivatives as potential antimicrobial agents

NASA Astrophysics Data System (ADS)

Rizk, Sameh A.; El-Naggar, Abeer M.; El-Badawy, Azza A.

2018-03-01

A series of 5-cyano-2-thiouracil derivatives, containing diverse hydrophobic groups in the 2-, 4- and 6-positions, were synthesized through one pot reaction of thiophene 2-carboxaldehyde, ethylcyanoacetate and thiourea using classic reflux-based method as well as microwave-assisted methods. Such prepared compounds were reacted with different electrophilic reagents to synthesize potent anti-microbial agents, e.g. 1,3,4-thiadiazinopyrimidine, hydrazide and triazolopyrimidine derivatives (compounds 4a-e, 9 and 10-12) respectively. The density functional theory (DFT) was then applied to explore the structural and electronic characteristics of these materials. It is found that compound 12 exhibited the highest antibacterial and antifungal activity against C. Albicans showing six-fold increasing biological affinity compared to that of Colitrimazole drug with MIC values 7.8 and 49 μg/mL, respectively. All the synthesized compounds have been characterized based on their elemental analyses and spectral data. Such compounds can be submitted to in vivo antimicrobial studies in future works.

The spectroscopic (FT-IR, UV-vis), Fukui function, NLO, NBO, NPA and tautomerism effect analysis of (E)-2-[(2-hydroxy-6-methoxybenzylidene)amino]benzonitrile.

PubMed

Demircioğlu, Zeynep; Kaştaş, Çiğdem Albayrak; Büyükgüngör, Orhan

2015-03-15

A new o-hydroxy Schiff base, (E)-2-[(2-hydroxy-6-methoxybenzylidene)amino]benzonitrile was isolated and investigated by experimental and theoretical methodologies. The solid state molecular structure was determined by X-ray diffraction method. The vibrational spectral analysis was carried out by using FT-IR spectroscopy in the range of 4000-400cm(-)(1). Theoretical calculations were performed by density functional theory (DFT) method using 6-31G(d,p) basis set. The results of the calculations were applied to simulated spectra of the title compound, which show excellent agreement with observed spectra. The UV-vis spectrum of the compound was recorded in the region 200-800 nm in several solvents and electronic properties such as excitation energies, and wavelengths were calculated by TD-DFT/B3LYP method. The most prominent transitions were corresponds to π→π∗. Hybrid density functional theory (DFT) was used to investigate the enol-imine and keto-amine tautomers of titled compound. The titled compound showed the preference of enol form, as supported by X-ray and spectroscopic analysis results. The geometric and molecular properties were compaired for both enol-imine and keto-amine forms. Additionally, geometry optimizations in solvent media were performed with the same level of theory by the integral equation formalism polarizable continuum (IEF-PCM). Stability of the molecule arises from hyperconjugative interactions, charge delocalization and intramolecular hydrogen bond has been analyzed using natural bond orbital (NBO) analysis. Mulliken population method and natural population analysis (NPA) have been studied. Also, condensed Fukui function and relative nucleophilicity indices calculated from charges obtained with orbital charge calculation methods (NPA). Molecular electrostatic potential (MEP) and non linear optical (NLO) properties are also examined. Copyright © 2014 Elsevier B.V. All rights reserved.

EPR spectral investigation of radiation-induced radicals of gallic acid.

PubMed

Tuner, Hasan

2017-11-01

In the present work, spectroscopic features of the radiation-induced radicals of gallic acid compounds were investigated using electron paramagnetic resonance (EPR) spectroscopy. While un-irradiated samples presented no EPR signal, irradiated samples exhibited an EPR spectrum consisting of an intense resonance line at the center and weak lines on both sides. Detailed microwave saturation investigations were carried out to determine the origin of the experimental EPR lines. It is concluded that the two side lines of the triplet satellite originate from forbidden "spin-flip" transitions. The spectroscopic and structural features of the radiation-induced radicals were determined using EPR spectrum fittings. The experimental EPR spectra of the two gallic acid compounds were consistent with the calculated EPR spectroscopic features of the proposed radicals. It is concluded that the most probable radicals are the cyclohexadienyl-type, [Formula: see text] radicals for both compounds.

The unusual canangafruticosides A-E: five monoterpene glucosides, two monoterpenes and a monoterpene glucoside diester of the aryldihydronaphthalene lignan dicarboxylic acid from leaves of Cananga odorata var. fruticosa.

PubMed

Nagashima, Jiro; Matsunami, Katsuyoshi; Otsuka, Hideaki; Lhieochaiphant, Duangporn; Lhieochaiphant, Sorasak

2010-09-01

From the leaves of Cananga odorata var. fruticosa, five unusual monoterpene glucosides, named canangafruticosides A-E (1-5), along with two unusual non-glucosidic monoterpenes (6, 7) were isolated. An aryldihydronaphthalene-type lignan dicarboxylate (8) was also isolated, with two moles of canangafruticoside A (1) on its ester moiety. This lignan also showed strong blue fluorescence emission under basic conditions. The structures of these compounds were elucidated by means of spectroscopic methods, with their absolute configurations determined by application of the modified Mosher's method to a compound chemically derived from canangafruticoside E. (c) 2010 Elsevier Ltd. All rights reserved.

Signs of antimetastatic activity of palladium complexes of methylenediphosphonic acid in IR spectra

NASA Astrophysics Data System (ADS)

Tolstorozhev, G. B.; Skornyakov, I. V.; Pekhnio, V. I.; Kozachkova, A. N.; Sharykina, N. I.

2012-07-01

We have used Fourier transform IR spectroscopy methods to study normal mouse lung tissue and also after subcutaneous transplantation of a B-16 melanoma tumor in the tissue. We also studied tissues with B-16 melanoma after they were treated with coordination compounds based on palladium complexes of methylenediphosphonic acid. The IR spectra of the lung tissues with metastases in the region of the C = O stretching vibrations are different from the IR spectra of normal tissue. We identified spectroscopic signs of the presence of metastases in the lung. We show that when a cancerous tumor is treated with a preparation of palladium complexes of methylenediphosphonic acid, the spectroscopic signs of the presence of metastases in the lung are missing. After treatment with the optimal dose of this drug, the IR spectrum of the lung tissue in which multiple metastases were present before treatment corresponds to the spectrum of normal tissue. We have determined the efficacy of the antitumor activity of coordination compounds based on palladium complexes of methylenediphosphonic acid.

Vibrational spectroscopic (FT-IR, FT-Raman) and quantum mechanical study of 4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a][1,4] diazepine

NASA Astrophysics Data System (ADS)

Kuruvilla, Tintu K.; Prasana, Johanan Christian; Muthu, S.; George, Jacob

2018-04-01

The spectroscopic properties of 4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno [3,2-f] [1,2,4] triazolo [4,3-a] [1,4] diazepine were investigated in the present study using FT-IR and FT-Raman techniques. The results obtained were compared with quantum mechanical methods, as it serves as an important tool in interpreting and predicting vibrational spectra. The optimized molecular geometry, the vibrational wavenumbers, the infrared intensities and Raman scattering were calculated using density functional theory B3LYP method with 6-311++g (d,p) basis set. All the experimental results were in line with the theoretical data. The molecular electrostatic potential (MEP) and HOMO LUMO energies of the title compound were accounted. The results indicated that the title compound has a lower softness value (0.27) and high electrophilicity index (4.98) hence describing its biological activity. Further, natural bond orbital was also analyzed as part of the work. Fukui functions were calculated in order to explain the chemical selectivity or the reactivity site in 4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno [3,2-f] [1,2,4] triazolo [4,3-a] [1,4] diazepine. The thermodynamic properties of the title compound were closely examined at different temperatures. It revealed the correlations between heat capacity (C), entropy (S) and enthalpy changes (H) with temperatures. The paper further explains that the title compound can act as good antidepressant through molecular docking studies.

Estrogenic activity of constituents from the rhizomes of Rheum undulatum Linné.

PubMed

Park, SeonJu; Kim, Yun Na; Kwak, Hee Jae; Jeong, Eun Ju; Kim, Seung Hyun

2018-02-15

Stilbenes have been reported to be phytoestrogen compounds owing to its structural similarity to the estrogenic agent diethylstilbestrol. To find new stilbene-derivative phytoestrogens, isolation of stilbene-rich R. undulatum was performed and led to identify six new compounds (1-5 and 28), one newly determined absolute configurations compound (27) together with 21 previously reported compounds (6-26). The structures of compounds were determined on the basis of extensive spectroscopic methods including 1D and 2D NMR and CD spectra data. All the isolated compounds were tested for their estrogenic activities in HepG2 cells transiently transfected with ERα, ERβ and ERE-reporter plasmid. Among them, stilbene-derivatives, piceatannol 3'-O-β-d-xylopyranoside (12), cis-rhaponticin (16) and rhapontigenin 3'-O-β-d-glucopyranoside (17), showed the more potent binding affinity for estrogen receptors than 17β-estrodiol. Copyright © 2018 Elsevier Ltd. All rights reserved.

Methyl-3,4-dihydroxybenzoate and 9-10-dihydrophenanthrene-2,4,7-triol two phenolic compounds from Dioscorea alata L. and their antioxidant activity

NASA Astrophysics Data System (ADS)

Aminah, N. S.; Yulvia, A.; Tanjung, M.

2017-09-01

Two phenolic compounds namely: methyl-3,4-dihydroxybenzoate (1) and 9,10-dihydrophenanthrene-2,4,7-triol (2) had been isolated for the first time from the tuber of Dioscorea alata L. The extraction of two compounds were done by maceration method using methanol as solvent, followed by partition with n-hexane and ethyl acetate. The ethyl acetate extract was separated and purified using various chromatographic techniques yielded pure compounds. The structure of isolated compounds were determined based on spectroscopic data, including UV-Vis, 1D and 2D NMR spectra. Compounds (1), (2) and ascorbic acid as a comparator were evaluated for their antioxidant properties against DPPH, showing their IC50 were 9,41 ± 0,08; 23,52 ± 0,05; and 10,95 ± 0,08 ppm, respectively.

[Studies on chemical constituents from stem barks of Fraxinus paxiana].

PubMed

Ma, Zhi-jing; Zhao, Zhi-juan

2008-08-01

To investigate the chemical constituents of Fraxinus paxiana. The chemical constituents were isolated and purified by chromatographic techniques and the structures of the compounds were identified with or by spectroscopic methods. Fifteen compounds were obtained from the methanol extract of F. paxiana and their structures were elucidated as esculin (1), esculetin (2), fraxin (3), fraxetin (4), salidroside (5), osmanthuside H (6), liriodendrin (7), 3-(4-beta-D-glucopyranosyloxy-3-methoxy)-phenyl-2E-propenol (8), threo-syringylglycerol (9), euscaphic acid (10), 3-hydroxy-1-(4-hydroxy-3, 5-dimethoxyphenyl)-1-propanone (11), omega-hydroxypropioguaiacone (12), sinapyladehyde (13), betulinic acid (14) and mannitol (15). All compounds were obtained from this plant for the first time.

Metabolites with Gram-negative bacteria quorum sensing inhibitory activity from the marine animal endogenic fungus Penicillium sp. SCS-KFD08.

PubMed

Kong, Fan Dong; Zhou, Li Man; Ma, Qing Yun; Huang, Sheng Zhuo; Wang, Pei; Dai, Hao Fu; Zhao, You Xing

2017-01-01

Three new compounds named penicitor A, aculene E and penicitor B, as well as four known compounds, were isolated from the fermentation broth of Penicillium sp. SCS-KFD08 associated with a marine animal Sipunculus nudus from the Haikou bay of China. Their planar structures and absolute configurations were unambiguously elucidated by spectroscopic data, Mosher's method, CD spectrum analysis along with quantum ECD calculation. Among them, compounds 2-7 showed quorum sensing inhibitory activity against Chromobacterium violaceum CV026, and could significantly reduce violacein production in N-hexanoyl-l-homoserine lactone (C6-HSL) induced C. violaceum CV026 cultures at sub-inhibitory concentrations.

Anti-inflammatory constituents from Psychotria prainii H. Lév.

PubMed

Tran, Phi Hung; Le, Viet Dung; Do, Thi Ha; Nguyen, Thi Luyen; Nguyen, Phuong Thao; Nguyen, Trong Thong; Nguyen, Tien Dat

2017-12-06

One new and three known compounds were isolated from the ethanol extract of Psychotria prainii aerial parts. By means of spectroscopic methods, their structures were elucidated to be deacetylasperulosidic acid 6-ethyl ether (1), asperulosidic acid (2), asperuloside (3) and obtucarbamates C (4). The isolated compounds were evaluated for their inhibitory effect on NO production in LPS-stimulated RAW264.7 cells. Among them, compounds 2 and 4 exhibited strong effect with the IC 50 values of 5.75 ± 0.85 and 6.92 ± 0.43 μM, respectively. This is the first report for the chemical composition and biological activity of P. prainii.

Rauvolfianine, a new antimycobacterial glyceroglycolipid and other constituents from Rauvolfia caffra. Sond (Apocynaceae).

PubMed

Ebeh Messanga, Robert; Dominique Serge, Ngono Bikobo; Abouem A Zintchem, Auguste; Norbert, Mbabi Nyemeck Ii; Esther Del Florence, Moni Ndedi; Patrick Hervé, Betote Diboué; Maximilienne Ascension, Nyegue; Alex De Théodore, Atchadé; Dieudonné Emmanuel, Pegnyemb; Christian G, Bochet; Koert, Ulrich

2017-08-16

The chemical investigation of the extract of the dried leaves of Rauvolfia caffra (Sond) (synonym Rauvolfia macrophylla) (Apocynaceae) led to isolation of a new glycoside derivative, rauvolfianine (1) as well as six known compounds: oleanolic acid (2), sitosterol-3-O-β-D-glucopyranoside (3), betulinic acid (4), vellosimine (5), sarpagine (6) and D-fructofuranosyl-β-(2→1)-α-D-glucopyranoside (7). Compounds 1, 2, 3, 4 and 7 were evaluated for antitubercular activity. Compounds 1 and 2 were the most active (MIC = 7.8125 and 31.25 μg/mL) towards the Isoniazid resistant strain of Mycobacterium tuberculosis AC45. Their structures and relative stereochemistry were elucidated by spectroscopic methods.

One new galloyl glycoside from fresh leaves of Psidium guajava L.

PubMed

Shu, Ji-cheng; Chou, Gui-xin; Wang, Zheng-tao

2010-03-01

To investigate the chemical constituents of Psidium Guajava L, the EtOH/H2O extract of the fresh leaves was subjected to various chromatography. Five constituents with galloyl moiety were isolated and elucidated as 1-O-(1, 2-propanediol)-6-O-galloyl-beta-D-glucopyranoside (1), gallic acid (2), ellagic acid (3), ellagic acid-4-O-beta-D-glucopyranoside (4) and quercetin-3-O-(6"-galloyl) beta-D-galactopyranoside (5) by spectroscopic methods, including 2D NMR and HR-ESI-MS spectrometry as well as by comparison with published data. Compounds 4 and 5 were obtained from P. guajava for the first time, and compound 1 is a new polyhydroxyl compound.

Cassane Diterpenoids from the Pericarps of Caesalpinia bonduc.

PubMed

Zhang, Panpan; Tang, Chunping; Yao, Sheng; Ke, Changqiang; Lin, Ge; Hua, Hui-Ming; Ye, Yang

2016-01-22

Ten new cassane-type diterpenoids, caesalbonducins D-F (1-3), 6-deacetoxybonducellpin B (4), 3-acetoxy-α-caesalpin (5), 2(3)-en-α-caesalpin (6), 1α-hydroxycaesalpinin J (7), 1α-hydroxy-6-decaetoxysalpinin J (8), 6α-hydroxycaesall M (9), and 6α-hydroxy-14(17)-dehydrocaesalpin F (10), along with eight known compounds (11-18), were isolated from the pericarps of Caesalpinia bonduc. Compounds 1-3 and 11 are methyl-migrated cassane-type diterpenoids with a 19(4→3)-cassane skeleton. The structures of 1-10 were elucidated on the basis of 1D and 2D NMR methods and other spectroscopic analysis. The neuroprotective effects of the isolated compounds were evaluated.

Nonsaponifiable lipid components of the pollen of elder (Sambucus nigra L.).

PubMed

Stránsky, K; Valterová, I; Fiedler, P

2001-11-30

Pollen of the elder (Sambucus nigra L.) was extracted with chloroform-methanol. The extract was separated by column chromatography into the following groups of compounds: hydrocarbons (8.7%). polycyclic aromatic hydrocarbons (0.2%), complex esters (5.2%), triglycerides (18.7%), hydroxy esters (27.9%), free fatty acids and alcohols (16.8%), free sterols (6.8%), and triterpenic alcohols (4.0%). The nonsaponifiable components (hydrocarbons, fatty acids, alcohols, and sterols) were examined in detail using spectroscopic and chromatographic methods (IR spectroscopy, GC, and GC-MS). The identified compounds were characterized by their mass spectra and Kováts retention indices. The double bond positions and their configurations in unsaturated compounds are also reported.

Flavonoids from the stems of Croton caudatus Geisel. var. tomentosus Hook.

PubMed

Zou, Guo-An; Su, Zhi-Heng; Zhang, Hong-Wu; Wang, Yuan; Yang, Jun-Shan; Zou, Zhong-Mei

2010-02-26

A new flavone, named crotoncaudatin (1), was isolated from the stems of Croton caudatus Geisel. var. tomentosus Hook., together with nine known analogues: 3,5,6,7,8,3',4'-heptamethoxyflavone (2), tangeretin (3), nobiletin (4), 5,6,7,4'-tetramethoxy-flavone (5), sinensetin (6), kaempferol (7), tiliroside (8), kaempferol-3-O-rutinoside (9) and rutin (10). The structures of the above compounds were established by a combination of spectroscopic methods, including HR-ESI-MS, 1H-NMR, 13C-NMR, HMQC and HMBC spectra. All compounds were isolated from and identified in this species for the first time and compounds 1-6 are new for the genus Croton.

Occurrence of psilocybin and psilocin in Psilocybe pseudobullacea (Petch) Pegler from the Venezuelan Andes.

PubMed

Marcano, V; Morales Méndez, A; Castellano, F; Salazar, F J; Martinez, L

1994-07-08

Using thin-layer chromatographic and spectroscopic (UV) methods two Psilocybe species from the Venezuelan Andes were analysed for the hallucinogens psilocybin and psilocin. These species are: P. montana (Pers. ex Fr.) Kumm and P. pseudobullacea (Petch) Pegler. Both hallucinogens were found in P. pseudobullacea, while P. montana was found to be exempt of these compounds.

Flavonoids, Phenolic Acids and Coumarins from the Roots of Althaea officinalis.

PubMed

Gudej, J

1991-06-01

From the roots of ALTHAEA OFFICINALIS two flavonoid glycosides were separated. Phenolic acids and coumarins were investigated chromatographically. The structures of the compounds were established on the basis of acid hydrolysis and spectroscopic methods (UV, (1)H-NMR, (13)C-NMR) as hypolaetin 8-glucoside and the new flavonoid sulphate - isoscutellarein 4'-methyl ether 8-glucoside-2''-SO (3)K.

Uncarinic acids: phospholipase Cgamma1 inhibitors from hooks of Uncaria rhynchophylla.

PubMed

Lee, J S; Yang, M Y; Yeo, H; Kim, J; Lee, H S; Ahn, J S

1999-05-17

Bioactivity-guided fractionation of the CHCl3 extract from hooks of Uncaria rhynchophylla led to the isolation of two triterpene esters, namely uncarinic acids A (1) and B (2). Their structures were established by spectroscopic and chemical methods. These compounds inhibited phospholipase Cgamma1 with IC50 values of 35.66 and 44.55 microM, respectively.

Spectroscopic and Spectrometric Methods Used for the Screening of Certain Herbal Food Supplements Suspected of Adulteration

PubMed Central

Mateescu, Cristina; Popescu, Anca Mihaela; Radu, Gabriel Lucian; Onisei, Tatiana; Raducanu, Adina Elena

2017-01-01

Purpose: This study was carried out in order to find a reliable method for the fast detection of adulterated herbal food supplements with sexual enhancement claims. As some herbal products are advertised as "all natural", their "efficiency" is often increased by addition of active pharmaceutical ingredients such as PDE-5 inhibitors, which can be a real health threat for the consumer. Methodes: Adulterants, potentially present in 50 herbal food supplements with sexual improvement claims, were detected using 2 spectroscopic methods - Raman and Fourier Transform Infrared - known for reliability, reproductibility, and an easy sample preparation. GC-MS technique was used to confirm the potential adulterants spectra. Results: About 22% (11 out of 50 samples) of herbal food supplements with sexual enhancement claims analyzed by spectroscopic and spectrometric methods proved to be "enriched" with active pharmaceutical compounds such as: sildenafil and two of its analogues, tadalafil and phenolphthalein. The occurence of phenolphthalein could be the reason for the non-relevant results obtained by FTIR method in some samples. 91% of the adulterated herbal food supplements were originating from China. Conclusion: The results of this screening highlighted the necessity for an accurate analysis of all alleged herbal aphrodisiacs on the Romanian market. This is a first such a screening analysis carried out on herbal food supplements with sexual enhancement claims. PMID:28761827

Spectroscopic and Spectrometric Methods Used for the Screening of Certain Herbal Food Supplements Suspected of Adulteration.

PubMed

Mateescu, Cristina; Popescu, Anca Mihaela; Radu, Gabriel Lucian; Onisei, Tatiana; Raducanu, Adina Elena

2017-06-01

Purpose: This study was carried out in order to find a reliable method for the fast detection of adulterated herbal food supplements with sexual enhancement claims. As some herbal products are advertised as "all natural", their "efficiency" is often increased by addition of active pharmaceutical ingredients such as PDE-5 inhibitors, which can be a real health threat for the consumer. Methodes: Adulterants, potentially present in 50 herbal food supplements with sexual improvement claims, were detected using 2 spectroscopic methods - Raman and Fourier Transform Infrared - known for reliability, reproductibility, and an easy sample preparation. GC-MS technique was used to confirm the potential adulterants spectra. Results: About 22% (11 out of 50 samples) of herbal food supplements with sexual enhancement claims analyzed by spectroscopic and spectrometric methods proved to be "enriched" with active pharmaceutical compounds such as: sildenafil and two of its analogues, tadalafil and phenolphthalein. The occurence of phenolphthalein could be the reason for the non-relevant results obtained by FTIR method in some samples. 91% of the adulterated herbal food supplements were originating from China. Conclusion: The results of this screening highlighted the necessity for an accurate analysis of all alleged herbal aphrodisiacs on the Romanian market. This is a first such a screening analysis carried out on herbal food supplements with sexual enhancement claims.

Semi-synthesis of dihydrochalcone derivatives and their in vitro antimicrobial activities.

PubMed

Awouafack, Maurice D; Kusari, Souvik; Lamshöft, Marc; Ngamga, Dieudonne; Tane, Pierre; Spiteller, Michael

2010-04-01

We describe the semi-synthesis of dihydrochalcone derivatives and their IN VITRO antimicrobial activities. These compounds were prepared by modifying two naturally occurring antimicrobial dihydrochalcones, erioschalcones A and B, reported by us earlier. The structures of the compounds were assigned on the basis of spectroscopic evidence and by comparing their physical and spectroscopic data with those reported in the literature. All the compounds were subjected to IN VITRO antimicrobial assays against a panel of pathogenic microorganisms, including gram-positive and gram-negative bacteria, and fungi. The antimicrobial efficacies of this class of compounds were established by correlating the activity profile of each compound with its structure and by comparing the activities of all the compounds with each other based on their structure. This should enable the development of other derivatives of the dihydrochalcone family that would serve as more potent antimicrobial agents against specific pathogens. Georg Thieme Verlag KG Stuttgart.New York.

Viscosity-active D-π-A chromophores derived from benzo[b]thiophen-3(2H)-one 1,1-dioxide (BTD): Synthesis, photophysical, and NLO properties.

PubMed

Bhagwat, Archana A; Mohbiya, Dhanraj R; Avhad, Kiran C; Sekar, Nagaiyan

2018-10-05

Donor-π-Acceptor (D-π-A) compounds comprising of benzo[b]thiophen-3(2H)-one 1,1-dioxide (BTD) as acceptor with dibenzofuran, carbazole, triphenylamine, and N-methyl diphenylamine moieties as donors were synthesized for aggregation, viscosity induced emission enhancement and nonlinear optical studies. Compounds 3a-3d exhibited solid state emission. The compounds 3a-3d are viscosity sensitive in a solution of MeOH: PEG-400 and showed 10, 23, 14, and 25 fold viscosity induced enhanced emission. The compounds 3a, 3c, and 3d are aggregation-induced emission enhancement (AIEE) active while 3b quenches the fluorescence on aggregation. The quantum yield of 3a, 3c, and 3d in acetonitrile are 0.041, 0.002 and 0.002 which are enhanced in the aggregate state to 0.31, 0.009, and 0.22 respectively. Solvent-dependent parameters like dipole moment (μ), static polarizability (α), and hyperpolarizability (β and γ) were determined spectroscopically and using Density Functional Theory (DFT) calculations. First and second order hyperpolarizability increase as donor strength increases and the trend is found as 3a < 3b < 3c < 3d. Two-photon absorption (2PA) cross sections were calculated by the spectroscopic method, and large 2PA was observed 484.39 GM for compound 3c. Copyright © 2017. Published by Elsevier B.V.

Synthesis, characterization, spectroscopic properties and DFT study of a new pyridazinone family

NASA Astrophysics Data System (ADS)

Arrue, Lily; Rey, Marina; Rubilar-Hernandez, Carlos; Correa, Sebastian; Molins, Elies; Norambuena, Lorena; Zarate, Ximena; Schott, Eduardo

2017-11-01

Nitrogen compounds are widely investigated due to their pharmacological properties such as antihypertensive, antinociceptive, antibacterial, antifungal, analgesic, anticancer and inhibition activities and lately even as pesticide. In this context, we present the synthesis of new compounds: (E)-6-(3,4-dimethoxyphenyl)-3-(3-(3,4-dimethoxyphenyl)acryloyl)-1-(4-R-phenyl)- 5,6-dihydropyridazin-4(1H)-one (with R = sbnd H(1), -Cl(2), -Br(3), sbnd I(4) and sbnd COOH(5)) that was carried out by reaction of (1E, 6E)-1,7-bis(3,4-dimethoxyphenyl)hepta-1,6-diene-3,5-dione with a substituted phenylamine with general formula p-R-C6H4sbnd NH2 (R = sbnd H (1), sbnd Cl (2), -Br(3), sbnd I(4) and sbnd COOH(5)). This is the first synthesis report of a pyridazinone using as precursors a curcuminoid derivative and a diazonium salt formed in situ. All compounds were characterized by EA, FT-IR, UV-Vis, Emission,1H- and13C-NMR spectroscopy and the crystalline and molecular structure of 4 was solved by X-rays diffraction method. DFT and TD-DFT quantum chemical calculations were also employed to characterize the compounds and provide a rational explanation to the spectroscopic properties. To assess the biological activity of the systems, we focused on pesticide tests on compound 2, which showed an inhibitory effect in plant growth of Agrostis tenuis Higland.

Survey of conformational isomerism in (E)-2-[(4-bromophenylimino)methyl]-5-(diethylamino)phenol compound from structural and thermochemical points of view.

PubMed

Albayrak, Çiğdem; Kaştaş, Gökhan; Odabaşoğlu, Mustafa; Frank, René

2012-09-01

In this study, (E)-2-[(4-bromophenylimino)methyl]-5-(diethylamino)phenol compound was investigated by mainly focusing on conformational isomerism. For this purpose, molecular structure and spectroscopic properties of the compound were experimentally characterized by X-ray diffraction, FT-IR and UV-Vis spectroscopic techniques, and computationally by DFT method. The X-ray diffraction analysis of the compound shows the formation of two conformers (anti and eclipsed) related to the ethyl groups of the compound. The two conformers are connected to each other by non-covalent C-H⋯Br and C-H⋯π interactions. The combination of these interactions is resulted in fused R(2)(2)(10) and R(2)(4)(20) synthons which are responsible for the tape structure of crystal packing arrangement. The X-ray diffraction and FT-IR analyses also reveal the existence of enol form in the solid state. From thermochemical point of view, the computational investigation of isomerism includes three studies: the calculation of (a) the rate constants for transmission from anti or eclipsed conformations to transition state by using Eyring equation, (b) the activation energy needed for isomerism by using Arrhenius equation, (c) the equilibrium constant from anti conformer to eclipsed conformer by using the equation including the change in Gibbs free energy. The dependence of tautomerism on solvent types was studied on the basis of UV-Vis spectra recorded in different organic solvents. The results showed that the compound exists in enol form in all solvents except ethyl alcohol. Copyright © 2012 Elsevier B.V. All rights reserved.

Preparative purification of the major anti-inflammatory triterpenoid esters from Marigold (Calendula officinalis).

PubMed

Hamburger, M; Adler, S; Baumann, D; Förg, A; Weinreich, B

2003-06-01

A method for the efficient preparative purification of faradiol 3-O-laurate, palmitate and myristate, the major anti-inflammatory triterpenoid esters in the flower heads of the medicinal plant Calendula officinalis has been developed. Gram quantities of the individual compounds were obtained with 96 to 98% purity by a combination of supercritical fluid extraction (SFE), normal-phase and reversed-phase column chromatography. During the work-up of the faradiol esters, accompanying minor compounds of the triterpene ester fraction were purified and identified by spectroscopic means as maniladiol 3-O-laurate and myristate.

Penifupyrone, a new cytotoxic funicone derivative from the endophytic fungus Penicillium sp. HSZ-43.

PubMed

Chen, Ming-Jun; Fu, Yang-Wu; Zhou, Qun-Ying

2014-01-01

Penifupyrone (1), a new funicone derivative, has been isolated from the endophytic fungus Penicillium sp. HSZ-43, along with three known analogues, funicone (2), deoxyfunicone (3) and 3-O-methylfunicone (4). These structures were identified by using spectroscopic methods, including UV, MS, 1D and 2D NMR experiments. The structure of 1 was confirmed by single-crystal X-ray diffraction analysis. All the isolated compounds were evaluated for cytotoxicity against human oral epidermoid carcinoma KB cells, and compound 1 exhibited moderate cytotoxic activity with IC50 value of 4.7 μM.

[Bioactive constituents from whole herbs of Vernonia cinerea (II)].

PubMed

Zhu, Huaxu; Tang, Yuping; Min, Zhida; Gong, Zhunan

2009-11-01

To study the constituents of the whole herbs of Vernonia cinerea by bio-activity guided isolation with PC-12 model. The constituents were separated by column chromatography and the structures were elucidated by spectroscopic methods. Ten compounds were identified to be (-)-clovane-2,9-diol (1), caryolane-1,9beta-diol (2), apigenin (3), chrysoeriol (4), luteolin (5), thermopsoside (6), luteolin-7-O-beta-D-glucoside (7), quercetin(8), apigenin-4'-O-beta-D-glucoside (9), hyperin (10), beta-amyrin aceate (11), lupeol acetate (12). Compounds 1, 2, 6 and 10 were isolated from this genus for the first time.

A new bis-labdanic diterpene from the rhizomes of Alpinia pahangensis.

PubMed

Sivasothy, Yasodha; Ibrahim, Halijah; Paliany, Audra Shaleena; Alias, Siti Aisyah; Md Nor, Nurur Raudzah; Awang, Khalijah

2013-12-01

The rhizomes of Alpinia pahangensis yielded a new bis-labdanic diterpene for which the name pahangensin C (1) was proposed along with twelve known analogues (2-13). The structure of 1 was elucidated via spectroscopic methods including 1D and 2D NMR techniques and LCMS-IT-TOF analysis. Compounds 2 and 12 were isolated for the first time from the genus Alpinia. This is the second occurrence of compounds 2 and 12 in the Zingiberaceae family. Selected analogues exhibited moderate to strong inhibitory activity against Staphylococcus aureus and Bacillus cereus. Georg Thieme Verlag KG Stuttgart · New York.

Cytotoxic constituents of Achillea clavennae from Montenegro.

PubMed

Trifunović, Snezana; Vajs, Vlatka; Juranić, Zorica; Zizak, Zeljko; Tesević, Vele; Macura, Slobodan; Milosavljević, Slobodan

2006-05-01

Examination of the aerial parts of Achillea clavennae afforded eight guaianolides (1-8), three bisabolenes (9-11), four flavonols (12-15), sesamin (lignan) and isofraxidin (coumarin). The structures of the new compounds (2, 4, 5, 7 and 10) were determined by spectroscopic methods. The antiproliferative action of 2, 8, 9 and 12 were tested to HeLa, K562 and Fem-X human cancer cell lines. Guaianolides 2 (9alpha-acetoxyartecanin) and 8 (apressin) showed significant cytotoxic effects to all tested lines and inducumenone (9) exhibited a moderate activity. The most active was flavonol centaureidin (12), already known as cytotoxic compound.

Secondary metabolites produced by Sardiniella urbana, a new emerging pathogen on European hackberry.

PubMed

Cimmino, Alessio; Maddau, Lucia; Masi, Marco; Linaldeddu, Benedetto Teodoro; Evidente, Antonio

2018-05-30

In this study the production of secondary metabolites by a virulent strain of Sardiniella urbana, a recently described pathogen originally found on declining European hackberry trees in Italy, was investigated for the first time. Chemical analysis of the culture filtrate extracts led to the isolation of three well known compounds as R-(-)-mellein and (3R,4R)-and (3R,4S)-4-hydroxy melleins which were identified by spectroscopic methods (essentially NMR and ESIMS). The isolated compounds were tested for their phytotoxic, antifungal and zootoxic activities. Among them, only R-(-)-mellein was found to be active.

Flavonoids from the roots of Artocarpus heterophyllus.

PubMed

Yuan, Wen-Jun; Yuan, Jin-Bin; Peng, Jia-Bing; Ding, Yuan-Qing; Zhu, Ji-Xiao; Ren, Gang

2017-03-01

Four new flavonoids, artoheteroids A-D (1-4), together with six known ones (5-10), were isolated from the roots of Artocarpus heterophyllus. Their structures were elucidated by spectroscopic methods, including 1D and 2D NMR, UV, IR, CD, and HR-ESI-MS. All isolated compounds were screened for their inhibitory abilities against cathepsin K (CatK). Among them, compounds 1-2, 4-6, and 10 were found to have suppression capabilities against CatK with IC 50 values ranging from 1.4 to 93.9μM. Copyright © 2017 Elsevier B.V. All rights reserved.

Klymollins A-H, bioactive eunicellin-based diterpenoids from the formosan soft coral Klyxum molle.

PubMed

Hsu, Fang-Jung; Chen, Bo-Wei; Wen, Zhi-Hong; Huang, Chiung-Yao; Dai, Chang-Feng; Su, Jui-Hsin; Wu, Yang-Chang; Sheu, Jyh-Horng

2011-11-28

Eight new eunicellin-based diterpenoids, klymollins A-H (1-8), were isolated during the chemical investigation of the soft coral Klyxum molle from Taiwan waters. Their structures were elucidated by extensive spectroscopic analysis. The absolute configuration of 4 was determined by Mosher's method. Bioassays of the new metabolites showed that compounds 3-8 displayed significant in vitro anti-inflammatory activity by inhibiting the expression of the iNOS protein, and compounds 3, 4, and 6-8 also could effectively reduce the accumulation of COX-2 protein in LPS-stimulated RAW264.7 macrophage cells.

Cochlearoids F-K: Phenolic meroterpenoids from the fungus Ganoderma cochlear and their renoprotective activity.

PubMed

Wang, Xin-Long; Zhou, Feng-Jiao; Dou, Man; Yan, Yong-Ming; Wang, Shu-Mei; Di, Lei; Cheng, Yong-Xian

2016-11-15

Ganoderma mushrooms are of great nutritious and medicinal values. This study was designed to characterize compounds from the fruiting bodies of Ganoderma cochlear and investigate their protective effects against kidney disorders. Six novel meroterpenoids cochlearoids F-K (1-6) were isolated by utilizing phytochemical approaches. Their structures were identified on the basis of extensive spectroscopic data and calculation methods. Biological evaluation shows that compounds 1-4 and 6 exhibit potent inhibitory activity on fibronectin overproduction in TGF-β1-induced HKC-8 cells. Copyright © 2016 Elsevier Ltd. All rights reserved.

Diphenyl ethers from a marine-derived isolate of Aspergillus sp. CUGB-F046.

PubMed

Xu, Xiuli; Yang, Haijin; Xu, Huitao; Yin, Liyuan; Chen, Zhengkun; Shen, Huihui

2018-04-01

One new diphenyl ether, diorcinol K (1), along with three known compounds, diorcinols D (2), F (3) and I (4) were isolated from the fermentation media of a marine-derived fungus Aspergillus sp. CUGB-F046 which was isolated from a sediment sample collected from the Bohai Sea, China. Their structures were elucidated by detailed spectroscopic methods. Compounds 1, 2 and 4 displayed significant antibacterial activities against Staphylococcus aureus and methicillin-resistant S. aureus with MIC values of 3.125, 6.25 and 6.25 μg/mL, respectively.

Streptothricin derivatives from Streptomyces sp. I08A 1776.

PubMed

Gan, Maoluo; Zheng, Xudong; Gan, Lishe; Guan, Yan; Hao, Xueqin; Liu, Yishuang; Si, Shuyi; Zhang, Yuqin; Yu, Liyan; Xiao, Chunling

2011-05-27

Five new streptothricin derivatives with a carbamoyl group substituted at C-12 (1-5) and three known analogues have been isolated from the culture broth of Streptomyces sp. I08A 1776 by ion exchange and hydrophilic interaction chromatographic techniques. Their structures were determined by spectroscopic and chemical methods. Compound 3 was a streptothricin derivative possessing a cis-streptolidine moiety. Its absolute configuration was defined by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Compound 5 and streptothricin E (6) displayed antibacterial and antifungal activity with MIC values in the range 1-64 μg/mL.

Pyriculins A and B, two monosubstituted hex-4-ene-2,3-diols and other phytotoxic metabolites produced by Pyricularia grisea isolated from buffelgrass (Cenchrus ciliaris).

PubMed

Masi, Marco; Meyer, Susan; Górecki, Marcin; Mandoli, Alessandro; Di Bari, Lorenzo; Pescitelli, Gennaro; Cimmino, Alessio; Cristofaro, Massimo; Clement, Suzette; Evidente, Antonio

2017-11-01

Pyricularia grisea has been identified as a foliar pathogen on buffelgrass (Cenchrus ciliaris) in North America and was studied as a potential source of phytotoxins for buffelgrass control. Two monosubstituted hex-4-ene-2,3-diols, named pyriculins A and B, were isolated from its culture filtrate organic extract together with (10S,11S)-(-)-epipyriculol, trans-3,4-dihydro-3,4,8-trihydroxy-1(2H)-napthalenone, and (4S)-(+)-isosclerone. Pyriculins A and B were characterized by spectroscopic (essentially nuclear magnetic resonance [NMR], High-resolution electrospray ionization mass spectrometry [HRESIMS]) and chemical methods such as (4E)-1-(4-hydroxy-1,3-dihydroisobenzofuran-1-yl)hex-4-ene-2,3-diols. The relative and absolute configuration of these compounds was determined by a combination of spectroscopic (NMR, electronic circular dichroism [ECD]) and computational tools. When bioassayed in a buffelgrass coleoptile and radicle elongation test, (10S,11S)-(-)-epipyriculol proved to be the most toxic compound. Seed germination was much reduced and slowed with respect to the control and radicles failed to elongate. All five compounds delayed germination, but only (10S,11S)-(-)-epipyriculol was able to prevent radicle development of buffelgrass seedlings. It had no effect on coleoptile elongation, while the other four compounds caused significantly increased coleoptile development relative to the control. © 2017 Wiley Periodicals, Inc.

Synthesis, spectral characterization and computed optical analysis of potent triazole based compounds

NASA Astrophysics Data System (ADS)

Sumrra, Sajjad H.; Mushtaq, Fazila; Khalid, Muhammad; Raza, Muhammad Asam; Nazar, Muhammad Faizan; Ali, Bakhat; Braga, Ataualpa A. C.

2018-02-01

Biologically active triazole Schiff base ligand (L) and metal complexes [Fe(II), Co(II), Ni(II), Cu(II) and Zn(II)] are reported herein. The ligand acted as tridentate and coordinated towards metallic ions via azomethine-N, triazolic-N moiety and deprotonated-O of phenyl substituents in an octahedral manner. These compounds were characterized by physical, spectral and analytical analysis. The synthesized ligand and metal complexes were screened for antibacterial pathogens against Chromohalobacter salexigens, Chromohalobacter israelensi, Halomonas halofila and Halomonas salina, antifungal bioassay against Aspergillus niger and Aspergellus flavin, antioxidant (DPPH, phosphomolybdate) and also for enzyme inhibition [butyrylcholinesterase (BChE) and acetylcholinesterase (AChE)] studies. The results of these activities indicated the ligand to possess potential activity which significantly increased upon chelation. Moreover, vibrational bands, frontier molecular orbitals (FMOs) and natural bond analysis (NBO) of ligand (1) were carried out through density functional theory (DFT) with B3lYP/6-311 ++G (d,p) approach. While, UV-Vis analysis was performed by time dependent TD-DFT with B3lYP/6-311 ++G (d,p) method. NBO analysis revealed that investigated compound (L) contains enormous molecular stability owing to hyper conjugative interactions. Theoretical spectroscopic findings showed good agreement to experimental spectroscopic data. Global reactivity descriptors were calculated using the energies of FMOs which indicated compound (L) might be bioactive. These parameters confirmed the charge transfer phenomenon and reasonable correspondence with experimental bioactivity results.

Crystal structure, spectroscopic studies and quantum mechanical calculations of 2-[((3-iodo-4-methyl)phenylimino)methyl]-5-nitrothiophene.

PubMed

Özdemir Tarı, Gonca; Gümüş, Sümeyye; Ağar, Erbil

2015-04-15

The title compound, 2-[((3-iodo-4-methyl)phenylimino)methyl]-5-nitrothiophene, C12H9O2N2I1S1, was synthesized and characterized by IR, UV-Vis and single-crystal X-ray diffraction technique. The molecular structure was optimized at the B3LYP, B3PW91 and PBEPBE levels of the density functional method (DFT) with the 6-311G+(d,p) basis set. Using the TD-DFT method, the electronic absorption spectra of the title compound was computed in both the gas phase and ethanol solvent. The harmonic vibrational frequencies of the title compound were calculated using the same methods with the 6-311G+(d,p) basis set. The calculated results were compared with the experimental determination results of the compound. The energetic behavior such as the total energy, atomic charges, dipole moment of the title compound in solvent media were examined using the B3LYP, B3PW91 and PBEPBE methods with the 6-311G+(d,p) basis set by applying the Onsager and the polarizable continuum model (PCM). The molecular orbitals (FMOs) analysis, the molecular electrostatic potential map (MEP) and the nonlinear optical properties (NLO) for the title compound were obtained with the same levels of theory. And then thermodynamic properties for the title compound were obtained using the same methods with the 6-311G(d,p) basis set. Copyright © 2015 Elsevier B.V. All rights reserved.

Isoprene derivatives from the leaves and callus cultures of Vaccinium corymbosum var. bluecrop.

PubMed

Migas, Piotr; Cisowski, Wojciech; Dembińska-Migas, Wanda

2005-01-01

The phytochemical analysis of Vaccinium corymbosum var bluecrop leaves and callus biomass revealed ursolic acid, oleanolic acid, alpha-amyrin and beta-amyrin in both plant materials. Beta-sitosterol was determined only in callus biomass. The structure of isolated compounds was elucidated by TLC co-chromatography with standards and with spectroscopic methods (1H NMR, 13C NMR, EI-MS).

Quantum mechanical and spectroscopic (FT-IR, 13C, 1H NMR and UV) investigations of 2-(5-(4-Chlorophenyl)-3-(pyridin-2-yl)-4,5-dihydropyrazol-1-yl)benzo[d]thiazole by DFT method

NASA Astrophysics Data System (ADS)

Diwaker

2014-07-01

The electronic, NMR, vibrational, structural properties of a new pyrazoline derivative: 2-(5-(4-Chlorophenyl)-3-(pyridine-2-yl)-4,5-dihydropyrazol-1-yl)benzo[d]thiazole has been studied using Gaussian 09 software package. Using VEDA 4 program we have reported the PED potential energy distribution of normal mode of vibrations of the title compound. We have also reported the 1H and 13C NMR chemical shifts of the title compound using B3LYP level of theory with 6-311++G(2d,2p) basis set. Using time dependent (TD-DFT) approach electronic properties such as HOMO and LUMO energies, electronic spectrum of the title compound has been studied and reported. NBO analysis and MEP surface mapping has also been calculated and reported using ab initio methods.

The study on molecular structure and microbiological activity of alkali metal 3-hydroxyphenylycetates

NASA Astrophysics Data System (ADS)

Samsonowicz, M.; Regulska, E.; Kowczyk-Sadowy, M.; Butarewicz, A.; Lewandowski, W.

2017-10-01

The biological activity of chemical compounds depends on their molecular structure. In this paper molecular structure of 3-hydroxyphenylacetates in comparison to 3-hydroxyphenylacetic acid was studied. FT-IR, FT-Raman and NMR spectroscopy and density functional theory (DFT) calculations was used. The B3LYP/6-311++G(d,p) hybrid functional method was used to calculate optimized geometrical structures of studied compounds. The Mulliken, APT, MK, ChelpG and NBO atomic charges as well as dipole moment and energy values were calculated. Theoretical chemical shifts in NMR spectra and the wavenumbers and intensities of the bands in vibrational spectra were analyzed. Calculated parameters were compared to experimental characteristic of studied compounds. Microbiological analysis of studied compounds was performed relative to: Bacillus subtilis, Pseudomonas aeruginosa, Escherichia coli and Klebsiella oxytoca. The relationship between spectroscopic and structure parameters of studied compounds in regard to their activity was analyzed.

New Benzophenones and Xanthones from Cratoxylum sumatranum ssp. neriifolium and Their Antibacterial and Antioxidant Activities.

PubMed

Tantapakul, Cholpisut; Maneerat, Wisanu; Sripisut, Tawanun; Ritthiwigrom, Thunwadee; Andersen, Raymond J; Cheng, Ping; Cheenpracha, Sarot; Raksat, Achara; Laphookhieo, Surat

2016-11-23

Two new benzophenones (1 and 2) and four new xanthones (4-6 and 17) together with 24 known compounds (3, 7-16, and 18-30) were isolated from the roots and twigs of Cratoxylum sumatranum ssp. neriifolium. Their structures were elucidated by spectroscopic methods. Compounds 5 and 26 showed antibacterial activity against Micrococcus luteus, Bacillus cereus, and Staphylococcus epidermis with minimum inhibitory concentrations ranging from 4 to 8 μg/mL, whereas compounds 7, 20, and 26 displayed selective antibacterial activities against Staphylococcus aureus (8 μg/mL), Salmonella typhimurium (4 μg/mL), and Pseudomonas aeruginosa (4 μg/mL), respectively. The radical scavenging effects of some isolated compounds were investigated. Compounds 11 and 21 exhibited potent activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) with IC 50 values of 7.0 ± 1.0 and 6.0 ± 0.2 μM, respectively.

Anti-leishmanial, anti-inflammatory and antimicrobial activities of phenolic derivatives from Tibouchina paratropica.

PubMed

Tracanna, María I; Fortuna, Antonio M; Cárdenas, Angel V Contreras; Marr, Alexandra K; McMaster, W Robert; Gómez-Velasco, Anaximandro; Sánchez-Arreola, Eugenio; Hernández, Luis Ricardo; Bach, Horacio

2015-03-01

A new phenolic derivative, 2,8-dihydroxy-7H-furo[2,3-f]chromen-7-one (1), together with isoquercitrin (2), was isolated from the aerial parts of Tibouchina paratropica. Compound structures were elucidated by spectroscopic methods. Both compounds show antimicrobial activity towards a panel of bacterial and fungal pathogens, and compound 1 displayed potent anti-parasitic activity against Leishmania donovani (IC50  = 0.809 µg/mL). In addition, an 85% reduction in the secretion of the pro-inflammatory cytokine IL-6 was recorded when macrophages challenged with lipopolysaccharide were exposed to compound 1, but no effect on the anti-inflammatory IL-10 was observed. Compound 2 showed neither anti-parasitic nor anti-inflammatory properties. In addition, no cytotoxic activities were observed against the human-derived macrophage THP-1 cells. Copyright © 2014 John Wiley & Sons, Ltd.

Neuroprotective Compound from an Endophytic Fungus, Colletotrichum sp. JS-0367.

PubMed

Song, Ji Hoon; Lee, Changyeol; Lee, Dahae; Kim, Soonok; Bang, Sunghee; Shin, Myoung-Sook; Lee, Jun; Kang, Ki Sung; Shim, Sang Hee

2018-05-23

Colletotrichum sp. JS-0367 was isolated from Morus alba (mulberry), identified, and cultured on a large scale for chemical investigation. One new anthraquinone (1) and three known anthraquinones (2-4) were isolated and identified using spectroscopic methods including 1D/2D-NMR and HRESIMS. Although the neuroprotective effects of some anthraquinones have been reported, the biological activities of the four anthraquinones isolated in this study have not been reported. Therefore, the neuroprotective effects of these compounds were determined against murine hippocampal HT22 cell death induced by glutamate. Compound 4, evariquinone, showed strong protective effects against HT22 cell death induced by glutamate by the inhibition of intracellular ROS accumulation and Ca 2+ influx triggered by glutamate. Immunoblot analysis revealed that compound 4 reduced the phosphorylation of MAPKs (JNK, ERK1/2, and p38) induced by glutamate. Furthermore, compound 4 strongly attenuated glutamate-mediated apoptotic cell death.

SOD activity and DNA binding properties of a new symmetric porphyrin Schiff base ligand and its metal complexes.

PubMed

Çay, Sevim; Köse, Muhammet; Tümer, Ferhan; Gölcü, Ayşegül; Tümer, Mehmet

2015-12-05

4-Methoxy-2,6-bis(hydroxymethyl)phenol (1) was prepared from the reaction of 4-methoxyphenol and formaldehyde. The compound (1) was then oxidized to the 4-methoxy-2,6-diformylphenol (2) compound. Molecular structure of compound (2) was determined by X-ray diffraction method. A new symmetric porphyrin Schiff base ligand 4-methoxy-2,6-bis[5-(4-iminophenyl)-10,15,20-triphenylporphyrin]phenol (L) was prepared from the reaction of the 5-(4-aminophenyl)-10,15,20-triphenylporphyrin (TTP-NH2) and the compound (2) in the toluene solution. The metal complexes (Cu(II), Fe(III), Mn(III), Pt(II) and Zn(II)) of the ligand (L) were synthesized and characterized by the spectroscopic and analytical methods. The DNA (fish sperm FSdsDNA) binding studies of the ligand and its complexes were performed using UV-vis spectroscopy. Additionally, superoxide dismutase activities of the porphyrin Schiff base metal complexes were investigated. Additionally, electrochemical, photoluminescence and thermal properties of the compounds were investigated. Copyright © 2015 Elsevier B.V. All rights reserved.

Spectroscopic and quantum-mechanical study of enol-enol tautomerism of 3-acetyltetramic acid derivatives

NASA Astrophysics Data System (ADS)

Gromak, V. V.; Avakyan, V. G.; Lakhvich, O. F.

2000-03-01

By the method of IR spectroscopy, Raman spectroscopy, and nonempirical (basis 3-21G//3-21G(d,p)) and semiempirical (approximations AM1 and PM3) quantum-mechanical methods the tautomeric structure of a series of 3-acetyltetramic acid derivatives has been investigated. It is shown that all the investigated compounds exist in vapor, in solution, and in the crystalline state mainly in the form of exo-enols among which the prevalent form is that in which lactam carbonyl participates in intrachelate hydrogen bonding. Complete series of relative stabilities of possible tautomeric forms of the investigated compounds have been established. General conlusions on the structure of 5-membered ring β,β'-triketones have been formulated.

Ethylenediammonium dication: H-bonded complexes with terephthalate, chloroacetate, phosphite, selenite and sulfamate anions. Detailed vibrational spectroscopic and theoretical studies of ethylenediammonium terephthalate

NASA Astrophysics Data System (ADS)

Marchewka, M. K.; Drozd, M.

2012-12-01

Crystalline complexes between ethylenediammonium dication and terephthalate, chloroacetate, phosphite, selenite and sulfamate anions were obtained by slow evaporation from water solution method. Room temperature powder infrared and Raman measurements were carried out. For ethylenediammonium terephthalate theoretical calculations of structure were performed by two ways: ab-initio HF and semiempirical PM3. In this case the PM3 method gave more accurate structure (closer to X-ray results). The additional PM3 calculations of vibrational spectra were performed. On the basis theoretical approach and earlier vibrational studies of similar compounds the vibrational assignments for observed bands have been proposed. All compounds were checked for second harmonic generation (SHG).

Synthesis, spectroscopic characterization and quantum chemical computational studies of (S)-N-benzyl-1-phenyl-5-(pyridin-2-yl)-pent-4-yn-2-amine

NASA Astrophysics Data System (ADS)

Kose, Etem; Atac, Ahmet; Karabacak, Mehmet; Karaca, Caglar; Eskici, Mustafa; Karanfil, Abdullah

2012-11-01

The synthesis and characterization of a novel compound (S)-N-benzyl-1-phenyl-5-(pyridin-2-yl)-pent-4-yn-2-amine (abbreviated as BPPPYA) was presented in this study. The spectroscopic properties of the compound were investigated by FT-IR, NMR and UV spectroscopy experimentally and theoretically. The molecular geometry and vibrational frequencies of the BPPPYA in the ground state were calculated by using density functional theory (DFT) B3LYP method invoking 6-311++G(d,p) basis set. The geometry of the BPPPYA was fully optimized, vibrational spectra were calculated and fundamental vibrations were assigned on the basis of the total energy distribution (TED) of the vibrational modes, calculated with scaled quantum mechanics (SQM) method and PQS program. The results of the energy and oscillator strength calculated by time-dependent density functional theory (TD-DFT) and CIS approach complement with the experimental findings. Total and partial density of state (TDOS and PDOS) and also overlap population density of state (COOP or OPDOS) diagrams analysis were presented. The theoretical NMR chemical shifts (1H and 13C) complement with experimentally measured ones. The dipole moment, linear polarizability and first hyperpolarizability values were also computed. The linear polarizabilities and first hyper polarizabilities of the studied molecule indicate that the compound is a good candidate of nonlinear optical materials. The calculated vibrational wavenumbers, absorption wavelengths and chemical shifts showed the best agreement with the experimental results.

A novel series of thiosemicarbazone drugs: From synthesis to structure

NASA Astrophysics Data System (ADS)

Ebrahimi, Hossein Pasha; Hadi, Jabbar S.; Alsalim, Tahseen A.; Ghali, Thaer S.; Bolandnazar, Zeinab

2015-02-01

A new series of thiosemicarbazones (TSCs) and their 1,3,4-thiadiazolines (TDZs) containing acetamide group have been synthesized from thiosemicarbazide compounds by the reaction of TSCs with cyclic ketones as well as aromatic aldehydes. The structures of newly synthesized 1,3,4-thiadiazole derivatives obtained by heterocyclization of the TSCs with acetic anhydride were experimentally characterized by spectral methods using IR, 1H NMR, 13C NMR and mass spectroscopic methods. Furthermore, the structural, thermodynamic, and electronic properties of the studied compounds were also studied theoretically by performing Density Functional Theory (DFT) to access reliable results to the experimental values. The molecular geometry, the highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) and Mulliken atomic charges of the studied compounds have been calculated at the B3LYP method and standard 6-31+G(d,p) basis set starting from optimized geometry. The theoretical 13C chemical shift results were also calculated using the gauge independent atomic orbital (GIAO) approach and their respective linear correlations were obtained.

A new alkaloid from the fruit of Nandina domestica Thunb.

PubMed

Peng, Cai-Ying; Liu, Jian-Qun; Zhang, Rui; Shu, Ji-Cheng

2014-01-01

A new steroidal alkaloid, (20S,22R,24R)-24-ethyl-3-oxocholest-4-en-22-amino, named as nandsterine (1), together with 10 known alkaloids, palmatine (2), O-methylbulbocapnine (3), nantenine (4), dehydronantenine (5), glaucine (6), didehydroglaucine (7), dehydrocorydaline (8), jatrorrhizine (9), magnoflorine (10) and berberine (11), was isolated from the fruit of Nandina domestica Thunb. Their structures were elucidated by using spectroscopic methods as well as by comparing with the published data. Compound 1 was a new class of steroidal alkaloid isolated from the family Berberidaceae, meanwhile compounds 2, 3, 6-8 and 10 were obtained from N. domestica for the first time. Compound 1 exhibited cytotoxicity against HL-60 cells (human leukaemia) with IC50 values of 52.1 μM.

New analogues of brefeldin A from sediment-derived fungus Penicillium sp. DT-F29.

PubMed

Hu, Zhi-Fei; Qin, Le-Le; Ding, Wan-Jing; Liu, Yu; Ma, Zhong-Jun

2016-10-01

Four new analogues of brefeldin A named 7, 7-dimethoxybrefeldin C (3), 6β-hydroxybrefeldin C (4), 4-epi-15-epi-brefeldin A (5), 4-epi-8α-hydroxy-15-epi-brefeldin C (6), together with four known analogues (1, 7-9) were isolated from a fermentation of the sediment-derived fungus Penicillium sp. DT-F29. The structures of these compounds were elucidated on the basis of extensive spectroscopic and chemical methods. In the bioactivity assays, only compounds 1 and 8 showed significant inhibitory activities against human lung adenocarcinoma cell. In addition, compound 1 was first reported for the potent ability to reactivate latent HIV with EC50 value of 0.03 μM.

In vitro antiplasmodial and cytotoxic activities of sesquiterpene lactones from Vernonia fimbrillifera Less. (Asteraceae).

PubMed

Bordignon, Annélise; Frédérich, Michel; Ledoux, Allison; Campos, Pierre-Eric; Clerc, Patricia; Hermann, Thomas; Quetin-Leclercq, Joëlle; Cieckiewicz, Ewa

2018-06-01

Due to the in vitro antiplasmodial activity of leaf extracts from Vernonia fimbrillifera Less. (Asteraceae), a bioactivity-guided fractionation was carried out. Three sesquiterpene lactones were isolated, namely 8-(4'-hydroxymethacrylate)-dehydromelitensin (1), onopordopicrin (2) and 8α-[4'-hydroxymethacryloyloxy]-4-epi-sonchucarpolide (3). Their structures were elucidated by spectroscopic methods (1D and 2D NMR and MS analyses) and by comparison with published data. The isolated compounds exhibited antiplasmodial activity with IC 50 values ≤ 5 μg/mL. Cytotoxicity of the compounds against a human cancer cell line (HeLa) and a mouse lung epithelial cell line (MLE12) was assessed to determine selectivity. Compound 3 displayed promising selective antiplasmodial activity (SI > 10).

Antimicrobial activity and molecular docking studies of a novel anthraquinone from a marine-derived fungus Aspergillus versicolor.

PubMed

Wang, Weiyi; Chen, Ruixuan; Luo, Zhuhua; Wang, Wei; Chen, Jianming

2018-03-01

A novel anthraquinone, 2-(dimethoxymethyl)-1-hydroxyanthracene-9,10-dione (1), together with nine known compounds (2-10), were isolated from the fermentation of Aspergillus versicolor derived from deep sea sediment. Their structures were established through spectroscopic methods. Compound 1 exhibited strong inhibitory activities against MRSA ATCC 43300 and MRSA CGMCC 1.12409 (with MIC values of 3.9 and 7.8 μg/mL respectively) and moderate activities against tested strains of Vibrio (with MIC values ranging from 15.6 to 62.5 μg/mL). Compound 1 was subjected to molecular docking studies for inhibition of topoisomerase IV and AmpC β-lactamase enzymes indicating its usefulness as antimicrobial agent.

Cytotoxic and Anti-HIV Phenanthroindolizidine Alkaloids from Cryptocarya chinensis

PubMed Central

Wu, Tian-Shung; Su, Chung-Ren; Lee, Kuo-Hsiung

2013-01-01

Bioassay-guided fractionation of the cytotoxic ethanol extract of Cryptocarya chinensis has led to the isolation of 11 compounds, including two phenanthroindolizidine alkaloids [(−)-antofine (1) and dehydroantofine (2)], five pavine alkaloids (3–7), and four proaporphine alkaloids (8–11). The structures of the isolated compounds were determined by means of NMR spectroscopic methods, and supported by HRMS and optical rotation data. Compounds 1 and 2 showed cytotoxic activity against four cancer cell lines, L1210, P388, A549, and HCT-8, with 1 being the most potent against A549 and HCT-8 with EC50 values of 0.002 and 0.001 μg/mL, respectively. In addition, 2 is first reported to exhibit significant anti-HIV activity. PMID:22816292

Bioactive components from the heartwood of Pterocarpus santalinus.

PubMed

Wu, Shou-Fang; Hwang, Tsong-Long; Chen, Shu-Li; Wu, Chin-Chung; Ohkoshi, Emika; Lee, Kuo-Hsiung; Chang, Fang-Rong; Wu, Yang-Chang

2011-09-15

One new phenanthrenedione, pterolinus K (1), and one new chalcone, pterolinus L (2) were isolated from the heartwood extract of Pterocarpus santalinus. The structures were elucidated by spectroscopic methods. Both 1 and 2 showed inhibitory effect on elastase release by human neutrophils in response to fMLP with an IC(50) value of 4.24 and 0.95 μM, and compound 1 also inhibited superoxide anion generation with IC(50) value of 0.99 μM. In addition, compound 1 showed selective cytotoxicity against HepG2 with IC(50) value of 10.86 μM, while compound 2 showed a moderate cytotoxicity against KB with IC(50) values of 17.18 μM. Copyright © 2011 Elsevier Ltd. All rights reserved.

Design, synthesis, molecular docking, anti-Proteus mirabilis and urease inhibition of new fluoroquinolone carboxylic acid derivatives.

PubMed

Abdullah, Mohammed A A; Abuo-Rahma, Gamal El-Din A A; Abdelhafez, El-Shimaa M N; Hassan, Heba A; Abd El-Baky, Rehab M

2017-02-01

New hydroxamic acid, hydrazide and amide derivatives of ciprofloxacin in addition to their analogues of levofloxacin were prepared and identified by different spectroscopic techniques. Some of the prepared compounds revealed good activity against the urease splitting bacteria, Proteus mirabilis. The urease inhibitory activity was investigated using indophenol method. Most of the tested compounds showed better activity than the reference acetohydroxamic acid (AHA). The ciprofloxacin hydrazide derivative 3a and levofloxacin hydroxamic acid 7 experienced the highest activity (IC 50 =1.22μM and 2.20μM, respectively). Molecular docking study revealed high spontaneous binding ability of the tested compounds to the active site of urease. Copyright © 2016 Elsevier Inc. All rights reserved.

Five new lactone derivatives from the stems of Dendrobium nobile.

PubMed

Zhou, Xue-Ming; Zheng, Cai-Juan; Wu, Jia-Ting; Chen, Guang-Ying; Chen, Jun; Sun, Chong-Ge

2016-12-01

Five new lactone derivatives decumbic acids A and B (1 and 2), (-)-decumbic acid (3a), (-)- and (+)-dendrolactone (4a and 4b) together with four known compounds (3b and 5-7) were isolated from the stems of Dendrobium nobile. Their structures were elucidated using comprehensive spectroscopic methods. Compounds 3a and 3b, 4a and 4b were isolated as two pair of enantiomers by chiral HPLC. The absolute configurations of 1, 2, 3a, 4a and 4b were determined by optical rotation and X-ray crystallographic analysis. The inhibitory activities of all compounds against nine phytopathogenic fungi and three cancer cell lines were evaluated. Copyright © 2016 Elsevier B.V. All rights reserved.

Synthesis and spectroscopic properties of some new difluoroboron bis-β-diketonate derivatives.

PubMed

Pi, Yan; Wang, Dun-Jia; Liu, Hua; Hu, Yan-Jun; Wei, Xian-Hong; Zheng, Jing

2014-10-15

Six new bis-β-diketones (RCOCH2CO-C7H7N-COCH2COR) were synthesized from 3,5-diacetyl-2,6-dimethylpyridine via Claisen condensation with the corresponding esters, and then reacted with boron trifluoride etherate to afford difluoroboron bis-β-diketonate derivatives. Their spectroscopic properties were investigated by UV-vis, FTIR, (1)H NMR and fluorescence spectroscopic techniques. It was found that these boron complexes exhibited violet or blue fluorescence emission at 422-445nm and possessed high extinction coefficients. The results indicate that the extending π-conjugation can increase the fluorescence intensity and quantum yield for these boron complexes. Especially, the compound 2b displayed the stronger fluorescence intensity and the highest fluorescence quantum yield (Φu=0.94) in these boron compounds. However, compounds 2c and 2d had the lower fluorescence intensity and quantum yield as a result of the heavy atom effect of the chlorine atom in the molecules. Copyright © 2014 Elsevier B.V. All rights reserved.

Synthesis and spectroscopic properties of some new difluoroboron bis-β-diketonate derivatives

NASA Astrophysics Data System (ADS)

Pi, Yan; Wang, Dun-Jia; Liu, Hua; Hu, Yan-Jun; Wei, Xian-Hong; Zheng, Jing

2014-10-01

Six new bis-β-diketones (RCOCH2CO-C7H7N-COCH2COR) were synthesized from 3,5-diacetyl-2,6-dimethylpyridine via Claisen condensation with the corresponding esters, and then reacted with boron trifluoride etherate to afford difluoroboron bis-β-diketonate derivatives. Their spectroscopic properties were investigated by UV-vis, FTIR, 1H NMR and fluorescence spectroscopic techniques. It was found that these boron complexes exhibited violet or blue fluorescence emission at 422-445 nm and possessed high extinction coefficients. The results indicate that the extending π-conjugation can increase the fluorescence intensity and quantum yield for these boron complexes. Especially, the compound 2b displayed the stronger fluorescence intensity and the highest fluorescence quantum yield (Φu = 0.94) in these boron compounds. However, compounds 2c and 2d had the lower fluorescence intensity and quantum yield as a result of the heavy atom effect of the chlorine atom in the molecules.

Synthesis, characterization and spectroscopic behavior of novel 2-oxo-1,4-disubstituted-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile dyes.

PubMed

Khan, Salman A; Asiri, Abdullah M; Al-Thaqafy, Saad H; Faidallah, Hassan M; El-Daly, Samy A

2014-12-10

Two synthetic pathways were adopted to synthesize the target 2-oxo-1,4-disubstituted-1,2,5,6-tetrahydro-benzo[h]quinoline-3-carbonitriles. Structure of the synthesized compounds has been characterized based on FT-IR, (1)H NMR, (13)C NMR and elemental analyses. UV-Vis and fluorescence spectroscopy measurements provided that all compounds are good absorbent and fluorescent. Fluorescence polarity study demonstrated that these compounds were sensitive to the polarity of the microenvironment provided by different solvents. In addition, spectroscopic and physicochemical parameters, including singlet absorption, extinction coefficient, Stokes shift, oscillator strength and dipole moment were investigated in order to explore the analytical potential of synthesized compounds. Copyright © 2014 Elsevier B.V. All rights reserved.

Synthesis, spectroscopic characterization and structural investigations of new adduct compound of carbazole with picric acid: DNA binding and antimicrobial studies

NASA Astrophysics Data System (ADS)

Saravanabhavan, Munusamy; Sathya, Krishnan; Puranik, Vedavati G.; Sekar, Marimuthu

2014-01-01

Carbazole picrate (CP), a new organic compound has been synthesized, characterized by various analytical and spectroscopic technique such as FT-IR, UV-Vis, 1H and 13C NMR spectroscopy. An orthorhombic geometry was proposed based on single crystal XRD study. The thermal stability of the crystal was studied by using thermo-gravimetric and differential thermal analyses and found that it was stable up to 170 °C. Further, the newly synthesized title compound was tested for its in vitro antibacterial and antifungal activity against various bacterial and fungal species. Also, the compound was tested for its binding activity with Calf thymus (CT) DNA and the results show a considerable interaction between CP and CT-DNA.

Antiviral flavonoids from the seeds of Aesculus chinensis.

PubMed

Wei, Feng; Ma, Shuang-Cheng; Ma, Lin-Yun; But, Paul Pui-Hay; Lin, Rui-Chao; Khan, Ikhlas A

2004-04-01

A bioassay-guided fractionation of an ethanol extract of the seeds of Aesculus chinensis led to the isolation of two new flavanoids (1 and 2), along with eight known ones (3-10). The structures of the new compounds were elucidated by spectroscopic methods including 2D NMR. All compounds were tested for antiviral activity against respiratory syncytial virus (RSV), parainfluenza virus type 3 (PIV 3), and influenza virus type A (Flu A). Compounds 1, 2, and 6 showed significant antiviral activities against RSV with IC(50) values of 4.5, 6.7, and 4.1 microg/mL and selective index (SI) values of 15.8, 32, and 63.8, respectively. Compound 8 demonstrated significant antiviral activity against Flu A with an IC(50) of 24.5 microg/mL and a SI of 16.0, respectively.

Synthesis, crystal structure and antimicrobial potential of some fluorinated chalcone-1,2,3-triazole conjugates.

PubMed

Yadav, Pinki; Lal, Kashmiri; Kumar, Lokesh; Kumar, Ashwani; Kumar, Anil; Paul, Avijit K; Kumar, Rajnish

2018-06-02

A simple and green synthesis of some fluorinated chalcone-triazole hybrids from propargylated chalcones and organic azides catalyzed by cellulose supported copper nanoparticles click reaction is reported. All the synthesized compounds were well characterized by various analytical and spectroscopic methods. The X-rays crystallographic study of compounds 6k revealed the self assembling properties. The antimicrobial screening results of all the synthesized compounds revealed that most of the triazole hybrids exhibited significant efficacy against tested bacterial and fungal strains. The activity results showed the synergistic effect of biological activity when two pharmacophoric units, i.e. chalcone and 1,2,3-triazole are conjugated. Further, docking simulation of the most active compounds 6p into Escherichia coli topoisomerase II DNA Gyrase B was also carried out. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

Two New Stilbenoids from the Aerial Parts of Arundina graminifolia (Orchidaceae).

PubMed

Auberon, Florence; Olatunji, Opeyemi Joshua; Krisa, Stéphanie; Antheaume, Cyril; Herbette, Gaëtan; Bonté, Frédéric; Mérillon, Jean-Michel; Lobstein, Annelise

2016-10-27

Two new phenanthrene derivatives, a phenanthrenequinone named arundiquinone ( 1 ) and a 9,10-dihydrophenanthrene named arundigramin ( 2 ) together with a known lignin dimer ( 3 ) and seven known stilbenoids ( 4 - 10 ) were isolated from the aerial parts of the Asian orchid Arundina graminifolia . The structures of the isolated compounds were elucidated by spectroscopic methods, including extensive 1D, 2D NMR (heteronuclear single quantum coherence (HSQC), heteronuclear multiple-bond correlation spectroscopy (HMBC), and HR-ESI-MS techniques, as well as comparison with respective literature reports. The cytoprotective activity of the isolated compounds were evaluated for their ability to reduce beta amyloid induced toxicity on undifferentiated PC12 cells. Compound 8 showed moderate cytoprotective activity at 0.5 µmol/L (71% of cell viability) while the other compounds showed no significant activity at the highest concentration tested.

Synthesis, structure, spectroscopic investigations, and computational studies of optically pure β-ketoamide

DOE Office of Scientific and Technical Information (OSTI.GOV)

Mtat, D.; Touati, R.; Guerfel, T., E-mail: taha-guerfel@yahoo.fr

2016-12-15

Chemical preparation, X-ray single crystal diffraction, IR and NMR spectroscopic investigations of a novel nonlinear optical organic compound (C{sub 17}H{sub 22}NO{sub 2}Cl) are described. The compound crystallizes in the orthorhombic system with the non-centrosymmetric sp. gr. P2{sub 1}2{sub 1}2{sub 1}. In the crystal structure, molecules are interconnected by N–H…O hydrogen bonds forming infinite chains along a axis. The Hirshfeld surface and associated fingerprint plots of the compound are presented to explore the nature of intermolecular interactions and their relative contributions in building the solid-state architecture. The molecular HOMO–LUMO compositions and their respective energy gaps are also drawn to explain themore » activity of the compound. The first hyperpolarizability β{sub tot} of the title compound is determined using DFT calculations. The optical properties are also investigated by UV–Vis absorption spectrum.« less

Spectroscopic analysis of phenolic compounds for food and feed formulations

USDA-ARS?s Scientific Manuscript database

Phenolic compounds exhibit several bioactive properties including anti-oxidant, anti-microbial, and anti-fungal characteristics with potential applications as additives in functional food and feed formulations. Phenolic compounds occur in plants as secondary metabolites and may be recovered as a co-...

Assessment and correction of turbidity effects on Raman observations of chemicals in aqueous solutions.

PubMed

Sinfield, Joseph V; Monwuba, Chike K

2014-01-01

Improvements in diode laser, fiber optic, and data acquisition technologies are enabling increased use of Raman spectroscopic techniques for both in lab and in situ water analysis. Aqueous media encountered in the natural environment often contain suspended solids that can interfere with spectroscopic measurements, yet removal of these solids, for example, via filtration, can have even greater adverse effects on the extent to which subsequent measurements are representative of actual field conditions. In this context, this study focuses on evaluation of turbidity effects on Raman spectroscopic measurements of two common environmental pollutants in aqueous solution: ammonium nitrate and trichloroethylene. The former is typically encountered in the runoff from agricultural operations and is a strong scatterer that has no significant influence on the Raman spectrum of water. The latter is a commonly encountered pollutant at contaminated sites associated with degreasing and cleaning operations and is a weak scatterer that has a significant influence on the Raman spectrum of water. Raman observations of each compound in aqueous solutions of varying turbidity created by doping samples with silica flour with grain sizes ranging from 1.6 to 5.0 μm were employed to develop relationships between observed Raman signal strength and turbidity level. Shared characteristics of these relationships were then employed to define generalized correction methods for the effect of turbidity on Raman observations of compounds in aqueous solution.

Imperanene, a novel phenolic compound with platelet aggregation inhibitory activity from Imperata cylindrica.

PubMed

Matsunaga, K; Shibuya, M; Ohizumi, Y

1995-01-01

Imperanene, a novel phenolic compound [1] has been isolated from Imperata cylindrica. Its structure was elucidated by spectroscopic evidence. Imperanene showed platelet aggregation inhibitory activity.

Fruit Antioxidants during Vinegar Processing: Changes in Content and in Vitro Bio-Accessibility

PubMed Central

Bakir, Sena; Toydemir, Gamze; Boyacioglu, Dilek; Beekwilder, Jules; Capanoglu, Esra

2016-01-01

Background: Vinegars based on fruit juices could conserve part of the health-associated compounds present in the fruits. However, in general very limited knowledge exists on the consequences of vinegar-making on different antioxidant compounds from fruit. In this study vinegars derived from apple and grape are studied. Methods: A number of steps, starting from the fermentation of the fruit juices to the formation of the final vinegars, were studied from an industrial vinegar process. The effect of each of the vinegar processing steps on content of antioxidants, phenolic compounds and flavonoids was studied, by spectroscopic methods and by high-performance liquid chromatography (HPLC). Results: The major observation was that spectrophotometric methods indicate a strong loss of antioxidant phenolic compounds during the transition from fruit wine to fruit vinegar. A targeted HPLC analysis indicates that metabolites such as gallic acid are lost in later stages of the vinegar process. Conclusion: The major conclusion of this work is that major changes occur in phenolic compounds during vinegar making. An untargeted metabolite analysis should be used to reveal these changes in more detail. In addition, the effect of vinegar processing on bio-accessibility of phenolic compounds was investigated by mimicking the digestive tract in an in vitro set up. This study is meant to provide insight into the potential of vinegar as a source of health-related compounds from fruit. PMID:27690020

Spectroscopic Study on the Interaction of 4-dimethylaminochalcones with Phospholipids

NASA Astrophysics Data System (ADS)

Tomečková, V.; Revická, M.; Sassen, A.; Veliká, B.; Stupák, M.; Perjési, P.

2014-11-01

The ultraviolet-visible and fluorescence spectroscopic properties of 4'-dimethylaminochalcone ( 1a) and its cyclic analogs 2a-4a have been studied in the presence of phospholipid vesicles (i.e., egg yolk lecithin and dipalmitoylpho sphatidylcholine), bovine serum albumin (BSA), and lipoprotein particles (i.e., bovine serum albumin plus egg yolk lecithin). The spectral results showed that compounds 1a-4a formed hydrophobic interactions with the phospholipids, lipoproteins, and BSA at the polar/nonpolar interface. Compounds 3a and 4a exhibited the strongest hydrophobic interactions of all of the compounds tested towards the phospholipids. Compound 2a gave the best fluorescent fluorophore indicating interactions with the lipids, lipoproteins, and proteins. Fluorescent microscopic imaging of breast cancer cells treated with compounds 1a-4a revealed that they could be used to stain all of the cellular components and destroy the nuclear structure. Compounds 1a-4a were found to be concentrated predominantly on the surfaces of the liposomes and lipoproteins.

FT-IR spectroscopic, thermal analysis of human urinary stones and their characterization

NASA Astrophysics Data System (ADS)

Selvaraju, R.; Raja, A.; Thiruppathi, G.

2015-02-01

In the present study, FT-IR, XRD, TGA-DTA spectral methods have been used to investigate the chemical compositions of urinary calculi. Multi-components of urinary calculi such as calcium oxalate, hydroxyl apatite, struvite and uric acid have been studied. The chemical compounds are identified by FT-IR spectroscopic technique. The mineral identification was confirmed by powder X-ray diffraction patterns as compared with JCPDS reported values. Thermal analysis techniques are considered the best techniques for the characterization and detection of endothermic and exothermic behaviors of the urinary stones. The percentages of each hydrate (COM and COD) are present together, in the presences of MAPH or UA. Finally, the present study suggests that the Urolithiasis is significant health problem in children, and is very common in some parts of the world, especially in India. So that present study is so useful and helpful to the scientific community for identification of latest human health problems and their remedies using spectroscopic techniques.

Xanthanolides and xanthane epoxide derivatives from Xanthium strumarium.

PubMed

Mahmoud, A A

1998-12-01

From the aerial parts of Xanthium strumarium, three new xanthanolide and xanthane-type sesquiterpenoids, 11alpha,13-dihydroxanthatin, 4beta,5beta-epoxyxanthatin-1alpha,4alpha-endoperoxide, and 1beta,4beta,4alpha,5alpha-diepoxyxanth-11(13)-en-12-oic acid have been isolated, together with seven known compounds. The structures were determined by spectroscopic methods, particularly high resolution 1D, 2D NMR spectroscopy and NOE experiments.

Spectroscopic Studies of Nuclear Submarine Atmospheres. I. Desorption and Analysis of Contaminants from Hopcalite

DTIC Science & Technology

A semi-microanalytical method is described for desorbing contaminants from Hopcalite , an oxide catalyst used in the purification of submarine...contaminants are desorbed from the Hopcalite by passing pressurized steam through a column of the catalyst. The various compounds are eluted from the column...appropriate solvent. Infrared spectral analyses of contaminants desorbed from Hopcalite following its use as a catalyst for the oxidation of pure

Tetracyclic indole alkaloids with antinematode activity from Uncaria rhynchophylla.

PubMed

Kong, Fandong; Ma, Qingyun; Huang, Shengzhuo; Yang, Shuang; Fu, Linran; Zhou, Liman; Dai, Haofu; Yu, Zhifang; Zhao, Youxing

2017-06-01

A new tetracyclic indole alkaloid, 17-O-methyl-3,4,5,6-tetradehydrogeissoschizine, together with seven known ones, were isolated from the aerial part of Uncaria rhynchophylla. Their structures were unambiguously elucidated by spectroscopic methods and comparing with the literature data. Among them, compounds 1, 3, 4 and 6-8 showed potent to moderate antinematode activities against Panagrellus redivevus at a concentration of 250 μg/mL.

A Routine Experimental Protocol for qHNMR Illustrated with Taxol⊥

PubMed Central

Pauli, Guido F.; Jaki, Birgit U.; Lankin, David C.

2012-01-01

Quantitative 1H NMR (qHNMR) provides a value-added dimension to the standard spectroscopic data set involved in structure analysis, especially when analyzing bioactive molecules and elucidating new natural products. The qHNMR method can be integrated into any routine qualitative workflow without much additional effort by simply establishing quantitative conditions for the standard solution 1H NMR experiments. Moreover, examination of different chemical lots of taxol and a Taxus brevifolia extract as working examples led to a blueprint for a generic approach to performing a routinely practiced 13C-decoupled qHNMR experiment, and for recognizing its potential and main limitations. The proposed protocol is based on a newly assembled 13C GARP broadband decoupled proton acquisition sequence that reduces spectroscopic complexity by removal of carbon satellites. The method is capable of providing qualitative and quantitative NMR data simultaneously and covers various analytes from pure compounds to complex mixtures such as metabolomes. Due to a routinely achievable dynamic range of 300:1 (0.3%) or better, qHNMR qualifies for applications ranging from reference standards to biologically active compounds to metabolome analysis. Providing a “cookbook” approach to qHNMR, acquisition conditions are described that can be adapted for contemporary NMR spectrometers of all major manufacturers. PMID:17298095

Antibacterial and Hypoglycemic Diterpenoids from Salvia chamaedryoides.

PubMed

Bisio, Angela; De Mieri, Maria; Milella, Luigi; Schito, Anna M; Parricchi, Anita; Russo, Daniela; Alfei, Silvana; Lapillo, Margherita; Tuccinardi, Tiziano; Hamburger, Matthias; De Tommasi, Nunziatina

2017-02-24

A surface extract of the aerial parts of Salvia chamaedryoides afforded 13 diterpenes (1-13), with seven compounds (1, 3, 4, 7-9, 12) described for the first time. The structures of the new compounds were established using 1D and 2D NMR spectroscopic methods, HRESIMS, and ECD data. The potential hypoglycemic effects of the crude extract, fractions, and pure compounds from S. chamaedryoides were investigated by inhibition of α-glucosidase and α-amylase enzymes. The extract and its fractions showed a moderate dose-dependent inhibition; the pure compounds exhibited differential inhibitory activity against these two enzymes. Molecular modeling studies were also performed to suggest the interaction mode of compound 3 in the α-glucosidase enzyme active site. The antimicrobial activity of the purified compounds was investigated against 26 clinical pathogens. No activity was detected for the Gram-negative species tested nor on Candida albicans and C. glabrata, while variable susceptibilities were observed using Gram-positive staphylococcal and enterococcal species.

Antinociceptive activity of extracts and secondary metabolites from wild growing and micropropagated plants of Renealmia alpinia

PubMed Central

Gómez-Betancur, Isabel; Cortés, Natalie; Benjumea, Dora; Osorio, Edison; León, Francisco; Cutler, Stephen J.

2015-01-01

Ethnopharmacological relevance Renealmia alpinia is native to the American continent and can be found from Mexico to Brazil, and in the Caribbean islands. It is known as “matandrea” in Colombia, and it has been commonly used in traditional medicine to treat painful diseases and ailments. Based on its traditional uses, it is of interest to evaluate the pharmacologic effects of this plant and its secondary metabolites. Materials and methods Methanol and aqueous extracts of wild and micropropagated R. alpinia (leaves) were obtained and chemically compared by High Performance Thin Layer Chromatography (HPTLC). The antinociceptive activity of these extracts was examined using an in vivo assay (Siegmund test). Additionally, the dichloromethane extract of R. alpinia was fractionated and pure compounds were isolated by chromatographic methods. The structure elucidation of isolated compounds was performed by NMR experiments and spectroscopic techniques and comparison with the literature data. Purified compounds were evaluated for their in vitro binding affinity for opioids and cannabinoids receptors. Results The dichloromethane extract of the plant’s aerial part afforded sinostrobin (1), naringenin 7,4′-dimethyl ether (2), 2′,6′-dihydroxy-4′-methoxychalcone (3), 4-methoxy-6-(2-phenylethenyl)-2H-pyran-2-one (4), naringenin 7-methyl ether (5) and 3,5-heptanediol, 1,7-diphenyl (6), which were isolated using chromatographic methods. Their chemical structures were established by physical and spectroscopic techniques. The antinociceptive effects observed in mice by extracts of wild and micropropagated plants were similar. The compounds isolated from R. alpinia do not show affinity to opioid or cannabinoid receptors. Conclusion Aqueous and methanol extracts of R. alpinia provide antinociceptive and analgesic effects in an in vivo model. These results contribute additional insight as to why this plant is traditionally used for pain management. Also, this is the first comprehensive report of a phytochemical study of R. alpinia. PMID:25686780

New 1,3,4-thiadiazole compounds including pyrazine moiety: Synthesis, structural properties and antimicrobial features

NASA Astrophysics Data System (ADS)

Gür, Mahmut; Şener, Nesrin; Muğlu, Halit; Çavuş, M. Serdar; Özkan, Osman Emre; Kandemirli, Fatma; Şener, İzzet

2017-07-01

In the study, some new 1,3,4-thiadiazole compounds were synthesized and we have reported identification of the structures by using UV-Vis, FT-IR, 1H NMR, 13C NMR and Mass spectroscopic methods. Antimicrobial activities of the compounds against three microorganisms, namely, Candida albicans ATCC 26555, Staphylococcus aureus ATCC 9144, and Escherichia coli ATCC 25922 were investigated by using disk diffusion method. These thiadiazoles exhibited an antimicrobial activity against Staphylococcus aureus and Candida albicans. The experimental data was supported by the quantum chemical calculations. Density functional theory (DFT) calculations were carried out to obtain the ground state optimized geometries of the molecules using the B3LYP, M06 and PBE1PBE methods with 3-21 g, 4-31 g, 6-311++g(2d,2p), cc-pvtz and cc-pvqz basis sets in the different combinations. Frontier molecular orbitals (FMOs) energies, band gap energies and some chemical reactivity parameters were calculated by using the aforementioned methods and basis sets, and the results were also compared with the experimental UV-Vis data.

Synthesis, spectroscopic and structural characterization of 5-benzoyl-4-phenyl-2-methylthio-1H-pyrimidine with theoretical calculations using density functional theory.

PubMed

Inkaya, Ersin; Dinçer, Muharrem; Sahan, Emine; Yıldırım, Ismail

2013-10-01

In this paper, we will report a combined experimental and theoretical investigation of the molecular structure and spectroscopic parameters (FT-IR, (1)H NMR, (13)C NMR) of 5-benzoyl-4-phenyl-2-methylthio-1H-pyrimidine. The compound crystallizes in the triclinic space group P-1 with Z=2. The molecular geometry was also optimized using density functional theory (DFT/B3LYP) method with the 6-311G(d,p) and 6-311++G(d,p) basis sets in ground state and compared with the experimental data. All the assignments of the theoretical frequencies were performed by potential energy distributions using VEDA 4 program. Information about the size, shape, charge density distribution and site of chemical reactivity of the molecules has been obtained by mapping electron density isosurface with electrostatic potential (ESP). Also, non-linear optical properties of the title compound were performed at B3LYP/6-311++G(d,p) level. The theoretical results showed an excellent agreement with the experimental values. Copyright © 2013 Elsevier B.V. All rights reserved.

Synthesis, spectroscopic and structural characterization of 5-benzoyl-4-phenyl-2-methylthio-1H-pyrimidine with theoretical calculations using density functional theory

NASA Astrophysics Data System (ADS)

İnkaya, Ersin; Dinçer, Muharrem; Şahan, Emine; Yıldırım, İsmail

2013-10-01

In this paper, we will report a combined experimental and theoretical investigation of the molecular structure and spectroscopic parameters (FT-IR, 1H NMR, 13C NMR) of 5-benzoyl-4-phenyl-2-methylthio-1H-pyrimidine. The compound crystallizes in the triclinic space group P-1 with Z = 2. The molecular geometry was also optimized using density functional theory (DFT/B3LYP) method with the 6-311G(d,p) and 6-311++G(d,p) basis sets in ground state and compared with the experimental data. All the assignments of the theoretical frequencies were performed by potential energy distributions using VEDA 4 program. Information about the size, shape, charge density distribution and site of chemical reactivity of the molecules has been obtained by mapping electron density isosurface with electrostatic potential (ESP). Also, non-linear optical properties of the title compound were performed at B3LYP/6-311++G(d,p) level. The theoretical results showed an excellent agreement with the experimental values.

FT-IR, UV-vis, 1H and 13C NMR spectra and the equilibrium structure of organic dye molecule disperse red 1 acrylate: a combined experimental and theoretical analysis.

PubMed

Cinar, Mehmet; Coruh, Ali; Karabacak, Mehmet

2011-12-01

This study reports the characterization of disperse red 1 acrylate compound by spectral techniques and quantum chemical calculations. The spectroscopic properties were analyzed by FT-IR, UV-vis, (1)H NMR and (13)C NMR techniques. FT-IR spectrum in solid state was recorded in the region 4000-400 cm(-1). The UV-vis absorption spectrum of the compound that dissolved in methanol was recorded in the range of 200-800 nm. The (1)H and (13)C NMR spectra were recorded in CDCl(3) solution. The structural and spectroscopic data of the molecule in the ground state were calculated using density functional theory (DFT) employing B3LYP exchange correlation and the 6-311++G(d,p) basis set. The vibrational wavenumbers were calculated and scaled values were compared with experimental FT-IR spectrum. A satisfactory consistency between the experimental and theoretical spectra was obtained and it shows that the hybrid DFT method is very useful in predicting accurate vibrational structure, especially for high-frequency region. The complete assignments were performed on the basis of the experimental results and total energy distribution (TED) of the vibrational modes, calculated with scaled quantum mechanics (SQM) method. Isotropic chemical shifts were calculated using the gauge-invariant atomic orbital (GIAO) method. A study on the electronic properties were performed by timedependent DFT (TD-DFT) and CIS(D) approach. To investigate non linear optical properties, the electric dipole moment μ, polarizability α, anisotropy of polarizability Δα and molecular first hyperpolarizability β were computed. The linear polarizabilities and first hyperpolarizabilities of the studied molecule indicate that the compound can be a good candidate of nonlinear optical materials. Copyright © 2011 Elsevier B.V. All rights reserved.

Structure determination of two new indole-diterpenoids from Penicillium sp. CM-7 by NMR spectroscopy.

PubMed

Zhang, Yu-Hong; Huang, Sheng-Dong; Pan, Hua-Qi; Bian, Xi-Qing; Wang, Zai-Ying; Han, Ai-Hong; Bai, Jiao

2014-06-01

Two new indole-diterpenoids 4b-deoxy-1'-O-acetylpaxilline (1) and 4b-deoxypenijanthine A (2) were isolated from the fermentation broth and the mycelia of the soil fungus Penicillium sp. CM-7, along with three known structurally related compounds, 1'-O-acetylpaxilline (3), paspaline (4) and 3-deoxo-4b-deoxypaxilline (5). The structures of compounds 1 and 2 were elucidated by extensive spectroscopic methods, especially 2D NMR, and their absolute configurations were suggested on the basis of the circular dichroism spectral analysis and the NOESY data. Copyright © 2014 John Wiley & Sons, Ltd.

Penixanthones A and B, two new xanthone derivatives from fungus Penicillium sp. SYFz-1 derived of mangrove soil sample.

PubMed

Tao, Huaming; Wei, Xiaoyi; Lin, Xiuping; Zhou, Xuefeng; Dong, Junde; Yang, Bin

2017-10-01

Two new xanthone derivatives, penixanthones A (1) and B (2), together with three known compounds, aspenicillide (3), 1,5-dihydroxy-3-methoxy-7-methyl-anthracene-9,10-dione (4) and 1,2-indandiol (5), were isolated from the ethyl acetate extract of a culture of the fungus Penicillium sp. SYFz-1, which was separated from a mangrove soil sample. The structures of these compounds were elucidated by spectroscopic methods including NMR and mass spectrometry. The absolute configurations of penixanthones A (1) and B (2) were determined on the basis of electronic circular dichroism (ECD) data analysis.

Pregnane steroids from a gorgonian coral Subergorgia suberosa with anti-flu virus effects.

PubMed

Cheng, Wei; Ren, Jinwei; Huang, Qixi; Long, Hailin; Jin, Hongwei; Zhang, Liangren; Liu, Huagang; van Ofwegen, Leen; Lin, Wenhan

2016-04-01

Five new pregnane-type steroids namely subergorgols T-X (1-5) and three known analogues (6-8) were isolated from a gorgonian coral Subergorgia suberosa. The structures of new compounds were determined on the basis of extensive spectroscopic (IR, MS, 1D and 2D NMR) data analyses, in association with photochemical transformation and ECD methods for the configurational assignment. Compounds 1-8 were evaluated for the inhibitory effects against H1N1 virus infected in MDCK cells, while subergorgols T-U and 1,2-dehydroprogesterone exerted potent inhibition against A/WSN/33 virus. Copyright © 2016 Elsevier Inc. All rights reserved.

LC-MS guided isolation of ent-kaurane diterpenoids from Nouelia insignis.

PubMed

Sun, Chang-Li; Geng, Chang-An; Chen, Xing-Long; Yang, Tong-Hua; Yin, Xiu-Juan; Huang, Xiao-Yan; Peng, Hua; Chen, Ji-Jun

2016-06-01

The preliminary LC-MS investigation on the stems of Nouelia insignis manifested the existence of diterpenoids. As a result, 15 ent-kaurane diterpenoids, including 7 new glycosides (nouelosides A-G, 1-7), were isolated under the direction of LC-MS analysis. The new compounds were determined by extensive spectroscopic analysis including HRESIMS, 1D and 2D NMR data and chemical methods. Compounds 6 and 15 with the exo-methylene cyclopentanone functional group exhibited obvious nitric oxide production inhibitory activity with IC50 values of 3.84±0.20 and 3.19±0.25μM. Copyright © 2016 Elsevier B.V. All rights reserved.

Biotransformation of ent-kaur-16-en-19-oic acid by Psilocybe cubensis.

PubMed

Pechwang, Jaraslak; Sihanonth, Prakitsin; Pornpakakul, Surachai; Muangsin, Nongnuj; Piapukiew, Jittra; Vangnai, Alisa; Chaichit, Narongsak; Chuchawankul, Siriporn; Petsom, Amorn

2010-06-01

Biotranformation of ent-kaur-16-en-19-oic acid (1) using Psilocybe cubensis resulted in hydroxylated products. After two days of incubation, ent-16beta,17-dihydroxy-kauran-19-oic acid (2) was isolated. After further incubation for nine days, two novel metabolites, ent-12alpha,16beta,17-trihydroxy-kauran-19-oic acid (3) and ent-11alpha,16beta,17-trihydroxy-kauran-19-oic acid (4), were obtained. The metabolites were identified by spectroscopic methods and X-ray crystallography. Compounds 1-4 were evaluated for their cytotoxic properties against the human leukaemia K562 cell line; only compound 1 showed moderate activity.

Rhodomollanol A, a Highly Oxygenated Diterpenoid with a 5/7/5/5 Tetracyclic Carbon Skeleton from the Leaves of Rhododendron molle.

PubMed

Zhou, Junfei; Zhan, Guanqun; Zhang, Hanqi; Zhang, Qihua; Li, Ying; Xue, Yongbo; Yao, Guangmin

2017-07-21

A novel diterpenoid with an unprecedented carbon skeleton, rhodomollanol A (1), and a new grayanane diterpenoid, rhodomollein XXXI (2), were isolated from the leaves of Rhododendron molle. Their structures were elucidated using comprehensive spectroscopic methods and single-crystal X-ray diffraction. Compound 1 possesses a unique cis/trans/trans/cis/cis-fused 3/5/7/5/5/5 hexacyclic ring system featuring a rare 7-oxabicyclo[4.2.1]nonane core decorated with three cyclopentane units. The plausible biosynthetic pathway for 1 was proposed. Compound 1 exhibited moderate PTP1B inhibitory activity.

Inclusion compound of vitamin B6 in β-CD. Physico-chemical and structural investigations

NASA Astrophysics Data System (ADS)

Borodi, Gheorghe; Kacso, Irina; Farcaş, Sorin I.; Bratu, Ioan

2009-08-01

Structural and physico-chemical characterization of supramolecular assembly of vitamin B6 with β-cyclodextrin (β-CD) prepared by different methods (kneading, co-precipitation and freeze-drying) has been performed by using several spectroscopic techniques (FTIR, 1H NMR, UV-Vis), powder X-ray diffraction and DSC in order to evidence the inclusion compound formation. An analysis of the chemical shifts observed in the 1H-NMR spectra and of the vibrational frequency shifts led to the tentative conclusion that the vitamin B6 probably enters the cyclodextrin torus when forming the β-CD-vitamin B6 inclusion complex.

Spectroscopic investigation on structure and pH dependent Cocrystal formation between gamma-aminobutyric acid and benzoic acid

NASA Astrophysics Data System (ADS)

Du, Yong; Xue, Jiadan; Cai, Qiang; Zhang, Qi

2018-02-01

Vibrational spectroscopic methods, including terahertz absorption and Raman scattering spectroscopy, were utilized for the characterization and analysis of gamma-aminobutyric acid (GABA), benzoic acid (BA), and the corresponding GABA-BA cocrystal formation under various pH values of aqueous solution. Vibrational spectroscopic results demonstrated that the solvent GABA-BA cocrystal, similar as grinding counterpart, possessed unique characteristic features compared with that of starting parent compounds. The change of vibrational modes for GABA-BA cocrystal comparing with starting components indicates there is strong inter-molecular interaction between GABA and BA molecules during its cocrystallization process. Formation of GABA-BA cocrystal under slow solvent evaporation is impacted by the pH value of aqueous solution. Vibrational spectra indicate that the GABA-BA cocrystal could be stably formed with the solvent condition of 2.00 ≤ pH ≤ 7.00. In contrast, such cocrystallization did not occur and the cocrystal would dissociate into its parent components when the pH value of solvent is lower than 2.00. This study provides experimental benchmark to discriminate and identify the structure of cocrystal and also pH-dependent cocrystallization effect with vibrational spectroscopic techniques in solid-state pharmaceutical fields.

Synthesis, spectroscopic characterization and structural investigations of new adduct compound of carbazole with picric acid: DNA binding and antimicrobial studies.

PubMed

Saravanabhavan, Munusamy; Sathya, Krishnan; Puranik, Vedavati G; Sekar, Marimuthu

2014-01-24

Carbazole picrate (CP), a new organic compound has been synthesized, characterized by various analytical and spectroscopic technique such as FT-IR, UV-Vis, (1)H and (13)C NMR spectroscopy. An orthorhombic geometry was proposed based on single crystal XRD study. The thermal stability of the crystal was studied by using thermo-gravimetric and differential thermal analyses and found that it was stable up to 170°C. Further, the newly synthesized title compound was tested for its in vitro antibacterial and antifungal activity against various bacterial and fungal species. Also, the compound was tested for its binding activity with Calf thymus (CT) DNA and the results show a considerable interaction between CP and CT-DNA. Copyright © 2013 Elsevier B.V. All rights reserved.

Phytotoxicity, structural and computational analysis of 2-methyl-1,5-diarylpentadienones

NASA Astrophysics Data System (ADS)

Din, Zia Ud; Rodrigues-Filho, Edson; de Cassia Pereira, Viviane; Gualtieri, Sonia Cristina Juliano; Deflon, Victor Marcelo; da Silva Maia, Pedro Ivo; Kuznetsov, Aleksey E.

2017-08-01

In our studies aimed to produce new chemicals used in weed control, 2-methyl-1,5-diarylpentadienones were synthesized by the reaction of p-methoxybenzaldehyde, p-nitrobenzaldehyde and p-N,N-dimethylbenzaldehyde, respectively, with 2-butanone, resulting in four model compounds. The phytotoxicity of these compounds against wheat coleoptiles and Sesame seedling was observed at μM concentrations, indicating good potential for their usage in weed management in the field. Spectroscopic and computational studies were performed in order to gain understanding on their mechanisms of action and to clarify some structural complexities due existence of conformers and substituent effects. These compounds probably act as hydroxyphenylpyruvate dioxygenase inhibitors. The tested compounds were characterized by spectroscopic and single crystal X-ray diffraction analyses. Solid crystalline state of the compound A (2-Methyl-1-(p-methophyphenyl)-5-(phenyl)-diarylpentadienone) is observed in the monoclinic space group P21/c with unit cell dimensions a = 14.3366(4) Å, b = 11.3788(4) Å, c = 9.6319(3) Å, β = 96.596, V = 1560.88(9) Å3 and Z = 4. Compound C (2-Methyl-1-(p-methophyphenyl)-5-(p-nitrophenyl)-diarylpentadienone) crystallizes in the monoclinic space group P21/c with unit cell dimensions a = 17.8276(9) Å, b = 7.3627(4) Å, c = 12.9740(6) Å, β = 107.6230(10), V = 1623.04(14) Å3 and Z = 4. LC-UV-MS analysis furnished important data helpful for their characterization. The spectroscopic data and computational (DFT) analysis revealed the fact that each of the compounds A-D occurs in solution as four conformers.

Conformational, electronic, and spectroscopic characterization of isophthalic acid (monomer and dimer structures) experimentally and by DFT

NASA Astrophysics Data System (ADS)

Bardak, F.; Karaca, C.; Bilgili, S.; Atac, A.; Mavis, T.; Asiri, A. M.; Karabacak, M.; Kose, E.

2016-08-01

Isophthalic acid (C6H4(CO2H)2) is a noteworthy organic compound widely used in coating and synthesis of resins and the production of commercially important polymers such as drink plastic bottles. The effects of isophthalic acid (IPA) on human health, toxicology, and biodegradability are the main focus of many researchers. Because structural and spectroscopic investigation of molecules provides a deep understanding of interactional behaviors of compounds, this study stands for exploring those features. Therefore, the spectroscopic, structural, electronic, and thermodynamical properties of IPA were thoroughly studied in this work experimentally using UV-Vis, 1H and 13C NMR, FT-IR, FT-Raman and theoretically via DFT and TD-DFT calculations. The UV-Vis absorption spectrum in water was taken in the region 200-400 nm. The NMR chemical shifts (1H and 13C) were recorded in DMSO solution. The infrared and Raman spectra of the solid IPA were recorded in the range of 4000-400 cm- 1 and 3500-50 cm- 1, respectively. DFT and TD-DFT calculations were performed at the level of B3LYP/6-311++G(d,p) in determination of geometrical structure, electronic structure analysis and normal mode. The 13C and 1H nuclear magnetic resonance (NMR) spectra were estimated by using the gauge-invariant atomic orbital (GIAO) method. The scaled quantum mechanics (SQM) method was used to determine the total energy distribution (TED) to assign the vibrational modes accurately. Weak interactions such as hydrogen bonding and Van der Walls were analyzed via reduced density gradient (RDG) analysis in monomeric and dimeric forms. Furthermore, the excitation energies, density of state (DOS) diagram, thermodynamical properties, molecular electro-static potential (MEP), and nonlinear optical (NLO) properties were obtained.

Antimicrobial metabolites from the plant endophytic fungus Penicillium sp.

PubMed

Yang, Ming-Hua; Li, Tian-Xiao; Wang, Ying; Liu, Rui-Huan; Luo, Jun; Kong, Ling-Yi

2017-01-01

Five rare dichloro aromatic polyketides (1-5) were obtained from an endophytic fungus Penicillium sp., along with five known metabolites (6-10). Their structures were elucidated by extensive spectroscopic analysis, Mosher methods, as well as [Rh 2 (OCOCF 3 ) 4 ]-induced electronic circular dichroism (ECD) experiments. Compounds 2-4 and 6 structurally involved acyclic 1.3-diols, the uneasy configuration determinations of which were well carried out by double-derivation NMR methods. Compounds 1-10 were evaluated for their antibacterial and antifungal activities against five strains of human pathogenic microorganisms. Helvolic acid (7) showed potent inhibitory effects against Staphylococcus aureus and Pseudomonas aeruginosa with MIC (minimum inhibitory concentration) values of 5.8 and 4.6μg/mL, respectively. Copyright © 2016 Elsevier B.V. All rights reserved.

Ethylenediammonium dication: H-bonded complexes with terephthalate, chloroacetate, phosphite, selenite and sulfamate anions. Detailed vibrational spectroscopic and theoretical studies of ethylenediammonium terephthalate.

PubMed

Marchewka, M K; Drozd, M

2012-12-01

Crystalline complexes between ethylenediammonium dication and terephthalate, chloroacetate, phosphite, selenite and sulfamate anions were obtained by slow evaporation from water solution method. Room temperature powder infrared and Raman measurements were carried out. For ethylenediammonium terephthalate theoretical calculations of structure were performed by two ways: ab-initio HF and semiempirical PM3. In this case the PM3 method gave more accurate structure (closer to X-ray results). The additional PM3 calculations of vibrational spectra were performed. On the basis theoretical approach and earlier vibrational studies of similar compounds the vibrational assignments for observed bands have been proposed. All compounds were checked for second harmonic generation (SHG). Copyright © 2012 Elsevier B.V. All rights reserved.

Fast dynamic electron transfer along infinite anion-cation chains in technetium and rhenium acido clusters

DOE Office of Scientific and Technical Information (OSTI.GOV)

Antipov, B.G.; Kryuchkov, S.V.; Grigor`ev, M.S.

1995-09-01

New technetium and rhenium compounds with ferricenium cations - [Fe(C{sub 5}H{sub 5}){sub 2}]{sub 3}[Tc{sub 6}I{sub 14}], [Fe(C{sub 5}H{sub 5}){sub 2}]{sub 3}[Tc{sub 6}Cl{sub 14}], [Fe(C{sub 5}H{sub 5}){sub 2}]{sub 2}[Tc{sub 8}Br{sub 14}], and [Fe(C{sub 5}H{sub 5}){sub 2}]{sub 2}[Re{sub 2}Br{sub 8}] - are synthesized and identified. The compounds are characterized by the methods of static magnetic susceptibility and differential scanning calorimetry; solid-state conductivity measurements; and IR, EPR, {sup 57}Fe Moessbauer, and X-ray photoelectron spectroscopic data. These data are compared with the physicochemical characteristics of ferricenium pertechnetate and hexachlorotechnetate, as well as of a number of reference technetium and rhenium compounds containing the samemore » anions but different cations. The structure of [Fe(C{sub 5}H{sub 5}){sub 2}]{sub 3}[Tc{sub 6}I{sub 14}] is determined by X-ray diffraction analysis of a single crystal [space group P6/m, a = 15.34(2), c = 12.70(1) {angstrom}]. The structures of the remaining compounds were confirmed by comparing their spectroscopic properties with corresponding properties of compounds with known composition and structure. None of the compounds with ferricenium cations exhibit covalent or other localized bonds between anions and cations. However, the physicochemical properties of these compounds indicate the occurrence of a fast dynamic electron transfer along infinite anion-cation chains. Compounds [Fe(C{sub 5}H{sub 5}){sub 2}]{sub 3}[Tc{sub 6}Cl{sub 14}] and [Fe(C{sub 5}H{sub 5}){sub 2}]{sub 2}[Tc{sub 8}Br{sub 14}] were found to exhibit a new phenomenon of X-ray-induced low-temper ature high-energy electron emission.« less

(+)-rumphiin and polyalthurea, new compounds from the stems of Polyalthia rumphii.

PubMed

Wang, Tian-Shan; Luo, You-Ping; Wang, Jing; He, Meng-Xiong; Zhong, Ming-Guo; Li, Ying; Song, Xiao-Ping

2013-10-01

Two new compounds, (+)-rumphiin (3) and polyalthurea (7), together with seven known ones, 3,4,5-trimethoxy benzoic acid (1), (-)-seselinone (2), cannabisin D (4), allantoin (5), oxostephanine (6) and a mixture of beta-sitosterol (8) and stigmasterol (9) were isolated from the stems of Polyalthia rumphii. The chemical structures of 3 and 7 were elucidated by the combination of spectroscopic data, and the absolute configuration of 3 at C-2 was determined by the matrix method to be R. All compounds were evaluated for their cytotoxicity on four human cancer cell lines, which demonstrated that 3 was a moderate bioactive lignan, and 6 showed significant anticancer activity against SPC-A-1 and BEL-7402 cell lines with IC50 values of 1.47 and 1.73 microg/mL, respectively.

Novel 2,5-disubtituted-1,3,4-oxadiazoles with benzimidazole backbone: a new class of β-glucuronidase inhibitors and in silico studies.

PubMed

Zawawi, Nik Khairunissa Nik Abdullah; Taha, Muhammad; Ahmat, Norizan; Wadood, Abdul; Ismail, Nor Hadiani; Rahim, Fazal; Ali, Muhammad; Abdullah, Norishah; Khan, Khalid Mohammed

2015-07-01

A library of novel 2,5-disubtituted-1,3,4-oxadiazoles with benzimidazole backbone (3a-3r) was synthesized and evaluated for their potential as β-glucuronidase inhibitors. Several compounds such as 3a-3d, 3e-3j, 3l-3o, 3q and 3r showed excellent inhibitory potentials much better than the standard (IC50=48.4±1.25μM: d-saccharic acid 1,4-lactone). All the synthesized compounds were characterized satisfactorily by using different spectroscopic methods. We further evaluated the interaction of the active compounds and the enzyme active site with the help of docking studies. Copyright © 2015 Elsevier Ltd. All rights reserved.

Cycloartanes from Euphorbia aellenii Rech. f. and their Antiproliferative Activity

PubMed Central

Ayatollahi, Abdul Majid; Ghanadian, Mustafa; Afsharypuor, Suleiman; Mesaik, M. Ahmad; Abdalla, Omer Mohamed; Shahlaei, Mohsen; Farzandi, Gholamhossein; Mostafavi, Hamid

2011-01-01

The cytotoxic chloroform fraction of Euphorbia aellenii afforded two cycloartane type triterpenes-cycloart-25-en-3β,24-diol (1) and 24-methylene-cycloartan-3β-ol (2)-for the first time from this plant. Preparation of cycloartane derivatives, 3β, 24-O-diacetyl-cycloart-25-en as compound 3 and 3β-O-acetyl-24-methylene-cycloartan (4) were conducted by acetylating of 1 and 2, respectively. The structures of the isolated compounds were elucidated by spectroscopic methods and their activities evaluated by proliferation assay on human peripheral blood lymphocytes (PBLs). Comparing the results suggested that anti-proliferation effect of these compounds on PBLs might be due to the presence of free 3-OH group while masking the free OH groups by acetylation, could induce proliferation activity. PMID:24363688

One new diphenylmethane glycoside from the leaves of Psidium guajava L.

PubMed

Shu, Ji-Cheng; Chou, Gui-Xin; Wang, Zheng-Tao

2012-11-01

To investigate the chemical constituents of Psidium guajava L, the EtOH/H(2)O extract of the fresh leaves was subjected to various chromatography. One diphenylmethane, one benzophenone, and eight flavonoids were isolated and elucidated as 2,6-dihydroxy-3-formaldehyde-5-methyl-4-O-(6″-O-galloyl-β-D-glucopyranosyl)-diphenylmethane (1), 2,6-dihydroxy-3,5-dimethyl-4-O-(6″-O-galloyl-β-D-glucopyranosyl)-benzophenone (2), kaempferol (3), quercetin (4), quercitrin (5), isoquercitrin (6), guaijaverin (7), avicularin (8), hyperoside (9), reynoutrin (10) by spectroscopic methods, including 1D and 2D NMR and HR-ESI-MS spectrometry as well as by comparison with published data. Compounds 5 and 10 are obtained from P. guajava for the first time, and compound 1 is a new diphenylmethane compound.

Antioxidant phenolic compounds from the rhizomes of Astilbe rivularis.

PubMed

Hori, Kengo; Wada, Mikiyo; Yahara, Shoji; Watanabe, Takashi; Devkota, Hari Prasad

2018-02-01

The rhizomes of Astilbe rivularis, commonly known as 'Thulo Okhati' are widely used in Nepal as tonic for uterine and menstrual disorders. In our preliminary study, the 70% MeOH extract of the rhizomes showed potent antioxidant activity. Hence, present study was aimed for the isolation of potent antioxidant constituents. Bergenin (1), 11-O-galloylbergenin (2), (+)-catechin (3), (-)-catechin (4), (-)-afzelechin (5), (-)-epiafzelechin (6) and 2-(β-D-glucopyranosyloxy)-4-hydroxylbenzenacetonitrile (7) were isolated from the rhizomes. Structures of these compounds were elucidated on the basis of spectroscopic methods. All these isolated compounds were evaluated for their in vitro antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. 11-O-Galloylbergenin (2), (+)-catechin (3), (-)-catechin (4), (-)-afzelechin (5) and (-)-epiafzelechin (6) showed potent antioxidant activity.

Quantitative analysis of red wine tannins using Fourier-transform mid-infrared spectrometry.

PubMed

Fernandez, Katherina; Agosin, Eduardo

2007-09-05

Tannin content and composition are critical quality components of red wines. No spectroscopic method assessing these phenols in wine has been described so far. We report here a new method using Fourier transform mid-infrared (FT-MIR) spectroscopy and chemometric techniques for the quantitative analysis of red wine tannins. Calibration models were developed using protein precipitation and phloroglucinolysis as analytical reference methods. After spectra preprocessing, six different predictive partial least-squares (PLS) models were evaluated, including the use of interval selection procedures such as iPLS and CSMWPLS. PLS regression with full-range (650-4000 cm(-1)), second derivative of the spectra and phloroglucinolysis as the reference method gave the most accurate determination for tannin concentration (RMSEC = 2.6%, RMSEP = 9.4%, r = 0.995). The prediction of the mean degree of polymerization (mDP) of the tannins also gave a reasonable prediction (RMSEC = 6.7%, RMSEP = 10.3%, r = 0.958). These results represent the first step in the development of a spectroscopic methodology for the quantification of several phenolic compounds that are critical for wine quality.

A new alkaloid from Portulaca oleracea L. and its antiacetylcholinesterase activity.

PubMed

Xiu, Fen; Li, Xuetao; Zhang, Wenjie; He, Fan; Ying, Xixiang; Stien, Didier

2018-04-18

A new alkaloid, (10E, 12E)-9-ureidooctadeca-10, 12-dienoic acid, named oleraurea (1) and 10 known compounds, p-hydroxybenzaldehyde (2), p-hydroxybenzoic acid (3), p-hydroxyacetophenone (4), benzamide (5), (E)-p-coumaramide (6), (E)-ferulamide (7), soyalkaloid A (8), β-carboline-3-carboxylic acid (9), 2, 3, 4, 9-tetrahydro-1H-pyrido [3, 4-b] indole-3-carboxylic acid (10), (1S, 3S)-1-methyl-1, 2, 3, 4-tetrahydro-β-carboline-3-carboxylic acid (11) were obtained from Portulaca oleracea L., in which, compounds 4, 5, 8-11 were isolated from the plant for the first time. The structure of the compound 1 was identified using spectroscopic methods including 1D and 2D NMR, HR-ESI-TOF-MS. The compounds 1, 5-11 presented anticholinesterase activities, but the P. oleracea extract (POE) presented very low anticholinesterase activity.

Ganoboninketals A-C, Antiplasmodial 3,4-seco-27-Norlanostane Triterpenes from Ganoderma boninense Pat.

PubMed

Ma, Ke; Ren, Jinwei; Han, Junjie; Bao, Li; Li, Li; Yao, Yijian; Sun, Chen; Zhou, Bing; Liu, Hongwei

2014-08-22

Three new nortriterpenes, ganoboninketals A-C (1-3), featuring rearranged 3,4-seco-27-norlanostane skeletons and highly complex polycyclic systems were isolated from the medicinal mushroom Ganoderma boninense. The structures of the new metabolites were established by spectroscopic methods. The absolute configurations in 1-3 were assigned by electronic circular dichroism (ECD) calculations. Compounds 1-3 showed antiplasmodial activity against Plasmodium falciparum with IC50 values of 4.0, 7.9, and 1.7 μM, respectively. Compounds 1 and 3 also displayed weak cytotoxicity against A549 cell line with IC50 values of 47.6 and 35.8 μM, respectively. Compound 2 showed weak cytotoxicity toward HeLa cell line with an IC50 value of 65.5 μM. Compounds 1-3 also presented NO inhibitory activity in the LPS-induced macrophages with IC50 values of 98.3, 24.3, and 60.9 μM, respectively.

Three new diphenyl ether derivatives from the fermentation products of an endophytic fungus Phomopsis fukushii.

PubMed

Gao, Yu-Hong; Zheng, Rui; Li, Jing; Kong, Wei-Song; Liu, Xin; Ye, Lin; Mi, Qi-Li; Kong, Wei-Song; Zhou, Min; Yang, Guang-Yu; Hu, Qiu-Fen; Du, Gang; Yang, Hai-Ying; Li, Xue-Mei

2018-01-17

Three new diphenyl ethers (1-3), together with four known isopentylated diphenyl ethers derivatives (4-7), were isolated from the fermentation products of an endophytic fungus Phomopsis fukushii. Their structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compounds 1-3 were evaluated for their anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) activity. The results revealed that compounds 1 and 2 showed strong inhibitions with inhibition zone diameters (IZD) of 20.2 ± 2.5 mm and 17.9 ± 2.2 mm, respectively. Compound 3 also showed good inhibition with IZD 15.2 ± 1.8 mm. The IZD data of compound 1 is close to that of positive control with IZD 21.9 ± 2.1 mm.

Novel aldehyde and thiosemicarbazone derivatives: Synthesis, spectroscopic characterization, structural studies and molecular docking studies

NASA Astrophysics Data System (ADS)

Karakurt, Tuncay; Tahtaci, Hakan; Subasi, Nuriye Tuna; Er, Mustafa; Ağar, Erbil

2016-12-01

In this study our purpose is that, synthesis and characterization of compounds containing the aldehyde and thiosemicarbazone groups and comparison of the theoretical results with the experimental results. The structures of all synthesized compounds were elucidated by IR, 1H NMR, 13C NMR, elemental analyses techniques. The structure of compound (4) (C9H8N4O2S) was also elucidated by X-ray diffraction analysis. In addition, the theoretical IR spectrum, 1H NMR and 13C NMR chemical shift values, frontier molecular orbital values (FMO) of these molecules were analyzed by using Becke-3- Lee-Yang-Parr (B3LYP) method with LanL2DZ basis set. Finally, molecular docking studies were performed on synthesized compounds using the 4DKI beta-lactam protein structure to determine the potential binding mode of inhibitors.

Polyprenylated polycyclic acylphloroglucinol: Angiogenesis inhibitor from Garcinia multiflora.

PubMed

Cheng, Lin-Yang; Chen, Chun-Lin; Kuo, Yueh-Hsiung; Chang, Tsung-Hsien; Lin, I-Wei; Wang, Shih-Wei; Chung, Mei-Ing; Chen, Jih-Jung

2018-06-01

A new polyprenylated polycyclic acylphloroglucinol, garcimultiflorone K (1), has been isolated from the stems of Garcinia multiflora, together with two known compounds, garcimultiflorone A (2) and garcimultiflorone B (3). The structure of new compound 1 was determined through spectroscopic methods including 1D and 2D NMR and MS analyses. The anti-angiogenic and anti-cancer effects of compounds 1-3 were evaluated in human endothelial progenitor cells (EPCs) and cancer cells. Of these, garcimultiflorone K (1) displayed the most potent anti-angiogenic property by suppressing cell growth and tube formation of EPCs. Compound 1 also exhibited growth-inhibitory activities against human hepatocellular carcinoma cell line SK-Hep-1 and hormone refractory prostate cancer cell line PC-3 with GI 50 values of 4.3 ± 1.6 and 6.6 ± 0.4 μM, respectively. Copyright © 2018 Elsevier Ltd. All rights reserved.

Anti-inflammatory and cytotoxic neoflavonoids and benzofurans from Pterocarpus santalinus.

PubMed

Wu, Shou-Fang; Chang, Fang-Rong; Wang, Sheng-Yang; Hwang, Tsong-Long; Lee, Chia-Lin; Chen, Shu-Li; Wu, Chin-Chung; Wu, Yang-Chang

2011-05-27

Five new benzofurans, pterolinuses A-E (1-5), six new neoflavonoids, pterolinuses F-J (8-13), and five known compounds (6, 7, 14-16) were isolated from an extract of Pterocarpus santalinus heartwood. All new structures were elucidated by spectroscopic methods, and configurations were confirmed by CD spectral data and optical rotation values. The isolates were evaluated for anti-inflammatory and cytotoxic activities. Six compounds (1, 2, 4, 6, 7, and 15) showed significant inhibition in at least one anti-inflammatory assay. Compound 2 showed the best selective effect against superoxide anion generation in human neutrophils with, an IC50 value of 0.19 μg/mL, and was 6.2-fold more potent than the positive control LY294002. Compound 14 showed the highest cytotoxicity against Ca9-22 cancer cells, with an IC50 value of 0.46 μg/mL.

Flavonoids and stilbenoids from Derris eriocarpa.

PubMed

Zhang, Hong-Xia; Lunga, Paul-Keilah; Li, Zhi-Jian; Dai, Qin; Du, Zhi-Zhi

2014-06-01

One new resveratrol analogue, 1-(3',4',5'-trimethoxyphenyl)-2-methoxy-2-(4″-methoxyphenyl)-ethane-1-ol (1), and two new prenylisoflavones, 4'-hydroxy-5,7-dimethoxy-6-(3-methyl-2-butenyl)-isoflavone (2), and derrubon 5-methyl ether (3), together with 17 known compounds including one new natural product, 5,7-dihydroxy-3-[4'-O-(3-methyl-2-butenyl)-phenyl]-isoflavone (4), were isolated from the stems of ethnomedicinal plant Derris eriocarpa How. (Leguminosae). Their structures were elucidated based on chemical evidence and spectroscopic techniques including two-dimensional NMR methods. All compounds are reported from this species for the first time. Antimicrobial activities of the new compounds were evaluated. Compound 2 exhibited good inhibitory activities against Candida guilliermondii, C. albicans and Microsporium gypseum with the minimal inhibitory concentration (MIC) values of 12.5 μg/ml. Copyright © 2014 Elsevier B.V. All rights reserved.

A new rearranged abietane diterpene and other constituents from Clerodendrum philipinum.

PubMed

Van Oanh, Ha; Sinh, Pham Xuan; An, Nguyen Thai; Hung, Ta Manh; Huong, Tran Thi Lan; Que, Do Thi Nguyet; Thao, Nguyen Phuong; Cuong, Nguyen Xuan; Dat, Nguyen Tien; Minh, Chau Van; Kiem, Phan Van

2009-03-01

From the methanolic extract of the roots of Clerodendrum philipinum, a new rearranged abietane diterpene (1) and eight known compounds were isolated by various chromatography methods. Their structures were identified by means of spectroscopic methods, including 1D- and 2D-NMR, as 17(15-->16),18(4-->3)-bisabeo-11,12,14,16-tetrahydroxy-3,5,8,11,13,15-abietahexaen-7-one (1), binankadsurin A, clerodenoside A, martynoside, acteoside, isoacteoside, astragalin, p3-sitosterol, and daucosterol. Binankadsurin A was found for the first time from a Clerodendrum species.

Pretrichodermamides D-F from a Marine Algicolous Fungus Penicillium sp. KMM 4672.

PubMed

Yurchenko, Anton N; Smetanina, Olga F; Ivanets, Elena V; Kalinovsky, Anatoly I; Khudyakova, Yuliya V; Kirichuk, Natalya N; Popov, Roman S; Bokemeyer, Carsten; von Amsberg, Gunhild; Chingizova, Ekaterina A; Afiyatullov, Shamil Sh; Dyshlovoy, Sergey A

2016-06-27

Three new epidithiodiketopiperazines pretrichodermamides D-F (1-3), together with the known N-methylpretrichodermamide B (4) and pretrichodermamide С (5), were isolated from the lipophilic extract of the marine algae-derived fungus Penicillium sp. KMM 4672. The structures of compounds 1-5 were determined based on spectroscopic methods. The absolute configuration of pretrichodermamide D (1) was established by a combination of modified Mosher's method, NOESY data, and biogenetic considerations. N-Methylpretrichodermamide B (5) showed strong cytotoxicity against 22Rv1 human prostate cancer cells resistant to androgen receptor targeted therapies.

The reaction of formic acid with RaneyTM copper

NASA Astrophysics Data System (ADS)

Callear, Samantha K.; Silverwood, Ian P.; Chutia, Arunabhiram; Catlow, C. Richard A.; Parker, Stewart F.

2016-04-01

The interaction of formic acid with RaneyTM Cu proves to be complex. Rather than the expected generation of a monolayer of bidentate formate, we find the formation of a Cu(II) compound. This process occurs by direct reaction of copper and formic acid; in contrast, previous methods are by solution reaction. This is a rare example of formic acid acting as an oxidant rather than, as more commonly found, a reductant. The combination of diffraction, spectroscopic and computational methods has allowed this unexpected process to be characterized.

Preparation, isolation, and characterization of cutin monomers and oligomers from tomato peels.

PubMed

Osman, S F; Irwin, P; Fett, W F; O'Connor, J V; Parris, N

1999-02-01

Cutin in tomato peels was depolymerized in methanolic base to yield cutin monomers or a mixture of cutin oligomers. These products were isolated by typical solvent extraction methods or by precipitation, and the isolates were characterized by chromatographic and spectroscopic analyses. It was determined that the compositions of the isolates from both isolation procedures were similar, although solvent extraction gave higher yields. However, the precipitation method, which is easy to carry out and avoids the use of undesirable organic solvents, may be preferable in commercial processes for recovering these compounds.

Prenylated flavonoids from Desmodium caudatum and evaluation of their anti-MRSA activity.

PubMed

Sasaki, Hisako; Kashiwada, Yoshiki; Shibata, Hirofumi; Takaishi, Yoshihisa

2012-10-01

Seven prenylated flavonoids and a prenylated chromanochroman derivative, together with eight known flavonoids, were isolated from roots of Desmodium caudatum. The 15 structures were elucidated by extensive spectroscopic analyses. The antibacterial activity of many of other compounds was evaluated against methicillin-resistant Staphylococcus aureus (MRSA: COL and 5) by a disc diffusion method, and the minimum inhibitory concentrations (MICs) to MRSA were determined. Copyright © 2012 Elsevier Ltd. All rights reserved.

Spectroscopic and computational study of a new isomer of salinomycin

NASA Astrophysics Data System (ADS)

Pankiewicz, Radosław

2013-09-01

A new derivative of polyether ionophore salinomycin was obtained as a result of a rearrangement catalysed by sulphuric acid in two-phase medium of water/methylene chloride solution. The new isomer was fully characterized by multinuclear 2D NMR, NOESY and MALDI-TOF. The properties of the new compound were additionally study by semiempirical (PM5) and DFT (B3LYP) methods. A potential mechanism of the rearrangement was also proposed.

Soulieoside O, a new cyclolanostane triterpenoid glycoside from Souliea vaginata.

PubMed

Wu, Hai-Feng; Li, Peng-Fei; Zhu, Yin-Di; Zhang, Xiao-Po; Ma, Guo-Xu; Xu, Xu-Dong; Liu, Yi-Lin; Luo, Zheng-Hong; Chen, Di-Zhao; Zou, Qiong-Yu; Zhao, Zi-Jian

2017-12-01

A new cyclolanostane triterpenoid glycoside, soulieoside O (1), together with 25-O-acetylcimigenol-3-O-β-d-xylopyranoside (2) and cimigenol-3-O-β-d-xylopyranoside (3), was isolated from the rhizomes of Souliea vaginata. Their structures were characterized by spectroscopic analysis and chemical methods. The new compound showed moderate inhibitory activity against three human cancer cell lines with IC 50 values of 9.3-22.5 μM.

A novel 1,10-seco withanolide from Physalis peruviana.

PubMed

Fang, Sheng-Tao; Liu, Ji-Kai; Li, Bo

2010-07-01

A novel 1,10-seco withanolide, 1,10-seco withaperuvin C (1), together with four known withanolides, 4 beta-hydroxywithanolide E (2), visconolide (3), withanolide F (4), and withaphysanolide (5), was isolated from the aerial parts of Physalis peruviana. The structures of compounds 1-5 were determined on the basis of spectroscopic methods including extensive 1D and 2D NMR analysis. In addition, the possible biogenetic relationships among these five withanolides are discussed.

Effects of styrene unit on molecular conformation and spectral properties of CNsbnd PhCHdbnd NPhCHdbnd CHPhsbnd CN

NASA Astrophysics Data System (ADS)

Fang, Zhengjun; Wu, Feng; Jiao, Yingchun; Wang, Nanfang; Au, Chaktong; Cao, Chenzhong; Yi, Bing

2018-05-01

Compound CN-PhCH=NPhCH=CHPh-CN with both stilbene and benzylidene aniline units was synthesized, and studied from the viewpoint of molecular conformation and spectroscopic property by a combined use of experimental and computational methods. The maximum UV absorption wavelength (λmax) of the compound in ethanol, acetonitrile, chloroform and cyclohexane solvents were measured, and the 13C NMR chemical shift value δC(Cdbnd N) in chloroform-d was determined. The crystal structure of the compound was determined by X-ray diffraction. The frontier molecular orbital was calculated by density functional theory method. The results show that the UV absorption spectrum of the titled compound is similar to those of Schiff bases, while there is a larger red shift of λmax comparing to that of CN-PhCH=NPh-CN. Moreover, the molecular configuration of the titled compound relative to Cdbnd N is anti-form, having a more obvious twisted structure. The spectral and structural behaviors are further supported by the results of frontier molecular orbital analyses, NBO, electrostatic potentials and TD-DFT calculations. The study provides deeper insights into the molecular conformation of Schiff bases.

Increasing selectivity for TNT-based explosive detection by synchronous luminescence and derivative spectroscopy with quantum yields of selected aromatic amines.

PubMed

Sheaff, Chrystal N; Eastwood, Delyle; Wai, Chien M

2007-01-01

The detection of explosive material is at the forefront of current analytical problems. A detection method is desired that is not restricted to detecting only explosive materials, but is also capable of identifying the origin and type of explosive. It is essential that a detection method have the selectivity to distinguish among compounds in a mixture of explosives. The nitro compounds found in explosives have low fluorescent yields or are considered to be non-fluorescent; however, after reduction, the amino compounds exhibit relatively high fluorescence. We discuss how to increase selectivity of explosive detection using fluorescence; this includes synchronous luminescence and derivative spectroscopy with appropriate smoothing. By implementing synchronous luminescence and derivative spectroscopy, we were able to resolve the reduction products of one major TNT-based explosive compound, 2,4-diaminotoluene, and the reduction products of other minor TNT-based explosives in a mixture. We also report for the first time the quantum yields of these important compounds. Relative quantum yields are useful in establishing relative fluorescence intensities and are an important spectroscopic measurement of molecules. Our approach allows for rapid, sensitive, and selective detection with the discrimination necessary to distinguish among various explosives.

Mechanism and applications of new fluorescent compounds produced by femtosecond laser surgery in biological tissue (Conference Presentation)

NASA Astrophysics Data System (ADS)

Qu, Jianan Y.; Sun, Qiqi

2017-02-01

The single or multi-photon microscopy based on fluorescent labelling and staining is a sensitive and quantitative method that is widely used in molecular biology and medical research for a variety of experimental, analytical, and quality control applications. However, label-free method is highly desirable in biology and medicine when performing long term live imaging of biological system and obtaining instant tissue examination during surgery procedures. Recently, our group found that femtosecond laser surgery turned a variety of biological tissues and protein samples into highly fluorescent substances. The newly formed fluorescent compounds produced during the laser surgery can be excited via single- and two-photon processes over broad wavelength ranges. We developed a combined confocal and two-photon spectroscopic microscope to characterize the fluorescence from the new compound systematically. The structures of the femtosecond laser treated tissue were studied using Raman spectroscopy and transmission electron microscopy. Our study revealed the mechanisms of the fluorescence emission form the new compound. Furthermore, we demonstrated the applications of the fluorescent compounds for instant evaluation of femtosecond laser microsurgery, study of stem cell responses to muscle injury and neuro-regeneration after spinal cord injury.

Synthesis, structural characterization and dielectric behavior of new oxime-cyclotriphosphazene derivatives

NASA Astrophysics Data System (ADS)

Koran, Kenan; Özen, Furkan; Biryan, Fatih; Görgülü, Ahmet Orhan

2016-02-01

The cyclotriphosphazene compound (2) bearing formyl groups as side groups was obtained from the reaction of 2,2-Dichloro-4,4,6,6-bis[spiro(2‧,2″-dioxy-1‧,1″-biphenylyl)]cyclotriphosphazene (1) with 4-hydroxy-3-methoxybenzaldehyde in the presence K2CO3 in tetrahydrofuran. Oxime-cyclotriphosphazene compound (3) was synthesized from the reaction of compound 2 with hydroxylamine hydrochloride in pyridine. The synthesized oxime-phosphazene compound (3) was reacted with alkyl and acyl halides. As a results, the cyclotriphosphazene compounds (1-10) bearing oxime ether and ester as side groups were obtained. The chemical structures of these compounds (1-10) were determined by elemental analysis, FT-IR, 1H, 13C and 31P NMR spectroscopic methods. Dielectric constant, dielectric loss factors and conductivity properties of cyclotriphosphazene compounds were measured over the frequency range from 100 Hz to 2 kHz at 25 °C and compared with each other. It is found that ester substituted cyclotriphosphazenes have higher dielectric constant. Our study suggests that these phosphazenes promising candidate materials in multifunctional optoelectronic devices.

1-(4-(6-Fluorobenzo [d] isoxazol-3-yl) piperidin-1-yl)-2-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl) ethanone: Synthesis, spectroscopic characterization, Hirshfeld surface analysis, cytotoxic studies and docking studies

NASA Astrophysics Data System (ADS)

Govindhan, M.; Viswanathan, V.; Karthikeyan, S.; Subramanian, K.; Velmurugan, D.

2017-08-01

Compound 1-(4-(6-fluorobenzo[d] isoxazol-3-yl) piperidin-1-yl)-2-(4-(hydroxymethyl)-1H-1, 2,3-triazol-1-yl) ethanone was synthesized in good yield by using click chemistry approach with 2-azido-1-(4-(6-flurobenzo[d]isooxazol-3-yl)piperidin-1-yl)ethanone as a starting material. The synthesized compound was characterized using IR, NMR and MS studies. Thermal stability of the compound was analyzed by using TGA and DSC technique. The single crystal XRD analysis was taken part, to confirm the structure of the compound. The intercontacts in the crystal structure are analyzed using Hirshfeld surfaces computational method. Cytotoxicity of the synthesized compound was evaluated and the results were reported. The binding analysis carried out between the newly synthesized molecule with human serum albumin using fluorescence spectroscopy technique to understand the pharmacokinetics nature of the compound for further biological application. The molecular docking studies were evaluated for the compound to elucidate insights of new molecules in carrier protein.

Spectroscopic, structural characterizations and antioxidant capacity of the chromium (III) niacinamide compound as a diabetes mellitus drug model

NASA Astrophysics Data System (ADS)

Refat, Moamen S.; El-Megharbel, Samy M.; Hussien, M. A.; Hamza, Reham Z.; Al-Omar, Mohamed A.; Naglah, Ahmed M.; Afifi, Walid M.; Kobeasy, Mohamed I.

2017-02-01

New binuclear chromium (III) niacinamide compound with chemical formula [Cr2(Nic)(Cl)6(H2O)4]·H2O was obtained upon the reaction of chromium (III) chloride with niacinamide (Nic) in methanol solvent at 60 °C. The proposed structure was discussed with the help of microanalytical analyses, conductivity, spectroscopic (FT-IR and UV-vis.), magnetic calculations, thermogravimetric analyses (TG/TGA), and morphological studies (X-ray of solid powder and scan electron microscopy. The infrared spectrum of free niacinamide in comparison with its chromium (III) compound indicated that the chelation mode occurs via both nitrogen atoms of pyridine ring and primary -NH2 group. The efficiency of chromium (III) niacinamide compound in decreasing of glucose level of blood and HbA1c in case of diabetic rats was checked. The ameliorating gluconeogenic enzymes, lipid profile and antioxidant defense capacities are considered as an indicator of the efficiency of new chromium (III) compound as antidiabetic drug model.

Synthesis, analgesic, anti-inflammatory and anti-ulcerogenic activities of certain novel Schiff's bases as fenamate isosteres.

PubMed

Alafeefy, Ahmed M; Bakht, Mohammed A; Ganaie, Majid A; Ansarie, Mohd N; El-Sayed, Nahed N; Awaad, Amani S

2015-01-15

A series of certain novel Schiff bases as fenamate isosteres (VI:a-k) were synthesized to locate analgesic, anti-inflammatory agent with minimal ulcerogenic potential. The structures of the newly synthesized compounds were elucidated on the basis of their elemental analysis as well as IR, and NMR and mass spectroscopic data. All the compounds were evaluated for their anti-inflammatory activity by carrageenan induced paw oedema method. The compounds possessing good anti-inflammatory activity were further tested for analgesic, ulcerogenic, lipid peroxidation potentials and liver toxicity. Compounds (VI-c), (VI-f), (VI-h) and (VI-i) showed the best anti-inflammatory and significant analgesic activities at doses comparable to that of the standard drug Indomethacin. However, compounds (VI-c) and (VI-f) could be considered the most potent anti-inflammatory and analgesic molecules with maximum reduction in gastro-intestinal ulceration with no hepatocyte necrosis or liver degeneration. Copyright © 2014 Elsevier Ltd. All rights reserved.

Structural, spectroscopic and electronic properties of hydrogen-bonded water molecules in crystals. Ab initio calculations and experimental data of MC1 2· n(H,D) 2O, M = Sr or Ba

NASA Astrophysics Data System (ADS)

Möller, H.; Niu, J. E.; Lutz, H. D.; Schwarz, W. H. E.

1997-12-01

Structural, spectroscopic and electronic properties of (more or less deuterated) water molecules in the crystal fields of SrCl 2·2H 2O, SrCl 2·H 2O and BaCl 2·H 2O, previously investigated by experimental techniques, were calculated by ab initio SCF-MP methods. The H 2O molecules of each compound are asymmetrically surrounded by three adjacent chloride ions, one hydrogen atom being attached to a nearby Cl -, the other less perturbed hydrogen atom bridging the two less near Cl -. The diversity of structural and spectroscopic features found experimentally, for instance the trends from free H 2O to H 2O in BaCl 2·H 2OSrCl 2·H 2OSrCl 2·2H 2O, are well reproduced by the model calculations, which provide the correct assignment and physical interpretation. The differences between the compounds and the asymmetry of the hydrate water molecules can be rationalized with the help of crystal fields. The crystal environment expands the internuclear distances of H 2O by up to 3 pm. The change of vibrational frequencies can be explained qualitatively by only taking the coupling and anharmonicity of the free water molecule and its modified structure in the crystals into account. The infra-red intensities, however, are strongly influenced by the electronic polarization.

Quantum mechanical and spectroscopic (FT-IR, 13C, 1H NMR and UV) investigations of 2-(5-(4-Chlorophenyl)-3-(pyridin-2-yl)-4,5-dihydropyrazol-1-yl)benzo[d]thiazole by DFT method.

PubMed

Diwaker

2014-07-15

The electronic, NMR, vibrational, structural properties of a new pyrazoline derivative: 2-(5-(4-Chlorophenyl)-3-(pyridine-2-yl)-4,5-dihydropyrazol-1-yl)benzo[d]thiazole has been studied using Gaussian 09 software package. Using VEDA 4 program we have reported the PED potential energy distribution of normal mode of vibrations of the title compound. We have also reported the (1)H and (13)C NMR chemical shifts of the title compound using B3LYP level of theory with 6-311++G(2d,2p) basis set. Using time dependent (TD-DFT) approach electronic properties such as HOMO and LUMO energies, electronic spectrum of the title compound has been studied and reported. NBO analysis and MEP surface mapping has also been calculated and reported using ab initio methods. Copyright © 2014 Elsevier B.V. All rights reserved.

[Determination of longistylin A and longistylin C in Cajanus cajan].

PubMed

Wang, Dawu; Xiao, Minxun; Li, Yirong; Shen, Xiaoling; Lu, Yuanyuan; Liu, Kanglun; Li, Zhenghong; Hu, Yingjie

2011-10-01

To establish quality control criteria for medicinal herb Cajanus cajan based on the determination of longistylin A and longistylin C, two bioactive and specific stilbenes of the plant. Longistylin A and longistylin C were obtained from the leaves of C. cajan by silica gel column chromatography and identified as marker compounds of this plant by spectroscopic analysis. A RP-HPLC method was established to determine the two compounds. Longistylin A and longistylin C were well separated on a Thermo BDS Hypersil C18 column (4.6 mm x 250 mm, 5 microm) with a mobile phase methanol-water (8:2), and showed good linearity in the range of 0.00288 - 0.0576 microg and 0.0112 - 0.224 microg, respectively. The average recoveries were 98.9% and 97.2% with RSD of 2.4% and 2.2% for these two compounds, respectively. The established analysis method is simple and accurate, whicn can be used for quality control of C. cajan.

Synthesis, molecular structure and spectroscopic investigations of novel fluorinated spiro heterocycles.

PubMed

Islam, Mohammad Shahidul; Al-Majid, Abdullah Mohammed; Barakat, Assem; Soliman, Saied M; Ghabbour, Hazem A; Quah, Ching Kheng; Fun, Hoong-Kun

2015-05-07

This paper describes an efficient and regioselective method for the synthesis of novel fluorinated spiro-heterocycles in excellent yield by cascade [5+1] double Michael addition reactions. The compounds 7,11-bis(4-fluorophenyl)-2,4-dimethyl- 2,4-diazaspiro[5.5] undecane-1,3,5,9-tetraone (3a) and 2,4-dimethyl-7,11-bis (4-(trifluoromethyl)phenyl)-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone (3b) were characterized by single-crystal X-ray diffraction, FT-IR and NMR techniques. The optimized geometrical parameters, infrared vibrational frequencies and NMR chemical shifts of the studied compounds have also been calculated using the density functional theory (DFT) method, using Becke-3-Lee-Yang-Parr functional and the 6-311G(d,p) basis set. There is good agreement between the experimentally determined structural parameters, vibrational frequencies and NMR chemical shifts of the studied compounds and those predicted theoretically. The calculated natural atomic charges using NBO method showed higher polarity of 3a compared to 3b.The calculated electronic spectra are also discussed based on the TD-DFT calculations.

MULTISPECTRAL IDENTIFICATION OF POTENTIALLY HAZARDOUS BYPRODUCTS OF OZONATION AND CHLORINATION - PART I: STUDIES OF CHROMATOGRAPHIC AND SPECTROSCOPIC PROPERTIES OF MX

EPA Science Inventory

The gas chromatographic (GC) and Fourier transform infrared and mass spectroscopic (FT-IR and MS, respectively) properties of (Z)-2-chloro-3-(dichloromethyl)4-oxobutenoic acid (MX) (a highly mutagenic byproduct of drinking water chlorination) and several related compounds were st...

Chemistry WebBook

National Institute of Standards and Technology Data Gateway

SRD 69 NIST Chemistry WebBook (Web, free access)   The NIST Chemistry WebBook contains: Thermochemical data for over 7000 organic and small inorganic compounds; thermochemistry data for over 8000 reactions; IR spectra for over 16,000 compounds; mass spectra for over 33,000 compounds; UV/Vis spectra for over 1600 compounds; electronic and vibrational spectra for over 5000 compounds; constants of diatomic molecules(spectroscopic data) for over 600 compounds; ion energetics data for over 16,000 compounds; thermophysical property data for 74 fluids.

A comparative experimental and quantum chemical study on monomeric and dimeric structures of 3,5-dibromoanthranilic acid.

PubMed

Karabacak, Mehmet; Cinar, Mehmet

2012-10-01

This study presents the structural and spectroscopic characterization of 3,5-dibromoanthranilic acid with help of experimental techniques (FT-IR, FT-Raman, UV, NMR) and quantum chemical calculations. The vibrational spectra of title compound were recorded in solid state with FT-IR and FT-Raman in the range of 4000-400 and 4000-50 cm(-1), respectively. The vibrational frequencies were also computed using B3LYP method of DFT with 6-311++G(d,p) basis set. The fundamental assignments were done on the basis of the total energy distribution (TED) of the vibrational modes, calculated with scaled quantum mechanical (SQM) method. The (1)H, (13)C and DEPT NMR spectra were recorded in DMSO solution and calculated by gauge-invariant atomic orbitals (GIAO) method. The UV absorption spectra of the compound were recorded in the range of 200-400 nm in ethanol, water and DMSO solutions. Solvent effects were calculated using time-dependent density functional theory and CIS method. The ground state geometrical structure of compound was predicted by B3LYP method and compared with the crystallographic structure of similar compounds. All calculations were made for monomeric and dimeric structure of compound. Moreover, molecular electrostatic potential (MEP) and thermodynamic properties were performed. Mulliken atomic charges of neutral and anionic form of the molecule were computed and compared with anthranilic acid. Copyright © 2012 Elsevier B.V. All rights reserved.

Synthesis of New Hydrazone Derivatives for MAO Enzymes Inhibitory Activity.

PubMed

Can, Nafiz Öncü; Osmaniye, Derya; Levent, Serkan; Sağlık, Begüm Nurpelin; İnci, Beril; Ilgın, Sinem; Özkay, Yusuf; Kaplancıklı, Zafer Asım

2017-08-20

In the present work, 14 new 1-substituted-2-phenylhydrazone derivatives were synthesized to evaluate their inhibitory activity against hMAO enzymes. The structures of the newly synthesized hydrazones 2a-2n were characterized by IR, 1H-NMR, 13C-NMR, HR-MS spectroscopic methods. The inhibitory activity of compounds 2a-2n against hMAO-A and hMAO-B enzymes was elucidated by using an in-vitro Amplex Red® reagent assay based on fluorometric methods. According to the activity studies, 2a and 2b were found to be the most active compounds against hMAO-A enzyme, with IC50 values of 0.342 µM and 0.028 µM, respectively. The most active compounds 2a-2b were evaluated by means of enzyme kinetics and docking studies. Moreover, these compounds were subjected to cytotoxicity and genotoxicity tests to establish their preliminary toxicological profiles and were found to be non-cytotoxic and non-genotoxic. Consequently, the findings of this study display the biological importance of compounds 2a, 2b as selective, irreversible and competitive inhibitors of hMAO-A. Docking studies revealed that there is a strong interaction between hMAO-A and the most active compound 2b.

Spectroscopic (FT-IR and UV-Vis) and theoretical (HF and DFT) investigation of 2-Ethyl-N-[(5-nitrothiophene-2-yl)methylidene]aniline

NASA Astrophysics Data System (ADS)

Ceylan, Ümit; Tarı, Gonca Özdemir; Gökce, Halil; Ağar, Erbil

2016-04-01

Crystal structure of the title compound, 2-Ethyl-N-[(5-nitrothiophene-2-yl)methylidene]aniline, C13H12N2O2S, has been synthesized and characterized by FT-IR and UV-Vis spectrum. The compound crystallized in the monoclinic space group P 21/c with a = 11.3578 (4) Å, b = 7.4923 (2) Å, c = 14.9676 (6) Å and β = 99.589 (3)° and Z = 4 in the unit cell. The molecular geometry was also calculated using the Gaussian 03 software and structure was optimized using the HF and DFT/B3LYP methods with the 6-311++G(d,p) basis set in ground state. Using the TD-DFT method, the electronic absorption spectra of the title compound was computed in both the gas phase and ethanol solvent. The harmonic vibrational frequencies of the title compound were calculated using the same methods with the 6-311++G(d,p) basis set. The calculated results were compared with the experimental determination results of the compound. It was seen that the optimized structure was in excellent agreement with the X-ray crystal structure. The energetic behaviors of the title compound in solvent media were examined using the HF and DFT/B3LYP methods with the 6-311++G(d,p) basis set applying the polarizable continuum model (PCM). In addition, the molecular orbitals (FMOs) analysis, molecular electrostatic potential (MEP), nonlinear optical and thermodynamic properties of the title compound were performed using the same methods with the 6-311++G(d,p) basis set.

Synthesis, spectroscopic (FT-IR, FT-Raman, UV and NMR) and computational studies on 3t-pentyl-2r,6c-diphenylpiperidin-4-one semicarbazone

NASA Astrophysics Data System (ADS)

Arockia doss, M.; Savithiri, S.; Rajarajan, G.; Thanikachalam, V.; Saleem, H.

2015-09-01

The structural and spectroscopic studies of 3t-pentyl-2r,6c-diphenylpiperidin-4-one semicarbazone (PDPOSC) were made by adopting B3LYP/HF levels theory using 6-311++G(d,p) basis set. The FT-IR and Raman spectra were recorded in solid phase, the fundamental vibrations were assigned on the basis of the total energy distribution (TED) of the vibrational modes, calculated with scaled quantum mechanics (SQM) method and PQS program. DFT method indicates that B3LYP is superior to HF method for molecular vibrational analysis. UV-vis spectrum of the compound was recorded in different solvents in the region of 200-800 nm and the electronic properties such as excitation energies, oscillator strength, wavelengths, HOMO and LUMO energies were evaluated by time-dependent DFT (TD-DFT) approach. The polarizability and first order hyperpolarizability of the title molecule were calculated and interpreted. The hyperconjugative interaction energy (E(2)) and electron densities of donor (i) and acceptor (j) bonds were calculated using NBO analysis. In addition, MEP and atomic charges of carbon, nitrogen and oxygen were calculated using B3LYP/6-311++G(d,p) level theory. Moreover, thermodynamic properties of the title compound were calculated by B3LYP/HF, levels using 6-311++G(d,p) basis set. The 1H and 13C nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by the gauge independent atomic orbital (GIAO) method and compared with experimental results.

Three new fatty acid esters from the mushroom Boletus pseudocalopus.

PubMed

Kim, Ki Hyun; Choi, Sang Un; Lee, Kang Ro

2012-06-01

A bioassay-guided fractionation and chemical investigation of a MeOH extract of the Korean wild mushroom Boletus pseudocalopus resulted in the identification of three new fatty acid esters, named calopusins A-C (1-3), along with two known fatty acid methyl esters (4-5). These new compounds are structurally unique fatty acid esters with a 2,3-butanediol moiety. Their structures were elucidated through 1D- and 2D-NMR spectroscopic data and GC-MS analysis as well as a modified Mosher's method. The new compounds 1-3 showed significant inhibitory activity against the proliferation of the tested cancer cell lines with IC(50) values in the range 2.77-12.51 μM.

Isolation of bioactive and other oxoaporphine alkaloids from two annonaceous plants, Xylopia aethiopica and Miliusa cf. banacea.

PubMed

Harrigan, G G; Gunatilaka, A A; Kingston, D G; Chan, G W; Johnson, R K

1994-01-01

The oxoaporphine alkaloids oxophoebine [1] and liriodenine [2] have been isolated from Xylopia aethiopica (Annonaceae). Both showed selective toxicity against DNA repair and recombination deficient mutants of the yeast Saccharomyces cerevisae. Three related but inactive compounds, oxoglaucine [3], O-methylmoschatoline [4], and lysicamine [5], were also isolated from this plant. Selective toxicity was also observed for 10-methoxyliriodenine (lauterine) [6] and 10-hydroxyliriodenine [7], two oxoaporphine alkaloids isolated from Miliusa cf. banacea (Annonaceae). The structure of 10-hydroxyliriodenine [7], a novel oxoaporphine, was determined by spectroscopic methods and chemical conversion to compound 6. The role of the bioactive oxoaporphine alkaloids as DNA topoisomerase inhibitors is discussed.

Four new triterpenoids from the leaves of Psidium guajava.

PubMed

Shao, Meng; Wang, Ying; Huang, Xiao-Jun; Fan, Chun-Lin; Zhang, Qing-Wen; Zhang, Xiao-Qi; Ye, Wen-Cai

2012-01-01

Four new triterpenoids, psiguanins A-D (1-4), along with 13 known ones (5-17), were isolated from the leaves of Psidium guajava. The structures of new compounds were determined as 2α,3β-dihydroxy-taraxer-20-en-28-oic acid (1), 2α,3β,12α,13β-tetrahydroxy-urs-28-oic acid (2), 2α,3β,12β,13β-tetrahydroxy-urs-28-oic acid (3), and 2α,3β,12β,13α-tetrahydroxy-urs-28-oic acid (4), respectively, on the basis of comprehensive spectroscopic methods and molecular modeling calculation. Among them, compound 4 was characterized as an unusual ursane-type triterpenoid with cis-fused C/D ring system.

A field-deployable compound-specific isotope analyzer based on quantum cascade laser and hollow waveguide

NASA Astrophysics Data System (ADS)

Wu, Sheng; Deev, Andrei

2013-01-01

A field deployable Compound Specific Isotope Analyzer (CSIA) coupled with capillary chromatogrpahy based on Quantum Cascade (QC) lasers and Hollow Waveguide (HWG) with precision and chemical resolution matching mature Mass Spectroscopy has been achieved in our laboratory. The system could realize 0.3 per mil accuracy for 12C/13C for a Gas Chromatography (GC) peak lasting as short as 5 seconds with carbon molar concentration in the GC peak less than 0.5%. Spectroscopic advantages of HWG when working with QC lasers, i.e. single mode transmission, noiseless measurement and small sample volume, are compared with traditional free space and multipass spectroscopy methods.

Synthesis, characterization, spectroscopic studies and antimicrobial activity of three new Schiff bases derived from Heterocyclic moiety

NASA Astrophysics Data System (ADS)

Mesbah, Mounira; Douadi, Tahar; Sahli, Farida; Issaadi, Saifi; Boukazoula, Soraya; Chafaa, Salah

2018-01-01

Three new Schiff-bases compounds (I-III) were synthesized by a condensation reaction in 1:2 M ratios of 4,4‧-diaminodiphenyl sulfide and pyrrol/thiophene/furan-2-carboxaldehyde in ethanol. The structural determinations of the Schiff-bases were identified with the help of elemental analysis then confirmed by UV-Vis, FT-IR and 1H NMR. The products were obtained in excellent yields. On the other hand, the in vitro antibacterial and antifungal activities of the synthesized compounds were investigated using disc diffusion method. Schiff bases synthesized individually exhibited varying degrees of inhibitory effects on the growth of the tested microbial species.

Constituents of the root of Anemone tomentosa.

PubMed

Hu, Hao-Bin; Zheng, Xu-Dong; Jian, Yu-Feng; Liu, Jian-Xin; Zhu, Ji-Hua

2011-07-01

A new diterpene glycoside, tomentoside I (1), along with eleven known compounds, including the four coumarins, 4,5-dimethoxyl-7-methylcoumarin (2), 4,7-dimethoxyl-5-methylcoumarin (3), isofraxidin (4) and fraxidin (5) as well as the seven triterpenoids, oleanolic acid (6), oleanolic acid 3-O-α-L-arabinopyranoside (7), oleanolic acid 3-O-β-D-galactopyranosyl-(1→3)-β-D-glucopyranoside (8), hederagenin 3-O-α-L-arabinopyranoside (9), betulinic acid (10), 18-hydroxyursolic acid (11) and 2α,3β,23-trihydroxyurs-12-en-28-oic acid (12) were isolated from the ethanolic extract of the root of Anemone tomentosa and their chemical structures were elucidated by spectroscopic methods. The antimicrobial activities of compounds 1-12 were measured using the agar disc-diffusion method. Also, their antioxidant activities against 1,1-diphenyl-2-picrylhydrazyl (DPPH) were evaluated.

Six New neo-Clerodane Diterpenoids from Aerial Parts of Scutellaria barbata and Their Cytotoxic Activities.

PubMed

Yang, Guo-Chun; Hu, Jia-Hui; Li, Bing-Long; Liu, Huan; Wang, Jia-Yue; Sun, Li-Xin

2018-06-20

Six new neo-clerodane diterpenoids (1: -6: ), scutebatas X - Z, A 1 -C 1 , along with twelve known ones (7: -18: ) were obtained via the phytochemical investigation of the aerial parts of Scutellaria barbata . Their structures were established by detailed spectroscopic analysis. The absolute configurations of 1: and 2: , as the representative members of this type, were identified based on a circular dichroic exciton chirality method. Moreover, in vitro cytotoxicity of compounds 1: -6: were evaluated against three human cancer cell lines (SGC-7901, MCF-7, and A-549) using the MTT method. Compound 6: showed cytotoxic activities against all the three cell lines with IC 50 values of 17.9, 29.9, and 35.7 µM, respectively. Georg Thieme Verlag KG Stuttgart · New York.

A new bioactive diterpenoid from pestalotiopsis adusta, an endophytic fungus from clerodendrum canescens.

PubMed

Xu, Ming-Feng; Jia, Ou-Ya; Wang, Sheng-Jia; Zhu, Qin

2016-02-02

Bioassay-guided fractionation of the culture extract of Pestalotiopsis adusta, an endophytic fungus isolated from the medicinal plant Clerodendrum canescens, led to the isolation of one new, (10S)-12,16-epoxy-17(15→16)-abeo-3,5,8,12,15-abietapentaen-2,7,11,14-tetraone (1), and four known diterpenoids, teuvincenone F (2), uncinatone (3), coleon U (4), coleon U-12-methyl ether (5). These structures were identified by using spectroscopic methods, including UV, MS, 1D and 2D NMR experiments. This is the first report of these compounds being isolated from a Pestalotiopsis species. The cytotoxic activities of the compounds were evaluated, and compounds 1 and 3 demonstrated cytotoxic activities against the HL-60 tumour cell line (IC 50  ＜ 20 μM).

Synthesis, characterization, and preclinical evaluation of new thiazolidin-4-ones substituted with p-chlorophenoxy acetic acid and clofibric acid against insulin resistance and metabolic disorder.

PubMed

Gowdra, Vasantharaju S; Mudgal, Jayesh; Bansal, Punit; Nayak, Pawan G; Manohara Reddy, Seethappa A; Shenoy, Gautham G; Valiathan, Manna; Chamallamudi, Mallikarjuna R; Nampurath, Gopalan K

2014-01-01

We synthesized twenty thiazolidin-4-one derivatives, which were then characterized by standard chromatographic and spectroscopic methods. From the in vitro glucose uptake assay, two compounds behaved as insulin sensitizers, where they enhanced glucose uptake in isolated rat diaphragm. In high-carbohydrate diet-induced insulin resistant mice, these two thiazolidin-4-ones attenuated hyperglycemia, hyperinsulinemia, hypertriglyceridemia, hypercholesterolemia, and glucose intolerance. They raised the plasma leptin but did not reverse the diabetes-induced hypoadiponectinemia. Additionally, compound 3a reduced adiposity. The test compounds were also able to reverse the disturbed liver antioxidant milieu. To conclude, these two novel thiazolidin-4-ones modulated multiple mechanisms involved in metabolic disorders, reversing insulin resistance and thus preventing the development of type-2 diabetes.

Imbricatolic acid from Juniperus communis L. prevents cell cycle progression in CaLu-6 cells.

PubMed

De Marino, Simona; Cattaneo, Fabio; Festa, Carmen; Zollo, Franco; Iaccio, Annalisa; Ammendola, Rosario; Incollingo, Filomena; Iorizzi, Maria

2011-11-01

Imbricatolic acid was isolated from the methanolic extract of the fresh ripe berries of Juniperus communis (Cupressaceae) together with sixteen known compounds and a new dihydrobenzofuran lignan glycoside named juniperoside A. Their structures were determined by spectroscopic methods and by comparison with the spectral data reported in literature. Imbricatolic acid was evaluated for its ability to prevent cell cycle progression in p53-null CaLu-6 cells. This compound induces the upregulation of cyclin-dependent kinase inhibitors and their accumulation in the G1 phase of the cell cycle, as well as the degradation of cyclins A, D1, and E1. Furthermore, no significant imbricatolic acid-induced apoptosis was observed. Therefore, this plant-derived compound may play a role in the control of cell cycle. © Georg Thieme Verlag KG Stuttgart · New York.

A new ferulic acid ester from Rhodiola wallichiana var. cholaensis (Crassulaceae).

PubMed

Song, Yaling; Zhou, Jianming; Wang, Xuejing; Xie, Xue; Zhao, Yiwu; Ni, Fuyong; Huang, Wenzhe; Wang, Zhenzhong; Xiao, Wei

2018-01-01

A new ferulic acid ester, 6-feruloyloxyhexanoic acid (1), was isolated along with 10 known ones (2-11), from the concentrated water extract of Rhodiola wallichiana var. cholaensis. Their chemical structures were elucidated on the basis of extensive spectroscopic methods including Two-dimensional nuclear magnetic resonance (2D NMR) experiments. Compound 3 was isolated from this plant for the first time. The protective effects against H 2 O 2 -induced myocardial cell injury in cultured H9c2 cells were also evaluated. Compounds 1, 5 and 7-11 provided significant protective effects on H 2 O 2 -induced H9c2 cells injury at the concentration of 25 μg/mL. And the protective effects of compound 1 was also investigated by the oxygen-glucose deprivation/reperfusion (OGD/R) tests.

New chrodrimanin congeners, chrodrimanins D-H, from YO-2 of Talaromyces sp.

PubMed

Hayashi, Hideo; Oka, Yuki; Kai, Kenji; Akiyama, Kohki

2012-01-01

Four new meroterpenoids, named chrodrimanins D-G (4-7), and one known compound, renamed chrodrimanin H (8), were isolated from okara (the insoluble residue of whole soybean) that had been fermented with the YO-2 strain of Talaromyces sp. Their structures were elucidated by spectroscopic methods. Chrodrimanins D (4), E (5), and F (6) showed insecticidal activity against silkworms with respective LD(50) values of 20, 10, and 50 µg/g of diet.

SPF-32629 A and B, novel human chymase inhibitors produced by Penicillium sp.

PubMed

Shimatani, Takuro; Hosotani, Nobuo; Ohnishi, Masako; Kumagai, Kazuo; Saji, Ikutaro

2006-01-01

Two new human chymase inhibitors, SPF-32629A and B, were isolated from the cultured broth of Penicillium sp. SPF-32629. These structures were determined by spectroscopic methods and identified as new pyridone compounds. SPF-32629B was the carboxylated derivative of SPF-32629A. SPF-32629A and B specifically inhibited human chymase among four serine proteases tested with the IC50 of 0.25 and 0.42 microg/ml, respectively.

Two new phenylpropanoid glycosides with interesterification from Scrophularia dentata Royle ex Benth

NASA Astrophysics Data System (ADS)

Zhang, Liuqiang; Yang, Zhuo; Jia, Qi; Dorje, Gaawe; Zhao, Zhili; Guo, Fujiang; Li, Yiming

2013-10-01

Two new phenylpropanoid glycosides (1-2), along with seven known ones (3-9), were isolated from the whole plant of Scrophularia dentata Royle ex Benth. Their structures were elucidated by spectroscopic methods. Among them, compounds 1 and 2 failed to separated, because they can easily transform into each other by acyl migrant reaction. In this paper, the interesterification mechanism was discussed firstly and the rule can be used in the similar structure elucidation in future.

New phenyl-ethanediols from the culture broth of Boletus edulis.

PubMed

Yang, Wan-Qiu; Qin, Xiang-Dong; Shao, Hong-Jun; Fang, Li-Zhen; Wang, Fei; Ding, Zhi-Hui; Dong, Ze-Jun; Liu, Ji-Kai

2007-04-01

A new phenyl-ethanediol, (1S)-(4-acetylphenyl)-1, 2-ethanediol (1), and a new natural product, (1S)-(3-ethenylphenyl)-1, 2-ethanediol (2), were isolated from the culture broth of the basidiomycete Boletus edulis together with three related known compounds, 1-(4-ethylphenyl)-1, 2-ethanediol (3), 1-(3-ethylphenyl)-1, 2-ethanediol (4) and 1-(3-formylphenyl)-ethanone (5). Their structures were elucidated by spectroscopic methods including extensive 2D-NMR techniques.

New cassane diterpenes from Caesalpinia echinata.

PubMed

Cota, Betania Barros; de Oliveira, Djalma Menezes; de Siqueira, Ezequias Pessoa; Souza-Fagundes, Elaine Maria; Pimenta, Adriano M C; Santos, Daniel M; Rabello, Ana; Zani, Carlos Leomar

2011-10-01

An investigation of the ethanolic extract from stems of Caesalpinia echinata Lam (Leguminosae-Caesalpinioideae) led to the isolation of five new cassane diterpenes along with known lambertianic acid. Their structures were determined based on spectroscopic methods. A preliminary study on leishmanicidal activity demonstrated that compounds 1, 2 and 6 were found to inhibit the growth of amastigote-like forms of Leishmania amazonensis without affecting mononuclear cells obtained from human peripheral blood. Copyright © 2011 Elsevier B.V. All rights reserved.

Spectroscopic determination of ecologically relevant plant secondary metabolites

DOE PAGES

Couture, John J.; Singh, Aditya; Rubert-Nason, Kennedy F.; ...

2016-07-23

Spectroscopy has recently emerged as an effective method to accurately characterize leaf biochemistry in living tissue through the application of chemometric approaches to foliar optical data, but this approach has not been widely used for plant secondary metabolites. Here in this paper, we examine the ability of reflectance spectroscopy to quantify specific phenolic compounds in trembling aspen (Populus tremuloides) and paper birch (Betula papyrifera) that play influential roles in ecosystem functioning related to trophic-level interactions and nutrient cycling.

Molecular docking, spectroscopic studies and quantum calculations on nootropic drug.

PubMed

Uma Maheswari, J; Muthu, S; Sundius, Tom

2014-04-05

A systematic vibrational spectroscopic assignment and analysis of piracetam [(2-oxo-1-pyrrolidineacetamide)] have been carried out using FT-IR and FT-Raman spectral data. The vibrational analysis was aided by an electronic structure calculation based on the hybrid density functional method B3LYP using a 6-311G++(d,p) basis set. Molecular equilibrium geometries, electronic energies, IR and Raman intensities, and harmonic vibrational frequencies have been computed. The assignments are based on the experimental IR and Raman spectra, and a complete assignment of the observed spectra has been proposed. The UV-visible spectrum of the compound was recorded and the electronic properties, such as HOMO and LUMO energies and the maximum absorption wavelengths λmax were determined by the time-dependent DFT (TD-DFT) method. The geometrical parameters, vibrational frequencies and absorption wavelengths were compared with the experimental data. The complete vibrational assignments are performed on the basis of the potential energy distributions (PED) of the vibrational modes in terms of natural internal coordinates. The simulated FT-IR, FT-Raman, and UV spectra of the title compound have been constructed. Molecular docking studies have been carried out in the active site of piracetam by using Argus Lab. In addition, the potential energy surface, HOMO and LUMO energies, first-order hyperpolarizability and the molecular electrostatic potential have been computed. Copyright © 2014 Elsevier B.V. All rights reserved.

Molecular structure and spectroscopic characterization of Carbamazepine with experimental techniques and DFT quantum chemical calculations

NASA Astrophysics Data System (ADS)

Suhasini, M.; Sailatha, E.; Gunasekaran, S.; Ramkumaar, G. R.

2015-04-01

A systematic vibrational spectroscopic assignment and analysis of Carbamazepine has been carried out by using FT-IR, FT-Raman and UV spectral data. The vibrational analysis were aided by electronic structure calculations - ab initio (RHF) and hybrid density functional methods (B3LYP) performed with standard basis set 6-31G(d,p). Molecular equilibrium geometries, electronic energies, natural bond order analysis, harmonic vibrational frequencies and IR intensities have been computed. A detailed interpretation of the vibrational spectra of the molecule has been made on the basis of the calculated Potential Energy Distribution (PED) by VEDA program. UV-visible spectrum of the compound was also recorded and the electronic properties, such as HOMO and LUMO energies and λmax were determined by HF/6-311++G(d,p) Time-Dependent method. The thermodynamic functions of the title molecule were also performed using the RHF and DFT methods. The restricted Hartree-Fock and density functional theory-based nuclear magnetic resonance (NMR) calculation procedure was also performed, and it was used for assigning the 13C and 1H NMR chemical shifts of Carbamazepine.

Simple 1H NMR spectroscopic method for assay of salts of the contrast agent diatrizoate in commercial solutions.

PubMed

Hanna, G M; Lau-Cam, C A

1996-01-01

A simple, accurate, and specific 1H NMR spectroscopic method was developed for the assay of diatrizoate meglumine or the combination diatrizoate meglumine and diatrizoate sodium in commercial solutions for injection. A mixture of injectable solution and sodium acetate, the internal standard, was diluted with D2O and the 1H NMR spectrum of the solution was obtained. Two approaches were used to calculate the drug content, based on the integral values for the -N-CO-CH3 protons of diatrizoic acid at 2.23 ppm, and -N-CH3 protons of meglumine at 2.73 ppm, and the CH3-CO-protons of sodium acetate at 1.9 ppm. Recoveries (mean +/- standard deviation) of diatrizoic acid and meglumine from 10 synthetic mixtures of various amounts of these compounds with a fixed amount of internal standard were 100.3 +/- 0.55% and 100.1 +/- 0.98%, respectively. In addition to providing a direct means of simultaneously assaying diatrizoic acid and meglumine, the proposed NMR method can also be used to identify diatrizoate meglumine and each of its molecular components.

Spectroscopic investigation on structure and pH dependent Cocrystal formation between gamma-aminobutyric acid and benzoic acid.

PubMed

Du, Yong; Xue, Jiadan; Cai, Qiang; Zhang, Qi

2018-02-15

Vibrational spectroscopic methods, including terahertz absorption and Raman scattering spectroscopy, were utilized for the characterization and analysis of gamma-aminobutyric acid (GABA), benzoic acid (BA), and the corresponding GABA-BA cocrystal formation under various pH values of aqueous solution. Vibrational spectroscopic results demonstrated that the solvent GABA-BA cocrystal, similar as grinding counterpart, possessed unique characteristic features compared with that of starting parent compounds. The change of vibrational modes for GABA-BA cocrystal comparing with starting components indicates there is strong inter-molecular interaction between GABA and BA molecules during its cocrystallization process. Formation of GABA-BA cocrystal under slow solvent evaporation is impacted by the pH value of aqueous solution. Vibrational spectra indicate that the GABA-BA cocrystal could be stably formed with the solvent condition of 2.00≤pH≤7.00. In contrast, such cocrystallization did not occur and the cocrystal would dissociate into its parent components when the pH value of solvent is lower than 2.00. This study provides experimental benchmark to discriminate and identify the structure of cocrystal and also pH-dependent cocrystallization effect with vibrational spectroscopic techniques in solid-state pharmaceutical fields. Copyright © 2017 Elsevier B.V. All rights reserved.

Spectral imaging of chemical compounds using multivariate optically enhanced filters integrated with InGaAs VGA cameras

NASA Astrophysics Data System (ADS)

Priore, Ryan J.; Jacksen, Niels

2016-05-01

Infrared hyperspectral imagers (HSI) have been fielded for the detection of hazardous chemical and biological compounds, tag detection (friend versus foe detection) and other defense critical sensing missions over the last two decades. Low Size/Weight/Power/Cost (SWaPc) methods of identification of chemical compounds spectroscopy has been a long term goal for hand held applications. We describe a new HSI concept for low cost / high performance InGaAs SWIR camera chemical identification for military, security, industrial and commercial end user applications. Multivariate Optical Elements (MOEs) are thin-film devices that encode a broadband, spectroscopic pattern allowing a simple broadband detector to generate a highly sensitive and specific detection for a target analyte. MOEs can be matched 1:1 to a discrete analyte or class prediction. Additionally, MOE filter sets are capable of sensing an orthogonal projection of the original sparse spectroscopic space enabling a small set of MOEs to discriminate a multitude of target analytes. This paper identifies algorithms and broadband optical filter designs that have been demonstrated to identify chemical compounds using high performance InGaAs VGA detectors. It shows how some of the initial models have been reduced to simple spectral designs and tested to produce positive identification of such chemicals. We also are developing pixilated MOE compressed detection sensors for the detection of a multitude of chemical targets in challenging backgrounds/environments for both commercial and defense/security applications. This MOE based, real-time HSI sensor will exhibit superior sensitivity and specificity as compared to currently fielded HSI systems.

Anti-inflammatory activities of compounds from twigs of Morus alba.

PubMed

Tran, Huynh Nguyen Khanh; Nguyen, Van Thu; Kim, Jeong Ah; Rho, Seong Soo; Woo, Mi Hee; Choi, Jae Sui; Lee, Jeong-Hyung; Min, Byung Sun

2017-07-01

Five new compounds, 10-oxomornigrol F (1), (7″R)-(-)-6-(7″-hydroxy-3″,8″-dimethyl-2″,8″-octadien-1″-yl)apigenin (2), ramumorin A (3), ramumorin B (4), and (4S,7S,8R)-trihydroxyoctadeca-5Z-enoic acid (5), together with 31 known compounds (6-36), were isolated from the twigs of Morus alba (Moraceae). The chemical structures of these compounds were established using spectroscopic analyses, 1D and 2D NMR, high-resolution electrospray ionization mass spectrometry (HRESIMS), and Mosher's methods. The anti-inflammatory activities of the compounds were evaluated by investigating their ability to inhibit lipopolysaccharide (LPS)-induced nitric oxide (NO) production in macrophage RAW 264.7 cells. Compounds 1, 2, 13, 17, 19, 25-28, and 32 showed inhibitory effects with IC 50 values ranging from 2.2 to 5.3μg/mL. Compounds 1, 2, 17, 25, and 32 reduced LPS-induced inducible nitric oxide synthase (iNOS) expression in a concentration-dependent manner. In addition, pretreating the cells with compound 1, 17, and 32 significantly suppressed LPS-induced expression of cyclooxygenase-2 (COX-2) protein. Copyright © 2017. Published by Elsevier B.V.

Bioactive metabolites from an endophytic Cryptosporiopsis sp. inhabiting Clidemia hirta.

PubMed

Zilla, Mahesh K; Qadri, Masroor; Pathania, Anup S; Strobel, Gary A; Nalli, Yedukondalu; Kumar, Sunil; Guru, Santosh K; Bhushan, Shashi; Singh, Sanjay K; Vishwakarma, Ram A; Riyaz-Ul-Hassan, Syed; Ali, Asif

2013-11-01

An endophytic Cryptosporiopsis sp. was isolated from Clidemia hirta and analyzed for its secondary metabolites that lead to the isolation of three bioactive molecules. The compounds were purified from the culture broth of the fungus and their structures were determined by spectroscopic methods as (R)-5-hydroxy-2-methylchroman-4-one (1), 1-(2,6-dihydroxyphenyl)pentan-1-one (2) and (Z)-1-(2-(2-butyryl-3-hydroxyphenoxy)-6-hydroxyphenyl)-3-hydroxybut-2-en-1-one (3). Compound 1 exhibited significant cytotoxic activity against the human leukemia cell line, HL-60 with an IC50 of 4 μg/ml. This compound induced G2 arrest of the HL-60 cell cycle significantly. In addition, out of these compounds, 2 and 3 were active against several bacterial pathogens. Compound 2 was active against Bacillus cereus, Escherichia coli and Staphylococcus aureus with IC50 values varying from 18 to 30 μg/ml, and compound 3 displayed activity against Pseudomonas fluorescens with an IC50 value of 6 μg/ml. Compounds 2 and 3 are novel whereas compound 1 was reported earlier but the stereochemistry of its C-2 methyl is established for the first time. Copyright © 2013 Elsevier Ltd. All rights reserved.

Potential drug - nanosensor conjugates: Raman, infrared absorption, surface - enhanced Raman, and density functional theory investigations of indolic molecules

NASA Astrophysics Data System (ADS)

Pięta, Ewa; Paluszkiewicz, Czesława; Oćwieja, Magdalena; Kwiatek, Wojciech M.

2017-05-01

An extremely important aspect of planning cancer treatment is not only the drug efficiency but also a number of challenges associated with the side effects and control of this process. That is why it is worth paying attention to the promising potential of the gold nanoparticles combined with a compound treated as a potential drug. This work presents Raman (RS), infrared absorption (IR) and surface-enhanced Raman scattering (SERS) spectroscopic investigations of N-acetyl-5-methoxytryptamine (melatonin) and α-methyl-DL-tryptophan, regarding as anti breast cancer agents. The experimental spectroscopic analysis was supported by the quantum-chemical calculations based on the B3LYP hybrid density functional theory (DFT) at the B3LYP 6-311G(d,p) level of theory. The studied compounds were adsorbed onto two colloidal gold nanosensors synthesized by a chemical reduction method using sodium borohydride (SB) and trisodium citrate (TC), respectively. Its morphology characteristics were obtained using transmission electron microscopy (TEM). It has been suggested that the NH moiety from the aromatic ring, a well-known proton donor, causes the formation of hydrogen bonds with the negatively charged gold surface.

Dicoumarol complexes of Cu(II) based on 1,10-phenanthroline: Synthesis, X-ray diffraction studies, thermal behavior and biological evaluation

NASA Astrophysics Data System (ADS)

Dholariya, Hitesh R.; Patel, Ketan S.; Patel, Jiten C.; Patel, Kanuprasad D.

2013-05-01

A series of Cu(II) complexes containing dicoumarol derivatives and 1, 10-phenanthroline have been synthesized. Structural and spectroscopic properties of ligands were studied on the basis of mass spectra, NMR (1H and 13C) spectra, FT-IR spectrophotometry and elemental analysis, while physico-chemical, spectroscopic and thermal properties of mixed ligand complexes have been studied on the basis of infrared spectra, mass spectra, electronic spectra, powder X-ray diffraction, elemental analysis and thermogravimetric analysis. X-ray diffraction study suggested the suitable octahedral geometry for hexa-coordinated state. The kinetic parameters such as order of reaction (n), energy of activation (Ea), entropy (S*), pre-exponential factor (A), enthalpy (H*) and Gibbs free energy (G*) have been calculated using Freeman-Carroll method. Ferric-reducing antioxidant power (FRAP) of all complexes were measured. All the compounds were screened for their antibacterial activity against Escherichia coli, Pseudomonas aeruginosa, Streptococcus pyogenes and Bacillus subtilis, while antifungal activity against Candida albicans and Aspergillus niger have been carried out. Also compounds against Mycobacterium tuberculosis shows clear enhancement in the anti-tubercular activity upon copper complexation.

Quantification of major flavonoids in carnation tissues (Dianthus caryophyllus) as a tool for cultivar discrimination.

PubMed

Galeotti, Francesco; Barile, Elisa; Lanzotti, Virginia; Dolci, Marcello; Curir, Paolo

2008-01-01

One flavone-C-glycoside and two flavonol-O-glycosides were recognized and isolated as the main flavonoidal components in nine different carnation cultivars, and their chemical structures have been determined by spectroscopic methods, including UV detection, MS and NMR. The distribution of these three compounds in flowers, leaves, stems, young sprouts, and roots of each cultivar was evaluated by a simple HPLC-UV method: the graphic representation of their content in the different tissues allows to identify and characterize unambiguously each considered carnation cultivar. The presented method could be an easy, inexpensive and reliable tool for carnation cultivar discrimination.

Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field.

PubMed

Son, Sangkeun; Ko, Sung-Kyun; Kim, Jong Won; Lee, Jae Kyoung; Jang, Mina; Ryoo, In-Ja; Hwang, Gwi Ja; Kwon, Min Cheol; Shin, Kee-Sun; Futamura, Yushi; Hong, Young-Soo; Oh, Hyuncheol; Kim, Bo Yeon; Ueki, Masashi; Takahashi, Shunji; Osada, Hiroyuki; Jang, Jae-Hyuk; Ahn, Jong Seog

2016-02-01

Twelve metabolites, including five highly oxygenated azaphilones, geumsanols A-E, along with seven known analogues were isolated from Penicillium sp. KCB11A109, a fungus derived from a ginseng field. Their structures were assigned by spectroscopic means (NMR and MS), and stereochemistries were determined by extensive spectroscopic analyses ((1)H-(1)H coupling constants, NOESY, and HETLOC) and chemical derivatizations (modified Mosher's method and acetonide formation). The isolates were evaluated for their anticancer, antimicrobial, antimalarial activities, and phenotypic effects in zebrafish development. Of these compounds possessing no pyranoquinone core, only geumsanol E exhibited cytotoxic activities and toxic effects on zebrafish embryos, suggesting that a double bond at C-11 and C-12 is important for biological activity. Copyright © 2015 Elsevier Ltd. All rights reserved.

Conformational analysis, spectroscopic, structure-activity relations and quantum chemical simulation studies of 4-(trifluoromethyl)benzylamine

NASA Astrophysics Data System (ADS)

Arjunan, V.; Devi, L.; Mohan, S.

2018-05-01

The FT-IR and FT-Raman spectra of 4-trifluoromethylbenzylamine (TFMBA) have been recorded in the range 4000-450 and 4000-100 cm-1 respectively. The conformational analysis of the compound has been carried out to attain stable geometry of the compound. The complete vibrational assignment and analysis of the fundamental modes of the compound are carried out using the experimental FTIR and FT-Raman data and quantum chemical studies. The experimental vibrational frequencies are compared with the wavenumbers obtained theoretically from the B3LYP gradient calculations employing the standard high level 6-311++G** and cc-pVTZ basis sets for the optimised geometry of the compound. The structural parameters, thermodynamic properties and vibrational frequencies of the normal modes obtained from the B3LYP methods are in good agreement with the experimental data. The 1H (400 MHz; CDCl3) and 13C (100 MHz; CDCl3) nuclear magnetic resonance (NMR) spectra were also recorded. The electronic properties, highest occupied molecular orbital and lowest unoccupied molecular orbital energies are measured by DFT approach. The charges of the atoms by natural bond orbital (NBO) analysis are determined by B3LYP/cc-pVTZ method. The structure-chemical reactivity relations of the compound are determined through chemical potential, global hardness, global softness, electronegativity, electrophilicity and local reactivity descriptors by conceptual DFT methods.

New fluorescence spectroscopic method for the simultaneous determination of alkaloids in aqueous extract of green coffee beans.

PubMed

Yisak, Hagos; Redi-Abshiro, Mesfin; Chandravanshi, Bhagwan Singh

2018-05-11

There is no fluorescence spectroscopic method for the determination of trigonelline and theobromine in green coffee beans. Therefore, the objective of this study was to develop a new fluorescence spectroscopic method to determine the alkaloids simultaneously in the aqueous extract of green coffee beans. The calibration curves were linear in the range 2-6, 1-6, 1-5 mg/L for caffeine, theobromine and trigonelline, respectively, with R 2  ≥ 0.9987. The limit of detection and limit of quantification were 2, 6 and 7 µg/L and 40, 20 and 20 µg/L for caffeine, theobromine and trigonelline, respectively. Caffeine and trigonelline exhibited well separated fluorescence excitation spectra and therefore the two alkaloids were selectively quantified in the aqueous extract of green coffee. While theobromine showed overlapping fluorescence excitation spectra with caffeine and hence theobromine could not be determined in the aqueous extract of green coffee beans. The amount of caffeine and trigonelline in the three samples of green coffee beans were found to be 0.95-1.10 and 1.00-1.10% (w/w), respectively. The relative standard deviations (RSD ≤ 4%) of the method for the three compounds of interest were of very good. The accuracy of the developed analytical method was evaluated by spiking standard caffeine and trigonelline to green coffee beans and the average recoveries were 99 ± 2% for both the alkaloids. A fast, sensitive and reliable fluorescence method for the simultaneous determination of caffeine and trigonelline in the aqueous extract of green coffee beans was developed and validated. The developed method reflected an effective performance to the direct determination of the two alkaloids in the aqueous extract of green coffee beans.

An Unusual Conformational Isomer of Verrucosidin Backbone from a Hydrothermal Vent Fungus, Penicillium sp. Y-50-10.

PubMed

Pan, Chengqian; Shi, Yutong; Auckloo, Bibi Nazia; Chen, Xuegang; Chen, Chen-Tung Arthur; Tao, Xinyi; Wu, Bin

2016-08-18

A new verrucosidin derivative, methyl isoverrucosidinol (1), was isolated from the marine fungus Penicillium sp. Y-50-10, dwelling in sulfur rich sediment in the Kueishantao hydrothermal vents off Taiwan. The structure was established by spectroscopic means including HRMS and 2D-NMR spectroscopic analysis. The absolute configuration was defined mainly by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Among hitherto known compounds with a verrucosidine backbone isolated from natural resource, compound 1 represents the first example of a new conformational isomer of its skeleton, exhibiting antibiotic activity against Bacillus subtilis with MIC value 32 μg/mL.

Synthesis, crystal structures and spectroscopic properties of triazine-based hydrazone derivatives; a comparative experimental-theoretical study.

PubMed

Arshad, Muhammad Nadeem; Bibi, Aisha; Mahmood, Tariq; Asiri, Abdullah M; Ayub, Khurshid

2015-04-03

We report here a comparative theoretical and experimental study of four triazine-based hydrazone derivatives. The hydrazones are synthesized by a three step process from commercially available benzil and thiosemicarbazide. The structures of all compounds were determined by using the UV-Vis., FT-IR, NMR (1H and 13C) spectroscopic techniques and finally confirmed unequivocally by single crystal X-ray diffraction analysis. Experimental geometric parameters and spectroscopic properties of the triazine based hydrazones are compared with those obtained from density functional theory (DFT) studies. The model developed here comprises of geometry optimization at B3LYP/6-31G (d, p) level of DFT. Optimized geometric parameters of all four compounds showed excellent correlations with the results obtained from X-ray diffraction studies. The vibrational spectra show nice correlations with the experimental IR spectra. Moreover, the simulated absorption spectra also agree well with experimental results (within 10-20 nm). The molecular electrostatic potential (MEP) mapped over the entire stabilized geometries of the compounds indicated their chemical reactivates. Furthermore, frontier molecular orbital (electronic properties) and first hyperpolarizability (nonlinear optical response) were also computed at the B3LYP/6-31G (d, p) level of theory.

Photoelectron Diffraction and Holography Studies of 2D Materials and Interfaces

NASA Astrophysics Data System (ADS)

Kuznetsov, Mikhail V.; Ogorodnikov, Ilya I.; Usachov, Dmitry Yu.; Laubschat, Clemens; Vyalikh, Denis V.; Matsui, Fumihiko; Yashina, Lada V.

2018-06-01

Photoelectron diffraction (XPD) and holography (XPH) are powerful spectroscopic methods that allow comprehensive exploration and characterization of certain structural properties of materials, in particular those of 2D systems and interfaces. Recent developments in XPD and XPH are especially impressive when they are applied to partially disordered systems such as intercalation compounds, doped graphene, buffer layers or adsorbates and imperfectly ordered germanene and phoshporene. In our brief review, we sum up the advances in XPD and XPH studies of 2D materials and discuss the unique opportunities granted by these two interrelated methods.

Investigation of antimicrobial activities, DNA interaction, structural and spectroscopic properties of 2-chloro-6-(trifluoromethyl)pyridine

NASA Astrophysics Data System (ADS)

Evecen, Meryem; Kara, Mehmet; Idil, Onder; Tanak, Hasan

2017-06-01

2-Chloro-6-(trifluoromethyl)pyridine has been characterized by FT-IR, 1H and 13C NMR experiment. FT-IR spectra of the molecule has been recorded in the 4000-400 cm-1 region. The molecular structural parameters and vibrational frequencies were computed using the HF and DFT (B3LYP, B3PW91) methods with the 6-31+G(d,p) and 6-311++G(d,p) basis sets. 1H and 13C NMR Gauge Including Atomic Orbital (GIAO) chemical shifts of the compound were calculated using the density functional method (B3LYP) with the 6-311++G(d,p) basis set. The vibrational wavenumbers and chemical shifts were compared with the experimental data of the compound. Using the TD-DFT methodology, electronic absorption spectra of the compound have been computed. Besides, solvent effects on the excitation energies and chemical shifts were carried out using the integral equation formalism of the polarisable continuum model (IEF-PCM). DFT calculations of the compound, Mulliken's charges, molecular electrostatic potential (MEP), natural bond orbital (NBO) and thermodynamic properties were also obtained theoretically. In addition, the antimicrobial activities were tested by using minimal inhibitory concentration method (MIC) and also the effect of the molecule on pBR322 plasmid DNA was monitored byagarose gel electrophoresis experiments.

1,3-Oxazin-6-one Derivatives and Bohemamine-Type Pyrrolizidine Alkaloids from a Marine-Derived Streptomyces spinoverrucosus

PubMed Central

2015-01-01

Two new 1,3-oxazin-6-one derivatives (1 and 2) and six new bohemamine-type pyrrolizidine alkaloids (3–8) were isolated from the marine-derived Streptomyces spinoverrucosus strain SNB-048. Their structures including the absolute configurations were fully elucidated on the basis of spectroscopic analysis, ECD spectra, quantum chemical calculations, and chemical methods. Compounds 1 and 2 possess a γ-lactam moiety and a 1,3-oxazin-6-one system. PMID:26489038

Syntheses of organic compounds in the presence of the fused iron catalyst and their mechanisms and kinetics

NASA Astrophysics Data System (ADS)

Glebov, L. S.; Kliger, G. A.

1989-10-01

New synthetic possibilities of the reduced promoted fused iron catalyst in intermolecular and intramolecular amination, cyanation, hydrogenation-dehydrogenation, and hydrodeoxygenation reactions and intermolecular and intramolecular dehydration, polymerisation, and isotope exchange are examined. The mechanisms and kinetics of the reactions leading to the synthesis of amines, alcohols, hydrocarbons, and other organic compunds are discussed. A laser Raman spectroscopic method is described for the investigation of heterogeneous organic catalysis in situ. The bibliography includes 148 references.

(+/-)-Gelliusines A and B, two diastereomeric brominated tris-indole alkaloids from a deep water new caledonian marine sponge (Gellius or Orina sp.).

PubMed

Bifulco, G; Bruno, I; Minale, L; Riccio, R; Calignano, A; Debitus, C

1994-09-01

Two new diastereomeric brominated tris-indole alkaloids occurring as enantiomeric pairs, (+/-)-gelliusines A [1] and B [2], have been isolated from a deep water New Caledonian sponge (Gellius or Orina sp.), whose crude extract exhibited cytotoxicity against KB cells. Their structures were elucidated by spectroscopic methods including one- and two-dimensional nmr spectroscopy. The major compound, (+/-) gelliusine A [1], which showed very weak cytotoxicity, proved to be active at the serotonin receptor.

Free radical-scavenging delta-lactones from Boletus calopus.

PubMed

Kim, Jin-Woo; Yoo, Ick-Dong; Kim, Won-Gon

2006-12-01

The methanol extracts from the fruiting body of the mushroom Boletus calopus showed free radical-scavenging activity. Bioactivity-guided fractionation of the methanol extracts led to a new hydroxylated calopin named calopin B, along with the known delta-lactones calopin and cyclocalopin A. The structure of the new calopin analogue was elucidated by spectroscopic methods. All compounds showed potent free radical-scavenging activity against superoxide, DPPH, and ABTS radicals with IC (50) values of 1.2 - 5.4 microg/mL.

Cladielloides A and B: New Eunicellin-Type Diterpenoids from an Indonesian Octocoral Cladiella sp

PubMed Central

Chen, Yung-Husan; Tai, Chia-Ying; Hwang, Tsong-Long; Weng, Ching-Feng; Li, Jan-Jung; Fang, Lee-Shing; Wang, Wei-Hsien; Wu, Yang-Chang; Sung, Ping-Jyun

2010-01-01

Two new eunicellin-type diterpenoids, cladielloides A (1) and B (2), which were found to possess a 2-hydroxybutyroxy group in their structures, were isolated from an Indonesian octocoral identified as Cladiella sp. The structures of eunicellins 1 and 2 were elucidated by spectroscopic methods. Cladielloide B (2) exhibited moderate cytotoxicity toward CCRF-CEM tumor cells and this compound displayed significant inhibitory effects on superoxide anion generation and elastase release by human neutrophils. PMID:21339957

Dimeric and trimeric hydrolyzable tannins from Quercus coccifera and Quercus suber.

PubMed

Ito, Hideyuki; Yamaguchi, Koji; Kim, Tae-Hoon; Khennouf, Seddik; Gharzouli, Kamel; Yoshida, Takashi

2002-03-01

Three new hydrolyzable tannins, cocciferins D(1) (1), D(2) (2), and T(1) (4), were isolated from the leaves of Quercus coccifera. Cocciferin D(2) (2) and two additional new tannins, cocciferins D(3) (3) and T(2) (5), were also obtained from the leaves of Quercus suber. Their oligomeric structures were elucidated on the basis of spectroscopic methods and chemical evidence. Compounds 2, 3, and 5 were rare oligomers possessing glucose cores with both open-chain and pyranose forms.

Potent HGF/c-Met axis inhibitors from Eucalyptus globulus: the coupling of phloroglucinol and sesquiterpenoid is essential for the activity.

PubMed

Yang, Sheng-Ping; Zhang, Xiao-Wei; Ai, Jing; Gan, Li-She; Xu, Jin-Biao; Wang, Ying; Su, Zu-Shang; Wang, Lu; Ding, Jian; Geng, Mei-Yu; Yue, Jian-Min

2012-09-27

Eucalyptin A (1), together with two known compounds 2 and 3 exhibiting potent inhibition on HGF/c-Met axis, was discovered from the fruits of Eucalyptus globulus. 1 possessed an unprecedented carbon framework of phloroglucinol-coupled sesquiterpenoid, and its structure was elucidated by spectroscopic method and ECD calculation. A brief structure-activity relationship discussion indicated that the coupling of a phloroglucinol and a sesquiterpenoid is essential for the activity.

Diterpenoids from Salvia ceratophylla.

PubMed

Gören, Ahmet C; Topçu, Gülaçti; Oksüz, Sevil; Kökdil, Gamze; Voelter, Wolfgang; Ulubelen, Ayhan

2002-02-01

Salvia ceratophylla L. has yielded four known and two new diterpenoids together with two triterpenic acids, a steroid and a flavone. The structures of the compounds were established by spectroscopic analyses. One of the known compounds candidissiol exhibited a high antibacterial activity against Staphylococcus epidermidis and Proteus mirabilis.

The Elusive Excited Quintet [superscript 5]D of Tb(III): A Source of Luminescence and Resonance Energy Transfer in Terbium Compounds

ERIC Educational Resources Information Center

Klier, Kamil

2010-01-01

The understanding of electronic structure of atomic and molecular term states involved in spectroscopic transitions is aided by projecting combinations of micro-configurations to multi-electron states with "good" quantum numbers of angular momenta. In rare-earth (RE) compounds, atomic term labels are justifiably carried over to compounds, because…

Three new natural compounds from the root bark essential oil from Xylopia aethiopica.

PubMed

Yapi, Thierry Acafou; Boti, Jean Brice; Attioua, Barthelemy Koffi; Ahibo, Antoine Coffy; Bighelli, Ange; Casanova, Joseph; Tomi, Félix

2012-01-01

In the course of on-going work on the characterisation of aromatic plants from the Ivory Coast we investigated the composition of the root oil from Xylopia aethiopica. The aim of this work was to investigate the chemical composition of X. aethiopica root oil and elucidate the structure of two new compounds. Analysis of the essential oil was carried out using a combination of chromatographic (CC, GC with retention indices) and spectroscopic techniques (MS, (13)C-NMR, 2D-NMR). Twenty seven components, accounting for 95.6% of the whole composition, were identified including various compounds for which spectroscopic data were absent on commercial computerised MS libraries. Three compounds are reported for the first time as natural compounds and the structure of two new compounds, 4,4-dimethyl-2-vinylcyclohexene and endo-5-methoxy-3-patchoulene, has been elucidated using extensive two-dimensional NMR spectroscopy. The composition of X. aethiopica root oil is dominated by two dimethylvinylcyclohexene isomers. It differs drastically from the composition of leaf and fruit oils of the same plant. The combination of analytical techniques appeared crucial for a fruitful analysis. Copyright © 2012 John Wiley & Sons, Ltd.

Synthesis, characterization and biological evaluation of novel α, β unsaturated amides.

PubMed

Esmailzadeh, K; Housaindokht, M R; Moradi, A; Esmaeili, A A; Sharifi, Z

2016-05-15

Three derivatives of α,β unsaturated amides have been successfully synthesized via Ugi-four component (U-4CR) reaction. The interactions of the amides with calf thymus deoxyribonucleic acid (ct-DNA) have been investigated in the Tris-HCl buffer (pH=7.4) using viscometric, spectroscopic, thermal denaturation studies, and also molecular docking. By UV-Vis absorption spectroscopy studies, adding CT-DNA to the compound solution caused the hypochromism indicates that there are interactions between the compounds and DNA base pairs. In competitive fluorescence with methylene blue as an intercalator probe, adding compounds to DNA-MB solution caused an increase in emission spectra of the complex. This could be because of compound replacing, with similar binding mode of MB, between the DNA base pairs due to release of bonded MB molecules from DNA-MB complex. Thermal denaturation studies and viscometric experiments also indicated that all three investigated compounds bind to CT-DNA by non-classical intercalation mode. Additionally, molecular docking technique predicted partial intercalation binding mode for the compounds. Also, the highest binding energy was obtained for compound 5a. These results are in agreement with results obtained by empirical methods. Copyright © 2016 Elsevier B.V. All rights reserved.

Six cytotoxic annonaceous acetogenins from Annona squamosa seeds.

PubMed

Chen, Yong; Chen, Jian-Wei; Wang, Yu; Xu, Sha-Sha; Li, Xiang

2012-12-01

Custard apple (Annona squamosa L.) is an edible tropical fruit, and its seeds had been used in south China as a folk medicine to treat "malignant sore" (cancer) and as an insecticide. Phytochemical investigation of the ethanol fraction of custard apple seeds led to the isolation of six new annonaceous acetogenins: annosquacins A-D (1-4), annosquatin A (5) and annosquatin B (6). Their structures were elucidated by spectroscopic analysis. Compounds 1-4 are adjacent bistetrahydrofuran annonaceous acetogenins. Compounds 5 and 6 are non-adjacent bistetrahydrofuran annonaceous acetogenins and the first examples in which the tetrahydrofuran ring system is located between C-9 and C-20. The absolute configurations of 1-6 were defined by the application of the Mosher method. Compounds 1-6 exhibited potent cytotoxic activity in vitro against five human tumour cell lines. Compounds 5 and 6 showed a high selectivity toward the MCF-7 and A-549 cell line respectively. Copyright © 2012 Elsevier Ltd. All rights reserved.

Postmodification of MOF-5 using secondary complex formation using 8- hydroxyquinoline (HOQ) for the development of visible light active photocatalysts

NASA Astrophysics Data System (ADS)

Thakare, Sanjay R.; Ramteke, Shruti M.

2018-05-01

A novel HOQ@MOF-5 compound photocatalyst was successfully constructed by interacting 8- Hydroxyquinoline with MOF-5 synthesized through a room temperature method. The secondary complex formation between the Zn cluster with 8-Hydroxyquinoline harnessed visible light and acted as a mediator to transfer photoinduced electrons to MOF-5 for enhancing the photocatalytic reaction rate with visible light. HOQ@MOF-5 was characterized by various spectroscopic techniques, such as XRD showing the crystalline nature of compound, UV-Visible spectroscopy showing the 2.54 eV band gap of HOQ@MOF-5 and morphological analysis tools, such as the nanoparticle nature of the compound with 9.561 nm particle size. The photocatalytic effect was estimated using the photocatalytic degradation of phenol as a representative organic pollutant under visible light irradiation. This work provides a new compound acting as source of electrons transfer for the development of efficient photocatalysts for remediation of environmental pollution.

Induction of quinone reductase (QR) by withanolides isolated from Physalis pubescens L. (Solanaceae).

PubMed

Ji, Long; Yuan, Yonglei; Ma, Zhongjun; Chen, Zhe; Gan, Lishe; Ma, Xiaoqiong; Huang, Dongsheng

2013-09-01

In the present study, it was demonstrated that the dichloromethane extract of Physalis pubescens L. (DEPP) had weak potential quinone reductase (QR) inducing activity, but an UPLC-ESI-MS method with glutathione (GSH) as the substrate revealed that the DEPP had electrophiles (with an α,β-unsaturated ketone moiety). These electrophiles could induce quinone reductase (QR) activity, which might be attributed to the modification of the highly reactive cysteine residues in Keap1. Herein, four withanolides, including three new compounds physapubescin B (2), physapubescin C (3), physapubescin D (4), together with one known steroidal compound physapubescin (1) were isolated. Structures of these compounds were determined by spectroscopic analysis and that of physapubescin C (3) was confirmed by a combination of molecular modeling and quantum chemical DFT-GIAO calculations. Evaluation of the QR inducing activities of all withanolides indicated potent activities of compounds 1 and 2, which had a common α,β-unsaturated ketone moiety. Copyright © 2013 Elsevier Ltd. All rights reserved.

Two new ortho benzoquinones from Uncaria rhynchophylla.

PubMed

Zhang, Qian; Chen, Lei; Hu, Le-Jian; Liu, Wen-Yuan; Feng, Feng; Qu, Wei

2016-03-01

The present study was designed to determine the chemical constituents of the stems and hooks of Uncaria rhynchophylla. The chemical constituents were isolated and purified from CH2Cl2 fraction by chromatography. Their structures were elucidated by spectroscopic analyses. Their cytotoxicity was tested using MTT method. Two new ortho benzoquinones, 3-diethylamino-5-methoxy-1, 2-benzoquinone (1) and 3-ethylamino-5-methoxy-1, 2-benzoquinone (2), together with a known compound isorhynchophyllic acid (3) were isolated from U. rhynchophylla. These compounds were evaluated for their cytotoxicity against cancer cells A549, HepG2 and A2780. Compounds 1 and 2 were new ortho benzoquinones and showed weak antiproliferative activities on A549, HepG2 and A2780 cells. Compound 3 significantly inhibited the proliferation of A549, HepG2 and A2780 cells with IC50 values being 5.8, 12.8 and 11.8 µmol·L(-1), respectively. Copyright © 2016 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.

A new phenol glycoside from Physalis angulata.

PubMed

Sun, Cheng-Peng; Nie, Xiu-Fang; Kang, Ning; Zhao, Feng; Chen, Li-Xia; Qiu, Feng

2017-05-01

A new phenol glycoside, physanguloside A (1), was isolated from Physalis angulata together with four known compounds. We report herein, for the first time, the presence of compounds 2-5 in the genus Physalis. The structures of all the compounds were established by NMR, IR, UV and HRESIMS spectroscopic analyses, and comparison with the literature data. All isolated compounds were assayed for inhibitory activity on nitric oxide production by LPS-induced in RAW 264.7 macrophages.

DFT, FT-IR, FT-Raman and vibrational studies of 3-methoxyphenyl boronic acid

NASA Astrophysics Data System (ADS)

Patil, N. R.; Hiremath, Sudhir M.; Hiremath, C. S.

2018-05-01

The aim of this work is to study the possible stable, geometrical molecular structure, experimental and theoretical FT-IR and FT-Raman spectroscopic methods of 3-Methoxyphenyl boronic acid (3MPBA). FT-IR and FT-Raman spectra were recorded in the region of 4000-400 cm-1 and 40000-50 cm-1 respectively. The optimized geometric structure and vibrational wavenumbers of the title compound were searched by B3LYP hybrid density functional theory method with 6-311++G (d, p) basis set. The Selectedexperimentalbandswereassignedandcharacterizedonthebasisofthescaledtheoreticalwavenumbersby their potential energy distribution (PED) of the vibrational modes obtained from VEDA 4 program. Finally, the predicted calculation results were applied to simulated FT-IR and FT-Raman spectra of the title compound, which show agreement with the observed spectra. Whereas, it is observed that, the theoretical frequencies are more than the experimental one for O-H stretching vibration modes of the title molecule.

Novel 2-Phenoxyanilide Congeners Derived from a Hit Structure of the TCAMS: Synthesis and Evaluation of Their in Vitro Activity against Plasmodium falciparum.

PubMed

Weidner, Thomas; Nasereddin, Abed; Preu, Lutz; Grünefeld, Johann; Dzikowski, Ron; Kunick, Conrad

2016-02-17

The Tres Cantos Antimalarial Compound Set (TCAMS) is a publicly available compound library which contains 13533 hit structures with confirmed activity against Plasmodium falciparum, the infective agent responsible for malaria tropica. The TCAMS provides a variety of starting points for the investigation of new antiplasmodial drug leads. One of the promising compounds is TCMDC-137332, which seemed to be a good starting point due to its antiplasmodial potency and its predicted physicochemical properties. Several new analogues based on a 2-phenoxyanilide scaffold were synthesized by standard amide coupling reactions and were fully characterized regarding their identity and purity by spectroscopic and chromatographic methods. Furthermore, the results of the biological evaluation of all congeners against Plasmodium falciparum NF54 strains are presented. The findings of our in vitro screening could not confirm the presumed nanomolar antiplasmodial activity of TCMDC-137332 and its derivatives.

A green approach toward quinoxalines and bis-quinoxalines and their biological evaluation against A431, human skin cancer cell lines.

PubMed

Bandyopadhyay, Debasish; Cruz, Jessica; Morales, Liza D; Arman, Hadi D; Cuate, Erica; Lee, Young S; Banik, Bimal K; Kim, Dae J

2013-08-01

The objective of this study was to develop a practical green procedure to synthesize quinoxalines and bis-quinoxalines and evaluate their inhibitory effects on the viability of A431 human epidermoid carcinoma cells. A series of quinoxaline and bis-quinoxaline derivatives have been designed and synthesized following a microwave-assisted and bismuth nitrate-catalyzed eco-friendly route. A detailed comparison has been made between microwave-induced protocol with the reactions occurred at room temperature. The structure of the compounds have been elucidated by various spectroscopic methods and finally confirmed by x-ray crystallographic analyses. Two quinoxaline derivatives, compounds 6 and 12 have demonstrated inhibitory effects on the viability of A431 human epidermoid carcinoma cells when compared with HaCaT nontumorigenic human keratinocyte cells. Notably, compound 6 inhibits Stat3 phosphorylation/activation in A431 skin cancer cells.

Meroterpenoid and diphenyl ether derivatives from Penicillium sp. MA-37, a fungus isolated from marine mangrove rhizospheric soil.

PubMed

Zhang, Yi; Li, Xiao-Ming; Shang, Zhuo; Li, Chun-Shun; Ji, Nai-Yun; Wang, Bin-Gui

2012-11-26

Penicillium sp. MA-37, which was obtained from the rhizospheric soil of the mangrove plant Bruguiera gymnorrhiza, exhibited different chemical profiles in static and shaken fermentation modes. Three new meroterpenoid derivatives, 4,25-dehydrominiolutelide B (1), 4,25-dehydro-22-deoxyminiolutelide B (2), and isominiolutelide A (3), together with three known ones were characterized from its static fermentation, while three new diphenyl ether derivatives, namely, Δ(1('),3('))-1'-dehydroxypenicillide (4), 7-O-acetylsecopenicillide C (5), and hydroxytenellic acid B (6), along with five related metabolites were isolated from the shaken culture. The structures of these compounds were elucidated on the basis of spectroscopic analysis, and the structure of compound 2 was confirmed by X-ray crystallographic analysis. The absolute configurations of 1-3 and 6 were determined by ECD and modified Mosher's method, respectively. All isolated compounds were evaluated for brine shrimp lethality and antibacterial activity.

Kinetic studies of the impact of thiocyanate moiety on the catalytic properties of Cu(II) and Fe(III) complexes of a new Mannich base

NASA Astrophysics Data System (ADS)

Ayeni, Ayowole O.; Watkins, Gareth M.

2018-04-01

Four new metal complexes of a novel Mannich base 5-methyl-2-((4-(pyridin-2-yl)piperazin-1-yl)methyl)phenol (HL) have been prepared. The compounds were characterized by an array of analytical and spectroscopic methods including Nuclear Magnetic Resonance, Infra-red and UV-Visible spectroscopy. Compounds 1-4 behaved as effective catalysts towards the oxidation of 3,5-di-tert-butylcatechol (3,5-DTBC) to its corresponding quinone in the presence of molecular oxygen in DMF solution while compound 4 proved to be the best catalyst with a turnover rate of 17.93 ± 1.10 h-1 as other complexes showed lower rates of oxidation. Also with the exception of dinuclear iron complex (4); thiocyanate containing Cu(II) complex exhibited lower catecholase activity compared to the Cu(II) complex without it.

A new acetophenone derivative from flowers of Helichrysum italicum (Roth) Don ssp. italicum.

PubMed

Rigano, Daniela; Formisano, Carmen; Pagano, Ester; Senatore, Felice; Piacente, Sonia; Masullo, Milena; Capasso, Raffaele; Izzo, Angelo A; Borrelli, Francesca

2014-12-01

A new acetophenone derivative named gnaphaliol 9-O-propanoate (1) was isolated from the chloroform fraction of EtOH extract of Helichrysum italicum ssp. italicum flowers along with the five known acetophenones 12-acetoxytremetone (2), 13-(2-methylpropanoyloxy)toxol (3), [2,3-dihydro-2-[1-(hydroxymethyl)ethenyl]-5-benzofuranyl]-ethanone (4), 1-[2-[1-[(acetyloxy)methyl]ethenyl]-2,3-dihydro-3-hydroxy-5-benzofuranyl]-ethanone (5) and gnaphaliol (6). The structures of compounds 1-6 were elucidated by extensive spectroscopic methods including 1D- ((1)H and (13)C) and 2D-NMR (DQF-COSY, HSQC, HMBC, TOCSY and ROESY) experiments as well as ESIMS analysis. The isolated compounds were investigated for their cytotoxicity, anti-inflammatory and antioxidant properties. Biological assays on human colonic epithelial cells showed that compound 2 possessed antioxidant effects reducing reactive oxygen species (ROS) production. Copyright © 2014 Elsevier B.V. All rights reserved.

Synthesis, Characterization, Electrochemical Studies, and In Vitro Antibacterial Activity of Novel Thiosemicarbazone and Its Cu(II), Ni(II), and Co(II) Complexes

PubMed Central

Khan, Salman A.; Asiri, Abdullah M.; Al-Amry, Khalid; Malik, Maqsood Ahmad

2014-01-01

Metal complexes were prepared by the reaction of thiosemicarbazone with CuCl2, NiCl2, CoCl2, Cu(OAc)2, Ni(OAc)2, and Co(OAc)2. The thiosemicarbazone coordinates to metal through the thionic sulfur and the azomethine nitrogen. The thiosemicarbazone was obtained by the thiosemicarbazide with 3-acetyl-2,5-dimethylthiophene. The identities of these compounds were elucidated by IR, 1H, 13C-NMR, and GC-MS spectroscopic methods and elemental analyses. The antibacterial activity of these compounds was first tested in vitro by the disc diffusion assay against two Gram-positive and two Gram-negative bacteria, and then the minimum inhibitory concentration (MIC) was determined by using chloramphenicol as reference drug. The results showed that compound 1.1 is better inhibitor of both types of tested bacteria as compared to chloramphenicol. PMID:24523641

Steroids from the leaves of Chinese Melia azedarach and their cytotoxic effects on human cancer cell lines.

PubMed

Wu, Shi-Biao; Ji, Yan-Ping; Zhu, Jing-Jing; Zhao, Yun; Xia, Gang; Hu, Ying-He; Hu, Jin-Feng

2009-09-01

Three new (1-3) and several known (4-6) steroids were isolated from the leaves of Chinese Melia azedarach. The structures of the new compounds were elucidated by means of spectroscopic methods including 2D NMR techniques and mass spectrometry to be (20S)-5,24(28)-ergostadiene-3beta,7alpha,16beta,20-tetrol (1), (20S)-5-ergostene-3beta,7alpha,16beta,20-tetrol (2), and 2alpha,3beta-dihydro-5-pregnen-16-one (3). The cytotoxicities of the isolated compounds against three human cancer cell lines (A549, H460, U251) were evaluated; only compounds 1, 2, and (20S)-5-stigmastene-3beta,7alpha,20-triol (4) were found to show significant cyctotoxic effects with IC(50)s from 12.0 to 30.1 microg/mL.

Inhibition of the calcineurin pathway by two tannins, chebulagic acid and chebulanin, isolated from Harrisonia abyssinica Oliv.

PubMed

Lee, Won Jeong; Moon, Jae Sun; Kim, Sung In; Kim, Young Tae; Nash, Oyekanmi; Bahn, Yong-Sun; Kim, Sung Uk

2014-10-01

In order to discover and develop novel signaling inhibitors from plants, a screening system was established targeting the two-component system of Cryptococcus neoformans by using the wild type and a calcineurin mutant of C. neoformans, based on the counter-regulatory action of high-osmolarity glycerol (Hog1) mitogen-activated protein kinase and the calcineurin pathways in C. neoformans. Among 10,000 plant extracts, that from Harrisonia abyssinica Oliv. exhibited the most potent inhibitory activity against C. neoformans var. grubii H99 with fludioxonil. Bioassay-guided fractionation was used to isolate two bioactive compounds from H. abyssinica, and these compounds were identified as chebulagic acid and chebulanin using spectroscopic methods. These compounds specifically inhibited the calcineurin pathway in C. neoformans. Moreover, they exhibited potent antifungal activities against various human pathogenic fungi with minimum inhibitory concentrations ranging from 0.25 to over 64 µg/ml.

A new antibacterial benzophenone glycoside from Psidium guajava (Linn.) leaves.

PubMed

Ukwueze, Stanley E; Osadebe, Patience O; Okoye, Festus B C

2015-01-01

Bioactivity-guided fractionation of methanol extract from the leaves of Psidium guajava L. (Myrtaceae) yielded a new benzophenone glycoside, Guajaphenone A (2) together with two known compounds, Garcimangosone D (1) and Guaijaverin (3). Their structures were elucidated by analysis of spectroscopic data including 1D and 2D NMR and electrospray ionisation mass spectrometry (ESI-MS). The isolated compounds were screened against standard strains of Gram-positive and Gram-negative bacteria using broth dilution assay method, and the MIC values determined and compared with reference antibiotic ceftriaxone. They were found to have significant antibacterial activities against Escherichia coli and Staphylococcus aureus with all of them showing better activities against S. aureus, but displaying weaker activities, in comparison to ceftriaxone. However, despite reduced effect of these compounds against the organisms, this work opens the perspective to use these molecules as 'leads' for the design of novel and selective drug candidates for some tropical infectious diseases.

Antiproliferative and anti-inflammatory furostanol saponins from the rhizomes of Tupistra chinensis.

PubMed

Xiang, Limin; Wang, Yihai; Yi, Xiaomin; He, Xiangjiu

2016-12-01

Phytochemical investigations of the rhizome of Tupistra chinensis led to the isolation of ten new furostanol saponins along with fourteen known spirostanols. Their chemical structures were elucidated on the basis of spectroscopic and chemical methods, including IR, NMR, MS, and GC analyses. The antiproliferative effects against FaDu and Detroit 562 cell lines and inhibitory activities on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in a macrophage cell line RAW 264.7 were assayed for all the isolated compounds. Compound 14 exhibited significant antiproliferative effects against FaDu and Detroit 562 cells with IC 50 values of 1.1±0.1 and 1.2±0.1μM, respectively. Compounds 1, 2, 6, 13, 16, 19 and 24 exhibited inhibitory effects on NO production with IC 50 values ranging from 15.7 to 46.2μM. Copyright © 2016 Elsevier Inc. All rights reserved.

Alkaloids from the leaves of Uncaria rhynchophylla and their inhibitory activity on NO production in lipopolysaccharide-activated microglia.

PubMed

Yuan, Dan; Ma, Bin; Wu, Chunfu; Yang, Jingyu; Zhang, Lijia; Liu, Suiku; Wu, Lijun; Kano, Yoshihiro

2008-07-01

Two new isomeric alkaloids, 18,19-dehydrocorynoxinic acid B (1) and 18,19-dehydrocorynoxinic acid (2), were isolated from the CHCl3 extract of the leaves of Uncaria rhynchophylla, together with four known rhynchophylline-type alkaloids, corynoxeine (3), isocorynoxeine (4), rhynchophylline (5), and isorhynchophylline (6), and an indole alkaloid glucoside, vincoside lactam (7). The structures of compounds 1 and 2 were elucidated by spectroscopic methods including UV, IR, HREIMS, 1D and 2D NMR, and CD experiments. The activity assay showed that compounds 3-6, with a C-16 carboxylic ester group, and 7 exhibited inhibitory activity on lipopolysaccharide (LPS)-induced NO release in primary cultured rat cortical microglia (IC 50: 13.7-19.0 microM). However, only weak inhibitory activity was observed for compounds 1 and 2, with a C-16 carboxylic acid group (IC 50: >100 microM).

[Studies on chemical constituents from herbs of Botrychium lanuginosum].

PubMed

Wang, Dong; Liu, Xiao-qiu; Yao, Chun-suo; Fang, Wei-shuo

2008-11-01

To study the chemical constituents of Botrychium lanuginosum. Various chromatographic techniques were used to isolate and purify the constituents. The structures were elucidated by chemical evidence and spectroscopic methods. Ten compounds were isolated from the 95% ethanol extract of the herb of B. lanuginosum and their structures were elucidated as 30-nor-21beta-hopan-22-one (1), beta-sitosterol (2), luteolin (3), thunberginol A (4), apigenin (5), (6'-O-palmitoyl)-sitosterol-3-O-beta-D-glucoside (6), daucosterol (7), 1-O-beta-D-glucopyranosyl-(2S, 3R, 4E, 8Z)-2-[(2R-hydroxy hexadecanoyl) amino]-4, 8-octadecadiene-1, 3-diol (8), luteolin-7-O-glucoside (9), sucrose (10). Compounds 1-10 were isolated from this genus for the first time.

5-phosphonato-3,4-dihydropyrimidin-2(1H)-ones: Zinc triflate-catalyzed one-pot multi-component synthesis, X-ray crystal structure and anti-inflammatory activity

NASA Astrophysics Data System (ADS)

Essid, Idris; Lahbib, Karima; Kaminsky, Werner; Ben Nasr, Cherif; Touil, Soufiane

2017-08-01

Herein we report a simple and efficient one-pot three-component synthesis of 5-phosphonato-3,4-dihydropyrimidin-2(1H)-ones, through the zinc triflate-catalyzed Biginelli-type reaction of β-ketophosphonates, aldehydes and urea. The compounds obtained were characterized by various spectroscopic tools including IR, NMR (1H, 31P, 13C) spectroscopy, mass spectrometry and single crystal X-ray diffraction. All the synthesized compounds were screened, for the first time, for anti-inflammatory activity by carrageenan-induced hind paw edema method, using female Wister rats and they showed significant anti-inflammatory activity in some cases higher than the standard indomethacin.

BI- and tricyclic diterpenoids from Halimium viscosum.

PubMed

Rodilla, J M; De Mendonça, D I; Ismael, M I; Figueiredo, J A; Silva, M L; Lopes, E

2001-01-01

The study of the acid and neutral parts of the n-hexane extract of Halimium viscosum (S. João da Pesqueira, Portugal) has led to the isolation of various known diterpenoids with the ent-halimane skeleton. Five new compounds have now been isolated, one with the ent-halimane skeleton, and four with the valparane skeleton, two of them with the valparane skeleton degraded. The structures of these compounds, determined by spectroscopic methods using 2D experiments (1H-13C, HMQC and HMBC), were dimethyl 1(10)-halimen-15,18-dioate, dimethyl 3,19-dinor-15-valparen-2,4-dioate, methyl 16-nor-2,3-secovalpara-3,15-dioxo-2-oate, 1,3,5,1 5-valparatetraene and 3R-4alpha-methoxy-15-valparen-2-one.

A new aurone glycoside with antifungal activity from marine-derived fungus Penicillium sp. FJ-1.

PubMed

Song, Yan-xia; Ma, Qiang; Li, Jie

2015-03-01

Endophytic fungi which reside in the tissue of mangrove plants seem to play an important role in the discovery of new biologically active substances. During the course of screening for the antimicrobial metabolites from the endophytic fugus Penicillium sp. FJ-1 of mangrove plant Avicennia marina, a new aurone glycoside (1) was isolated by repeated column chromatography on silica gel and recrystallization methods. The structure of 1 was elucidated as (Z)-7,4'-dimethoxy-6-hydroxy-aurone-4-O-β-glucopyranoside, on the basis of spectroscopic analysis. Compound 1 exhibited antifungal activity against Candida sp., with the potency comparable to amphotericin B and much better than fluconazole. Compound 1 can also inhibit extracellular phospholipase secretion in a concentration-dependent manner.

Discourse for slide presentation: An overview of chemical detection systems

NASA Technical Reports Server (NTRS)

Peters, Randy Alan; Galen, Theodore J.; Pierson, Duane L.

1990-01-01

A brief overview of some of the analytical techniques currently used in monitoring and analyzing permanent gases and selected volatile organic compound in air are presented. Some of the analytical considerations in developing a specific method are discussed. Four broad groups of hardware are discussed: compound class specific personal monitors, gas chromatographic systems, infrared spectroscopic systems, and mass spectrometric residual gas analyzer systems. Three types of detectors are also discussed: catalytic sensor based systems, photoionization detectors, and wet or dry chemical reagent systems. Under gas chromatograph based systems five detector systems used in combination with a GC are covered: thermal conductivity detectors, photoionization detectors, Fourier transform infrared spectrophotometric systems, quadrapole mass spectrometric systems, and a relatively recent development, a surface acoustic wave vapor detector.

Multispectroscopic investigation of the interaction of BSA and DNA with the anticancer drug, N-(6-ferrocenyl-2-naphthoyl)-gamma-amino butyric acid methyl ester

NASA Astrophysics Data System (ADS)

Rajina, S. R.; Sudhi, Geethu; Austin, P.; Praveen, S. G.; Xavier, T. S.; Kenny, Peter T. M.; Binoy, J.

2018-05-01

The interaction of a drug with DNA and BSA play a great role in studying anti cancer activity and drug transport properties, which can be effectively, investigated using vibrational spectroscopy, UV visible spectroscopy and Fluorescence spectroscopy. The present work reports the structural features of N-(6-ferrocenyl-2-naphthoyl)-gamma-amino butyric acid Methyl ester (FNGABME) based on FTIR and FTRaman spectroscopy. The absorption and fluorescence spectroscopic methods were used to study the efficiency of the interaction of the compound FNGABME with BSA and DNA and also molecular docking were performed computationally to validate the results which shows that the title compound may exhibit inhibitory activity against the cancer cells.

Anti-inflammatory and antimicrobial coumarins from the stems of Eurya chinensis.

PubMed

Song, Jia-Ling; Yuan, Yao; Tan, Hai-Bo; Huang, Ri-Ming; Liu, Hong-Xin; Xu, Zhi-Fang; Qiu, Sheng-Xiang

2017-03-01

Two new coumarins, named (±)-euryacoumarin A (1) and 6-demethylobtusinin (2), and one new natural coumarin, named euryacoumarin B (3), along with two known compounds, scopoletin (4) and obtusinol (5), were isolated from the stems of Eurya chinensis. Their structures were elucidated by means of extensive spectroscopic methods and comparison with data reported in the literatures. Compound 1 exhibited significant inhibition of LPS-induced nitric oxide (NO) production in RAW264.7 cells with IC 50 value of 35.64 ± 1.73 μM, and showed marginal antibacterial activities against Bacillus subtilis and B. cereus with MIC values of 50.59 ± 2.12 and 35.42 ± 0.96 μM, respectively.

Trifasciatosides A-J, Steroidal Saponins from Sansevieria trifasciata.

PubMed

Teponno, Rémy Bertrand; Tanaka, Chiaki; Jie, Bai; Tapondjou, Léon Azefack; Miyamoto, Tomofumi

2016-01-01

Four previously unreported steroidal saponins, trifasciatosides A-D (1-4), three pairs of previously undescribed steroidal saponins, trifasciatosides E-J (5a, b-7a, b) including acetylated ones, together with twelve known compounds were isolated from the n-butanol soluble fraction of the methanol extract of Sansevieria trifasciata. Their structures were elucidated on the basis of detailed spectroscopic analysis, including (1)H-NMR, (13)C-NMR, (1)H-(1)H correlated spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC), total correlated spectroscopy (TOCSY), nuclear Overhauser enhancement and exchange spectroscopy (NOESY), electrospray ionization-time of flight (ESI-TOF)-MS and chemical methods. Compounds 2, 4, and 7a, b exhibited moderate antiproliferative activity against HeLa cells.

Phytochemical and antioxidant activity studies on Ononis angustissima L. aerial parts: isolation of two new flavonoids.

PubMed

Mezrag, Abderrahmane; Malafronte, Nicola; Bouheroum, Mohamed; Travaglino, Carmen; Russo, Daniela; Milella, Luigi; Severino, Lorella; De Tommasi, Nunziatina; Braca, Alessandra; Dal Piaz, Fabrizio

2017-03-01

Ononis angustissima aerial parts extract and exudate were subjected to phytochemical and biological studies. Two new natural flavonoids, (3S)-7-hydroxy-4'-methoxy-isoflavanone 3'-β-d-glucopyranoside (1) and kaempferol 3-O-β-d-glucopyranoside-7-O-(2'''-acetyl)-β-d-galactopyranoside (4), and sixteen known compounds were isolated through a bio-oriented approach. Their structural characterisation was achieved using spectroscopic analyses including 2D NMR. The phytochemical profile of the extracts was also performed, and the antioxidant activity of all compounds was tested by three different assays. To get a trend in the results and to compare the antioxidant capacity among the different methods used, the obtained data were transformed to a relative antioxidant capacity index.

Pentasaccharide resin glycosides from Ipomoea pes-caprae.

PubMed

Yu, Bang-Wei; Luo, Jian-Guang; Wang, Jun-Song; Zhang, Dong-Ming; Yu, Shi-Shan; Kong, Ling-Yi

2011-04-25

Pescapreins XXI-XXX (1-10), pentasaccharide resin glycosides, together with the known pescapreins I-IV and stoloniferin III were isolated from the aerial parts of Ipomoea pes-caprae (beach morning-glory). The pescapreins are macrolactones of simonic acid B, partially esterified with different fatty acids. The lactonization site of the aglycone, jalapinolic acid, was located at C-2 or C-3 of the second saccharide moiety. Their structures were established by a combination of spectroscopic and chemical methods. Compounds 1-10 were evaluated for their potential to modulate multidrug resistance in the human breast cancer cell line MCF-7/ADR. The combined use of these new compounds at a concentration of 5 μg/mL increased the cytotoxicity of doxorubicin by 1.5-3.7-fold.

Compositional control of continuously graded anode functional layer

NASA Astrophysics Data System (ADS)

McCoppin, J.; Barney, I.; Mukhopadhyay, S.; Miller, R.; Reitz, T.; Young, D.

2012-10-01

In this work, solid oxide fuel cells (SOFC's) are fabricated with linear-compositionally graded anode functional layers (CGAFL) using a computer-controlled compound aerosol deposition (CCAD) system. Cells with different CGAFL thicknesses (30 um and 50 um) are prepared with a continuous compositionally graded interface deposited between the electrolyte and anode support current collecting regions. The compositional profile was characterized using energy dispersive X-ray spectroscopic mapping. An analytical model of the compound aerosol deposition was developed. The model predicted compositional profiles for both samples that closely matched the measured profiles, suggesting that aerosol-based deposition methods are capable of creating functional gradation on length scales suitable for solid oxide fuel cell structures. The electrochemical performances of the two cells are analyzed using electrochemical impedance spectroscopy (EIS).

Cytotoxic principles from the formosan milkweed, Asclepias curassavica.

PubMed

Roy, Michael C; Chang, Fang-Rong; Huang, Hsiao-Chu; Chiang, Michael Y-N; Wu, Yang-Chang

2005-10-01

A series of cardenolides and related compounds have been isolated from the aerial parts and roots of the ornamental milkweed, Asclepias curassavica. Their structures were determined by spectroscopic and chemical methods. Among them, three derivatives of calactinic acid methyl ester (13-15), 19-nor-16 alpha-acetoxy-10 beta-hydroxyasclepin (16), 20 beta,21-dihydroxypregna-4,6-dien-3-one (19), and 3,4-seco-urs-20(30)-en-3-oic acid (22) are new compounds. The relative configuration of calactinic acid methyl ester (12) has been confirmed by X-ray diffraction analysis on its derivative 13. Most of the cardenolides obtained showed pronounced cytotoxicity against four cancer cell lines (IC(50) 0.01 to 2.0 microg/mL).

Cytotoxic constituents of ethyl acetate fraction from Dianthus superbus.

PubMed

Ding, Chengli; Zhang, Wu; Li, Jie; Lei, Jiachuan; Yu, Jianqing

2013-01-01

The ethyl acetate fraction (EE-DS) from Dianthus superbus was found to possess the cytotoxic activity against cancer cells in previous study. To investigate cytotoxic constituents, the bioassay-guided isolation of compounds from EE-DS was performed. Two dianthramides (1 and 2), three flavonoids (3-5), two coumarins (6 and 7) and three other compounds (8-10) were obtained. Structures of isolated compounds were identified by spectroscopic analysis. Cytotoxicity of the compounds against HepG2 cells was evaluated. Compound 1 showed the strongest cytotoxicity, compounds 10, 4, 3 and 5 had moderate cytotoxicity.

Optical properties of novel environmentally benign biologically active ferrocenyl substituted chromophores: A detailed insight via experimental and theoretical approach

NASA Astrophysics Data System (ADS)

Khan, Salman A.; Asiri, Abdullah M.; Al-Ghamdi, Najat Saeed M.; Zayed, Mohie E. M.; Sharma, Kamlesh; Parveen, Humaira

2017-07-01

Series of ferrocenyl substituted chromophores were synthesized via a reaction of acetyl ferrocene and a variety of aldehyde under microwave irradiation. The structure of synthesized compounds were established by spectroscopic (FT-IR, 1H NMR, 13C NMR, ESI-MS) and elemental analysis. UV-Vis and fluorescence spectroscopy measurements provided that all compounds have good absorbent and fluorescent properties. Fluorescence polarity studies demonstrated that these compounds were sensitive to the polarity of the microenvironment provided by different solvents. In addition, spectroscopic and physicochemical parameters, including singlet absorption, extinction coefficient, Stokes shift, oscillator strength and dipole moment, were investigated in order to explore the analytical potential of the synthesized compounds. The anti-bacterial activity of these compounds were first studied in vitro by the disk diffusion assay against two Gram-positive and two Gram-negative bacteria. The minimum inhibitory concentration was then determined with the reference of standard drug chloramphenicol. The results displayed that compound 3 was better inhibitors for both types of the bacteria (Gram-positive and Gram-negative) than chloramphenicol. Based on the density functional theory; total energy, the atomic orbital contribution to frontier orbitals: LUMO and HOMO, of all synthesized compounds were calculated to support the antibacterial activities.

The Antimicrobial Activities of Extract and Compounds Isolated from Brillantaisia lamium

PubMed Central

Tamokou, Jean De Dieu; Kuiate, Jules Roger; Tene, Mathieu; Kenla Nwemeguela, Timothée Julbelin; Tane, Pierre

2011-01-01

Background: Brillantaisia lamium is an erect branched herb, which grows to a height of 1.50 m in moist tropical areas, both in full sun and partial shade. In , the aerial part of this plant is used in the treatment of various microbial infections such as skin diseases and infections of urinary tract. The aim of this study was to evaluate the antimicrobial activities of CH2Cl2: MeOH (1:1) extract, fractions and compounds from the aerial part of B. lamium. Methods: The plant was dried and extracted by maceration in CH2Cl2: MeOH (1:1 v/v). Structures of the compounds from the CH2Cl2: MeOH (1:1) soluble fraction were determined by spectroscopic methods and compared with published data. The broth micro dilution method was used to evaluate the antimicrobial activities against bacteria and fungal species. Results: Four known compounds: aurantiamide acetate (1), lupeol (2), lespedin (3), sitosterol 3-O-β-D-glucopyranoside (4) and a mixture of sterols: campesterol (5), stigmasterol (6) and β-sitosterol (7) were isolated from CH2Cl2: MeOH (1:1) extract of B. lamium aerial parts. The crude extract, fractions and isolated compounds exhibited both antibacterial and antifungal activities that varied with microorganism (MIC=6.25 – 1000 µg/ml). Compound 3 was the most active (MIC=6.25 – 100 µg/ml) while Staphylococcus aureus, Enterococcus faecalis, Candida tropicalis and Cryptococcus neoformans were the most sensitive to all the tested compounds. Conclusion: The overall results of this study indicate that the CH2Cl2: MeOH (1:1) extract and some of isolated compounds have interesting antimicrobial properties and can be used for the treatment of fungal and bacterial infections. PMID:23365474

Penialidins A-C with strong antibacterial activities from Penicillium sp., an endophytic fungus harboring leaves of Garcinia nobilis.

PubMed

Jouda, Jean-Bosco; Kusari, Souvik; Lamshöft, Marc; Mouafo Talontsi, Ferdinand; Douala Meli, Clovis; Wandji, Jean; Spiteller, Michael

2014-10-01

Three new polyketides named penialidins A-C (1-3), along with one known compound, citromycetin (4), were isolated from an endophytic fungus, Penicillium sp., harbored in the leaves of the Cameroonian medicinal plant Garcinia nobilis. Their structures were elucidated by means of spectroscopic and spectrometric methods (NMR and HRMS(n)). The antibacterial efficacies of the new compounds (1-3) were tested against the clinically-important risk group 2 (RG2) bacterial strains of Staphylococcus aureus and Escherichia coli. The ecologically imposing strains of E. coli (RG1), Bacillus subtilis and Acinetobacter sp. BD4 were also included in the assay. Compound 3 exhibited pronounced activity against the clinically-relevant S. aureus as well as against B. subtilis comparable to that of the reference standard (streptomycin). Compound 2 was also highly-active against S. aureus. By comparing the structures of the three new compounds (1-3), it was revealed that altering the substitutions at C-10 and C-2 can significantly increase the antibacterial activity of 1. Copyright © 2014 Elsevier B.V. All rights reserved.

1D helical cadmium coordination polymers containing hydrazide ligand: The role of solvent and molar ratio

NASA Astrophysics Data System (ADS)

Notash, Behrouz

2018-03-01

Three new cadmium coordination polymers, [Cd(L)(NO3)2CH3OH]n, 1, {[Cd(L)2(NO3)]NO3}n, 2 and {[Cd(L)2(NO3)]NO3.H2O}n3, which L is nicotinohydrazide have been synthesized and characterized by spectroscopic methods as well as single crystal X-ray diffraction. Compounds 1-3 have been synthesized by changing solvent and metal-to-ligand ratio. X-ray crystallography showed that compounds 1-3 have different 1D helical structural motif. Semi-flexible nature of L ligand causes to syn-syn conformation which leading to form 1D helical chains coordination polymers. Compounds 2 and 3 were synthesized under the same reaction conditions with similar molar ratio, but using different solvent system. These compounds are pseudopolymorph which differs in the presence or absence of water molecule in their crystal packing. Hirshfeld surface analysis of the structures 1-3 have been performed and find the percent of participation of intermolecular interactions in the crystal packing of compounds.

Toxicological methods for tracing drug abuse: chromatographic, spectroscopic and biological characterisation of ecstasy derivatives.

PubMed

Belhadj-Tahar, Hafid; Payoux, Pierre; Tafani, Mathieu; Coulais, Yvon; Calet, Serge; Bousseksou, Azzedine

2010-03-01

Analysis often reveals variability in the composition of ecstasy pills from pure 3,4-methylenedioxymethamphetamine (MDMA) to mixtures of MDMA derivatives, amphetamine, and other unidentified substances. For a comprehensive toxicological analysis one needs to know all steps to MDMA synthesis which may originate impurities. The aim of this study was to synthesise and determine the chemical-physical and in vitro biological properties of a series of MDMA derivatives.3,4-methylendioxyphenyl-2-nitropropene (MDNP) was obtained by condensation of piperonal with an excess of nitroethane in the presence of ammonium acetate. MDNP was then reduced to methylenedioxyamphetamine (MDA) by LiAlH3. All compounds were analysed using HPLC and spectroscopic technique [Raman, nuclear magnetic resonance (NMR), or infrared (IR)] at all the steps of synthesis. In addition, we assessed the biological potentials of these compounds by measuring in vitro their (i) blood cell/whole blood partition coefficient, (ii) binding to plasmatic proteins (Fbp), and (iii) membrane adsorption. Chemical structure was determined with antibody fluorescence polarisation immunoassay (FPIA). This study showed the presence of solid impurities, particularly of a neurotoxic compound of Al3+ in the final products. FPIA identified the aminoethane group close to the substituted benzene ring, but did not detect the two major precursors of MDMA: MDNP and piperonal. Raman spectroscopy is an attractive alternative technique to characterise ecstasy pills and it can identify stereoisomeric forms such as cis-MDNP and trans-MDNP, which exhibit signals at 1650 cm-1 and 1300 cm-1, respectively.

Solid state synthesis, structural, physicochemical and optical properties of an inter-molecular compound: 2-hydroxy-1, 2-diphenylethanone-4-nitro-o-phenylenediamine system

NASA Astrophysics Data System (ADS)

Rai, U. S.; Singh, Manjeet; Rai, R. N.

2017-09-01

The phase diagram of 2-hydroxy-1, 2-diphenylethanone (HDPE)-4-nitro-o-phenylenediamine (NOPDA) system, determined by the thaw-melt method, gives two eutectics E1 (m p = 66.0 °C) and E2 (m p = 155.0 °C) with 0.30 and 0.55 mol fractions of NOPDA, respectively, and an 1:1 inter-molecular compound (IMC) (m p 162.0 °C). This IMC was synthesized by adopting the green synthetic method of solid state reaction. While its formation and structure were confirmed by the X-ray diffraction and spectroscopic methods, the ORTEP view gives mode of crystal packing, C‒H…O, C‒H…N, π-π stacking and the inter-molecular hydrogen bonding in the compound. The single crystal of the IMC shows 53% transmission and emits significantly higher dual fluorescence, and the band gap was computed to be 3.04 eV. The values of solubility of the IMC, measured in the temperature range 304-322 K, satisfy the mole fraction (X) and temperature equation: Xeq= 5.1324 × 10-7 e 0.01356T.

Electronic structure of the alkyne-bridged dicobalt hexacarbonyl complex Co(2) micro-C(2)H(2) (CO)(6): evidence for singlet diradical character and implications for metal-metal bonding.

PubMed

Platts, James A; Evans, Gareth J S; Coogan, Michael P; Overgaard, Jacob

2007-08-06

A series of ab initio calculations are presented on the alkyne-bridged dicobalt hexacarbonyl cluster Co2 micro-C2H2 (CO)6, indicating that this compound has substantial multireference character, which we interpret as evidence of singlet diradical behavior. As a result, standard theoretical methods such as restricted Hartree-Fock (RHF) or Kohn-Sham (RKS) density functional theory cannot properly describe this compound. We have therefore used complete active space (CAS) methods to explore the bonding in and spectroscopic properties of Co2 micro-C2H2 (CO)6. CAS methods identify significant population of a Co-Co antibonding orbital, along with Co-pi* back-bonding, and a relatively large singlet-triplet energy splitting. Analysis of the electron density and related quantities, such as energy densities and atomic overlaps, indicates a small but significant amount of covalent bonding between cobalt centers.

A new look into the quantum chemical and spectroscopic investigations of 5-chloro-1-methyl-4-nitroimidazole.

PubMed

Arjunan, V; Raj, Arushma; Anitha, R; Mohan, S

2014-05-05

Optimised geometrical structural parameters, harmonic vibrational frequencies, natural bonding orbital analysis and frontier molecular orbitals are determined by B3LYP and B3PW91 methods. The exact geometry of 5-chloro-1-methyl-4-nitroimidazole is determined through conformational analysis. The experimentally observed infrared and Raman bands have been assigned and analysed. The (13)C and (1)H NMR chemical shifts of the compound are investigated. The total electron density and molecular electrostatic potentials are determined. The electrostatic potential (electron+nuclei) distribution, molecular shape, size and dipole moments of the molecule have been displayed. The energies of the frontier molecular orbitals and LUMO-HOMO energy gap are measured. The possible electronic transitions of the molecule are studied by TD-DFT method along with the UV-Visible spectrum. The structure-activity relationship of the compound is also investigated by conceptual DFT methods. Copyright © 2014 Elsevier B.V. All rights reserved.

An Unusual Conformational Isomer of Verrucosidin Backbone from a Hydrothermal Vent Fungus, Penicillium sp. Y-50-10

PubMed Central

Pan, Chengqian; Shi, Yutong; Auckloo, Bibi Nazia; Chen, Xuegang; Chen, Chen-Tung Arthur; Tao, Xinyi; Wu, Bin

2016-01-01

A new verrucosidin derivative, methyl isoverrucosidinol (1), was isolated from the marine fungus Penicillium sp. Y-50-10, dwelling in sulfur rich sediment in the Kueishantao hydrothermal vents off Taiwan. The structure was established by spectroscopic means including HRMS and 2D-NMR spectroscopic analysis. The absolute configuration was defined mainly by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Among hitherto known compounds with a verrucosidine backbone isolated from natural resource, compound 1 represents the first example of a new conformational isomer of its skeleton, exhibiting antibiotic activity against Bacillus subtilis with MIC value 32 μg/mL. PMID:27548192

8-9' linked neolignans with cytotoxicity from Alpinia conchigera.

PubMed

Xu, Jun-Ju; Zeng, Guang-Zhi; Yang, Sheng-Chao; Shen, Yong; Tan, Ning-Hua

2013-12-01

Five new 8-9' linked neolignans conchigeranals A-E (1-5), together with three known compounds galanganal (6), galanganols A (7) and B (8), were isolated from the whole plant of Alpinia conchigera. Their structures were established by spectroscopic analysis, including 2D-NMR spectroscopic techniques. Cytotoxicities of compounds 1-8 were tested against two cancer cell lines A549 and Hela. Results showed that 4, 5, 7 and 8 exhibited cytotoxicity against A549 with the IC50 values of 12.36, 9.72, 10.26, 13.05 μg/ml, respectively, and 1-8 against Hela with the IC50 values from 1.53 to 5.29 μg/ml. © 2013.

Spectroscopic identification and anti-biofilm properties of polar metabolites from the medicinal plant Helichrysum italicum against Pseudomonas aeruginosa.

PubMed

D'Abrosca, Brigida; Buommino, Elisabetta; D'Angelo, Grazia; Coretti, Lorena; Scognamiglio, Monica; Severino, Valeria; Pacifico, Severina; Donnarumma, Giovanna; Fiorentino, Antonio

2013-11-15

Two new acylated styrylpyrones, one 5-methoxy-1(3H)-isobenzofuranone glucoside and a hydroxymethyl-orcinol derivative, along with sixteen known aromatic metabolites, including lignans, quinic acid derivatives low-molecular weight phenol glucosides, have been isolated from the methanol extract of Helichrysum italicum, a medicinal plant typical of the Mediterranean vegetation. The structures of these compounds have been elucidated on the basis of extensive 2D-NMR spectroscopic analyses, including COSY, TOCSY, HSQC, CIGAR-HMBC, H2BC and HSQC-TOCSY, along with Q-TOF HRMS(2) analysis. Selected compounds were evaluated for their anti-biofilm properties against Pseudomonas aeruginosa. Copyright © 2013. Published by Elsevier Ltd.

Isolation, spectroscopic and density functional theory studies of 7-(4-methoxyphenyl)-9H-furo[2,3-f]chromen-9-one: a new flavonoid from the bark of Millettia ovalifolia.

PubMed

Taj Ur Rahman; Arfan, Mohammad; Mahmood, Tariq; Liaqat, Wajiha; Gilani, Mazhar Amjad; Uddin, Ghias; Ludwig, Ralf; Zaman, Khair; Choudhary, M Iqbal; Khattak, Khanzadi Fatima; Ayub, Khurshid

2015-07-05

The phytochemical examination of chloroform soluble fraction (FX2) of methanolic extract of bark of Millettia ovalifolia yielded a new flavonoid; 7-(4-methoxyphenyl)-9H-furo [2,3-f]chromen-9-one (1). Compound 1 is characterized by spectroscopic analytical techniques such as UV, IR, 1D, 2D NMR spectroscopy, and mass spectrometry. A theoretical model is also developed for obtaining geometric, electronic and spectroscopic properties of 1. The geometry optimization and harmonic vibration simulations have been carried out at B3LYP/6-31G(d,p). The vibrational spectrum of compound 1 shows nice correlation with the experimental IR spectrum, through a scaling factor of 0.9613. (1)H and (13)C NMR chemical shifts are simulated using Cramer's re-parameterized function WP04 at 6-31G(d,p) basis set, and correlate nicely with the experimental chemical shifts. Copyright © 2015 Elsevier B.V. All rights reserved.

Isolation, spectroscopic and density functional theory studies of 7-(4-methoxyphenyl)-9H-furo[2,3-f]chromen-9-one: A new flavonoid from the bark of Millettia ovalifolia

NASA Astrophysics Data System (ADS)

Rahman, Taj Ur; Arfan, Mohammad; Mahmood, Tariq; Liaqat, Wajiha; Gilani, Mazhar Amjad; Uddin, Ghias; Ludwig, Ralf; Zaman, Khair; Choudhary, M. Iqbal; Khattak, Khanzadi Fatima; Ayub, Khurshid

2015-07-01

The phytochemical examination of chloroform soluble fraction (FX2) of methanolic extract of bark of Millettia ovalifolia yielded a new flavonoid; 7-(4-methoxyphenyl)-9H-furo [2,3-f]chromen-9-one (1). Compound 1 is characterized by spectroscopic analytical techniques such as UV, IR, 1D, 2D NMR spectroscopy, and mass spectrometry. A theoretical model is also developed for obtaining geometric, electronic and spectroscopic properties of 1. The geometry optimization and harmonic vibration simulations have been carried out at B3LYP/6-31G(d,p). The vibrational spectrum of compound 1 shows nice correlation with the experimental IR spectrum, through a scaling factor of 0.9613. 1H and 13C NMR chemical shifts are simulated using Cramer's re-parameterized function WP04 at 6-31G(d,p) basis set, and correlate nicely with the experimental chemical shifts.

Sterols isolated from Nuruk (Rhizopus oryzae KSD-815) inhibit the migration of cancer cells.

PubMed

Lee, Dae-Young; Lee, Sang-Jin; Kwak, Ho-Young; Jung, Lakoon; Heo, Jieun; Hong, Sungyoul; Kim, Gye-Won; Baek, Nam-In

2009-11-01

An activity-guided fractionation method was used to isolate anticancer components from Nuruk (Rhizopus oryzae KSD-815:KSD-815). Dried powder of KSD-815 was extracted with 80% methanol and partitioned successively using nhexane, ethyl acetate, n-butanol, and water. The n-hexane and n-butanol fractions showed a strong antimigratory effect on human cancer cells. Both of these fractions were subjected to separation and purification procedures using silica gel, octadecyl silica gel, and Sephadex LH-20 column chromatographies to afford four purified compounds. These were identified as ergosterol peroxide (1), stigmast- 5-en-3beta,7beta-diol (2), ergosta-7,22-dien-3beta,5alpha,6beta,9alpha-tetraol (3), and daucosterol (4), respectively, by spectroscopic methods such as nuclear magnetic resonance spectrometry, mass spectrometry, and infrared spectroscopy, and comparison with those in the literature. Compounds 1-4 were isolated from KSD-815 for the first time. Compounds 1 and 4 inhibited the migration of MDA-MB-231 cells at concentrations lower than 20 micronM.

Structure elucidation of two novel yak milk oligosaccharides and their DFT studies

NASA Astrophysics Data System (ADS)

Singh, Ashish Kumar; Ranjan, Ashok Kr.; Srivastava, Gaurav; Deepak, Desh

2016-03-01

Milk is a primary dynamic biological fluid responsible for development of neonates. Besides the other regular constituents it have oligosaccharides in it which are responsible for antitumor, anticancer, antigenic and immunostimulant activities. In our endeavor to find biologically active novel oligosaccharides, yak milk was taken, which is a rich source of oligosaccharide and its milk is used as antihypertensive, antioxidative and heart strengthening agent in folk medicine. For this purpose yak milk was processed by method of Kobata and Ginsburg followed by gel filtration HPLC and CC which resulted in the isolation of two novel milk oligosaccharides namely (I) Grunniose and (II) Vakose. The structure of purified milk oligosaccharides were elucidated with the help of chemical degradation, chemical transformation, spectroscopic techniques like NMR (1H, 13C and 2D-NMR), structure reporter group theory and mass spectrometry. The optimized geometry of compound Grunniose and Vakose, at B3LYP method and 6-311 + G basis set on Gaussian 09 program, show that the compound Grunniose is lower in energy as compared to compound Vakose.

In vitro anti-acne activity of phytoactives from the stem bark of Artocarpus hirsutus Lam. and characterisation of pyranocycloartobiloxanthone A as a mixture of two anomers.

PubMed

Nayak, Mahadeva; Nagarajan, A; Majeed, Muhammed; Nagabhushanam, Kalyanam; Choudhury, Ambar K

2017-08-18

This study is aimed to isolate the phytoactives from the stem bark of Artocarpus hirsutus and evaluate their in vitro anti-acne activity. The ethanolic stem bark extract of A. hirsutus provided two major phytoactive constituents: (i) pyranocycloartobiloxanthone A, (1) and (ii) Artonine E, (2) whose structures were determined by NMR and MS spectroscopic analysis. The present study is the first to report compound 1 as a mixture of two anomers (α and β), approximately 70:30 ratio. Both compounds 1 and 2 were isolated for the first time from this plant. In vitro anti-acne activity of compounds 1 and 2 were evaluated by agar well diffusion method and the minimum inhibition was determined by broth micro dilution method. The result of anti-microbial activity (MIC = 2.0 μg/mL each) is comparable to antibiotic, Clindamycin (MIC = 0.03 μg/mL) and clearly demonstrate their potential as anti-acne agents.

A novel pyrrole alkaloid from the fruit peels of Strychnos nux-blanda.

PubMed

Sichaem, Jirapast; Ingkaninan, Kornkanok; Tip-Pyang, Santi

2017-01-01

A novel pyrrole alkaloid, strychnuxin (1), along with five known compounds (2-6) was isolated from the fruit peels of Strychnos nux-blanda. The structures of all the isolated compounds (1-6) were fully characterised using spectroscopic data, as well as comparison with the previous literature data. Moreover, all isolated compounds were assessed for their α-glucosidase and acetylcholinesterase inhibitory activities.

DFT based vibrational spectroscopic investigations and biological activity of toxic material monocrotophos

NASA Astrophysics Data System (ADS)

Nimmi, D. E.; Sam, S. P. Chandhini; Praveen, S. G.; Binoy, J.

2018-05-01

Many organophosphate compounds exhibiting toxicity are widely used as pesticides and insecticides whose structural features can be explained excellently using geometric simulation using density functional theory and vibrational spectrum. In this work, the molecular structural parameters and vibrational frequencies of the fundamental modes of Monocrotophoshave been obtained using Density functional theory (DFT), using B3LYP functional with 6-311++G(d, p) basis sets and the detailed vibrational analysis of FT-IR and FT-Ramanspectral bands have been carried out using potential energy distribution (PED). The deviation from the resonance structure of phosphate group due to `bridging of oxygen' and π-resonance of amides has been investigated based on the spectral and geometric data. The molecular docking simulation of Monocrotophos with BSA and DNA has been performed to find the mode of binding and the interactions with BSA has been investigated with UV-Visible spectroscopic method, to assess the strength of binding.

Spectroscopic methods for the study of energetic characteristics of the normal and photoproduct forms of 3-hydroxyflavones.

PubMed

Ushakou, Dzmitryi V; Tomin, Vladimir I

2018-06-07

We report spectroscopic properties of 3-hydroxyflavone (3-HF) and 4'-N,N-dimethylamino-3-hydroxyflavone (DMA3HF) in acetonitrile and ethyl acetate at different temperatures in the range from 10 °C to about 67 °C. These compounds are characterized by excited-state intramolecular proton transfer (ESIPT) which leads to occurrence of two forms of these molecules. For this reason their fluorescence spectra have two bands which correspond to emission of normal and photoproduct (tautomer) forms. The correlation between ratio of integrated intensity of these two bands and inverse absolute temperature (the Arrhenius plot) have been applied to estimate energetic properties, such as difference between energy levels of excited states as well ground states for normal and tautomer forms for each molecule. Copyright © 2018 Elsevier B.V. All rights reserved.

Spectroscopic and chemical reactivity analysis of D-Myo-Inositol using quantum chemical approach and its experimental verification

NASA Astrophysics Data System (ADS)

Mishra, Devendra P.; Srivastava, Anchal; Shukla, R. K.

2017-07-01

This paper describes the spectroscopic (^1H and ^{13}C NMR, FT-IR and UV-Visible), chemical, nonlinear optical and thermodynamic properties of D-Myo-Inositol using quantum chemical technique and its experimental verification. The structural parameters of the compound are determined from the optimized geometry by B3LYP method with 6 {-}311{+}{+}G(d,p) basis set. It was found that the optimized parameters thus obtained are almost in agreement with the experimental ones. A detailed interpretation of the infrared spectra of D-Myo-Inositol is also reported in the present work. After optimization, the proton and carbon NMR chemical shifts of the studied compound are calculated using GIAO and 6 {-}311{+}{+}G(d,p) basis set. The search of organic materials with improved charge transfer properties requires precise quantum chemical calculations of space-charge density distribution, state and transition dipole moments and HOMO-LUMO states. The nature of the transitions in the observed UV-Visible spectrum of the compound has been studied by the time-dependent density functional theory (TD-DFT). The global reactivity descriptors like chemical potential, electronegativity, hardness, softness and electrophilicity index, have been calculated using DFT. The thermodynamic calculation related to the title compound was also performed at B3LYP/ 6 {-}311{+}{+}G(d,p) level of theory. The standard statistical thermodynamic functions like heat capacity at constant pressure, entropy and enthalpy change were obtained from the theoretical harmonic frequencies of the optimized molecule. It is observed that the values of heat capacity, entropy and enthalpy increase with increase in temperature from 100 to 1000 K, which is attributed to the enhancement of molecular vibration with the increase in temperature.

Synthesis of Some Novel Thiadiazole Derivative Compounds and Screening Their Antidepressant-Like Activities.

PubMed

Can, Nafiz Öncü; Can, Özgür Devrim; Osmaniye, Derya; Demir Özkay, Ümide

2018-03-21

Novel thiadiazole derivatives were synthesized through the reaction of acetylated 2-aminothiadiazole and piperazine derivatives. The chemical structures of the compounds were clarified by Infrared Spectroscopy (IR), ¹H Nuclear Magnetic Resonance Spectroscopy (¹H-NMR), 13 C Nuclear Magnetic Resonance Spectroscopy ( 13 C-NMR) and Electronspray Ionisation Mass Spectroscopy (ESI-MS) spectroscopic methods. Antidepressant-like activities were evaluated by the tail-suspension (TST) and modified forced swimming (MFST) methods. Besides, possible influence of the test compounds on motor activities of the animals were examined by activity cage tests. In the TST, administration of the compounds 2c , 2d , 2e , 2f , 2g and 2h significantly decreased the immobility time of mice regarding the control values. Further, in the MFST, the same compounds reduced the total number of immobility behaviors while increasing swimming performance. However, no change was observed in the total number of climbing behaviors. These data suggested that compounds 2c , 2d , 2e , 2f , 2g and 2h possess notable antidepressant-like activities. Reference drug fluoxetine (10 mg/kg) was also exhibited its antidepressant activity, as expected. No significant difference was seen between the locomotor activity values of the test groups signifying that observed antidepressant-like activities are specific. Theoretical calculation of absorption, distribution, metabolism, excretion (ADME) properties for the obtained compounds were performed and obtained data supported the antidepressant-like potential of these novel thiadiazole derivatives.

Quality evaluation of fish and other seafood by traditional and nondestructive instrumental methods: Advantages and limitations.

PubMed

Hassoun, Abdo; Karoui, Romdhane

2017-06-13

Although being one of the most vulnerable and perishable products, fish and other seafoods provide a wide range of health-promoting compounds. Recently, the growing interest of consumers in food quality and safety issues has contributed to the increasing demand for sensitive and rapid analytical technologies. Several traditional physicochemical, textural, sensory, and electrical methods have been used to evaluate freshness and authentication of fish and other seafood products. Despite the importance of these standard methods, they are expensive and time-consuming, and often susceptible to large sources of variation. Recently, spectroscopic methods and other emerging techniques have shown great potential due to speed of analysis, minimal sample preparation, high repeatability, low cost, and, most of all, the fact that these techniques are noninvasive and nondestructive and, therefore, could be applied to any online monitoring system. This review describes firstly and briefly the basic principles of multivariate data analysis, followed by the most commonly traditional methods used for the determination of the freshness and authenticity of fish and other seafood products. A special focus is put on the use of rapid and nondestructive techniques (spectroscopic techniques and instrumental sensors) to address several issues related to the quality of these products. Moreover, the advantages and limitations of each technique are reviewed and some perspectives are also given.

Chloromonilinic Acids C and D, Phytotoxic Tetrasubstituted 3-Chromanonacrylic Acids Isolated from Cochliobolus australiensis with Potential Herbicidal Activity against Buffelgrass (Cenchrus ciliaris).

PubMed

Masi, Marco; Meyer, Susan; Clement, Suzette; Pescitelli, Gennaro; Cimmino, Alessio; Cristofaro, Massimo; Evidente, Antonio

2017-10-27

The fungal pathogen Cochliobolus australiensis isolated from infected leaves of the invasive weed buffelgrass (Pennisetum ciliare) was grown in vitro to evaluate its ability to produce phytotoxic metabolites that could potentially be used as natural herbicides against this weed. Two new tetrasubstituted 3-chromanonacrylic acids, named chloromonilinic acids C (1) and D (2), were isolated from the liquid cultures of C. australiensis, together with the known chloromonilinic acid B. Chloromonilinic acids C and D were characterized by spectroscopic and chemical methods as (E)-3-chloro-3-[(5-hydroxy-3-(1-hydroxy-2-methoxy-2-oxoethyl)-7-methyl-4-oxo-4H-chromen-2-yl)]acrylic acid and (Z)-3-chloro-3-[(5-hydroxy-3-(2-methoxy-2-oxoethyl)-7-methyl-4-oxo-4H-chromen-2-yl)]acrylic acid, respectively. The stereochemistry of chloromonilinic acids C and D was determined using a combination of spectroscopic and computational methods, including electronic circular dichroism. The fungus produced these compounds in two different liquid media together with cochliotoxin, radicinin, radicinol, and their 3-epimers. The radicinin-related compounds were also produced when the fungus was grown in wheat seed solid culture, but chloromonilinic acids were not found in the solid culture organic extract. All three chloromonilinic acids were toxic to buffelgrass in a seedling elongation bioassay, with significantly delayed germination and dramatically reduced radicle growth, especially at a concentration of 5 × 10 -3 M.

Synthesis and Antidepressant Activity Profile of Some Novel Benzothiazole Derivatives.

PubMed

Demir Özkay, Ümide; Kaya, Ceren; Acar Çevik, Ulviye; Can, Özgür Devrim

2017-09-07

Within the scope of our new antidepressant drug development efforts, in this study, we synthesized eight novel benzothiazole derivatives 3a - 3h . The chemical structures of the synthesized compounds were elucidated by spectroscopic methods. Test compounds were administered orally at a dose of 40 mg/kg to mice 24, 5 and 1 h before performing tail suspension, modified forced swimming, and activity cage tests. The obtained results showed that compounds 3c , 3d , 3f - 3h reduced the immobility time of mice as assessed in the tail suspension test. Moreover, in the modified forced swimming tests, the same compounds significantly decreased the immobility, but increased the swimming frequencies of mice, without any alteration in the climbing frequencies. These results, similar to the results induced by the reference drug fluoxetine (20 mg/kg, po), indicated the antidepressant-like activities of the compounds 3c , 3d , 3f - 3h . Owing to the fact that test compounds did not induce any significant alteration in the total number of spontaneous locomotor activities, the antidepressant-like effects of these derivatives seemed to be specific. In order to predict ADME parameters of the synthesized compounds 3a - 3h , some physicochemical parameters were calculated. The ADME prediction study revealed that all synthesized compounds may possess good pharmacokinetic profiles.

Preparative separation of sulfur-containing diketopiperazines from marine fungus Cladosporium sp. using high-speed counter-current chromatography in stepwise elution mode.

PubMed

Gu, Binbin; Zhang, Yanying; Ding, Lijian; He, Shan; Wu, Bin; Dong, Junde; Zhu, Peng; Chen, Juanjuan; Zhang, Jinrong; Yan, Xiaojun

2015-01-09

High-speed counter-current chromatography (HSCCC) was successively applied to the separation of three sulfur-containing diketopiperazines (DKPs) (including two new compounds cladosporin A (1) and cladosporin B (3), and a known compound haematocin (2)) from a marine fungus Cladosporium sp. The two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water at (1:1:1:1, v/v) and (2:1:2:1, v/v), in stepwise elution mode, was used for HSCCC. The preparative HSCCC separation was performed on 300 mg of crude sample yielding 26.7 mg of compound 3 at a purity of over 95%, 53.6 mg of a mixture of compounds 1 and 2, which was further separated by preparative-HPLC yielding 14.3 mg of compound 1 and 25.4 mg of compound 2 each at a purity of over 95%. Their structures were established by spectroscopic methods. The sulfur-containing DKPs suppressed the proliferation of hepatocellular carcinoma cell line HepG2. The present work represents the first application of HSCCC in the efficient preparation of marine fungal natural products.

Preparative Separation of Sulfur-Containing Diketopiperazines from Marine Fungus Cladosporium sp. Using High-Speed Counter-Current Chromatography in Stepwise Elution Mode

PubMed Central

Gu, Binbin; Zhang, Yanying; Ding, Lijian; He, Shan; Wu, Bin; Dong, Junde; Zhu, Peng; Chen, Juanjuan; Zhang, Jinrong; Yan, Xiaojun

2015-01-01

High-speed counter-current chromatography (HSCCC) was successively applied to the separation of three sulfur-containing diketopiperazines (DKPs) (including two new compounds cladosporin A (1) and cladosporin B (3), and a known compound haematocin (2)) from a marine fungus Cladosporium sp. The two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water at (1:1:1:1, v/v) and (2:1:2:1, v/v), in stepwise elution mode, was used for HSCCC. The preparative HSCCC separation was performed on 300 mg of crude sample yielding 26.7 mg of compound 3 at a purity of over 95%, 53.6 mg of a mixture of compounds 1 and 2, which was further separated by preparative-HPLC yielding 14.3 mg of compound 1 and 25.4 mg of compound 2 each at a purity of over 95%. Their structures were established by spectroscopic methods. The sulfur-containing DKPs suppressed the proliferation of hepatocellular carcinoma cell line HepG2. The present work represents the first application of HSCCC in the efficient preparation of marine fungal natural products. PMID:25584683

Nicotine, aerosol particles, carbonyls and volatile organic compounds in tobacco- and menthol-flavored e-cigarettes.

PubMed

Lee, Mi-Sun; LeBouf, Ryan F; Son, Youn-Suk; Koutrakis, Petros; Christiani, David C

2017-04-27

We aimed to assess the content of electronic cigarette (EC) emissions for five groups of potentially toxic compounds that are known to be present in tobacco smoke: nicotine, particles, carbonyls, volatile organic compounds (VOCs), and trace elements by flavor and puffing time. We used ECs containing a common nicotine strength (1.8%) and the most popular flavors, tobacco and menthol. An automatic multiple smoking machine was used to generate EC aerosols under controlled conditions. Using a dilution chamber, we targeted nicotine concentrations similar to that of exposure in a general indoor environment. The selected toxic compounds were extracted from EC aerosols into a solid or liquid phase and analyzed with chromatographic and spectroscopic methods. We found that EC aerosols contained toxic compounds including nicotine, fine and nanoparticles, carbonyls, and some toxic VOCs such as benzene and toluene. Higher mass and number concentrations of aerosol particles were generated from tobacco-flavored ECs than from menthol-flavored ECs. We found that diluted machine-generated EC aerosols contain some pollutants. These findings are limited by the small number of ECs tested and the conditions of testing. More comprehensive research on EC exposure extending to more brands and flavor compounds is warranted.

One-dimensional mercury(II) halide coordination polymers of 3,6-bis(2-pyridyl)-1,2,4,5-tetrazine ligand: Synthesis, crystal structure, spectroscopic and DFT studies

DOE Office of Scientific and Technical Information (OSTI.GOV)

Saghatforoush, Lotfali, E-mail: saghatforoush@gmail.com; Khoshtarkib, Zeinab; Amani, Vahid

2016-01-15

Three new coordination polymers, [Hg(μ-bptz)X{sub 2}]{sub n} (X=Cl (1), Br (2)) and [Hg{sub 2}(μ-bptz)(μ-I){sub 2}I{sub 2}]{sub n} (3) (bptz=3,6-bis(2-pyridyl)-1,2,4,5-tetrazine) were synthesized. X-ray structural analysis indicated that compounds 1 and 2 are composed of one-dimensional (1D) linear chains while the compound 3 has 1D stair-stepped structure. The electronic band structure along with density of states (DOS) calculated by the DFT method indicates that compound 1 and 2 are direct band gap semiconductors; however, compound 3 is an indirect semiconductor. The linear optical properties of the compounds are also calculated by DFT method. According to the DFT calculations, the observed emission bandmore » of the compounds in solid state is due to electron transfer from an excited bptz-π* state (CBs) to the top of VBs. {sup 1}H NMR spectra of the compounds indicate that, in solution phase, the compounds don’t decompose completely. Thermal stability of the compounds is studied using TG, DTA methods. - Graphical abstract: Synthesis, crystal structure and emission spectra of [Hg(μ-bptz)X{sub 2}]{sub n} (X=Cl and Br) and [Hg{sub 2}(μ-bptz)(μ-I){sub 2}I{sub 2}]{sub n} are presented. The electronic band structure and linear optical properties of the compounds are calculated by the DFT method. - Highlights: • Three 1D Hg(II) halide coordination polymers with bptz ligand have been prepared. • The structures of the compounds are determined by single crystal XRD. • DFT calculations show that [Hg(μ-bptz)X{sub 2}]{sub n} (X=Cl and Br) have a direct band gap. • DFT calculations show that [Hg{sub 2}(μ-bptz)(μ-I){sub 2}I{sub 2}]{sub n} has an indirect band gap. • The compounds show an intraligand electron transfer emission band in solid state.« less

Chromomycin SA analogs from a marine-derived Streptomyces sp.

PubMed Central

Hu, Youcai; Espindola, Ana Paula D. M; Stewart, Nathan A.; Wei, Shuguang; Posner, Bruce A.; MacMillan, John B.

2011-01-01

Two chromomycin SA analogs, chromomycin SA3 and chromomycin SA2, along with deacetylchromomycin A3 and five previously reported chromomycin analogs were isolated from a marine-derived Streptomyces sp. The structures of the new compounds were determined by spectroscopic methods including 1D and 2D NMR techniques, HRMS and chemical methods. Chromomycin SA3 and chromomycin SA2 are the first naturally occuring chromomycin analogs with truncated side-chains. Biological evaluation of chromomycin analogs for cytotoxicity against two non-small cell lung cancer (NSCLC) cell-lines, A549 and HCC44, demonstrated a decrease in cytotoxicity for the truncated sides chain chromomycin analogs. PMID:21807523

Vibrational analysis of carbonyl modes in different stages of light-induced cyclopyrimidine dimer repair reactions

NASA Astrophysics Data System (ADS)

Schmitz, Matthias; Tavan, Paul; Nonella, Marco

2001-11-01

The formation of cyclopyrimidine dimers is a DNA defect, which is repaired by the enzyme DNA photolyase in a light-induced reaction. Radical anions of the dimers have been suggested to occur as short-lived intermediates during repair. For their identification time-resolved Fourier-transform infrared (FTIR) spectroscopy will be a method of choice. To support and guide such spectroscopic studies we have calculated the vibrational spectra of various pyrimidine compounds using density functional methods. Our results suggest that the carbonyl vibrations of these molecules can serve as marker modes to identify and distinguish intermediates of the repair reaction.

Molecular structure and spectroscopic characterization of Carbamazepine with experimental techniques and DFT quantum chemical calculations.

PubMed

Suhasini, M; Sailatha, E; Gunasekaran, S; Ramkumaar, G R

2015-04-15

A systematic vibrational spectroscopic assignment and analysis of Carbamazepine has been carried out by using FT-IR, FT-Raman and UV spectral data. The vibrational analysis were aided by electronic structure calculations - ab initio (RHF) and hybrid density functional methods (B3LYP) performed with standard basis set 6-31G(d,p). Molecular equilibrium geometries, electronic energies, natural bond order analysis, harmonic vibrational frequencies and IR intensities have been computed. A detailed interpretation of the vibrational spectra of the molecule has been made on the basis of the calculated Potential Energy Distribution (PED) by VEDA program. UV-visible spectrum of the compound was also recorded and the electronic properties, such as HOMO and LUMO energies and λmax were determined by HF/6-311++G(d,p) Time-Dependent method. The thermodynamic functions of the title molecule were also performed using the RHF and DFT methods. The restricted Hartree-Fock and density functional theory-based nuclear magnetic resonance (NMR) calculation procedure was also performed, and it was used for assigning the (13)C and (1)H NMR chemical shifts of Carbamazepine. Copyright © 2015 Elsevier B.V. All rights reserved.

Influence of different amino substituents in position 1 and 4 on spectroscopic and acid base properties of 9,10-anthraquinone moiety

NASA Astrophysics Data System (ADS)

Wcisło, Anna; Niedziałkowski, Paweł; Wnuk, Elżbieta; Zarzeczańska, Dorota; Ossowski, Tadeusz

2013-05-01

A series of novel 1-amino and 1,4-diamino-9,10-anthraquinones, substituted with different alkyl groups, were synthesized as the result of alkylation with amino substituents. All the obtained aminoanthraquinone derivatives were characterized by NMR, IR spectroscopy and mass spectrometry. The spectroscopic properties of these compounds were determined by using UV-Vis spectroscopy in acetonitrile, and in the mixture of acetonitrile and methanol at different pH ranges. The effects of various substituents present in the newly developed anthraquinone derivatives and their ability to form hydrogen bonds between the carbonyl oxygen atom of anthraquinone moiety and nitrogen atom of N-H group in 1-aminoanthraquinone (1-AAQ) and 1,4-diaminoanthraquinone (1,4-DAAQ) were studied. Additionally, the effects of hydrogen bond formation between O-H group in hydroxyethylamino substituent and the carbonyl oxygen atom of anthraquinone were investigated. The spectroscopic behavior of the studied derivatives strongly depended on the solvent-solute interactions and the nature of solvent. The values of pKa for the new anthraquinones were determined by the combined potentiometric and spectrophotometric titration methods.

Influence of different amino substituents in position 1 and 4 on spectroscopic and acid base properties of 9,10-anthraquinone moiety.

PubMed

Wcisło, Anna; Niedziałkowski, Paweł; Wnuk, Elżbieta; Zarzeczańska, Dorota; Ossowski, Tadeusz

2013-05-01

A series of novel 1-amino and 1,4-diamino-9,10-anthraquinones, substituted with different alkyl groups, were synthesized as the result of alkylation with amino substituents. All the obtained aminoanthraquinone derivatives were characterized by NMR, IR spectroscopy and mass spectrometry. The spectroscopic properties of these compounds were determined by using UV-Vis spectroscopy in acetonitrile, and in the mixture of acetonitrile and methanol at different pH ranges. The effects of various substituents present in the newly developed anthraquinone derivatives and their ability to form hydrogen bonds between the carbonyl oxygen atom of anthraquinone moiety and nitrogen atom of N-H group in 1-aminoanthraquinone (1-AAQ) and 1,4-diaminoanthraquinone (1,4-DAAQ) were studied. Additionally, the effects of hydrogen bond formation between O-H group in hydroxyethylamino substituent and the carbonyl oxygen atom of anthraquinone were investigated. The spectroscopic behavior of the studied derivatives strongly depended on the solvent-solute interactions and the nature of solvent. The values of pKa for the new anthraquinones were determined by the combined potentiometric and spectrophotometric titration methods. Copyright © 2013 Elsevier B.V. All rights reserved.

Spectroscopic analysis and molecular docking of imidazole derivatives and investigation of its reactive properties by DFT and molecular dynamics simulations

NASA Astrophysics Data System (ADS)

Thomas, Renjith; Hossain, Mossaraf; Mary, Y. Sheena; Resmi, K. S.; Armaković, Stevan; Armaković, Sanja J.; Nanda, Ashis Kumar; Ranjan, Vivek Kumar; Vijayakumar, G.; Van Alsenoy, C.

2018-04-01

Solvent-free synthesis pathway for obtaining two imidazole derivatives (2-chloro-1-(4-methoxyphenyl)-4,5-dimethyl-1H-imidazole (CLMPDI) and 1-(4-bromophenyl)-2-chloro-4,5-dimethyl-1H-imidazole (BPCLDI) has been reported in this work, followed by detailed experimental and computational spectroscopic characterization and reactivity study. Spectroscopic methods encompassed IR, FT-Raman and NMR techniques, with the mutual comparison of experimentally and computationally obtained results at DFT/B3LYP level of theory. Reactivity study based on DFT calculations encompassed molecular orbitals analysis, followed by calculations of molecular electrostatic potential (MEP) and average local ionization energy (ALIE) values, Fukui functions and bond dissociation energies (BDE). Additionally, the stability of title molecules in water has been investigated via molecular dynamics (MD) simulations, while interactivity with aspulvinonedimethylallyl transferase protein has been evaluated by molecular docking procedure. CLMPDI compound showed antimicrobial activity against all four bacterial strain in both gram positive and gram negative bacteria while, BPCLDI showed only in gram positive bacteria, Staphylococcus Aureus (MTCC1144). The first order hyperpolarizability of CLMPDI and BPCLDI are 20.15 and 6.10 times that of the standard NLO material urea.

Four new compounds from Imperata cylindrica.

PubMed

Liu, Xuan; Zhang, Bin-Feng; Yang, Li; Chou, Gui-Xin; Wang, Zheng-Tao

2014-04-01

Four new compounds, impecylone (1), deacetylimpecyloside (2), seguinoside K 4-methylether (3) and impecylenolide (4), were isolated from Imperata cylindrica along with two known compounds, impecyloside (5) and seguinoside K (6). Their structures were elucidated mainly by spectroscopic analyses including 1D- and 2D-NMR techniques, and the absolute configuration of 1 was confirmed by X-ray diffraction analysis. In calcium assay, the result indicated that compounds 1, 2, 4 and 5 cannot obviously inhibit the calcium peak value compared with the negative control, and suggested that the four compounds could not have anti-inflammatory activity.

Corrosion detection in steel-reinforced concrete using a spectroscopic technique

NASA Astrophysics Data System (ADS)

Garboczi, E. J.; Stutzman, P. E.; Wang, S.; Martys, N. S.; Hassan, A. M.; Duthinh, D.; Provenzano, V.; Chou, S. G.; Plusquellic, D. F.; Surek, J. T.; Kim, S.; McMichael, R. D.; Stiles, M. D.

2014-02-01

Detecting the early corrosion of steel that is embedded in reinforced concrete (rebar) is a goal that would greatly facilitate the inspection and measurement of corrosion in the US physical infrastructure. Since 2010, the National Institute of Standards and Technology (NIST) has been working on a large project to develop an electromagnetic (EM) probe that detects the specific corrosion products via spectroscopic means. Several principal iron corrosion products, such as hematite and goethite, are antiferromagnetic at field temperatures. At a given applied EM frequency, which depends on temperature, these compounds undergo a unique absorption resonance that identifies the presence of these particular iron corrosion products. The frequency of the resonances tends to be on the order of 100 GHz or higher, so transmitting EM waves through the cover concrete and back out again at a detectable level has been challenging. NIST has successfully detected these two iron corrosion products, and is developing equipment and methodologies that will be capable of penetrating the typical 50 mm of cover concrete in the field. The novel part of this project is the detection of specific compounds, rather than only geometrical changes in rebar cross-section. This method has the potential of providing an early-corrosion probe for steel in reinforced concrete, and for other applications where steel is covered by various layers and coatings.

[Chemical Constituents from Mallotus paniculatus (II)].

PubMed

Zhu, Chun-ling

2015-04-01

To study the chemical constituents of Mallotus paniculaus radix. The compounds were isolated with column chromatography. The chemical structures were identified by spectral and spectroscopic technology. Seven compounds were isolated from the n-BuOH extract and identified as scopoletin(1), isoscopletin(2), erythordiol(3), apigenin(4), 4-methoxybenzoic acid(5), acetylaleuritolic acid(6) and β-daucosterol (7). compounds 2 - 6 are isolated from this plant for the first time.

Instant detection and identification of concealed explosive-related compounds: Induced Stokes Raman versus infrared.

PubMed

Elbasuney, Sherif; El-Sherif, Ashraf F

2017-01-01

The instant detection of explosives and explosive-related compounds has become an urgent priority in recent years for homeland security and counter-terrorism applications. Modern techniques should offer enhancement in selectivity, sensitivity, and standoff distances. Miniaturisation, portability, and field-ruggedisation are crucial requirements. This study reports on instant and standoff identification of concealed explosive-related compounds using customized Raman technique. Stokes Raman spectra of common explosive-related compounds were generated and spectrally resolved to create characteristic finger print spectra. The scattered Raman emissions over the band 400:2000cm -1 were compared to infrared absorption using FTIR. It has been demonstrated that the two vibrational spectroscopic techniques were opposite and completing each other. Molecular vibrations with strong absorption in infrared (those involve strong change in dipole moments) induced weak signals in Raman and vice versa. The tailored Raman offered instant detection, high sensitivity, and standoff detection capabilities. Raman demonstrated characteristic fingerprint spectra with stable baseline and sharp intense peaks. Complete correlations of absorption/scattered signals to certain molecular vibrations were conducted to generate an entire spectroscopic profile of explosive-related compounds. This manuscript shades the light on Raman as one of the prevailing technologies for instantaneous detection of explosive-related compounds. Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.

Two new stemphol sulfates from the mangrove endophytic fungus Stemphylium sp. 33231.

PubMed

Zhou, Xue-Ming; Zheng, Cai-Juan; Chen, Guang-Ying; Song, Xiao-Ping; Han, Chang-Ri; Tang, Xiong-Zhao; Liu, Rui-Jie; Ren, Li-Lian

2015-08-01

Two new stemphol sulfates, stemphol A (1) and stemphol B (2), along with known compound stemphol (3) were isolated from the EtOAc extract of the fermentation of an endophytic Stemphylium sp. 33231. The structures of these compounds were elucidated on the basis of spectroscopic analysis. The isolated compounds exhibited potent antibacterial activities against six terrestrial pathogenic bacteria with MIC values of 0.6-10 μg ml(-1). The inhibitory activities of all compounds against five cancer cell lines were evaluated.

Hepatoprotective triterpenoids and lignans from the stems of Schisandra pubescens.

PubMed

Wang, Guo-Wei; Deng, Li-Qing; Luo, You-Ping; Liao, Zhi-Hua; Chen, Min

2017-08-01

One new triterpenoid (1) and 13 known compounds (2-14) were isolated from Schisandra pubescens stems. The structure of the new compound was established on the basis of 1D/2D NMR and HRESIMS spectroscopic analyses. The isolated compounds were evaluated for their hepatoprotective activities against D-GalN-induced cell injury in QSG7701 cells. Compounds 1, 13 and 14 at 10 μM showed hepatoprotective activities, with survival rates of 60.5, 50.4 and 48.9%, respectively.

An Unusual Diterpene-Enhygromic Acid and Deoxyenhygrolides from a Marine Myxobacterium, Enhygromyxa sp.

PubMed

Tomura, Tomohiko; Nagashima, Shiori; Yamazaki, Satoshi; Iizuka, Takashi; Fudou, Ryosuke; Ojika, Makoto

2017-04-06

Three new compounds, enhygromic acid ( 1 ) and deoxyenhygrolides A ( 2 ) and B ( 3 ), were isolated from a marine myxobacterium, Enhygromyxa sp. Compound 1 was found to be an acrylic acid derivative with a rare polycyclic carbon skeleton, decahydroacenaphthylene, by spectroscopic analyses. Compounds 2 and 3 were deoxy analogs of the known γ-alkylidenebutenolides, enhygrolides. Compound 1 exhibited cytotoxicity against B16 melanoma cells and anti-bacterial activity against Bacillus subtilis , and enhanced the NGF-induced neurite outgrowth of PC12 cells.

Spectroscopic detection of pharmaceutical compounds from an aflatoxigenic strain of Aspergillus parasiticus.

PubMed

Basaran, P; Demirbas, R M

2010-08-20

Polar and non-polar secondary metabolites as well as phenolic compounds of Aspergillus parasiticus grown on hazelnut were analyzed by high-resolution high performance liquid chromatography-mass spectroscopy and fourier transform infrared spectroscopy. Several novel and beneficial compounds such as dibutyl phthalate, pyrogallol, fumagillol, italicic acid and sorbicillin were identified from A. parasiticus for the first time. Some of these compounds have the potential to be used in pharmaceutical industry. Copyright 2009 Elsevier GmbH. All rights reserved.

Spectroscopic studies of the intramolecular hydrogen bonding in o-hydroxy Schiff bases, derived from diaminomaleonitrile, and their deprotonation reaction products

NASA Astrophysics Data System (ADS)

Szady-Chełmieniecka, Anna; Kołodziej, Beata; Morawiak, Maja; Kamieński, Bohdan; Schilf, Wojciech

2018-01-01

The structural study of five Schiff bases derived from diaminomaleonitrile (DAMN) and 2-hydroxy carbonyl compounds was performed using 1H, 13C and 15N NMR methods in solution and in the solid state as well. ATR-FTIR and X-Ray spectroscopies were used for confirmation of the results obtained by NMR method. The imine obtained from DAMN and benzaldehyde was synthesized as a model compound which lacks intramolecular hydrogen bond. Deprotonation of all synthesized compounds was done by treating with tetramethylguanidine (TMG). NMR data revealed that salicylidene Schiff bases in DMSO solution exist as OH forms without intramolecular hydrogen bonds and independent on the substituents in aromatic ring. In the case of 2-hydroxy naphthyl derivative, the OH proton is engaged into weak intramolecular hydrogen bond. Two of imines (salDAMN and 5-BrsalDAMN) exist in DMSO solution as equilibrium mixtures of two isomers (A and B). The structures of equilibrium mixture in the solid state have been studied by NMR, ATR-FTIR and X-Ray methods. The deprotonation of three studied compounds (salDAMN, 5-BrsalDAMN, and 5-CH3salDAMN) proceeded in two different ways: deprotonation of oxygen atom (X form) or of nitrogen atom of free primary amine group of DAMN moiety (Y form). For 5-NO2salDAMN and naphDAMN only one form (X) was observed.

Dihydroberkleasmin A: a new eremophilane sesquiterpenoid from the fermentation broth of the plant endophytic fungus Pestalotiopsis photiniae.

PubMed

Yang, Xiao-Long; Zhang, Su; Zhu, Hua-Jie; Luo, Du-Qiang

2011-02-23

Dihydroberkleasmin A (1), a new ester-substituted sesquiterpenoid related to the eremophilane class, together with the known compound berkleasmin C (2), were isolated from the fermentation broth of the plant endophytic fungus Pestalotiopsis photiniae. The structure of dihydroberkleasmin A (1) was elucidated by extensive spectroscopic analysis. The stereochemistry was assigned by comparison of the NMR spectroscopic data with those of berkleasmin A.

Using terahertz time-domain spectroscopical technique to monitor cocrystal formation between piracetam and 2,5-dihydroxybenzoic acid

NASA Astrophysics Data System (ADS)

Du, Yong; Xia, Yi; Zhang, Huili; Hong, Zhi

2013-07-01

Far-infrared vibrational absorption of cocrystal formation between 2,5-dihydroxybenzoic acid (2,5-DHBA) and piracetam compounds under solvent evaporation and grinding methods have been investigated using terahertz time-domain spectroscopy (THz-TDS) at room temperature. The experimental results show large difference among absorption spectra of the formed cocrystals and the involved individual parent molecules in 0.20-1.50 THz region, which probably originated from the intra-molecular and inter-molecular hydrogen bonds due to the presence of two hydroxyl groups in 2,5-DHBA and amide moieties in piracetam compound. The THz absorption spectra of two formed cocrystals with different methods are almost identical. With grinding method, the reaction process can be monitored directly from both time-domain and frequency-domain spectra using THz-TDS technique. The results indicate that THz-TDS technology can absolutely offer us a high potential method to identify and characterize the formed cocrystals, and also provide the rich information about their reaction dynamic process involving two or more molecular crystals in situ to better know the corresponding reaction mechanism in pharmaceutical fields.

Electrochemical and spectroscopic characteristics of p-acryloyloxybenzoyl chloride and p-acryloyloxybenzoic acid and antimicrobial activity of organic compounds

NASA Astrophysics Data System (ADS)

Cakir, I.; Soykan, U.; Cetin, S.; Karaboga, F.; Zalaoglu, Y.; Dogruer, M.; Terzioglu, C.; Yildirim, G.

2014-11-01

The purpose of this multidisciplinary work is to characterize title compounds, p-acryloyloxybenzoyl chloride (ABC) and p-acryloyloxybenzoic acid (ABA) by means of experimental and theoretical evidences. As experimental research, Fourier transformation-infrared spectra (in the region 400-4000 cm-1) and nuclear magnetic resonance (NMR) chemical shifts (with a frequency of 400 MHz) are examined for spectroscopic properties belonging to the new synthesized compounds. Moreover, the compounds are investigated for antimicrobial activity against various microorganisms (Gram-positive and Gram-negative) by means of the visual inhibition zone technique on the agar media. The experimental results observed indicate that ABA exhibits more powerful inhibitors of microorganisms due to the presence of the hydroxyl group leading to higher reactive system, one of the most striking features of the paper. As for the theoretical studies, the optimized molecular structures, vibrational frequencies, corresponding vibrational spectra interpreted with the aid of normal coordinate analysis based on scaled density functional force field, atomic charges, thermodynamic properties at different temperature, 1H NMR chemical shifts by way of density functional theory (DFT) with the standard (B3LYP) methods at 6-311G++(d,p) basis set combination for the first time. According to findings, the 1H NMR chemical shifts and vibrational frequencies are obtained to be in good agreement with the suitable experimental results. Thus, it would be more precise to say that the calculation level chosen is powerful approach for understanding in the identification of the molecules investigated. At the same time, we determine the electrochemical characteristics belonging to the samples via the simulation of translation energy (HOMO-LUMO), molecular electrostatic potential (MEP) and electrostatic potential (ESP) investigations. It is observed that the strong intra-molecular charge transfer (ICT) appears between the donor and acceptor in the both compounds (especially ABA) due to the existence of the strong electronic donating groups and effective π-π* conjugated segments with high electronic donor ability for the electrophilic attack (intermolecular interactions).

Database for Rapid Dereplication of Known Natural Products Using Data from MS and Fast NMR Experiments.

PubMed

Zani, Carlos L; Carroll, Anthony R

2017-06-23

The discovery of novel and/or new bioactive natural products from biota sources is often confounded by the reisolation of known natural products. Dereplication strategies that involve the analysis of NMR and MS spectroscopic data to infer structural features present in purified natural products in combination with database searches of these substructures provide an efficient method to rapidly identify known natural products. Unfortunately this strategy has been hampered by the lack of publically available and comprehensive natural product databases and open source cheminformatics tools. A new platform, DEREP-NP, has been developed to help solve this problem. DEREP-NP uses the open source cheminformatics program DataWarrior to generate a database containing counts of 65 structural fragments present in 229 358 natural product structures derived from plants, animals, and microorganisms, published before 2013 and freely available in the nonproprietary Universal Natural Products Database (UNPD). By counting the number of times one or more of these structural features occurs in an unknown compound, as deduced from the analysis of its NMR ( 1 H, HSQC, and/or HMBC) and/or MS data, matching structures carrying the same numeric combination of searched structural features can be retrieved from the database. Confirmation that the matching structure is the same compound can then be verified through literature comparison of spectroscopic data. This methodology can be applied to both purified natural products and fractions containing a small number of individual compounds that are often generated as screening libraries. The utility of DEREP-NP has been verified through the analysis of spectra derived from compounds (and fractions containing two or three compounds) isolated from plant, marine invertebrate, and fungal sources. DEREP-NP is freely available at https://github.com/clzani/DEREP-NP and will help to streamline the natural product discovery process.

Manoalide-related Sesterterpene from the Marine Sponge Luffariella variabilis.

PubMed

Hamada, Toshiyuki; Harada, Daisuke; Hirata, Mitsunobu; Yamashita, Keisuke; Palaniveloo, Kishneth; Okamura, Hiroaki; Iwagawa, Tetsuo; Arima, Naomichi; Iriguchi, Toshiyuki; de Voogd, Nicole J; Vairappan, Charles S

2015-06-01

A new manoalide-related sesterterpene, (4E,6E)-dehydro-25-O-methylmanoalide (1), was isolated from the organic extracts of the Bornean marine sponge Luffariella variabilis, together with the known compound (4E,6E)-dehydromanoalide (2). The structure of compound 1 was elucidated by interpretation of its spectroscopic data.

Furylhydroquinones and miscellaneous compounds from the roots of Lithospermum erythrorhizon and their anti-inflammatory effect in HaCaT cells.

PubMed

Ahn, Jongmin; Chae, Hee-Sung; Chin, Young-Won; Kim, Jinwoong

2018-01-31

One new furylhydroquinone derivative (1) and seven known compounds (2-8) were isolated from the roots of Lithospermum erythrorhizon Sieb. et Zucc (Boraginaceae). The structure of 1 was elucidated by extensive spectroscopic methods using NMR and MS. The absolute configuration of shikonofuran J (1) was unambiguously determined by aid of comparison experimental ECD with predicted ECD spectra. All the isolates were tested for their inhibitory activities against IL-6 production in HaCaT cells stimulated by tumor necrosis factor (TNF)-α. It was found that gracicleistanthoside (5) and uridine (7) remarkably down-regulated the TNF-α-induced synthesis of interleukin-6 (IL-6), a pro-inflammatory cytokine associated with cutaneous inflammation, in HaCaT cells.

Experimental and theoretical calculation studies on the structure elucidation and absolute configuration of calyxins from Alpinia katsumadai.

PubMed

Wang, Xiao-Bing; Yang, Chang-Shui; Luo, Jian-Guang; Zhang, Chao; Luo, Jun; Yang, Ming-Hua; Kong, Ling-Yi

2017-06-01

Six novel calyxins, named calyxin T-W, ent-calyxin T and ent-calyxin U were isolated from the seeds of Alpinia katsumadai Hayata. Their relative configurations were elucidated by means of detailed UV, IR, NMR and MS spectroscopic data. Their absolute configurations were assigned by collaborative studies on single crystal X-ray diffraction analysis, Mosher's method, electronic circular dichroism (ECD), optical rotation and theoretical calculations. These compounds are Friedel-Cranft alkylation adducts composed of coexisted diarylheptanoids and flavanone from the seeds of Alpinia katsumadai. The antiproliferative activity of the six compounds against NCI-H460, HeLa, SMMC-7721 and HCT-116 cell lines was also reported, and most of them showed moderate to strong activities. Copyright © 2017. Published by Elsevier B.V.

Spectroscopic and structural studies of a new para-iodo-N-benzyl amide of salinomycin

NASA Astrophysics Data System (ADS)

Antoszczak, Michał; Janczak, Jan; Rutkowski, Jacek; Brzezinski, Bogumił; Huczyński, Adam

2017-11-01

A new para-iodo-N-benzyl amide of salinomycin was synthesized and characterized by NMR, FT-IR, DFT, single crystal X-ray diffraction and theoretical methods. The results obtained for the crystal, in solution and in gas phase provided evidence of pseudo-cyclic structure of this compound stabilized by intramolecular hydrogen bonds. It was shown that the compound studied forms stable 1:1 complexes with monovalent (Li+, Na+, K+, Rb+ and Cs+) and divalent (Mg2+, Ca2+, Sr2+ and Ba2+) cations demonstrating that the chemical modification of salinomycin carboxyl group considerably changes the ionophoretic properties of this antibiotic. For the first time, the ESI MS fragmentations of the complex of para-iodo-N-benzyl amide of salinomycin with Na+ are also discussed in details.

Sesquiterpenoids and lignans from the roots of Valeriana officinalis L.

PubMed

Wang, Peng-Cheng; Ran, Xin-Hui; Chen, Rui; Luo, Huai-Rong; Ma, Qing-Yun; Liu, Yu-Qing; Hu, Jiang-Miao; Huang, Sheng-Zhuo; Jiang, He-Zhong; Chen, Zhong-Quan; Zhou, Jun; Zhao, You-Xing

2011-10-01

Two new guaiane-type sesquiterpenoids, valerol A (1) and kessyl 3-acetate (2), together with nine known compounds, valeracetate (3), anismol A (4), orientalol C (5), spatulenol (6), 4α,10α-epoxyaromadendrane (7), (+)-8-hydroxypinoresinol (8), pinorespiol (9), pinoresinol 4-O-β-D-glucopyranoside (10), and 8-hydroxypinoresinol 4'-O-β-D-glucopyranoside (11) were isolated from the roots of Valeriana officinalis. The structures and relative configurations of 1 and 2 were elucidated on the basis of spectroscopic methods (1D- and 2D-NMR, MS, UV, and IR). These compounds were evaluated for inhibitory activity on acetylcholinesterase (AChE) and enhancing activity on nerve growth factor (NGF)-mediated neurite outgrowth in PC12 cells. Copyright © 2011 Verlag Helvetica Chimica Acta AG, Zürich.

Studies on chemical constituents of Gracilaria verrucosa.

PubMed

Aydoğmuş, Zeynep; Topcu, Gülaçti; Güven, Kasim Cemal

2008-12-01

A new sterol glucoside, (24R)-5 alpha-stigmast-9-(11)-en-3beta-D-glucopyranoside (1) has been isolated from a methanol extract of the red alga Gracilaria verrucosa, while cholesterol and (Z)-9-hexadecenoic acid (palmitoleic acid) have been isolated from a dichloromethane-acetone extract of the same alga. Additionally, an oily fraction of a dichloromethane-acetone extract has been investigated by gas chromatography/mass spectrometry (GC/MS). The main components in the oily fraction were heneicosanoic acid (49.8%), (Z)-9-octadecenoic acid (15.8%), and 15-tetracosenoic acid (15.6%) in addition to a few hydrocarbons, simple aromatics and a new compound, namely 3,4-dimethyl-5-carboxyclic acid-1-oxacyclopent-3-en-2-one. The structures of the isolated compounds have been elucidated by spectroscopic methods.

Cytotoxic Withanolide Constituents of Physalis longifolia

PubMed Central

Zhang, Huaping; Samadi, Abbas K.; Gallagher, Robert J.; Araya, Juan J.; Tong, Xiaoqin; Day, Victor W.; Cohen, Mark S.; Kindscher, Kelly; Gollapudi, Rao; Timmermann, Barbara N.

2011-01-01

Fourteen new withanolides 1-14, named withalongolides A-N, respectively, were isolated from the aerial parts of Physalis longifolia together with eight known compounds (15-22). The structures of compounds 1-14 were elucidated through spectroscopic techniques and chemical methods. In addition, the structures of withanolides 1, 2, 3, and 6 were confirmed by X-ray crystallographic analysis. Using a MTS viability assays, eight withanolides (1, 2, 3, 7, 8, 15, 16, and 19) and four acetylated derivatives (1a, 1b, 2a, and 2b) showed potent cytotoxicity against human head and neck squamous cell carcinoma (JMAR and MDA-1986), melanoma (B16F10 and SKMEL-28), and normal fetal fibroblast (MRC-5) cells with IC50 values in the range between 0.067 and 9.3 μM. PMID:22098611

The spectroscopic (FT-IR, FT-Raman, UV) and first order hyperpolarizability, HOMO and LUMO analysis of 3-aminobenzophenone by density functional method

NASA Astrophysics Data System (ADS)

Karabacak, M.; Kurt, M.; Cinar, M.; Ayyappan, S.; Sudha, S.; Sundaraganesan, N.

In this work, experimental and theoretical study on the molecular structure and the vibrational spectra of 3-aminobenzophenone (3-ABP) is presented. The vibrational frequencies of the title compound were obtained theoretically by DFT/B3LYP calculations employing the standard 6-311++G(d,p) basis set for optimized geometry and were compared with Fourier transform infrared spectrum (FTIR) in the region of 400-4000 cm-1 and with Fourier Transform Raman spectrum in the region of 50-4000 cm-1. Complete vibrational assignments, analysis and correlation of the fundamental modes for the title compound were carried out. The vibrational harmonic frequencies were scaled using scale factor, yielding a good agreement between the experimentally recorded and the theoretically calculated values.

Alteration of fluorescent protein spectroscopic properties upon cryoprotection.

PubMed

von Stetten, David; Batot, Gaëlle O; Noirclerc-Savoye, Marjolaine; Royant, Antoine

2012-11-01

Cryoprotection of a protein crystal by addition of small-molecule compounds may sometimes affect the structure of its active site. The spectroscopic and structural effects of the two cryoprotectants glycerol and ethylene glycol on the cyan fluorescent protein Cerulean were investigated. While glycerol had almost no noticeable effect, ethylene glycol was shown to induce a systematic red shift of the UV-vis absorption and fluorescence emission spectra. Additionally, ethylene glycol molecules were shown to enter the core of the protein, with one of them binding in close vicinity to the chromophore, which provides a sound explanation for the observed spectroscopic changes. These results highlight the need to systematically record spectroscopic data on crystals of light-absorbing proteins and reinforce the notion that fluorescent proteins must not been seen as rigid structures.

IR spectroscopic study of Pt-containing zeolites in the hydrodechlorination reaction of C 2 chlorinated hydrocarbons

NASA Astrophysics Data System (ADS)

Hannus, I.; Kropok, Zs.; Halász, J.

2007-05-01

Some of the chlorinated organic compounds are widely used commercially, because of their advantageous chemical/physical properties or having toxicity for pestiferous living substances. However, emitted into the atmosphere they are responsible for diminishing the ozone layer in the stratosphere. Therefore, a lot of effort is devoted in finding proper solutions to decompose these chemicals in environmentally friendly ways. Platinum on different carriers play very important role in catalytic hydrodechlorination of these compounds. We have found that Pt-containing Y-FAU zeolite is an active catalyst in the hydrodechlorination of trichloroethene. IR spectroscopic experiments showed that the final products are ethane and HCl, and the hydrogen/reactant ratio exerts large influence on the rate of the hydrodechlorination reaction.

Bio-important antipyrine derived Schiff bases and their transition metal complexes: Synthesis, spectroscopic characterization, antimicrobial, anthelmintic and DNA cleavage investigation

NASA Astrophysics Data System (ADS)

Manjunath, M.; Kulkarni, Ajaykumar D.; Bagihalli, Gangadhar B.; Malladi, Shridhar; Patil, Sangamesh A.

2017-01-01

Spectroscopic (IR, NMR, UV-vis, ESR, ESI-mass), magnetic and TGA studies suggests octahedral geometry for all the CoII, NiII and CuII complexes of the Schiff bases, derived from 4-aminoantipyrine and 8-formyl-7-Hydroxy-4-methylcoumarin/5-formyl-6-hydroxycoumarin, coordinated through ONO donor sites. Antibacterial (Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella typhi), antifungal (Aspergillus niger, Aspergillus flavus and Cladosporium) and DNA cleavage properties of the metal complexes are investigated. The results suggested that some of the synthesized compounds are potential antimicrobials. The synthesized compounds tested for their anthelmintic activities and it was found that CoII and NiII complexes exhibited good anthelmintic properties.

Synthesis of four diastereomers of sclerophytin F and structural reassignment of several sclerophytin natural products.

PubMed

Clark, J Stephen; Delion, Laëtitia; Farrugia, Louis J

2015-03-16

Synthesis of the triol that has been proposed to be the marine natural product sclerophytin F has been completed along with the syntheses of three diastereomers. Comparison of the NMR spectroscopic data for all four compounds to the data reported for the natural product reveals that sclerophytin F is not the 3S diastereomer of sclerophytin A as proposed by Friedrich and Paquette. Re-analysis of the NMR spectroscopic data for known sclerophytin natural products and synthetic analogues leads to the conclusion that sclerophytins E and F are the same compound. This finding has allowed structural reassignment of several other cladiellin natural products. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Two novel macroacyclic schiff bases containing bis-N 2O 2 donor set and their binuclear complexes: synthesis, spectroscopic and magnetic properties

NASA Astrophysics Data System (ADS)

Karaoglu, Kaan; Baran, Talat; Serbest, Kerim; Er, Mustafa; Degirmencioglu, Ismail

2009-03-01

Herein, we report two novel macroacyclic Schiff bases derived from tetranaphthaldehyde derivative compound and their binuclear Mn(II), Ni(II), Cu(II) and Zn(II) complexes. The structures of the compounds have been proposed by elemental analyses, spectroscopic data i.e. IR, 1H and 13C NMR, UV-Vis, electrospray ionisation mass spectra, molar conductivities and magnetic susceptibility measurements. The stoichiometries of the complexes derived from mass and elemental analysis correspond to the general formula [M 2L(ClO 4) n](ClO 4) 4-n, (where M is Mn(II), Ni(II), Cu(II), Zn(II) and L represents the Schiff base ligands).

Antimalarial activity of sesquiterpene lactones from Vernonia cinerea.

PubMed

Chea, Aun; Hout, Sotheara; Long, Christophe; Marcourt, Laurence; Faure, Robert; Azas, Nadine; Elias, Riad

2006-10-01

Two new sesquiterpene lactones, vernolides C and D as well as six known ones were isolated from the dichloromethane fraction of an aqueous extract from Vernonia cinerea. Their structures were elucidated by spectroscopic methods. Among the known sesquiterpene lactones, three of them were described in this plant for the first time. In vitro antiplasmodial evaluation showed that the three major compounds 1, 7 and 8 were active against chloroquine resistant Plasmodium falciparum strain (W2) with IC(50) 3.9, 3.7 and 3.5 microM, respectively.

A new labdane diterpene from the rhizomes of Alpinia officinarum.

PubMed

Zou, Qiong-Yu; Wu, Hai-Feng; Tang, Yu-Lian; Chen, Di-Zhao

2016-01-01

A new labdane diterpene, (Z)-12,14-labdadien-15(16)-olide-17-oic acid (1), and a new natural cadinane sesquiterpene, 4-isopropyl-6-methyl-1-naphthalenemethanol (2), were isolated from the ethanolic extract of the rhizomes of Alpinia officinarum, together with three other products, galangin (3), kaempferol (4) and quercetin (5). Their structures were elucidated by using extensive spectroscopic methods. Compounds 1 and 2 showed no remarkable cytotoxic activity against HeLa and HepG2 cancer cell lines with IC50>50 μg mL(- 1).

New Anti-Inflammatory Cembranes from the Cultured Soft Coral Nephthea columnaris

PubMed Central

Hsiao, Ting-Hsi; Sung, Chun-Sung; Lan, Yu-Hsuan; Wang, Yi-Chen; Lu, Mei-Chin; Wen, Zhi-Hong; Wu, Yang-Chang; Sung, Ping-Jyun

2015-01-01

Two new cembranes, columnariols A (1) and B (2), were isolated from the cultured soft coral Nephthea columnaris. The structures of cembranes 1 and 2 were elucidated by spectroscopic methods. In the anti-inflammatory effects test, cembranes 1 and 2 were found to significantly inhibit the accumulation of the pro-inflammatory iNOS and COX-2 protein of the lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. Compound 1 exhibited moderate cytotoxicity toward LNCaP cells with an IC50 value of 9.80 μg/mL. PMID:26035022

Discovery of New Eunicellins from an Indonesian Octocoral Cladiella sp.

PubMed Central

Chen, Yung-Husan; Tai, Chia-Ying; Su, Yin-Di; Chang, Yu-Chia; Lu, Mei-Chin; Weng, Ching-Feng; Su, Jui-Hsin; Hwang, Tsong-Long; Wu, Yang-Chang; Sung, Ping-Jyun

2011-01-01

Two new 11-hydroxyeunicellin diterpenoids, cladieunicellin F (1) and (–)-solenopodin C (2), were isolated from an Indonesian octocoral Cladiella sp. The structures of eunicellins 1 and 2 were established by spectroscopic methods, and eunicellin 2 was found to be an enantiomer of the known eunicellin solenopodin C (3). Eunicellin 2 displayed inhibitory effects on the generation of superoxide anion and the release of elastase by human neutrophils. The previously reported structures of two eunicellin-based compounds, cladielloides A and B, are corrected in this study. PMID:21747739

Aporphine alkaloids and feruloylamides from the bark of Xylopia benthamii R.E. Fries (Annonaceae).

PubMed

Pimenta, L P S; Mendonça, D D

2012-01-01

The bark of Xylopia benthamii R.E. Fries was investigated in a search for new bioactive compounds. The ethanolic extract of the air-dried bark of X. benthamii was obtained and submitted to an acidic extraction procedure to obtain an alkaloid mixture. Chromatographic fractionation led to the isolation of two aporphine alkaloids, nornantenine and laurotetanine, and a mixture of trans- and cis-feruloyltyramine, isolated for the first time in this genus. Structures were established by spectroscopic methods as NMR (1D and 2D) and mass spectrometry (ESI-MS).

New isoflavone glycosides from the stems of Dalbergia vietnamensis.

PubMed

Loan, Pham Thanh; Le Anh, Hoang Tuan; Cuc, Nguyen Thi; Yen, Duong Thi Hai; Hang, Dan Thi Thuy; Ha, Tran Minh; Nhiem, Nguyen Xuan; Van Du, Nguyen; Thai, Tran Huy; Van Minh, Chau; Van Kiem, Phan

2014-06-01

Two new isoflavone glycosides, dalspinosin 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (1) and caviunin 7-O-(5-O-trans-p-coumaroyl)-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (2), and two known compounds, caviunin 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (3) and caviunin (4) were isolated from the stems of Dalbergia vietnamensis. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D- and 2D-NMR spectroscopy, as well as by comparing with the NMR data reported in the literature.

Antioxidant farnesylated hydroquinones from Ganoderma capense.

PubMed

Peng, Xingrong; Li, Lei; Wang, Xia; Zhu, Guolei; Li, Zhongrong; Qiu, Minghua

2016-06-01

Phytochemical investigation of the fruiting bodies of Ganoderma capense led to isolation of eight aromatic meroterpenoids (1-8). Ganocapensins A and B (1, 2) possessed a thirteen-membered and a fourteen-membered ether rings, respectively. The structures of new isolates including absolute configuration were elucidated on the basis of extensive spectroscopic technologies and Mosher's method. All isolated compounds showed significant antioxidant effects with IC50 values ranging from 6.00±0.11 to 8.20±0.30μg/ml in the DPPH radical scavenging assay. Copyright © 2016 Elsevier B.V. All rights reserved.

Polycyclic phloroglucinols as PTP1B inhibitors from Hypericum longistylum: Structures, PTP1B inhibitory activities, and interactions with PTP1B.

PubMed

Cao, Xiangrong; Yang, Xueyuan; Wang, Peixia; Liang, Yue; Liu, Feng; Tuerhong, Muhetaer; Jin, Da-Qing; Xu, Jing; Lee, Dongho; Ohizumi, Yasushi; Guo, Yuanqiang

2017-12-01

Protein tyrosine phosphatase 1B (PTP1B) has been regarded asa target for the research and development of new drugs to treat type II diabetes and PTP1B inhibitors are potential lead compounds for this type of new drugs. A phytochemical investigation to obtain new PTP1B inhibitors resulted in the isolation of four new phloroglucinols, longistyliones A-D (1-4) from the aerial parts of Hypericum longistylum. The structures of 1-4 were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analysis, and the absolute configurations of these compounds were established by comparing their experimental electronic circular dichroism (ECD) spectra with those calculated by the time-dependent density functional theory method. Compounds 1-4 possess a rare polycyclic phloroglucinol skeleton. The following biological evaluation revealed that all of the compounds showed PTP1B inhibitory effects. The further molecular docking studies indicated the strong interactions between these bioactive compounds with the PTP1B protein, which revealed the possible mechanism of PTP1B inhibition of bioactive compounds. All of the results implied that these compounds are potentially useful for the treatment of type II diabetes. Copyright © 2017 Elsevier Inc. All rights reserved.

Crystal structure, stability and spectroscopic properties of methane and CO2 hydrates.

PubMed

Martos-Villa, Ruben; Francisco-Márquez, Misaela; Mata, M Pilar; Sainz-Díaz, C Ignacio

2013-07-01

Methane hydrates are highly present in sea-floors and in other planets and their moons. Hence, these compounds are of great interest for environment, global climate change, energy resources, and Cosmochemistry. The knowledge of stability and physical-chemical properties of methane hydrate crystal structure is important for evaluating some new green becoming technologies such as, strategies to produce natural gas from marine methane hydrates and simultaneously store CO2 as hydrates. However, some aspects related with their stability, spectroscopic and other chemical-physical properties of both hydrates are not well understood yet. The structure and stability of crystal structure of methane and CO2 hydrates have been investigated by means of calculations with empirical interatomic potentials and quantum-mechanical methods based on Hartree-Fock and Density Functional Theory (DFT) approximations. Molecular Dynamic simulations have been also performed exploring different configurations reproducing the experimental crystallographic properties. Spectroscopic properties have also been studied. Frequency shifts of the main vibration modes were observed upon the formation of these hydrates, confirming that vibration stretching peaks of C-H at 2915cm(-1) and 2905cm(-1) are due to methane in small and large cages, respectively. Similar effect is observed in the CO2 clathrates. The guest-host binding energy in these clathrates calculated with different methods are compared and discussed in terms of adequacy of empirical potentials and DFT methods for describing the interactions between gas guest and the host water cage, proving an exothermic nature of methane and CO2 hydrates formation process. Copyright © 2013 Elsevier Inc. All rights reserved.

Isolation and Quantification of Ginsenoside Rh23, a New Anti-Melanogenic Compound from the Leaves of Panax ginseng.

PubMed

Lee, Dae Young; Kim, Hyoung-Geun; Lee, Yeong-Geun; Kim, Jin Hee; Lee, Jae Won; Choi, Bo-Ram; Jang, In-Bae; Kim, Geum-Soog; Baek, Nam-In

2018-01-29

A new ginsenoside, named ginsenoside Rh23 ( 1 ), and 20- O -β-d-glucopyranosyl-3β,6α,12β,20β,25-pentahydroxydammar-23-ene ( 2 ) were isolated from the leaves of hydroponic Panax ginseng . Compounds were isolated by various column chromatography and their structures were determined based on spectroscopic methods, including high resolution quadrupole/time of flight mass spectrometry (HR-QTOF/MS), nuclear magnetic resonance (NMR) spectroscopy, and infrared (IR) spectroscopy. To determine anti-melanogenic activity, the change in the melanin content in melan-a cells treated with identified compounds was tested. Additionally, we investigated the melanin inhibitory effects of ginsenoside Rh23 on pigmentation in a zebrafish in vivo model. Compound 1 inhibited potent melanogenesis in melan-a cells with 37.0% melanogenesis inhibition at 80 µM and also presented inhibition on the body pigmentation in zebrafish model. Although compound 2 showed slightly lower inhibitory activity than compound 1 , it also showed significantly decreased melanogenesis in melan-a cell and in zebrafish model. These results indicated that compounds isolated from hydroponic P. ginseng may be used as new skin whitening compound through the in vitro and in vivo systems. Furthermore, this study demonstrated the utility of MS-based compound 1 for the quantitative analysis. Ginsenoside Rh23 ( 1 ) was found at a level of 0.31 mg/g in leaves of hydroponic P. ginseng .

Analgesic principle from Curcuma amada.

PubMed

Faiz Hossain, Chowdhury; Al-Amin, Mohammad; Rahman, Kazi Md Mahabubur; Sarker, Aurin; Alam, Md Mahamudul; Chowdhury, Mahmudul Hasan; Khan, Shamsun Nahar; Sultana, Gazi Nurun Nahar

2015-04-02

The rhizome of Curcuma amada has been used as a folk medicine for the treatment of rheumatic disorders in the northern part of Bangladesh and has also used for the treatment of inflammation and fever in the Ayurvedic and Unani systems of medicine. Aim of the study was to investigate the analgesic principle of the MeOH extract of the rhizome of Curcuma amada by an in vivo bioassay guided chromatographic separation and purification, and the structure elucidation of the purified compound by spectroscopic methods. Dried powder of Curcuma amada rhizomes was extracted with MeOH. The analgesic activity of the crude extract and its chromatographic fractions as well as the purified compound itself was evaluated by the acetic acid induced writhing method and the formalin induced licking test in Swiss albino mice. The MeOH extract was separated by chromatographic methods and the pure active compound was purified by crystallization in hexanes. The structure of the pure compound was then elucidated by spectroscopic methods. The MeOH extract of Curcuma amada exhibited 41.63% and 45.53% inhibitions in the acetic acid induced writhing method at doses of 200mg/kg and 400mg/kg, respectively. It also exerted 20.43% and 28.50% inhibitions in early phase at doses of 200mg/kg and 400mg/kg, respectively, and 30.41% and 42.95% inhibitions in late phase at doses of 200mg/kg and 400mg/kg, respectively in the formalin induced licking test. Vacuum Liquid Chromatography (VLC) of crude extract yielded five fractions and Fr. 1 was found to have the most potent analgesic activity with inhibitions of 36.96% in the acetic acid induced writhing method and 47.51% (early phase), 39.50% (late phase) in the formalin induced licking test at a dose of 200mg/kg. Column chromatography of Fr. 1 on silica gel generated seven fractions (SF. 1-SF. 7). SF. 2 showed the most potent activity with inhibition of 49.81% in the acetic acid induced writhing method at a dose of 100mg/kg. Crystallization of SF. 2 yielded (1) (zederone, 520mg). It showed statistically significant inhibitions of 38.91% and 52.14% in the acetic acid induced writhing method at doses of 20mg/kg and 40mg/kg, respectively. Moreover, it also showed statistically significant inhibitions of 27.79% and 29.93% (early phase) and of 38.24% and 46.08% (late phase) in the formalin induced licking test at doses of 20mg/kg and 40mg/kg, respectively. Isolation and characterization of zederone (1) as analgesic principle of Curcuma amada corroborate its use in Ayurvedic, Unani and folk medicines for the treatment of rheumatic disorders and also contributing to its pharmacological validation. Copyright © 2015 Elsevier Ireland Ltd. All rights reserved.

Two new compounds from the fruiting bodies of Ganoderma philippii.

PubMed

Yang, Shuang; Ma, Qing-Yun; Kong, Fan-Dong; Xie, Qing-Yi; Huang, Sheng-Zhuo; Zhou, Li-Man; Dai, Hao-Fu; Yu, Zhi-Fang; Zhao, You-Xing

2018-03-01

Two new compounds, philippin (1) and 3β,9α,14α-trihydroxy-(22E,24R)-ergost-22-en-7-one (2), were isolated from the fruiting bodies of Ganoderma philippii. Their structures were elucidated on the basis of the spectroscopic technologies, including 1D and 2D NMR as well as MS. The bioassay of inhibitory activity against acetylcholinesterase (AChE) showed compound 1 exhibited weak inhibitory activity against AChE.

Five new diarylheptanoids from the rhizomes of Curcuma kwangsiensis and their antiproliferative activity.

PubMed

Chen, Shao-Dan; Gao, Jin-Tao; Liu, Jing-Gong; Liu, Bo; Zhao, Rui-Zhi; Lu, Chuan-Jian

2015-04-01

Five new diarylheptanoids (1-5), along with nine known ones (6-14), were isolated from the rhizomes of Curcuma kwangsiensis. Their structures were established on the basis of spectroscopic analyses. Compounds 1-3 were cyclic diarylheptanoids rarely discovered from C. kwangsiensis. Of all the isolated compounds, compound 4 showed moderate antiproliferative activity on HH and HaCaT cells. Copyright © 2015. Published by Elsevier B.V.

Laser Spectroscopy for Atmospheric and Environmental Sensing

PubMed Central

Fiddler, Marc N.; Begashaw, Israel; Mickens, Matthew A.; Collingwood, Michael S.; Assefa, Zerihun; Bililign, Solomon

2009-01-01

Lasers and laser spectroscopic techniques have been extensively used in several applications since their advent, and the subject has been reviewed extensively in the last several decades. This review is focused on three areas of laser spectroscopic applications in atmospheric and environmental sensing; namely laser-induced fluorescence (LIF), cavity ring-down spectroscopy (CRDS), and photoluminescence (PL) techniques used in the detection of solids, liquids, aerosols, trace gases, and volatile organic compounds (VOCs). PMID:22303184

Cytotoxic halogenated monoterpenes from Plocamium cartilagineum.

PubMed

Sabry, Omar M M; Goeger, Douglas E; Valeriote, Frederick A; Gerwick, William H

2017-02-01

As a result of our efforts to identify bioactive agents from marine algae, we have isolated and identified one new halogenated monoterpene 1 [(-)-(5E,7Z)-348-trichloro-7-dichloromethyl-3-methyl-157-octatriene] in addition to three known compounds (2, 3 and 4) from the red alga Plocamium cartilagineum collected by hand from the eastern coast of South Africa. Compound 1 was found to be active as a cytotoxic agent in human lung cancer (NCI-H460) and mouse neuro-2a cell lines (IC 50 4 μg/mL). Two of these compounds (3 and 4) were found to have cytotoxic activity in other cell line assays, especially against human leukaemia and human colon cancers (IC 50 1.3 μg/mL). None of these metabolites were active as sodium channel blockers or activators. All structures were determined by spectroscopic methods (UV, IR, LRMS, HRMS, 1D NMR and 2D NMR). 1D and 2D NOE experiments were carried out on these compounds to confirm the geometry of the double bonds.

Olean-18-ene triterpenoids from Celastraceae species inhibit HIV replication targeting NF-kB and Sp1 dependent transcription.

PubMed

Osorio, Alex A; Muñóz, Alejandro; Torres-Romero, David; Bedoya, Luis M; Perestelo, Nayra R; Jiménez, Ignacio A; Alcamí, José; Bazzocchi, Isabel L

2012-06-01

In the present study we report the isolation of nine new olean-18-ene triterpenes (1-9), along with three known ones (10-12), from Cassine xylocarpa and Maytenus jelskii. Their stereostructures have been elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR techniques (COSY, ROESY, HSQC and HMBC), and spectrometric methods. The natural compounds and derivatives 13-15 have been tested for their potential as inhibitors of human immunodeficiency virus type 1 replication. Five compounds from this series displayed potent antiviral activity with IC(50)s in the micromolar range (1, 3, 4, 7 and 8) being 1 and 8 the most active compounds. The target of these compounds was different from antiretroviral drugs currently licensed as they act as inhibitors of enhancer-dependent transcription. The structure-activity relationships were established based on the regiosubstitution and oxidation degree of the triterpene scaffold, revealing that these aspects were able to modulate the selectivity and intensity of HIV inhibition. Copyright © 2012 Elsevier Masson SAS. All rights reserved.

Efficient synthesis and physicochemical characterization of natural danshensu, its S isomer and intermediates thereof

NASA Astrophysics Data System (ADS)

Sidoryk, Katarzyna; Filip, Katarzyna; Cmoch, Piotr; Łaszcz, Marta; Cybulski, Marcin

2018-02-01

The synthesis and molecular structure details of R- 3,4-dihydroxyphenyl lactic acid (danshensu) and related compounds, i.e. S isomer and the key intermediates have been described. Danshensu is an important water soluble phenolic acid of Salvia miltiorrhiza herb (danshen or red sag) with numerous applications in traditional Chinese medicine (TCM). Our synthetic approach was based on the Knoevenagel condensation of the protected 3,4-dihydroxybenzaldehyd and Meldrum acid derivative, followed by asymmetric Sharples dihydroxylation, reductive mono dehydroxylation and final deprotection. All compounds were characterized by various spectroscopic techniques: 1H-, 13C- magnetic resonance (NMR); Fourier-transformed infrared (FTIR); Raman, HR mass spectroscopy. For the determination of compound optical purities original HPLC methods were developed which allowed for the efficient resolution of danshensu R and S enantiomers as well as its intermediate enantiomers, using commercially available chiral stationary phases. Furthermore, in order to better understand danshensu specificity as a potential API in drug formulation, the physicochemical properties of the compounds were studied by thermal analysis, including differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA).

Identification and Characterization of an Anti-Fibrotic Benzopyran Compound Isolated from Mangrove-Derived Streptomyces xiamenensis

PubMed Central

Xu, Min-Juan; Liu, Xiao-Jin; Zhao, Yi-Lei; Liu, Dong; Xu, Zhen-Hao; Lang, Xiao-Meng; Ao, Ping; Lin, Wen-Han; Yang, Song-Lin; Zhang, Zhi-Gang; Xu, Jun

2012-01-01

An anti-fibrotic compound produced by Streptomycesn xiamenensis, found in mangrove sediments, was investigated for possible therapeutic effects against fibrosis. The compound, N-[[3,4-dihydro-3S-hydroxy-2S-methyl-2-(4′R-methyl-3′S-pentenyl)-2H-1-benzopyran-6-yl]carbonyl]-threonine (1), was isolated from crude extracts and its structure, including the absolute configuration was determined by extensive spectroscopic data analyses, Mosher’s method, Marfey’s reagent and quantum mechanical calculations. In terms of biological effects, this compound inhibits the proliferation of human lung fibroblasts (WI26), blocks adhesion of human acute monocytic leukemia cells (THP-1) to a monolayer of WI26 cells, and reduces the contractile capacity of WI26 cells in three-dimensional free-floating collagen gels. Altogether, these data indicate that we have identified a bioactive alkaloid (1) with multiple inhibitory biological effects on lung excessive fibrotic characteristics, that are likely involved in fibrosis, suggesting that this molecule might indeed have therapeutic potential against fibrosis. PMID:22611360

Structural and Sensory Characterization of Novel Sesquiterpene Lactones from Iceberg Lettuce.

PubMed

Mai, Franziska; Glomb, Marcus A

2016-01-13

Lactuca sativa var. capitate (iceberg lettuce) is a delicious vegetable and popular for its mild taste. Nevertheless, iceberg lettuce is a source of bitter substances, such as the sesquiterpene lactones. Chemical investigations on the n-butanol extract led to the isolation of three novel sesquiterpene lactones. All compounds were isolated by multilayer countercurrent chromatography followed by preparative high-performance liquid chromatography. The structures were verified by means of spectroscopic methods, including NMR and mass spectrometry techniques. For the first time 11ß,13-dihydrolactucin-8-O-sulfate (jaquinelin-8-O-sulfate) was structurally elucidated and identified in plants. In addition, the sesquiterpene lactones cichorioside B and 8-deacetylmatricarin-8-O-sulfate were identified as novel ingredients of iceberg lettuce. Further flowering plants in the daisy family Asteraceae were examined for the above three compounds. At least one of the compounds was identified in nine plants. The comparison between the lettuce butt end and the leaves of five types of the Cichorieae tribe showed an accumulation of the compounds in the butt end. Further experiments addressed the impact of sesquiterpene lactones on color formation and bitter taste.

Chemical constituents from Hericium erinaceus and their ability to stimulate NGF-mediated neurite outgrowth on PC12 cells.

PubMed

Zhang, Cheng-Chen; Yin, Xia; Cao, Chen-Yu; Wei, Jing; Zhang, Qiang; Gao, Jin-Ming

2015-11-15

One new meroterpenoid, named hericenone K (11), along with 10 known compounds (1-10), ergosterol peroxide (1), cerevisterol (2), 3β,5α,9α-trihydroxy-ergosta-7,22-dien-6-one (3), inoterpene A (4), astradoric acid C (5), betulin (6), oleanolic acid (7), ursolic acid (8), hemisceramide (9), and 3,4-dihydro-5-methoxy-2-methyl-2-(4'-methyl-2'-oxo-3'-pentenyl)-9(7H)-oxo-2H-furo[3,4-h]benzopyran (10), was isolated from the fruiting bodies of the mushroom Hericium erinaceus. Their structures were characterized on the basis of spectroscopic methods, as well as through comparison with previously reported data. Compounds 3-6, 8, and 9 were isolated from Hericium species for the first time. Compounds 10 and 11 was suggested to be racemic by the CD spectrum data and specific rotations, which ware resolved by chiral HPLC into respective enantiomers. Compounds 1-3, (±)-10, (-)-10 and (+)-10 in the presence of NGF (20 ng/mL) exerted a significant increase in neurite-bearing cells. Copyright © 2015 Elsevier Ltd. All rights reserved.

Antibacterial compounds from Salvia adenophora Fernald (Lamiaceae).

PubMed

Bisio, Angela; Schito, Anna Maria; Ebrahimi, Samad Nejad; Hamburger, Matthias; Mele, Giacomo; Piatti, Gabriella; Romussi, Giovanni; Dal Piaz, Fabrizio; De Tommasi, Nunziatina

2015-02-01

From the aerial parts of Salvia adenophora Fernald four derivatives of 12-oxo-phytodienoic acid (1-4) together with five clerodane diterpenoids (5, 6, 8-10), and one known diterpene (7) have been isolated. Compounds 1-6 and 8-10 are described for the first time. The structures were established by extensive 1D, 2D NMR and HRESI-TOFMS spectroscopic methods. Finally, the absolute configuration has been established by comparing of experimental and quantum chemical calculation of ECD spectra. Despite a total lack of antimicrobial activity of the plant extract, hinting to the existence of antagonistic interactions in the crude material, three oxylipins (2-4) displayed a promising inhibition on Gram-positive multidrug-resistant clinical strains including Staphylococcus aureus, Streptococcus agalactiae and, particularly, Staphylococcus epidermidis, while the compounds 9 and 10 revealed a specific and strain-dependent activity against S. epidermidis. Interestingly, the inhibition provided by these compounds was independent of the resistance patterns of these pathogens to classic antibiotics. No action was reported on Gram-negative strains nor on Candida albicans. These results confirm that clerodanes and, particularly, prostaglandin-like compounds can be considered as interesting antimicrobial agents deserving further study. Copyright © 2014 Elsevier Ltd. All rights reserved.

Vibrational, NMR and UV-visible spectroscopic investigation and NLO studies on benzaldehyde thiosemicarbazone using computational calculations

NASA Astrophysics Data System (ADS)

Moorthy, N.; Prabakar, P. C. Jobe; Ramalingam, S.; Pandian, G. V.; Anbusrinivasan, P.

2016-04-01

In order to investigate the vibrational, electronic and NLO characteristics of the compound; benzaldehyde thiosemicarbazone (BTSC), the XRD, FT-IR, FT-Raman, NMR and UV-visible spectra were recorded and were analysed with the calculated spectra by using HF and B3LYP methods with 6-311++G(d,p) basis set. The XRD results revealed that the stabilized molecular systems were confined in orthorhombic unit cell system. The cause for the change of chemical and physical properties behind the compound has been discussed makes use of Mulliken charge levels and NBO in detail. The shift of molecular vibrational pattern by the fusing of ligand; thiosemicarbazone group with benzaldehyde has been keenly observed. The occurrence of in phase and out of phase molecular interaction over the frontier molecular orbitals was determined to evaluate the degeneracy of the electronic energy levels. The thermodynamical studies of the temperature region 100-1000 K to detect the thermal stabilization of the crystal phase of the compound were investigated. The NLO properties were evaluated by the determination of the polarizability and hyperpolarizability of the compound in crystal phase. The physical stabilization of the geometry of the compound has been explained by geometry deformation analysis.

Anti-inflammatory effects of phenolic compounds isolated from the fruits of Artocarpus heterophyllus.

PubMed

Fang, Song-Chwan; Hsu, Chin-Lin; Yen, Gow-Chin

2008-06-25

Artocarpus heterophyllus Lam is a large evergreen tree cultivated throughout Southeast Asia for its fruits. Its leaves and roots have been used for medicinal purposes. The aim of this work was to study the in vitro anti-inflammatory effects of phenolic compounds isolated from the ethyl acetate extracts of the fruits of Artocarpus heterophyllus. Three phenolic compounds were characterized as artocarpesin [5,7,2',4'-tetrahydroxy-6-(3-methylbut-3-enyl) flavone] ( 1), norartocarpetin (5,7,2',4'-tetrahydroxyflavone) ( 2), and oxyresveratrol [ trans-2,4,3',5'-tetrahydroxystilbene] ( 3) by spectroscopic methods and through comparison with data reported in the literatures. The anti-inflammatory effects of the isolated compounds ( 1- 3) were evaluated by determining their inhibitory effects on the production of proinflammatory mediators in lipopolysaccharide (LPS)-activated RAW 264.7 murine macrophage cells. These three compounds exhibited potent anti-inflammatory activity. The results indicated that artocarpesin ( 1) suppressed the LPS-induced production of nitric oxide (NO) and prostaglandin E 2 (PGE 2) through the down-regulation of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX-2) protein expressions. Thus, artocarpesin ( 1) may provide a potential therapeutic approach for inflammation-associated disorders.

Three new areca alkaloids from the nuts of Areca catechu.

PubMed

Tang, Shao-Nan; Zhang, Jian; Liu, Dong; Liu, Zhi-Wen; Zhang, Xiao-Qi; Ye, Wen-Cai

2017-12-01

Three new areca alkaloids arecatemines A-C (1-3), together with five known ones (4-8), were isolated from the nuts of Areca catechu. The structures of new compounds including absolute configurations were elucidated using comprehensive spectroscopic and electronic circular dichroism (ECD). The known compounds were identified by comparing with data in the literature.

Spectroscopic methods for aqueous cyclodextrin inclusion complex binding measurement for 1,4-dioxane, chlorinated co-contaminants, and ozone

NASA Astrophysics Data System (ADS)

Khan, Naima A.; Johnson, Michael D.; Carroll, Kenneth C.

2018-03-01

Recalcitrant organic contaminants, such as 1,4-dioxane, typically require advanced oxidation process (AOP) oxidants, such as ozone (O3), for their complete mineralization during water treatment. Unfortunately, the use of AOPs can be limited by these oxidants' relatively high reactivities and short half-lives. These drawbacks can be minimized by partial encapsulation of the oxidants within a cyclodextrin cavity to form inclusion complexes. We determined the inclusion complexes of O3 and three common co-contaminants (trichloroethene, 1,1,1-trichloroethane, and 1,4-dioxane) as guest compounds within hydroxypropyl-β-cyclodextrin. Both direct (ultraviolet or UV) and competitive (fluorescence changes with 6-p-toluidine-2-naphthalenesulfonic acid as the probe) methods were used, which gave comparable results for the inclusion constants of these species. Impacts of changing pH and NaCl concentrations were also assessed. Binding constants increased with pH and with ionic strength, which was attributed to variations in guest compound solubility. The results illustrate the versatility of cyclodextrins for inclusion complexation with various types of compounds, binding measurement methods are applicable to a wide range of applications, and have implications for both extraction of contaminants and delivery of reagents for treatment of contaminants in wastewater or contaminated groundwater.

The role of simulation chambers in the development of spectroscopic techniques: campaigns at EUPHORE

NASA Astrophysics Data System (ADS)

Ródenas, Milagros; Muñoz, Amalia; Euphore Team

2016-04-01

Simulation chambers represent a very useful tool for the study of chemical reactions and their products, but also to characterize instruments. The development of spectroscopic techniques throughout the last decades has benefited from tests and intercomparison exercises carried out in chambers. In fact, instruments can be exposed to various controlled atmospheric scenarios that account for different environmental conditions, eliminating the uncertainties associated to fluctuations of the air mass, which must be taken into account when extrapolating results to the real conditions. Hence, a given instrument can be characterized by assessing its precision, accuracy, detection limits, time response and potential interferences in the presence of other chemical compounds, aerosols, etc. This implies that the instrument can be calibrated and validated, which allows to enhance the features of the instrument. Moreover, chambers are also the scenario of intercomparison trials, permitting multiple instruments to sample from the same well-mixed air mass simultaneously. An overview of different campaigns to characterize and/or intercompare spectroscopic techniques that have taken place in simulation chambers will be given; in particular, those carried out at EUPHORE (two twin domes, 200 m3 each, Spain), where various intercomparison exercises have been deployed under the frame of European projects (e.g. TOXIC, FIONA, PSOA campaigns supported by EUROCHAMP-II). With the common aim of measuring given compounds (e.g. HONO, NO2, OH, glyoxal, m-glyoxal, etc), an important number of spectroscopic instruments and institutions have been involved in chamber experiments, having the chance to intercompare among them and also with other non-spectroscopic systems (e.g. monitors, cromatographs, etc) or model simulations.

Synthesis, spectroscopic, single crystal diffraction and potential nonlinear optical properties of novel pyrazoline derivatives: Interplay of experimental and computational analyses.

PubMed

Arshad, Muhammad Nadeem; Birinji, Abdulhadi Salih; Khalid, Muhammad; Asiri, Abdullah M; Al-Amry, Khalid A; Aqlan, Faisal M S; Braga, Ataualpa A C

2018-09-05

Pyrazoline are widely being studied due to their potential applications in chemical field. Herein, five pyrazolines compounds were synthesized and characterized spectroscopically using nuclear magnetic resonance techniques ( 1 H NMR & 13 C NMR) to determine the structures of molecules along-with UV-Visible and infrared (FT-IR) studies for additional spectroscopic support in characterization of entitle synthesized molecules. Unit cells, specific space groups, bond lengths, bond angles and hydrogen bonding interactions were determined by the x-ray diffraction studies. Further, computational study of compounds with B3LYP/6-311 + G(d,p) level were carried out to explore optimized geometry, spectroscopic data for FT-IR, frontier molecular orbitals (FMOs) and non-linear optical (NLO) parameters. While, UV-Vis spectral were performed by TD-DFT/B3LYP/6-311 + G(d,p) level. The experimental results of spectroscopic and single crystal studies were compared and found in good agreement with the computational. The global reactivity parameters have been calculated with the help of the energy of FMOs. The order for the total first and second order hyperpolarizabilities of 1-5 is found in the following orders: 1 > 4 > 3 > 5 > 2 and 1 > 4 > 5 > 2 > 3 respectively. Overall, greater NLO response than urea molecule prove that investigated molecules are excellent candidate for NLO applications. Copyright © 2018 Elsevier B.V. All rights reserved.

Sesquiterpene Lactones from Gynoxys verrucosa and their Anti-MRSA Activity

PubMed Central

Ordóñez, Paola E.; Quave, Cassandra L.; Reynolds, William F.; Varughese, Kottayil I.; Berry, Brian; Breen, Philip J.; Malagón, Omar; Smeltzer, Mark S.; Compadre, Cesar M.

2011-01-01

Ethnopharmacological relevance Because of its virulence and antibiotic resistance, Staphylococcus aureus is a more formidable pathogen now than at any time since the pre-antibiotic era. In an effort to identify and develop novel antimicrobial agents with activity against this pathogen, we have examined Gynoxys verrucosa Wedd (Asteraceae), an herb used in traditional medicine in southern Ecuador for the treatment and healing of wounds. Materials and Methods The sesquiterpene lactones leucodine (1) and dehydroleucodine (2) were extracted and purified from the aerial parts of G. verrucosa, and their structure was elucidated by spectroscopic methods and single-crystal X-ray analysis. The in vitro anti-microbial activity of G. verrucosa extracts and its purified constituents was determined against six clinical isolates including S. aureus and Staphylococcus epidermidis strains with different drug-resistance profiles, using the microtiter broth method. Results Compound 1 has very low activity, while compound 2 has moderate activity with MIC50s between 49 and195 μg/mL. The extract of G. verrucosa has weak activity with MIC50s between 908 and 3290 μg/mL. Conclusions We are reporting the full assignment of the 1H-NMR and 13C-NMR of both compounds, and the crystal structure of compound 2, for the first time. Moreover, the fact that compound 2 has antimicrobial activity and compound 1 does not, demonstrates that the exocyclic conjugated methylene in the lactone ring is essential for the antimicrobial activity of these sesquiterpene lactones. However, the weak activity observed for the plants extracts, does not explain the use of G. verrucosa in traditional medicine for the treatment of wounds and skin infections. PMID:21782013

Determination of the antileukemic drug mitoguazone and seven other closely related bis(amidinohydrazones) in human blood serum by high-performance liquid chromatography.

PubMed

Koskinen, M; Elo, H; Lukkari, P; Riekkola, M L

1996-10-11

A reversed-phase (C18) HPLC method with diode-array detection was developed for the separation and determination of methylglyoxal bis(amidinohydrazone) (mitoguazone) and seven closely related aliphatic analogs thereof, namely the bis(amidinohydrazones) of glyoxal, dimethylglyoxal, ethylmethylglyoxal, methylpropylglyoxal, butylmethylglyoxal, diethylglyoxal and dipropylglyoxal. The mobile phase consisted of a non-linear binary gradient of methanol and 0.03 M aqueous sodium acetate buffer (pH 4.3). Good separation of the eight congeners was achieved. On increasing the methanol content of the eluent, the bis(amidinohydrazones) eluted in the order of increasing number of carbon atoms in the side-chains. The method was also applied to the quantitative analysis of the compounds in aqueous solution and, combined with ultrafiltration, for the separation of the eight congeners in spiked human blood serum. A separate simplified method for the quantitative determination of each of the compounds in spiked human blood serum samples was also developed. The methods developed made for the first time possible the simultaneous HPLC analysis of more than one bis(amidinohydrazones). The results obtained indicate that the bis(amidinohydrazones) studied obviously have a distinct tendency to form ion associates with acetate ions and probably also other carboxylate ions in aqueous solution. This aspect may be of biochemical significance, especially concerning the intracellular binding of the compounds. Each one of the compounds studied invariably gave rise to one peak only, this result supporting the theory that the conventional synthesis of each of the compounds gives rise to one geometrical isomer only. This result is completely in agreement with the results of previous proton and carbon NMR spectroscopic as well as X-ray diffraction studies.

Antileishmanial Phenylpropanoids from the Leaves of Hyptis pectinata (L.) Poit

PubMed Central

Falcao, Rosangela A.; do Nascimento, Patricia L. A.; de Souza, Silvana A.; da Silva, Telma M. G.; de Queiroz, Aline C.; da Matta, Carolina B. B.; Moreira, Magna S. A.; Camara, Celso A.; Silva, Tania M. S.

2013-01-01

Hyptis pectinata, popularly known in Brazil as “sambacaitá” or “canudinho,” is an aromatic shrub largely grown in the northeast of Brazil. The leaves and bark are used in an infusion for the treatment of throat and skin inflammations, bacterial infections, pain, and cancer. Analogues of rosmarinic acid and flavonoids were obtained from the leaves of Hyptis pectinata and consisted of two new compounds, sambacaitaric acid (1) and 3-O-methyl-sambacaitaric acid (2), and nine known compounds, rosmarinic acid (3), 3-O-methyl-rosmarinic acid (4), ethyl caffeate (5), nepetoidin A (6), nepetoidin B (7), cirsiliol (8), circimaritin (9), 7-O-methylluteolin (10), and genkwanin (11). The structures of these compounds were determined by spectroscopic methods. Compounds 1–5, and 7 were evaluated in vitro against the promastigote form of L. braziliensis, and the ethanol extract. The hexane, ethyl acetate, and methanol-water fractions were also evaluated. The EtOH extract, the hexane extract, EtOAc, MeOH:H2O fractions; and compounds 1, 2 and 4 exhibited antileishmanial activity, and compound 1 was as potent as pentamidine. In contrast, compounds 3, 5, and 7 did not present activity against the promastigote form of L. braziliensis below 100 µM. To our knowledge, compounds 1 and 2 are being described for the first time. PMID:23983783

[Chemical constituents of Carya cathayensis and their antitumor bioactivity].

PubMed

Wu, De-lin; Chen, Shi-yun; Liu, Jing-song; Jin, Chuan-shan; Xu, Feng-qing

2011-07-01

To investigate the chemical constituents of Carya cathayensis and their antitumor bioactivity. The compounds were isolated by Sephadex LH-20 and silica gel column chromatography. Their structures were identified by physicochemical properties and spectroscopic analysis. Then their cytotoxic activity was studied. Five compounds were elucidated as chrysophanol (1), physcion (2), beta-sitosterol (3), pinostrobin(4), 4,8-dihydroxy-1-tetralone (5). Compounds 2 and 5 are isolated from Carya cathayensis for the first time. In the MTT antitumor experiments, the compounds 1,4 and 5 have the cytotoxic activity to KB cell.

Klymollins T-X, bioactive eunicellin-based diterpenoids from the soft coral Klyxum molle.

PubMed

Chang, Fang-Yu; Hsu, Fang-Jung; Tai, Chi-Jen; Wei, Wen-Chi; Yang, Ning-Sun; Sheu, Jyh-Horng

2014-05-22

Five new eunicellin-based diterpenoids, klymollins T-X (1-5), along with two known compounds (6 and 7) have been isolated from the soft coral Klyxum molle. The structures of these new metabolites were elucidated by extensive spectroscopic analysis and by comparison with related known compounds. Compound 5 was found to exert significant in vitro anti-inflammatory activity against LPS-stimulated RAW264.7 macrophage cells. Furthermore, compounds 4 and 7 were shown to exhibit cytotoxicity against a limited panel of human cancer cell lines.

Photophysical Study of Novel Perylene Analogues for Biophysical Applications

NASA Astrophysics Data System (ADS)

Palos-Chávez, Jorge; Penick, Mark; Negrete, George; Brancaleon, Lorenzo

2011-03-01

Perylene and perylene derivatives have been shown to be useful in a variety of photoinitiated applications, such as molecular dyes, organic solar cells, etc. Recently we started the characterization of novel 3,9-perylene analogues which could potentially lead to the synthesis of novel molecules with improved ability to separate charges. We have characterized the basic photophysical properties of these molecules, and we are currently investigating the photochemistry that leads to photoproducts in chlorinated compounds. Spectroscopic measurements show the substantial changes in photophysical parameters consistent with the conversion of the original compounds into photoproducts. SEM and AFM imaging show that these photoproducts form ordered particles. Mass spectrometry studies have confirmed the presence of these photoproducts as well. Additional studies are underway concerning the use of these novel perylene analogues in binding to biological structures such as proteins. It is hoped that these compounds will prove useful for biophysical applications, specifically in studying the manipulation of protein conformation via physical methods. Supported by NIH/NIGMS MBRS RISE GM-60655.

Rhizovarins A-F, Indole-Diterpenes from the Mangrove-Derived Endophytic Fungus Mucor irregularis QEN-189.

PubMed

Gao, Shu-Shan; Li, Xiao-Ming; Williams, Katherine; Proksch, Peter; Ji, Nai-Yun; Wang, Bin-Gui

2016-08-26

Genome mining of the fungus Mucor irregularis (formerly known as Rhizomucor variabilis) revealed the presence of various gene clusters for secondary metabolite biosynthesis, including several terpene-based clusters. Investigation into the chemical diversity of M. irregularis QEN-189, an endophytic fungus isolated from the fresh inner tissue of the marine mangrove plant Rhizophora stylosa, resulted in the discovery of 20 structurally diverse indole-diterpenes including six new compounds, namely, rhizovarins A-F (1-6). Among them, compounds 1-3 represent the most complex members of the reported indole-diterpenes. The presence of an unusual acetal linked to a hemiketal (1) or a ketal (2 and 3) in an unprecedented 4,6,6,8,5,6,6,6,6-fused indole-diterpene ring system makes them chemically unique. Their structures and absolute configurations were elucidated by spectroscopic analysis, modified Mosher's method, and chemical calculations. Each of the isolated compounds was evaluated for antitumor activity against HL-60 and A-549 cell lines.

Leucettamol A: a new inhibitor of Ubc13-Uev1A interaction isolated from a marine sponge, Leucetta aff. microrhaphis.

PubMed

Tsukamoto, Sachiko; Takeuchi, Tomoharu; Rotinsulu, Henki; Mangindaan, Remy E P; van Soest, Rob W M; Ukai, Kazuyo; Kobayashi, Hisayoshi; Namikoshi, Michio; Ohta, Tomihisa; Yokosawa, Hideyoshi

2008-12-15

A compound that inhibits the formation of a complex composed of the ubiquitin E2 enzyme Ubc13 and Uev1A was isolated from the marine sponge Leucetta aff. microrhaphis. The compound was identified as leucettamol A (1) by spectroscopic analysis. Its inhibition of Ubc13-Uev1A interaction was tested by the ELISA method, revealing an IC(50) value of 50 microg/mL. The compound is the first inhibitor of Ubc13-Uev1A interaction, that is, that of the E2 activity of Ubc13. Such inhibitors are presumed to be leads for anti-cancer agents that upregulate activity of the tumor suppressor p53 protein. Interestingly, hydrogenation of 1 increased its inhibitory activity with an IC(50) value of 4 microg/mL, while its tetraacetate derivative was inactive, indicating that the hydroxy and/or amino groups of 1 are required for the inhibition.

Tautomerism in N-(2-hydroxy-1-naphthylidene)amino acids and the search for an answer to the difficult question about where the proton belongs

NASA Astrophysics Data System (ADS)

Warncke, Gisela; Fels, Sabine; Brendler, Erica; Böhme, Uwe

2016-08-01

N-(2-hydroxy-1-naphthylidene)-L-valine 1, N-(2-hydroxy-1-naphthylidene)-L-phenylalanine 2, and N-(2-hydroxy-1-naphthylidene)-L-threonine 3 were prepared and characterized with spectroscopic methods, elemental analyses, and values of optical rotation. Compound 1 undergoes a solid state order-disorder phase transition at 231 K. The X-ray structures of the high and low temperature phase of 1 have been determined. Single crystal X-ray structures of 2 and 3 have been determined as well. The tautomerism of N-(2-hydroxy-1-naphthylidene)amino acid derivatives is discussed controversial in the literature. A bond lengths statistical analysis shows that all three compounds exist uniformly in the keto-amine form in the solid state. Quantum chemical calculations, NMR, and UV-Vis spectroscopy were used to obtain further insight into the existence of phenol-imine and keto-amine structures in this class of compounds.

Induction of quinone reductase (QR) by withanolides isolated from Physalis angulata L. var. villosa Bonati (Solanaceae).

PubMed

Ding, Hui; Hu, Zhijuan; Yu, Liyan; Ma, Zhongjun; Ma, Xiaoqiong; Chen, Zhe; Wang, Dan; Zhao, Xiaofeng

2014-08-01

In the present study, the EtOAc extract of the persistent calyx of Physalis angulata L. var. villosa Bonati (PA) was tested for its potential quinone reductase (QR) inducing activity with glutathione (GSH) as the substrate using an UPLC-ESI-MS method. The result revealed that the PA had electrophiles that could induce quinone reductase (QR) activity, which might be attributed to the modification of the highly reactive cysteine residues in Keap1. Herein, three new withanolides, compounds 3, 6 and 7, together with four known withanolides, compounds 1, 2, 4 and 5 were isolated from PA extract. Their structures were determined by spectroscopic techniques, including (1)H-, (13)C NMR (DEPT), and 2D-NMR (HMBC, HMQC, (1)H, (1)H-COSY, NOESY) experiments, as well as by HR-MS. All the seven compounds were tested for their QR induction activities towards mouse hepa 1c1c7 cells. Copyright © 2014 Elsevier Inc. All rights reserved.

A novel series of 1, 4-Dihydropyridine (DHP) derivatives bearing thiazolidin-4-one: From synthesis to structure

NASA Astrophysics Data System (ADS)

Bade, Tahseen S.; Ebrahimi, Hossein Pasha; Alsalim, Tahseen A.; Titinchi, Salam J. J.; Abbo, Hanna S.; Bolandnazar, Zeinab; Ebrahimi, Amirpasha

2017-06-01

A novel series of 1, 4-Dihydropyridine (DHP) thiazolidin-4-one compounds derived from dihydropyridine hydrazones Schiff bases with thioglycolic acid were synthesized through an efficient Hantzsch reaction and experimentally characterized by spectral methods using IR, 1H NMR, 13C NMR, and mass spectroscopic methods. Herein, DHPs were synthesized by an improved Hantzsch procedure in the excellent yields by three different conditions including reflux condensation, fusion, and the microwave irradiation. An additional comparison of applied methodology routes was used to confirm the advantages including short reaction time, good yields, and operational simplicity. Furthermore, the structural and electronic properties of the studied molecules were theoretically investigated by performing density functional theory (DFT) to access reliable results to the experimental values. The molecular geometry, HOMO, and LUMO of the studied compounds were calculated. The theoretical 13C chemical shift results were also calculated using the gauge independent atomic orbital (GIAO) approach and their respective linear correlations were obtained.

Spectroscopic and density functional theory studies of trans-3-(trans-4-imidazolyl)acrylic acid.

PubMed

Arjunan, V; Remya, P; Sathish, U; Rani, T; Mohan, S

2014-08-14

The structural parameters, thermodynamic properties and vibrational frequencies of the optimised geometry of trans-3-(trans-4-imidazolyl)acrylic acid have been determined from B3LYP methods with 6-311++G(**) and cc-pVTZ basis sets. The effects of substituents (acrylyl group) on the imidazole vibrational frequencies are analysed. The vibrational frequencies of the fundamental modes of trans-3-(trans-4-imidazolyl)acrylic acid have been precisely assigned and analysed and the theoretical results are compared with the experimental vibrations. (1)H and (13)C NMR isotropic chemical shifts are calculated and the assignments made are compared with the experimental values. The energies of important MO's of the compound are also determined from DFT method. The total electron density and electrostatic potential of the compound are determined by natural bond orbital analysis. Various reactivity and selectivity descriptors such as chemical hardness, chemical potential, softness, electrophilicity, nucleophilicity and the appropriate local quantities employing natural population analysis (NPA) are calculated. Copyright © 2014 Elsevier B.V. All rights reserved.

Infrared Spectroscopy as a Versatile Analytical Tool for the Quantitative Determination of Antioxidants in Agricultural Products, Foods and Plants

PubMed Central

Cozzolino, Daniel

2015-01-01

Spectroscopic methods provide with very useful qualitative and quantitative information about the biochemistry and chemistry of antioxidants. Near infrared (NIR) and mid infrared (MIR) spectroscopy are considered as powerful, fast, accurate and non-destructive analytical tools that can be considered as a replacement of traditional chemical analysis. In recent years, several reports can be found in the literature demonstrating the usefulness of these methods in the analysis of antioxidants in different organic matrices. This article reviews recent applications of infrared (NIR and MIR) spectroscopy in the analysis of antioxidant compounds in a wide range of samples such as agricultural products, foods and plants. PMID:26783838

Comprehensive quantum chemical and spectroscopic (FTIR, FT-Raman, 1H, 13C NMR) investigations of (1,2-epoxyethyl)benzene and (1,2-epoxy-2-phenyl)propane

NASA Astrophysics Data System (ADS)

Arjunan, V.; Anitha, R.; Devi, L.; Mohan, S.; Yang, Haifeng

2015-01-01

Aromatic epoxides are causative factors for mutagenic and carcinogenic activity of polycyclic arenes. The 1,2- or 2,3-epoxy compounds are widely used to a considerable extent in the textile, plastics, pharmaceutical, cosmetics, detergent and photochemical industries. The FTIR and FT-Raman spectra of (1,2-epoxyethyl)benzene and (1,2-epoxy-2-phenyl)propane are recorded in the regions 4000-400 cm-1 and 4000-100 cm-1, respectively. The observed fundamentals are assigned to different normal modes of vibration. The structure of the compound has been optimised with B3LYP method using 6-311++G** and cc-pVTZ basis sets. The IR and Raman intensities are determined. The total electron density and molecular electrostatic potential surfaces of the molecule are constructed by using B3LYP/6-311++G(d,p) method to display electrostatic potential (electron + nuclei) distribution. The electronic properties HOMO and LUMO energies were measured. Natural bond orbital analysis of the compounds has been performed to indicate the presence of intramolecular charge transfer. The 1H and 13C NMR chemical shifts of the molecules have been analysed.

Powder X-ray diffraction, infrared and 13C NMR spectroscopic studies of the homologous series of some solid-state zinc(II) and sodium(I) n-alkanoates

NASA Astrophysics Data System (ADS)

Nelson, Peter N.; Taylor, Richard A.

2015-03-01

A comparative study of the room temperature molecular packing and lattice structures for the homologous series of zinc(II) and sodium(I) n-alkanoates adduced from Fourier transform infrared and solid-state 13C NMR spectroscopic data in conjunction with X-ray powder diffraction measurements is carried out. For zinc carboxylates, metal-carboxyl bonding is via asymmetric bridging bidentate coordination whilst for the sodium adducts, coordination is via asymmetric chelating bidentate bonding. All compounds are packed in a monoclinic crystal system. Furthermore, the fully extended all-trans hydrocarbon chains are arranged as lamellar bilayers. For zinc compounds, there is bilayer overlap, for long chain adducts (nc > 8) but not for sodium compounds where methyl groups from opposing layers in the lamellar are only closely packed. Additionally, the hydrocarbon chains are extended along the a-axis of the unit cell for zinc compounds whilst for sodium carboxylates they are extended along the c-axis. These packing differences are responsible for different levels of Van der Waals effects in the lattices of these two series of compounds, hence, observed odd-even alternation is different. The significant difference in lattice packing observed for these two series of compounds is proposed to be due to the difference in metal-carboxyl coordination mode, arising from the different electronic structure of the central metal ions.

Ginkgolides and bilobalide: their physical, chromatographic and spectroscopic properties.

PubMed

van Beek, Teris A

2005-09-01

Ginkgolides A, B, C, J, K, L and M and bilobalide are rare terpene trilactones that have been isolated from leaves and root bark of the Chinese tree Ginkgo biloba. The structures of the highly oxidized ginkgolides were independently elucidated in the 1960s by the groups of Nakanishi and Sakabe. Later these compounds were found to be potent and selective antagonists of platelet activating factor, which fact triggered much new research. During the past 40 years, much physical, chromatographic and spectroscopic data have been published on these compounds in various, sometimes inaccessible, sources. The published melting points, solubility in different solvents, ionization constants, chromatographic behaviour, specific optical rotations, UV, IR, MS and NMR data, and X-ray studies are summarized and, where necessary, discussed. The literature until April 2005 has been reviewed.

Thiazole-based nitrogen mustards: Design, synthesis, spectroscopic studies, DFT calculation, molecular docking, and antiproliferative activity against selected human cancer cell lines

NASA Astrophysics Data System (ADS)

Łączkowski, Krzysztof Z.; Świtalska, Marta; Baranowska-Łączkowska, Angelika; Plech, Tomasz; Paneth, Agata; Misiura, Konrad; Wietrzyk, Joanna; Czaplińska, Barbara; Mrozek-Wilczkiewicz, Anna; Malarz, Katarzyna; Musioł, Robert; Grela, Izabela

2016-09-01

Synthesis, characterization and investigation of antiproliferative activity of ten thiazole-based nitrogen mustard against human cancer cells lines (MV4-11, A549, MCF-7 and HCT116) and normal mouse fibroblast (BALB/3T3) is presented. The structures of novel compounds were determined using 1H and 13C NMR, FAB(+)-MS, and elemental analyses. Among the derivatives, 5b, 5c, 5e, 5f and 5i were found to exhibit high activity against human leukaemia MV4-11 cells with IC50 values of 2.17-4.26 μg/ml. The cytotoxic activity of compound 5c and 5f against BALB/3T3 cells is up to 20 times lower than against cancer cell lines. Our results also show that compounds 5e and 5i have very strong activity against MCF-7 and HCT116 with IC50 values of 3.02-4.13 μg/ml. Moreover, spectroscopic characterization and cellular localization for selected compound were performed. In order to identify potential drug targets we perform computer simulations with DNA-binding site of hTopoI and hTopoII and quantum chemical calculation of interaction and binding energies in complexes of the five most active compounds with guanine.

New potential antitumoral fluorescent tetracyclic thieno[3,2- b]pyridine derivatives: interaction with DNA and nanosized liposomes

NASA Astrophysics Data System (ADS)

Castanheira, Elisabete Ms; Carvalho, Maria Solange D.; Rodrigues, Ana Rita O.; Calhelha, Ricardo C.; Queiroz, Maria-João Rp

2011-05-01

Fluorescence properties of two new potential antitumoral tetracyclic thieno[3,2- b]pyridine derivatives were studied in solution and in liposomes of DPPC (dipalmitoyl phosphatidylcholine), egg lecithin (phosphatidylcholine from egg yolk; Egg-PC) and DODAB (dioctadecyldimethylammonium bromide). Compound 1, pyrido[2',3':3,2]thieno[4,5- d]pyrido[1,2- a]pyrimidin-6-one, exhibits reasonably high fluorescence quantum yields in all solvents studied (0.20 ≤ ΦF ≤ 0.30), while for compound 2, 3-[( p-methoxyphenyl)ethynyl]pyrido[2',3':3,2]thieno[4,5- d]pyrido[1,2- a]pyrimidin-6-one, the values are much lower (0.01 ≤ ΦF ≤ 0.05). The interaction of these compounds with salmon sperm DNA was studied using spectroscopic methods, allowing the determination of intrinsic binding constants, K i = (8.7 ± 0.9) × 103 M-1 for compound 1 and K i = (5.9 ± 0.6) × 103 M-1 for 2, and binding site sizes of n = 11 ± 3 and n = 7 ± 2 base pairs, respectively. Compound 2 is the most intercalative compound in salmon sperm DNA (35%), while for compound 1 only 11% of the molecules are intercalated. Studies of incorporation of both compounds in liposomes of DPPC, Egg-PC and DODAB revealed that compound 2 is mainly located in the hydrophobic region of the lipid bilayer, while compound 1 prefers a hydrated and fluid environment.

Spectroscopic detection

DOEpatents

Woskov, Paul P.; Hadidi, Kamal

2003-01-01

In embodiments, spectroscopic monitor monitors modulated light signals to detect low levels of contaminants and other compounds in the presence of background interference. The monitor uses a spectrometer that includes a transmissive modulator capable of causing different frequency ranges to move onto and off of the detector. The different ranges can include those with the desired signal and those selected to subtract background contributions from those with the desired signal. Embodiments of the system are particularly useful for monitoring metal concentrations in combustion effluent.

Isoquinoline Alkaloids from Erythrinapoeppigiana (Leguminosae) and Cytotoxic Activity Against Breast Cancer Cells Line MCF-7 In Silico

NASA Astrophysics Data System (ADS)

Herlina, T.; Mardianingrum, R.; Gaffar, S.; Supratman, U.

2017-02-01

Erythrinapoeppigiana(Leguminosae) is a higher plant that has been used as a folk for the treatment of infection, fever, and inflammation. In the course of our continuing search for novel cytotoxic compounds from genus Erythrina, the methanol extract of E. poeppigiana showed a significant cytotoxic activity against breast cancer cells line MCF-7 in silico. The compounds in methanol extract of the E. poeppigiana was separated using a bioassay-guided fractionation. By using a cytotoxic activity to follow separation, the methylene chloride was separated by several column chromatography techniques on silica gel and ODS to yield three active compounds (1-3). The chemical structures of active compounds were determined on the basis of spectroscopic evidence and comparison with those identical compounds that previously reported and identified as a 10,11-dihydroxyerysodine (1) 6,7-dihydro-17-hydroxyerysotrine (2) 6,7-dihydro-11-methoxyerysotrine (3). Compounds (1-3) showed cytotoxic activity inhibits EGFR 2 against breast cancer cell line MCF-7 in silico molecular docking method with bond Gibbs free energy (ΔG) (kcal/mol) and inhibition constants (Ki) (nM) of value (-8.61121, 4.84×10-7) (-8.1145, 1.12×10-6) and (-7.3394, 4.14×10-6), respectively.

In Vitro Wound Healing Potential and Identification of Bioactive Compounds from Moringa oleifera Lam

PubMed Central

Muhammad, Abubakar Amali; Pauzi, Nur Aimi Syarina; Arulselvan, Palanisamy; Abas, Faridah; Fakurazi, Sharida

2013-01-01

Moringa oleifera Lam. (M. oleifera) from the monogeneric family Moringaceae is found in tropical and subtropical countries. The present study was aimed at exploring the in vitro wound healing potential of M. oleifera and identification of active compounds that may be responsible for its wound healing action. The study included cell viability, proliferation, and wound scratch test assays. Different solvent crude extracts were screened, and the most active crude extract was further subjected to differential bioguided fractionation. Fractions were also screened and most active aqueous fraction was finally obtained for further investigation. HPLC and LC-MS/MS analysis were used for identification and confirmation of bioactive compounds. The results of our study demonstrated that aqueous fraction of M. oleifera significantly enhanced proliferation and viability as well as migration of human dermal fibroblast (HDF) cells compared to the untreated control and other fractions. The HPLC and LC-MS/MS studies revealed kaempferol and quercetin compounds in the crude methanolic extract and a major bioactive compound Vicenin-2 was identified in the bioactive aqueous fraction which was confirmed with standard Vicenin-2 using HPLC and UV spectroscopic methods. These findings suggest that bioactive fraction of M. oleifera containing Vicenin-2 compound may enhance faster wound healing in vitro. PMID:24490175

Superbanone, A New 2-Aryl-3-benzofuranone and Other Bioactive Constituents from the Tube Roots of Butea superba.

PubMed

Boonsombat, Jutatip; Prachyawarakorn, Vilailak; Pansanit, Acharavadee; Mahidol, Chulabhorn; Ruchirawat, Somsak; Thongnest, Sanit

2017-07-01

Phytochemical investigation from the tube roots of Butea superba, led to the isolation and identification of a new 2-aryl-3-benzofuranone named superbanone (1), one benzoin, 2-hydroxy-1-(2-hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanone (2), eight pterocarpans (3 - 10), and eleven isoflavonoids (11 - 21). Compound 2 was identified for the first time as a natural product. The structure of the isolated compounds was elucidated using spectroscopic methods, mainly 1D- and 2D-NMR. The isolated compounds and their derivatives were evaluated for α-glucosidase inhibitory and antimalarial activities. Compounds 3, 7, 8, and 11 showed promising α-glucosidase inhibitory activity (IC 50  = 13.71 ± 0.54, 23.54 ± 0.75, 28.83 ± 1.02, and 12.35 ± 0.36 μm, respectively). Compounds 3 and 11 were twofold less active than the standard drug acarbose (IC 50  = 6.54 ± 0.04 μm). None of the tested compounds was found to be active against Plasmodium falciparum strain 94. On the basis of biological activity results, structure-activity relationships are discussed. © 2017 Wiley-VHCA AG, Zurich, Switzerland.

A New Platform for Profiling Degradation-Related Impurities Via Exploiting the Opportunities Offered by Ion-Selective Electrodes: Determination of Both Diatrizoate Sodium and Its Cytotoxic Degradation Product.

PubMed

Riad, Safaa M; Abd El-Rahman, Mohamed K; Fawaz, Esraa M; Shehata, Mostafa A

2018-05-01

Although the ultimate goal of administering active pharmaceutical ingredients (APIs) is to save countless lives, the presence of impurities and/or degradation products in APIs or formulations may cause harmful physiological effects. Today, impurity profiling (i.e., the identity as well as the quantity of impurity in a pharmaceutical) is receiving critical attention from regulatory authorities. Despite the predominant use of spectroscopic and chromatographic methods over electrochemical methods for impurity profiling of APIs, this work investigates the opportunities offered by electroanalytical methods, particularly, ion-selective electrodes (ISEs), for profiling degradation-related impurities (DRIs) compared with conventional spectroscopic and chromatographic methods. For a meaningful comparison, diatrizoate sodium (DTA) was chosen as the anionic X-ray contrast agent based on its susceptibility to deacetylation into its cytotoxic and mutagenic degradation product, 3,5-diamino-2,4,6 triiodobenzoic acid (DTB). This cationic diamino compound can be also detected as an impurity in the final product because it is used as a synthetic precursor for the synthesis of DTA. In this study, four novel sensitive and selective sensors for the determination of both DTA and its cytotoxic degradation products are presented. Sensors I and II were developed for the determination of the anionic drug, DTA, and sensors III and IV were developed for the determination of the cationic cytotoxic impurity. The use of these novel sensors not only provides a stability-indicating method for the selective determination of DTA in the presence of its degradation product, but also permits DRI profiling. Moreover, a great advantage of these proposed ISE systems is their higher sensitivity for the quantification of DTB relative to other spectroscopic and chromatographic methods, so it can measure trace amounts of DTB impurities in DTA bulk powder and pharmaceutical formulation without a need for preliminary separation.

A new 5-alkylresorcinol glucoside derivative from Cybianthus magnus.

PubMed

Cabanillas, B; Vásquez-Ocmín, P; Zebiri, I; Rengifo, E; Sauvain, M; Le, H L; Vaisberg, A; Voutquenne-Nazabadioko, L; Haddad, M

2016-01-01

One new 5-alkylresorcinol glucoside (1) was isolated from leaves of Cybianthus magnus, along with 12 known compounds (2-13), isolated from four plants belonging to Myrsinaceae family. Their structures were determined on the basis of spectroscopic analysis and by comparison of their spectral data with those reported in the literature. Among the tested molecules, only compound 2 displayed a strong cytotoxic activity with IC50 values ranging between 22 and 100 μM for all cell lines tested. One new 5-alkylresorcinol glucoside (1) was isolated from leaves of Cybianthus magnus, along with 12 known compounds, isolated from four plants belonging to Myrsinaceae family (2, 3 isolated from C. magnus; 4-7, 10 and 11 isolated from Myrsine latifolia; 4, 8 and 9 isolated from Myrsine sessiflora; 6, 7, 10, 12 and 13 isolated from Myrsine congesta). Their structures were determined on the basis of spectroscopic analysis and by comparison of their spectral data with those reported in the literature. So far, only nine 5-alkylresorcinol glucosides were isolated from leaves of Grevillea robusta. Since resorcinols are known to exhibit strong cytotoxic activity, compounds 1 and 2 were tested against cell lines 3T3, H460, DU145 and MCF-7 for cytotoxicity in vitro and compounds 3-13 were tested for their antileishmanial activity. Compound 2 displayed a strong cytotoxic activity with IC50 values ranging between 22 and 100 μM for all tested cell lines. Compounds 3-13 were not active against Leishmania amazonensis amastigotes.

One Pot Synthesis, Photophysical and X-ray Studies of Novel Highly Fluorescent Isoquinoline Derivatives with Higher Antibacterial Efficacy Based on the In-vitro and Density Functional Theory.

PubMed

Asiri, Abdullah M; Khan, Salman A; Al-Thaqafy, Saad H; Sharma, Kamlesh

2015-05-01

Series of cyano substituted isoquinoline dyes were synthesized by one-pot multicomponent reactions (MCRs) of aldehydes, malononitrile, 6-methoxy-1,2,3,4-tetrahydro-naphthalin-1-one and ammonium acetate. Results obtained from spectroscopic (FT-IR, (1)H-NMR, (13)C-NMR, EI-MS) and elemental analysis of synthesized compounds was in agreement with their chemical structures. Structure of the compound was further conformed by X-ray crystallographic. UV-vis and fluorescence spectroscopy measurements provided that all compounds are good absorbent and fluorescent. Fluorescence polarity study demonstrated that these compounds were sensitive to the polarity of the microenvironment provided by different solvents. In addition, spectroscopic and physicochemical parameters, including electronic absorption, extenction coefficient, Stokes shift, oscillator strength transition dipole moment and fluorescence quantum yield were investigated in order to explore the analytical potential of synthesized compounds. The anti-bacterial activity of these compounds were first studied in vitro by the disk diffusion assay against two Gram-positive and two Gram-negative bacteria. The minimum inhibitory concentration was then determined with the reference of standard drug chloramphenicol. The results displayed that compound 3 was better inhibitors of both types of the bacteria (Gram-positive and Gram-negative) than chloramphenicol. Furthermore, quantum chemistry calculations using DFT/6-31-G* level of theory confirm the results. Dipole moment and frontier molecular orbitals were also investigated.

Imidazopyridines as a source of biological activity and their pharmacological potentials-Infrared and Raman spectroscopic evidence of their content in pharmaceuticals and plant materials.

PubMed

Dymińska, Lucyna

2015-09-15

Derivatives of imidazopyridine are used in medicinal chemistry due to their biological and pharmaceutical properties. This review article presents imidazopyridine pharmacological activity as antiinflammatory, anticancer, antiviral, antiosteoporotic, antiparasitic, and antihypertensive agents by studying its various synthesized derivatives. Some of compounds with imidazopyridine skeleton are used in psychiatry and autoimmune disorders. The presented data suggest that IR and Raman spectra measurements are a good methods for identification and characterization of the compounds containing imidazopyridine core. Two stretching vibrations: νas(Φ) and νs(Φ) are of a diagnostic importance. The appearance of these bands in the IR and Raman spectra of some plants, tissues and pharmaceuticals confirms the presence of imidazopyridine skeleton in these substances. Copyright © 2015 Elsevier Ltd. All rights reserved.

Synthesis: Small library of hybrid scaffolds of benzothiazole having hydrazone and evaluation of their β-glucuronidase activity.

PubMed

Taha, Muhammad; Arbin, Mastura; Ahmat, Norizan; Imran, Syahrul; Rahim, Fazal

2018-04-01

Due to the great biological importance of β-glucuronidase inhibitors, here in this study, we have synthesized a library of novel benzothiazole derivatives (1-30), characterized by different spectroscopic methods and evaluated for β-glucuronidase inhibitory potential. Among the series sixteen compounds i.e.1-6, 8, 9, 11, 14, 15, 20-23 and 26 showed outstanding inhibitory potential with IC 50 value ranging in between 16.50 ± 0.26 and 59.45 ± 1.12 when compared with standard d-Saccharic acid 1,4-lactone (48.4 ± 1.25 µM). Except compound 8 and 23 all active analogs showed better potential than the standard. Structure activity relationship has been established. Copyright © 2018 Elsevier Inc. All rights reserved.

Diorganotin(IV) complexes of biologically potent 4(3H)-quinazolinone derived Schiff bases: synthesis, spectroscopic characterization, DNA interaction studies and antimicrobial activity.

PubMed

Prasad, Kollur Shiva; Kumar, Linganna Shiva; Chandan, Shivamallu; Jayalakshmi, Basvegowda; Revanasiddappa, Hosakere D

2011-10-15

Four Schiff base ligands and their corresponding organotin(IV) complexes have been synthesized and characterized by elemental analyses, IR, (1)H NMR, MS and thermal studies. The Schiff bases are obtained by the condensation of 3-amino-2-methyl-4(3H)-quinazolinone with different substituted aldehydes. The elemental analysis data suggest the stoichiometry to be 1:1 ratio formation. Infrared spectral data agreed with the coordination to the central metal ion through imine nitrogen, lactam oxygen and deprotonated phenolic oxygen atoms. All the synthesized compounds have been evaluated for antimicrobial activity against selected species of microorganisms. In addition, DNA binding/cleavage capacity of the compounds was analyzed by absorption spectroscopy, viscosity measurements and gel electrophoresis methods. Copyright © 2011 Elsevier B.V. All rights reserved.

Activity-guided isolation of the chemical constituents of Muntingia calabura using a quinone reductase induction assay.

PubMed

Su, Bao-Ning; Jung Park, Eun; Vigo, Jose Schunke; Graham, James G; Cabieses, Fernando; Fong, Harry H S; Pezzuto, John M; Kinghorn, A Douglas

2003-06-01

Activity-guided fractionation of an EtOAc-soluble extract of the leaves of Muntingia calabura collected in Peru, using an in vitro quinone reductase induction assay with cultured Hepa 1c1c7 (mouse hepatoma) cells, resulted in the isolation of a flavanone with an unsubstituted B-ring, (2R,3R)-7-methoxy-3,5,8-trihydroxyflavanone (5), as well as 24 known compounds, which were mainly flavanones and flavones. The structure including absolute stereochemistry of compound 5 was determined by spectroscopic (HRMS, 1D and 2D NMR, and CD spectra) methods. Of the isolates obtained, in addition to 5, (2S)-5-hydroxy-7-methoxyflavanone, 2',4'-dihydroxychalcone, 4,2',4'-trihydroxychalcone, 7-hydroxyisoflavone and 7,3',4'-trimethoxyisoflavone were found to induce quinone reductase activity.

A dihydrochalcone derivative and further steroidal saponins from Sansevieria trifasciata Prain.

PubMed

Tchegnitegni, Billy T; Teponno, Rémy B; Jenett-Siems, Kristina; Melzig, Matthias F; Miyamoto, Tomofumi; Tapondjou, Léon A

2017-10-26

Phytochemical investigation of the aerial parts of Sansevieria trifasciata, one of the most common Dracaenaceae plants, has resulted in the isolation of a new dihydrochalcone derivative named trifasciatine C (1), four previously unreported steroidal saponins as two pairs of inseparable regioisomers: trifasciatosides K/L (2/3), M/N (4/5), together with the known 1,2-(dipalmitoyl)-3-O-β-D-galactopyranosylglycerol (6), aconitic acid (7), and 1-methyl aconitic acid (8). Their structures were elucidated mainly by extensive spectroscopic analysis (1D and 2D nuclear magnetic resonance) and high-resolution electronspray ionization-mass spectrometry, as well as chemical methods and comparison of their spectral data with those of related compounds. Compounds 2/3 and 4/5 were evaluated for their antiproliferative activity on Hela cells, and no significant effect was observed.

Spectroscopic studies of the intramolecular hydrogen bonding in o-hydroxy Schiff bases, derived from diaminomaleonitrile, and their deprotonation reaction products.

PubMed

Szady-Chełmieniecka, Anna; Kołodziej, Beata; Morawiak, Maja; Kamieński, Bohdan; Schilf, Wojciech

2018-01-15

The structural study of five Schiff bases derived from diaminomaleonitrile (DAMN) and 2-hydroxy carbonyl compounds was performed using 1 H, 13 C and 15 N NMR methods in solution and in the solid state as well. ATR-FTIR and X-Ray spectroscopies were used for confirmation of the results obtained by NMR method. The imine obtained from DAMN and benzaldehyde was synthesized as a model compound which lacks intramolecular hydrogen bond. Deprotonation of all synthesized compounds was done by treating with tetramethylguanidine (TMG). NMR data revealed that salicylidene Schiff bases in DMSO solution exist as OH forms without intramolecular hydrogen bonds and independent on the substituents in aromatic ring. In the case of 2-hydroxy naphthyl derivative, the OH proton is engaged into weak intramolecular hydrogen bond. Two of imines (salDAMN and 5-BrsalDAMN) exist in DMSO solution as equilibrium mixtures of two isomers (A and B). The structures of equilibrium mixture in the solid state have been studied by NMR, ATR-FTIR and X-Ray methods. The deprotonation of three studied compounds (salDAMN, 5-BrsalDAMN, and 5-CH 3 salDAMN) proceeded in two different ways: deprotonation of oxygen atom (X form) or of nitrogen atom of free primary amine group of DAMN moiety (Y form). For 5-NO 2 salDAMN and naphDAMN only one form (X) was observed. Copyright © 2017 Elsevier B.V. All rights reserved.

Detection of mercury ions using L-cysteine modified electrodes by anodic stripping voltammetric method

NASA Astrophysics Data System (ADS)

Vanitha, M.; Balasubramanian, N.; Joni, I. Made; Panatarani, Camellia

2018-02-01

The detection of contaminants in wastewater is of massive importance in today's situation as they pose a serious threat to the environment as well as humans. One such vital contaminants is mercury and its compound, the reported mercury detectors grieve from low sensitivity, high cost and slow response. In the present work graphene based electrode material is developed for sensing mercury contaminants in wastewater using electrochemical technique. The synthesized material graphene oxide (GO) modified with L-Cysteine in presence of polyvinylpyrrolidone (PVP) as capping agent was characterized using SEM, TEM and Raman Spectroscopic analysis. It is ascertained from the morphological characterization that the nanocomposite exhibits a spherical morphology. The L-cysteine modified graphene oxide electrode is electrochemically characterized using redox couple [Fe(CN)63-/4-] and electrochemical impedance spectroscopic (EIS) analysis. Electrochemical sensing of Hg (II) ions in solution was done using Square wave anodic stripping voltammetry (SWASV). The incorporation of graphene significantly increases the sensitivity and selectivity towards mercury sensing.

Chemical constituents of Piper betle Linn. (Piperaceae) roots.

PubMed

Ghosh, K; Bhattacharya, T K

2005-08-31

Column chromatography of the alcoholic extract of Piper betle roots furnished aristololactam A-II and a new phenyl propene, characterized as 4-allyl resorcinol, while the petroleum-ether extract yielded a diketosteroid, viz. stigmast-4-en-3,6-dione. All these compounds were characterized by spectroscopic means. Isolation of these compounds from this source is being reported here for the first time.

α-Glucosidase inhibitory hydrolyzable tannins from Eugenia jambolana seeds.

PubMed

Omar, Raed; Li, Liya; Yuan, Tao; Seeram, Navindra P

2012-08-24

Three new hydrolyzable tannins including two gallotannins, jamutannins A (1) and B (2), and an ellagitannin, iso-oenothein C (3), along with eight known phenolic compounds were isolated from the seeds of Eugenia jambolana fruit. The structures were elucidated on the basis of spectroscopic data analysis. All compounds isolated were evaluated for α-glucosidase inhibitory effects compared to the clinical drug acarbose.

Study of a series of cobalt(II) sulfonamide complexes: Synthesis, spectroscopic characterization, and microbiological evaluation against M. tuberculosis. Crystal structure of [Co(sulfamethoxazole)2(H2O)2]·H2O

NASA Astrophysics Data System (ADS)

Mondelli, Melina; Pavan, Fernando; de Souza, Paula C.; Leite, Clarice Q.; Ellena, Javier; Nascimento, Otaciro R.; Facchin, Gianella; Torre, María H.

2013-03-01

Nowadays, the research for new and better antimicrobial compounds is an important field due to the increase of immunocompromised patients, the use of invasive medical procedures and extensive surgeries, among others, that can affect the incidence of infections. Another big problem associated is the occurrence of drug-resistant microbial strains that impels a ceaseless search for new antimicrobial agents. In this context, a series of heterocyclic-sulfonamide complexes with Co(II) was synthesized and characterized with the aim of obtaining new antimicrobial compounds. The structural characterization was performed using different spectroscopic methods (UV-Vis, IR, and EPR). In spite of the fact that the general stoichiometry for all the complexes was Co(sulfonamide)2·nH2O, the coordination atoms were different depending on the coordinated sulfonamide. The crystal structure of [Co(sulfamethoxazole)2(H2O)2]·H2O was obtained by X-ray diffraction showing that Co(II) is in a slightly tetragonal distorted octahedron where sulfamethoxazole molecules act as a head-to-tail bridges between two cobalt atoms, forming polymeric chains. Besides, the activity against Mycobacterium tuberculosis, one of the responsible for tuberculosis, and the cytotoxicity on J774A.1 macrophage cells were evaluated.

Synthesis, spectroscopic characterization, theoretical study and anti-hepatic cancer activity study of 4-(1E,3Z,6E)-3-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-5-oxohepta-1,3,6-trien-1-yl)-2-methoxyphenyl 4-nitrobenzoate, a novel curcumin congener

NASA Astrophysics Data System (ADS)

Srivastava, Sangeeta; Gupta, Preeti; Singh, Ranvijay Pratap; Jafri, Asif; Arshad, M.; Banerjee, Monisha

2017-08-01

In the present work 4-(1E,3Z,6E)-3-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-5-oxohepta-1,3,6-trien-1-yl)-2-methoxyphenyl 4-nitrobenzoate (2), a novel curcumin ester was synthesized. The molecular structure and spectroscopic analysis were performed using experimental techniques like FT-IR, 1H,13C NMR, mass and UV-visible as well as theoretical calculations. The theoretical calculations were done by DFT level of theory using B3LYP/6-31G (d,p) basis set. The vibrational wavenumbers were calculated using DFT method and assigned with the help of potential energy distribution (PED). The electronic properties such as frontier orbitals and band gap energies have been calculated using time dependent density functional theory (TD-DFT). The strength and nature of weak intramolecular interactions have been studied by AIM approach. Global and local reactivity descriptors have been computed to predict reactivity and reactive sites in the molecule. First hyperpolarizability values have been calculated to describe the nonlinear optical (NLO) property of the synthesized compounds. Molecular electrostatic potential (MEP) analysis has also been carried out. The anti-hepatic cancer activity of compound 2 was also carried out.

Synthesis and Electrochemistry of Cyclopentadienylcarbonyliron Tetramer: An Advanced Experiment.

ERIC Educational Resources Information Center

White, A. J.; Cunningham, Alice J.

1980-01-01

Describes an advanced level experiment in which a transition metal cluster compound, cyclopentadienylcarbonyliron tetramer, is synthesized and characterized spectroscopically. Its redox properties are then explored through cyclic voltammetry. (CS)

[Chemical constituents from involatile moiety of Pogostemon cablin].

PubMed

Huang, Liejun; Mu, Shuzhen; Zhang, Jianxin; Deng, Bin; Song, Zhiqin; Hao, Xiaojiang

2009-02-01

To study the chemical constituents of involatile moiety of Pogostemon cablin. Compounds were isolated and purified by repeated column chromatography, and their structures were elucidated by spectroscopic analysis. Nine compounds have been isolated and identified: epifriedelinol (1), 5-hydroxymethol-2-furfural (2), succinic acid (3), beta-sitosterol (4), daucosterol (5), crenatoside (6), 3'''-O-methylcrenatoside (7), isocrenatoside (8), and apigenin-7-O-beta-D-(6"-p-coumaryl)-glucoside (9). Compounds 2, 3, 6-8 were isolated from Pogostemon genus for the first time.

[Study on the chemical constituents from Clematis brevicaudata].

PubMed

Yang, Ai-Mei; Du, Jing; Miao, Zhong-Huan; Yuan, Hui-Jun

2009-10-01

To study the chemical constituents from Clematis brevicaudata. The compounds were isolated by column chromatography and their structures were elucidated through spectroscopic analysis (NMR). Eight compounds were isolated and identified as: palmitic acid (1), 1-docosanol (2), pentacosanoic acid-2', 3'-dihydroxypropyl ester (3), beta-sitosterol (4), daucosterol (5), a mixture of the trans-p-coumarate of the n-alkanols (6), 3,4-dihydroxy-trans coumatate ethyl ester (7), syringaresinol-O-D-glucopyranoside (8). All these compounds are obtained from Clematis brevicaudata for the first time.

New furanones from the plant endophytic fungus Pestalotiopsis besseyi.

PubMed

Liu, Haitao; Liu, Shuchun; Guo, Liangdong; Zhang, Yonggang; Cui, Langjun; Ding, Gang

2012-11-27

Pestalafuranones A-E (compounds 1-5), five new 2(5H)-furanones, have been isolated from cultures of an isolate of Pestalotiopsis besseyi. The structures of these compounds were elucidated mainly by analysis of their NMR spectroscopic data and HRESIMS experiments. Pestalafuranones A-C (compounds 1-3) displayed weak inhibitory effects against HIV-1 replication in C8166 cells, whereas pestalafuranones D (4) and E (5) showed moderate antifungal activity against the plant pathogens Verticillium dahiae and Alternaria longipes.

Metabolites of the endophytic fungus Penicillium sp. FJ-1 of Acanthus ilicifolius.

PubMed

Liu, Jian-Fang; Chen, Wei-Jie; Xin, Ben-Ru; Lu, Jie

2014-06-01

Two new compounds, named as (2R,3S)-pinobanksin-3-cinnamate (1), and 15alpha-hydroxy-(22E,24R)-ergosta-3,5,8(14),22-tetraen-7-one (2), were isolated from the endophytic fungus Penicillium sp. FJ-1 of Acanthus ilicifolius Linn. Their structures were elucidated on the basis of spectroscopic analysis. Additionally, compound 1 exhibited potent neuroprotective effects on corticosterone-damaged PC12 cells, and compound 2 showed potent cytotoxicity on glioma cell lines.

Pyrrole alkaloids from the fruits of Morus alba.

PubMed

Kim, Seon Beom; Chang, Bo Yoon; Hwang, Bang Yeon; Kim, Sung Yeon; Lee, Mi Kyeong

2014-12-15

Phytochemical investigation of the fruits of Morus alba afforded seventeen pyrrole alkaloids including five new compounds. The structures of five new pyrrole alkaloids, named morroles B-F (4, 5, 7, 16 and 17), were determined on the basis of spectroscopic interpretations. 4-[Formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]butanoate (2) was synthesized by chemical reaction but first isolated from nature. Among isolated compounds, compounds 6 and 14 significantly inhibited pancreatic lipase activity. Copyright © 2014 Elsevier Ltd. All rights reserved.

Three new aaptamine derivatives from the South China Sea sponge Aaptos aaptos.

PubMed

Gan, Jian-Hong; Hu, Wen-Zhen; Yu, Hao-Bing; Yang, Fan; Cao, Meng-Xue; Shi, Hua-Jin; Kang, Yong-Feng; Han, Bing-Nan

2015-01-01

Three new aaptamine derivatives (1-3), together with six known related compounds (4-9), have been isolated from the South China Sea sponge Aaptos aaptos. The structures of all compounds were unambiguously elucidated on the basis of spectroscopic analyses. Compounds 1, 4, 5, 7, and 9 showed cytotoxic activities against HeLa, K562, MCF-7, and U937 cell lines with IC50 values in the range of 0.90-12.32 μM.

New steroids from Anemarrhena asphodeloides rhizome and their α-glucosidase inhibitory activity.

PubMed

Khang, Pham Van; Phuong, Dao Mai; Ma, Lei

2017-05-01

Two new steroids were isolated from acid hydrolysis residue of the rhizomes of Anemarrhena asphodeloides. Their structures were identified on the basis of several spectroscopic analysis approaches including 1D, 2D-NMR techniques, and MS data, and by the comparison of spectral data of the known compounds. The biological activities of these two isolated compounds were explored on α-glucosidase. Compound 1 displayed 4.7 folds inhibitory activity against α-glucosidase compared with the positive control acarbose.

Isolation and biological evaluation of jatrophane diterpenoids from Euphorbia dendroides.

PubMed

Aljancić, Ivana S; Pesić, Milica; Milosavljević, Slobodan M; Todorović, Nina M; Jadranin, Milka; Milosavljević, Goran; Povrenović, Dragan; Banković, Jasna; Tanić, Nikola; Marković, Ivanka D; Ruzdijić, Sabera; Vajs, Vlatka E; Tesević, Vele V

2011-07-22

From the Montenegrin spurge Euphorbia dendroides, seven new diterpenoids [jatrophanes (1-6) and a tigliane (7)] were isolated and their structures elucidated by spectroscopic techniques. The biological activity of the new compounds was studied against four human cancer cell lines. The most effective jatrophane-type compound (2) and its structurally closely related derivative (1) were evaluated for their interactions with paclitaxel and doxorubicin using a multi-drug-resistant cancer cell line. Both compounds exerted a strong reversal potential resulting from inhibition of P-glycoprotein transport.

[One new chroman glycoside derivative from unmatured fruits of Citrus aurantium].

PubMed

Peng, Wen-Wen; Yan, He; Tan, Ning-Hua

2013-01-01

To study the chemical constituents of the unmatured fruits of Citrus aurantium. The AcOEt fraction of the methanol extracts of the unmatured fruits of C. aurantium were subjected on column chromatographies including silica gel, RP-18 and HPLC. Compound structures isolated were determined on the basis of spectroscopic data. Three compounds were isolated from the unmatured fruits of C. aurantium, which were identified as citrauranoside (1), limonexin (2) and limonin (3). Compound 1 is a new chroman glycoside derivative, named as citrauranoside.

Theoretical DFT, vibrational and NMR studies of benzimidazole and alkyl derivatives

NASA Astrophysics Data System (ADS)

Infante-Castillo, Ricardo; Rivera-Montalvo, Luis A.; Hernández-Rivera, Samuel P.

2008-04-01

Benzimidazoles are heterocyclic compounds that have awaked great interest during the last few years because of their proven biological activity as antiviral, antimicrobial, and antitumoral agents. For this reason, the development of a systematic FT-IR, FT-Raman and NMR study of 1-substituted compounds in 2-methylbenzimidazole constitutes a significant tool in understanding the molecular dynamics and the structural parameters that govern their behavior. Two new 1-alkyl-2-methylbenzimidazoles compounds were synthesized from reaction of 2-methylbenzimidazole with primary and secondary alkyl halides using a strong base as a catalyst. These compounds were purified and characterized by elemental analysis and different spectroscopic methods. The comparative analysis of vibrational modes of benzimidazole and its alkyl derivatives show that regions of absorption are very similar in all of them. However, changes are produced at low frequencies specifically in the C-H out of plane deformations, ring breathing and ring skeletal vibrations. The ring out-of plane bending modes shift by 10-15 cm -1 in some cases as results of alkyl substitution. The theoretical calculated spectra, using Density Functional Theory (DFT) approximation, and experimental results were consistent with each other. The GIAO method was used to calculate absolute shieldings, which agree consistently with those measured by 1H and 13C NMR. The consistency and efficiency of the GIAO 13C and 1H NMR calculations were thoroughly checked by the analysis of statistical parameters concerning computed and experimental 13C and 1H NMR chemical shift values of the studied compounds.

Application of HPLC and ESI-MS techniques in the analysis of phenolic acids and flavonoids from green leafy vegetables (GLVs).

PubMed

Kumar, B Ramesh

2017-12-01

Diets containing high proportions of fruits and vegetables reduce the risk of onset of chronic diseases. The role of herbal medicines in improving human health is gaining popularity over the years, which also increases the need for safety and efficiency of these products. Green leafy vegetables (GLVs) are the richest source of phenolic compounds with excellent antioxidant properties. Increased consumption of diets containing phenolic compounds may give positive and better results to human health and significantly improves the immune system. Highly selective, susceptible and versatile analytical techniques are necessary for extraction, identification, and quantification of phenolic compounds from plant extracts, which helps to utilize their important biological properties. Recent advances in the pre-treatment procedures, separation techniques and spectrometry methods are used for qualitative and quantitative analysis of phenolic compounds. The online coupling of liquid chromatography with mass spectrometry (LC-MS) has become a useful tool in the metabolic profiling of plant samples. In this review, the separation and identification of phenolic acids and flavonoids from GLVs by LC-MS have been discussed along with the general extraction procedures and other sources of mass spectrometer used. The review is devoted to the understanding of the structural configuration, nature and accumulation pattern of phenolic acids and flavonoids in plants and to highlighting the recent developments in the chemical investigation of these compounds by chromatographic and spectroscopic techniques. It concludes with the advantages of the combination of these two methods and prospects.

Chromocene in porous polystyrene: an example of organometallic chemistry in confined spaces.

PubMed

Estephane, Jane; Groppo, Elena; Vitillo, Jenny G; Damin, Alessandro; Lamberti, Carlo; Bordiga, Silvia; Zecchina, Adriano

2009-04-07

In this work, we present an innovative approach to investigate the structure and the reactivity of a molecularly dispersed organometallic compound. The poly(4-ethylstyrene-co-divinylbenzene) microporous system (PS) is used as "solid solvent" able to molecularly disperse CrCp2, allowing: (i) its full characterization by means of spectroscopic techniques; (ii) the pressure and temperature dependent study of its interaction towards simple molecules like CO freely diffusing through the pores; (iii) the accurate determination of the reaction enthalpies by both direct microcalorimetric measurements and by an indirect spectroscopic approach. The experimental results are compared with quantum-mechanical calculations adopting the DFT approximation with two different functionals (namely BP86 and B3-LYP), showing the limitations and the potentialities of DFT methods in predicting the properties of open shell systems. It is concluded that modern DFT methods are able to give a coherent view of the vibrational properties of the CrCp2 molecule (and of the complex formed upon CO adsorption) that well match the experimental results, while the energetic predictions should be taken with care as they are significantly dependent on the functionals used.

DOE Office of Scientific and Technical Information (OSTI.GOV)

Pacold, J. I.; Altman, A. B.; Donald, S B

Materials of interest for nuclear forensic science are often highly heterogeneous, containing complex mixtures of actinide compounds in a wide variety of matrices. Scanning transmission X-ray microscopy (STXM) is ideally suited to study such materials, as it can be used to chemically image specimens by acquiring X-ray absorption near-edge spectroscopy (XANES) data with 25 nm spatial resolution. In particular, STXM in the soft X-ray synchrotron radiation regime (approximately 120 – 2000 eV) can collect spectroscopic information from the actinides and light elements in a single experiment. Thus, STXM combines the chemical sensitivity of X-ray absorption spectroscopy with high spatial resolutionmore » in a single non-destructive characterization method. This report describes the application of STXM to a broad range of nuclear materials. Where possible, the spectroscopic images obtained by STXM are compared with information derived from other analytical methods, and used to make inferences about the process history of each material. STXM measurements can yield information including the morphology of a sample, “elemental maps” showing the spatial distribution of major chemical constituents, and XANES spectra from localized regions of a sample, which may show spatial variations in chemical composition.« less

Experimental and theoretical study of p-nitroacetanilide

NASA Astrophysics Data System (ADS)

Gnanasambandan, T.; Gunasekaran, S.; Seshadri, S.

2014-01-01

The spectroscopic properties of the p-nitroacetanilide (PNA) were examined by FT-IR, FT-Raman and UV-Vis techniques. FT-IR and FT-Raman spectra in solid state were observed in the region 4000-400 cm-1 and 3500-100 cm-1, respectively. The UV-Vis absorption spectrum of the compound that dissolved in ethanol was recorded in the range of 200-400 nm. The structural and spectroscopic data of the molecule in the ground state were calculated by using density functional theory (DFT) employing B3LYP methods with the 6-31G(d,p) and 6-311+G(d,p) basis sets. The geometry of the molecule was fully optimized, vibrational spectra were calculated and fundamental vibrations were assigned on the basis of the total energy distribution (TED) of the vibrational modes, calculated with scaled quantum mechanics (SQM) method. Thermodynamic properties like entropy, heat capacity and enthalpy have been calculated for the molecule. HOMO-LUMO energy gap has been calculated. The intramolecular contacts have been interpreted using natural bond orbital (NBO) and natural localized molecular orbital (NLMO) analysis. Important non-linear optical (NLO) properties such as electric dipole moment and first hyperpolarizability have been computed using B3LYP quantum chemical calculation.

Green synthesis, biological and spectroscopic study on the interaction of multi-component Mannich bases of imidazo[2,1-b]benzothiazoles with human serum albumin.

PubMed

Maddili, Swetha K; Yandrati, Leela Prasad; Siddam, Shakuntala; Kannekanti, Vijaya Kumar; Gandham, Himabindu

2017-11-01

A series of Mannich bases of imidazo[2, l-b]benzothiazoles were prepared through one-pot multi-component reaction in the presence of water as an eco-friendly solvent. All the synthesized compounds were confirmed from IR, 1 HNMR, 13 CNMR, and Mass spectroscopy. Evaluation of in vitro anti-inflammatory and anti-microbial activities of all the synthesized derivatives was further accomplished. These results clearly displayed that compound 6d exhibited outstanding anti-inflammatory activity with a percentage inhibition of 70.23% by membrane stabilization method whereas 67.54% at 100μgmL -1 by the albumin denaturation method, which is comparable to the standard Diclofenac. Further screening against five fungal species (C. albicans ATCC 76615, C. mycoderma, C. utilis, A. flavus, and B. yeast) along with four gram positive (Methicillin-resistant S. aureus N315 (MRSA), Staphylococcus aureus ATCC 6538, Bacillus subtilis ATCC 21216, and Micrococcus luteus ATCC 4698), and six Gram-negative bacterial strains (Escherichia coli DH52, Escherichia coli JM109, Salmonella dysenteriae, Pseudomonas aeruginosa ATCC 27853, Bacillus proteus ATCC13315 and Bacillus typhi) was carried out. These findings manifested that compound 7c displayed excellent antifungal efficacy while compound 7b revealed significant anti-microbial activity. In addition binding behaviour of compound 7b was investigated by binding study between calf thymus DNA and compound 7b by UV-Vis absorption spectroscopy and further research about HSA interactions was carried out. Copyright © 2017 Elsevier B.V. All rights reserved.

Glucosides from Vitex agnus-castus.

PubMed

Kuruüzüm-Uz, Ayşe; Ströch, Karsten; Demirezer, L Omür; Zeeck, Axel

2003-08-01

The methanolic extract of the flowering stems of Vitex agnus-castus yielded three new iridoids: 6'-O-foliamenthoylmussaenosidic acid (agnucastoside A), 6'-O-(6,7-dihydrofoliamenthoyl)mussaenosidic acid (agnucastoside B) and 7-O-trans-p-coumaroyl-6'-O-trans-caffeoyl-8-epiloganic acid (agnucastoside C) in addition to four known iridoids (aucubin, agnuside, mussaenosidic acid and 6'-O-p-hydroxybenzoylmussaenosidic acid) and one known phenylbutanone glucoside (myzodendrone). The structure elucidations were mainly done by spectroscopic methods (1D and 2D NMR spectra) and MS data interpretation. The purified compounds were tested for biological activities against various microorganisms and cancer cell lines.

Two new triterpenoid saponins from the leaves of Bupleurum lancifolium (Apiaceae).

PubMed

Achouri, Amel; Derbré, Séverine; Medjroubi, Kamel; Laouer, Hocine; Séraphin, Denis; Akkal, Salah

2017-10-01

Chemical investigation of the leaves of Bupleurum lancifolium led to the isolation and identification of two triterpenoid saponins previously undescribed named 3-O-[α-L-rhamnopyranosyl (1 → 4)-β-D-glucopyranosyl] echinocystic acid 28-O-β-D-glucopyranosyl ester (1) and 3-O-[α-L-rhamnopyranosyl (1 → 4)-β-D-glucopyranosyl] oleanolic acid 28-O-β-D-glucopyranosyl ester (2) along with the two known compounds isorhamnetin 3-rutinoside (3) and rutin (4). Their structures were elucidated by different spectroscopic methods, including HRESIMS analysis as well as 1D and 2D NMR experiments.

Solution and solid-state structures of the monomeric, piano-stool mono(peralkylcyclopentadienyl)vanadium(IV) trihalides

DOE Office of Scientific and Technical Information (OSTI.GOV)

Hammer, M.S.; Messerle, L.

1990-05-02

The method recently reported by Herberhold and co-workers for the high-yield preparation of (C{sub 5}Me{sub 5})VX{sub 3} (X = Cl, Br or I) by direct halogenation of (C{sub 5}Me{sub 5})V(OCO){sub 4} has been reproduced by the authors. Spectroscopic and spectrometric data for the (C{sub 5}Me{sub 5}) and C{sub 5}Me{sub 4}Et compounds and the solid-state molecular structure of ({eta}-C{sub 5}Me{sub 4}Et)VCI{sub 3} are reported. 21 refs., 1 fig., 4 tabs.