Sesquiterpenoids from Vernonia cinerea.

PubMed

Chen, Xin; Zhan, Zha-Jun; Yue, Jian-Min

2006-01-01

A new sesquiterpenoid, namely vernocinolide A, as well as ten known ones, were isolated from the ethyl acetate soluble fraction of the Vernoniacinerea. The structure of vernocinolide A was elucidated by spectroscopic methods. Among the known sesquiterpenoids, nine of them were isolated from this plant for the first time.

Secondary metabolites of cyanobacteria Nostoc sp.

NASA Astrophysics Data System (ADS)

Kobayashi, Akio; Kajiyama, Shin-Ichiro

1998-03-01

Cyanobacteria attracted much attention recently because of their secondary metabolites with potent biological activities and unusual structures. This paper reviews some recent studies on the isolation, structural, elucidation and biological activities of the bioactive compounds from cyanobacteria Nostoc species.

Three new metabolites from Botrytis cinerea.

PubMed

Wang, Tian-Shan; Zhou, Jin-Yan; Tan, Hong

2008-01-01

Three new metabolites, gamma-abscisolactone (1), botrytisic acids A (3) and B (4) were isolated from the fermentation broth of Botrytis cinerea TB-3-H8. Their structures were elucidated on the basis of MS, IR, UV, and NMR spectroscopic data. Compound 2 was isolated from natural resource for the first time. The structure of 1 was further confirmed by single-crystal X-ray diffraction (CCDC-265897).

A new spermidine macrocyclic alkaloid isolated from Gymnosporia arenicola leaf.

PubMed

da Silva, Gustavo; Martinho, Ana; Soengas, Raquel González; Duarte, Ana Paula; Serrano, Rita; Gomes, Elsa Teixeira; Silva, Olga

2015-10-01

The isolation and structural elucidation of a macrocyclic alkaloid, characterized by the presence of a 13-membered macrolactam ring containing a spermidine unit N-linked to a benzoyl group is hereby reported. The structure of this previously unknown spermidine alkaloid isolated from Gymnosporia arenicola (Celastraceae) leaves has been elucidated by (1)H and (13)C NMR spectroscopy (including bidimensional analysis) and further characterized by high-resolution mass spectrometry and polarimetry. A route for the biosynthesis of this new bioactive macrocycle is proposed and the cytotoxicity of the compound was evaluated against two ATCC cell lines - one normal-derived (MCF10A) and one cancer-derived cell line (MCF7) - using the MTT assay. The alkaloid revealed to be non-cytotoxic against both cell lines. The IC50 values from the cells were also determined. Copyright © 2015 Elsevier B.V. All rights reserved.

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.

[Studies on chemical constituents from roots of Craibiodendron henryi].

PubMed

Huang, Xiang-Zhong; Liu, Yue; Yu, Shi-Shan; Hu, You-Cai; Qu, Jing

2007-04-01

To study the chemical constituents from the roots of Craibiodendron henryi. Various chromatographic techniques were used to isolate and purify the constituents. The structures were elucidated by chemical evidence and spectral methods. Twelve compounds were isolated from the ethyl acetate soluble fraction of the 95% ethanolic extract and their struc- tures were elucidated as quercetin (1), quercetin-3-O-rhamnicoside (2), quercetin-3-O-arabinofuranoside (3), (-)-epicatechin (4), proanthocyanidin A-2 (5), procyanidin B-2 (6), (-)-isolariciresinol-2a-O-beta-D-xylopyranoside (7), lyoniside (8), sitoster-yl-3beta-glucoside-6'-O-palmitate (9), beta-sitosterol (10), daucosterol (11) and octacosanoic acid (12). Compounds 1-12 were isolated from this plant for the first time.

[Studies on chemical constituents from Elaeocarpus sylvestris].

PubMed

Zhang, Hong-Chao; Shi, Hai-Ming

2008-10-01

To study the chemical constituents of Elaeocarpus sylvestris. The compounds were isolated by chromatographic methods and their structures were elucidated by physico-chemical properties and spectral analysis. Six compounds were isolated and identified as: 2-hydroxy-benzaldehyde (1), coniferyl alcohol (2), umbelliferone (3), scopoletin (4), beta-sitosterol (5), daucosterol (6). All above compounds are isolated from Elaeocarpus Genus for the first time.

Antioxidant activities of phenolic compounds isolated from the leaves of Macaranga allorobinsonii Whitmore

NASA Astrophysics Data System (ADS)

Darmawan, Akhmad; Fajriah, Sofa; Megawati, Dewijanti, Indah D.; Banjarnahor, Sofna; Yuliani, Tri; Hartati, Sri; Mozef, Tjandrawati; Effendi, Ruslan; Swandiny, Greesty F.

2017-01-01

Two secondary metabolites compounds, gallic acid (1) and methyl gallate (2) have been isolated from the ethyl acetate fraction of the methanol extract of the leaves of Macaranga allorobinsonii Whitmore. Isolation and purification of the secondary metabolite compounds conducted using chromatography methods, and structure elucidation determined based on NMR, mass spectroscopic data and compared with appropriate references.

Sesquiterpenoids from Vernonia cinerea.

PubMed

Chen, Xin; Zhan, Zha-Jun; Yue, Jian-Min

2006-02-01

A new sesquiterpenoid, vernocinolide A (1), as well as ten known ones (2-11), were isolated from the ethyl acetate soluble fraction of Vernonia cinerea. The structure of vernocinolide A (1) was elucidated by spectroscopic methods. Among the known sesquiterpenoids, nine of them were isolated from this plant for the first time.

Antioxidant capacities and anti-inflammatory effects of flavonoid compounds isolated from acai pulp (Euterpe oleracea Mart.)

USDA-ARS?s Scientific Manuscript database

Acai fruit (Euterpe oleracea Mart.) has been demonstrated to exhibit extremely high antioxidant capacity. Seven major flavonoids were isolated from freeze-dried acai pulp by various chromatographic methods. Their structures were elucidated as orientin (1), homoorientin (2), vitexin (3), luteolin (4)...

Antioxidant capacities of seven flavonoid compounds isolated from pulp of acai fruit (Euterpe oleracea)

USDA-ARS?s Scientific Manuscript database

The pulp of açai fruit (Euterpe oleracea Mart.) has been demonstrated to exhibit extremely high antioxidant capacity. Seven major flavonoids were isolated from freeze-dried acai pulp by various chromatographic methods. Their structures were elucidated as orientin (1), homoorientin (2), vitexin (3), ...

Sulfated phenolic compounds from Limonium caspium: Isolation, structural elucidation, and biological evaluation

USDA-ARS?s Scientific Manuscript database

Three new compounds, 5-methyldihydromyricetin (1), 5-methyldihydromyricetin-3'-O-sulfate (2) and ß-D-glucopyranoside, 3-methyl, but-3-en-1-yl 4-O-a-L-rhamnopyranosyl (3) have been isolated from the Limonium caspium, together with dihydromyricetin (4), dihydromyricetin-3'-O-sulfate (5), myricetin-3'-...

[Chemical constituents from the rhizoma of Arundina graminifolia].

PubMed

Liu, Mei-feng; Han, Yun; Xing, Dong-ming; Wang, Wei; Xu, Li-zhen; Du, Li-jun; Ding, Yi

2004-02-01

To isolate and elucidate the chemical constituents from the tuber of Arundina graminifolia. The compounds were extracted by 95% alcohol and isolated by column chromatography on silica gel, SephedaxLH-20 and ODS. The structures were determined by UV, IR, NMR and MS spectral analysis. Five compounds were isolated, and their structures were identified as (2E)-, 2-propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-decosyl ester (I), p-hydroxybenzyl alcohol (II), triacontanol (III) and p-hydroxybenzylethyl ether (IV), 3-hydroxy-5-methoxybibenzyl (V), respectively. All compounds were isolated from the genus of Arundina for the first time.

Structure elucidation of the new citharoxazole from the Mediterranean deep-sea sponge Latrunculia (Biannulata) citharistae.

PubMed

Genta-Jouve, Grégory; Francezon, Nellie; Puissant, Alexandre; Auberger, Patrick; Vacelet, Jean; Pérez, Thierry; Fontana, Angelo; Mourabit, Ali Al; Thomas, Olivier P

2011-08-01

Citharoxazole (1), a new batzelline derivative featuring a benzoxazole moiety, was isolated from the Mediterranean deep-sea sponge Latrunculia (Biannulata) citharistae Vacelet, 1969, together with the known batzelline C (2). This is the first chemical study of a Mediterranean Latrunculia species and the benzoxazole moiety is unprecedented for this family of marine natural products. The structure was mainly elucidated by the interpretation of NMR spectra and especially HMBC correlations. Copyright © 2011 John Wiley & Sons, Ltd.

[Studies on flavonoids of Oxytropis falcata].

PubMed

Lu, Fang; Xu, Xiao-Jie

2007-02-01

To investigate the flavonoids of Oxytropisfalcata. Compounds were isolated by column chromatography using silica gel, Sephadex LH -20 and ODS as the adsorbents. Their structures were elucidated by NMR and MS spectroscopic data. Eight compounds were isolated and elucidated as 2', 4'-dihydroxy-4-methoxy chalcone (1), 2', 4'-dihydroxy chalcone (2), 5,7-dihydroxy-4'-methoxy flavonol (3), 7-hydroxy-4'-methoxy flavanones (4), 3', 7-dihydroxy-2',4'-dimethoxy isoflavan (5), 2'-hydroxy-4'-methoxy chalcone (6), 2'-methoxy-4'-hydroxy chalcone (7), 2',4'-dihydroxy dihydrochalcone (8). All compounds were obtained from O. falcata for the first time.

Isolation of 8-hydroxyglycitein and 6-hydroxydaidzein from soybean miso.

PubMed

Hirota, Akira; Inaba, Miyuki; Chen, Yu-Chi; Abe, Naoki; Taki, Shoji; Yano, Masamichi; Kawaii, Satoru

2004-06-01

We isolated from soybean miso 8-hydroxyglycitein and 6-hydroxydaidzein as DPPH-radical scavengers, and elucidated their chemical structures by mass spectrometric, and (1)H- and (13)C-NMR spectrosopic analyses. These compounds showed DPPH-radical scavenging activity as high as that of alpha-tocopherol, 8-hydroxygenistein and 8-hydroxydaidzein. This is the first report of the isolation of 8-hydroxyglycitein from a natural source.

Two new flavonoids from Artemisa sacrorum Ledeb and their antifungal activity

NASA Astrophysics Data System (ADS)

Wang, Qing-Hu; Wu, Jie-si; Wu, Rong-jun; Han, Na-ren-chao-ke-tu; Dai, Na-yin-tai

2015-05-01

Two new flavonoids, named as sacriflavone A (1) and sacriflavone B (2), were isolated from the CHCl3 extract of Artemisa sacrorum Ledeb (A. sacrorum). The structures of the isolated compounds have been elucidated unambiguously by UV, MS, and a series of 1D and 2D NMR analyses. The isolated compounds exhibited antifungal activity against different Fusarium oxysporum f. sp. dianthi pathotypes.

[Studies on the chemical constituents of the fruit of Xylocarpus granatum].

PubMed

Cheng, Fan; Zhou, Yuan; Zou, Kun; Wu, Jun

2009-08-01

To study the chemical constituents of the fruit of Xylocarpus granatum. The chemical constituents were isolated by chromatographic methods and their structures were elucidated by NMR spectra and physicochemical properties. Ten compounds were isolated from the fruit of Xylocarpus granatum and the structures of them were identified as spicatin (1), xyloccensin K(2), 6-acetoxycedrodorin (3), aurantiamide acetate (4), (+)-catechin (5), alpha-tocopherol (6), abscisic acid (7), daucosterol (8), 4-hydroxybenzoic acid (9) and ethyl 3,4-dihydroxybenzoate (10). Compound 4 -10 are isolated from this plant for the first time.

Is the isolated ligand binding domain a good model of the domain in the native receptor?

PubMed

Deming, Dustin; Cheng, Qing; Jayaraman, Vasanthi

2003-05-16

Numerous studies have used the atomic level structure of the isolated ligand binding domain of the glutamate receptor to elucidate the agonist-induced activation and desensitization processes in this group of proteins. However, no study has demonstrated the structural equivalence of the isolated ligand binding fragments and the protein in the native receptor. In this report, using visible absorption spectroscopy we show that the electronic environment of the antagonist 6-cyano-7-nitro-2,3-dihydroxyquinoxaline is identical for the isolated protein and the native glutamate receptors expressed in cells. Our results hence establish that the local structure of the ligand binding site is the same in the two proteins and validate the detailed structure-function relationships that have been developed based on a comparison of the structure of the isolated ligand binding domain and electrophysiological consequences in the native receptor.

Isolation, Structural Modification, and HIV Inhibition of Pentacyclic Lupane-Type Triterpenoids from Cassine xylocarpa and Maytenus cuzcoina.

PubMed

Callies, Oliver; Bedoya, Luis M; Beltrán, Manuela; Muñoz, Alejandro; Calderón, Patricia Obregón; Osorio, Alex A; Jiménez, Ignacio A; Alcamí, José; Bazzocchi, Isabel L

2015-05-22

As a part of our investigation into new anti-HIV agents, we report herein the isolation, structure elucidation, and biological activity of six new (1-6) and 20 known (7-26) pentacyclic lupane-type triterpenoids from the stem of Cassine xylocarpa and root bark of Maytenus cuzcoina. Their stereostructures were elucidated on the basis of spectroscopic and spectrometric methods, including 1D and 2D NMR techniques. To gain a more complete understanding of the structural requirements for anti-HIV activity, derivatives 27-48 were prepared by chemical modification of the main secondary metabolites. Sixteen compounds from this series displayed inhibitory effects of human immunodeficiency virus type 1 replication with IC50 values in the micromolar range, highlighting compounds 12, 38, and 42 (IC50 4.08, 4.18, and 1.70 μM, respectively) as the most promising anti-HIV agents.

Methods for isolation of marine-derived endophytic fungi and their bioactive secondary products.

PubMed

Kjer, Julia; Debbab, Abdessamad; Aly, Amal H; Proksch, Peter

2010-03-01

Marine-derived fungi have been shown in recent years to produce a plethora of new bioactive secondary metabolites, some of them featuring new carbon frameworks hitherto unprecedented in nature. These compounds are of interest as new lead structures for medicine as well as for plant protection. The aim of this protocol is to give a detailed description of methods useful for the isolation and cultivation of fungi associated with various marine organisms (sponges, algae and mangrove plants) for the extraction, characterization and structure elucidation of biologically active secondary metabolites produced by these marine-derived endophytic fungi, and for the preliminary evaluation of their pharmacological properties based on rapid 'in house' screening systems. Some results exemplifying the positive outcomes of the protocol are given at the end. From sampling in marine environment to completion of the structure elucidation and bioactivity screening, a period of at least 3 months has to be scheduled.

Lanostane-Type Triterpenes from the Mushroom Astraeus pteridis with Antituberculosis Activity

USDA-ARS?s Scientific Manuscript database

Bioassay-guided fractionation of the EtOH extract of the Truffle-mimiking mushroom Astraeus pteridis led to the isolation and identification of three new (3-5) and two known (1, 2) lanostane triterpenes, and phenylalanine betaine (6). The structures of the isolates were elucidated based on 1D and 2D...

[Studies on chemical constitutents in roots of Jasminum sambac].

PubMed

Zhang, Zheng-fu; Bian, Bao-lin; Yang, Jian; Tian, Xiu-feng

2004-03-01

To isolate and identify the chemical constitutents in roots of Jasminum sambac. The compounds were isolated by means of chromatography and the structures were identified on the basis of physical and spectral data. Dotriacontanoic acid, dotriacontanol, oleanolic acid, daucosterol and hesperidin were elucidated. All compounds were found in this plant for the first time.

Two new diterpene phenols from Calocedrus decurrans

Treesearch

Sheeba Veluthoor; Shujun Li; Rick G. Kelsey; Marc C. Dolan; Nicholas A. Panella; Joe Karchesy

2010-01-01

Two new p-cymene based diphenols (1-2) were isolated from the heartwood of Calocedrus decurrans. Structures were elucidated by 1D and 2D NMR techniques and HRMS. Libocedroquinone (3) was also isolated as a natural product for the first time. A new system of nomenclature is proposed for description of such oligomeric p...

Isolation and Structure Elucidation of the Terpene "[beta]"-Thujone from Cedar Leaf Oil

ERIC Educational Resources Information Center

French, Larry G.

2011-01-01

Western red cedar leaf affords an essential oil characterized by high thujone content. Students in an advanced organic chemistry lab course isolate a single thujone diastereoisomer from commercially available cedar leaf oil. Treatment of crude oil, containing roughly 70% thujone, predominately as [alpha]-thujone (6.5:1), with ethanolic sodium…

Peloruside B, a Potent Antitumor Macrolide from the New Zealand Marine Sponge Mycale hentscheli: Isolation, Structure, Total Synthesis and Bioactivity

PubMed Central

Singh, A. Jonathan; Xu, Chun-Xiao; Xu, Xiaoming; West, Lyndon M.; Wilmes, Anja; Chan, Ariane; Hamel, Ernest; Miller, John H.; Northcote, Peter T.; Ghosh, Arun K.

2009-01-01

Peloruside B (2), a natural congener of peloruside A (1), was isolated in sub-milligram quantities from the New Zealand marine sponge Mycale hentscheli. Peloruside B promotes microtubule polymerization and arrests cells in the G2M phase of mitosis similar to paclitaxel, and its bioactivity was comparable to that of peloruside A. NMR-directed isolation, structure elucidation, structure confirmation by total synthesis and bioactivity of peloruside B are described in this article. The synthesis features Sharpless dihydroxylation, Brown's asymmetric allylboration reaction, reductive aldol coupling, Yamaguchi macrolactonization and selective methylation. PMID:19957922

[Study on triterpenes of Microtropis tiflora].

PubMed

Wang, Kui-wu; Hu, Xin-ling; Shen, Lian-qing; Pan, Yuan-jiang

2007-08-01

To study the chemical constituents of Microtropis triflora. The compounds were isolated by chromatography on silica gel and Sephadex LH-20. There structures were elucidatedby by chemical methods and spectral analysis. Five triterpenoids were isolated and elucidated as friedelin (1), 3-oxo-28-friedelanoic acid (2), 29-hydroxy-3-friedelanone (3), salaspermic acid (4), orthosphenic acid (5). Compounds 1-5 are all isolated from M. triflora for the first time.

[Isolation and structural elucidation of secondary metabolites from marine Streptomyces sp. SCSIO 1934].

PubMed

Niu, Siwen; Li, Sumei; Tian, Xinpeng; Hu, Tao; Ju, Jianhua; Ynag, Xiaohong; Zhang, Si; Zhang, Changsheng

2011-07-01

Marine Actinobacteria are emerging as new resources for bioactive natural products with promise in novel drug discovery. In recent years, the richness and diversity of marine Actinobacteria from the South China Sea and their ability in producing bioactive products have been investigated. The objective of this work is to isolate and identify bioactive secondary metabolites from a marine actinobacterium SCSIO 1934 derived from sediments of South China Sea. The strain was identified as a Streptomyces spieces by analyzing its 16S rDNA sequence. Streptomyces sp. SCSIO 1934 was fermented under optimized conditions and seven bioactive secondary metabolites were isolated and purified by chromatographic methods including colum chromatography over silica gel and Sephadex LH-20. Their structures were elucidated as 17-O-demethylgeldanamycin (1), lebstatin (2), 17-O-demethyllebstatin (3), nigericin (4), nigericin sodium salt (5), abierixin (6), respectively, by detailed NMR spectroscopic data (1H, 13C, COSY, HSQC and HMBC). This work provided a new marine actinobacterium Streptomyces sp. SCSIO 1934, capable of producing diverse bioactive natural products.

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.

New biflavonoids from dragon's blood of Dracaena cinnabari.

PubMed

Masaoud, M; Himmelreich, U; Ripperger, H; Adam, G

1995-08-01

The new biflavonoids 2'-methoxysocotrin-5'-ol, socotrin-4'-ol, and homoisosocotrin-4'-ol were isolated from dragon's blood of Dracaena cinnabari and their structures elucidated mainly by NMR spectroscopy.

Structure elucidation of nigricanoside A through enantioselective total synthesis† †Electronic supplementary information (ESI) available: Complete experimental details and characterization data. See DOI: 10.1039/c5sc00281h Click here for additional data file.

PubMed Central

Chen, Jie; Koswatta, Panduka; DeBergh, J. Robb; Fu, Peng; Pan, Ende

2015-01-01

Nigricanoside A was isolated from green alga, and its dimethyl ester was found to display potent cytotoxicity. Its scarcity prevented a full structure elucidation, leaving total synthesis as the only means to determine its relative and absolute stereochemistry and to explore its biological activity. Here we assign the stereochemistry of the natural product through enantioselective total synthesis and provide initial studies of its cytotoxicity. PMID:26877863

Hamacanthins A and B, new antifungal bis indole alkaloids from the deep-water marine sponge, Hamacantha sp.

PubMed

Gunasekera, S P; McCarthy, P J; Kelly-Borges, M

1994-10-01

Hamacanthin A [1] and hamacanthin B [2] are two bioactive dihydropyrazinonediylbis(indole) alkaloids isolated from a new species of deep-water marine sponge, Hamacantha sp. The hamacanthins are growth inhibitors of Candida albicans and Cryptococcus neoformans. Isolation and structure elucidation of 1 and 2 by nmr spectroscopy are described.

Discobahamins A and B, new peptides from the Bahamian deep water marine sponge Discodermia sp.

PubMed

Gunasekera, S P; Pomponi, S A; McCarthy, P J

1994-01-01

Discobahamin A [1] and discobahamin B [2] are two bioactive peptides isolated from a new species of the Bahamian deep water marine sponge Discodermia. The discobahamins are inhibitors of the growth of Candida albicans, and the isolation and structure elucidation of 1 and 2 by nmr and chemical methods is described.

Two new diterpene phenols from Calocedrus decurrans.

PubMed

Veluthoor, Sheeba; Li, Shujun; Kelsey, Rick G; Dolan, Marc C; Panella, Nicholas A; Karchesy, Joe

2010-04-01

Two new p-cymene based diphenols (1-2) were isolated from the heartwood of Calocedrus decurrans. Structures were elucidated by 1D and 2D NMR techniques and HRMS. Libocedroquinone (3) was also isolated as a natural product for the first time. A new system of nomenclature is proposed for description of such oligomeric p-cymene derivatives.

Isolation and structure of palstatin from the Amazon tree Hymeneae palustris(1).

PubMed

Pettit, George R; Meng, Yanhui; Stevenson, Clare A; Doubek, Dennis L; Knight, John C; Cichacz, Zbigniew; Pettit, Robin K; Chapuis, Jean-Charles; Schmidt, Jean M

2003-02-01

Bioassay (P388 lymphocytic leukemia cell line and human cancer cell lines) guided separation of an extract prepared from the leaves of Hymenaea palustris Ducké led to the isolation of six cancer cell growth inhibitory flavonoids (1-6). The structures were elucidated by HRMS and 1D and 2D NMR spectral analysis. The new flavonolignan 1 designated palstatin proved to be a methoxy structural modification of 5'-methoxyhydnocarpin-D (2). Flavones 1-4 inhibited growth of the pathogenic bacteria Enterococcus faecalis and/or Neisseria gonorrhoeae.

A Trachylobane Diterpenoid from Xylopia aethiopica

PubMed

Ngouela; Nyassé; Tsamo; Brochier; Morin

1998-02-27

A new trachylobane derivative identified as 7alpha-hydroxytrachyloban-19beta-oic acid (1) has been isolated from the bark of Xylopia aethiopica and its structure elucidated by various NMR techniques and molecular modeling.

A new triterpene from callus of Pterocarpus santalinus.

PubMed

Krishnaveni, K S; Srinivasa Rao, J V

2000-02-01

A new pentacyclic triterpene was isolated from the callus induced from the stem cuttings of Pterocarpus santalinus. Based on spectral methods, the structure of the new compound was elucidated as 3-ketooleanane (1).

[Study on the chemical constituents of the leaves of Ipomoea batatas].

PubMed

Lv, Ling-Yuz; Shi, Gao-Feng; Li, Chun-Lei; Han, Xue-Zhe; Lv, Qiu-Nan

2009-06-01

To study the chemical constituents of the leaves of Ipomoea batatas. The constituents were isolated and purified by silica gel and TLC, and their structures were elucidated by spectroscopy. Six compounds were isolated from 90% ethanol extract and identified as tetracosane (I ), myristic acid (II), beta-sitosterol (II), beta-carotene (IV), daucosterol (V) and quercetin (VI). Compounds I, II, IV, V are isolated from this plant for the first time.

Chemical constituents from aerial part of Curcuma wenyujin.

PubMed

Tao, Zheng-Ming; Li, Ying-Yu; Ji, Ping; Wang, Yu-Bo; Qin, Guo-Wei

2007-12-01

To investigate the chemical constituents from aerial part of Curcuma wenyujin. Compounds were isolated by repeated column chromatography on silica gel. Their structures were elucidated on the basis of spectral analysis and comparison with literature data. Six compounds were isolated and identified as codonolactone (1), voleneol (2), octacosanoic acid (3), beta-sitosterol (4), mangdesisterol (5), and daucosterol (6). Compounds 1, 2, and 5 were isolated from the plant for the first time.

[Studies on the chemical constituents of the root and rhizoma of Ligusticum jeholense].

PubMed

Zhang, Bo; Sun, Jia-Ming; Chang, Ren-Long; Zhang, Hui

2009-05-01

To study the chemical constituents of the root and rhizoma of Ligusticum jeholense. The constituents were isolated by silica gel column chromatography, Sephadex LH-20 column chromatography and their structures were elucidated through spectral analysis. Seven compounds were separated from the EtOH extracts. Their structures were identified as levistolide A (1), xiongterpene (2), linoleic acid (3), sucrose (4), daucosterol (5), ferulic acid (6) and beta-sitosterol (7). Compounds 1-5 are isolated from the genus for the first time.

Novel Isochroman Dimers from Stachybotrys sp. PH30583: Fermentation, Isolation, Structural Elucidation and Biological Activities.

PubMed

Li, Wei; Yang, Ya-Bin; Yang, Xue-Qiong; Xie, Hui-Ding; Shao, Zhi-Hui; Zhou, Hao; Miao, Cui-Ping; Zhao, Li-Xing; Ding, Zhong-Tao

2017-05-01

The rare anishidiol and five new isochromans, including three novel dimers with unprecedented skeletons, were isolated from Stachybotrys sp. PH30583. Their structures were determined by spectral analyses. The bioactivities of these compounds were also investigated. The dimers ( 6 - 10 ) inhibited acetylcholinesterase at 50 µM, but the monomers did not. To investigate the biogenesis of the novel dimers, a time-course investigation of metabolite production was undertaken. Georg Thieme Verlag KG Stuttgart · New York.

Isolation and structure elucidation of a new indole alkaloid from Rauvolfia serpentina hairy root culture: the first naturally occurring alkaloid of the raumacline group.

PubMed

Sheludko, Yuri; Gerasimenko, Irina; Kolshorn, Heinz; Stöckigt, Joachim

2002-05-01

A new monoterpenoid indole alkaloid, 10-hydroxy- N(alpha)-demethyl-19,20-dehydroraumacline ( 1), was isolated as a mixture of E- and Z-isomers from hairy root culture of Rauvolfia serpentina Benth. ex Kurz (Apocynaceae) and the structure was determined by 1D and 2D NMR analyses. The new indole alkaloid represents the first naturally occurring alkaloid of the raumacline group and its putative biosynthetical pathway is discussed.

A new 1,2-ethanedione benzofurane derivative from Tephrosia purpurea.

PubMed

Peng, Yan; Chen, Yinning; Gao, Chenghai; Yan, Tao; Cao, Wenhao; Huang, Riming

2014-01-01

A new 1,2-ethanedione benzofurane derivative, purpdione (1), was isolated from Tephrosia purpurea, together with seven known flavonoids, purpurenone (2), pongamol (3), ovalitenin A (4), karanjin (5), lanceolatin B (6), tachrosin (7) and villosinol (8). The new structure was elucidated based on the analysis of its spectroscopic data. The structures of the known compounds were identified by comparing their spectroscopic data with those reported in the literature. The isolates exhibited marginal ability to inhibit the settlement of barnacle (Balanus reticulatus).

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.

Isolation and structure determination of obyanamide, a novel cytotoxic cyclic depsipeptide from the marine cyanobacterium Lyngbya confervoides.

PubMed

Williams, Philip G; Yoshida, Wesley Y; Moore, Richard E; Paul, Valerie J

2002-01-01

Obyanamide (1) was isolated from a variety of the marine cyanobacterium Lyngbya confervoides collected in Saipan, Commonwealth of the Northern Mariana Islands. Gross structure elucidation of this novel cyclic depsipeptide relied on extensive application of 2D NMR techniques. The absolute stereochemistry was deduced by chiral chromatography of the hydrolysis products and comparison with authentic and synthetic standards. Obyanamide (1) was cytotoxic against KB cells with an IC(50) of 0.58 microg/mL.

An isoflavone from Pterocarpus santalinus.

PubMed

Krishnaveni, K S; Rao, J V

2000-03-01

A new isoflavone together with liquiritigenin and isoliquiritigenin has been isolated from the heartwood of Pterocarpus santalinus. Based on spectral methods, the structure of the new compound was elucidated as 6-hydroxy,7,2',4',5'-tetramethoxyisoflavone.

Lanostane-type triterpenes from the mushroom Astraeus pteridis with Antituberculosis Activity

Treesearch

Rita Stanikunaite; Mohamed Radwan; James M. Trappe; Frank Fronczek; Samir A. Ross

2008-01-01

Bioassay-guided fractionation of an EtOH extract of the truffle-mimiking mushroom Astraeus pteridis led to the isolation and identification of three new (3-5) and two known (1, 2) lanostane triterpenes and phenylalanine betaine (6). The structures of the isolates were elucidated on the basis of 1D and 2D NMR spectroscopic data, HRESIMS results, and X...

[Study on flavonoids from stem bark of Pongamia pinnata].

PubMed

Yin, Hao; Zhang, Si; Wu, Jun

2004-07-01

Seven flavonoids, pongaflavone (1), karanjin (2), pongapin (3), pongachromene (4), 3,7-Dimethoxy-3', 4'-methylenedioxyflavone (5), millettocalyxin C( 6), 3,3',4', 7-tetramethoxyflavone (7), were isolated from 50% EtOH syrup of the bark of Pongamia pinnata and structureal elucidated on the base of spectral data. Compound 6 was isolated for first time from the plant of the genus Pongamia.

Phenolic glycosides from sugar maple (Acer saccharum) bark.

PubMed

Yuan, Tao; Wan, Chunpeng; González-Sarrías, Antonio; Kandhi, Vamsikrishna; Cech, Nadja B; Seeram, Navindra P

2011-11-28

Four new phenolic glycosides, saccharumosides A-D (1-4), along with eight known phenolic glycosides, were isolated from the bark of sugar maple (Acer saccharum). The structures of 1-4 were elucidated on the basis of spectroscopic data analysis. All compounds isolated were evaluated for cytotoxicity effects against human colon tumorigenic (HCT-116 and Caco-2) and nontumorigenic (CCD-18Co) cell lines.

Five new amicoumacins isolated from a marine-derived bacterium Bacillus subtilis.

PubMed

Li, Yongxin; Xu, Ying; Liu, Lingli; Han, Zhuang; Lai, Pok Yui; Guo, Xiangrong; Zhang, Xixiang; Lin, Wenhan; Qian, Pei-Yuan

2012-02-01

Four novel amicoumacins, namely lipoamicoumacins A-D (1-4), and one new bacilosarcin analog (5) were isolated from culture broth of a marine-derived bacterium Bacillus subtilis, together with six known amicoumacins. Their structures were elucidated on the basis of extensive spectroscopic (2D NNR, IR, CD and MS) analysis and in comparison with data in literature.

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.

Diterpenoid alkaloids from the roots of Aconitum brachypodum Diels.

PubMed

Yang, Li-Guo; Zhang, Ying-Jie; Xie, Jia-Ying; Xia, Wei-Jun; Zhang, Hai-Yuan; Tang, Meng-Yun; Mei, Shuang-Xi; Cui, Tao; Wang, Jing-Kun; Zhu, Zhao-Yun

2016-09-01

A new diterpenoid alkaloid, named bullatine H (1), along with 10 known diterpenoid alkaloids were isolated from the roots of Aconitum brachypodum Diels (Ranunculaceae). The structure of 1 was elucidated by analysis of its spectroscopic data. It should be noted that compound 1 is the first example with 11, 13-dioxygenated denudatine-type diterpenoid alkaloid isolated from Aconitum brachypodum.

Nafuredin, a novel inhibitor of NADH-fumarate reductase, produced by Aspergillus niger FT-0554.

PubMed

Ui, H; Shiomi, K; Yamaguchi, Y; Masuma, R; Nagamitsu, T; Takano, D; Sunazuka, T; Namikoshi, M; Omura, S

2001-03-01

A novel compound, nafuredin, was isolated as an inhibitor of anaerobic electron transport (NADH-fumarate reductase). It was obtained from culture broth of Aspergillus niger FT-0554 isolated from a marine sponge. The structure was elucidated as an epoxy-delta-lactone with an attached methylated olefinic side chain on the basis of spectral analysis.

Salaramides A and B; two alpha-oxoamides isolated from the marine sponge Hippospongia sp. (Porifera, Dictyoceratida).

PubMed

Bensemhoun, Julia; Rudi, Amira; Kashman, Yoel; Gaydou, Emile M; Vacelet, Jean; Aknin, Maurice

2010-02-01

Two novel alpha-oxoamides, salaramide A (1) and its homologue salaramide B (2), were isolated from the Madagascar marine sponge, Hippospongia sp., collected in Salary Bay, north of Tulear. The structures of 1 and 2 were elucidated by interpretation of mass spectra, 1D and 2D NMR spectra, and confirmed by chemical transformation.

Characterization and structure elucidation of antibacterial compound of Streptomyces sp. ECR77 isolated from east coast of India.

PubMed

Thirumurugan, D; Vijayakumar, R

2015-05-01

Forty marine actinobacteria were isolated from the sediments of east coast (Bay of Bengal) region of Tamilnadu, India. Morphologically distinct colonies were primarily tested against fish pathogenic bacteria such as Vibrio cholerae, V. parahaemolyticus, V. alginolyticus, Pseudomonas fluorescens and Aeromonas hydrophila by cross-streak plate method. The secondary metabolites produced by the highly potential strain cultured on starch casein broth were extracted separately with various solvents such as alcohol, ethyl acetate, methanol, petroleum ether and chloroform. The antibacterial assay of the bioactive compounds was tested against the fish pathogenic bacteria by well diffusion method. Of the various solvents used, the ethyl acetate extract of the isolate had good antibacterial activity. The potential strain was identified as Streptomyces labedae by phenotypic, 16S rRNA gene sequence and phylogenetic analysis. Purification of the biologically active compounds by column chromatography led to isolation of 27 fractions. The biologically active fraction was re-chromatographed on a silica gel column to obtain a single active compound, namely N-isopentyltridecanamide. The structure of the compounds was elucidated on the basis of ultra violet, Fourier transform infrared and nuclear magnetic resonance spectra.

Recent progress in elucidating the structure, function and evolution of disease resistance genes in plants.

PubMed

Liu, Jinling; Liu, Xionglun; Dai, Liangying; Wang, Guoliang

2007-09-01

Plants employ multifaceted mechanisms to fight with numerous pathogens in nature. Resistance (R) genes are the most effective weapons against pathogen invasion since they can specifically recognize the corresponding pathogen effectors or associated protein(s) to activate plant immune responses at the site of infection. Up to date, over 70 R genes have been isolated from various plant species. Most R proteins contain conserved motifs such as nucleotide-binding site (NBS), leucine-rich repeat (LRR), Toll-interleukin-1 receptor domain (TIR, homologous to cytoplasmic domains of the Drosophila Toll protein and the mammalian interleukin-1 receptor), coiled-coil (CC) or leucine zipper (LZ) structure and protein kinase domain (PK). Recent results indicate that these domains play significant roles in R protein interactions with effector proteins from pathogens and in activating signal transduction pathways involved in innate immunity. This review highlights an overview of the recent progress in elucidating the structure, function and evolution of the isolated R genes in different plant-pathogen interaction systems.

Structural elucidation of a novel phosphoglycolipid isolated from six species of Halomonas.

PubMed

Giordano, Assunta; Vella, Filomena M; Romano, Ida; Gambacorta, Agata

2007-08-01

The structure of a new phosphoglycolipid from the halophilic Gram-negative bacteria Halomonas elongata ATCC 33173(T), Halomonas eurihalina ATCC 49336(T), Halomonas almeriensis CECT 7050(T), strain Sharm (AM238662), Halomonas halophila DSM 4770(T), and Halomonas salina ATCC 49509(T) was elucidated by NMR and mass spectroscopy studies. In all of the species examined, the polar lipid composition consisted of 1,2-diacylglycero-3-phosphorylethanolamine, 1,2-diacylglycero-3-phosphoryl-glycerol, bisphosphatidyl glycerol, and the new phosphoglycolipid PGL1. The structure of PGL1 was established to be (2-(alpha-D-glucopyranosyloxy)-3-hydroxy-propyl)-phosphatidyl diacylglycerol. C16:0;C18:1 and C16:0;C19:cyclopropane are the most abundant acyl chains linked to the phosphatidylglycerol moiety of each isolated PGL1. All of the species presenting the lipid PGL1 belong to Halomonas rRNA group 1, suggesting that the new phosphoglycolipid could be a chemotaxonomic marker of this phylogenetic group.

[Chemical constituents from Ajuga nipponensis].

PubMed

He, Gui-xia; Liang, Xiao-lan; Ouyang, Wen; Yi, Gang-qiang; Li, Yun-yao; Zhao, Jian-ping; Ikhlas, Khan

2013-12-01

To study the chemical constituents of Ajuga nipponensis. The chemical constituents were isolated by repeated silica gel column chromatography and their structures were elucidated by phyisochemical properties and spectral analysis. Ten compounds were isolated and identified as:hexadecanoic acid(1), ajuforrestin A(2), beta-sitosterol(3), acacetin(4), apigenin(5), ajugamacrin B(6), ursolic acid(7), beta-ecdysone(8), 8-acetylharpagide(9) and daucosterol(10). Compounds 1-7 and 10 are isolated from this plant for the first time.

[Chemical constituents from the aerial part of Stauntonia obovatifoliola Hayata subsp. urophylla].

PubMed

Peng, Xiao-bing; Gao, Wei-lue; Hu, Dong-qun; Ma, Fang-fang; Fu, Li-gang; Deng, Qian; Wei, Ying

2013-11-01

To study the chemical constituents of the aerial part of Stauntonia obovatifoliola. The chemical constituents of ethyl acetate fraction were isolated and purified by several chromatography. Their structures were elucidated by their physiochemical properties and spectral methods. Six known compounds were isolated and identified as lupeone(1), lupeol(2), stigmasterol(3),3beta-O-acetyloleanolic acid(4), resinone(5) and daucosterol(6). Compounds 1-6 are isolated from this plant for the first time.

Isolation of Secondary Metabolites from the Roots of Salix Babylonica

NASA Astrophysics Data System (ADS)

Singh, Harpreet; Raturi, Rakesh; Badoni, P. P.

2017-08-01

Chemical examination of ethanolic extract of Salix babylonica, root, led to isolation of 2-(Hydroxymethyl) phenyl β-D-glucopyranoside(1) and 2-[(benzoyloxy)methyl]-4-hydroxyphenyl β-D-glucopyranoside 3-Benzoate (2)with previously known compounds β-Sitosterol, kaempferol 7-O-glucoside andapigenin 7-O-galactoside. Compounds 1and 2 had been isolated for the first time from this plant. The structures of the compounds had been elucidated with the help of spectral and chemical studies.

2,3-Dihydrobiflavone from Ginkgo biloba.

PubMed

Krauze-Baranowska, M; Sowiński, P

1999-06-01

From the yellow leaves of Ginkgo biloba 2,3-dihydrosciadopitysin (5,5'',7''-trihydroxy-7,4',4'''-trimethoxy-3',8''-flavanone/flavone) was isolated as a mixture of two diastereomers. Its structure was elucidated employing 2D NMR techniques.

Mumic acids A-E: new diterpenoids from mumiyo.

PubMed

Kiren, Yuko; Nugroho, Alfarius Eko; Hirasawa, Yusuke; Shirota, Osamu; Bekenova, Myrzaim; Narbekovich, Narbekov Omorbay; Shapilova, Marina; Maeno, Hiromichi; Morita, Hiroshi

2014-01-01

Five new diterpenoids belonging to labdane and isopimarane skeletons, mumic acids A-E (1-5), have been isolated from mumiyo. Their structures and absolute configurations were elucidated on the basis of spectroscopic data and chemical derivatization.

Grasshopper ketone 3-O-primveroside from Sinocrassula indica.

PubMed

Xie, Hai-Hui; Yoshikawa, Masayuki

2012-01-01

A new megastigmane glycoside, grasshopper ketone 3-O-primveroside (1), was isolated from the methanolic extract of the whole herbs of Sinocrassula indica (Crassulaceae). Its structure was elucidated on the basis of spectral and chemical evidence.

Structure elucidation of organic compounds from natural sources using 1D and 2D NMR techniques

NASA Astrophysics Data System (ADS)

Topcu, Gulacti; Ulubelen, Ayhan

2007-05-01

In our continuing studies on Lamiaceae family plants including Salvia, Teucrium, Ajuga, Sideritis, Nepeta and Lavandula growing in Anatolia, many terpenoids, consisting of over 50 distinct triterpenoids and steroids, and over 200 diterpenoids, several sesterterpenoids and sesquiterpenoids along with many flavonoids and other phenolic compounds have been isolated. For Salvia species abietanes, for Teucrium and Ajuga species neo-clerodanes for Sideritis species ent-kaurane diterpenes are characteristic while nepetalactones are specific for Nepeta species. In this review article, only some interesting and different type of skeleton having constituents, namely rearranged, nor- or rare diterpenes, isolated from these species will be presented. For structure elucidation of these natural diterpenoids intensive one- and two-dimensional NMR techniques ( 1H, 13C, APT, DEPT, NOE/NOESY, 1H- 1H COSY, HETCOR, COLOC, HMQC/HSQC, HMBC, SINEPT) were used besides mass and some other spectroscopic methods.

Nine New Gingerols from the Rhizoma of Zingiber officinale and Their Cytotoxic Activities.

PubMed

Li, Zezhi; Wang, Yanzhi; Gao, MeiLing; Cui, Wanhua; Zeng, Mengnan; Cheng, Yongxian; Li, Juan

2018-02-02

Nine new gingerols, including three 6-oxo-shogaol derivatives [( Z )-6-oxo-[6]-shogaol ( 1 ), ( Z )-6-oxo-[8]-shogaol ( 2 ), ( Z )-6-oxo-[10]-shogaol ( 3 )], one 6-oxoparadol derivative [6-oxo-[6]-paradol ( 4 )], one isoshogaol derivative [( E )-[4]-isoshogaol ( 5 )], and four paradoldiene derivatives [(4 E ,6 Z )-[4]-paradoldiene ( 8 ), (4 E ,6 E )-[6]-paradoldiene ( 9 ), (4 E ,6 E )-[8]-paradoldiene ( 10 ), (4 E ,6 Z )-[8]-paradoldiene ( 11 )], together with eight known analogues, were isolated from the rhizoma of Zingiber officinale . Their structures were elucidated on the basis of spectroscopic data. It was noted that the isolation of 6-oxo-shogaol derivatives represents the first report of gingerols containing one 1,4-enedione motif. Their structures were elucidated on the basis of spectroscopic and HRESIMS data. All the new compounds were evaluated for their cytotoxic activities against human cancer cells (MCF-7, HepG-2, KYSE-150).

Structure elucidation of two triterpenoid saponins from rhizome of Anemone raddeana Regel.

PubMed

Lu, Jincai; Xu, Beibei; Gao, Song; Fan, Li; Zhang, Hongfen; Liu, Runxiang; Kodama, Hiroyuki

2009-09-01

Two new 27-hydroxy-oleanolic acid type triterpenoid saponins, raddeanoside 20 (1) and raddeanoside 21(2) were isolated from the rhizome of Anemone raddeana Regel. The structures of the two compounds were elucidated as 27-hydroxy-oleanolic acid 3-O-alpha-L-rhamnopyranosyl(1-->2) [beta-D-glucopyranosyl (1-->4)]-alpha-L-arabinopyranoside (1) and 3-O-alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranosyl-27-hydroxy-oleanolic acid 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranoside (2) on the basis of chemical and spectral evidence.

Antifungal diterpenes from Hypoestes serpens (Acanthaceae).

PubMed

Rasoamiaranjanahary, Lalao; Marston, Andrew; Guilet, David; Schenk, Kurt; Randimbivololona, Fanantenanirainy; Hostettmann, Kurt

2003-02-01

Two new diterpenes, fusicoserpenol A and dolabeserpenoic acid A, with antifungal activity, were isolated from leaves of Hypoestes serpens (Acanthaceae). Their structures were elucidated by means of spectrometric methods including 1D and 2D NMR experiments and MS analysis. X-ray crystallographic analysis confirmed the structure of fusicoserpenol A and established the relative configuration.

[Studies on chemical constituents of leaves of Psidium guajava].

PubMed

Fu, Huizheng; Luo, Yongming; Zhang, Dongming

2009-03-01

To study the chemical constituents of the leaves of Psidium guajava. The chemical constituents were isolated by column chromatography on silica gel, Sephadex LH-20 and MPLC. Their structures were elucidated on the basis of spectral analysis. Nine compounds were isolated from this plant, and the structure of them were identified as ursolic acid (1), 2alpha-hydroxyursolic acid (2), 2alpha-hydroxyoleanolic acid (3), morin-3-O-alpha-L-arabopyranoside (4), quercetin (5), hyperin (6), myricetin-3-O-beta-D-glucoside (7), quercetin-3-O-beta-D-glucuronopyranoside (8), 1-O-galloyl-beta-D-glucose (9). Compounds 3, 7-9 were isolated from this plant for the first time.

Phenolic glycosides with antimalarial activity from Grevillea "Poorinda Queen".

PubMed

Ovenden, Simon P B; Cobbe, Melanie; Kissell, Rebecca; Birrell, Geoffrey W; Chavchich, Marina; Edstein, Michael D

2011-01-28

In search of new antimalarial compounds, three new phenolic glycosides, robustasides E (1), F (2), and G (3), in addition to the known compounds robustaside D (4) and quercetin-7-O-[α-l-rhamnopyranosyl(1→6)-β-d-galactopyranoside] (5), were identified during chemical investigations of the MeOH extract from the leaves and twigs of Grevillea "Poorinda Queen". The chemical structures of the new compounds were elucidated through 2D NMR spectroscopy, while the absolute configuration of the sugar was elucidated through chemical degradation and comparison with an authentic standard. Discussed in detail are the isolation and structure elucidation of 1-3, as well as the associated in vitro anitmalarial activities for 1-5. Also discussed are the in vivo anitmalarial and in vitro cytotoxic activities for 1, 3, and 4.

[Studies on the chemical constituents of Buddleja albiflora (II)].

PubMed

Zhang, Hai-Ping; Tao, Liang

2010-06-01

To study the chemical constituents of Buddleja albiflora. The constituents were isolated by column chromatography and their structures were elucidated by spectroscopic analyses. seven compounds were isolated and identified as aucubin (1), catalpol (2), acteoside (3), martynoside (4), ursolicacid (5), daucosterol (6), beta-sitosterol-3-0-beta-D-(6'-0-palmitate) glucopyranosisde (7). All these compounds are obtained from Buddleja albiflora for the first time.

Discorhabdins S, T, and U, new cytotoxic pyrroloiminoquinones from a deep-water Caribbean sponge of the genus Batzella.

PubMed

Gunasekera, Sarath P; Zuleta, Ignacio A; Longley, Ross E; Wright, Amy E; Pomponi, Shirley A

2003-12-01

Discorhabdins S, T, and U (1-3), three new discorhabdin analogues, have been isolated from a deep-water marine sponge of the genus Batzella. These discorhabdin analogues showed in vitro cytotoxicity against PANC-1, P-388, and A-549 cell lines. The isolation and structure elucidation of discorhabdins S, T, and U are described.

Nature's Chiral Catalyst and Anti-Malarial Agent: Isolation and Structure Elucidation of Cinchonine and Quinine from "Cinchona calisaya"

ERIC Educational Resources Information Center

Carroll, Anne-Marie; Kavanagh, David J.; McGovern, Fiona P.; Reilly, Joe W.; Walsh, John J.

2012-01-01

Nature is a well-recognized source of compounds of interest, but access is often an issue. One pertinent example is the cinchona alkaloids from the bark of "Cinchona calisaya." In this experiment, students at the third-year undergraduate level undertake the selective isolation and characterization of two of the four main alkaloids present in the…

Germacrane-type sesquiterpenoids from the roots of Valeriana officinalis var. latifolia.

PubMed

Wang, Peng-Cheng; Ran, Xin-Hui; Chen, Rui; Luo, Huai-Rong; Liu, Yu-Qing; Zhou, Jun; Zhao, You-Xing

2010-09-24

Eight new germacrane-type sesquiterpenoids, volvalerenals A-E (2-6) and volvalerenic acids A-C (7-9), along with four known compounds, were isolated from a chloroform extract of the roots of Valeriana officinalis var. latifolia. The structures and relative configurations of 2-9 were elucidated on the basis of spectroscopic data interpretation. The effects of all compounds isolated on acetylcholinesterase were evaluated.

[Study on the chemical constituents in roots of Gentiana dahurica].

PubMed

Chen, Qian-Liang; Shi, Zhang-Yan; Zhang, Ya-Hui; Zheng, Jiang-Bin

2011-08-01

To systematically study the chemical constituents in the roots of Gentiana dahurica. Various column chromatographic techniques were used for isolation and purification. The structures were elucidated on the basis of spectral data (UV, IR, MS, NMR) and identified by comparing with the authentic substance. Seven compounds were isolated and identified as: roburic acid (1), oleanolic acid (2), beta-sitosterol (3), daucosterol (4), gentiopicroside(5), swertiamarine (6), sweroside (7). Compounds 1, 2 and 4 are isolated from this plant for the first time.

[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.

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.

Guajadial: an unusual meroterpenoid from guava leaves Psidium guajava.

PubMed

Yang, Xiao-Long; Hsieh, Kun-Lung; Liu, Ji-Kai

2007-11-22

Guajadial (1), a novel caryophyllene-based meroterpenoid, was isolated from the Leaves of Psidium guajava (guava). The structure and relative stereochemistry of guajadial (1) were elucidated by extensive spectroscopic analysis. A possible biosynthetic pathway for 1 was proposed.

Matteucens I-J, phenolics from the rhizomes of Matteuccia orientalis.

PubMed

Zhu, Ling-Juan; Song, Ying; Shao, Peng; Zhang, Xue; Yao, Xin-Sheng

2018-01-01

Two new phenolics, named matteucens I-J (1-2), were isolated from the 60% EtOH extract of the rhizomes of Matteuccia orientalis (HOOK.) TREV. Their structures were elucidated by means of extensive spectroscopic analysis (HRESIMS, NMR).

Structure elucidation of a novel oligosaccharide (Medalose) from camel milk

NASA Astrophysics Data System (ADS)

Gangwar, Lata; Singh, Rinku; Deepak, Desh

2018-02-01

Free oligosaccharides are the third most abundant solid component in milk after lactose and lipids. The study of milk oligosaccharides indicate that nutrients are not only benefits the infant's gut but also perform a number of other functions which include stimulation of growth, receptor analogues to inhibit binding of pathogens and substances that promote postnatal brain development. Surveys reveal that camel milk oligosaccharides possess varied biological activities that help in the treatment of diabetes, asthma, anaemia, piles and also a food supplement to milking mothers. In this research, camel milk was selected for its oligosaccharide contents, which was then processed by Kobata and Ginsburg method followed by the HPLC and CC techniques. Structure elucidation of isolated compound was done by the chemical degradation, chemical transformation and comparison of chemical shift of NMR data of natural and acetylated oligosaccharide structure reporter group theory, the 1H, 13C NMR, 2D-NMR (COSY, TOCSY and HSQC) techniques, and mass spectrometry. The structure was elucidated as under: MEDALOSE

Product ion isotopologue pattern: A tool to improve the reliability of elemental composition elucidations of unknown compounds in complex matrices.

PubMed

Kaufmann, A; Walker, S; Mol, G

2016-04-15

Elucidation of the elemental compositions of unknown compounds (e.g., in metabolomics) generally relies on the availability of accurate masses and isotopic ratios. This study focuses on the information provided by the abundance ratio within a product ion pair (monoisotopic versus the first isotopic peak) when isolating and fragmenting the first isotopic ion (first isotopic mass spectrum) of the precursor. This process relies on the capability of the quadrupole within the Q Orbitrap instrument to isolate a very narrow mass window. Selecting only the first isotopic peak (first isotopic mass spectrum) leads to the observation of a unique product ion pair. The lighter ion within such an isotopologue pair is monoisotopic, while the heavier ion contains a single carbon isotope. The observed abundance ratio is governed by the percentage of carbon atoms lost during the fragmentation and can be described by a hypergeometric distribution. The observed carbon isotopologue abundance ratio (product ion isotopologue pattern) gives reliable information regarding the percentage of carbon atoms lost in the fragmentation process. It therefore facilitates the elucidation of the involved precursor and product ions. Unlike conventional isotopic abundances, the product ion isotopologue pattern is hardly affected by isobaric interferences. Furthermore, the appearance of these pairs greatly aids in cleaning up a 'matrix-contaminated' product ion spectrum. The product ion isotopologue pattern is a valuable tool for structural elucidation. It increases confidence in results and permits structural elucidations for heavier ions. This tool is also very useful in elucidating the elemental composition of product ions. Such information is highly valued in the field of multi-residue analysis, where the accurate mass of product ions is required for the confirmation process. Copyright © 2016 John Wiley & Sons, Ltd. Copyright © 2016 John Wiley & Sons, Ltd.

Chemical constituents from Piper wallichii.

PubMed

Shi, Yan-Ni; Yang, Lian; Zhao, Jin-Hua; Shi, Yi-Ming; Qu, Yan; Zhu, Hong-Tao; Wang, Dong; Yang, Chong-Ren; Li, Xing-Cong; Xu, Min; Zhang, Ying-Jun

2015-01-01

Fifteen known compounds including four triterpenoids (1-4), one sterol (5), one diketopiperazine alkaloid (6) and nine phenolics (7-15) were isolated from the stems of Piper wallichii. Their structures were elucidated by means of spectroscopic analysis, and acidic hydrolysis in case of the 2-oxo-3β,19α,23-trihydroxyurs-12-en-28-oic acid β-D-glucopyranosyl ester (1). The structure of compound 1 was fully assigned by 1D and 2D NMR experiments for the first time. All isolates were tested for their antibacterial, antifungal, anti-inflammatory and antiplatelet aggregation bioactivities.

Ultrahigh-performance liquid chromatography-ion trap mass spectrometry characterization of the steroidal saponins of Dioscorea panthaica Prain et Burkill and its application for accelerating the isolation and structural elucidation of steroidal saponins.

PubMed

Wang, Weihao; Zhao, Ye; Jing, Wenguang; Zhang, Jun; Xiao, Hui; Zha, Qin; Liu, An

2015-03-01

Dioscorea panthaica is a traditional Chinese medicinal herb used in the treatment of various physiological conditions, including cardiovascular disease, gastropathy and hypertension. Steroidal saponins (SS) are the main active ingredients of this herb and have effects on myocardial ischemia and cancer. The phytochemical evaluation of SS is both time-consuming and laborious, and the isolation and structural determination steps can be especially demanding. For this reason, the development of new methods to accelerate the processes involved in the identification, isolation and structural elucidation of SS is highly desirable. In this study, a new ultrahigh performance liquid chromatography-ion trap mass spectrometry (UHPLC-IT/MS(n)) method has been developed for the identification of the SS in D. panthaica Prain et Burkill. Notably, the current method can distinguish between spirostanol and furostanol-type compounds based on the fragmentation patterns observed by electrospray ionization-ion trap mass spectrometry (ESI-IT/MS(n)) analysis. UHPLC-IT/MS(n) was used to conduct a detailed investigation of the number, structural class and order of the sugar moieties in the sugar chains of the SS present in D. panthaica. The established fragmentation features were used to analyze the compounds found in the 65% ethanol fraction of the water extracts of D. panthaica. Twenty-three SS were identified, including 11 potential new compounds and six groups of isomers. Two of these newly identified SS were selected as representative examples, and their chemical structures were confirmed by (1)H and (13)C NMR analyses. This newly developed UHPLC-IT/MS(n) method therefore allowed for the efficient identification, isolation and structural determination of the SS in D. panthaica. Copyright © 2015 Elsevier Inc. All rights reserved.

A new benzylisoquinoline alkaloid from Leontice altaica.

PubMed

Jenis, Janar; Nugroho, Alfarius Eko; Hashimoto, Akiyo; Deguchi, Jun; Hirasawa, Yusuke; Wong, Chin Piow; Kaneda, Toshio; Shirota, Osamu; Morita, Hiroshi

2015-02-01

A new benzylisoquinoline alkaloid, lincangenine-4-β-D-glucopyranoside (1), has been isolated from the roots of Leontice altaica, together with 5 known alkaloids. Its structure was elucidated on the basis of 1D and 2D NMR data, and chemical means.

A New Triterpenoidal from Vernonia cinerea.

PubMed

Misra, T N; Singh, R S; Srivastava, R; Pandey, H S; Prasad, C; Singh, S

1993-10-01

From the roots of VERNONIA CINEREA Less. (Compositae) a new triterpenoid has been isolated and characterised as 3beta-acetoxyurs-19-ene ( 1). A further constituent has been identified as lupeol acetate. Structure elucidation has been made with the help of spectral analyses.

Secoiridoid components from Jasminum grandiflorum.

PubMed

Sadhu, Samir Kumar; Khan, Md Sojib; Ohtsuki, Takashi; Ishibashi, Masami

2007-07-01

Secoiridoid glucosides, 2''-epifraxamoside and demethyl-2''-epifraxamoside, and the secoiridoid, jasminanhydride were isolated from Jasminum grandiflorum together with four previously known phenolics and a triterpene. Structures were elucidated by detailed spectroscopic analysis. Stereochemistry of the compounds was determined by differential NOE experiment.

Two new C19-diterpenoid alkaloids from Aconitum tsaii.

PubMed

Li, Gui-Qiong; Zhang, Li-Mei; Zhao, Da-Ke; Chen, Yan-Ping; Shen, Yong

2017-05-01

Two new C 19 -diterpenoid alkaloids, 14-benzoylliljestrandisine (1) and 14-anisoylliljestrandisine (2), were isolated from the roots of Aconitum tsaii. Their structures were elucidated by different spectroscopic (IR, UV, 1D and 2D NMR) and mass-spectrometric techniques.

Constituents of Andromeda polifolia.

PubMed

Pachaly, P; Klein, M

1987-10-01

A reinvestigation of the aerial parts of ANDROMEDA POLIFOLIA afforded in addition to the known compounds gardenoside ( 1), guaijaverine ( 2) and avicularine ( 3), a new flavonol-dipentoside named polifolioside ( 4). the compounds were isolated employing DCCC and their structures were elucidated by spectroscopic methods.

One new benzyldihydrophenanthrene from Arundina graminifolia.

PubMed

Liu, Mei-Feng; Han, Yun; Xing, Dong-Ming; Wang, Wei; Xu, Li-Zhen; Du, Li-Jun; Ding, Yi

2005-10-01

A novel benzyldihydrophenanthrene named arundinaol has been isolated from the rhizoma of Arundina graminifolia. The structure of has been elucidated as 7-hydroxy-1-(p-hydroxybenzyl)-2,4-dimethoxy-9,10-dihydrophenanthrene on the basis of physical and chemical evidence and spectral analysis.

Two new oxygen-containing biomarkers isolated from the Chinese Maoming oil shale by silica gel column chromatography and preparative gas chromatography.

PubMed

Zhang, Xiangyun; Lu, Hong; Liao, Jing; Tang, Caiming; Sheng, Guoying; Peng, Ping'an

2017-02-01

Two biomarkers, 5,9-dimethyl-6-isopropyl-2-decanone (1) and 4,9,11-trimethyl-6-isopropyl-2-dodecanone (2), were isolated from Chinese Maoming oil shale by silica gel column chromatography and preparative gas chromatography. Their structures were elucidated by using spectroscopic techniques. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Discorhabdin P, a new enzyme inhibitor from a deep-water Caribbean sponge of the genus Batzella.

PubMed

Gunasekera, S P; McCarthy, P J; Longley, R E; Pomponi, S A; Wright, A E; Lobkovsky, E; Clardy, J

1999-01-01

Discorhabdin P (1), a new discorhabdin analogue, has been isolated from a deep-water marine sponge of the genus Batzella. Discorhabdin P (1) inhibited the phosphatase activity of calcineurin and the peptidase activity of CPP32. It also showed in vitro cytotoxicity against P-388 and A-549 cell lines. The isolation and structure elucidation of discorhabdin P (1) are described.

Antitumour polyether macrolides: four new halichondrins from the New Zealand deep-water marine sponge Lissodendoryx sp.

PubMed

Hickford, Sarah J H; Blunt, John W; Munro, Murray H G

2009-03-15

The isolation is reported of four new variants of the halichondrin B skeleton, very minor potently bioactive components from the Poecilosclerid sponge Lissodendoryx sp. These compounds were isolated in microgram quantities only from a collection of 1tonne of sponge. The structural elucidations relied heavily on the use of capillary NMR spectroscopy and the application of an HSQC-DEPT overlay technique.

[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.

Isolation and structure elucidation of tetrameric procyanidins from unripe apples (Malus pumila cv. Fuji) by NMR spectroscopy.

PubMed

Nakashima, Shohei; Oda, Chihiro; Masuda, Susumu; Tagashira, Motoyuki; Kanda, Tomomasa

2012-11-01

Procyanidins are plant secondary metabolites widely consumed and known to have various physiological functions, but their bioavailability and mechanism of action are still unclear especially for larger oligomers. One of the reasons is scarce information about the detailed structure of oligomeric procyanidins. As for apple, structures of procyanidin components larger than trimers are scarcely known. In this study, 11 tetrameric procyanidins including two known compounds were isolated from unripe apples (Malus pumila cv. Fuji) and identified by NMR spectroscopic analysis and phloroglucinol degradation. As a result, the detailed structural diversity of tetrameric procyanidins in apple was established. Copyright © 2012 Elsevier Ltd. All rights reserved.

Isolation and identification of three potential impurities of pholcodine bulk drug substance.

PubMed

Denk, O M; Gray, A I; Skellern, G G; Watson, D G

2000-07-01

Three previously unreported manufacturing impurities were isolated from a pholcodine mother liquor using preparative reversed-phase HPLC. The liquor was the residue remaining after recrystallisation of a production batch of pholcodine. The impurities, which are structurally related to pholcodine, were initially detected by thin-layer chromatography (TLC). Their structures were determined after separation by preparative HPLC (Econo-Prep 5 microm C18 column, 30 cm x 21.2 mm i.d.). Structure elucidation was carried out using nuclear magnetic resonance (NMR) spectroscopy, mass spectroscopy (MS) and ultra violet (UV) spectroscopy. The impurities were identified as alkylated derivatives of pholcodine possessing second 2-morpholinoethyl substituents at various positions.

Isolation and Structure Elucidation of Cembranoids from a Dongsha Atoll Soft Coral Sarcophyton stellatum.

PubMed

Ahmed, Atallah F; Chen, Yi-Wei; Huang, Chiung-Yao; Tseng, Yen-Ju; Lin, Chi-Chen; Dai, Chang-Feng; Wu, Yang-Chang; Sheu, Jyh-Horng

2018-06-14

Six new polyoxygenated cembrane-based diterpenoids, stellatumolides A⁻C ( 1 ⁻ 3 ), stellatumonins A and B ( 4 and 5 ), and stellatumonone ( 6 ), were isolated together with ten known related compounds ( 7 ⁻ 16 ) from the ethyl acetate (EtOAc) extract of soft coral Sarcophyton stellatum . The structures of the new compounds were established by extensive spectroscopic analyses, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy and data comparison with related structures. Compounds 8 and 14 were isolated from a natural source for the first time. The isolated metabolites were shown to be not cytotoxic against a limited panel of cancer cells. Compound 9 showed anti-inflammatory activity by reducing the expression of proinflammatory cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) proteins in lipopolysaccharide (LPS)-stimulated mouse leukaemic monocyte macrophage (RAW 264.7) cells.

A new isoflavone glucoside from Pterocarpus santalinus.

PubMed

Krishnaveni, K S; Srinivasa Rao, J V

2000-01-01

A new isoflavone glucoside (1) together with the known santal has been isolated from the heartwood of Pterocarpus santalinus. Based on spectral methods, the structure of the new compound was elucidated as 4',5-dihydroxy 7-O-methyl isoflavone 3'-O-beta-D-glucoside.

[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.

Isolation and structure elucidation of avocado seed (Persea americana) lipid derivatives that inhibit Clostridium sporogenes endospore germination.

PubMed

Rodríguez-Sánchez, Dariana Graciela; Pacheco, Adriana; García-Cruz, María Isabel; Gutiérrez-Uribe, Janet Alejandra; Benavides-Lozano, Jorge Alejandro; Hernández-Brenes, Carmen

2013-07-31

Avocado fruit extracts are known to exhibit antimicrobial properties. However, the effects on bacterial endospores and the identity of antimicrobial compounds have not been fully elucidated. In this study, avocado seed extracts were tested against Clostridium sporogenes vegetative cells and active endospores. Bioassay-guided purification of a crude extract based on inhibitory properties linked antimicrobial action to six lipid derivatives from the family of acetogenin compounds. Two new structures and four compounds known to exist in nature were identified as responsible for the activity. Structurally, most potent molecules shared features of an acetyl moiety and a trans-enone group. All extracts produced inhibition zones on vegetative cells and active endospores. Minimum inhibitory concentrations (MIC) of isolated molecules ranged from 7.8 to 15.6 μg/mL, and bactericidal effects were observed for an enriched fraction at 19.5 μg/mL. Identified molecules showed potential as natural alternatives to additives and antibiotics used by the food and pharmaceutical industries to inhibit Gram-positive spore-forming bacteria.

[Studies on the chemical constituents from Cissus pteroclada].

PubMed

Chi, Cui-Yun; Wang, Feng; Lei, Ting; Xu, Shao-Yu; Hong, Ai-Hua; Cen, Ying-Zhou

2010-10-01

To study the chemical constituents of Yao Medicine Cissus pteroclada. The compounds were isolated and purified by column chromatography with silica gel, TLC and recrystallization. Their structures were elucidated on the basis of physicochemical properties and spectra analysis. Six compounds were isolated and identified as beta-sitosterol (I), bergenin (II), 11-O-galloylbergenin (III), 11-O-(4-hydroxy benzoyl) bergenin (IV), gallic acid (V), daucosterol (VI). Compounds III and NIV are obtained from the genus for the first time. All the compounds are isolated from this plant for the first time except the compound II.

Secobatzellines A and B, two new enzyme inhibitors from a deep-water Caribbean sponge of the genus Batzella.

PubMed

Gunasekera, S P; McCarthy, P J; Longley, R E; Pomponi, S A; Wright, A E

1999-08-01

Secobatzelline A (1), a new batzelline natural analogue, and secobatzelline B (2), a likely artifact formed during the isolation procedure, have been isolated from a deep-water marine sponge of the genus Batzella. Secobatzellines A and B inhibited the phosphatase activity of calcineurin, and secobatzelline A inhibited the peptidase activity of CPP32. Both compounds showed in vitro cytotoxicity against P-388 and A-549 cell lines. The isolation and structure elucidation of secobatzellines A (1) and B (2) are described.

A Novel Ellagic Acid Derivative from Desbordesia glaucescens.

PubMed

DongmoMafodong, Faustine L; Tsopmo, Apollinaire; Awouafack, Maurice D; Roland, Tchuenguem T; Dzoyem, Jean P; Tane, Pierre

2015-10-01

One novel ellagic acid derivative, desglauside (1), was isolated from the leaves of Desbordesia glaucescens together with three known compounds [3',4'-di-O-methylellagic acid (2), oleanolic acid (3) and β-sitosterol-3-O-β-D-glucopyranoside (4)]. Their structures were elucidated on the basis of NMR spectroscopic and MS analysis, and by comparison with related published data. The crude extract, fractions and isolated compounds showed no activity against four yeast strains [Candida albicans (ATCC 9002), C. parapsilopsis (ATCC22019), C. tropicalis (ATCC750), Cryptococcus neoformans (IP95026) and one isolate of Candida guilliermondii].

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.

[Study on chemical constituents of Orobanche coerulescens].

PubMed

Zhao, Jun; Yan, Ming; Huang, Yi; He, Wen-yi; Zhao, Yu

2007-10-01

Six compounds were isolated and purified from Orobanche coerulescens by extraction and different kinds of column chromatography. The structures were determined on the basis of spectral analysis. The structures were elucidated as D-mannitol(I), beta-sitosterol(II), succinic acid(III), caffeic acid(IV), protocatechuic aldehyde(V) and daucosterol(VI). All compounds are obtained from this plant for the first time.

Guaiane dimers from Xylopia vielana.

PubMed

Kamperdick, C; Phuong, N M; Van Sung, T; Adam, G

2001-02-01

From the leaves of Xylopia vielana (Annonaceae) the three dimeric guaianes vielanin A-C were isolated and structurally elucidated by mass and NMR spectroscopy as 1-3. The structure of 1 contains a bridged ring system formed probably via a Diels-Alder reaction of two different guaiane monomers. Compounds 2 and 3 represent symmetric cyclobutanes formally generated from two equal guaiane moieties by [2 + 2] cycloaddition.

Cybastacines A and B: Antibiotic Sesterterpenes from a Nostoc sp. Cyanobacterium.

PubMed

Cabanillas, Alfredo H; Tena Pérez, Víctor; Maderuelo Corral, Santiago; Rosero Valencia, Diego Fernando; Martel Quintana, Antera; Ortega Doménech, Montserrat; Rumbero Sánchez, Ángel

2018-02-23

Cybastacines A (1) and B (2) were discovered as a novel pentacyclic sesterterpenoid-alkaloid skeleton structure, with a guanidinium group. These molecules were isolated from a Nostoc sp. cyanobacterium collected in the Canary Islands. Their structures were elucidated primarily by a combination of spectroscopic analyses and X-ray diffraction. These compounds showed antibiotic activities against several clinically relevant bacterial strains.

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.

Helikaurolides A-D with a Diterpene-Sesquiterpene Skeleton from Supercritical Fluid Extracts of Helianthus annuus L. var. Arianna.

PubMed

Torres, Ascensión; Molinillo, José M G; Varela, Rosa M; Casas, Lourdes; Mantell, Casimiro; Martínez de la Ossa, Enrique J; Macías, Francisco A

2015-10-02

Four novel compounds (1-4) with an unprecedented skeleton that combines a sesquiterpene lactone and a kaurane diterpene acid were isolated from Helianthus annuus L. var. Arianna extract, which was obtained under supercritical conditions. The structures of 1-4 were elucidated by NMR and MS analyses. The biosynthetic routes involve sesquiterpene lactones and kauranic acid, both of which were previously isolated from this species.

A new cytotoxic sterol methoxymethyl ether from a deep water marine sponge Scleritoderma sp. cf. paccardi.

PubMed

Gunasekera, S P; Kelly-Borges, M; Longley, R E

1996-02-01

24(R)-Methyl-5 alpha-cholest-7-enyl 3 beta-methoxymethyl ether (1), a new sterol ether, has been isolated from a deep-water marine sponge Scleritoderma sp. cf. paccardi. Compound 1 exhibited in vitro cytotoxicity against the cultured murine P-388 tumor cell line with an IC50 of 2.3 micrograms/mL. The isolation and structure elucidation of 1 by NMR spectroscopy is described.

Dianthosaponins A-F, triterpene saponins, flavonoid glycoside, aromatic amide glucoside and γ-pyrone glucoside from Dianthus japonicus.

PubMed

Nakano, Takahiro; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki

2011-01-01

From aerial parts of Dianthus japonicus, six new and seven known oleanane-type triterpene saponins were isolated. The structures of the new saponins, named dianthosaponins A-F, were elucidated by means of high resolution mass spectrometry, and extensive inspection of one- and two-dimensional NMR spectroscopic data. A new C-glycosyl flavone, a glycosidic derivative of anthranilic acid amide and a maltol glucoside were also isolated.

Two new prenylflavonoids from Morus alba.

PubMed

Gao, Li; Li, Yuan-Dong; Zhu, Bao-Kun; Li, Zhi-Yu; Huang, Li-Bin; Li, Xian-Yi; Wang, Fei; Ren, Fu-Cai; Liao, Tou-Gen

2018-02-01

Two new prenylflavonoids, morusalbols A and B (1 and 2), were isolated from the branches and leaves of Morus alba, together with three known compounds, kuwanon C (3), morusin (4), morusinol (5). The structures of these two prenylflavonoids were elucidated by extensive analyzes of the spectroscopic data.

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).

Isolation and synthesis of antibacterial prenylated acylphloroglu-cinols from Psorothamnus fremontii

USDA-ARS?s Scientific Manuscript database

Antibacterial assay-guided fractionation of the methanol extract of the native American plant Psorothamnus fremontii followed by structure elucidation afforded three prenylated acylphloroglucinol derivatives, psorothatins A-C (1-3). They feature a unique a,ß-epoxyketone functionality and an a,ß-hydr...

Graminone B, a novel lignan with vasodilative activity from Imperata cylindrica.

PubMed

Matsunaga, K; Shibuya, M; Ohizumi, Y

1994-12-01

Two novel lignans, graminones A [1] and B [2] have been isolated from Imperata cylindrica and their structures have been elucidated on the basis of their spectral data. Graminone B [2] showed inhibitory activity on the contraction of the rabbit aorta.

A new stilbenoid from Arundina graminifolia.

PubMed

Liu, Mei-Feng; Han, Yun; Xing, Dong-Ming; Shi, Yue; Xu, Li-Zhen; Du, Li-Jun; Ding, Yi

2004-09-01

A chemical investigation of the Orchidaceae Arundina gramnifolia has led to the isolation of a novel stilbenoid, named arundinan (1). The structure of 1 has been elucidated as 2-(p-hydroxybenzyl)-3-hydroxy-5-methoxybibenzyl on the basis of physical and chemical evidence and spectral analysis.

Two new oxysporone derivatives from the fermentation broth of the endophytic plant fungus Pestalotiopsis karstenii isolated from stems of Camellia sasanqua.

PubMed

Luo, Du Qiang; Zhang, Lei; Shi, Bao Zhong; Song, Xiao Mei

2012-07-17

Two new oxysporone derivatives, pestalrone A (1) and pestalrone B (2), along with two known structurally related compounds 3, 4, were from the fermentation broth of the endophytic plant fungus Pestalotiopsis karstenii isolated from stems of Camellia sasanqua. Their structures and relative configurations were elucidated by extensive spectroscopic analysis and comparison of chemical shifts with related known compounds. Compound 2 exhibited significant activities agains HeLa, HepG2 and U-251 with IC₅₀ values of 12.6, 31.7 and 5.4 µg/mL, respectively.

Anti-inflammatory steroids from the rhizomes of Dioscorea septemloba Thunb.

PubMed

Zhang, Yi; Yu, Hai-Yang; Chao, Li-Ping; Qu, Lu; Ruan, Jing-Ya; Liu, Yan-Xia; Dong, Yong-Zhe; Han, Li-Feng; Wang, Tao

2016-08-01

Seven new steroid glycosides, dioscorosides A1 (1), A2 (2), B1 (3), B2 (4), C1 (5), C2 (6), and D (7), together with 22 known ones (8-29) were isolated from the rhizomes of Dioscorea septemloba, their structures were elucidated by chemical and spectroscopic methods. All isolates were evaluated for in vitro anti-inflammatory potential using LPS-stimulated RAW 264.7 murine macrophages. Among them, spirostane glycosides 18 and 21-24 exhibited significant inhibition of nitrite production. Moreover, the structure-activity relationship was summarized. Copyright © 2016 Elsevier Inc. All rights reserved.

Isolation of antimicrobial compounds from guava (Psidium guajava L.) and their structural elucidation.

PubMed

Arima, Hidetoshi; Danno, Gen-ichi

2002-08-01

Four antibacterial compounds were isolated from leaves of guava (Psidium guajava L.), and the structures of these compounds were established on the basis of chemical and spectroscopic evidence. Two new flavonoid glycosides, morin-3-O-alpha-L-lyxopyranoside and morin-3-O-alpha-L-arabopyranoside, and two known flavonoids, guaijavarin and quercetin, were identified. The minimum inhibition concentration of morin-3-O-alpha-L-lyxopyranoside and morin-3-O-alpha-L-arabopyranoside was 200 microg/ml for each against Salmonella enteritidis, and 250 microg/ml and 300 microg/ml against Bacillus cereus, respectively.

Building blocks for automated elucidation of metabolites: natural product-likeness for candidate ranking.

PubMed

Jayaseelan, Kalai Vanii; Steinbeck, Christoph

2014-07-05

In metabolomics experiments, spectral fingerprints of metabolites with no known structural identity are detected routinely. Computer-assisted structure elucidation (CASE) has been used to determine the structural identities of unknown compounds. It is generally accepted that a single 1D NMR spectrum or mass spectrum is usually not sufficient to establish the identity of a hitherto unknown compound. When a suite of spectra from 1D and 2D NMR experiments supplemented with a molecular formula are available, the successful elucidation of the chemical structure for candidates with up to 30 heavy atoms has been reported previously by one of the authors. In high-throughput metabolomics, usually 1D NMR or mass spectrometry experiments alone are conducted for rapid analysis of samples. This method subsequently requires that the spectral patterns are analyzed automatically to quickly identify known and unknown structures. In this study, we investigated whether additional existing knowledge, such as the fact that the unknown compound is a natural product, can be used to improve the ranking of the correct structure in the result list after the structure elucidation process. To identify unknowns using as little spectroscopic information as possible, we implemented an evolutionary algorithm-based CASE mechanism to elucidate candidates in a fully automated fashion, with input of the molecular formula and 13C NMR spectrum of the isolated compound. We also tested how filters like natural product-likeness, a measure that calculates the similarity of the compounds to known natural product space, might enhance the performance and quality of the structure elucidation. The evolutionary algorithm is implemented within the SENECA package for CASE reported previously, and is available for free download under artistic license at http://sourceforge.net/projects/seneca/. The natural product-likeness calculator is incorporated as a plugin within SENECA and is available as a GUI client and command-line executable. Significant improvements in candidate ranking were demonstrated for 41 small test molecules when the CASE system was supplemented by a natural product-likeness filter. In spectroscopically underdetermined structure elucidation problems, natural product-likeness can contribute to a better ranking of the correct structure in the results list.

Ca2+-Signal Transduction Inhibitors, Kujiol A and Kujigamberol B, Isolated from Kuji Amber Using a Mutant Yeast.

PubMed

Uchida, Takeshi; Koshino, Hiroyuki; Takahashi, Shunya; Shimizu, Eisaku; Takahashi, Honoka; Yoshida, Jun; Shinden, Hisao; Tsujimura, Maiko; Kofujita, Hisayoshi; Uesugi, Shota; Kimura, Ken-Ichi

2018-04-27

A podocarpatriene and a labdatriene derivative, named kujiol A [13-methyl-8,11,13-podocarpatrien-19-ol (1)] and kujigamberol B [15,20-dinor-5,7,9-labdatrien-13-ol (2)], respectively, were isolated from Kuji amber through detection with the aid of their growth-restoring activity against a mutant yeast strain ( zds1Δ erg3Δ pdr1Δ pdr3Δ), which is known to be hypersensitive with respect to Ca 2+ -signal transduction. The structures were elucidated by spectroscopic data analysis. Compounds 1 and 2 are rare organic compounds from Late Cretaceous amber, and the mutant yeast used seems useful for elucidating a variety of new compounds from Kuji amber specimens, produced before the K-Pg boundary.

Pestalotiopamide E, a new amide from the endophytic fungus Pestalotiopsis sp.

PubMed

Xu, Jing; Lin, Qiang; Wang, Bin; Wray, Victor; Lin, Wen-Han; Proksch, Peter

2011-04-01

Chemical examination of the endophytic fungus Pestalotiopsis sp., isolated from the leaves of the Chinese mangrove Rhizophora mucronata, yielded a new amide called pestalotiopamide E (1). The structure of the new compound was unambiguously elucidated on the basis of extensive spectroscopic data analysis.

Echinopsacetylenes A and B, new thiophenes from Echinops transiliensis

USDA-ARS?s Scientific Manuscript database

Two new polyacetylene thiophenes, echinopsacetylenes A and B (1 and 2), were isolated from the root of Echinops transiliensis. The structures of 1 and 2 were elucidated on the basis of spectroscopic analyses and chemical transformations. Echinopsacetylene A (1) is the first natural product possessin...

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.

[Study on the chemical constituents of aerial part of Ligusticum jeholense].

PubMed

Sun, Jia-ming; Zhang, Bo; Chang, Ren-long; Ye, Dou-dan; Zhang, Hui

2011-07-01

To study the chemical constituents of the aerial part of Ligusticum jeholense. The constituents were isolated by sillica gel column chromatography, Sephadex LH-20 column chromatography and their structures were elucidated by spectral analysis. Seven compounds were separated from the EtOH extracts. Their structures were identified as psoralen (1), beta-sitosterol (2), daucosterol (3), kaempferol-3-O-(2",4"-di-E-p-coumaroyl)-alpha-L-rhamnoside (4), kaempferol-3-O-beta-D-galactoside (5), quercetin-3-O-beta-D-galactoside (6), sucrose (7). Compounds 1, 4, 5 and 6 are isolated from the genus for the first time. Compounds 2, 3 and 7 are isolated from the aerial part of the plant for the first time.

Structure Elucidation and in Vitro Toxicity of New Azaspiracids Isolated from the Marine Dinoflagellate Azadinium poporum

PubMed Central

Krock, Bernd; Tillmann, Urban; Potvin, Éric; Jeong, Hae Jin; Drebing, Wolfgang; Kilcoyne, Jane; Al-Jorani, Ahmed; Twiner, Michael J.; Göthel, Qun; Köck, Matthias

2015-01-01

Two strains of Azadinium poporum, one from the Korean West coast and the other from the North Sea, were mass cultured for isolation of new azaspiracids. Approximately 0.9 mg of pure AZA-36 (1) and 1.3 mg of pure AZA-37 (2) were isolated from the Korean (870 L) and North Sea (120 L) strains, respectively. The structures were determined to be 3-hydroxy-8-methyl-39-demethyl-azaspiracid-1 (1) and 3-hydroxy-7,8-dihydro-39-demethyl-azaspiracid-1 (2) by 1H- and 13C-NMR. Using the Jurkat T lymphocyte cell toxicity assay, (1) and (2) were found to be 6- and 3-fold less toxic than AZA-1, respectively. PMID:26528990

[Studies on chemical constituents of cultivated Cistanche salsa].

PubMed

Yang, Jian-Hu; Hu, Jun-Ping; Rena, Kasimu; Du, Nian-Sheng

2008-11-01

To study the chemical constituents of cultivated Cistanche salsa. Compounds were isolated and purified on several chromatography, and then were identified by physico-chemical properties and structurally elucidated by spectral analysis. Seven compounds were isolated and identified as beta-sitosterol (I), daucosterol (II), beta-sitosteryl glucoside 3'-O-heptadecoicate (III), 8-hydroxygeraniol 1-beta-D-glucopyranoside (IV), 2-methanol-5-hydroxy-pyridine (V), betaine (VI), galactitol (VII). The chemical constituents of artificial cultivated Cistanche salsa are studied for the first time. Among them, compound III and IV are isolated from the plant for the first time, compound V is isolated from this genus for the first time.

Withanolides from Jaborosa caulescens var. bipinnatifida

PubMed Central

Zhang, Huaping; Cao, Cong-Mei; Gallagher, Robert J.; Day, Victor W.; Montenegro, Gloria; Timmermann, Barbara N.

2013-01-01

Two new withanolides 2,3-dihydrotrechonolide A (1) and 2,3-dihydro-21-hydroxytrechonolide A (2) were isolated along with two known withanolides trechonolide A (3) and jaborosalactone 39 (4) from Jaborosa caulescens var. bipinnatifida (Solanaceae). The structures of 1-2 were elucidated through 2D NMR and other spectroscopic techniques. In addition, the structure of withanolide 1 was confirmed by X-ray crystallographic analysis. PMID:24314746

[Studies on the chemical constituents of Gueldenstaedtia stenophylla].

PubMed

Wei, You-xia; Chen, Li; Wang, Jun-xian

2007-08-01

To study the chemical constituents of Gueldenstaeditia stenophylla. The constituents were isolated by alcohol extraction, column chromatography on silica gel. Their structures were elucidated by chemical and spectroscopic methods. Six compounds were obtained, and five of them were identified as n-hexadecanioc acid (I), beta-sitosterol (II), daucosterol (III), apigenin (IV), D-fructose (VI). Compound V was being determined. Five compounds are isolated from Gueldenstaedtia stenophylla and compounds I, III are extracted from Gueldenstaedtia Fisch for the first time.

Two new diterpenoid lactones isolated from Andrographis paniculata.

PubMed

Wang, Gui-Yang; Wen, Ting; Liu, Fei-Fei; Tian, Hai-Yan; Chun-Lin, Fan; Huang, Xiao-Jun; Ye, Wen-Cai; Wang, Ying

2017-06-01

In the present study, two new diterpenoid lactones, 3-deoxy-andrographoside (1) and 14-deoxy-15-methoxy-andrographolide (2), were isolated from the aerial parts of Andrographis paniculata. Their structures were elucidated by combination of NMR, MS, and chemical methods. The configurations of 1 and 2 were established based on the analysis of ROESY data and single crystal X-ray diffraction experiment. Copyright © 2017 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.

Isolation and structural elucidation of cytotoxic compounds from the root bark of Diospyros quercina (Baill.) endemic to Madagascar

PubMed Central

Ruphin, Fatiany Pierre; Baholy, Robijaona; Emmanuel, Randrianarivo; Amelie, Raharisololalao; Martin, Marie-Therese; Koto–te-Nyiwa, Ngbolua

2014-01-01

Objective To isolate and characterize the cytotoxic compounds from Diospyros quercina (Baill.) G.E. Schatz & Lowry (Ebenaceae). Methods An ethno-botanical survey was conducted in the south of Madagascar from July to August 2010. Bio-guided fractionation assay was carried out on the root bark of Diospyros quercina, using cytotoxicity bioassay on murine P388 leukemia cell lines as model. The structures of the cytotoxic compounds were elucidated by 1D and 2D NMR spectroscopy and mass spectrometry. Results Biological experiments resulted in the isolation of three bioactive pure compounds (named TR-21, TR-22, and TR-23) which exhibited very good in vitro cytotoxic activities with the IC50 values of (0.017 5±0.0060) µg/mL, (0.089±0.005) µg/mL and (1.027±0.070) µg/mL respectively. Thus, they support the claims of traditional healers and suggest the possible correlation between the chemical composition of this plant and its wide use in Malagasy folk medicine to treat cancer. Conclusions The ability of isolated compounds in this study to inhibit cell growth may represent a rational explanation for the use of Diospyros quercina root bark in treating cancer by Malagasy traditional healers. Further studies are, therefore, necessary to evaluate the in vivo anti-neoplastic activity of these cytotoxic compounds as effective anticancer drugs. PMID:25182433

Ravynic acid, an antibiotic polyeneyne tetramic acid from Penicillium sp. elucidated through synthesis.

PubMed

Myrtle, J D; Beekman, A M; Barrow, R A

2016-09-21

A new antibiotic natural product, ravynic acid, has been isolated from a Penicillium sp. of fungus, collected from Ravensbourne National Park. The 3-acylpolyenyne tetramic acid structure was definitively elucidated via synthesis. Highlights of the synthetic method include the heat induced formation of the 3-acylphosphorane tetramic acid and a selective Wittig cross-coupling to efficiently prepare the natural compounds carbon skeleton. The natural compound was shown to inhibit the growth of Staphylococcus aureus down to concentrations of 2.5 µg mL(-1).

Three new norsesquiterpenoids from the seeds of Alpinia galanga.

PubMed

Bian, Meng-Qin; Kang, Jie; Wang, Hong-Qing; Zhang, Qing-Jian; Liu, Chao; Chen, Ruo-Yun

2014-01-01

From the seeds of Alpinia galanga Willd., three new norsesquiterpenoid racemic mixtures, galanols A-C (1-3) were isolated, along with three known sesquiterpenoids (4-6). Their structures were elucidated by means of UV, IR, HR-ESI-MS, 1D NMR and 2D NMR spectroscopic data.

A new acylated isoflavone glucoside from Pterocarpus santalinus.

PubMed

Krishnaveni, K S; Srinivasa Rao, J V

2000-09-01

Phytochemical investigation on the constituents of heartwood of Pterocarpus santalinus resulted in the isolation of a new acylated isoflavone glucoside. The structure of the new compound was elucidated on the basis of spectral studies as 4',5-dihydroxy-7-O-methyl isoflavone 3'-O-D-(3''-E-cinnamoyl)glucoside.

New biologically active epidioxysterols from Stereum hirsutum.

PubMed

Cateni, Francesca; Doljak, Bojan; Zacchigna, Marina; Anderluh, Marko; Piltaver, Andrej; Scialino, Giuditta; Banfi, Elena

2007-11-15

From the fungus Stereum hirsutum have been isolated and identified two new epidioxysterols 1, 4, together with two known ones 2 and 3. Their structures were elucidated on the basis of spectroscopic analysis and chemical reactions. Epidioxysterols 1-4 have been shown to possess a significant activity against Mycobacterium tuberculosis.

[Chemical constituents from aerial part of Aconitum brachypodum].

PubMed

Wang, Hong-Yun; Zuo, Ai-Xue; Sun, Yun; Rao, Gao-Xiong

2014-08-01

To study the chemical constituents from the aerial part of Aconitum brachypodum. The constituents were isolated and purified by silica gel, activated alumina and Sephadex LH-20 column chromatography. their structures were elucidated on the basis of spectral data and physiochemical evidence. Eleven compounds were isolated from 80% ethanol extract and identified as secokaraconitine (1), brachyaconitines A (2), C (3), talatisamine (4), hypaconitine (5), songrine (6), bullatine A (7), 7-carbony sitosterone (8), lupeol (9), β-sitosterol (10) and daucosterol (11). All compounds are isolated from the aerial part of Aconitum brachypodum for the first time.

[Chemical constituents from Neo-Taraxacum siphonathum].

PubMed

Shi, Shuyun; Zhou, Honghao; Zhang, Yuping; Huang, Kelong; Liu, Suqin

2009-04-01

To study the chemical constituents from the antioxidant fraction of Neo-Taraxacum siphonathum. Various chromatographic techniques were used to isolate and purify the constituents. The structures were elucidated on the basis of chemical evidence and spectral analysis. Ten compounds were isolated and identified from Neo-T. siphonathum, caffeic acid (1), chlorogenic acid (2), quercetin (3), luteolin (4), quercetin-3-O-beta-D-glucopyranoside (5), quercetin-3-O-alpha-D-arabinofuranoside (6), quercetin-3-O-alpha-D-arabinopyranoside (7), luteolin-7-O-beta-D-glucopyranoside (8), beta-sitosterol (9) and daucosterol (10). Compounds 1-10 were isolated from this plant for the first time.

[Chemical constituents from roots of Platycodon grandiflorum].

PubMed

Li, Ling-Jun; Liu, Zhen-Hua; Chen, Yun; Tian, Jing-Kui

2006-09-01

To study the chemical constituents from roots of Platycodon grandiflorum. Column chromatography (silica gel, macroporous resin, sephadex LH - 20 and the preparative RP - HPLC were used to isolate the constituents. Their structures were elucidated by physical and spectral data. Eight compounds were isolated and identified as tangeritin (1), 3-O-beta-D-glucopyranosylplatycodigenin methyl ester (2), 3-O-beta-D-glucopyranosylplaticogenic acid A lactone (3), 3-O-beta-D-glucopyranosylplatycodigenin (4), deapio-platyconic acid A lactone (5), deapio-platycodin-D (6), platycoside-G1 (7) and platycoside-E (8). Compounds 1,3 and 5 were isolated from this plant for the first time.

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.

[Study on water-soluble chemical constituents of Taraxacum mongolicum].

PubMed

Liu, Hua-qing; Wang, Tian-lin

2014-06-01

To study the water-soluble chemical constituents of Taraxacum mongolicum. The chemical constituents were isolated and purified by means of several chromatographic techniques and their structures were elucidated by spectroscopic methods. Nine compounds were isolated and identified as trans-p-coumaryl alcohol(1), trans-p-coumaryl aldehyde(2),p- hydroxybenzoate (3) , p-hydroxyphenyl-propionic acid (4) , 4-hydroxy-2, 6-dimethoxyphenol-1 -O-β-D-glucopyranoside (5) , protocate- chuic aldehyde(6) ,rutin(7) ,quercetin(8) ,kaempferal-3-O-α-L-rhamnopyranosyl-( 1-6) -β-D-glucopyranoside(9). Com pounds 1-6 are isolated from this plant for the first time.

Spoxazomicin D and Oxachelin C, Potent Neuroprotective Carboxamides from the Appalachian Coal Fire-Associated Isolate Streptomyces sp. RM-14-6.

PubMed

Shaaban, Khaled A; Saunders, Meredith A; Zhang, Yinan; Tran, Tuan; Elshahawi, Sherif I; Ponomareva, Larissa V; Wang, Xiachang; Zhang, Jianjun; Copley, Gregory C; Sunkara, Manjula; Kharel, Madan K; Morris, Andrew J; Hower, James C; Tremblay, Matthew S; Prendergast, Mark A; Thorson, Jon S

2017-01-27

The isolation and structure elucidation of six new bacterial metabolites [spoxazomicin D (2), oxachelins B and C (4, 5), and carboxamides 6-8] and 11 previously reported bacterial metabolites (1, 3, 9-12a, and 14-18) from Streptomyces sp. RM-14-6 is reported. Structures were elucidated on the basis of comprehensive 1D and 2D NMR and mass spectrometry data analysis, along with direct comparison to synthetic standards for 2, 11, and 12a,b. Complete 2D NMR assignments for the known metabolites lenoremycin (9) and lenoremycin sodium salt (10) were also provided for the first time. Comparative analysis also provided the basis for structural revision of several previously reported putative aziridine-containing compounds [exemplified by madurastatins A1, B1, C1 (also known as MBJ-0034), and MBJ-0035] as phenol-dihydrooxazoles. Bioactivity analysis [including antibacterial, antifungal, cancer cell line cytotoxicity, unfolded protein response (UPR) modulation, and EtOH damage neuroprotection] revealed 2 and 5 as potent neuroprotectives and lenoremycin (9) and its sodium salt (10) as potent UPR modulators, highlighting new functions for phenol-oxazolines/salicylates and polyether pharmacophores.

Microtropins Q-W, ent-Labdane Glucosides: Microtropiosides G-I, Ursane-Type Triterpene Diglucoside and Flavonol Glycoside from the Leaves of Microtropis japonica.

PubMed

Terazawa, Saori; Uemura, Yuka; Koyama, Yuka; Kawakami, Susumu; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki; Shinzato, Takakazu; Kawahata, Masatoshi; Yamaguchi, Kentaro

2017-01-01

Microtropins Q-W, (2S,3R)-2-ethyl-2,3-dihydroxybutyrate of various glucosides and glucose, as well as three ent-labdane diterpenoid glucosides, named microtropiosides G, H and I, an ursane-type triterpene diglucoside and a flavonoid glycoside were isolated from the MeOH extract of the leaves of Microtropis japonica. The structure of microtropioside A, also isolated from the branches of M. japonica, was elucidated spectroscopically in a previous experiment and was found to possess a rare seven-membered oxyrane ring. Its structure was confirmed by X-ray crystallographic analysis of its pentaacetate.

Phellilane L, Sesquiterpene Metabolite of Phellinus linteus: Isolation, Structure Elucidation, and Asymmetric Total Synthesis.

PubMed

Ota, Koichiro; Yamazaki, Ikuma; Saigoku, Takahiro; Fukui, Mei; Miyata, Tomoki; Kamaike, Kazuo; Shirahata, Tatsuya; Mizuno, Fumi; Asada, Yoshihisa; Hirotani, Masao; Ino, Chieko; Yoshikawa, Takafumi; Kobayashi, Yoshinori; Miyaoka, Hiroaki

2017-12-01

A new cyclopropane-containing sesquiterpenoid, phellilane L (1), was isolated from the medicinal mushroom Phellinus linteus ("Meshimakobu" in Japanese), a member of the Hymenochaetaceae family and a well-known fungus that is widely used in East Asia. The planar structure of 1 was determined on the basis of spectroscopic analysis. The authors achieved the first total synthesis of 1. Our protecting group-free synthesis features a highly stereoselective one-pot synthesis involving an intermolecular alkylation/cyclization/lactonization strategy for construction of the key cyclopropane-γ-lactone intermediate. Additionally, our synthesis determined the absolute configuration of phellilane L (1).

Nonthmicin, a Polyether Polyketide Bearing a Halogen-Modified Tetronate with Neuroprotective and Antiinvasive Activity from Actinomadura sp.

PubMed

Igarashi, Yasuhiro; Matsuoka, Noriaki; In, Yasuko; Kataura, Tetsushi; Tashiro, Etsu; Saiki, Ikuo; Sudoh, Yuri; Duangmal, Kannika; Thamchaipenet, Arinthip

2017-03-17

Nonthmicin (1), a new polyether polyketide bearing a chlorinated tetronic acid, was isolated from the culture extract of a soil-derived Actinomadura strain. The structure of 1 was elucidated by interpretation of NMR and MS spectroscopic data, and the absolute configuration of 1 was proposed on the basis of the crystal structure of its dechloro congener ecteinamycin (2) also isolated from the same strain. Tetronic acids modified by halogenation have never been reported from natural products. Compounds 1 and 2 were found to have neuroprotective activity and antimetastatic properties at submicromolar concentrations in addition to antibacterial activity.

Structure of kaurane-type diterpenes from Parinari sprucei and their potential anticancer activity.

PubMed

Braca, Alessandra; Armenise, Annahil; Morelli, Ivano; Mendez, Jeannette; Mi, Qiuwen; Chai, Hee-Byung; Swanson, Steven M; Kinghorn, A Douglas; De Tommasi, Nunziatina

2004-06-01

Twenty-three kaurane-type diterpenes 1 - 23, including twenty new natural products 1 - 20, have been isolated from the leaves of Parinari sprucei and their structures elucidated by spectroscopic and chemical analysis. The isolated compounds were tested for their cytotoxic activity towards a panel of cancer cell lines. Compounds 9 and 10 showed activity against all cell lines with ED (50) values in the range of 10 - 20 microg/mL. The previously known 13-hydroxy-15-oxozoapatlin 21 was evaluated in an in vivo hollow fiber test, and found to be active with KB and LNCaP cells at the concentrations used.

[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.

Lignans from Arnica species.

PubMed

Schmidt, Thomas J; Stausberg, Sabine; Raison, Jeanette Von; Berner, Matthias; Willuhn, Günter

2006-05-10

From four Arnica species (A. angustifolia Vahl ssp. attenuata (Greene) Maguire, A. lonchophylla Greene ssp. lonchophylla Maguire (flowerheads), A. chamissonis Less. ssp. foliosa (Nutt.) Maguire, A. montana L. (roots and rhizomes)) a total of twelve lignans of the furofuran-, dibenzylbutyrolactone- and dibenzylbutyrolactol-type were isolated. No report on lignans as constituents of Arnica species exists so far. Besides the known pinoresinol, epipinoresinol, phillygenin, matairesinol, nortrachelogenin and nortracheloside, six dibenzylbutyrolactol derivatives with different stereochemistry and substitution at C-9 were isolated and their structures elucidated by NMR spectroscopic and mass spectral analysis.

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.

Aedes aegypti Larvicidal Sesquiterpene Alkaloids from Maytenus oblongata.

PubMed

Touré, Seindé; Nirma, Charlotte; Falkowski, Michael; Dusfour, Isabelle; Boulogne, Isabelle; Jahn-Oyac, Arnaud; Coke, Maïra; Azam, Didier; Girod, Romain; Moriou, Céline; Odonne, Guillaume; Stien, Didier; Houël, Emeline; Eparvier, Véronique

2017-02-24

Four new sesquiterpene alkaloids (1-4) with a β-dihydroagrofuran skeleton and a new triterpenoid (5) were isolated from an ethyl acetate extract of Maytenus oblongata stems. Their structures were elucidated using 1D and 2D NMR spectroscopy as well as MS and ECD experiments. The M. oblongata stem EtOAc extract and the pure compounds isolated were tested for larvicidal activity against Aedes aegypti under laboratory conditions, and compounds 2 and 3 were found to be active.

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.

New polyacetylenes glycoside from Eclipta prostrate with DGAT inhibitory activity.

PubMed

Meng, Xiao; Li, Ban-Ban; Lin, Xin; Jiang, Yi-Yu; Zhang, Le; Li, Hao-Ze; Cui, Long

2018-06-08

One new polyacetylene glycoside eprostrata Ⅰ (1), together with seven known compounds (2-8), were isolated from Eclipta prostrata. Their structures were elucidated on the basis of spectroscopic and physico-chemical analyses. All the isolates were evaluated inhibitory activity on DGAT in an in vitro assay. Compounds 1-8 were found to exhibit inhibitory activity of DGAT1 with IC 50 values ranging from 74.4 ± 1.3 to 101.1 ± 1.1 μM.

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.

[A new eremophilane derivative from Senecio dianthus].

PubMed

Han, He-Dong; Hu, Hai-Qing; Li, Yan; Wang, Xiao-Ling

2013-10-01

A new eremophilane derivative, 4,5,11-trimethyl-9( 10), 7 ( 11) -eremophiladien-8-keto-12-carboxylic acid-beta-D-glucopyranoside( which named dianthuside A) 1 and four known compounds, 5,7,4'-trihydroxy-flavonone-3-0-beta-D-glucoside (2), quercetin-3-0-beta-D-glucoside(3) ,hyperin(4) and rutin(5) have been isolated from the aerial part of Senecio dianthus. Their structures were elucidated by physicochemical properties and spectroscopic data analysis. Compounds 2, 4 and 5 were isolated from this plant for the first time.

Dianthosaponins G-I, triterpene saponins, an anthranilic acid amide glucoside and a flavonoid glycoside from the aerial parts of Dianthus japonicus and their cytotoxicity.

PubMed

Kanehira, Yuka; Kawakami, Susumu; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki

2016-10-01

Extensive isolation work on the 1-BuOH-soluble fraction of a MeOH extract of the aerial parts of Dianthus japonicus afforded three further triterpene glycosyl estsers, termed dianthosaponins G-I, an anthranilic acid amide glucoside and a C-glycosyl flavonoid along with one known triterpene saponin. Their structures were elucidated from spectroscopic evidence. The cytotoxicity of the isolated compounds toward A549 cells was evaluated.

Hydrolyzable tannins and related polyphenols from Eucalyptus globulus.

PubMed

Hou, A J; Liu, Y Z; Yang, H; Lin, Z W; Sun, H D

2000-01-01

Eucaglobulin (1), a new complex of gallotannin and monoterpene, was isolated from the leaves of Eucaloptus globulus. Its structure was elucidated on the basis of spectral data. Four known hydrolyzable tannins [tellimagrandin I (2), eucalbanin C (3), 2-O-digalloyl-1,3,4-tri-O-galloyl-beta-D-glucose (4), 6-O-digalloyl-1,2,3-tri-O-galloyl-beta-D-glucose (5)], as well as gallic acid (6) and (+)-catechin (7), were also isolated. The antibacterial effects of some of these compounds were examined.

A new flavanenol with urease-inhibition activity isolated from roots of manna plant camelthorn ( Alhagi maurorum)

NASA Astrophysics Data System (ADS)

Laghari, Abdul Hafeez; Memon, Shahabuddin; Nelofar, Aisha; Khan, Khalid M.; Yasmin, Arfa; Syed, Muhammad Noman; Aman, Afsheen

2010-02-01

A new flavanenol ( 1) was isolated from ethyl acetate fraction of roots of Alhagi maurorum (Fabaceae). Its structure was elucidated on the basis of spectroscopic evidence using elemental analysis, IR, MS, and NMR techniques. It was determined to be 5,6,7,8,2',3',5',6'-octamethoxyflavan-3-en-4'-ol. Experiments were carried out to evaluate its urease-inhibition activity. From the observations it has been noticed that flavanenol possesses remarkable urease-inhibitory effect.

A new bipyrrole and some phenolic constituents in prunes (Prunus domestica L.) and their oxygen radical absorbance capacity (ORAC).

PubMed

Kayano, Shin-ichi; Kikuzaki, Hiroe; Ikami, Takao; Suzuki, Tomoo; Mitani, Takahiko; Nakatani, Nobuji

2004-04-01

Isolation and structural elucidation of prune constituents were performed and total 10 compounds were determined by NMR and MS analyses. A novel compound was identified to be 2-(5-hydroxymethyl-2',5'-dioxo-2',3',4',5'-tetrahydro-1'H-1,3'-bipyrrole)carbaldehyde, and 7 phenolic compounds were isolated from prunes for the first time. In addition, antioxidant activity of them was evaluated on the basis of the oxygen radical absorbance capacity (ORAC).

Limonoid from the rhizomes of Luvunga scandens (Roxb.) Buch. Ham.

PubMed

Nguyen, Tan Phat; Minh, Nhat Phan; Dat, Trong Bui; Le, Tien Dung; Tran Nguyen, Minh An; Pham, Thi Nhat Trinh; Tri, Dinh Mai

2017-10-01

For first time, the chemical constituents of the rhizomes of Luvunga scandens (Roxb.) Buch. Ham. were investigated and led to the isolation of one new limonoid named Luvunga A (1), together with seven known compounds, including one limonoid (2) and six coumarins (3-8) were isolated for the first time from the species L. scandens by various chromatography methods. Their chemical structures were elucidated by IR, UV, HR-ESI-MS, NMR 1D and 2D experiments and compared with literatures.

Studies on the sesquiterpene lactones from Laurus novocanariensis lead to the clarification of the structures of 1-epi-tatridin B and its epimer tatridin B.

PubMed

Fraga, Braulio M; Terrero, David; Cabrera, Inmaculada; Reina, Matías

2018-06-01

The germacranolide 1-epi-tatridin B has been isolated from the aerial parts of Laurus novocanariensis. We have observed that the identification of this lactone and its epimer tetradin B in the scientific literature is confusing and contradictory. We have therefore studied this issue clarifying errors and contributing to the structural elucidation of other related products. Moreover, we have isolated from this plant a lactone with an 1,5-ether bridge, previously obtained from Austrolabium candidum. We have now named it austroliolide, reassigned its 13 C NMR spectrum and compared its structure with that of badgerin. In addition, we have also isolated from L. novocanariensis the known germacranolides artemorin, costunolide, tatridin A, tulirinol and verlotorin, the eudesmanolides β-cyclopyrethrosin, 1β-hydroxy-arbusculin A, magnoliaolide and reynosin, and the guaianolide dehydrocostus lactone. Copyright © 2018 Elsevier Ltd. All rights reserved.

Structural analysis of proanthocyanidins isolated from fruit stone of Chinese hawthorn with potent antityrosinase and antioxidant activity.

PubMed

Chai, Wei-Ming; Chen, Chih-Min; Gao, Yu-Sen; Feng, Hui-Ling; Ding, Yu-Mei; Shi, Yan; Zhou, Han-Tao; Chen, Qing-Xi

2014-01-08

Proanthocyanidins were isolated from fruit stone of Chinese hawthorn (Crataegus pinnatifida Bge. var. major N.E.Br.). Their structures were analyzed and elucidated by methods of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) and high performance liquid chromatography electrospray ionization mass spectrometry (HPLC-ESI-MS). The results demonstrated that these compounds are complicated mixtures of homo- and heteropolymers consisting of procyanidin/procyanidin gallate and prodelphinidin. They possessed structural heterogeneity in monomer units, polymer length, and interflavan linkage (A-type and B-type). Their antityrosinase and antioxidant activity were then investigated. The results revealed that they can inhibit tyrosinase activities, including the monophenolase activity and the diphenolase activity. In addition, proanthocyanidins possessed potent antioxidant activity. Our studies revealed that proanthocyanidins isolated from fruit stone of Chinese hawthorn may be applied in food, agriculture, pharmaceutical, and cosmetic industries.

A new meroterpenoid, chrodrimanin C, from YO-2 of Talaromyces sp.

PubMed

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

2012-01-01

The new meroterpenoid, chrodrimanin C (3), together with chrodrimanins A (2) and B (1) were isolated from okara (the insoluble residue of whole soybean) that had been fermented with strain YO-2 of Talaromyces sp. Their structures were elucidated by spectroscopic methods. The partial structures of 1 essential for exhibiting insecticidal activity were investigated by using a silkworm assay. The absolute configuration of 1 was also determined.

Withanolides from Jaborosa caulescens var. bipinnatifida.

PubMed

Zhang, Huaping; Cao, Cong-Mei; Gallagher, Robert J; Day, Victor W; Montenegro, Gloria; Timmermann, Barbara N

2014-02-01

Withanolides 2,3-dihydrotrechonolide A (1) and 2,3-dihydro-21-hydroxytrechonolide A (2) were isolated along with two known withanolides trechonolide A (3) and jaborosalactone 39 (4) from Jaborosa caulescens var. bipinnatifida (Solanaceae). The structures of 1-2 were elucidated through 2D NMR and other spectroscopic techniques. In addition, the structure of withanolide 1 was confirmed by X-ray crystallographic analysis. Copyright © 2013 Elsevier Ltd. All rights reserved.

Bioactive constituents from Chinese natural medicines. XXII. Absolute structures of new megastigmane glycosides, sedumosides E1, E2, E3, F1, F2, and G, from Sedum sarmentosum (Crassulaceae).

PubMed

Morikawa, Toshio; Zhang, Yi; Nakamura, Seikou; Matsuda, Hisashi; Muraoka, Osamu; Yoshikawa, Masayuki

2007-03-01

Six new megastigmane glycosides, sedumosides E1, E2, E3, F1, F2, and G, were isolated from the whole plant of Sedum sarmentosum (Crassulaceae). The structures of new constituents including the absolute configuration were elucidated on the basis of chemical and physicochemical evidence.

[Studies on the chemical constituents of the stems of Piper betle].

PubMed

Yin, Yan; Huang, Xiang-Zhong; Wang, Jiong; Dai, Jian-Hui; Liang, Hui; Dai, Yun

2009-06-01

To study the chemical constituents from the stems of Piper betle. Various chromatographic techniques were used to isolate and purify the constituents. The structures of these compounds were elucidated on the basis of spectral analysis. Nine compounds were isolated from the petroleum ester and ethyl acetate soluble fractions of the 70% acetone extract and their structures were identified as 6beta-hydroxystigmast-4-en-3-one (1), beta-sitosterol (2), stigmasterol (3), oleanolic acid (4), 23-hydroxyursan-12-en-28-oic acid (5), beta-sitosterol-3-O-beta-D-glucoside-6'-O-palmitate (6), beta-daucosterol (7), (2S) -4'-hydroxy- 2,3-dihydroflavonone-7-O-beta-D-glucoside (8) and alpha-ethyl glucoside (9). Among these compounds, 1, 3 -9 are isolated from this plant for the first time.

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

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.

New chalcones bearing a long-chain alkylphenol from the rhizomes of Alpinia galanga.

PubMed

Yang, Wan-Qiu; Gao, Yuan; Li, Ming; Miao, De-Ren; Wang, Fei

2015-01-01

Three novel chalcones bearing a long-chain alkylphenol, galanganones A-C (1-3), were isolated from the rhizomes of Alpinia galanga. Their structures were elucidated by extensive spectroscopic analysis including 2D NMR experiments. Compounds 1-3 represent the first examples of long-chain alkylphenol-coupled chalcone.

Ciliatamides A-C, bioactive lipopeptides from the deep-sea sponge Aaptos ciliata.

PubMed

Nakao, Yoichi; Kawatsu, Shizuka; Okamoto, Chikane; Okamoto, Masaaki; Matsumoto, Yoshitsugu; Matsunaga, Shigeki; van Soest, Rob W M; Fusetani, Nobuhiro

2008-03-01

Three lipopeptides, ciliatamides A-C ( 1- 3), were isolated from the deep-sea sponge Aaptos ciliata, and their structures were elucidated on the basis of spectroscopic and chemical methods. Ciliatamides A ( 1) and B ( 2) were found to be antileishmanial, while 2 also exhibited marginal cytotoxicity to HeLa cells.

Novel cytotoxic, polyprenylated heptacyclic xanthonoids from Indonesian Garcinia gaudichaudii (Guttiferae).

PubMed

Xu, Y J; Yip, S C; Kosela, S; Fitri, E; Hana, M; Goh, S H; Sim, K Y

2000-11-30

[reaction: see text] The structures of novel gaudichaudiic acids F-I (1-4), isolated from the bark of Indonesian Garcinia gaudichaudii, have been elucidated by detailed spectral analysis. Gaudichaudiic acid I (4) is probably derived from 1 as a result of allylic oxidation at C-24 and C-21, followed by aromatization.

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.

A new phenylpropanoid glycoside from Jasminum subtriplinerve Blume.

PubMed

Huong, Nguyen Thi Hong; Cu, Nguyen Khac Quynh; Quy, Trinh Van; Zidorn, Christian; Ganzera, Markus; Stuppner, Hermann

2008-01-01

From the ethyl acetate extract of the aerial parts of Jasminum subtriplinerve Blume (Oleaceae), 6'-O-menthiafoloylverbascoside (1), rutin (2), isoverbascoside (4), isooleoverbascoside (6), apiosylverbascoside (7), astragalin (9), isoquercitrin (10), and verbascoside (11) were isolated. Their structures were elucidated by extensive MS and NMR spectroscopy. Amongst 6'-O-menthiafoloylverbascoside (1) is a new phenylpropanoid glycoside.

Cylindol A, a novel biphenyl ether with 5-lipoxygenase inhibitory activity, and a related compound from Imperata Cylindrica.

PubMed

Matsunaga, K; Ikeda, M; Shibuya, M; Ohizumi, Y

1994-09-01

Cylindol A [1] and B [2], two novel substances, have been isolated from Imperata cylindrica, and their structures have been elucidated on the basis of their spectral data coupled with chemical evidence and total synthesis. Cylindol A [1] showed 5-lipoxygenase inhibitory activity.

Medicinal flowers. XXX. Eight new glycosides, everlastosides F-M, from the flowers of Helichrysum arenarium.

PubMed

Morikawa, Toshio; Wang, Li-Bo; Ninomiya, Kiyofumi; Nakamura, Seikou; Matsuda, Hisashi; Muraoka, Osamu; Wu, Li-Jun; Yoshikawa, Masayuki

2009-08-01

Eight new glycosides, everlastosides F (1), G (2), H (3), I (4), J (5), K (6), L (7), and M (8), were isolated from the methanolic extract of the flowers of Helichrysum arenarium. Their structures were elucidated on the basis of chemical and physicochemical evidence.

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.

A new phenolic glycoside from the stem of Dendrobium nobile.

PubMed

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

2017-05-01

A new phenolic glycoside dendroside (1), together with seven known compounds (2-8) were isolated from the stems of Dendrobium nobile. The structures of these compounds were elucidated using comprehensive spectroscopic methods. The inhibitory activities of all compounds against three cancer cell lines HeLa, MCF-7 and A549 were evaluated.

Application of comprehensive NMR-based analysis strategy in annotation, isolation and structure elucidation of low molecular weight metabolites of Ricinus communis seeds.

PubMed

Vučković, Ivan; Rapinoja, Marja-Leena; Vaismaa, Matti; Vanninen, Paula; Koskela, Harri

2016-01-01

Powder-like extract of Ricinus communis seeds contain a toxic protein, ricin, which has a history of military, criminal and terroristic use. As the detection of ricin in this "terrorist powder" is difficult and time-consuming, related low mass metabolites have been suggested to be useful for screening as biomarkers of ricin. To apply a comprehensive NMR-based analysis strategy for annotation, isolation and structure elucidation of low molecular weight plant metabolites of Ricinus communis seeds. The seed extract was prepared with a well-known acetone extraction approach. The common metabolites were annotated from seed extract dissolved in acidic solution using (1)H NMR spectroscopy with spectrum library comparison and standard addition, whereas unconfirmed metabolites were identified using multi-step off-line HPLC-DAD-NMR approach. In addition to the common plant metabolites, two previously unreported compounds, 1,3-digalactoinositol and ricinyl-alanine, were identified with support of MS analyses. The applied comprehensive NMR-based analysis strategy provided identification of the prominent low molecular weight metabolites with high confidence. Copyright © 2015 John Wiley & Sons, Ltd.

Isolation and Structure Elucidation, Molecular Docking Studies of Screlotiumol from Soil Borne Fungi Screlotium rolfsii and their Reversal of Multidrug Resistance in Mouse Lymphoma Cells.

PubMed

Ahmad, Bashir; Rizwan, Muhammad; Rauf, Abdur; Raza, Muslim; Azam, Sadiq; Bashir, Shumaila; Molnar, Joseph; Csonka, Akos; Szabo, Diana

2016-01-01

A new compound namely (13-(3,3-dihydroxypropyl)-1,6-dihydroxy-3,4-dihydro-1H-isochromen-8(5H)-one (1) was isolated from an ethyl acetate extract of the borne fungi Screlotium rolfsii. Its chemical structure was elucidated by spectroscopic analysis. Screlotiumol 1 were evaluated for their effects on the reversion of multidrug resistant (MDR) mediated by P-glycoprotein (P-gp) of the soil borne fungi. The multidrug resistant P-glycoprotein is a target for chemotherapeutic drugs in cancer cells. In the present study rhodamine-123 exclusion screening test on human mdr1 gene transfected mouse gene transfected L5178 and L5178Y mouse T-cell lymphoma which showed excellent MDR reversing effect in a dose dependent manner against mouse T-lymphoma cell line. Moreover, molecular docking studies of compound-1 also showed better results as compared with the standard. Therefore the preliminary results obtained from this study suggest that screlotiumol 1 could be used as a potential agent for the treatment of cancer.

ISOLATION OF NOVEL PARA-PENTYL PHENYL BENZOATE FROM MONDIA WHITEI. (HOOK.F.) SKEELS (PERIPLOCACEAE), ITS STRUCTURE, SYNTHESIS AND NEUROPHARMACOLOGICAL EVALUATION.

PubMed

Bamigboye J, Taiwo; Josephine Y, Osasan; Olujide O, Olubiyi; A, Oyemitan Idris; Shakir A M, Atoyebi; Mark R J, Elsegood; Raymond C F, Jones

2017-01-01

Mondia whitei L. (Hook. F.) Skeels (Periplocaceae) is a medicinal plant used locally in managing pain, fever, loss of appetite and as aphrodiasc in the South-Western states of Nigeria. However, the fruit is consumed habitually in the South-Eastern states of Nigeria, leading to speculation that it may possess some central nervous system effect but which has not been scientifically investigated, hence this study. Fresh fruits of Mondia whitei were collected and identified by a taxonomist. They were chopped into small pieces and extracted with absolute ethanol. The crude extract was subjected to various chromatographic techniques to isolate a novel compound whose structure was elucidated from the analysis of the crystal data and by extensive use of spectroscopy. The structure was confirmed by synthesis. The compound was subjected to anxiolytic and sedative activity assay. Computational analysis of the receptor binding event of isolated compound at the gamma amino butyric acid A receptor was also evaluated. The structure of the compound was elucidated as para pentyl phenyl benzoate. The neuropharmacological evaluation of the compound indicated significant (p<0.05) depression of the central nervous system. The binding characteristics of the compound to gamma amino butyric acid A receptors appears to be more favorable than those obtained for gamma amino butyric acid, chlorpromazine, benzamidine, and is comparable with the affinity obtained for pentobarbitone and diazepam. These present data provide evidence for the role of para pentyl phenyl benzoate in the habitual consumption of the fruit as well as its central nervous system activities.

Bioactive natural compounds from the plant endophytic fungi Pestalotiopsis spp.

PubMed

Wang, Kuiwu; Lei, Jinxiu; Wei, Jiguang; Yao, Nan

2012-11-01

The plant-endophytic strains of the fungus Pestalotiopsis (Amphisphaeriaceae) are distributed throughout the world. Previous chemical investigation of members of the genus resulted in the discovery of various bioactive secondary metabolites including chromones, cytosporones, polyketides, terpenoids and coumarins with diverse structural features. The present report reviews the papers, which have appeared in the literature till now, concerning the isolation, structural elucidation, and biological activities of the secondary metabolites from Pestalotiopsis species.

A bis-bithiophene from Tridax procumbens L. (Asteraceae).

PubMed

Ali, Muhammad Shaiq; Jahangir, Muhammad

2002-08-01

The ethyl acetate soluble part of hexane extract of Tridax procumbens yielded a new bis-bithiophene named tridbisbithiophene along with four known terpenoids: taraxasteryl acetate, beta-amyrenone, lupeol and oleanolic acid, which have never been reported so far from Tridax procumbens. The structures of all the isolated constituents were elucidated with the aid of 1D-NMR spectroscopy whereas, the structure of new constituent tridbisbithiophene was confirmed via COSY and HMBC interactions.

Janthinocins A, B and C, novel peptide lactone antibiotics produced by Janthinobacterium lividum. II. Structure elucidation.

PubMed

Johnson, J H; Tymiak, A A; Bolgar, M S

1990-08-01

The structures of janthinocins A, B and C, three novel macrocyclic peptide lactone antibiotics isolated from fermentations of Janthinobacterium lividum, were determined. The janthinocins are of particular interest because they contain three amino acid residues that have not previously been reported in natural products: Each contains erythro-beta-hydroxy-D-leucine while janthinocins A and B also contain beta-hydroxytryptophan and beta-ketotryptophan, respectively.

Diterpenoid glycosides from the bitter fern Gleichenia quadripartita.

PubMed

Socolsky, Cecilia; Asakawa, Yoshinori; Bardón, Alicia

2007-12-01

Fifteen new diterpenoid glycosides (1a-n, 2) were isolated from an Argentine collection of the bitter fern Gleichenia quadripartita along with the known flavonoid glycoside afzelin. Structure elucidation was accomplished by 1D and 2D NMR spectroscopy and by high-resolution MS analyses. In addition, X-ray crystallographic analysis of a monocrystal of 1a as well as chemical derivatization of 1h and 1m were performed to confirm their structures.

[Triterpenes and triterpene glycosides from aerial part of Paraboea glutinosa].

PubMed

Wang, Xiaoqin; Peng, Yong; Xu, Lijia; Xiao, Wei; Xiao, Peigen; Liu, Yong

2009-05-01

To investigate the chemical constituents from aerial part of Paraboea glutinosa. The compounds were isolated with silica gel, Sephadex LH-20 column chromatography and their structures were elucidated by means of spectral data analysis. Five compounds were isolated and identified as 2alpha, 3beta, 19alpha, 24-tetrahydroxyurs-12-en-28-oate(24-hydroxytormentic acid,1), glucosyl-2alpha, 3beta, 19alpha, 24-tetrahydroxyurs-12-en-28-oate (24-hydroxytormentic acid ester glucoside,2), 28-O-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl-24-hydroxytormentic acid (3), beta-sitosterol (4), daucosterol (5). All these compounds were isolated from the genus Paraboea for the first time.

[Study on the chemical constituents from Cyathea spinulosa].

PubMed

Jiang, Jian-Shuang; Zhan, Zhi-Lai; Feng, Zi-Ming; Yang, Ya-Nan; Zhang, Pei-Cheng

2012-04-01

To study the chemical constituents from Cyathea spinulosa. Compounds were isolated by chromatographic techniques. Their structures were elucidated by spectral methods. Eight compounds were isolated from the ethanol extract of Cyathea spinulosa and identified as stigmast-4-ene-3,6-dione (1), stigmast-3,6-dione (2), ergosterol (3), protocatechuic aldehyde (4), 1-O-beta-D-glucopyranosyl-(2S,3R,4E,8Z)-2-[(2-hydroxyoctadecanoyl) amido]-4,8- octadecadiene-1,3-diol (5), (2S,3S, 4R)-2-[(2'R) -2'-hydroxytetracosanoylamino]-1,3,4-octadecanetriol (6), beta-sitosterol (7), daucosterol (8). Compounds 1-6 are isolated from this plant for the first time.

Cyclodepsipeptides and other O-containing heterocyclic metabolites from Beauveria felina EN-135, a marine-derived entomopathogenic fungus.

PubMed

Du, Feng-Yu; Li, Xiao-Ming; Zhang, Peng; Li, Chun-Shun; Wang, Bin-Gui

2014-05-13

Bioassay-guided fractionation of a culture extract of Beauveria felina EN-135, an entomopathogenic fungus isolated from a marine bryozoan, led to the isolation of a new cyclodepsipeptide, iso-isariin D (1); two new O-containing heterocyclic compounds that we have named felinones A and B (2 and 3); and four known cyclodepsipeptides (4-7). The structures were elucidated via spectroscopic analysis, and the absolute configurations of 1 and 2 were determined using single-crystal X-ray diffraction and CD, respectively. All isolated compounds were evaluated for antimicrobial activity and brine-shrimp (Artemia salina) lethality.

[Phenanthrene constituents from rhizome of Arundina graminifolia].

PubMed

Liu, Mei-feng; Ding, Yi; Zhang, Dong-ming

2005-03-01

To isolate and elucidate the constituents from rhizome of Arundina graminifolia. Theconstituents were extracted with 95% alcohol and isolated by chromatography on silica gel, Sephedax LH-20. The structures were determined by UV, IR, NMR and MS spectral analysis. Five phenanthrene constituents were identified as 7-hydroxy-2, 4-dimethoxy-9, 10-dihydrophenanthrene( I ), 4, 7-dihydroxy-2-methoxy-9, 10-dihydrophenanthrene ( II ), 2, 7-dihydroxy-4-methoxy-9, 10-dihydrophenanthrene ( III ), 7-hydroxy-2-methoxyphenanthrene-1,4-dione ( IV ), 7-hydroxy-2-methoxy-9, 10-dihydrophenanthrene-1,4-dione (V), respectively. All compounds were isolated from rhizome of A. graminifolia for the first time.

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.

Lucidumol D, a new lanostane-type triterpene from fruiting bodies of Reishi (Ganoderma lingzhi).

PubMed

Satria, Dedi; Amen, Yhiya; Niwa, Yasuharu; Ashour, Ahmed; Allam, Ahmed E; Shimizu, Kuniyoshi

2018-02-19

A new lanostane-type triterpenoid, lucidumol D (1) was isolated from the fruiting bodies of Ganoderma lingzhi. Its structure was elucidated on the basis of extensive 1D- and 2D-NMR studies as well as mass spectrometry. The cytotoxicity of lucidumol D against proliferation of several cancer cells were assayed by using MTT method and the obtained result suggested selective anti-proliferative and cytotoxic effects against MCF-7, HepG2, HeLa, Caco-2, and HCT-116. In comparison to lucidumol C (2) isolated previously by our group, the structure-activity relationship indicated that carbonyl function at C-11 is necessary to enhance the cytotoxicity.

Isolation and identification of new anthraquinones from Rhamnus alaternus L and evaluation of their free radical scavenging activity.

PubMed

Ben Ammar, Rebai; Miyamoto, Tomofumi; Chekir-Ghedira, Leila; Ghedira, Kamel; Lacaille-Dubois, Marie-Aleth

2018-03-13

From the butanolic and the ethyl acetate extracts of Rhamnus alaternus L root bark and leaves, three new anthraquinone glycosides, alaternosides A-C (1,4,6,8 tetrahydroxy-3 methyl anthraquinone 1-O-ß-D-glucopyranosyl-4,6-di-O-α-L-rhamnopyranoside (1); 1,2,6,8 tetrahydroxy-3 methyl anthraquinone 8-O-ß-D-glucopyranoside (2) and 1, 6 dihydroxy-3 methyl 6 [2'-Me (heptoxy)] anthraquinone (3)) were isolated and elucidated together with the two known anthraquinone glycosides, Physcion-8-O-rutinoside (4) and emodin-6-O-α-L-rhamnoside (5) as well as with the known kaempferol-7-methylether (6), β-sitosterol (7) and β-sitosterol-3-O-glycoside (8). Their chemical structures were elucidated using spectroscopic methods (1D-, 2D-NMR and FAB-MS). Free radical scavenging activity of the isolated compounds was evaluated by their ability to scavenge DPPH . free radicals. Compounds (3), (4) and (6) showed the highest activity with IC 50 values of 9.46, 27.68 and 2.35 μg/mL, respectively.

[Study on Megastigmane Glycosides and Lignan Constituents from Leaves of Psidium littorale].

PubMed

Peng, Cai-ying; Liu, Jian-qun; Shu, Ji-cheng; Zhang, Rui

2014-12-01

To study the chemical constituents of the leaves of Psidium littorale. The constituents were isolated with silica gel column chromatography and the structures of these compounds were elucidated on the basis of spectral analysis. Four megastigmane glycosides and three lignans were isolated and their structures were identified as Bridelionoside B(1), Euodinoside E(2), (3S,5R,6R,7E,9S)-Megastignan-7-ene-3,5,6,9-tetrol 9-O-β-D-glucopyranoside (3), Bridelionoside C(4), (--)-Isolaricires-inol 3-α-O-β-D-glucopyranoside (5), (--)-5'-methoxy-Isolariciresinol 3-α-O-β-D-glucopyranoside (6) and dihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside(7). Compounds 1-7 are isolated from this plant for the first time. The results have provided the scientific basis for further exploitation of Psidium littoratle.

Phytochemical study of Helichrysum italicum (Roth) G. Don: Spectroscopic elucidation of unusual amino-phlorogucinols and antimicrobial assessment of secondary metabolites from medium-polar extract.

PubMed

D'Abrosca, Brigida; Buommino, Elisabetta; Caputo, Pina; Scognamiglio, Monica; Chambery, Angela; Donnarumma, Giovanna; Fiorentino, Antonio

2016-12-01

Three unusual amino-phloroglucinols, named helichrytalicines A-C, along with seventeen known compounds including acetophenones, tremetrone derivatives, low-molecular weight phenols, flavonol glucosides, have been isolated from the medium-polar extract of Helichrysum italicum (Roth) G. Don, a medicinal plant typical of the Mediterranean vegetation. The structures of the compounds have been elucidated based on extensive 2D-NMR spectroscopic analyses, including COSY, TOCSY, HSQC, CIGAR-HMBC, H2BC and HSQC-TOCSY, along with Q-TOF HRMS 2 analysis. Stereostructure of the new compounds has been elucidated by Mosher's method and NOESY experiment. Antimicrobial properties against Staphylococcus epidermidis of selected compounds have been evaluated. Copyright © 2016 Elsevier Ltd. All rights reserved.

Quinones from Heliotropium ovalifolium.

PubMed

Guntern, A; Ioset, J R; Queiroz, E F; Foggin, C M; Hostettmann, K

2001-10-01

Two new benzoquinones, heliotropinones A and B, have been isolated from the aerial parts of Heliotropium ovalifolium. Their structures were elucidated by spectrometric methods including high resolution electrospray ionization (ESI-HR), EI mass spectrometry, 1H, 13C and 2D NMR experiments. The two quinones demonstrated antifungal activities against Cladosporium cucumerinum and Candida albicans as well as antibacterial activity against Bacillus subtilis.

New megastigmane glycoside and aromadendrane derivative from the aerial part of Piper elongatum.

PubMed

Masuoka, Chikako; Ono, Masateru; Ito, Yasuyuki; Okawa, Masafumi; Nohara, Toshihiro

2002-10-01

A new megastigmane glycoside, called pipeloside A, and a new aromadendrane type sesquiterpenoid, pipelol A, were isolated from the MeOH extract of the aerial part of Piper elongatum VAHL. along with a known megastigmane glycoside, byzantionoside B. The structures of these compounds were elucidated on the basis of spectroscopic data and chemical evidence.

Pyrano-isoflavones with erectile-dysfunction activity from Eriosema kraussianum.

PubMed

Drewes, Siegfried E; Horn, Marion M; Munro, Orde Q; Dhlamini, Jabu T B; Meyer, J J Marion; Rakuambo, N Christopher

2002-04-01

Five pyrano-isoflavones have been isolated from the rootstock of Eriosema kraussianum N. E. Br (Papilionaceae). Spectral data and single crystal X-ray analyses were used for structural elucidation. The most active of the compounds had an activity of 75% of that found in Viagra in the erectile dysfunction test on rabbit penile smooth muscle.

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.

Ophirapstanol trisulfate, a new biologically active steroid sulfate from the deep water marine sponge Topsentia ophiraphidites.

PubMed

Gunasekera, S P; Sennett, S H; Kelly-Borges, M; Bryant, R W

1994-12-01

Ophirapstanol trisulfate [1], a new steroid trisulfate related to sokotrasterol trisulfate was isolated from a deep water marine sponge Topsentia ophiraphidites. Compound 1 exhibited significant inhibition in the guanosine diphosphate/G-protein RAS exchange assay. The structure elucidation of 1 and ophirapstanol [2] by nmr spectroscopy is described.

Guaiane dimers from Xylopia vielana.

PubMed

Kamperdick, Christine; Phuong, Nguyen Minh; Adam, Günter; Van Sung, Tran

2003-10-01

From the leaves of Xylopia vielana (Annonaceae) two dimeric guaianes named vielanins D and E were isolated and structurally elucidated by mass and NMR spectroscopy. Vielanin D and E consist of bridged ring systems formally representing the Diels-Alder products from the hypothetical guaiane-type monomers. Due to a hemiketal function at C-8' both compounds occurred as epimeric mixtures.

Three new constituents, latifolinal, latifolidin and cordicinol, from the fruits and leaves of Cordia latifolia.

PubMed

Siddiqui, Bina S; Perwaiz, Sobiya; Begum, Sabira; Ali, S Tariq

2010-01-01

Isolation and structure elucidation of three new natural constituents are reported. These include a new substituted furfuryl ester of stearic acid, latifolinal (1), and two aromatic compounds, latifolidin (2) and cordicinol (3). Compounds 1 and 2 were obtained from the dried fruits and compound 3 from the leaves of Cordia latifolia.

Sebestenoids A-D, BACE1 inhibitors from Cordia sebestena.

PubMed

Dai, Jingqiu; Sorribas, Analia; Yoshida, Wesley Y; Williams, Philip G

2010-12-01

Bioassay-guided fractionation of an extract prepared from the fruits of Cordia sebestena led to the isolation of sebestenoids A-D (1-4). Their structures were elucidated on the basis of extensive NMR experiments and mass spectroscopic measurements. Compounds 1-4 exhibited moderate inhibition of the aspartic protease BACE1. Copyright © 2010 Elsevier Ltd. All rights reserved.

Sebestenoids A-D, BACE1 inhibitors from Cordia sebestena

PubMed Central

Dai, Jingqiu; Sorribas, Analia; Yoshida, Wesley Y.; Williams, Philip G.

2010-01-01

Bioassay-guided fractionation of an extract prepared from the fruits of Cordia sebestena has led to the isolation of sebestenoids A-D (1-4). The structures of these new phenylpropanoid esters were elucidated on the basis of extensive NMR experiments and mass spectroscopic measurements. Compounds 1-4 exhibited moderate inhibition of the aspartic protease BACE1. PMID:20952040

Thermophilic Beta-Glycosidase

NASA Technical Reports Server (NTRS)

Grogan, Dennis W.

1992-01-01

Report describes identification of thermophilic Beta-glycosidase enzyme from isolate of Sulfolobus solfataricus, sulfur-metabolizing archaebacteria growing aerobically and heterotrophically to relatively high cell yields. Enzyme useful in enzymatic conversion of cellulose to D-glucose and important in recycling of biomass. Used for removal of lactose from milk products. Offers promise as model substance for elucidation of basic principles of structural stabilization of proteins.

[Alkaloids and lignans from stems of Piper betle].

PubMed

Huang, Xiangzhong; Yin, Yan; Huang, Wenquan; Sun, Kuizong; Cheng, Chunmei; Bai, Lian; Dai, Yun

2010-09-01

Alkaloids and lignans from the stems of Piper betle were studied. Compounds were isolated and purified by repeated silica gel, reverse phase silica gel, Sephadex LH-20 column chromatography and preparative thin layer chromatography. The structures were elucidated on the basis of spectral analysis. From the ethyl acetate soluble fractions of the 70% acetone extract, ten compounds were isolated and identified as piperine (1), pellitorine (2), N-isobutyl-2E,4E-dodecadienamide (3), dehydropipernonaline (4), piperdardine (5), piperolein-B (6), guineensine (7), (2E,4E)-N-isobutyl-7-(3',4'-methylenedioxyphenyl)-2,4-heptadienamide (8), syringaresinol-O-beta-D-glucopyranoside (9),pinoresinol (10). All Compounds were isolated from the plant for the first time, and compounds 9 and 10 were isolated firstly from the genus.

Helicusin E, isochromophilone X and isochromophilone XI: new chloroazaphilones produced by the fungus Bartalinia robillardoides strain LF550.

PubMed

Jansen, Nils; Ohlendorf, Birgit; Erhard, Arlette; Bruhn, Torsten; Bringmann, Gerhard; Imhoff, Johannes F

2013-03-12

Microbial studies of the Mediterranean sponge Tethya aurantium led to the isolation of the fungus Bartalinia robillardoides strain LF550. The strain produced a number of secondary metabolites belonging to the chloroazaphilones. This is the first report on the isolation of chloroazaphilones of a fungal strain belonging to the genus Bartalinia. Besides some known compounds (helicusin A (1) and deacetylsclerotiorin (2)), three new chloroazaphilones (helicusin E (3); isochromophilone X (4) and isochromophilone XI (5)) and one new pentaketide (bartanolide (6)) were isolated. The structure elucidations were based on spectroscopic analyses. All isolated compounds revealed different biological activity spectra against a test panel of four bacteria: three fungi; two tumor cell lines and two enzymes.

[Studies on chemical constituents from leaves of Vaccinium bracteatum].

PubMed

Li, Zeng-Liang; Zhang, Lin; Tian, Jing-Kui; Zhou, Wen-Ming

2008-09-01

To investigate the chemical constituents from the leaves of Vaccinium bracteatum. Many column chromatographic techniques were used for the isolation and separation of chemical constituents. Their structures were elucidated on the basis of spectral analysis and chemical evidences. Twelve compounds were isolated from the plant, and they were identified as chrysoeriol (1), scopoletin (2), trans-p-hydroxycinnamic acid (3), trans-p-hydroxycinnamic acid ethyl ester (4), cafeic acid ethyl ester (5), beta-sitosterol (6), iuteolin (7), quercetin (8), esculetin (9), cafeic acid (10), isolariciresinol-9-O-beta-D-xyloside (11), 10-O-trans-p-coumaroylsandoside (12). Compounds 4, 5, 11, 12 were isolated from the genus Vaccinium for the first time, and compounds 1, 2, 9, 10 were isolated from this plant for the first time.

Solid state compatibility study and characterization of a novel degradation product of tacrolimus in formulation.

PubMed

Rozman Peterka, Tanja; Grahek, Rok; Hren, Jure; Bastarda, Andrej; Bergles, Jure; Urleb, Uroš

2015-06-10

Tacrolimus is macrolide drug that is widely used as a potent immunosuppressant. In the present work compatibility testing was conducted on physical mixtures of tacrolimus with excipients and on compatibility mixtures prepared by the simulation of manufacturing process used for the final drug product preparation. Increase in one major degradation product was detected in the presence of magnesium stearate based upon UHPLC analysis. The degradation product was isolated by preparative HPLC and its structure was elucidated by NMR and MS studies. Mechanism of the formation of this degradation product is proposed based on complementary degradation studies in a solution and structural elucidation data. The structure was proven to be alpha-hydroxy acid which is formed from the parent tacrolimus molecule through a benzilic acid type rearrangement reaction in the presence of divalent metallic cations. Degradation is facilitated at higher pH values. Copyright © 2015 Elsevier B.V. All rights reserved.

Multihydroxylation of ursolic acid by Pestalotiopsis microspora isolated from the medicinal plant Huperzia serrata.

PubMed

Fu, Shao-bin; Yang, Jun-shan; Cui, Jin-long; Meng, Qing-feng; Feng, Xu; Sun, Di-An

2011-10-01

The structural modification of ursolic acid by an endophytic fungus Pestalotiopsis microspora, isolated from medicinal plant Huperzia serrata was reported for the first time. The structure diversity was very important for the SAR study of ursolic acid and its derivatives. Incubation of ursolic acid 1 with P. microspora afforded four metabolites: 3-oxo-15α, 30-dihydroxy-urs-12-en-28-oic acid (2), 3β, 15α-dihydroxy-urs-12-en-28-oic acid (3), 3β, 15α, 30- trihydroxy-urs-12-en-28-oic acid (4) and 3,4-seco-ursan-4,30-dihydroxy-12-en-3,28-dioic acid (5). All products were new compounds and their structures elucidation was mainly based on the spectroscopic data. Copyright © 2011 Elsevier B.V. All rights reserved.

[Chemical constituents of Changium smyrnioides].

PubMed

Ren, Dong-chun; Qian, Shi-hui; Yang, Nian-yun; Xie, Ning; Duan, Jin-ao

2008-01-01

To study chemical constituents of Changium smyrnioides Wolff. The chemical components were isolated and purified by silica gel column and recrystallization. The chemical structures were elucidated on the basis of physico-chemical properties and spectral data. Ten compounds were isolated and identified as lignoceric acid (1), beta-sitosterol (2), stigmasterol (3), 5-hydroxy-8-methoxypsoralen (4), glycerylmonopalmitate (5), L-pyroglutamic acid (6), succinic acid (7), vanillic acid-4-O-beta-D-glucopyranoside (8 ), vanillic acid (9), daucosterol (10). Compounds 1, 4, 5, 6, 8 and 9 are obtained from the plant for the first time.

[Studies on chemical constituents from seeds of Euryale ferox].

PubMed

Sun, Hai-lin; Zhang, Ya-qiong; Xie, Xiao-yan; Che, Yan-yun

2014-11-01

To study the chemical constituents from the seeds of Euryale ferox. The chemical constituents were isolated by silica gel column, Sephadex LH-20 and their structures were identified by physico-chemical and spectral analysis. Seven compounds were purified from the 95% ethanol extract. These constituents were elucidated as protocatechuic acid (1), gallic acid (2), gallic acid ethyl ester(3),5 ,7-dihydroxychromone(4), β-sitosterol(5), daucosterol(6), and 5,7-dihydroxy-6,4'-dimethoxyflavone(7), respectively. All compounds are isolated from this plant for the first time.

[Secondary metabolites of a marine mangrove fungus (Penicillium sp. no. 2556) from South China Sea].

PubMed

Li, Chun-Yuan; Ding, Wei-Jia; Shao, Chang-Lun; She, Zhi-Gang; Lin, Yong-Cheng

2008-07-01

The metabolites of a marine mangrove fungus (Penicillium sp. No. 2556) were studied in this paper and six compounds were isolated from the fermentation liquid. Their structures were elucidated by spectroscopy methods as Sch54796 (1), Sch54794 (2), 4-hydroxybenzoic acid (3), urail (4), succinic acid (5), Vermopyrone (6). Among them, compounds 1, 2 and 6 were firstly isolated from Penicillium sp., Coumpounds 1 and 2 remarkably inhibited the growth of cancer cell lines hep2 and hepG2.

Two new lignans from Saururus chinensis and their DGAT inhibitory activity.

PubMed

Li, Na; Tuo, Zhen-Dong; Qi, Shi-Zhou; Xing, Shan-Shan; Lee, Hyun-Sun; Chen, Jian-Guang; Cui, Long

2015-03-01

Two new lignans were isolated from Saururus chinensis, along with eight known compounds. Their structures were elucidated on the basis of spectroscopic and physico-chemical analyses. All the isolates were evaluated for in vitro inhibitory activity against DGAT1 and DGAT2. Among them, compounds 2, 3, 5 and 7 were found to exhibit selective inhibitory activity on DGAT1 with IC50 values ranging from 44.3±1.5 to 87.5±1.3μM. Copyright © 2014 Elsevier B.V. All rights reserved.

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.

Guignardones P-S, New Meroterpenoids from the Endophytic Fungus Guignardia mangiferae A348 Derived from the Medicinal Plant Smilax glabra.

PubMed

Sun, Zhang-Hua; Liang, Fa-Liang; Wu, Wen; Chen, Yu-Chan; Pan, Qing-Ling; Li, Hao-Hua; Ye, Wei; Liu, Hong-Xin; Li, Sai-Ni; Tan, Guo-Hui; Zhang, Wei-Min

2015-12-21

Four new meroterpenoids, guignardones P-S (1-4), and three known analogues (5-7) were isolated from the endophytic fungal strain Guignardia mangiferae A348. Their structures were elucidated on the basis of spectroscopic analysis and single crystal X-ray diffraction. All the isolated compounds were evaluated for their inhibitory effects on SF-268, MCF-7, and NCI-H460 human cancer cell lines. Compounds 2 and 4 exhibited weak inhibitions of cell proliferation against MCF-7 cell line.

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.

Triterpenoid Saponins from the Seeds of Aesculus chinensis and Their Cytotoxicities.

PubMed

Cheng, Jin-Tang; Chen, Shi-Tao; Guo, Cong; Jiao, Meng-Jiao; Cui, Wen-Jin; Wang, Shu-Hui; Deng, Zhe; Chen, Chang; Chen, Sha; Zhang, Jun; Liu, An

2018-02-01

Six new triterpenoid saponins, aesculusosides A-F (1-6), together with 19 known ones, were isolated from the seeds of Aesculus chinensis. The new structures were elucidated through extensive spectroscopic analyses and by comparison with previously reported data. Some of the isolates were evaluated for their cytotoxic activities against MCF-7 cell line by an MTT assay, and compounds 15, 16, 19, and 23-25 exhibited inhibitory activities against MCF-7 with IC 50 values ranging from 7.1 to 31.3 μM.

Cyclic 3-alkyl pyridinium alkaloid monomers from a New Zealand Haliclona sp. marine sponge.

PubMed

Damodaran, Vidhiya; Ryan, Jason L; Keyzers, Robert A

2013-10-25

Bioassay and NMR approaches have been used to guide the isolation of one known and two new cyclic 3-alkyl pyridinium alkaloid (3-APA) monomers from the New Zealand marine sponge Haliclona sp. The new compounds, dehydrohaliclocyclins C (3) and F (4), are the first reported examples of cyclic 3-APA monomers with unsaturation in the alkyl chain. The known compound haliclocyclin C (2) was also isolated from a mixture with 4. The structures of compounds 2-4 were elucidated using NMR spectroscopy, mass spectrometry, and chemical degradation.

[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.

Two novel dicarboxylic Acid derivatives and a new dimeric hydrolyzable tannin from walnuts.

PubMed

Ito, Hideyuki; Okuda, Takahiro; Fukuda, Toshiyuki; Hatano, Tsutomu; Yoshida, Takashi

2007-02-07

In addition to the 16 previously reported polyphenols including 3 new ellagitannins, 2 novel dicarboxylic acid derivatives, glansreginins A (1) and B (2), and a new dimeric hydrolyzable tannin, glansrin D (3), were isolated, together with 15 known compounds from walnuts, the seeds of Juglans regia. The structures of the new compounds were elucidated on the basis of 1D- and 2D-NMR analyses and chemical data. The antioxidant effect of these isolates was also evaluated by SOD-like and DPPH radical scavenging activities.

Alkaloids from aerial parts of Houttuynia cordata and their anti-inflammatory activity.

PubMed

Ahn, Jongmin; Chae, Hee-Sung; Chin, Young-Won; Kim, Jinwoong

2017-06-15

New alkaloids, houttuynamide B and C (1, 2) and houttuycorine (14), were isolated from the aerial parts of Houttuynia cordata Thunb. in addition to eighteen known alkaloids. Their structures were elucidated through extensive spectroscopic analysis. All the isolates were tested for their inhibitory activity against NO production in RAW 264.7 cells stimulated by LPS. Of the tested compounds, compound 15 showed the most potent anti-inflammatory activity with an IC 50 value of 8.7μM. Copyright © 2017 Elsevier Ltd. All rights reserved.

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.

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.

Comparison of genetic diversity and population structure between two Schistosoma japonicum isolates--the field and the laboratory.

PubMed

Bian, Chao-Rong; Gao, Yu-Meng; Lamberton, Poppy H L; Lu, Da-Bing

2015-06-01

Schistosomiasis japonicum is one of the most important human parasitic diseases, and a number of studies have recently elucidated the difference in biological characteristics of S. japonicum among different parasite isolates, for example, between the field and the laboratory isolates. Therefore, the understanding of underlying genetic mechanism is of both theoretical and practical importance. In this study, we used six microsatellite markers to assess genetic diversity, population structure, and the bottleneck effect (a sharp reduction in population size) of two parasite populations, one field and one laboratory. A total of 136 S. japonicum cercariae from the field and 86 from the laboratory, which were genetically unique within single snails, were analyzed. The results showed bigger numbers of alleles and higher allelic richness in the field parasite population than in the laboratory indicating lower genetic diversity in the laboratory parasites. A bottleneck effect was detected in the laboratory population. When the field and laboratory isolates were combined, there was a clear distinction between two parasite populations using the software Structure. These genetic differences may partially explain the previously observed contrasted biological traits.

Isolation and purification of a new kalimantacin/batumin-related polyketide antibiotic and elucidation of its biosynthesis gene cluster.

PubMed

Mattheus, Wesley; Gao, Ling-Jie; Herdewijn, Piet; Landuyt, Bart; Verhaegen, Jan; Masschelein, Joleen; Volckaert, Guido; Lavigne, Rob

2010-02-26

Kal/bat, a polyketide, isolated to high purity (>95%) is characterized by strong and selective antibacterial activity against Staphylococcus species (minimum inhibitory concentration, 0.05 microg/mL), and no resistance was observed in strains already resistant to commonly used antibiotics. The kal/bat biosynthesis gene cluster was determined to a 62 kb genomic region of Pseudomonas fluorescens BCCM_ID9359. The kal/bat gene cluster consists of 16 open reading frames (ORF), encoding a hybrid PKS-NRPS system, extended with trans-acting tailoring functions. A full model for kal/bat biosynthesis is postulated and experimentally tested by gene inactivation, structural confirmation (using NMR spectroscopy), and complementation. The structural and microbiological study of biosynthetic kal/bat analogs revealed the importance of the carbamoyl group and 17-keto group for antibacterial activity. The mechanism of self-resistance lies within the production of an inactive intermediate, which is activated in a one-step enzymatic oxidation upon export. The genetic basis and biochemical elucidation of the biosynthesis pathway of this antibiotic will facilitate rational engineering for the design of novel structures with improved activities. This makes it a promising new therapeutic option to cope with multidrug-resistant clinical infections. Copyright 2010 Elsevier Ltd. All rights reserved.

A new pyrimidinedione derivative from the gorgonian coral Verrucella umbraculum.

PubMed

Huang, Riming; Peng, Yan; Zhou, Xuefeng; Fu, Manqin; Tian, Shuai; Liu, Yonghong

2013-03-01

A new pyrimidinedione derivative, 9-acetyl-1,3,7-trimethyl-pyrimidinedione (1), was isolated from the gorgonian coral Verrucella umbraculum, together with two known compounds, caffeine (2) and 1,3-dimethylpyrimidine-2,4(1H,3H)-dione (3). The structure of 1 was elucidated by the aid of 1D, 2D NMR and MS experiments. The structures of the known compounds were identified by comparison of their spectroscopic data with those reported in the literature.

Levothyroxine sodium revisited: A wholistic structural elucidation approach of new impurities via HPLC-HRMS/MS, on-line H/D exchange, NMR spectroscopy and chemical synthesis.

PubMed

Ruggenthaler, M; Grass, J; Schuh, W; Huber, C G; Reischl, R J

2017-02-20

The structural elucidation of unknown pharmaceutical impurities plays an important role in the quality control of newly developed and well-established active pharmaceutical ingredients (APIs). The United States Pharmacopeia (USP) monograph for the API Levothyroxine Sodium, a synthetic thyroid hormone, features two high pressure liquid chromatography (HPLC) methods using UV-VIS absorption detection to determine organic impurities in the drug substance. The impurity profile of the first USP method ("Procedure 1") has already been extensively studied, however for the second method ("Procedure 2"), which exhibits a significantly different impurity profile, no wholistic structural elucidation of impurities has been performed yet. Applying minor modifications to the chromatographic parameters of USP "Procedure 2" and using various comprehensive structural elucidation methods such as high resolution tandem mass spectrometry with on-line hydrogen-deuterium (H/D) exchange or two-dimensional nuclear magnetic resonance spectroscopy (NMR) we gained new insights about the complex impurity profile of the synthetic thyroid hormone. This resulted in the characterization of 24 compounds previously unknown to literature and the introduction of two new classes of Levothyroxine Sodium impurities. Five novel compounds were unambiguously identified via isolation or synthesis of reference substances and subsequent NMR spectroscopic investigation. Additionally, Collision-Induced Dissociation (CID)-type fragmentation of identified major impurities as well as neutral loss fragmentation patterns of many characterized impurities were discussed. Copyright © 2016 Elsevier B.V. All rights reserved.

Isolation, pharmacological activity and structure determination of physalin B and 5β,6β-epoxyphysalin B isolated from Congolese Physalis angulata L.

PubMed

Mangwala Kimpende, Peter; Lusakibanza, Mariano; Mesia, Kahunu; Tona, Lutete; Tits, Monique; Angenot, Luc; Frédérich, Michel; Van Meervelt, Luc

2013-12-15

Physalis angulata L., an annual herb from the Solanaceae family, is widely used in popular medicine in tropical countries to treat a variety of diseases. Two products, (X) and (Y), were isolated from a crude CH2Cl2 extract of dried Congolese Physalis angulata L. plants and crystallized from acetone for structure elucidation. Compound (X) corresponds to a physalin B dimer acetone solvate hydrate (2C28H30O9·C3H6O·0.22H2O), while compound (Y) crystallizes as a mixed crystal containing two physalin B molecules which overlap with 5β,6β-epoxyphysalin B, also known as physalin F, and one acetone molecule in the asymmetric unit (1.332C28H30O9·0.668C28H30O10·C3H6O). Antiplasmodial activity, cytotoxic activity and selectivity indices were determined for crude extracts and the two isolated products (X) and (Y).

[Studies on chemical constituents of the seeds of Allium cepa].

PubMed

Yuan, Ling; Ji, Teng-Fei; Wang, Ai-Guo; Yang, Jian-Bo; Su, Ya-Lun

2008-02-01

To study the chemical constituents from the seeds of Allium cepa L., the constituents of the seeds of Allium cepa L. To isolate and purify by silica gel, macroporous resin HP-20, Sephadex LH-20, RP-18 column. Seven compounds were isolated from the EtOH extract of the seeds of Allium cepa., their structures were elucidated by physico-chemical properties and spectroscopic analysis as tianshic acid (I), N-trans-feruloyl tyramine (II), beta-sitosterol-3 beta-glucopyranoside-6'-palmitate (III), sitosterol (IV), daucosterol (V), tryptophane (VI), adenine riboside (VI). Compounds V-VIII are obtained from this plant for the first time, compounds I-IV are isolated from the genus Allium for the first time.

[Study on chemical constituents from roots of Saussurea lappa].

PubMed

Zhang, Ting; Wang, Hongqing; Du, Guanhua; Chen, Ruoyun

2009-05-01

To study the chemical constituents in roots of Saussurea lappa. Isolation and purification were carried out by silica gel, Sephadex LH-20 and RP-18 column chromatography. The chemical structures of constituents were elucidated on the basis of spectral data. Eleven compounds were isolated and identified as: 5,7-dihydroxy-2-methylchromone (1), p-hydroxybenzaldehyde (2), 3,5-dimethoxy-4-hydroxy-benzaldehyde (3), 3,5-dimethoxy-4-hydroxy-acetophenone (4), ethyl 2-pyrrolidinone-5(s)-carboxylate (5), 5-hydroxymethyl-furaldehyde (6), palmitic acid (7), succinic acid (8), glucose (9), daucosterol (10), beta-sitosterol (11). Compounds 1, 2, 4, 5, 7, 9 were isolated from the genus Saussurea for the first time.

[Studies on the chemical constituents of Pharbitis purpurea].

PubMed

Wang, Jin-Lan; Hua, Zhun; Zhao, Bao-Ying; Tang, Wan-Xia; Zhang, Shu-Jun

2010-10-01

To study the chemical constituents of Pharbitis purpurea. The constituents were isolated by silica gel column chromatography, HPLC and recrystallization and their structures were elucidated on the basis of spectral analysis. Fourteen compounds were isolated and identified as daucosterol (1), umbelliferone (2), ursolic acid (3), N-p-hydroxy-cis-coumaroyltyramine (4), N-p-hydroxy-trans-coumaroyltyramine (5), N-cis-feruloyltyramine (6), N-trans-feruloyltyramine (7), (3R, 5R, 6S, 7E, 9S)-megastigman-5,6-epoxy-7-ene-3,9-diol (8), (6S,9R)-vomifoliol (9), (+)-syringaresinol (10), isovitexin (11), syringopicroside( 12), uricil (13), (6S,9R)-roseoside (14). Compounds 3, 8-2,14 are isolated from the genus for the first time.

Cytotoxic and Antibacterial Beilschmiedic Acids from a Gabonese Species of Beilschmiedia

PubMed Central

Williams, Russell B.; Martin, Steven M.; Hu, Jin-Feng; Norman, Vanessa L.; Goering, Matt G.; Loss, Sandra; O’Neil-Johnson, Mark; Eldridge, Gary R.; Starks, Courtney M.

2012-01-01

High-throughput natural products chemistry methods have facilitated the isolation of eight new (1–8) and two known (9 and 10) beilschmiedic acid derivatives from the leaves of a Gabonese species of Beilschmiedia. Compounds 3–10 were isolated in microgram quantities, and the NMR data for structure elucidation and dereplication were acquired utilizing a Bruker BioSpin TCI 1.7 mm MicroCryoProbe. All of the compounds were screened for cytotoxic and antibacterial activity against NCI-H460 human lung cancer cells and a clinical isolate of methicillin-resistant Staphylococcus aureus, respectively. This is the first report of cytotoxic activity for the endiandric/beilschmiedic acid class of compounds. PMID:22758788

Monosubstituted Benzene Derivatives from Fruits of Ficus hirta and Their Antifungal Activity against Phytopathogen Penicillium italicum.

PubMed

Wan, Chunpeng; Han, Jianxin; Chen, Chuying; Yao, Liangliang; Chen, Jinyin; Yuan, Tao

2016-07-20

Ficus hirta, a widely consumed food by Hakka people, has been reported to show potent antifungal activity against phytopathogen Penicillium italicum. However, there is no report of chemical constituents responsible for the antifungal activity. In the current study, nine monosubstituted benzene derivatives, including three new derivatives (1-3), were isolated from the fruits of F. hirta. The structures of these isolates were elucidated on the basis of the analysis of spectroscopic data (mass spectrometry and nuclear magnetic resonance). All of the isolates were evaluated for antifungal activities against P. italicum. At an equivalent concentration, compound 1 exhibited stronger antifungal activity than that of the ethanol extract of F. hirta fruits.

New protopine and benzyltetrahydroprotoberberine alkaloids from Aristolochia constricta and their activity on isolated guinea-pig ileum.

PubMed

Rastrelli, L; Capasso, A; Pizza, C; De Tommasi, N; Sorrentino, L

1997-11-01

Five new protopine-type alkaloids, 3,5-di-O-methylconstrictosine (1), 5,6-dihydro-3,5-di-O-methylconstrictosine (2), 5,6-dihydroconstrictosine (3), constrictosine (4), 3-O-methylconstrictosine (5), and a novel 8-benzylberberine-type alkaloid, (-)-8 beta-(4'-hydroxybenzyl)-2,3-dimethoxyberbin-10-ol (6) were isolated from the aerial parts of Aristolochia constricta. Their structures were elucidated by physical and spectroscopic data. The results of our pharmacological experiments indicated that MeOH extract, its partially purified fraction VI and the protopine derivatives constrictosine 1-5, significantly reduced, in a dose dependent manner, the electrical, acetylcholine, and histamine contractions of the isolated guinea-pig ileum.

Two pairs of farnesyl phenolic enantiomers as natural nitric oxide inhibitors from Ganoderma sinense.

PubMed

Wang, Meng; Wang, Fei; Xu, Feng; Ding, Li-Qin; Zhang, Qian; Li, Hui-Xiang; Zhao, Feng; Wang, Li-Qing; Zhu, Li-Han; Chen, Li-Xia; Qiu, Feng

2016-07-15

Four new farnesyl phenolic compounds, ganosinensols A-D (1-4) were isolated from the 95% EtOH extract of the fruiting bodies of Ganoderma sinense. Two pairs of enantiomers, 1/2, and 3/4 were isolated by HPLC using a Daicel Chiralpak IE column. Their structures were elucidated from extensive spectroscopic analyses and comparison with literature data. The absolute configurations of 1-4 were assigned by ECD spectra. All of these isolated compounds showed potent inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages, with IC50 values from 1.15 to 2.26μM. Copyright © 2016 Elsevier Ltd. All rights reserved.

Briareolate Esters from the Gorgonian Briareum asbestinum

PubMed Central

Meginley, Rian J.; Gupta, Prasoon; Schulz, Thomas C.; McLean, Amanda B.; Robins, Allan J.; West, Lyndon M.

2012-01-01

Two new briarane diterpenoids briareolate esters J (1) and K (2) were isolated from the methanolic extract of the octocoral Briareum asbestinum collected off the coast of Boca Raton, Florida. The structures of briaranes 1 and 2 were elucidated by interpretation of spectroscopic data. Briareolate ester K (2) showed weak growth inhibition activity against human embryonic stem cells (BG02). PMID:23015768

Anti-tumor abietane diterpenes from the cones of Sequoia sempervirens.

PubMed

Son, Kwang-Hee; Oh, Hyun-Mi; Choi, Sung-Kyu; Han, Dong Cho; Kwon, Byoung-Mog

2005-04-15

A new abietane, namely, 20-hydroxyferruginol (1), together with known ferruginol (2), 18-hydroxyferruginol (3), sugiol (4), and 6alpha-hydroxysugiol (5), were isolated from the cones of Sequoia sempervirens. Their structures were elucidated through spectral data. Compounds 1 and 5 strongly inhibited colon, lung, and breast human tumors and oncogene transformed cells with GI(50) 2-5 microg/mL.

Exopisiod B and farylhydrazone C, two new alkaloids from the Antarctic-derived fungus Penicillium sp. HDN14-431.

PubMed

Zhang, Ting; Zhu, Mei-Lin; Sun, Guang-Yu; Li, Na; Gu, Qian-Qun; Li, De-Hai; Che, Qian; Zhu, Tian-Jiao

2016-10-01

Two new compounds, exopisiod B (1) and farylhydrazone C (2), together with two known compounds (3-4), were isolated from the Antarctic-derived fungus Penicillium sp. HDN14-431. Their structures including absolute configurations were elucidated by spectroscopic methods and TDDFT ECD calculations. The cytotoxicity and antimicrobial activities of all compounds were tested.

Citrinamides, new potentiators of antifungal miconazole activity, produced by Penicillium sp. FKI-1938.

PubMed

Fukuda, Takashi; Hasegawa, Yoko; Sakabe, Yasunari; Tomoda, Hiroshi; Omura, Satoshi

2008-09-01

Two new aromatic alkaloids, designated citrinamides A and B, were isolated from the culture broth of Penicillium sp. FKI-1938 by solvent extraction, silica gel column chromatography and HPLC. Their structures were elucidated by spectroscopic analysis, including NMR and amino acid analysis. Citrinamides A and B showed moderate potentiation of miconazole activity against Candida albicans.

Antascomicins A, B, C, D and E. Novel FKBP12 binding compounds from a Micromonospora strain.

PubMed

Fehr, T; Sanglier, J J; Schuler, W; Gschwind, L; Ponelle, M; Schilling, W; Wioland, C

1996-03-01

5 novel ascomycin-like compounds, antascomicins A, B, C, D and E were isolated from a strain of Micromonospora. The antascomicins bind strongly to the FK506-binding protein FKBP12 and antagonize the immunosuppressive activity of FK506 and rapamycin. The strain description, fermentation, structure elucidation and biological activity of these compounds are described.

Oligomeric hydrolyzable tannins from Monochaetum multiflorum.

PubMed

Isaza, José H; Ito, Hideyuki; Yoshida, Takashi

2004-02-01

Four hydrolyzable tannins, nobotanins Q, R, S, and T, were isolated from the aqueous acetone extract of the dried leaves of Monochaetum multiflorum (Melastomataceae), a plant indigenous to Colombia. Their dimeric and tetrameric structures were elucidated by spectral and chemical methods. Eight known hydrolyzable tannin monomers and eight ellagitannin oligomers characteristic of melastomataceous plants were also characterized as tannin constituents of the plant.

Studies on the chemical constituents of the fruits of Cordia latifolia.

PubMed

Siddiqui, Bina S; Perwaiz, Sobiya; Begum, Sabira

2006-02-01

Four new aromatic compounds have been isolated from the fruits of Cordia latifolia (Boreginaceae) bearing a common basic skeleton but differing in the side chain. Their structures were elucidated using spectrometric methods including 1D- (1H and 13C) and 2D-NMR experiments, (1H, 1H-COSY, NOESY, HMQC and HMBC) and chemical transformations.

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.

Constituents of Clerodendrum bungei.

PubMed

Yang, Hui; Hou, Ai-Jun; Mei, Shuang-Xi; Sun, Han-Dong; Che, Chun-Tao

2002-09-01

Two new compounds, 5-O-ethylcleroindicin D (1) and bungein A (2), together with 12 known compounds (3-14), were isolated from the aerial parts of the medicinal plant Clerodendrum bungei. The structures of 1 and 2 were elucidated as a perhydrobenzofuran derivative and a peroxide dimer by spectral and chemical evidence. Compounds 3-14 have been obtained from this species for the first time.

Characterization of [8-ethyl]-chlorophyll c3 from Emiliania huxleyi.

PubMed

Álvarez, Susana; Zapata, Manuel; Garrido, José L; Vaz, Belén

2012-06-04

We report herein the isolation and complete characterization of a member of the chlorophyll c family, designated as [8-ethyl]-chlorophyll c(3) ([8-ethyl]-chl c(3)). Structural elucidation of this pigment rested on the analysis of mono- and bidimensional NMR, UV-VIS spectroscopy and ESI-MS data, and the configuration at the 13(2) position on chiral HPLC analysis.

Isolation of pyrrolocins A-C: cis- and trans-decalin tetramic acid antibiotics from an endophytic fungal-derived pathway.

PubMed

Jadulco, Raquel C; Koch, Michael; Kakule, Thomas B; Schmidt, Eric W; Orendt, Anita; He, Haiyin; Janso, Jeffrey E; Carter, Guy T; Larson, Erica C; Pond, Christopher; Matainaho, Teatulohi K; Barrows, Louis R

2014-11-26

Three new decalin-type tetramic acid analogues, pyrrolocins A (1), B (2), and C (3), were defined as products of a metabolic pathway from a fern endophyte, NRRL 50135, from Papua New Guinea. NRRL 50135 initially produced 1 but ceased its production before chemical or biological evaluation could be completed. Upon transfer of the biosynthetic pathway to a model host, 1-3 were produced. All three compounds are structurally related to equisetin-type compounds, with 1 and 3 having a trans-decalin ring system, while 2 has a cis-fused decalin. All were active against Mycobacterium tuberculosis, with the trans-decalin analogues 1 and 3 exhibiting lower MICs than the cis-decalin analogue 2. Here we report the isolation, structure elucidation, and antimycobacterial activities of 1-3 from the recombinant expression as well as the isolation of 1 from the wild-type fungus NRRL 50135.

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.

UPLC-QTOF-MS/MS-guided isolation and purification of sulfur-containing derivatives from sulfur-fumigated edible herbs, a case study on ginseng.

PubMed

Zhang, Li; Shen, Hong; Xu, Jun; Xu, Jin-Di; Li, Zhen-Ling; Wu, Jie; Zou, Ye-Ting; Liu, Li-Fang; Li, Song-Lin

2018-04-25

In this study, a novel ultra-performance liquid chromatography coupled with quadrupole/time-of-flight mass spectrometry (UPLC-QTOF-MS/MS)-guidance strategy was proposed for preparation of sulfur-containing derivatives in sulfur-fumigated edible herbs. Being versatile in both chromatographic separation and mass spectrometric detection, UPLC-QTOF-MS/MS was inducted into each experimental step for multifaceted purposes including finding, tracking, purity determination and structural elucidation of targeted compounds as well as UPLC-HPLC chromatographic conditions transplantation, whereby the isolation and purification procedures were greatly facilitated. Using this strategy, a new sulfur-containing ginsenoside Rg 1 derivative (named compound I) was obtained from sulfur-fumigated ginseng. The chemical structure of compound I was elucidated to be (3β, 6α, 12β)-3, 12-dihydroxydammar-25-ene-6, 20-diylbis-β-d-glucopyranoside, 24-sulfonic acid by QTOF-MS/MS, 1 H-NMR and 13 C-NMR analysis, and its generation mechanisms by sulfur-fumigation were accordingly discussed. The research deliverable suggests that the UPLC-QTOF-MS/MS-guidance strategy is promising for targeted preparation of sulfur-containing derivatives from sulfur-fumigated edible herbs. Copyright © 2017 Elsevier Ltd. All rights reserved.

Structural Characterization and Evaluation of the Antioxidant Activity of Phenolic Compounds from Astragalus taipaishanensis and Their Structure-Activity Relationship

NASA Astrophysics Data System (ADS)

Pu, Wenjun; Wang, Dongmei; Zhou, Dan

2015-09-01

Eight phenolic compounds were isolated using bio-guided isolation and purified from the roots of Astragalus taipaishanensis Y. C. Ho et S. B. Ho (A. taipaishanensis) for the first time. Their structures were elucidated by ESI-MS, HR-ESI-MS, 1D-NMR and 2D-NMR as 7,2‧-dihydroxy-3‧,4‧-dimethoxy isoflavan (1), formononetin (2), isoliquiritigenin (3), quercetin (4), kaempferol (5), ononin (6), p-hydroxybenzoic acid (7) and vanillic acid (8). Six flavonoids (compounds 1-6) exhibited stronger antioxidant activities (determined by DPPH, ABTS, FRAP and lipid peroxidation inhibition assays) than those of BHA and TBHQ and also demonstrated noticeable protective effects (particularly quercetin and kaempferol) on Escherichia coli under oxidative stress. Additionally, the chemical constituents compared with those of Astragalus membranaceus and the structure-activity relationship of the isolated compounds were both analyzed. The results clearly demonstrated that A. taipaishanensis has the potential to be selected as an alternative medicinal and food plant that can be utilized in health food products, functional tea and pharmaceutical products.

Two structurally distinct chalcone dimers from Helichrysum zivojinii and their activities in cancer cell lines.

PubMed

Aljančić, Ivana S; Vučković, Ivan; Jadranin, Milka; Pešić, Milica; Dorđević, Iris; Podolski-Renić, Ana; Stojković, Sonja; Menković, Nebojša; Vajs, Vlatka E; Milosavljević, Slobodan M

2014-02-01

Dimers tomoroside A (1) and tomoroside B (2) of the co-occuring known chalcone monomer (3), along with the seven known flavonoid glucosides (4-10), were isolated from the aerial parts of Helichrysum zivojinii Černjavski & Soška. The structures of the isolated compounds were elucidated by spectroscopic techniques. Compound 1 inhibited topo IIα and hif-1α expression and stimulated doxorubicin anticancer effect, while 2 increased the expression of hif-1α, probably acting as antioxidant and redox status modulator. Notably, 2 synergized with Tipifarnib showing potential to improve the action of this new chemotherapeutic involved in the modulation of mitogene activated protein (MAP) kinase signaling pathway. Copyright © 2013 Elsevier Ltd. All rights reserved.

Synthesis and biological evaluation of Raddeanin A, a triterpene saponin isolated from Anemone raddeana.

PubMed

Qian, Shan; Chen, Quan Long; Guan, Jin Long; Wu, Yong; Wang, Zhou Yu

2014-01-01

First, Raddeanin A, a cytotoxic oleanane-type triterpenoid saponin isolated from Anemone raddeana REGEL, was synthesized. Stepwise glycosylation was adopted in the synthesis from oleanolic acid, employing arabinosyl, glucosyl and rhamnosyl trichloroacetimidate as donors. The chemical structure of Raddeanin A was confirmed by means of (1)H-NMR, (13)C-NMR, IR, MS and elemental analysis, which elucidated the structure to be 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside oleanolic acid. Biological activity tests showed that in the range of low concentrations, Raddeanin A displayed moderate inhibitory activity against histone deacetylases (HDACs), indicating that the HDACs' inhibitory activity of Raddeanin A may contribute to its cytotoxicity.

Actinoranone, A Cytotoxic Meroterpenoid of Unprecedented Structure from a Marine Adapted Streptomyces sp

PubMed Central

Nam, Sang-Jip; Kauffman, Christopher A.; Paul, Lauren A.; Jensen, Paul R.

2014-01-01

The isolation and structure elucidation of a new meroterpenoid, actinoranone (1), produced by a marine bacterium closely related to the genus Streptomyces is reported. Actinoranone is composed of an unprecedented dihydronaphthalenone polyketide linked to a bicyclic diterpenoid. The stereochemistry of 1 was defined by application of the advanced Mosher's method and by interpretation of spectroscopic data. Actinoranone (1) is significantly cytotoxic to HCT-116 human colon cancer cells with an LD50 = 2.0 μg/mL. PMID:24152065

A circular dichroism and structural study of the inclusion complex artemisinin-β-cyclodextrin

NASA Astrophysics Data System (ADS)

Marconi, Giancarlo; Monti, Sandra; Manoli, Francesco; Degli Esposti, Alessandra; Mayer, Bernd

2004-01-01

The inclusion complex between the powerful antimalarial agent Artemisinin and β-cyclodextrin has been studied by means of Circular Dichroism and elucidated by Density Functional Theory calculations on the isolated molecule combined to a statistical Monte Carlo search of the most stable geometry of the complex. The results evidence a host-guest structure in full agreement with the almost unaffected functionality of the drug, which is found to experience a significant hydrophilic environment when complexed.

A new rearranged dolabellane diterpene from the soft coral Clavularia inflata.

PubMed

Alea, Glenn V; Bowden, Bruce F; Ragasa, Consolacion Y

2008-06-15

A new dolabellane type diterpene 1 has been isolated through its acetate 1a. The structure of 1a was elucidated by extensive 1D and 2D NMR spectroscopy and confirmed by mass spectrometry. The structure of 1 was deduced by comparison of its NMR spectral data with those of 1a, while its relative stereochemistry was deduced by NOESY. The absolute stereochemistry of C-7 was determined by analyses of 1 separately esterified with R and S O-mandelic acids.

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

[Two novel isocoumarins from Erigeron breviscapus].

PubMed

Li, Jing; Yu, De-Quan

2013-07-01

Two novel isocoumarins, erigeronone C (1) and D (2), were isolated from the ethanol extract of the whole plant of Erigeron breviscapus (Vant.) Hand.-Mazz (Compositae). Their structures were respectively elucidated as 8, 9-dihydroxypyrano [3, 2-c] isochromen-4, 6-dione (1) and 4, 7-dihydroxy-3-(3-hydroxy-4-oxo-4H-pyran-2-yl)-1H-isochromen-1-one (2) on the basis of spectral analyses. Both structures of 1 and 2 possess a gamma-pyrone moiety and that is rare in natural products.

Online structural elucidation of alkaloids and other constituents in crude extracts and cultured cells of Nandina domestica by combination of LC-MS/MS, LC-NMR, and LC-CD analyses.

PubMed

Iwasa, Kinuko; Takahashi, Teturo; Nishiyama, Yumi; Moriyasu, Masataka; Sugiura, Makiko; Takeuchi, Atsuko; Tode, Chisato; Tokuda, Harukuni; Takeda, Kazuyoshi

2008-08-01

The combination of NMR, MS, and CD data permitted the structural elucidation including the absolute configuration of the known alkaloids and unknown components in the extract matrix solution of Nandina domestica without isolation and sample purification prior to the coupling experiments. Unstable natural stereoisomers were identified by LC-NMR and LC-MS. Five known alkaloids, (S)-isoboldine, (S)-domesticine, (S)-nantenine, sinoacutine, and menispermine, were identified from N. domestica. O-Methylpallidine and (E, E)-, (E, Z)-, and (Z, Z)-terrestribisamide were also characterized for the first time from this plant. Known jatrorrhizine, palmatine, and berberine and unknown (R)-carnegine and (E, E)-, (E, Z)-, and (Z, Z)-terrestribisamide were identified in the callus of N. domestica.

The Deep-Sea Polyextremophile Halobacteroides lacunaris TB21 Rough-Type LPS: Structure and Inhibitory Activity towards Toxic LPS

PubMed Central

Di Lorenzo, Flaviana; Palmigiano, Angelo; Paciello, Ida; Pallach, Mateusz; Garozzo, Domenico; Bernardini, Maria-Lina; La Cono, Violetta; Yakimov, Michail M.; Molinaro, Antonio; Silipo, Alba

2017-01-01

The structural characterization of the lipopolysaccharide (LPS) from extremophiles has important implications in several biomedical and therapeutic applications. The polyextremophile Gram-negative bacterium Halobacteroides lacunaris TB21, isolated from one of the most extreme habitats on our planet, the deep-sea hypersaline anoxic basin Thetis, represents a fascinating microorganism to investigate in terms of its LPS component. Here we report the elucidation of the full structure of the R-type LPS isolated from H. lacunaris TB21 that was attained through a multi-technique approach comprising chemical analyses, NMR spectroscopy, and Matrix-Assisted Laser Desorption Ionization (MALDI) mass spectrometry. Furthermore, cellular immunology studies were executed on the pure R-LPS revealing a very interesting effect on human innate immunity as an inhibitor of the toxic Escherichia coli LPS. PMID:28653982

Sesterterpenes as tubulin tyrosine ligase inhibitors. First insight of structure-activity relationships and discovery of new lead.

PubMed

Dal Piaz, Fabrizio; Vassallo, Antonio; Lepore, Laura; Tosco, Alessandra; Bader, Ammar; De Tommasi, Nunziatina

2009-06-25

Twenty-four new sesterterpenes, compounds 1-24, were isolated from the aerial parts of Salvia dominica. Their structures were elucidated by 1D and 2D NMR experiments as well as ESIMS analysis and chemical methods. The evaluation of the biological activity of Salvia dominica sesterterpenes by means of a panel of chemical and biological approaches, including chemical proteomics, surface plasmon resonance (SPR) measurements, and biochemical assays were realized. Obtained results showed that 18 out of the 24 sesterterpene lactones isolated from Salvia dominica interact with tubulin-tyrosine ligase (TTL) an enzyme involved in the tyrosination cycle of the C-terminal of tubulin, and inhibit TTL activity in cancer cells. Besides, results of our studies provided an activity/structure relationship that can be used to design effective TTL inhibitors.

Structural Revisions of a Class of Natural Products: Scaffolds of Aglycon Analogues of Fusicoccins and Cotylenins Isolated from Fungi.

PubMed

Tang, Ying; Xue, Yongbo; Du, Guang; Wang, Jianping; Liu, Junjun; Sun, Bin; Li, Xiao-Nian; Yao, Guangmin; Luo, Zengwei; Zhang, Yonghui

2016-03-14

The reisolation and structural revision of brassicicene D is described, and inspired us to reassign the core skeletons of brassicicenes C-H, J and K, ranging from dicyclopenta[a,d]cyclooctane to tricyclo[9.2.1.0(3,7)]tetradecane using quantum-chemical predictions and experimental validation strategies. Three novel, highly modified fusicoccanes, brassicicenes L-N, were also isolated from the fungus Alternaria brassicicola, and their structures were unequivocally established by spectroscopic data, ECD calculations, and crystallography. The reassigned structures represent the first class of bridgehead double-bond-containing natural products with a bicyclo[6.2.1]undecane carbon skeleton. Furthermore, their stabilities were first predicted with olefin strain energy calculations. Collectively, these findings extend our view of the application of computational predictions and biosynthetic logic-based structure elucidation to address problems related to the structure and stability of natural products. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Islands within an island: Population genetic structure of the endemic Sardinian newt, Euproctus platycephalus.

PubMed

Ball, Sarah E; Bovero, Stefano; Sotgiu, Giuseppe; Tessa, Giulia; Angelini, Claudio; Bielby, Jon; Durrant, Christopher; Favelli, Marco; Gazzaniga, Enrico; Garner, Trenton W J

2017-02-01

The identification of historic and contemporary barriers to dispersal is central to the conservation of endangered amphibians, but may be hindered by their complex life history and elusive nature. The complementary information generated by mitochondrial (mtDNA) and microsatellite markers generates a valuable tool in elucidating population structure and the impact of habitat fragmentation. We applied this approach to the study of an endangered montane newt, Euproctus platycephalus . Endemic to the Mediterranean island of Sardinia, it is threatened by anthropogenic activity, disease, and climate change. We have demonstrated a clear hierarchy of structure across genetically divergent and spatially distinct subpopulations. Divergence between three main mountain regions dominated genetic partitioning with both markers. Mitochondrial phylogeography revealed a deep division dating to ca. 1 million years ago (Mya), isolating the northern region, and further differentiation between the central and southern regions ca. 0.5 Mya, suggesting an association with Pleistocene severe glacial oscillations. Our findings are consistent with a model of southward range expansion during glacial periods, with postglacial range retraction to montane habitat and subsequent genetic isolation. Microsatellite markers revealed further strong population structure, demonstrating significant divergence within the central region, and partial differentiation within the south. The northern population showed reduced genetic diversity. Discordance between mitochondrial and microsatellite markers at this scale indicated a further complexity of population structure, in keeping with male-biased dispersal and female philopatry. Our study underscores the need to elucidate cryptic population structure in the ecology and conservation strategies for endangered island-restricted amphibians, especially in the context of disease and climate change.

Isolation, structure elucidation and antibacterial activity of methyl-4,8-dimethylundecanate from the marine actinobacterium Streptomyces albogriseolus ECR64.

PubMed

Thirumurugan, Durairaj; Vijayakumar, Ramasamy; Vadivalagan, Chithravel; Karthika, Pushparaj; Alam Khan, Md Khurshid

2018-05-25

Around 120 actinobacterial colonies were isolated from various regions of marine East coast region of Tamil Nadu, India. Among them, 33 were morphologically distinct and they were preliminarily screened for their antibacterial activity against Pseudomonas fluorescens, Vibrio cholerae, V. parahaemolyticus, V. alginolyticus, and Aeromonas hydrophila by cross-streak plate technique. Among the isolated, the isolate ECR64 exhibited maximum zone of inhibition against fish pathogenic bacteria. The crude bioactive compounds were extracted from the isolate ECR64 using different organic solvents which exhibited maximum antibacterial activity. Separation and purification of the bioactive compounds were made by column chromatography which yielded 27 fractions and were re-chromatographed to obtain the active compound. Ultra violet (UV), Fourier transform infrared (FT-IR) and nuclear magnetic resonance (NMR) spectral studies were used to predict the structure of the active compound which was identified as methyl-4,8-dimethylundecanate. The potential isolate ECR64 was identified as Streptomyces albogriseolus by phylogenetic, phenotypic and genotypic (16S rRNA gene sequence) analyses. The identified compound methyl-4,8-dimethylundecanate can be used as potential and alternative drug in disease management of aquaculture. Copyright © 2018 Elsevier Ltd. All rights reserved.

[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.

[Studies on the chemical constituents of ethyl acetate extract from the roots of Actinidia chrysantha].

PubMed

Meng, Li-Li; Huang, Chu-Sheng; Liu, Hong-Xing; Chen, Xi-Hui

2009-10-01

To study the chemical constituents of ethyl acetate extract from the roots of Actinidia chrysantha. Chromatographic methods were used to isolate the compounds from ethyl acetate extract from the roots of Actinidia chrysantha and chemical and spectral methods were used to elucidate the structures of the isolated compounds. Five compounds were identified as stigmast-3, 6-dione (I), beta-sitosterol (II), ursolicacid (III), beta-daucosterol (IV), 2alpha, 3beta, 23-triol-12-en-28-ursolic acid (V). Those compounds are obtained from the plant for the first time.

[Studies on chemical components of Lobelia chinensis].

PubMed

Jiang, Yanyan; Shi, Renbing; Liu, Bin; Wang, Qiuying; Dai, Ying

2009-02-01

To study on the chemical constituents of Lobelia chinensis. The coloumn chromatographic techniques were applied to isolate constituents, and their structures were elucidated by means of spectral data analysis. Sixteen compounds were isolated and identified as daucosterol (1), diosmetin (2), apigenin (3), chrysoeriol (4), loteolin (5), hesperidin (6), loteolin-7-O-beta-D-glucoside (7), apigenin-7-O-beta-D-glucoside (8), linarin (9), diosmin(10), 5,7-dimethoxy-8- hydroxycoumarin (11), palmitinic acid (12), lacceroic acid (13), stearic acid (14), beta-sitosterol (15), daucosterol (16). All of these compouds were obtained from L. chinensis for the first time.

Epigenetic modifiers alter the secondary metabolite composition of a plant endophytic fungus, Pestalotiopsis crassiuscula obtained from the leaves of Fragaria chiloensis.

PubMed

Yang, Xiao-Long; Huang, Le; Ruan, Xiao-Li

2014-01-01

The addition of the DNA methyltransferase inhibitor 500 μM 5-azacytidine to the culture medium of a plant endophytic fungus, Pestalotiopsis crassiuscula, obtained from the leaves of Fragaria chiloensis, dramatically altered the profiles of its metabolites and resulted in the isolation of one new coumarin (1), along with six known compounds (2-7). HPLC profiles revealed that only compounds 3, 4, and 7 belonged to the new induced secondary metabolites. The structures of all isolated compounds were elucidated on the basis of extensive analysis of NMR spectra.

Antiproliferative compounds of Artabotrys madagascariensis from the Madagascar rainforest†

PubMed Central

Murphy, Brian T.; Cao, Shugeng; Brodie, Peggy J.; Miller, James S.; Ratovoson, Fidy; Birkinshaw, Chris; Rakotobe, Etienne; Rasamison, Vincent E.; Tendyke, Karen; Suh, Edward M.; Kingston, David G. I.

2009-01-01

Bioassay-guided fractionation of an ethanol extract of Artabotrys madagascariensis led to the isolation of the new compound artabotrol A (1), two butenolides (2 and 3), and the tetracyclic triterpene polycarpol (4). Structure elucidation was determined on the basis of one and two-dimensional NMR, and absolute configuration of compounds 2–4 was verified by analysis of CD and optical rotation spectra. Two of the isolates, melodorinol (2) and acetylmelodorinol (3), were found to display antiproliferative activity against five different tumor cell lines with IC50 values ranging from 2.4 to 12 µM. PMID:18855218

[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.

(-)-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.

Gibbilimbols A-D, cytotoxic and antibacterial alkenylphenols from Piper gibbilimbum.

PubMed

Orjala, J; Mian, P; Rali, T; Sticher, O

1998-07-01

Fractionation of the petroleum ether extract from the leaves of Piper gibbilimbum collected in Papua New Guinea afforded four new alkenylphenols, gibbilimbols A-D (1-4). The structures of the isolates were elucidated by spectroscopic methods, mainly 1D- and 2D-NMR spectroscopy. Gibbilimbols A-D were found to be toxic to brine shrimp with an LC50 of approximately 5 microg/mL. Gibbilimbols A-D were further found to be cytotoxic toward KB nasopharyngal carcinoma cells (ED50 7.8-2.1 microg/mL). All isolates also showed antibacterial activity toward Staphylococcus epidermidis and Bacillus cereus.

[A new secoiridoid from the flowers of Jasminum officinale L. var. grandiflorum].

PubMed

Zhao, Gui-Qin; Yin, Zhi-Feng; Dong, Jun-Xing

2008-05-01

To study the chemical constituents of the flowers of Jasminum officinale L. var. grandiflorum, the compounds were isolated and purified by HPLC, recrystallization and chromatography on silica gel and Sephadex LH-20 column. Their structures were elucidated on the basis of physicochemical properties and spectral analysis. Six secoiridoids were identified as jasgranoside (I), jaspolyoside (II), 8-epi-kingiside (III), 10-hydroxy-oleuropein (IV), 10-hydroxy-ligstroside (V), oleoside-7, 11-dimethyl ester (VI). Compound I is a new compound. Compounds II, III, IV, V and VI were isolated from Jasminum officinale L. var. grandiflorum for the first time.

[Iridoid glycosides from buds of Jasminum officinale L. var. grandiflorum].

PubMed

Zhao, Gui-qin; Yin, Zhi-feng; Liu, Yu-cui; Li, Hong-bo

2011-10-01

The study on the buds of Jasminum officinale L. var. grandiflorum was carried out to look for anti-HBV constituents. The isolation and purification were performed by HPLC and chromatography on silica gel, polyamide and Sephadex LH-20 column. The structures were elucidated on the basis of physicochemical properties and spectral analysis. Six iridoid glycosides were identified as jasgranoside B (1), 6-O-methy-catalpol (2), deacetyl asperulosidic acid (3), aucubin (4), 8-dehydroxy shanzhiside (5), and loganin (6). Jasgranoside B (1) is a new compound. Compounds 2-6 were isolated from Jasminum officinale L. var. grandiflorum for the first time.

Pellitorine, a potential anti-cancer lead compound against HL6 and MCT-7 cell lines and microbial transformation of piperine from Piper Nigrum.

PubMed

Ee, Gwendoline Cheng Lian; Lim, Chyi Meei; Rahmani, Mawardi; Shaari, Khozirah; Bong, Choon Fah Joseph

2010-04-05

Pellitorine (1), which was isolated from the roots of Piper nigrum, showed strong cytotoxic activities against HL60 and MCT-7 cell lines. Microbial transformation of piperine (2) gave a new compound 5-[3,4-(methylenedioxy)phenyl]-pent-2-ene piperidine (3). Two other alkaloids were also found from Piper nigrum. They are (E)-1-[3',4'-(methylenedioxy)cinnamoyl]piperidine (4) and 2,4-tetradecadienoic acid isobutyl amide (5). These compounds were isolated using chromatographic methods and their structures were elucidated using MS, IR and NMR techniques.

Alkaloids from roots of Stephania rotunda and their cholinesterase inhibitory activity.

PubMed

Hung, Tran Manh; Dang, Nguyen Hai; Kim, Jin Cheol; Jang, Han-Su; Ryoo, Sung-Woo; Lee, Jeong Hyung; Choi, Jae Sue; Bae, Kihwan; Min, Byung Sun

2010-10-01

In the course of screening plants used in folk medicine as memory enhancers, a 70% ethanolic extract of Stephania rotunda roots showed significant AChE inhibitory activity. Repeated column chromatography led to the isolation of a new protoberberine alkaloid, which we named stepharotudine (1), and seven known compounds (2-8). The chemical structures of the isolated compounds were elucidated based on extensive 1D and 2D NMR spectroscopic data. Compounds 1-8 were investigated in vitro for their anticholinesterase activity using a rat cortex AChE enzyme. © Georg Thieme Verlag KG Stuttgart · New York.

Cytotoxic Steroids from the Vietnamese Soft Coral Sinularia conferta.

PubMed

Ngoc, Ninh Thi; Huong, Pham Thi Mai; Thanh, Nguyen Van; Chi, Nguyen Thi Phuong; Dang, Nguyen Hai; Cuong, Nguyen Xuan; Nam, Nguyen Hoai; Thung, Do Cong; Kiem, Phan Van; Minh, Chau Van

2017-03-01

Twelve steroids, including five new compounds 1-5, were isolated and structurally elucidated from a methanol extract of the Vietnamese soft coral Sinularia conferta. Their cytotoxic effects against three human cancer cell lines, lung carcinoma (A-549), cervical adenocarcinoma (HeLa), and pancreatic epithelioid carcinoma (PANC-1), were evaluated using 3-(4,5-dimethylthiazolyl-2)-2,5-diphenyltetrazolium bromide (MTT) assays. Among isolated compounds, 10 exhibited potent cytotoxic effects on all three tested cell lines with IC 50 values of 3.64±0.18, 19.34±0.42, and 1.78±0.69 µM, respectively.

Indonesian propolis: chemical composition, biological activity and botanical origin.

PubMed

Trusheva, Boryana; Popova, Milena; Koendhori, Eko Budi; Tsvetkova, Iva; Naydenski, Christo; Bankova, Vassya

2011-03-01

From a biologically active extract of Indonesian propolis from East Java, 11 compounds were isolated and identified: four alk(en)ylresorcinols (obtained as an inseparable mixture) (1-4) were isolated for the first time from propolis, along with four prenylflavanones (6-9) and three cycloartane-type triterpenes (5, 10 and 11). The structures of the components were elucidated based on their spectral properties. All prenylflavanones demonstrated significant radical scavenging activity against diphenylpicrylhydrazyl radicals, and compound 6 showed significant antibacterial activity against Staphylococcus aureus. For the first time Macaranga tanarius L. and Mangifera indica L. are shown as plant sources of Indonesian propolis.

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.

Racemic alkaloids from the fungus Ganoderma cochlear.

PubMed

Wang, Xin-Long; Dou, Man; Luo, Qi; Cheng, Li-Zhi; Yan, Yong-Ming; Li, Rong-Tao; Cheng, Yong-Xian

2017-01-01

Seven pairs of new alkaloid enantiomers, ganocochlearines C-I (1, 3-8), and three pairs of known alkaloids were isolated from the fruiting bodies of Ganoderma cochlear. The chemical structures of new compounds were elucidated on the basis of 1D and 2D NMR data. The absolute configurations of compounds 1, 3-10 were assigned by ECD calculations. Biological activities of these isolates against renal fibrosis were accessed in rat normal or diseased renal interstitial fibroblast cells. Importantly, the plausible biosynthetic pathway for this class of alkaloids was originally proposed. Copyright © 2016 Elsevier B.V. All rights reserved.

Verticillosides A-M: Polyoxygenated pregnane glycosides from Asclepias verticillata L.

PubMed

Araya, Juan J; Binns, Franklin; Kindscher, Kelly; Timmermann, Barbara N

2012-06-01

As part of our ongoing effort to explore the chemical diversity of plants of the United States Midwest region, the isolation and identification of 13 pregnane glycosides named verticillosides A-M from Asclepias verticillata L. are reported. The structures of these compounds were elucidated by various spectroscopic techniques, including 1D and 2D NMR, IR, UV, and HRMS. The cytotoxicity of the isolates was evaluated against paired breast cell lines Hs578T (cancer) and Hs578Bst (normal), however, no significant growth inhibition was observed. Copyright © 2012 Elsevier Ltd. All rights reserved.

Structure and Chemical Synthesis of a Biologically Active Form of Renilla (Sea Pansy) Luciferin*

PubMed Central

Hori, Kazuo; Cormier, Milton J.

1973-01-01

The structure of a biologically active form of Renilla (sea pansy) luciferin has been elucidated; this structure, confirmed by total chemical synthesis, is 3,7-dihydro-2-methyl-6-(p-hydroxyphenyl)-8-benzylimidazo [1,2-a] pyrazin-3-one. In the natural compound the methyl group at the 2 position is replaced by an unknown, more complex group. For this reason the synthetic compound is 10% as active as the natural compound in producing light with Renilla luciferase. However, the spectral properties of the two compounds are identical. In addition the rates of the luminescent reaction with both compounds are similar, and the color of the light produced is identical in each case. A compound isolated from the calcium-triggered photoprotein aequorin has been identified by Shimomura and Johnson [(1972) Biochemistry 11, 1602] to be 2-amino-3-benzyl-5-(p-hydroxyphenyl)pyrazine. This compound forms an integral part of the structure of Renilla luciferin. This, and other evidence, suggests that the structure elucidated for Renilla luciferin is a more general one associated with the luciferins of most, if not all, bioluminescent coelenterates. PMID:16592045

H1-A, a compound isolated from Fusarium oxysporum inhibits hepatitis C virus (HCV) NS3 serine protease.

PubMed

Yang, Li-Yuan; Lin, Jun; Zhou, Bin; Liu, Yan-Gang; Zhu, Bao-Quan

2016-04-01

The present study was aimed to isolate the active compounds from the fermentation products of Fusarium oxysporum, which had hepatitis C virus (HCV) NS3 protease inhibitory activity. A bioactive compound was isolated by reverse-phase silica-gel column chromatography, silica-gel column chromatography, semi-preparative reverse-phase High Performance Liquid Chromatography (HPLC), and then its molecular structure was elucidated based on the spectrosopic analysis. As a result, the compound (H1-A, 1) Ergosta-5, 8 (14), 22-trien-7-one, 3-hydroxy-,(3β, 22E) was isolated and identified. To the best of our knowledge, this was the first report on the isolation of H1-A from microorganisms with the inhibitory activity of NS3 protease. Copyright © 2016 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.

Pestaloquinols A and B, isoprenylated epoxyquinols from Pestalotiopsis sp.

PubMed

Ding, Gang; Zhang, Fan; Chen, Hong; Guo, Liangdong; Zou, Zhongmei; Che, Yongsheng

2011-02-25

Two new isoprenylated epoxyquinol derivatives, pestaloquinols A (2) and B (3), and their putative biosynthetic precursor, cytosporin D (1), were isolated from the crude extract of the plant endophytic fungus Pestalotiopsis sp. The structures of these compounds were elucidated primarily by NMR experiments. Pestaloquinols A (2) and B (3) possess a previously undescribed nonacyclic ring system and showed cytotoxicity against HeLa cells.

Daryamide Analogues from a Marine-Derived Streptomyces species.

PubMed

Fu, Peng; La, Scott; MacMillan, John B

2017-04-28

Three new cyclohexene amine derivatives, daryamides D-F (1-3), a new arylamine derivative, carpatamide D (4), and a new ornithine lactamization derivative, ornilactam A (5), were isolated from the marine-derived Streptomyces strain SNE-011. Their structures, including absolute configurations, were elucidated on the basis of spectroscopic analysis and chemical methods. The carpatamide skeleton could be considered as the biosynthetic precursor of the daryamides.

Triterpenoid glycosides from Bacopa monnieri.

PubMed

Sivaramakrishna, Chillara; Rao, Chirravuri V; Trimurtulu, Golakoti; Vanisree, Mulabagal; Subbaraju, Gottumukkala V

2005-12-01

Two triterpenoid glycosides have been isolated along with 10 known saponins from Bacopa monnieri. Structures of the compounds have been elucidated as 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl] jujubogenin (1) and 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl] pseudojujubogenin (2) by high resolution NMR spectral data and chemical correlations. Further, the chemical compositions of bacosides A and B have been delineated.

Triterpenes and flavonol glucuronides from Oenothera cheiranthifolia.

PubMed

Nakanishi, Tsutomu; Inatomi, Yuka; Murata, Hiroko; Ishida, Syun-Suke; Fujino, Yuri; Miura, Kanako; Yasuno, Yoshito; Inada, Akira; Lang, Frank A; Murata, Jin

2007-02-01

A new ursane-type triterpene, named as cheiranthic acid (1), was isolated from the MeOH extract of whole plants of Oenothera cheiranthifolia (Onagraceae) along with an isomeric pair of known oleanane- and ursane-type triterpenes (arjunolic acid and asiatic acid) and three flavonol glucuronide analogues (quercetin 3-O-glucuronide, its n-butyl ester, and myricetin 3-O-glucuronide). Their structures were elucidated based on spectroscopic evidence.

New cytotoxic constituents from the Red Sea soft coral Nephthea sp.

PubMed

Hegazy, Mohamed-Elamir F; Gamal-Eldeen, Amira M; Mohamed, Tarik A; Alhammady, Montaser A; Hassanien, Abuzeid A; Shreadah, Mohamed A; Abdelgawad, Ibrahim I; Elkady, Eman M; Paré, Paul W

2016-06-01

Nephthea are soft coral species rich in sesquiterpenoids and steroids. An organic extract of Nephthea sp. resulted in the isolation of a new steroid (1), as well as several previously reported metabolites (2-9). Structures were elucidated by employing NMR and HR-EI-MS analyses. The total extract, fractions and purified compounds exhibited differential cytotoxicity against the breast cancer MCF-7 cell line.

Two new monoterpene glucosides from Xanthium strumarium subsp. sibiricum with their anti-inflammatory activity.

PubMed

Jiang, Hai; Xing, Xudong; Yan, Meiling; Guo, Xinyue; Yang, Lin; Yang, Liu

2018-06-01

Two new monoterpene glucosides: xanmonoter A (1) and xanmonoter B (2) were isolated from Xanthium strumarium. Their structures were elucidated on the basis of 1D and 2D NMR, MS and CD analysis. Compounds 1 and 2 were tested for their anti-inflammatory activity with IC 50 values of 17.4, 22.1 μM, respectively.

Cyclopentapeptides from Dianthus chinensis.

PubMed

Han, Jing; Huang, Maobo; Wang, Zhe; Zheng, Yuqing; Zeng, Guangzhi; He, Wenjun; Tan, Ninghua

2015-07-01

A new cyclopentapeptide dianthin I (1), together with two known ones pseudostellarin A (2) and heterophyllin J (3), was isolated from the aerial parts of Dianthus chinensis. The structure of 1 was elucidated as cyclo-(Gly(1)-L-Phe(2)-L-Pro(3)-L-Ser(4)-L-Phe(5)) on the basis of extensive spectroscopic analyses and chemical methods. Copyright © 2015 European Peptide Society and John Wiley & Sons, Ltd.

Tannins and related polyphenols of melastomataceous plants. VIII. Nobotanins L, M and N, trimeric hydrolyzable tannins from Tibouchina semidecandra.

PubMed

Yoshida, T; Nakata, F; Okuda, T

1999-06-01

Three hydrolyzable tannins, nobotannins L, M and N, were isolated from the water-soluble portion of the leaf extract of Tibouchina semidecandra, and their trimeric structures were elucidated from spectral and chemical evidence. Nobotanins L and N exist as equilibrium mixtures of four anomers due to the presence of two unacylated anomeric centers.

SYNTHESIS AND ISOLATION OF TETRAHYDROCANNABINOL ISOMERS.

DTIC Science & Technology

additional amount of cannabidiol . The structure of tetrahydrocannabinol B was elucidated by chemical and spectral evidence. The partial syntheses of...In addition to cannabinol, cannabidiol , and trans-1-hydroxy-3-n-amyl-6, 6, 9 trimethyl-6a, 7, 8, 10a-tetrahydro-6-dibenzopyran (tetrahydrocannabinol...only cannabidiolic acid. A second sample of Mexican marijuana furnished only tetrahydrocannabinol A and cannabinol, while a Spanish sample contained an

Spithioneines A and B, Two New Bohemamine Derivatives Possessing Ergothioneine Moiety from a Marine-Derived Streptomyces spinoverrucosus

PubMed Central

2015-01-01

Spithioneines A and B (1 and 2), two new bohemamine-type pyrrolizidine alkaloids possessing an unusual ergothioneine moiety, were isolated from a marine-derived Streptomyces spinoverrucosus. Their structures were elucidated by spectroscopic analysis, CD spectra, and chemical degradation and synthesis. Compounds 1 and 2 are rare natural products that incorporate the amino acid ergothioneine. PMID:26024315

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).

New antimycobacterial triterpenoids from Rhus taitensis.

PubMed

Jadulco, Raquel C; Koch, Michael; Van Wagoner, Ryan M; Pond, Christopher; Gideon, Osia G; Matainaho, Teatulohi; Piskaut, Pius; Barrows, Louis R

2011-09-01

Two new triterpenoids were isolated from the leaves and twigs of Rhus taitensis. Their structures were elucidated by 1D and 2D NMR spectroscopic studies as 1,10,24,25,30-pentahydroxysqualene and dammar-20(22),24-diene-3 β,26,27-triol. Both compounds exhibited moderate antimycobacterial activities with an MIC of 45 µg/mL. © Georg Thieme Verlag KG Stuttgart · New York.

Resin glycoside constituents of Ipomoea pes-caprae (beach morning glory).

PubMed

Tao, Hongwen; Hao, Xiaojiang; Liu, Jinggen; Ding, Jian; Fang, Yuchun; Gu, Qianqun; Zhu, Weiming

2008-12-01

Eight new resin glycosides, pescapreins X-XVII (1-8), were isolated from a lipophilic fraction of an ethanol extract of the entire plant of beach morning glory, Ipomoea pes-caprae. Their structures were elucidated by spectroscopic data analysis and by chemical transformation. These compounds were evaluated biologically in terms of cancer cell line cytotoxicity, antibacterial and antifungal activity, and effects on the mu-opioid receptor.

Penicyrones A and B, an epimeric pair of α-pyrone-type polyketides produced by the marine-derived Penicillium sp.

PubMed

Bu, Ying-Yue; Yamazaki, Hiroyuki; Takahashi, Ohgi; Kirikoshi, Ryota; Ukai, Kazuyo; Namikoshi, Michio

2016-01-01

Two polyketides containing an α-pyrone unit, named penicyrones A (1) and B (2), were isolated from a culture broth of the marine-derived Penicillium sp. TPU1271 together with nine known compounds: verrucosidin (3), fructigenine A (4), verrucofortine (5), cyclo-(L-Trp-L-Phe) (6), cyclopenol (7), cyclopenin (8), penipratynolene (9), aspterric acid (10) and viridicatol (11). The structures of 1 and 2 were elucidated by analyzing the spectroscopic data of 1, 2 and their O-acetyl derivatives (1a and 2a). Compounds 1 and 2 were epimers of each other at the C-9 position. The absolute configurations of 1 and 2 were assigned on the basis of NOESY data for 1, 2, 1a and 2a, a conformational analysis and the identity of the biogenetic pathway with verrucosidin (3). The planar structure of penicyrones was found in the SciFinder as a compound in the commercial chemical libraries; however, the stereostructure and spectroscopic data were not available. Therefore, this is the first study on the isolation and structure elucidation, including the absolute configurations, of penicyrones A (1) and B (2) as fungal metabolites. Compound 3 exhibited growth inhibitory activity against Mycobacterium smegmatis at 40 μg per disc (inhibition zone of 11 mm). This is the first study to demonstrate that verrucosidin (3) exhibited anti-mycobacterial activity.

Antiplasmodial, cytotoxic activities and characterization of a new naturally occurring quinone methide pentacyclic triterpenoid derivative isolated from Salacia leptoclada Tul. (Celastraceae) originated from Madagascar

PubMed Central

Ruphin, Fatiany Pierre; Baholy, Robijaona; Emmanue, Andrianarivo; Amelie, Raharisololalao; Martin, Marie-Therese; Koto-te-Nyiwa, Ngbolua

2013-01-01

Objective To validate scientifically the traditional use of Salacia leptoclada Tul. (Celastraceae) (S. leptoclada) and to isolate and elucidate the structure of the biologically active compound. Methods Bioassay-guided fractionation of the acetonic extract of the stem barks of S. leptoclada was carried out by a combination of chromatography technique and biological experiments in viro using Plasmodium falciparum and P388 leukemia cell lines as models. The structure of the biologically active pure compound was elucidated by 1D and 2D NMR spectroscopy and mass spectrometry. Results Biological screening of S. leptoclada extracts resulted in the isolation of a pentacyclic triterpenic quinone methide. The pure compound exhibited both in vitro a cytotoxic effect on murine P388 leukemia cells with IC50 value of (0.041±0.020) µg/mL and an antiplasmodial activity against the chloroquine-resistant strain FC29 of Plasmodium falciparum with an IC50 value of (0.052±0.030) µg/mL. Despite this interesting anti-malarial property of the lead compound, the therapeutic index was weak (0.788). In the best of our knowledge, the quinone methide pentacyclic triterpenoid derivative compound is reported for the first time in S. leptoclada. Conclusions The results suggest that furthers studies involving antineoplastic activity is needed for the development of this lead compound as anticancer drug. PMID:24075342

Antiplasmodial, cytotoxic activities and characterization of a new naturally occurring quinone methide pentacyclic triterpenoid derivative isolated from Salacia leptoclada Tul. (Celastraceae) originated from Madagascar.

PubMed

Ruphin, Fatiany Pierre; Baholy, Robijaona; Emmanue, Andrianarivo; Amelie, Raharisololalao; Martin, Marie-Therese; Koto-te-Nyiwa, Ngbolua

2013-10-01

To validate scientifically the traditional use of Salacia leptoclada Tul. (Celastraceae) (S. leptoclada) and to isolate and elucidate the structure of the biologically active compound. Bioassay-guided fractionation of the acetonic extract of the stem barks of S. leptoclada was carried out by a combination of chromatography technique and biological experiments in viro using Plasmodium falciparum and P388 leukemia cell lines as models. The structure of the biologically active pure compound was elucidated by 1D and 2D NMR spectroscopy and mass spectrometry. Biological screening of S. leptoclada extracts resulted in the isolation of a pentacyclic triterpenic quinone methide. The pure compound exhibited both in vitro a cytotoxic effect on murine P388 leukemia cells with IC50 value of (0.041±0.020) μg/mL and an antiplasmodial activity against the chloroquine-resistant strain FC29 of Plasmodium falciparum with an IC50 value of (0.052±0.030) μg/mL. Despite this interesting anti-malarial property of the lead compound, the therapeutic index was weak (0.788). In the best of our knowledge, the quinone methide pentacyclic triterpenoid derivative compound is reported for the first time in S. leptoclada. The results suggest that furthers studies involving antineoplastic activity is needed for the development of this lead compound as anticancer drug. Copyright © 2013 Asian Pacific Tropical Biomedical Magazine. Published by Elsevier B.V. All rights reserved.

Novel and unusual triterpene from Black Cohosh. Determination of structure of 9,10-seco-9,19-cyclolanostane xyloside (cimipodocarpaside) by NMR, IR and Raman spectroscopy and DFT calculations.

PubMed

Jamróz, Marta K; Jamróz, Michał H; Dobrowolski, Jan Cz; Gliński, Jan A; Davey, Matthew H; Wawer, Iwona

2011-01-01

A new triterpene xyloside, designated cimipodocarpaside was isolated from a Black Cohosh (Actea racemosa L.) extract and its structure was elucidated by means of 1H, 13C NMR, IR and Raman spectroscopy supported by B3LYP/6-31G** calculations. The vibrational spectra were interpreted using the PED analysis of 273 fundamentals. Its structure comprises four condensed rings A-D which are 6, 7, 6, and 5-membered, respectively. An oxiirane ring is located in the side chain and a xylose moiety is attached to the A-ring. Comparison of the experimental 13C NMR data with the theoretical chemical shifts of 24S- and 24R-cimipodocarpaside isomers revealed that the isolated compound has the 24S-configuration. Combined spectroscopic and computational studies enabled the determination of the structure of cimipodocarpaside as (24S)-3β-hydroxy-24,25-oxiirane-16,23-dione-9,10-seco-9,19-cyclolanost-7(8),9(11),10(19)-trien-3-O-β-D-xylopyranoside. Triterpenes with 7-membered ring were thus far isolated from only Actea podocarpa DC. plants. This is the first report on the isolation of such a compound from Black Cohosh. Copyright © 2010 Elsevier B.V. All rights reserved.

Novel and unusual triterpene from Black Cohosh. Determination of structure of 9,10- seco-9,19-cyclolanostane xyloside (cimipodocarpaside) by NMR, IR and Raman spectroscopy and DFT calculations

NASA Astrophysics Data System (ADS)

Jamróz, Marta K.; Jamróz, Michał H.; Dobrowolski, Jan Cz.; Gliński, Jan A.; Davey, Matthew H.; Wawer, Iwona

2011-01-01

A new triterpene xyloside, designated cimipodocarpaside was isolated from a Black Cohosh ( Actea racemosa L.) extract and its structure was elucidated by means of 1H, 13C NMR, IR and Raman spectroscopy supported by B3LYP/6-31G** calculations. The vibrational spectra were interpreted using the PED analysis of 273 fundamentals. Its structure comprises four condensed rings A-D which are 6, 7, 6, and 5-membered, respectively. An oxiirane ring is located in the side chain and a xylose moiety is attached to the A-ring. Comparison of the experimental 13C NMR data with the theoretical chemical shifts of 24 S- and 24 R-cimipodocarpaside isomers revealed that the isolated compound has the 24 S-configuration. Combined spectroscopic and computational studies enabled the determination of the structure of cimipodocarpaside as (24 S)-3β-hydroxy-24,25-oxiirane-16,23-dione-9,10- seco-9,19-cyclolanost-7(8),9(11),10(19)-trien-3-O-β- D-xylopyranoside. Triterpenes with 7-membered ring were thus far isolated from only Actea podocarpa DC. plants. This is the first report on the isolation of such a compound from Black Cohosh.

[Study on Chemical Constituents of Peanut Hull].

PubMed

Zuo, Ai-xue; Sun, Yun; Qian, Shao-xiang; Rao, Gao-xiong

2015-02-01

To investigate the chemical constituents of peanut hull. Several chromatography methods such as silica gel and Sephadex LH-20 combined with recrystallization were applied to isolate the compounds. Based on spectrum technologies (MS,1H-NMR and 13C-NMR) and physico-chemical methods, structures of isolated compounds were identified. Twelve compounds were isolated and elucidated as luteolin (1), diosmetin (2), 5,7,3',4'-tetrahydroxy-8-prenyflavone (3),5,7,3'-trihydroxy-4'- methoxy-8-prenylflavone(4), eriodicrtyol (5), racemoflavone (6), hydnocarpin (7), 5,7-dihydroxy chromone (8), 5-hydroxy-chromone- 7-O-β-D-glucoside (9), ferulic acid (10), β-sitosterol (11) and daucosterol(12). Except compounds 1, 5 and 8, all compounds are obtained from peanut hull for the first time.

Four new cytotoxic tetrahydrofuranoid lignans from Sinopodophyllum emodi.

PubMed

Sun, Yan-Jun; Li, Zhan-Lin; Chen, Hong; Liu, Xiao-Qiu; Zhou, Wei; Hua, Hui-Ming

2012-03-01

Four new tetrahydrofuranoid lignans, (-)-tanegool-7'-methyl ether ( 1), (+)-7'-methoxylariciresinol (2), sinolignan C (3), and epipinoresinol-4,4'-di- O- β- D-glucopyranoside (4), were isolated from the roots and rhizomes of SINOPODOPHYLLUM EMODI together with one known lignan (5). Their structures and stereochemistry were elucidated on the basis of spectroscopic and mass spectrometric evidence. The isolation of compounds 1- 5 represents the first report of tetrahydrofuran lignans from the genus SINOPODOPHYLLUM. The cytotoxic activities of all isolated compounds were evaluated against HeLa and KB cell lines, and compound 1 showed the most potent cytotoxicity with IC₅₀ values of 9.7 µM and 4.7 µM, respectively. © Georg Thieme Verlag KG Stuttgart · New York.

Glycosides of naphthohydroquinones and anthraquinones isolated from the aerial parts of Morinda parvifolia Bartl. ex DC (Rubiaceae) increase p53 mRNA expression in A2780 cells.

PubMed

Su, Xianming; Zhang, Jian; Li, Changkang; Li, Fenghua; Wang, Hongqing; Gu, Haifeng; Li, Baoming; Chen, Ruoyun; Kang, Jie

2018-05-11

Eight previously undescribed naphthohydroquinone glycosides, namely morindaparvins H-O, together with four known anthraquinone glycosides were isolated from the n-BuOH extract of the aerial parts of Morinda parvifolia Bartl. ex DC (Rubiaceae). The structures of morindaparvins H-O were elucidated on the basis of spectroscopic analysis. To our knowledge, this is the first isolation of quinone glycosides from the plant M. parvifolia. The results showed that all 12 compounds at the concentration of 50 μM significantly increased p53 mRNA expression in A2780 cells compared with the blank control group. Copyright © 2018 Elsevier Ltd. All rights reserved.

A new furofuran lignan from Piper terminaliflorum Tseng.

PubMed

Liu, Tie; Liang, Qian; Zhang, Xin-Min; Huang, Shen-Yang; Xu, Wen-Hui

2018-02-01

The chemical investigation of whole plants Piper terminaliflorum Tseng led to the isolation of one new furofuran lignan, 7-methoxyasarinin (1), along with three known amide alkaloids (2-4) as N-3,5-dimethoxy-4-hydroxycinnamoylpyrrole (2), dihydropipercide (3) and 1-[(2E,4E,9E)-10-(3,4-Methylenedioxyphenyl)-2,4,9-undecatrienoyl]pyrrolidine (4). Their structures were elucidated by extensive spectroscopic analyses, including 1D, 2D NMR and HR-ESI-MS, and by comparison with the literature. Compounds (2-4) were isolated from Piper terminaliflorum Tseng for the first time. All isolated compounds (1-4) were evaluated for their cytotoxic activities against five human cancer cell lines (including A-549, SMMC-7721, HL-60, MCF-7 and SW-480).

Chemical and bioactive diversities of the genus Chaetomium secondary metabolites.

PubMed

Zhang, Q; Li, H-Q; Zong, S-C; Gao, J-M; Zhang, A-L

2012-02-01

The genus Chaetomium fungi are considered to be a rich source of novel and bioactive secondary metabolites of great importance. Up till now, a variety of more than 200 secondary metabolites belonging to diverse structural types of chaetoglobosins, epipolythiodioxopiperazines, azaphilones, xanthones, anthraquinones, chromones, depsidones, terpenoids, and steroids have been discovered. Most of these fungal metabolites exhibited antitumor, cytotoxic, antimalarial, enzyme inhibitory, antibiotic, and other activities. This review covers the extraction, structure elucidation, structural diversity, and biological activities of natural products isolated from about 30 fungi associated with marine- and terrestrial- origins, and highlights some bioactive compounds as well as their mechanisms of action and structure-activity relationships.

Urease inhibitory isoflavonoids from different parts of Calopogonium mucunoides (Fabaceae).

PubMed

Ndemangou, Brigitte; Sielinou, Valerie Tedjon; Vardamides, Juliette Catherine; Ali, Muhammad Shaiq; Lateef, Mehreen; Iqbal, Lubna; Afza, Nigaht; Nkengfack, Augustin Ephrem

2013-12-01

The dichloromethane-methanol (1:1) soluble part of Calopogonium mucunoides (Fabaceae) resulted in the isolation of 10 isoflavones (4'-O-methylalpinumisoflavone, 4'-O-methylderrone, alpinumisoflavone, daidzeine, Calopogonium isoflavone A, atalantoflavone, 2',4',5',7-tetramethoxyisoflavone, 7-O-methylcuneantin, cabreuvin and 7-O-methylpseudobaptigenin) and a rotenoid (6a,12a-dehydroxydegueline). Among these, daidzeine, 7-O-methylcuneantin, atalantoflavone and 6a, 12a-dehydroxydegueline have been isolated for the first time from C. mucunoides while remaining are already reported from this source. Structures of all the isolated constituents were elucidated with the aid of NMR spectroscopic and mass spectrometric techniques. Among all the isolated constituents, nine were evaluated for their urease inhibitory potential. However, six were found potent. These include 4'-O-methylderrone, daidzeine, atalantoflavone, 2',4',5',7-tetramethoxyisoflavone, 7-O-methylcuneantin and 6a, 12a-dehydroxydegueline.

Anti-Helicobacter pylori metabolites from Rhizoctonia sp. Cy064, an endophytic fungus in Cynodon dactylon.

PubMed

Ma, Y M; Li, Y; Liu, J Y; Song, Y C; Tan, R X

2004-07-01

A new benzophenone, named rhizoctonic acid (1), together with three known compounds monomethylsulochrin (2), ergosterol (3) and 3beta,5alpha,6beta-trihydroxyergosta-7,22-diene (4) were isolated through bioassay-guided fractionations from the culture of Rhizoctonia sp. (Cy064), an endophytic fungus in the leaf of Cynodon dactylon. The structure of the new acid 1 was elucidated to be 5-hydroxy-2-(2-hydroxy-6-methoxy-4-methylbenzoyl)-3-methoxybenzoic acid by a combination of spectral analyses. Furthermore, the structure of monomethylsulochrin 2 was confirmed by 13C-NMR analysis. All four metabolites were subjected to a more detailed in vitro assessment of their antibacterial action against five clinically isolated and one reference (ATCC 43504) Helicobacter pylori strains.

Quassinoids from the stems of Picrasma quassioides and their cytotoxic and NO production-inhibitory activities.

PubMed

Xu, Jian; Xiao, Di; Song, Wei-Wu; Chen, Lei; Liu, Wen-Yuan; Xie, Ning; Feng, Feng; Qu, Wei

2016-04-01

Three new C20 quassinoids nigakilactone P (1), picraqualide F (2), nigakilactone Q (3), along with eight known quassinoids (4-11), were isolated from the 95% EtOH extract of the stems of Picrasma quassioides. The structures of the new compounds were elucidated by means of HRESIMS and different NMR techniques. Assignments of relative and absolute configurations for these compounds were achieved on the basis of ROESY spectra and quantum chemical ECD calculation. In vitro activity assays, none of the compounds showed cytotoxic (IC50>50 μM) and NO production-inhibitory activities (IC50>30 μM), and the structure-activity relationships of quassinoids were summarized. In addition, the chemotaxonomic significance of the isolated compounds was also discussed. Copyright © 2016 Elsevier B.V. All rights reserved.

Monoterpene derivatives with anti-allergic activity from red peony root, the root of Paeonia lactiflora.

PubMed

Shi, Yan-Hong; Zhu, Shu; Ge, Yue-Wei; He, Yu-Min; Kazuma, Kohei; Wang, Zhengtao; Yoshimatsu, Kayo; Komatsu, Katsuko

2016-01-01

The methanolic extract and its subfractions from red peony root, the dried roots of Paeonia lactiflora Pallas showed potent antiallergic effects, as inhibition of immunoglobulin E (IgE)-mediated degranulation in rat basophil leukemia (RBL)-2H3 cells. Bioassay-guided fractionation led to the isolation of 16 monoterpene derivatives, including 3 new compounds, paeoniflorol (1), 4'-hydroxypaeoniflorigenone (2) and 4-epi-albiflorin (3), together with 13 known ones (4-16). The chemical structures of the new compounds were elucidated on the basis of spectroscopic and chemical evidences. Among the isolated monoterpene derivatives, nine compounds showed potent anti-allergic effects and compound 1 was the most effective. A primary structure-activity relationship of monoterpene derivatives was discussed. Copyright © 2015 Elsevier B.V. All rights reserved.

Anti-inflammatory steroidal glycosides from the berries of Solanum nigrum L. (European black nightshade).

PubMed

Xiang, Limin; Wang, Yihai; Yi, Xiaomin; He, Xiangjiu

2018-04-01

Seven previously undescribed steroidal glycosides, along with three known congeners were isolated from the unripe berries of Solanum nigrum L. (Solanaceae). Their structures were elucidated on basis of 1D and 2D NMR, HR-ESI-MS spectroscopic data and GC analysis after acid hydrolysis. The potential inhibitory effects on nitric oxide (NO) production induced by lipopolysaccharide in RAW 264.7 cell line and the anti-proliferative activities against five cancer cell lines (HL-60, U-937, Jurkat, K562 and HepG2) were evaluated. Seven compounds exhibited inhibition activities on NO production with IC 50 values ranging from 11.33 to 49.35 μM. Structure-activity relationships of the isolated compounds were also discussed. Copyright © 2018 Elsevier Ltd. All rights reserved.

Isolation and identification of flavonoids, including flavone rotamers, from the herbal drug 'Crataegi folium cum flore' (hawthorn).

PubMed

Rayyan, S; Fossen, T; Solheim Nateland, H; Andersen, O M

2005-01-01

Twelve flavonoids, including seven flavones, four flavonols and one flavanone, were isolated from methanolic extract of the herbal drug 'Crataegi folium cum flore' (hawthorn leaves and flowers) by a combination of CC (over Amberlite XAD-7 and Sephadex LH-20) and preparative HPLC. Their structures, including that of the novel flavonol 8-methoxykaempferol 3-O-(6"-malonyl-beta-glucopyranoside), were elucidated by homo- and heteronuclear NMR and electrospray/MS. The 1H- and 13C-NMR of all compounds, including rotameric pairs of five flavone C-glycosides, were assigned. The presence and relative proportion of each rotamer was shown by various NMR experiments, including two-dimensional nuclear Overhauser and exchange spectroscopy, to depend on solvent, linkage position and structure of the C-glycosyl substituent.

Diarylheptanoids from Rhizomes of Alpinia officinarum Inhibit Aggregation of α-Synuclein.

PubMed

Fu, Guangmiao; Zhang, Wei; Du, Dongsheng; Ng, Yu Pong; Ip, Fanny C F; Tong, Rongbiao; Ip, Nancy Y

2017-08-09

Two new diarylheptanoids, alpinin A (1) and alpinin B (2), together with 18 known diarylheptanoids (3-20), were isolated from the rhizomes of Alpinia officinarum. Their structures were elucidated by comprehensive spectroscopic analysis, including high-resolution mass spectrometry, infrared spectroscopy, and one- and two-dimensional nuclear magnetic resonance spectroscopy. Structurally, alpinin A is a new member of the small family of oxa-bridged diarylheptanoids and contains the characteristic 2,6-cis-configured tetrahydropyran motif (C 1 -C 5 oxa bridge). The absolute configuration of alpinin A was confirmed by asymmetric total synthesis of the enantiomer (ent-1), corroborating the assignment of the molecular structure. The absolute configuration of alpinin B was determined on the basis of the analysis of the circular dichroism exciton chirality spectrum. We evaluated the inhibitory activity of all isolated diarylheptanoids against α-synuclein aggregation at 10 μM. Alpinins A and B significantly inhibited α-synuclein aggregation by 66 and 67%, respectively.

Structural elucidation of polysaccharide containing 3-O-methyl galactose from fruiting bodies of Pleurotus citrinopileatus.

PubMed

He, Pengfei; Zhang, Anqiang; Zhou, Saijing; Zhang, Fuming; Linhardt, Robert J; Sun, Peilong

2016-11-03

A water-soluble polysaccharide containing 3-O-methyl galactose (PCP60W) was isolated from fruiting bodies of Pleurotus citrinopileatus and purified by anion-exchange and gel column chromatography. This polysaccharide has an average molecular weight of 2.74 × 10 4  Da and its structure was elucidated using monosaccharide composition and methylation analysis combined with one- and two-dimensional (COSY, TOCSY, NOESY, HMQC and HMBC) NMR spectroscopy. PCP60W was shown to be a linear partially 3-O-methylated α-galactopyranan comprised of 6-linked galactose, 6-linked 3-O-methyl galactose and 4-linked glucose in a ratio of 3.0:1.0:0.6. This work provides additional evidence for the view that 3-O-methyl galactose is common to the genus Pleurotus. Copyright © 2016 Elsevier Ltd. All rights reserved.

Rapid screening and structural elucidation of a novel sibutramine analogue in a weight loss supplement: 11-desisobutyl-11-benzylsibutramine.

PubMed

Mans, Daniel J; Gucinski, Ashley C; Dunn, Jamie D; Gryniewicz-Ruzicka, Connie M; Mecker-Pogue, Laura C; Kao, Jeff L-F; Ge, Xia

2013-09-01

A novel analogue of sibutramine, 11-desisobutyl-11-benzylsibutramine, has been discovered. During routine ion mobility spectrometry (IMS) screening of a weight loss supplement collected at an US FDA import operation facility an unknown peak was observed. Further analysis of the supplement by liquid chromatography-mass spectrometry (LC-MS) and high resolution mass spectrometry revealed an unknown peak with a relative retention time of 1.04 with respect to sibutramine and a predicted formula of C20H24NCl. In order to elucidate the analogue's structure, it was isolated from the supplement and characterized by tandem mass spectrometry and nuclear magnetic resonance (NMR), which revealed the analogue possessed a benzyl moiety at the 11 position in place of the isobutyl group associated with sibutramine. Copyright © 2013. Published by Elsevier B.V.

Structure Elucidation and Immunomodulatory Activity of A Beta Glucan from the Fruiting Bodies of Ganoderma sinense

PubMed Central

Yue, Rui-Qi; Dong, Cai-Xia; Chan, Chung-Lap; Ko, Chun-Hay; Cheung, Wing-Shing; Luo, Ke-Wang; Dai, Hui; Wong, Chun-Kwok; Leung, Ping-Chung; Han, Quan-Bin

2014-01-01

A polysaccharide named GSP-2 with a molecular size of 32 kDa was isolated from the fruiting bodies of Ganoderma sinense. Its structure was well elucidated, by a combined utilization of chemical and spectroscopic techniques, to be a β-glucan with a backbone of (1→4)– and (1→6)–Glcp, bearing terminal- and (1→3)–Glcp side-chains at O-3 position of (1→6)–Glcp. Immunological assay exhibited that GSP-2 significantly induced the proliferation of BALB/c mice splenocytes with target on only B cells, and enhanced the production of several cytokines in human peripheral blood mononuclear cells and derived dendritic cells. Besides, the fluorescent labeled GSP-2 was phagocytosed by the RAW 264.7 cells and induced the nitric oxide secretion from the cells. PMID:25014571

Isolation by environmental distance in mobile marine species: molecular ecology of franciscana dolphins at their southern range.

PubMed

Mendez, Martin; Rosenbaum, Howard C; Subramaniam, Ajit; Yackulic, Charles; Bordino, Pablo

2010-06-01

The assessment of population structure is a valuable tool for studying the ecology of endangered species and drafting conservation strategies. As we enhance our understanding about the structuring of natural populations, it becomes important that we also understand the processes behind these patterns. However, there are few rigorous assessments of the influence of environmental factors on genetic patterns in mobile marine species. Given their dispersal capabilities and localized habitat preferences, coastal cetaceans are adequate study species for evaluating environmental effects on marine population structure. The franciscana dolphin, a rare coastal cetacean endemic to the Western South Atlantic, was studied to examine these issues. We analysed genetic data from the mitochondrial DNA and 12 microsatellite markers for 275 franciscana samples utilizing frequency-based, maximum-likelihood and Bayesian algorithms to assess population structure and migration patterns. This information was combined with 10 years of remote sensing environmental data (chlorophyll concentration, water turbidity and surface temperature). Our analyses show the occurrence of genetically isolated populations within Argentina, in areas that are environmentally distinct. Combined evidence of genetic and environmental structure suggests that isolation by distance and a process here termed isolation by environmental distance can explain the observed correlations. Our approach elucidated important ecological and conservation aspects of franciscana dolphins, and has the potential to increase our understanding of ecological processes influencing genetic patterns in other marine species.

Isometachromin, a new cytotoxic sesquiterpenoid from a deep water sponge of the family Spongiidae.

PubMed

McConnell, O J; Longley, R; Gunasekera, M

1992-09-15

Isometachromin (1), a new sesquiterpene-quinone that is related structurally to metachromin C (2), and the known compounds ilimaquinone (3) and 5-epi-ilimaquinone (4), were isolated from a deep water sponge in the family Spongiidae; the structure of isometachromin was elucidated by spectral methods. Isometachromin exhibits in vitro cytotoxicity against the human lung cancer cell line A549 (IC50 = 2.6 micrograms/ml), but not against P388 murine leukemia (IC 50 > or equal to 10 micrograms/ml) and also exhibits antimicrobial activity.

Five new indole alkaloids from the leaves of Rauvolfia yunnanensis.

PubMed

Geng, Chang-An; Liu, Xi-Kui

2013-09-01

Five new indole alkaloids, rauvoloids A-E (1-5), together with two known ones, raucaffrinoline (6) and perakine (7) were isolated from the leaves of Rauvolfia yunnanensis. Their structures were elucidated by extensive spectroscopic methods. Structurally, rauvoloids A (1), B-C (2-3) and D (4) with unusual substitution patterns (no substitution, Cl and (1E)-3-oxo-butenyl, respectively) at C-20, are the first examples of perakine-type alkaloids with C18 and C22 skeletons. Copyright © 2013 Elsevier B.V. All rights reserved.

Iridoids and sesquiterpenoids from the roots of Valeriana officinalis.

PubMed

Wang, Peng-Cheng; Hu, Jiang-Miao; Ran, Xin-Hui; Chen, Zhong-Quan; Jiang, He-Zhong; Liu, Yu-Qing; Zhou, Jun; Zhao, You-Xing

2009-09-01

Two new iridoids, volvaltrates A and B (1 and 2), and three new sesquiterpenoids, E-(-)-3beta,4beta-epoxyvalerenal (3), E-(-)-3beta,4beta-epoxyvalerenyl acetate (4), and mononorvalerenone (5), together with five known iridoids and two known sesquiterpenoids were isolated from the roots of Valeriana officinalis. The structures and relative configurations of 1-5 were elucidated by spectroscopic evidence. Compound 1 was an unusual iridoid with an oxygen bridge connecting C-3 and C-10, forming a cage-like structure, and compound 5 was a mononorsesquiterpenoid.

Bioactive constituents from Chinese natural medicines. XXXII. aminopeptidase N and aldose reductase inhibitors from Sinocrassula indica: structures of sinocrassosides B(4), B(5), C(1), and D(1)-D(3).

PubMed

Morikawa, Toshio; Xie, Haihui; Wang, Tao; Matsuda, Hisashi; Yoshikawa, Masayuki

2008-10-01

From the methanolic extract of the whole plant of Sinocrassula indica (Crassulaceae), six new flavonol glycosides, sinocrassosides B(4) (1), B(5) (2), C(1) (3), D(1) (4), D(2) (5), and D(3) (6), were isolated together with 30 compounds. The structures of 1-6 were elucidated on the basis of chemical and physicochemical evidence. In addition, several constituents were found to show inhibitory effects on aminopeptidase N and aldose reductase.

Two new compounds from the aerial parts of Bergenia himalaica Boriss and their anti-hyperglycemic effect in streptozotocin-nicotinamide induced diabetic rats.

PubMed

Siddiqui, Bina S; Hasan, Mashooda; Mairaj, Farah; Mehmood, Iffat; Hafizur, Rahman Md; Hameed, Abdul; Khan Shinwari, Zabta

2014-03-28

Bergenia himalaica Boriss is mainly distributed in the temperate Himalayas between altitudes of 900 and 3000m ranging from the southeastern regions in central Asia and northern regions in South Asia. The plant has a long history of its use in traditional medicine for the treatment of various diseases such as diabetes, urinary complaints, kidney stones, hemorrhagic diseases and epilepsy. The aim of this study is to isolate pure compounds from Bergenia himalaica Boriss, elucidate their structures and determine their blood glucose lowering activity to obtain additional scientific evidence for its usage in traditional medicine for the management of diabetes. The crude methanolic extract from the aerial parts of Bergenia himalaica Boriss was separated into EtOAc and water sub-extracts and the EtOAc sub-extract was further divided into petroleum ether soluble and insoluble fractions. The pet-ether insoluble fraction was subjected to fractionation through column chromatography followed by prep. TLC. The blood glucose lowering activity of the 2 new compounds was evaluated in streptozotocin-nicotinamide induced diabetic rats. Additionally, glucose-stimulated insulin secretion was measured on isolated mice islets. Two new compounds bergenicin and bergelin were isolated and their structures determined on the basis of spectral analysis. Significant decrease of blood glucose was observed at 1-h (1.0mg/kg) and 2-h (0.5mg/kg), after bergenicin administration to the diabetic rats and at 2-h (1.0mg/kg) and 3-h (0.5mg/kg), after bergelin administration. Bergenicin, but not bergelin, enhanced glucose-stimulated insulin secretion in isolated pancreatic islets. In the present studies two new compounds, bergenicin and bergelin were isolated from Bergenia himalaica Boriss and their structures were elucidated. Both the compounds showed anti-hyperglycemic effects in streptozotocin-nicotinamide induced diabetic rats. Bergenicin showed insulinotropic effect; suggesting that the anti-hyperglycemic effect is mostly due to enhancement of insulin secretion from pancreatic β-cells. Copyright © 2014 Elsevier Ireland Ltd. All rights reserved.

Absolute configuration of a tetrahydrophenanthrene from Heliotropium ovalifolium by LC-NMR of its Mosher esters.

PubMed

Guilet, David; Guntern, Alain; Ioset, Jean-Robert; Queiroz, Emerson F; Ndjoko, Karine; Foggin, Chris M; Hostettmann, Kurt

2003-01-01

A new tetrahydrophenanthrene (1, (1R,2R)-1-hydroxy-2-methoxy-6,9-dimethyl-2,3-dihydrophenanthren-4(1H)-one (heliophenanthrone)) has been isolated from the aerial parts of Heliotropium ovalifolium. Its structure was elucidated on the basis of spectroscopic data, and the absolute configuration of the asymmetric centers was determined from LC-NMR data of the Mosher ester derivatives.

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.

Monoamine oxidase inhibitors from Gentiana lutea.

PubMed

Haraguchi, Hiroyuki; Tanaka, Yasumasa; Kabbash, Amal; Fujioka, Toshihiro; Ishizu, Takashi; Yagi, Akira

2004-08-01

Three monoamine oxidase (MAO) inhibitors were isolated from Gentiana lutea. Their structures were elucidated to be 3-3''linked-(2'-hydroxy-4-O-isoprenylchalcone)-(2'''-hydroxy-4''-O-isoprenyldihydrochalcone) (1), 2-methoxy-3-(1,1'-dimethylallyl)-6a,10a-dihydrobenzo(1,2-c)chroman-6-one and 5-hydroxyflavanone. These compounds, and the hydrolysis product of 1, displayed competitive inhibitory properties against MAO-B which was more effective than MAO-A.

Labdane-type diterpenes active against acne from pine cones (Pinus densiflora).

PubMed

Sultan, Md Zakir; Jeon, Young-Min; Moon, Surk-Sik

2008-03-01

Bioassay-guided extraction and fractionation of the aqueous methanolic extract of the cones of Pinus densiflora (Pinaceae) afforded one new labdane-type diterpene aldehyde, 15-nor-14-oxolabda-8(17),12 E-diene-18-oic acid, along with eight known diterpenes. Their structures were elucidated using spectroscopic methods as well as by comparison with previously reported data. The isolates showed antibacterial (Propionibacterium acnes) and antifungal activities.

Penicillipyrones A and B, meroterpenoids from a marine-derived Penicillium sp. fungus.

PubMed

Liao, Lijuan; Lee, Jung-Ho; You, Minjung; Choi, Tae Joon; Park, Wanki; Lee, Sang Kook; Oh, Dong-Chan; Oh, Ki-Bong; Shin, Jongheon

2014-02-28

Penicillipyrones A (1) and B (2), two novel meroterpenoids, were isolated from the marine-derived fungus Penicillium sp. On the basis of the results of combined spectroscopic analyses, these compounds were structurally elucidated to be sesquiterpene γ-pyrones from a new skeletal class derived from a unique linkage pattern between the drimane sesquiterpene and pyrone moieties. Compound 2 elicited significant induction of quinone reductase.

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).

Sesquiterpene lactones from neurolaena oaxacana

PubMed

Passreiter; Sandoval-Ramirez; Wright

1999-08-01

Twelve sesquiterpene lactones, two new (1 and 2) and 10 known neurolenin-type germacranolides and furanoheliangolides (3-12) were isolated from Neurolaena oaxacana, and their structures were elucidated by NMR and GC-MS analysis. The chemotaxonomic importance of these findings is discussed. As N. lobata is used against dysenteries, neurolenin B (4) and a mixture of the neurolenins C (5) and D (6) were tested against Entamoeba histolytica and Giardia intestinalis.

New cytotoxic steroids from the leaves of Clerodendrum trichotomum.

PubMed

Xu, Rui-Lan; Wang, Rui; Ding, Lan; Shi, Yan-Ping

2013-07-01

A phytochemical investigation of the leaves of Clerodendrum trichotomum led to the isolation of five new (2-6) and two known (1 and 7) steroids, whose structures and relative configurations were elucidated by comprehensive spectroscopic analysis and by comparison of their NMR data with those of related compounds. Steroids 2 and 5 exhibited moderate cytotoxicity in vitro against HeLa cell line. Copyright © 2013 Elsevier Inc. All rights reserved.

Polycephalin B and C: Unusual Tetramic Acids from Plasmodia of the Slime Mold Physarum polycephalum (Myxomycetes).

PubMed

Nowak, Alexander; Steffan, Bert

1998-12-04

Illumination results in increased formation of metabolites 1 and 2 in the plasmodia of the slime mold Physarum polycephalum. This was determined from HPLC studies undertaken in the search for the photoactive substances involved in the "blue-light phenomenon". The isolation and structure elucidation of 1 and 2 is described. © 1998 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Four new glycosides from the stems of Dendrobium fimbriatum Hook.

PubMed

Xu, Feng-Qing; Fan, Wei-Wei; Zi, Cheng-Ting; Dong, Fa-Wu; Yang, Dan; Zhou, Jun; Hu, Jiang-Miao

2017-04-01

Four new glucosides, named as gigantol-5-O-β-d-glucopyranoside (1), 9,10-dihydro-aphyllone A-5-O-β-d-glucopyranoside (2), ficusal-4-O-β-d-glucopyranoside (3), botrydiol-15-O-β-d-glucopyranoside (4), together with eight known compounds (5-12) were isolated from the n-BuOH extract of the stems of Dendrobium fimbriatum Hook. Their structures were elucidated by the analyses of spectroscopic data.

A new compound from Stereum insigne CGMCC5.57.

PubMed

Tian, Meng-Qing; Wu, Qing-Lan; Wang, Xin; Zhang, Ke-Qin; Li, Guo-Hong

2017-04-01

Studies of the EtOAc extract of the culture broth and methanol extract of the mycelium of Stereum insigne CGMCC5.57 led to the isolation of one new dihydrobenzofuran (1) and six known compounds (2-7). The structures of compounds were elucidated mainly by HRESIMS experiments, and 1D, 2D NMR spectroscopy analysis. This is the first report about the chemical constitutes of the fungus S. insigne.

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.

Dihydroisocoumarins from Radix Glycyrrhizae.

PubMed

Zhao, Songsong; Yan, Xinjia; Zhao, Ying; Wen, Jing; Zhao, Zhenzhen; Liu, Hongwei

2018-05-11

Radix Glycyrrhizae is the rhizome of Glycyrrhiza inflata Bat., Glycyrrhiza uralensis Fisch. or Glycyrrhiza glabra L. The present paper describes the isolation and the structural elucidation of three new dihydroisocoumarins obtained from the 70% EtOH extract of Radix Glycyrrhizae. And the cytotoxic activities of these new compounds were also evaluated using four cell lines, subsequently. A pair of new dihydroisocoumarin epimers ((3R,4S)-4,8-dihydroxy-3-methyl-1-oxoisochroman-5-yl)methyl acetate (1) and ((3R,4R)-4,8-dihydroxy-3-methyl-1-oxoisochroman-5-yl)methyl acetate (2) along with a new dihydroisocoumarin (3R,4R)-4,8-dihydroxy-3,5-dimethylisochroman-1-one (3) were isolated from Radix Glycyrrhizae. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses, HR-ESI-MSand ECD calculation comparing with those of experimental CD spectra. Cytotoxic activities of the three compounds were evaluated using the HepG2, A549, LoVo and Hela cell lines, respectively. IC 50 values indicated compounds 1-3 exhibited moderate or less cytotoxic activity in vitro. Dihydroisocoumarin is not the common components in Radix Glycyrrhizae, a series of dihydroisocoumarin were obtained in this plant could be a supplement to the chemical study of this plant.

Affinity Crystallography: A New Approach to Extracting High-Affinity Enzyme Inhibitors from Natural Extracts.

PubMed

Aguda, Adeleke H; Lavallee, Vincent; Cheng, Ping; Bott, Tina M; Meimetis, Labros G; Law, Simon; Nguyen, Nham T; Williams, David E; Kaleta, Jadwiga; Villanueva, Ivan; Davies, Julian; Andersen, Raymond J; Brayer, Gary D; Brömme, Dieter

2016-08-26

Natural products are an important source of novel drug scaffolds. The highly variable and unpredictable timelines associated with isolating novel compounds and elucidating their structures have led to the demise of exploring natural product extract libraries in drug discovery programs. Here we introduce affinity crystallography as a new methodology that significantly shortens the time of the hit to active structure cycle in bioactive natural product discovery research. This affinity crystallography approach is illustrated by using semipure fractions of an actinomycetes culture extract to isolate and identify a cathepsin K inhibitor and to compare the outcome with the traditional assay-guided purification/structural analysis approach. The traditional approach resulted in the identification of the known inhibitor antipain (1) and its new but lower potency dehydration product 2, while the affinity crystallography approach led to the identification of a new high-affinity inhibitor named lichostatinal (3). The structure and potency of lichostatinal (3) was verified by total synthesis and kinetic characterization. To the best of our knowledge, this is the first example of isolating and characterizing a potent enzyme inhibitor from a partially purified crude natural product extract using a protein crystallographic approach.

Eudesmane and aromadendrane sesquiterpenoids from the Vietnamese soft coral Sinularia erecta.

PubMed

Huong, Nguyen Thi; Ngoc, Ninh Thi; Thanh, Nguyen Van; Dang, Nguyen Hai; Cuong, Nguyen Xuan; Nam, Nguyen Hoai; Thung, Do Cong; The, Ho Van; Tuan, Vo Sy; Kiem, Phan Van; Minh, Chau Van

2017-11-16

Using various chromatographic separations, eight sesquiterpenoids (1-8), including one new compound 3β,5α-dihydroxyeudesma-4(15),11-diene (1), were isolated from the MeOH extract of the Vietnamese soft coral Sinularia erecta. The structure elucidation was confirmed by spectroscopic experiments including 1D and 2D NMR and HR-ESI-MS. The cytotoxic activities against three human cancer cell lines (A-549, HeLa and PANC-1) of all isolated compounds were evaluated by MTT-based colorimetric assays. Compound 1 exhibited selective cytotoxicity against the A549 cell line with IC 50 of 14.79 ± 0.91 μM.

Anthraquinones from a Marine-Derived Streptomyces spinoverrucosus

PubMed Central

Hu, Youcai; Martinez, Elisabeth D.; MacMillan, John B.

2012-01-01

Four new anthraquinone analogs including galvaquinones A-C (1–3) and an isolation artifact 5,8-dihydroxy-2,2,4-trimethyl-6-(3-methylbutyl)anthra[9,1-de][1,3]oxazin-7(2H)-one (4) were isolated from a marine-derived Streptomyces spinoverrucosus based on activity in an image-based assay to identify epigenetic modifying compounds. The structures of 1–4 were elucidated by comprehensive NMR and MS spectroscopic analysis. Galvaquinone B (2) was found to show epigenetic modulatory activity at 1.0 μM, and exhibited moderate cytotoxicity against non-small cell lung cancer (NSCLC) cell lines Calu-3 and H2887. PMID:23057874

Complete LC/MS analysis of a Tinnevelli senna pod extract and subsequent isolation and identification of two new benzophenone glucosides.

PubMed

Terreaux, Christian; Wang, Qi; Ioset, Jean-Robert; Ndjoko, Karine; Grimminger, Wolf; Hostettmann, Kurt

2002-04-01

The hydroalcoholic extract of Tinnevelli senna is widely used as a laxative phytomedicine. In order to improve the knowledge of the chemical composition of this extract, LC/MS and LC/MS(n) studies were performed, allowing the on-line identification of most of the known constituents, i. e., flavonoids, anthraquinones and the typical dianthronic sennosides. However, the identity of four compounds could not be ascertained on-line under the given LC/MS conditions. These substances were isolated and their structures elucidated as kaempferol, the naphthalene derivative tinnevellin 8-glucoside and two new carboxylated benzophenone glucosides.

Cathepsin B inhibitory activities of three new phthalate derivatives isolated from seahorse, Hippocampus Kuda Bleeler.

PubMed

Li, Yong; Qian, Zhong-Ji; Kim, Se-Kwon

2008-12-01

Three new phthalate acid derivatives, 2,12-diethyl-11-methylhexadecyl 2-ethyl-11-methylhexadecyl phthalate (1), 2-ethyldecyl 2-ethylundecyl phthalate (2), and bis(2-ethyldodecyl) phthalate (3), were isolated from seahorse, Hippocampus Kuda Bleeler, together with a known natural analog bis(2-ethylheptyl) phthalate (4). The structures of these compounds were elucidated mainly by means of the comprehensive analysis of their NMR spectroscopic data. The four phthalate derivatives showed dose-dependent cathepsin B inhibitions activities with IC(50) values of 0.13 mM (1), 0.21 mM (2), 0.18 mM (3), and 0.29 mM (4), respectively.

A new cinnamic acid glycoside from roots of Heracleum dissectum.

PubMed

Wang, Zhi-Gang; Mi, Jie; Wang, Xin-Rui; Huo, Ya-Yu; Peng, Ya-Jie; Zhang, Hai-Min; Gao, Yang; Zhang, Hai-Long

2018-01-01

From the roots of Heracleum dissectum Lebb., one new cinnamic acid glycoside derivative named dissectumoside (1), together with eight known compounds including three phenolics, three phenolic glycosides and two phenylpropanoic glycoside were isolated using various chromatographic methods. Among them compound 2-9 was isolated from the plant for the first time. Their structures were elucidated and identified on the basis of their physicochemical properties and by extensive analyses of NMR spectroscopy and high-resolution mass spectrometry. The results of triglyceride accumulation screening in 3T3-L1 cells showed that compounds 1, 5 and 9 exhibited significantly accelerating activities of adipogenesis in adipocytes.

Antioxidant neolignan and phenolic glucosides from the fruit of Euterpe oleracea.

PubMed

Hu, Jian; Zhao, Jianping; Khan, Shabana I; Liu, Qiang; Liu, Yang; Ali, Zulfiqar; Li, Xing-Cong; Zhang, Shui-han; Cai, Xiong; Huang, Hui-yong; Wang, Wei; Khan, Ikhlas A

2014-12-01

Three new glucosides, namely, (-)-7R8S-7',8'-dihydroxy-dihydrodehydroconiferyl alcohol-9-O-β-D-glucopyranoside (1), (+)-7S8R-7',8'-dihydroxy-dihydrodehydroconiferyl alcohol-9-O-β-D-glucopyranoside (2) and 4-hydroxy-2-methoxyphenyl 1-O-[6-(hydrogen 3-hydroxy-3-methylpentanedioate)]-β-D-glucopyranoside (3), along with 6 known compounds were isolated from the fruit of Euterpe oleracea Mart. Their structures were elucidated based on spectroscopic analyses including NMR, HR-ESI-MS and CD. All the isolated compounds demonstrated significant antioxidant activity and 2 displayed moderate cytotoxicity against HL-60 cells. Copyright © 2014 Elsevier B.V. All rights reserved.

Two new chalcone glycosides from the stems of Entada phaseoloides.

PubMed

Zhao, Zhong-xiang; Jin, Jing; Lin, Chao-zhan; Zhu, Chen-chen; Liu, Yi-ming; Lin, Ai-hua; Liu, Ying-xiang; Zhang, Li; Luo, Hua-feng

2011-10-01

Two new chalcone glycosides 4'-O-(6″-O-galloyl-β-d-glucopyranosyl)-2',4-dihydroxychalcone (1) and 4'-O-(6″-O-galloyl-β-d-glucopyranosyl)-2'-hydroxy-4-methoxychalcone (2) together with one known chalcone glycoside 4'-O-β-d-glucopyranosyl-2'-hydroxy-4-methoxychalcone (3) were isolated from the stems of Entada phaseoloides. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analysis, including HSQC, HMBC, (1)H-(1)H COSY, and chemical evidences. This is the first report of chalcone-type compounds isolated from the genus Entada. Copyright © 2011 Elsevier B.V. All rights reserved.

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.

Antiproliferative triterpene saponins from Entada africana.

PubMed

Cioffi, Giuseppina; Dal Piaz, Fabrizio; De Caprariis, Paolo; Sanogo, Rokia; Marzocco, Stefania; Autore, Giuseppina; De Tommasi, Nunziatina

2006-09-01

Nine new ester saponins (1-9) were isolated from the roots of Entada africana. Their structures were elucidated by 1D and 2D NMR experiments including 1D and 2D TOCSY, DQF-COSY, HSQC, and HMBC spectroscopy, as well as ESIMS analysis, and chemical methods. The aglycon moieties were found to be echinocystic acid for compounds 1, 2, 4-6, 8, and 9 and acacic acid for 3 and 7. All isolated compounds were tested for their antiproliferative activity against the J774.A1, HEK-293, and WEHI-164 cell lines. Moderate to high cytotoxic potency was found for almost all compounds tested.

Two new phthalide dimers from the rhizomes of Ligusticum chuanxiong.

PubMed

Wei, Wei; Xu, Wei; Yang, Xiu-Wei

2017-07-01

Two pairs of diastereoisomers, namely (3'Z)-(3S,8S,3a'S,6'R)-4,5-dehydro-3.3a',8.6'-diligustilide (1) and (3'Z)-(3S,8R,3a'S,6'R)-4,5-dehydro-3.3a',8.6'-diligustilide (3), chuanxiongdiolide R3 (2), and chuanxiongdiolide R1 (4), were isolated from the 95% ethanolic aqueous extract of the rhizomes of Ligusticum chuanxiong. Among these Phthalide dimers, compounds 1 and 2 were new ones. The structures of the new isolates were elucidated based on spectroscopic data analyses, and their absolute configurations were determined by comparison of experimental and calculated electronic circular dichroism spectra.

Two new compounds from the flowers of Rhododendron molle.

PubMed

Chen, Shao-Nong; Bao, Guan-Hu; Wang, Li-Quan; Qin, Guo-Wei

2013-09-01

To study the chemical constituents of the flowers of Rhododendron molle. Compounds were isolated by repeated chromatography over silica gel and Sephadex LH-20. Structures were elucidated based on spectral techniques, mainly 1D- and 2D-NMR and mass spectrometric analyses. Two compounds (1 and 2) were isolated. Compounds 1 and 2 were identified as two new compounds: 2α, 10α-epoxy-3β, 5β, 6β, 14β, 16α-hexahydroxy-grayanane and benzyl 2, 6-dihydroxybenzoate-6-O-α-L-rhamnopyranosyl-(1→3)-β-D-glucopyranoside, respectively. Copyright © 2013 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.

Colletotrilactam A-D, novel lactams from Colletotrichum gloeosporioides GT-7, a fungal endophyte of Uncaria rhynchophylla.

PubMed

Wei, Bo; Yang, Zhong-Duo; Chen, Xiao-Wei; Zhou, Shuang-Yan; Yu, Hai-Tao; Sun, Jing-Yun; Yao, Xiao-Jun; Wang, Yong-Gang; Xue, Hong-Yan

2016-09-01

Four novel lactams, colletotrilactam A-D (1-4), along with six known compounds (5-10) were isolated from the culture broth of Colletotrichum gloeosporioides GT-7, a fungal endophyte of Uncaria rhynchophylla. The structures of these compounds were elucidated by comprehensive NMR spectroscopy. Isolates were tested for monoamine oxidase (MAO) inhibitory activity and compound 9 showed potent MAO inhibitory activity with IC50 value of 8.93±0.34μg/mL, when the IC50 value of iproniazid as a standard was 1.80±0.5μg/mL. Copyright © 2016 Elsevier B.V. All rights reserved.

Chrodrimanins K-N and Related Meroterpenoids from the Fungus Penicillium sp. SCS-KFD09 Isolated from a Marine Worm, Sipunculus nudus.

PubMed

Kong, Fan-Dong; Ma, Qing-Yun; Huang, Sheng-Zhuo; Wang, Pei; Wang, Jun-Feng; Zhou, Li-Man; Yuan, Jing-Zhe; Dai, Hao-Fu; Zhao, You-Xing

2017-04-28

Six new meroterpenoids, chrodrimanins K-N (1-4), including two uncommon chlorinated ones (1 and 2), and verruculides B2 (5) and B3 (6), as well as seven known ones (7-13), were isolated from the fermentation broth of Penicillium sp. SCS-KFD09 isolated from a marine worm, Sipunculus nudus, from Haikou Bay, China. The structures including the absolute configurations of the new compounds were unambiguously elucidated by spectroscopic data, X-ray diffraction analysis, and ECD spectra analysis along with quantum ECD calculations. In addition, the X-ray crystal structures and absolute configurations of two previously reported meroterpenoids, chrodrimanins F (9) and A (11), are described for the first time. Compounds 1, 4, and 7 displayed anti-H1N1 activity with IC 50 values of 74, 58, and 34 μM, respectively, while compound 5 showed weak inhibitory activity against Staphylococcus aureus with an MIC of 32 μg/mL.

Anticholinesterase inhibitory activity of quaternary alkaloids from Tinospora crispa.

PubMed

Yusoff, Mashitah; Hamid, Hazrulrizawati; Houghton, Peter

2014-01-20

Quaternary alkaloids are the major alkaloids isolated from Tinospora species. A previous study pointed to the necessary presence of quaternary nitrogens for strong acetylcholinesterase (AChE) inhibitory activity in such alkaloids. Repeated column chromatography of the vine of Tinospora crispa extract led to the isolation of one new protoberberine alkaloid, 4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g]quinolizinium (1), along with six known alkaloids-dihydrodiscretamine (2), columbamine (3), magnoflorine (4), N-formylannonaine (5), N-formylnornuciferine (6), and N-trans-feruloyltyramine (7). The seven compounds were isolated and structurally elucidated by spectroscopic analysis. Two known alkaloids, namely, dihydrodiscretamine and columbamine are reported for the first time for this plant. The compounds were tested for AChE inhibitory activity using Ellman's method. In the AChE inhibition assay, only columbamine (3) showed strong activity with IC50 48.1 µM. The structure-activity relationships derived from these results suggest that the quaternary nitrogen in the skeleton has some effect, but that a high degree of methoxylation is more important for acetylcholinesterase inhibition.

Hydrolyzable tannins of tamaricaceous plants. V. Structures of monomeric-trimeric tannins and cytotoxicity of macrocyclic-type tannins isolated from Tamarix nilotica (1).

PubMed

Orabi, Mohamed A A; Taniguchi, Shoko; Sakagami, Hiroshi; Yoshimura, Morio; Yoshida, Takashi; Hatano, Tsutomu

2013-05-24

Three new ellagitannin monomers, nilotinins M5-M7 (1-3), a dimer, nilotinin D10 (4), and a trimer, nilotinin T1 (5), together with three known dimers, hirtellin D (7) and tamarixinins B (8) and C (9), and a trimer, hirtellin T2 (6), were isolated from Tamarix nilotica dried leaves. The structures of the tannins were elucidated by intensive spectroscopic methods and chemical conversions into known tannins. The new trimer (5) is a unique macrocyclic type whose monomeric units are linked together by an isodehydrodigalloyl and two dehydrodigalloyl moieties. Additionally, dimeric and trimeric macrocyclic-type tannins isolated from T. nilotica in this study were assessed for possible cytotoxic activity against four human tumor cell lines. Tumor-selective cytotoxicities of the tested compounds were higher than those of synthetic and natural potent cytotoxic compounds, including polyphenols, and comparable with those of 5-fluorouracil and melphalan.

Histrionicotoxins: roentgen-ray analysis of the novel allenic and acetylenie spiroalkaloids isolated from a Colombian frog, Dendrobates histrionicus.

PubMed

Daly, J W; Karle, I; Myers, C W; Tokuyama, T; Waters, J A; Witkop, B

1971-08-01

The structures and absolute configuration of two unique alkaloids isolated from the Colombian frog, Dendrobates histrionicus, have been elucidated by Roentgen-ray (x-ray) crystallography. Histrionicotoxin is (2pR, 6S, 7pS, 8aS)-7-(cis-1-buten-3-ynyl)-8-hydroxy-2-(cis-2-penten-4- ynyl)-1-azaspiro[5.5] undecane, while in dihydro-isohistrionicotoxin the acetylenic 2-pentenynyl side chain is replaced by an allenic 2-(3,4 pentadienyl) substituent. Dendrobates histrionicus exhibits remarkable interpopulational variations in amounts and composition of skin toxins, in behavior, and in phenotypic characters, aspects of which are illustrated in a color plate. The histrionico-toxins are the third class of alkaloids isolated from the defensive skin secretions of Neotropical (Dendrobatidae) frogs.

Quinolizidine alkaloids from the curare adjuvant Clathrotropis glaucophylla.

PubMed

Sagen, Anne Lise; Gertsch, Jürg; Becker, Rita; Heilmann, Jörg; Sticher, Otto

2002-12-01

The bark of Clathrotropis glaucophylla (Fabaceae) is used as admixture of curare arrow poison by the Yanomami; Amerindians in Venezuela. A new quinolizidine alkaloid (QA), (-)-13alpha-hydroxy-15alpha-(1-hydroxyethyl)-anagyrine [(-)-clathrotropine], was isolated from the alkaloid extract of C. glaucophylla bark, together with eleven known QAs: (-)-anagyrine, (-)-thermopsine, (-)-baptifoline, (-)-epibaptifoline, (-)-rhombifoline, (-)-tinctorine, (-)-cytisine, (-)-N-methylcytisine, (-)-lupanine, (-)-6alpha-hydroxylupanine and (+)-5,6-dehydrolupanine. The isolation and structure elucidation were performed with the aid of chromatographic (TLC, HPLC and CC) and spectroscopic (UV and 1D/2D NMR) methods, and mass spectrometry. To our knowledge, this is the first time quinolizidine alkaloids have been isolated from an arrow poison ingredient. It is also the first report on Clathrotropis species being used for preparation of arrow poison.

[Glycosides from flowers of Jasminum officinale L. var. grandiflorum].

PubMed

Zhao, Gui-qin; Xia, Jing-jing; Dong, Jun-xing

2007-10-01

To study the chemical constituents of the flower of Jasminum officinale L. var. grandiflorum. The compounds were isolated and purified by re-crystallization and chromatography on silica gel and Sephadex LH-20 column. Their structures were elucidated on the physicochemical properties and spectral analysis. Seven glycosides were identified as kaempferol-3-O-alpha-L-rhamnopyranosyl (1-->3)-[alpha-L-rhamnopyranosyl (1-->6)]-beta-D-galactopyranoside (I), kaempferol-3-O-rutinoside (II), 7-ketologanin (III), oleoside-11-methyl ester (IV), 7-glucosyl-l1-methyl oleoside (V), ligstroside (VI), oleuropein (VII). Compound I is a new compound. Compounds III and V were isolated from the family of Jasminum for the first time and compounds II, IV and VI were isolated from Jasminum officinale L. var. grandiflorum for the first time.

Chemical compounds from Chenopodium album Linn.

NASA Astrophysics Data System (ADS)

Zheng, Wei

2017-06-01

Bioactive components from Chenopodium album Linn. were isolated and identified in this research. Light petroleum, dichloromethane and n-BuOH were firstly applied to partition the 75% EtOH extract of Chenopodium album Linn. which were then subjected to normal-phase silica, ODS silica gel column chromatography and semi-preparative HPLC chromatography. By the employment of NMR method in this study, chemical structures of the compounds were elucidated. Three known compounds were isolated from Chenopodium album Linn., and identified as Isolariciresinol 4-O-β-D-glucopyranoside (1), (7’S, 8R, 8’R)-Isolariciresinol (2) and (7’S, 8R, 8’S)-Isolariciresinol (3) by comparison of their spectral data with references. This is the first time that isolation of the compounds mentioned above from Chenopodium album Linn. was achieved.

Cycloartane triterpenes from marine green alga Cladophora fascicularis

NASA Astrophysics Data System (ADS)

Huang, Xinping; Zhu, Xiaobin; Deng, Liping; Deng, Zhiwei; Lin, Wenhan

2006-12-01

Six cycloartanes were isolated from ethanol extract of marine green alga Cladophora fascicularis by column chromatography. Procedure of isolation and description of these compounds are given in this paper. The structures were elucidated as (1). 24-hydroperoxycycloart-25- en-3β-ol; (2). cycloart-25-en-3β 24-diol; (3). 25-hydroperoxycycloart-23-en-3β-ol; (4). cycloart-23-en-3β, 25-diol; (5). cycloart-23, 25-dien-3β-ol; and (6). cycloart-24-en-3β-ol by spectroscopic (MS, ID and 2D NMR) data analysis. Cycloartane derivatives are widely distributed in terrestrial plants, but only few were obtained in the alga. All these compounds that have been isolated from terrestrial plants, were found in the marine alga for the first time.

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.

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.

Cadinane sesquiterpenes from Curcuma phaeocaulis with their inhibitory activities on nitric oxide production in RAW 264.7 cells.

PubMed

Ma, Jianghao; Wang, Ying; Liu, Yue; Gao, Suyu; Ding, Liqin; Zhao, Feng; Chen, Lixia; Qiu, Feng

2015-06-01

Four new cadinane-type sesquiterpenes named phacadinanes A-D (1-4) were isolated from the rhizomes of Curcuma phaeocaulis. Their structures were elucidated by 1D and 2D NMR, as well as accurate mass measurements. Compound 4 was the first example of a rare 4,5-seco-cadinane sesquiterpene isolated from the Zingiberaceae family. Furthermore, inhibitory effects of the isolated compounds on nitric oxide production in LPS-activated macrophages were evaluated. Compounds 1 and 2 showed strong inhibitory activities on NO production with IC50 values of 3.88±0.58 and 2.25±0.71 μM, respectively. A possible biogenetic pathway for 4,5-seco-cadinane sesquiterpene (4) was postulated. Copyright © 2015 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.

Xylopiana A, a Dimeric Guaiane with a Case-Shaped Core from Xylopia vielana: Structural Elucidation and Biomimetic Conversion.

PubMed

Zhang, Ya-Long; Zhou, Xu-Wei; Wang, Xiao-Bing; Wu, Lin; Yang, Ming-Hua; Luo, Jun; Yin, Yong; Luo, Jian-Guang; Kong, Ling-Yi

2017-06-02

Xylopiana A (1), a dimeric guaiane with an unprecedented pentacyclo[5.2.1.0 1,2 .0 4,5' .0 5,4' ]decane-3,2'-dione core, and three biosynthetically related intermediates, compounds 2-4, were isolated from the leaves of Xylopia vielana. Their structures and absolute configurations were determined by a combination of spectroscopic data, X-ray crystallography, electronic circular dichroism calculations, and chemical conversion. The structure of known vielanin A was revised to be compound 3. Compound 4 exerted a 3.7-fold potentiation effect on doxorubicin susceptibility at the tested concentration of 10 μM.

Chemical constituents with anti-allergic activity from the root of Edulis Superba, a horticultural cultivar of Paeonia lactiflora.

PubMed

Shi, Yan-Hong; Zhu, Shu; Tamura, Takayuki; Kadowaki, Makoto; Wang, Zhengtao; Yoshimatsu, Kayo; Komatsu, Katsuko

2016-04-01

The methanolic extract and its subfractions from the dried root of Edulis Superba, a horticultural cultivar of Paeonia lactiflora Pallas, showed potent anti-allergic effect as inhibition of immunoglobulin E (IgE)-mediated degranulation in rat basophil leukemia (RBL)-2H3 cells. Bioassay-guided fractionation led to the isolation of 26 compounds, including a new norneolignan glycoside, paeonibenzofuran (1), together with 25 known ones (2-26). The chemical structure of the new compound was elucidated on the basis of spectroscopic and chemical evidences. Among the isolated compounds, mudanpioside E (5) with paeoniflorin-type skeleton and quercetin (16) showed potent inhibitory activity against a degranulation marker, β-hexosaminidase release with IC50 values of 40.34 and 25.05 μM, respectively. A primary structure-activity relationship of these components was discussed.

Neopetrosiquinones A and B, Sesquiterpene Benzoquinones Isolated from the Deep-water Sponge Neopetrosia cf. proxima

PubMed Central

Winder, Priscilla L.; Baker, Heather L.; Linley, Patricia; Guzmán, Esther; Pomponi, Shirley A.; Diaz, M. Cristina; Reed, John K.; Wright, Amy E.

2011-01-01

Two new marine-derived sesquiterpene benzoquinones which we designate as neopetrosiquinone A (1) and B (2), have been isolated from a deep-water sponge of the family Petrosiidae. The structures were elucidated on the basis of their spectroscopic data. Compounds 1 and 2 inhibit the in vitro proliferation of the DLD-1 human colorectal adenocarcinoma cell line with IC50 values of 3.7 and 9.8 μM, respectively, and the PANC-1 human pancreatic carcinoma cell line with IC50 values of 6.1 and 13.8 μM, respectively. Neopetrosiquinone A (1) also inhibited the in vitro proliferation of the AsPC-1 human pancreatic carcinoma cell line with an IC50 value of 6.1 μM. The compounds are structurally related to alisiaquinone A, cyclozonarone and xestoquinone. PMID:22014756

Sesquiterpenes from the essential oil of Curcuma wenyujin and their inhibitory effects on nitric oxide production.

PubMed

Xia, Guiyang; Zhou, Li; Ma, Jianghao; Wang, Ying; Ding, Liqin; Zhao, Feng; Chen, Lixia; Qiu, Feng

2015-06-01

Three new sesquiterpenes including a new elemane-type sesquiterpene, 5βH-elem-1,3,7,8-tetraen-8,12-olide (1), and two new carabrane-type sesquiterpenes, 7α,11-epoxy-6α-methoxy-carabrane-4,8-dione (2) and 8,11-epidioxy-8-hydroxy-4-oxo-6-carabren (3), together with eight known sesquiterpenes (4-11) were isolated from Curcuma wenyujin Y. H. Chen et C. Ling. Their structures were elucidated based on extensive spectroscopic analyses. A possible biogenetic scheme for the related compounds was postulated. All of the isolated compounds were tested for inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages. Meanwhile, preliminary structure-activity relationships for these compounds are discussed. Copyright © 2015 Elsevier B.V. All rights reserved.

Chemical study of the Chinese medicine Pi Han Yao

PubMed Central

PENG, TENG; ZHAO, FURONG; CHEN, XIAOYU; JIANG, GUIHUA; WANG, SHAONAN

2016-01-01

The aim of the present study was to ivnestigate the chemical constituents of the Chinese medicine Pi Han Yao (Gueldenstaedtia delavayi Franch) decoction. Following this, the quantitative determination of the formononetin and maackiain content in Pi Han Yao was established. The chemical constituents were isolated by column chromatography and their structures were elucidated by analysis of spectrometric data and chemical evidence. High-performance liquid chromatography (HPLC) was used for the determination of the formononetin and maackiain content in Pi Han Yao. Seven flavanones were isolated from the Pi Han Yao decoction. Five of the chemical structures were elucidated as 1, 7,2′-dihydroxy-4′-methoxy-isoflavanol; 2, maackiain; 3, formononetin-7-O-β-D-glucoside; 4, formononetin; and 5, 9-(β-D-ribofuranosyl)-adenosine. The other two compounds and their structures require further study. Additionally, the linear range of formononetin and maackiain were 0.03992–0.3992 and 0.0292–0.292 µg, and their recoveries were 100.31 and 100.44%. To the best of our knowledge, compounds 1–5 were obtained from Pi Han Yao for the first time. The HPLC method use for determination of formononetin and maackiain in Pi Han Yao was simple, accurate and reliable. Findings from the present study suggest that these methods may be used to evaluate the quality of Pi Han Yao and provide an experience basis for quality standards of this medicinal material. PMID:26893842

New 2-arylbenzofuran metabolite from cell cultures of Morus alba.

PubMed

Zhang, De-Wu; Tao, Xiao-Yu; Yu, Li-Yan; Dai, Jun-Gui

2015-01-01

A new 2-arylbenzofuran compound, 5-dehydroxy-moracin U (1), along with 10 known compounds (2-11), were isolated from cell cultures of Morus alba. Their structures were elucidated on the basis of extensive spectroscopic analyses. The anti-inflammatory activity assay of 1-8 showed that 2 and 8 exhibited significant inhibitory effect on LPS-induced NO production with the values of 76.4% and 98.7% at 10(- 5) M, respectively.

A cytotoxic cyclic heptapeptide from the seeds of Annona cherimola.

PubMed

Wélé, Alassane; Zhang, Yanjun; Ndoye, Idrissa; Brouard, Jean-Paul; Pousset, Jean-Louis; Bodo, Bernard

2004-09-01

From a methanol extract of the seeds of Annona cherimola, a new cyclic heptapeptide, cherimolacyclopeptide C, has been isolated. The structure was elucidated on the basis of the MS/MS fragmentation using a Q-TOF mass spectrometer equipped with an ESI source, extensive 2D NMR experiments, and chemical degradation. Cherimolacyclopeptide C exhibited significant in vitro cytotoxic activity against KB cells, with an IC(50) value of 0.072 microM.

A New Terminal Cyano Group-containing Benzodiazepine Alkaloid from the Mangrove Endophytic Fungus Penicillium sp. .

PubMed

Li, Jing; Zhong, Yi-sheng; Yuan, Jie; Zhu, Xun; Lu, Yong-jun; Lin, Yong-cheng; Liu, Lan

2015-09-01

A new benzodiazepine alkaloid containing terminal cyano group has been isolated from a mangrove endophytic fungus, Penicillium 299#. Structure elucidation was determined by 1D and 2D NMR spectroscopy and the absolute configuration was determined by electronic circular dichroism (ECD). The new compound showed no cytotoxic activities in vitro against human cancer lines MDA-MB-435, HepG2, HCT-116, and Calu-3.

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.

Phenolic glycosides and ionone glycoside from the stem of Sargentodoxa cuneata.

PubMed

Chang, Jun; Case, Ryan

2005-12-01

Four phenolic glycosides, cuneatasides A-D (1-4), and one ionone glycoside cuneataside E (5), together with seven known phenolic compounds (6-12) were isolated from the water-soluble constituents of the stem of Sargentodoxa cuneata (Sargentodoxaceae). Their structures were elucidated by spectroscopic analysis. In vitro tests for antimicrobial activity showed compounds 1 and 2 to possess significant activity against two Gram-positive organisms, Staphylococcus aureus and Micrococcus epidermidis.

Bispolides, novel 20-membered ring macrodiolide antibiotics from microbispora.

PubMed

Okujo, Noriyuki; Iinuma, Hironobu; George, Annie; Eim, Khor Siew; Li, Tan Lee; Ting, Ng Szu; Jye, Tan Chin; Hotta, Kunimoto; Hatsu, Masahiro; Fukagawa, Yasuo; Shibahara, Seiji; Numata, Keiichi; Kondo, Shinichi

2007-03-01

Seven new related compounds named bispolides A1, A2, A3, B1, B2a, B2b and B3, have been found in a culture of Microbispora sp. A34030, isolated from a Malaysian soil sample. The planar structures were elucidated to be new 20-membered ring macrodiolide antibiotics on the basis of MS and NMR spectroscopic analyses. These antibiotics showed a good anti-MRSA activity in vitro.

Two new triterpenoid saponins from Dianthus superbus L.

PubMed

Chen, Xia; Luo, Jian-Guang; Kong, Ling-Yi

2010-06-01

Two new triterpenoid saponins (1 and 2) were isolated from the dried aerial parts of Dianthus superbus L. (Caryophyllaceae). Their structures were elucidated on the basis of spectral data to be 3-O-beta-D-glucopyranosyl olean-9(11),12-diene-23,28-dioic acid 28-O-beta-D-glucopyranoside (1) and 3-O-beta-D-glucopyranosyl olean-11,13(18)-diene-23,28-dioic acid 28-O-beta-D-glucopyranoside (2).

Two new triterpenoid saponins from the aerial parts of Anemone taipaiensis.

PubMed

Li, Hui; Wang, Xiao-Yang; Wang, Xia-Yin; Hua, Dong; Liu, Yang; Tang, Hai-Feng

2015-05-01

Phytochemical study on the aerial parts of Anemone taipaiensis for the first time led to the isolation of two new oleanane-type triterpenoid saponins 1 and 2, together with four known saponins (3-6). Their structures were elucidated by extensive spectroscopic analysis and chemical evidences. Saponins 2-4 exhibited cytotoxicity against human glioblastoma U251MG cell line with IC50 values ranging from 1.56 to 80.62 μM.

Curvularides A-E: antifungal hybrid peptide-polyketides from the endophytic fungus Curvularia geniculata.

PubMed

Chomcheon, Porntep; Wiyakrutta, Suthep; Aree, Thammarat; Sriubolmas, Nongluksna; Ngamrojanavanich, Nattaya; Mahidol, Chulabhorn; Ruchirawat, Somsak; Kittakoop, Prasat

2010-09-24

Five new hybrid peptide-polyketides, curvularides A-E (1-5), were isolated from the endophytic fungus Curvularia geniculata, which was obtained from the limbs of Catunaregam tomentosa. Structure elucidation for curvularides A-E (1-5) was accomplished by analysis of spectroscopic data, as well as by single-crystal X-ray crystallography. Curvularide B (2) exhibited antifungal activity against Candida albicans, and it also showed synergistic activity with a fluconazole drug.

Toni Morrison's Beloved: a journey through the pain of grief.

PubMed

Pass, Olivia McNeely

2006-01-01

This paper elucidates the structure of Toni Morrison's novel, Beloved, using the framework of human emotions in response to grieving and death as developed by Elisabeth Kubler-Ross. Through her studies of terminally ill patients, Kubler-Ross identified five stages when approaching death: denial and isolation, anger, bargaining, depression and acceptance. These stages accurately fill the process that the character Sethe experiences in the novel as she learns to accept her daughter's death.

Sesquiterpenes and a phenylpropanoid from Cordia trichotoma.

PubMed

de Menezes, Jane Eire S A; Machado, Francisca Elane A; Lemos, Telma Leda G; Silveira, Edilberto R; Braz Filho, Raimundo; Pessoa, Otília Deusdênia L

2004-01-01

Two new secondary metabolites, the phenylpropanoid 3-(2',4',5'-trimethoxyphenyl)propanoic acid (1) and the sesquiterpene (+)-1beta,4beta,6alpha-trihydroxyeudesmane (2) were isolated from the heartwood of Cordia trichotoma Vell., along with the known sesquiterpenes (-)-1beta,4beta,7alpha-trihydroxyeudesmane (3) and (+)-1beta,4beta,11-trihydroxyoppositane (4). Their structures were elucidated by means of spectroscopic data interpretation, mainly 1D and 2D NMR and mass spectrometry.

Houttuynoids A-E, anti-herpes simplex virus active flavonoids with novel skeletons from Houttuynia cordata.

PubMed

Chen, Shao-Dan; Gao, Hao; Zhu, Qin-Chang; Wang, Ya-Qi; Li, Ting; Mu, Zhen-Qiang; Wu, Hong-Ling; Peng, Tao; Yao, Xin-Sheng

2012-04-06

Houttuynoids A-E (1-5), a new type of flavonoid with houttuynin tethered to hyperoside, and their presumed biosynthetic precursor hyperoside (6) were isolated from the whole plant of Houttuynia cordata. Their structures were elucidated by analysis of 1D and 2D NMR. A hypothetical biogenetic pathway for houttuynoids A-E was proposed. Compounds 1-5 exhibited potent anti-HSV (herpes simplex viruses) activity.

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.

7-epi-griffonilide, a new lactone from Bauhinia pentandra: complete 1H and 13C chemical shift assignments.

PubMed

Almeida, Macia C S DE; Souza, Luciana G S; Ferreira, Daniele A; Pinto, Francisco C L; Oliveira, Débora R DE; Santiago, Gilvandete M P; Monte, Francisco J Q; Braz-Filho, Raimundo; Lemos, Telma L G DE

2017-01-01

A new lactone, 7-epi-griffonilide (1), and six known compounds, 2, 3a - 3c, 4a and 4b, were isolated from the leaves of Bauhinia pentandra (Fabaceae). The structures elucidation of 1 and 2 were based on detailed 2D NMR techniques and spectral comparison with related compounds, leading to complete assignment of the 1H and 13C NMR spectra.

Highly oxygenated ent-pimarane-type diterpenoids from the Chinese liverwort Pedinophyllum interruptum and their allelopathic activities.

PubMed

Liu, Na; Li, Rui-Juan; Wang, Xiao-Ning; Zhu, Rong-Xiu; Wang, Lei; Lin, Zhao-Min; Zhao, Yu; Lou, Hong-Xiang

2013-09-27

Ten highly oxygenated ent-pimarane-type diterpenoids, pedinophyllols A-J (1-10), were isolated from the Chinese liverwort Pedinophyllum interruptum. Their structures were determined by comprehensive analysis of spectroscopic data together with single-crystal X-ray diffraction analysis. The absolute configurations were elucidated by comparison of experimental and theoretically calculated electronic circular dichroism spectra. Allelopathic testing showed that several new diterpenoids inhibited germination of Arabidopsis thaliana seeds.

Bioactivity-guided isolation of polyacetylenes with inhibitory activity against NO production in LPS-activated RAW264.7 macrophages from the rhizomes of Atractylodes macrocephala.

PubMed

Yao, Chun-Mei; Yang, Xiu-Wei

2014-02-03

The rhizome of Atractylodes macrocephala (Compositae) is one of the most well-known traditional Chinese medicine in China, Japan and Korea, which has a long history of use for the treatment of splenic asthenia, edema, anorexia, and excessive perspiration, etc. As active compounds of anti-inflammatory activity of this medicinal plant have not been fully elucidated, the aim of this study was to isolate and identify the active constituents inhibiting nitric oxide (NO) production from the rhizomes of A. macrocephala. Inhibitory activity against NO production in lipopolysaccharide-activated RAW264.7 macrophages was evaluated by Griess reaction. Fifteen polyacetylenes were isolated from the active ethyl acetate extract using activity-guided screening. The structures of all compounds were elucidated by spectroscopic methods and comparison with published data. The compounds were further tested for their inhibitory activity against NO production. Seven new polyacetylenes, named atractylodemaynes A-G (1-7), along with eight known ones (8-15) were isolated. Compound 14 was isolated for the first time from the rhizomes of A. macrocephala. The study showed that the tested compounds exhibited inhibitory activity against NO production in a dose-dependent manner. Among them, compounds 10, 11 and 12 had relatively stronger inhibitory effect with IC50 values of 28, 23 and 19μM, respectively. The results demonstrated that the polyacetylenes might greatly contribute to the anti-inflammatory activity of the rhizomes of A. macrocephala. © 2013 Elsevier Ireland Ltd. All rights reserved.

Peptaibols from Two Unidentified Fungi of the Order Hypocreales with Cytotoxic, Antibiotic, and Anthelmintic Activities

PubMed Central

Ayers, Sloan; Ehrmann, Brandie M.; Adcock, Audrey F.; Kroll, David J.; Carcache de Blanco, Esperanza J.; Shen, Qi; Swanson, Steven M.; Falkinham, Joseph O.; Wani, Mansukh C.; Mitchell, Sheila M.; Pearce, Cedric J.; Oberlies, Nicholas H.

2012-01-01

As part of an ongoing investigation of filamentous fungi for anticancer leads, an active culture was identified from the Mycosynthetix library (MSX 70741, of the order Hypocreales, Ascomycota). The fungal extract exhibited cytotoxic activity against the H460 (human non-small cell lung carcinoma) cell line, and bioactivity-directed fractionation yielded peptaibols 1–12 and harzianums A (13) and B (14). Structure elucidation of 1–12 was facilitated by high-resolution MS/MS obtained on a Thermo LTQ Orbitrap XL using Higher-Energy Collisional Dissociation (HCD) and by high field NMR (950 MHz). The absolute configuration was determined by Marfey’s analysis of the individual amino acids; the time required for such analysis was decreased via the development of a 10 min UPLC method. The isolated peptaibols (1–12), along with three other peptaibols isolated and elucidated from a different fungus (MSX 57715) of the same Order (15–17), were examined for activity in a suite of biological assays, including those for cytotoxic, antibacterial, and anthelmintic activities. PMID:22744757

Bio-prospecting of soil Streptomyces and its bioassay-guided isolation of microbial derived auxin with antifungal properties.

PubMed

Saravana Kumar, P; Yuvaraj, P; Gabrial Paulraj, M; Ignacimuthu, S; Abdullah Al-Dhabi, N

2018-06-05

The present study was aimed to isolate bioactive actinomycetes with antifungal properties. Twenty-seven distinct soil derived actinomycetes were investigated for their antifungal activities. Among these, one isolate exhibited significant antifungal activity. Phenotypic and 16s rRNA gene sequence analysis strongly suggested that the active isolate BG4 belonged to the genus Streptomyces. Further, the chemical investigation of the active extract resulted in the isolation of a major compound and it was structurally elucidated as phenyl acetic acid (PAA). PAA exhibited promising antifungal activity with 100% inhibition, ranging from 31.25 to 25μg/mL. It is to be noted that PAA is naturally occurring and biologically active auxin. In addition, it has also been hypothesized that phytohormone endorsing the source of soil-symbionts has similar pathways for synthesizing compounds and its congeners of host due to horizontal gene transfer. These findings demonstrate that microbially derived phytohormone can be used to treat fungal infections. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

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.

Study of the Stereochemistry and Oxidation Mechanism of Plant Polyphenols, Assisted by Computational Chemistry.

PubMed

Matsuo, Yosuke

2017-01-01

In recent years, plant polyphenols have attracted great attention due to their wide range of biological activities. Certain kinds of polyphenols have complex structures; therefore, it is difficult to elucidate their total structure, including stereochemistry. In this study, we reinvestigated the stereostructures of two major C-glycosidic ellagitannins contained in Quercus plants, vescalagin and castalagin, and revised their stereostructures based on theoretical calculations of spectroscopic data. We also determined the structures of quercusnins A and B, isolated from the sapwood of Quercus crispula, based on theoretical calculations of NMR data. The oxidation mechanism of polyphenols has not been entirely elucidated. Therefore, we have also studied the oxidation mechanism of tea catechins during black tea production. Our investigation of the oxidation mechanism of black tea pigment theaflavins revealed that the difference in the position of the galloyl ester affords different oxidation products of theaflavins. In addition, oxidation products of pyrogallol-type catechins could be classified into three types-dehydrotheasinensins, theacitrins, and proepitheaflagallins; their detailed production and degradation mechanisms were also examined.

Separation and structural characterization of the new synthetic cannabinoid JWH-018 cyclohexyl methyl derivative "NE-CHMIMO" using flash chromatography, GC-MS, IR and NMR spectroscopy.

PubMed

Angerer, Verena; Bisel, Philippe; Moosmann, Bjoern; Westphal, Folker; Auwärter, Volker

2016-09-01

Synthetic cannabinoids have become an integral part of the drugs of abuse market since many years. The most frequent form of consumption for this class of substances is smoking of herbal mixtures purchased via the Internet. In this article the identification and structure elucidation of a new synthetic cannabinoid, [1-(cyclohexylmethyl)-1H-indol-3-yl](naphthalen-1-yl)methanone, is described. The compound was found along with 5F-ADB in a 'herbal mixture' called 'Jamaican Gold Extreme', which was sent to our laboratory in the context of a suspected intoxication. For isolation of the substance a flash chromatography separation was applied. Structure elucidation was performed using gas chromatography-mass spectrometry (GC-MS), gas chromatography solid-state infrared (GC-sIR) and nuclear magnetic resonance (NMR) analysis. The new compound can be described as the cyclohexyl methyl derivative of the first generation synthetic cannabinoid JWH-018, and the authors suggest to use "NE-CHMIMO" as a semisystematic name. Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.

Two new cucurbitane triterpenoids from the seeds of Momordica charantia.

PubMed

Ma, Lin; Yu, Ai-Hua; Sun, Li-Li; Gao, Wan; Zhang, Meng-Meng; Su, Ya-Lun; Liu, Hua; Ji, Teng-Fei; Li, Di-Zao

2014-01-01

Two new cucurbitane triterpenoids 1 and 2 were isolated, together with six known compounds, from the seeds of Momordica charantia L. The structures of new compounds were determined to be 3-O-{[β-d-galactopyranosyl(1 → 6)]-O-β-d-galactopyranosyl}-23(R), 24(R), 25-trihydroxycucur-bit-5-ene (1), 3-O-[β-d-galactopyranosyl]-25-O-β-d-galactopyranosyl-7(R), 22(S), 23(R), 24(R), 25-pentahydroxycucurbit-5-ene (2), respectively. Their structures were elucidated by the combination of mass spectrometry, one- and two-dimensional NMR experiments and chemical reactions.

Triterpenoid saponins from Echinopsis macrogona (Cactaceae).

PubMed

Okazaki, Sachie; Kinoshita, Kaoru; Ito, Satoru; Koyama, Kiyotaka; Yuasa, Hiroshi; Takahashi, Kunio

2011-01-01

Triterpene saponins, pachanosides C1, E1, F1 and G1 (1-4), and bridgesides A1, C1, C2, D1, D2, E1 and E2 (5-11) were isolated from Echinopsis macrogona. Compounds 1-4 were saponins with pachanane type triterpene saponins, while the others (5-11) were oleanane type triterpene saponins. While the aglycones of 2-4 and 8-11 were hitherto unknown, the structure of pachanol C was revised in this paper. Their structures were elucidated on the basis of chemical and physicochemical evidence. Copyright © 2010 Elsevier Ltd. All rights reserved.

B-535a, b and c, new sphingosine kinase inhibitors, produced by a marine bacterium; taxonomy, fermentation, isolation, physico-chemical properties and structure determination.

PubMed

Kono, K; Tanaka, M; Mizuno, T; Kodama, K; Ogita, T; Kohama, T

2000-08-01

In the course of our screening for inhibitors of sphingosine kinase, we found a series of active compounds in a culture broth of a novel marine bacterium, SANK 71896. The structures of the compounds, named B-5354a, b and c, were elucidated by a combination of spectroscopic analyses to be new esters of 4-amino-3-hydroxybenzoic acid with long-chain unsaturated alcohols. B-5354a, b and c inhibit sphingosine kinase activity with IC50 values of 21, 58 and 38 microm, respectively.

Identification of two novel proanthocyanidins in green Tea.

PubMed

Lakenbrink, C; Engelhardt, U H; Wray, V

1999-11-01

The isolation and structural elucidation of epiafzelechingallate-(4beta-->8)-epicatechingallate (EAG-4beta-->8-ECG) and epiafzelechingallate-(4beta-->6)-epicatechingallate (EAG-4beta-->6-ECG) in green tea samples are described. The combination of various 2D NMR techniques allowed a full structural determination of the underivatized proanthocyanidins even though broadening of the signals did not allow observation of some key correlations that characterize the location of the interflavonoid linkage. The differences in the NMR spectra of the new compounds allowed formulation of criteria for the discrimination between the 4-->6 and 4-->8 isomers in this type of compound.

New phenethyl alcohol glycosides from Stachys parviflora.

PubMed

Ahmad, Viqar Uddin; Arshad, Saima; Bader, Sadia; Ahmed, Amir; Iqbal, Shazia; Tareen, Rasool Buksh

2006-01-01

Phytochemical investigations of the whole plant of Stachys parviflora (Lamiaceae) resulted in the isolation of two new phenethyl alcohol glycosides. The structures of the new compounds named parviflorosides A and B were established as 2-(3,4-dihydroxyphenyl)-ethyl-O-alpha-L-rhamnopyranosyl-(1 --> 2)-4-O-E-caffeoyl-beta-D-glucopyranoside (1) and 2-(3,4-dihydroxyphenyl)-ethyl-O-alpha-L-rhamnopyranosyl-(1 --> 2)-6-O-E-caffeoyl-beta-D-glucopyranoside (2), respectively. The structure elucidation of the new compounds was based primarily on 1D and 2D NMR analysis, including COSY, HMBC and HMQC correlations.

[Study on chemical constituents from rhizome of Rabdosia flavida].

PubMed

Zhao, Ming-Zao; Li, Jin-Qiang; Zhang, Yu; Zhang, Xue-Jiao; Jiang, Bei

2014-07-01

To study the chemical constituents from the rhizome of Rabdosia flavida. The compounds were isolated and purified by various chromatographic methods, and their structures were elucidated on the basis of spectral data and physicochemical properties. Ten compounds were obtained from ethyl acetate fraction of the 70% acetone extract of Rabdosia flavida rhizome and identified as ferruginol (1), dehydrocostuslactone (2), taraxasterol (3), oleic acid (4), ursolic cid (5), coniferyl aldehyde (6), oleanolic acid (7), 6,12, 15-trihydroxy-5, 8,11, 13-abietetra-7-one (8), 5α, 8α-epidioxyergosta-6,22-dien-3β-ol (9), and daucosterol (10). All the compounds are isolated from Rabdosia flavida for the first time.

Chlorotheolides A and B, Spiroketals Generated via Diels-Alder Reactions in the Endophytic Fungus Pestalotiopsis theae.

PubMed

Liu, Ling; Han, Yu; Xiao, Junhai; Li, Li; Guo, Liangdong; Jiang, Xuejun; Kong, Lingyi; Che, Yongsheng

2016-10-28

Chlorotheolides A (1) and B (2), two new spiroketals possessing the unique [4,7]methanochromene and dispiro-trione skeletons, respectively, and their putative biosynthetic precursors, 1-undecen-2,3-dicarboxylic acid (3) and maldoxin (4), were isolated from the solid substrate fermentation of the plant endophytic fungus Pestalotiopsis theae (N635). Their structures were elucidated based on NMR spectroscopic data and electronic circular dichroism calculations. Biogenetically, compounds 1 and 2 could be generated from the co-isolated 3 and 4 via Diels-Alder reactions. Chlorotheolide (2) showed an antiproliferative effect against the human tumor cell line HeLa and induced an autophagic process in the cells.

Trichopeptides A and B, trichocyclodipeptides A-C, new peptides from the ascomycete fungus Stagonospora trichophoricola.

PubMed

Chen, Zhengkun; Xu, Xiuli; Ren, Jinwei; Wang, Wenzhao; Liu, Xingzhong; Li, Erwei

2017-08-01

Trichopeptides A (1) and B (2), new linear tetrapeptide and tripeptide, respectively, and three new diketopiperazines trichocyclodipeptides A-C (3-5) were isolated from the fermentation of the ascomycete fungus Stagonospora trichophoricola, a fungus isolated from the soil sample surrounding the fruiting body of Ophiocordyceps sinensis in Maqin Country, Qinghai Province, People's Republic of China. Their structures were primarily elucidated by interpretation of NMR and MS experiments. The absolute configurations of 1-5 were assigned through Marfey's method on their acid hydrolyzates. Compound 3 showed antifungal activity against Candida albicans with the IC 50 and MIC values of 22 and 90 μg ml -1 , respectively.

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.

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.

Amino Acid Conjugated Anthraquinones from the Marine-Derived Fungus Penicillium sp. SCSIO sof101.

PubMed

Luo, Minghe; Cui, Zhaomeng; Huang, Hongbo; Song, Xianqin; Sun, Aijun; Dang, Yongjun; Lu, Laichun; Ju, Jianhua

2017-05-26

Emodacidamides A-H (1-8), natural products featuring anthraquinone-amino acid conjugates, have been isolated from a marine-derived fungus, Penicillium sp. SCSIO sof101, together with known anthraquinones 9 and 10. The planar structures of 1-8 were elucidated using a combination of NMR spectroscopy and mass spectrometry. The absolute configurations of the amino acid residues were confirmed using Marfey's method and chiral-phase HPLC analyses. Additionally, isolates were evaluated for possible immunomodulatory and cytotoxic activities. Emodacidamides A (1), C (3), D (4), and E (5) inhibited interleukin-2 secretion from Jurkat cells with IC 50 values of 4.1, 5.1, 12, and 5.4 μM, respectively.

A sterol and spiroditerpenoids from a Penicillium sp. isolated from a deep sea sediment sample.

PubMed

Li, Yan; Ye, Dezan; Shao, Zongze; Cui, Chengbin; Che, Yongsheng

2012-02-01

A new polyoxygenated sterol, sterolic acid (1), three new breviane spiroditerpenoids, breviones I-K (2-4), and the known breviones (5-8), were isolated from the crude extract of a Penicillium sp. obtained from a deep sea sediment sample that was collected at a depth of 5115 m. The structures of 1-4 were elucidated primarily by NMR experiments, and 1 was further confirmed by X-ray crystallography. The absolute configurations of 2 and 3 were deduced by comparison of their CD spectra with those of the model compounds. Compounds 2 and 5 showed significant cytotoxicity against MCF-7 cells, which is comparable to the positive control cisplatin.

Fudecalone, a new anticoccidial agent produced by Penicillium sp. FO-2030.

PubMed

Tabata, N; Tomoda, H; Masuma, R; Iwai, Y; Omura, S

1995-01-01

Penicillium sp. FO-2030, a soil isolate, was found to produce a new anticoccidial compound. The active compound, designated fudecalone, was isolated from the fermentation broth of the producing strain by solvent extraction, silica gel column chromatography and preparative HPLC. The structure of fudecalone was elucidated to be 3,3a,6,6a,7,8,9,10-octahydro-1-hydroxy-4,7,7-trimethyl-1H-naphtho[1,8a- c]furan-6-one mainly by spectroscopic studies including various NMR measurements. The anticoccidial activity using cell systems indicated that schizont formation of monensin-resistant Eimeria tenella was completely inhibited by fudecalone at concentrations more than 16 microM.

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.

A new saponin from Acanthopanax koreanum with anti-inflammatory activity.

PubMed

Dat, Le Duc; Thao, Nguyen Phuong; Luyen, Bui Thi Thuy; Tai, Bui Huu; Woo, Mi Hee; Manzoor, Zahid; Ali, Irshad; Koh, Young Sang; Kim, Young Ho

2017-03-01

Twelve saponins were isolated from the leaves of Acanthopanax koreanum, including one new lupane-type triterpene glycoside, named acankoreoside R (1), together with 11 known triterpenoid saponins (2-12). Their structures were elucidated by 1D and 2D nuclear magnetic resonance (NMR), mass spectroscopic data (MS). All of the fractions and isolated saponins were evaluated for anti-inflammatory activities in lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells (BMDCs) by ELISA. Among them, compounds 1-5, 7, 10, and 12 showed strong inhibitions towards interleukin-12 (IL-12) production with IC 50 values ranging from 1.59 to 5.46 µM. Other compounds were weak or inactive toward IL-12 p40 production.

Two new triterpenoid glycosides isolated from Aesculus assamica GRIFF.

PubMed

Liu, Hongwei; Zhang, Xue; Gao, Hao; Wang, Nali; Jin, Sanlin; Cai, Bin; Yao, Xinsheng; Cai, Guoping

2005-10-01

Phytochemical study of the ethanol extract of the seeds of Aesculus assamica led to the isolation of two new triterpenoid saponins. The structure of the new compounds were elucidated on the basis of spectral data to be 28-O-acetyl-21-O-(4-O-angeloyl)-6-deoxy-beta-glucopyranosyl-3-O-[beta-glucopyranosyl(1-2)-O-[beta-glucopyranosyl(1-4)]-beta-glucuronopyranosyl]protoaescigenin (1), and 21-O-(4-O-angeloyl)-6-deoxy-beta-glucopyranosyl-3-O-[beta-glucopyranosyl(1-2)-O-[beta-glucopyranosyl(1-4)]-beta-glucuronopyranosyl]protoaescigenin (2). Their in vitro bioactivity against plant pathogenic fungus Pyricularia oryzae and cytotoxicity against K562 and HCT-15 cell lines were evaluated.

Three new amino acid derivatives from edible mushroom Pleurotus ostreatus.

PubMed

Lu, Xiao-Jie; Feng, Bao-Min; Chen, Shao-Fei; Zhao, Dan; Chen, Gang; Wang, Hai-Feng; Pei, Yue-Hu

2017-12-01

Three new amino acid derivatives, oxalamido-L-phenylalanine methyl ester (1), oxalamido-L-leucine methyl ester (2), and lumichrome hydrolyzate (3), together with nine known compounds (4-12), were isolated from the solid culture of edible mushroom Pleurotus ostreatus. Their structures were elucidated on the basis of extensive spectroscopic analysis. The absolute configurations of 1 and 2 were established by the chiral synthesis and confirmed by circular dichroism (CD) analysis of their total synthesis products and natural isolates. All new compounds were evaluated for their antioxidant effects, antimicrobial activities, and cytotoxic activity. Compounds 1-3 showed weak antifungal activities against Candida albicans with minimum inhibitory concentration (MIC) value of 500 μg/ml.

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.

New benzophenone and quercetin galloyl glycosides from Psidium guajava L.

PubMed

Matsuzaki, Keiichi; Ishii, Rie; Kobiyama, Kaori; Kitanaka, Susumu

2010-07-01

New benzophenone and flavonol galloyl glycosides were isolated from an 80% MeOH extract of Psidium guajava L. (Myrtaceae) together with five known quercetin glycosides. The structures of the novel glycosides were elucidated to be 2,4,6-trihydroxybenzophenone 4-O-(6''-O-galloyl)-beta-D: -glucopyranoside (1, guavinoside A), 2,4,6-trihydroxy-3,5-dimethylbenzophenone 4-O-(6''-O-galloyl)-beta-D: -glucopyranoside (2, guavinoside B), and quercetin 3-O-(5''-O-galloyl)-alpha-L: -arabinofuranoside (3, guavinoside C) by NMR, MS, UV, and IR spectroscopies. Isolated phenolic glycosides showed significant inhibitory activities against histamine release from rat peritoneal mast cells, and nitric oxide production from a murine macrophage-like cell line, RAW 264.7.

Furanodictine A and B: amino sugar analogues produced by cellular slime mold Dictyostelium discoideum showing neuronal differentiation activity.

PubMed

Kikuchi, H; Saito, Y; Komiya, J; Takaya, Y; Honma, S; Nakahata, N; Ito, A; Oshima, Y

2001-10-19

We investigated the constituents of Dictyostelium discoideum to clarify the diversity of secondary metabolites of Dictyostelium cellular slime molds and to explore biologically active substances that could be useful in the development of novel drugs. From a methanol extract of the multicellular fruit body of D. discoideum, we isolated two novel amino sugar analogues, furanodictine A (1) and B (2). They are the first 3,6-anhydrosugars to be isolated from natural sources. Their relative structures were elucidated by spectral means, and the absolute configurations were confirmed by asymmetric syntheses of 1 and 2. These furanodictines potently induce neuronal differentiation of rat pheochromocytoma (PC-12) cells.

Phytochemical constituents and chemosystematic significance of Chrozophora tinctoria (L.) Raf.

PubMed

Marzouk, Mona M; Hussein, Sameh R; Kassem, Mona E S; Kawashty, Salwa A; El Negoumy, Sabry I M

2016-07-01

Twelve compounds were isolated from Chrozophora tinctoria (L.) Raf. They were identified as kaempferol, kaempferol 3-O-β-glucopyranoside, kaempferol 3-O-(6″-α-rhamnopyranosyl)-β-glucopyranoside, quercetin, quercetin 3-O-β-glucopyranoside, quercetin 3-O-(6″-α-rhamnopyranosyl)-β-glucopyranoside, apigenin, apigenin 7-O-β-glucopyranoside, acacetin, gallic acid, methyl gallate and β-sitosterol-3-O-β-glucopyranoside. Their structures were elucidated by chemical and spectral methods. Furthermore, chemosystematics of the isolated compounds is briefly discussed. It was indicated that C. tinctoria is the only species of Chrozophora that has the capability to synthesis kaempferol aglycone and their glycosides, and the finding is supported by its distinct morphological and anatomical aspects.

New sesquiterpene lactones from Ambrosia cumanensis Kunth.

PubMed

Jimenez-Usuga, Nora Del Socorro; Malafronte, Nicola; Cotugno, Roberta; De Leo, Marinella; Osorio, Edison; De Tommasi, Nunziatina

2016-09-01

Eleven sesquiterpene lactones, including three new natural products (1-3), were isolated from the n-butanolic extract of Ambrosia cumanensis Kunth. aerial parts. The structure of all isolated compounds was elucidated by 1D- and 2D-NMR, and MS analyses. All compounds were tested for their antiproliferative activity on HeLa, Jurkat, and U937 cell lines. Compound 3, 2,3-dehydropsilostachyn C, showed cytotoxic activity with different potency in all cell lines. By means of flow cytometric studies, compound 3 was demonstrated to induce in Jurkat cells a G2/M cell cycle block, while in U937 elicited both cytostatic and cytotoxic responses. Copyright © 2016 Elsevier B.V. All rights reserved.

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.

Dihydro-β-agarofuran sesquiterpenes from celastraceae species as anti-tumour-promoting agents: Structure-activity relationship.

PubMed

Núñez, Marvin J; Jiménez, Ignacio A; Mendoza, Cristina R; Chavez-Sifontes, Marvin; Martinez, Morena L; Ichiishi, Eiichiro; Tokuda, Ryo; Tokuda, Harukuni; Bazzocchi, Isabel L

2016-03-23

Inhibition of tumour promotion in multistage chemical carcinogenesis is considered a promising strategy for cancer chemoprevention. In an ongoing investigation of bioactive secondary metabolites from Celastraceae species, five new dihydro-β-agarofuran sesquiterpenes (1-5), named Chiapens A-E, and seventeen known ones, were isolated from Maytenus chiapensis. Their structures were elucidated by extensive NMR spectroscopic and mass spectrometric techniques, and their absolute configurations were determined by circular dichroism studies, chemical correlations and biogenic means. The isolated compounds, along with twenty known sesquiterpenes, previously isolated from Zinowiewia costaricensis, have been tested for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorpol-13-acetate (TPA). Thirty three compounds from this series showed stronger effects than that of β-carotene, the reference inhibitor. The structure-activity relationship (SAR) analysis revealed that the type of substituent, in particular at the C-1 position of the sesquiterpene scaffold, was able to modulate the anti-tumour promoting activity. Compounds 3, 6, and 33 showed significant effects in an in vivo two-stage mouse-skin carcinogenesis model. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

Diversity of exophillic acid derivatives in strains of an endophytic Exophiala sp.

PubMed

Cheikh-Ali, Zakaria; Glynou, Kyriaki; Ali, Tahir; Ploch, Sebastian; Kaiser, Marcel; Thines, Marco; Bode, Helge B; Maciá-Vicente, Jose G

2015-10-01

Members of the fungal genus Exophiala are common saprobes in soil and water environments, opportunistic pathogens of animals, or endophytes in plant roots. Their ecological versatility could imply a capacity to produce diverse secondary metabolites, but only a few studies have aimed at characterizing their chemical profiles. Here, we assessed the secondary metabolites produced by five Exophiala sp. strains of a particular phylotype, isolated from roots of Microthlaspi perfoliatum growing in different European localities. Exophillic acid and two previously undescribed compounds were isolated from these strains, and their structures were elucidated by spectroscopic methods using MS, 1D and 2D NMR. Bioassays revealed a weak activity of these compounds against disease-causing protozoa and mammalian cells. In addition, 18 related structures were identified by UPLC/MS based on comparisons with the isolated structures. Three Exophiala strains produced derivatives containing a β-d-glucopyranoside moiety, and their colony morphology was distinct from the other two strains, which produced derivatives lacking β-d-glucopyranoside. Whether the chemical/morphological strain types represent variants of the same genotype or independent genetic populations within Exophiala remains to be evaluated. Copyright © 2015 Elsevier Ltd. All rights reserved.

Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae).

PubMed

Siatka, Tomáš; Adamcová, Markéta; Opletal, Lubomír; Cahlíková, Lucie; Jun, Daniel; Hrabinová, Martina; Kuneš, Jiří; Chlebek, Jakub

2017-07-14

Alzheimer's disease is an age-related, neurodegenerative disorder, characterized by cognitive impairment and restrictions in activities of daily living. This disease is the most common form of dementia with complex multifactorial pathological mechanisms. Many therapeutic approaches have been proposed. Among them, inhibition of acetylcholinesterase, butyrylcholinesterase, and prolyl oligopeptidase can be beneficial targets in the treatment of Alzheimer's disease. Roots, along with aerial parts of Argemone platyceras , were extracted with ethanol and fractionated on an alumina column using light petrol, chloroform and ethanol. Subsequently, repeated preparative thin-layer chromatography led to the isolation of (+)-laudanosine, protopine, (-)-argemonine, allocryptopine, (-)-platycerine, (-)-munitagine, and (-)-norargemonine belonging to pavine, protopine and benzyltetrahydroisoquinoline structural types. Chemical structures of the isolated alkaloids were elucidated by optical rotation, spectroscopic and spectrometric analysis (NMR, MS), and comparison with literature data. (+)-Laudanosine was isolated from A. platyceras for the first time. Isolated compounds were tested for human blood acetylcholinesterase, human plasma butyrylcholinesterase and recombinant prolyl oligopeptidase inhibitory activity. The alkaloids inhibited the enzymes in a dose-dependent manner. The most active compound (-)-munitagine, a pavine alkaloid, inhibited both acetylcholinesterase and prolyl oligopeptidase with IC 50 values of 62.3 ± 5.8 µM and 277.0 ± 31.3 µM, respectively.

Phthalide derivatives with antifungal activities against the plant pathogens isolated from the liquid culture of Pestalotiopsis photiniae.

PubMed

Yang, Xiao-Long; Zhang, Su; Hu, Qiong-Bo; Luo, Du-Qiang; Zhang, Yan

2011-11-01

Three new phthalide derivatives (1-3) named 5-(3'-methyl-2'-butenyl)-2-hydroxy-3-methoxy-4-methylbenzoic acid (1), 5-(3'-carboxyl-3'-methyl-2E-allyloxy)-3-methoxy-4-methylphthalide (2) and 5-(3',3'-dimethylallyloxy)-2-methoxycarbonyl-3-methoxy-4-methylbenzoic acid (3) together with six known phthalide derivatives named 5-(3',3'-dimethylallyloxy)-3-methoxy-4-methylphthalide (4), zinnimidine (5), 5-(3',3'-dimethylallyloxy)-3-methoxy-4-methylphthalide (6), 5-(3',3'-dimethylallyloxy)-3-methoxy-4-methylphthalic acid (7), zinniol anhydride (8) and porriolide (9) were isolated from the liquid culture of the plant endophytic fungus Pestalotiopsis photiniae isolated from the Chinese Podocarpaceae plant Podocarpus macrophyllus. Their structures were elucidated by extensive spectroscopic analysis. Compounds 1-9 displayed significant antifungal activities against three plant pathogens.

Histrionicotoxins: Roentgen-Ray Analysis of the Novel Allenic and Acetylenic Spiroalkaloids Isolated from a Colombian Frog, Dendrobates histrionicus

PubMed Central

Daly, John W.; Karle, Isabella; Myers, Charles W.; Tokuyama, Takashi; Waters, James A.; Witkop, Bernhard

1971-01-01

The structures and absolute configuration of two unique alkaloids isolated from the Colombian frog, Dendrobates histrionicus, have been elucidated by Roentgen-ray (x-ray) crystallography. Histrionicotoxin is (2pR, 6S, 7pS, 8aS)-7-(cis-1-buten-3-ynyl)-8-hydroxy-2-(cis-2-penten-4- ynyl)-1-azaspiro[5.5] undecane, while in dihydro-isohistrionicotoxin the acetylenic 2-pentenynyl side chain is replaced by an allenic 2-(3,4 pentadienyl) substituent. Dendrobates histrionicus exhibits remarkable interpopulational variations in amounts and composition of skin toxins, in behavior, and in phenotypic characters, aspects of which are illustrated in a color plate. The histrionico-toxins are the third class of alkaloids isolated from the defensive skin secretions of Neotropical (Dendrobatidae) frogs. Images PMID:5288773

[Chemical constituents of Rauvolfia verticillata].

PubMed

Hong, Bo; Li, Wen-Jing; Zhao, Chun-Jie

2012-06-01

The study on the Rauvolfia verticillata (Lour.) Baill., which belongs to Apocynaceae, was carried out to look for its chemical constituents and pharmacological activity. The isolation and purification were performed by chromatography on silica gel, Sephadex LH-20 and ODS (octadecyl silane) open column. The structures of obtained compounds were elucidated on the basis of physicochemical properties and spectral analysis. Three indole alkaloids and one acridone alkaloid were isolated from chloroform layer extract and identified as ajmalicine B (1), sandwicine (2), raunescine (3) and 7-hydroxynoracronycine (4) separately. Ajmalicine B (1) is a new compound belonging to indole alkaloid. Compound 4 as an acridone alkaloid was a new type compound isolated from Rauvolfia genus for the first time. We also did some biological activity research on the new type compound (4) to explore other pharmacological activities in addition to antihypertensive activity.

ACETYL CHOLINESTERASE AND BUTYRYL CHOLINESTERASE INhIBITORY ACTIVITIES OF ZALEYA PENTANDRA.

PubMed

Afzal, Samina; Chaudhry, Bashir Ahmad; Afzal, Khurram; Saeed, Javeria; Akash, Sajd Hamid; Qadir, Muhammad Imran

2017-05-01

The aim of this study was to reveal acetyl cholinesterase (AchE) and butyryl cholinesterase (BchE) inhibitory activities of Zaleya pentandra. The aerial parts of the plant were air, freeze-dried and powdered. The extraction was carried out with methanol at room temperature for 24 h. The extract was concentrated on rotavapor and fractioned by column chromatography. The isolation and purification afforded amorphous solid which was subjected to physical, chemical and spectroscopic techniques i.e., UV, IR, H-NMR, "C-NMR and HREI-MS for the structure elucidation of the isolated compound. The compound was concluded as "Pentandradione" a novel compound. AchE and BchE inhibitory activities were estimated. The result showed that the isolated extract possessed significant activity against butyryl cholinesterase as compared to standard eserine while the extract lacks acetyl cholinesterase inhibitory activity.

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.

Report on maloine, a new alkaloid discovered from G. maloi: Structural characterization and biological activity

NASA Astrophysics Data System (ADS)

Çela, Dorisa; Nepravishta, Ridvan; Lazari, Diamanto; Gaziano, Roberta; Moroni, Gabriella; Pica, Francesca; Paci, Maurizio; Abazi, Sokol

2017-02-01

Gymnospermium maloi Kit Tan, & Shuka is a new endemic species of the genus Gymnospermium Spach which has been described recently from the southern part of Albania. The members of this genus are poorly studied for what it concern the secondary metabolites in general and the class of alkaloids in particular. In fact from Gymnospermium genus, there are only few alkaloids characterized, (namely albertramine, albertidine, and albertine) isolated from G. albertii. Until now the chemical composition and the structure elucidation of other possible secondary metabolites, especially alkaloids, remain largely unknown. Here we report, for the first time, the structure of a new alkaloid isolated from G. maloi, designated by us as maloine, and obtained by the use of 2D homonuclear and heteronuclear NMR spectroscopy, FTIR, UV, Fluorescence and HPLC/MS spectra. The biological activity of the crude extract of Gymnospermium maloi and of its alkaloid maloine, was evaluated in vitro on human chronic myeloid leukemia cell line K562 and results herewith reported.

Asparagine-linked oligosaccharides on lutropin, follitropin, and thyrotropin: structural elucidation of the sulfated and sialylated oligosaccharides on bovine, ovine, and human pituitary glycoprotein hormones

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

Green, E.D.; Baenziger, J.U.

1988-01-05

The authors have elucidated the structures of the anionic asparagine-linked oligosaccharides present on the glycoprotein hormones lutropin (luteinizing hormone), follitropin (follicle-stimulating hormone), and thyrotropin (thyroid-stimulating hormone). Purified hormones, isolated from bovine, ovine, and human pituitaries, were digested with N-glycanase, and the released oligosaccharides were reduced with NaB(/sup 3/H)/sub 4/. The /sup 3/H-labeled oligosaccharides from each hormone were then fractionated by anion-exchange high performance liquid chromatography (HPLC) into populations differing in the number of sulfate and/or sialic acid moieties. The sulfated, sialylated, and sulfated/sialylated structures, which together comprised 67-90% of the asparagine-linked oligosaccharides on the pituitary glycoprotein hormones, were highly heterogeneousmore » and displayed hormone- as well as animal species-specific features. A previously uncharacterized dibranched oligosaccharide, bearing one residue each of sulfate and sialic acid, was found on all of the hormones except bovine lutropin. In this study, they describe the purification and detailed structural characterizations of the sulfated, sialylated, and sulfated/sialylated oligosaccharides found on lutropin, follitropin, and thyrotropin from several animal species.« less

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.

Two new compounds from the plant endophytic fungus Pestalotiopsis versicolor.

PubMed

Yang, Xiao-Long; Huang, Le; Li, Hai-Ying; Yang, Deng-Feng; Li, Zhuang-Zhuang

2015-01-01

A new coumarin, 4,6-dihydroxy-7-formyl-3-methylcoumarin (1), and an α-pyrone derivative, 6-[(7S,8R)-8-propyloxiran-1-yl]-4-methoxy-pyran-2-one (2), together with four known α-pyrone derivatives (3-6), were isolated from the broth extract of the plant endophytic fungus Pestalotiopsis versicolor. Their structures were elucidated by extensive spectroscopic analysis and by comparison of the chemical shift values with those of related known compounds.

Antibacterial polyketides from the jellyfish-derived fungus Paecilomyces variotii.

PubMed

Liu, Juan; Li, Famei; Kim, Eun La; Li, Jian Lin; Hong, Jongki; Bae, Kyung Sook; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H

2011-08-26

Four new polyketides (1-4) were isolated from the fungus Paecilomyces variotii, which was derived from the jellyfish Nemopilema nomurai. The planar structures and relative configurations of these polyketides were elucidated on the basis of spectroscopic analyses, including 2D NMR experiments. The compounds showed inhibitory activity against pathogenic bacteria including methicillin-resistant Staphylococcus aureus 3089 and multi-drug-resistant Vibrio parahemolyticus 7001 with MIC values in the range 5-40 μg/mL.

Suvanine analogs from a Coscinoderma sp. marine sponge and their cytotoxicities against human cancer cell lines.

PubMed

Lee, Jeong-Woo; Lee, Hyi-Seung; Shin, Jongheon; Kang, Jong Soon; Yun, Jieun; Shin, Hee Jae; Lee, Jong Seok; Lee, Yeon-Ju

2015-06-01

Nine suvanine analogs including suvanine phenethylammonium salt and two new compounds were isolated from the marine sponge Coscinoderma sp., collected from Chuuk State, Federated States of Micronesia. The structures of the new compounds were elucidated by 2D NMR and HRMS analyses. Suvanine and a new analog exhibited weak but selective cytotoxicity against colon (HCT-15), lung (NCI-H23), stomach (NUGC-3), and prostate (PC-3) cancer cell lines.

New sesquiterpenes from Euonymus europaeus (Celastraceae).

PubMed

Descoins, Charles; Bazzocchi, Isabel López; Ravelo, Angel Gutiérrez

2002-02-01

A new sesquiterpene evoninate alkaloid (1), and two sesquiterpenes (2, 3) with a dihydro-beta-agarofuran skeleton, along with three known sesquiterpenes (4-6), were isolated from the seeds of Euonymus europaeus. Their structures were elucidated by high resolution mass analysis, and one- and two-dimensional (1D and 2D) NMR spectroscopy, including homonuclear and heteronuclear correlation [correlation spectroscopy (COSY), rotating frame Overhauser enhancement spectroscopy (ROESY), heteronuclear single quantum coherence (HSQC), and heteronuclear multiple bond correlation (HMBC)] experiments.

Pyrrolo[2,1-a]isoquinoline and pyrrole alkaloids from Sinomenium acutum.

PubMed

Lv, Hai-Ning; Zeng, Ke-Wu; Zhao, Ming-Bo; Jiang, Yong; Tu, Peng-Fei

2018-03-01

Two pyrrolo[2,1-a]isoquinolines (1 and 2) and three pyrrole alkaloids (3-5), including three new ones, named sinopyrines A-C (1-3), were isolated from the 95% EtOH extract of the stems and rhizomes of Sinomenium acutum (Thumb.) Rehd. et Wils. The structures of the new compounds were elucidated on the basis of spectroscopic data. This is the first report of pyrrole-bearing natural compounds from the family Menispermaceae.

Insektenpheromone

NASA Astrophysics Data System (ADS)

Bestmann, H. J.; Vostrowsky, O.

1982-10-01

Pheromones — semiochemicals used by insects for intraspecific chemical communication — can be isolated and with special analytical techniques their chemical structure elucidated. With stereoselective synthesis methods, presented by the preparation of sex attractants and aggregating pheromones of moths and beetles, respectively, a synthetic access to compounds is given which can be used for behavior manipulation of insects. Aside the importance of these compounds for investigations of the sensoric process the possibility of their application in an integrated and biological pest control is discussed.

New chromanone acids with antibacterial activity from Calophyllum brasiliense.

PubMed

Cottiglia, Filippo; Dhanapal, Boopathy; Sticher, Otto; Heilmann, Jörg

2004-04-01

Six novel chromanone acids (1-6) were isolated from the bark of Calophyllum brasiliense Cambess. Their structures were elucidated on the basis of 1D and 2D NMR experiments, as well as mass spectrometry. All compounds showed moderate to strong antibacterial activity against Bacillus cereus and Staphylococcus epidermidis, with 1 and 2 being most active. None of the compounds were cytotoxic against KB, Jurkat T, and myosarcoma cancer cells up to 20 microg/mL.

Antimicrobial prenylated dihydrochalcones from Eriosema glomerata.

PubMed

Awouafack, Maurice D; Kouam, Simeon F; Hussain, Hidayat; Ngamga, Dieudonne; Tane, Pierre; Schulz, Barbara; Green, Ivan R; Krohn, Karsten

2008-01-01

Two new natural dihydrochalcones exhibiting antimicrobial properties together with six known compounds were isolated from the Cameroonian medicinal plant Eriosema glomerata. The structures of the new dihydrochalcones were elucidated as 2',4'-dihydroxy-4-methoxy-3'-( gamma, gamma-dimethylallyl)dihydrochalcone and 2',4'-dihydroxy-3'-( gamma, gamma-dimethylallyl)dihydrochalcone by detailed spectroscopic analysis. The two new dihydrochalcones, named erioschalcones A ( 1) and B ( 2), demonstrated significant inhibitory activity against the microbial strains Bacillus megaterium, Escherichia coli, Chlorella fusca and Microbotryum violaceum.

Two new triterpenoid saponins from rhizome of Anemone raddeana Regel.

PubMed

Fan, Li; Lu, Jincai; Wang, Jing; Cheng, Weiming; Yao, Yan; Liu, Runxiang; Zhang, Hongfen

2010-01-01

Two new 27-hydroxyoleanolic acid-type triterpenoid saponins, raddeanoside Ra (1) and raddeanoside Rb (2), were isolated from the rhizome of Anemone raddeana Regel. The structures of the two compounds were elucidated to be 27-hydroxyoleanolic acid 3-O-beta-D: -glucopyranosyl-(1 --> 4)-alpha-L: -arabinopyranoside (1) and 27-hydroxyoleanolic acid 3-O-alpha-L: -arabinopyranosyl-(1 --> 3)-alpha-L: -rhamnopyranosyl-(1 --> 2)-alpha- L: -arabinopyranoside (2) on the basis of chemical and spectral evidence.

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.

Chemical study of the fungus Psilocybe merdaria.

PubMed

Yang, Ning-Ning; Ma, Qing-Yun; Huang, Sheng-Zhuo; Kong, Fan-Dong; Dai, Hao-Fu; Yu, Zhi-Fang; Zhao, You-Xing

2017-04-01

Chemical investigation on the cultures of the fungus Psilocybe merdaria resulted in the first isolation of 10 compounds including two new ones 11,14-dihydroxylneoechinulin E (1) and (S)-4-(4-methylpent-3-en-1-yl)-butyrolactone (2). Their structures were elucidated from the analysis of 1D and 2D NMR and MS data. Among them, compound 7 showed inhibitory activity against AChE with 20% percentage at a concentration of 50 μg/ml.

Psiguadials A and B, two novel meroterpenoids with unusual skeletons from the leaves of Psidium guajava.

PubMed

Shao, Meng; Wang, Ying; Liu, Zhong; Zhang, Dong-Mei; Cao, Hui-Hui; Jiang, Ren-Wang; Fan, Chun-Lin; Zhang, Xiao-Qi; Chen, He-Ru; Yao, Xin-Sheng; Ye, Wen-Cai

2010-11-05

Psiguadials A (1) and B (2), two novel sesquiterpenoid-diphenylmethane meroterpenoids with unusual skeletons, along with a pair of known epimers, psidial A (3) and guajadial (4), were isolated from the leaves of Psidium guajava. Their structures with absolute configurations were elucidated by means of NMR, X-ray diffraction, and quantum chemical CD calculation. Compounds 1, 2, and 4 exhibited potent inhibitory effects on the growth of human hepatoma cells.

Guajavadimer A, a Dimeric Caryophyllene-Derived Meroterpenoid with a New Carbon Skeleton from the Leaves of Psidium guajava.

PubMed

Li, Chuang-Jun; Ma, Jie; Sun, Hua; Zhang, Dan; Zhang, Dong-Ming

2016-01-15

Guajavadimer A (1), a dimeric sesquiterpene-based meroterpenoid which possessed an unprecedented two caryophyllenes, a benzylphlorogulcinol, and a flavonone-fused complicated stereochemical skeleton, was isolated from the leaves of Psidium guajava L. Its structure and absolute configuration were elucidated on the basis of spectroscopic data and X-ray crystallography. Guajavadimer A (1) showed moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced toxicity in HepG2 cells.

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.

Corallocins A-C, Nerve Growth and Brain-Derived Neurotrophic Factor Inducing Metabolites from the Mushroom Hericium coralloides.

PubMed

Wittstein, Kathrin; Rascher, Monique; Rupcic, Zeljka; Löwen, Eduard; Winter, Barbara; Köster, Reinhard W; Stadler, Marc

2016-09-23

Three new natural products, corallocins A-C (1-3), along with two known compounds were isolated from the mushroom Hericium coralloides. Their benzofuranone and isoindolinone structures were elucidated by spectral methods. All corallocins induced nerve growth factor and/or brain-derived neurotrophic factor expression in human 1321N1 astrocytes. Furthermore, corallocin B showed antiproliferative activity against HUVEC and human cancer cell lines MCF-7 and KB-3-1.

Novel dihydro-beta-agarofuran sesquiterpenes as potent modulators of human P-glycoprotein dependent multidrug resistance.

PubMed

Torres-Romero, David; Muñoz-Martínez, Francisco; Jiménez, Ignacio A; Castanys, Santiago; Gamarro, Francisco; Bazzocchi, Isabel L

2009-12-21

P-Glycoprotein (Pgp) overexpression is one factor contributing to multidrug resistance (MDR) in cancer cells and represents one drawback in the treatment of cancer. In an attempt to find more specific and less toxic anticancer MDR-reversal agents, we report herein the isolation, structure elucidation and biological activity of nine new (, and ) and seven known (, and ) dihydro-beta-agarofuran sesquiterpenes from the leaves of Celastrus vulcanicola. Their stereostructures were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR techniques, CD studies and biogenetic means. All the compounds were assayed on human MDR1-transfected NIH-3T3 cells, in order to determine their ability to reverse the MDR phenotype due to Pgp overexpression. Six compounds from these series (, , , , and ) showed an effectiveness that was similar to (or higher than) the classical Pgp reversal agent verapamil for the reversal of resistance to daunomycin and vinblastine. The structure-activity relationships are discussed.

Purification and partial elucidation of the structure of an antioxidant carbohydrate biopolymer from the probiotic bacterium Bacillus coagulans RK-02.

PubMed

Kodali, Vidya P; Perali, Ramu S; Sen, R

2011-08-26

An exopolysaccharide (EPS) was isolated from Bacillus coagulans RK-02 and purified by size exclusion chromatography. The purified, homogeneous EPS had an average molecular weight of ∼3 × 10⁴ Da by comparison with FITC-labeled dextran standards. In vivo evaluations showed that, like other reported polysaccharides, this EPS displayed significant antioxidant activity. FTIR spectroscopy analysis showed the presence of hydroxy, carboxy, and α-glycosidic linkages and a mannose residue. GC analysis indicated that the EPS was a heteropolymer composed of glucose, mannose, galactose, glucosamine, and fucose as monomeric constituent units. Partial elucidation of the structure of the carbohydrate biopolymer based on GC-MS and NMR analysis showed the presence of two unique sets of tetrasaccharide repeating units that have 1→3 and 1→6 glycosidic linkages. This is also the first report of a Gram-positive bacterial polysaccharide with both fucose as a sugar monomer and 1→3 and 1→6 glycosidic linkages in the molecular backbone.

Structure determination of metabolites isolated from urine and bile after administration of AY4166, a novel D-phenylalanine-derivative hypoglycemic agent.

PubMed

Takesada, H; Matsuda, K; Ohtake, R; Mihara, R; Ono, I; Tanaka, K; Naito, M; Yatagai, M; Suzuki, E

1996-10-01

Molecular structures of 10 metabolites, which were isolated from urine (M1-M8) or bile (M9 and M10) after administration of AY4166 (N-(trans-4-isopropylcyclohexanecarbonyl)-D-phenylalanine), a novel amino acid derivative with hypoglycemic activity, have been elucidated by mass spectrometry and nuclear magnetic resonance. Four of these (M1, M2, M3 and M8) were determined to be hydroxyl derivatives of AY4166, two (M9 and M10) were carboxylate derivatives via oxidization of M2 and M3, three (M4, M5 and M6) were glucronic acid conjugates and the other (M7) was a dehydro derivative. The estimated structures for M1, M2, M3, M7, M8, M9 and M10 were confirmed by the coincidence of the retention time of HPLC, MS and 1H NMR spectra between the isolated metabolites and authentic synthesized substances. For three glucronic acid conjugates, M4, M5 and M6, structural confirmation was performed by a selective enzymatic digestion with beta-glucronidase. M1 and M2/3 were about 5-6 and 3 times less potent than AY4166, respectively, and M7 was almost as potent as AY4166.

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.

Tetrahydroxanthones from Mongolian medicinal plant Gentianella amarella ssp. acuta.

PubMed

Lu, Shuangxin; Tanaka, Naonobu; Kawazoe, Kazuyoshi; Murakami, Kotaro; Damdinjav, Davaadagva; Dorjbal, Enkhjargal; Kashiwada, Yoshiki

2016-10-01

Two tetrahydroxanthones, 1,3,5S,8S-tetrahydroxy-5,6,7,8-tetrahydroxanthone (1) and 1,3,5R,8S-tetrahydroxy-5,6,7,8-tetrahydroxanthone (2), and six new tetrahydroxanthone glycosides, amarellins A-F (3-8), were isolated from the aerial parts of a Mongolian medicinal plant Gentianella amarella ssp. acuta (Gentianaceae). The structures of 1-8 were elucidated on the basis of spectroscopic analysis, chemical conversion, and ECD calculation. Amarellins A-C (3-5) were assigned as 8-O-β-D-glucoside, 8-O-β-D-xyloside, and 1-O-β-D-glucoside of 1, respectively, while amarellins D-F (6-8) were elucidated to be 8-O-β-D-xyloside, 1-O-β-D-glucoside, and 3-O-β-D-glucoside of 2, respectively.

Gene flow contributes to diversification of the major fungal pathogen Candida albicans.

PubMed

Ropars, Jeanne; Maufrais, Corinne; Diogo, Dorothée; Marcet-Houben, Marina; Perin, Aurélie; Sertour, Natacha; Mosca, Kevin; Permal, Emmanuelle; Laval, Guillaume; Bouchier, Christiane; Ma, Laurence; Schwartz, Katja; Voelz, Kerstin; May, Robin C; Poulain, Julie; Battail, Christophe; Wincker, Patrick; Borman, Andrew M; Chowdhary, Anuradha; Fan, Shangrong; Kim, Soo Hyun; Le Pape, Patrice; Romeo, Orazio; Shin, Jong Hee; Gabaldon, Toni; Sherlock, Gavin; Bougnoux, Marie-Elisabeth; d'Enfert, Christophe

2018-06-08

Elucidating population structure and levels of genetic diversity and recombination is necessary to understand the evolution and adaptation of species. Candida albicans is the second most frequent agent of human fungal infections worldwide, causing high-mortality rates. Here we present the genomic sequences of 182 C. albicans isolates collected worldwide, including commensal isolates, as well as ones responsible for superficial and invasive infections, constituting the largest dataset to date for this major fungal pathogen. Although, C. albicans shows a predominantly clonal population structure, we find evidence of gene flow between previously known and newly identified genetic clusters, supporting the occurrence of (para)sexuality in nature. A highly clonal lineage, which experimentally shows reduced fitness, has undergone pseudogenization in genes required for virulence and morphogenesis, which may explain its niche restriction. Candida albicans thus takes advantage of both clonality and gene flow to diversify.

Neopetrosiquinones A and B, sesquiterpene benzoquinones isolated from the deep-water sponge Neopetrosia cf. proxima.

PubMed

Winder, Priscilla L; Baker, Heather L; Linley, Patricia; Guzmán, Esther A; Pomponi, Shirley A; Diaz, M Cristina; Reed, John K; Wright, Amy E

2011-11-15

Two new marine-derived sesquiterpene benzoquinones which we designate as neopetrosiquinones A (1) and B (2), have been isolated from a deep-water sponge of the family Petrosiidae. The structures were elucidated on the basis of their spectroscopic data. Compounds 1 and 2 inhibit the in vitro proliferation of the DLD-1 human colorectal adenocarcinoma cell line with IC(50) values of 3.7 and 9.8 μM, respectively, and the PANC-1 human pancreatic carcinoma cell line with IC(50) values of 6.1 and 13.8 μM, respectively. Neopetrosiquinone A (1) also inhibited the in vitro proliferation of the AsPC-1 human pancreatic carcinoma cell line with an IC(50) value of 6.1 μM. The compounds are structurally related to alisiaquinone A, cyclozonarone, and xestoquinone. Copyright © 2011 Elsevier Ltd. All rights reserved.

Damxungmacin A and B, Two New Amicoumacins with Rare Heterocyclic Cores Isolated from Bacillus subtilis XZ-7.

PubMed

Tang, Hui-Ling; Sun, Cheng-Hang; Hu, Xin-Xin; You, Xue-Fu; Wang, Min; Liu, Shao-Wei

2016-11-23

Two new amicoumacins, named Damxungmacin A ( 1 ) and B ( 2 ), were isolated from the culture broth of a soil-derived bacterium Bacillus subtilis XZ-7. Their chemical structures were elucidated by spectroscopic studies (UV, IR, NMR and HR-ESI-MS). Compound 1 possessed a 1,4-diazabicyclo[2.2.1]heptane-2-one ring system in its structure, which was reported for the first time, while 2 had a 1-acetylmorpholine-3-one moiety, which was naturally rare. Compound 1 exhibited moderate to weak cytotoxic activities against three human tumor cell lines (A549, HCT116 and HepG2) with IC 50 values of 13.33, 14.34 and 13.64 μM, respectively. Meanwhile, compound 1 showed weak antibacterial activities against some strains of Staphylococcus epidermidis , while compound 2 at 16 μg/mL did not show antibacterial activity.

Upregulation of CD4+ T-Lymphocytes by Isomeric Mixture of Quercetin-3-O-Rutinoside and Quercetin-3-O-Robinobioside Isolated from Millettia aboensis.

PubMed

Ajaghaku, Daniel Lotanna; Akah, Peter Achunike; Ilodigwe, Emmanuel Emeka; Nduka, Sunday Odunke; Osonwa, Uduma Eke; Okoye, Festus Basden Chinedu

2018-05-01

Millettia aboensis (Hook. F.) Baker (Fabaceae) is popular in ethnomedicine for its acclaimed efficacy in a number of disease conditions. This study evaluated the immunomodulatory effect of the leaf extract as a possible mechanism of its ethnomedicinal uses. Humoral and cellular immune responses of Balb/c mice to tetanus toxoid and cyclophosphamide, respectively, were used to monitor immunomodulatory activities of the ethanol leaf extract and fractions of M. aboensis at 200, 300 and 400 mg/kg. Active (butanol) fraction of the extract was subjected to chromatographic purifications to isolate the active compound and the structure elucidated by a combination of 1D and 2D NMR and mass spectrometry. Stimulation of specific T-lymphocytes using intracellular cytokine staining technique was used to evaluate immune-enhancing activity of the isolated compound. The extract and fractions evoked increase in both humoral and cellular immunity. At 400 mg/kg of butanol fraction, the normalized mean secondary production of IgG1 and IgG2a antibodies were 9.0 and 7.7, respectively. Serum cytokine production by butanol fraction following secondary challenge with tetanus toxoid showed that IL-12, IL-17A and IFN-γ were expressed by 48.14, 41.37 and 38.22%, respectively. Structural elucidation of the active compound revealed presence of isomeric mixtures of quercetin-3-O-rutinoside and quercetin-3-O-robinobioside (Compound 1a/b). Compound 1a/b exhibited in vitro upregulation of specific CD4 + T-lymphocytes that were largely IFNγ releasing with up to 43.7% stimulation at 6.25 μg/mL compared to the baseline effect in DMSO vehicle control group. M. aboensis expressed strong immune-enhancing properties, which may explain its ethnopharmacological use in disease management.

Ophiamides A-B, new potent urease inhibitory sphingolipids from Heliotropium ophioglossum.

PubMed

Firdous, Sadiqa; Ansari, Nida Hassan; Fatima, Itrat; Malik, Abdul; Afza, Nighat; Iqbal, Lubna; Lateef, Mehreen

2012-07-01

Ophiamides A (1) and B (2), two new sphingolipids have been isolated from the n-hexane subfraction of the MeOH extract of the whole plant of Heliotropium ophioglossum along with glycerol monopalmitate (3) and β-sitosterol 3-O-β-D: -glucoside (4) reported for the first time from this species. Their structures were elucidated by spectroscopic techniques including MS and 2D-NMR spectroscopy. Both the compounds 1 and 2 showed potent inhibitory activity against the enzyme urease.

[Chemical constituents from leaves of Paulownia fortunei].

PubMed

Li, Xiao-Qiang; Wu, Jing-Lian; Cao, Fei-Hua; Li, Chong

2008-06-01

To study the chemical constituents of leaves of Paulownia fortunei (Seem.) Hemsl. The constituents were isolated by column chromatography and their structures were elucidated through spectroscopic analysis. The compounds were identified as mimulone (I), apigenin (II), luteolin (III), 2alpha, 3beta, 19beta-trihydroxyurs-28-O-beta-D-galactonopyranos ylester (anserinoside, IV), 3alpha-hydroxyl-ursolicacid (V), ursolicacid (VI), daucosterol (VII), beta-sitosterol (VIII). The compounds I - V are obtained from leaves of Paulownia fortunei (Seem.) Hemsl for the first time.

[Studies on the chemical constituents from the roots of Kalopanax septemlobus].

PubMed

Yao, Huan-Kai; Duan, Jing-Yu; Li, Yan; Wang, Jian-Hui; Yin, Xiao-Xing; Duan, Hong-Quan

2011-05-01

To investigate the chemical constituents of Kalopanax septemlobus. Chromatographic techniques including silica gel, gel, semi-preparative HPLC and PTLC as well as recrystallization were employed in the isolation and purification, and the structures were elucidated by spectral analysis and physical and chemical properties. 6 compounds were identified as liriodendrin (1), (-) -syringarenol (2), trans-coniferyl aldehyde (3), trans-caffeic acid (4), beta-daucosterol (5), beta-sitosterol (6). Compounds 2 -5 are obtained from this genus for the first time.

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).

Microsporols A-C from the Plant Endophytic Fungus Pestalotiopsis microspore.

PubMed

Wu, Xianfu; Wang, Yadan; Liu, Shuchun; Liu, Xinzhong; Guo, Liangdong

2015-10-01

Three new ambuic acid derivatives, microsporols A-C (1-3) and the known compound ambuic acid (4), were isolated from the solid-substrate fermentation cultures of the plant endophytic fungus Pestalotiopsis microspora. Their structures were elucidated primarily by NMR experiments. The absolute configurations of the 6,7-diol moiety in 1 and 2 were assigned using the Snatzke's method, whereas that of 3 was deduced by circular dichroism (CD) exciton chirality method. Compounds 1, 3, and 4 showed moderate 5-lipoxygenase (5-LOX) inhibitory effects.

Bioactive steroidal sulfates from the ambulakrums of the Pacific starfish Lysastrosoma anthosticta.

PubMed

Levina, Eleonora V; Kalinovsky, Anatoly I; Dmitrenok, Pavel S; Aminin, Dmitry L

2009-08-01

Lysaketotriol (1) and lysaketodiol (2), along with two previously known polyhydroxylated steroidal sulfates (3, 4), were isolated from the ethanolic extract of ambulakrums separated from the arms of the starfish Lysastrosoma anthosticta (Sea of Japan). The chemical structures have been elucidated using 1D and 2D NMR spectroscopy (1H, 13C, DEPT, COSY-45, HSQC and HMBC) and mass spectrometry. Compound 1 produced moderate stimulation of lysosomal activity in mouse splenocytes and compounds 1-2 showed immunomodulatory activity.

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

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.

Three New Cytotoxic Withanolides from the Chinese Folk Medicine Physalis angulata.

PubMed

Gao, Cai-Yun; Ma, Ting; Luo, Jun; Kong, Ling-Yi

2015-12-01

Physagulides M-O, three new withanolides (1-3), were isolated from the aerial parts of Physalis angulata L. Their structures were elucidated through extensive spectroscopic techniques, including 1D and 2D NMR, and HRESIMS. The absolute configurations (22-R) of these new compounds were determined by CD analysis. Compounds 1 and 3 showed significant selective cytotoxic activities on the MG-63 cell line, with IC50 values of 4.28 and 5.44 μM, respectively.

Two new steroidal saponins from Tribulus terrestris L.

PubMed

Liu, Tao; Lu, Xuan; Wu, Biao; Chen, Gang; Hua, Hui-Ming; Pei, Yue-Hu

2010-01-01

Two new steroidal saponins were isolated from the fruits of Tribulus terrestris L. Their structures were elucidated by spectroscopic and chemical analysis as (23S,24R,25R)-5alpha-spirostane-3beta,23,24-triol-3-O-{alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 4)]-beta-D-galactopyranoside} (1) and (23S,24R,25S)-5alpha-spirostane-3beta,23,24-triol-3-O-{alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 4)]-beta-D-galactopyranoside} (2).

Haenamindole, an unusual diketopiperazine derivative from a marine-derived Penicillium sp. KCB12F005.

PubMed

Kim, Jong Won; Ko, Sung-Kyun; Son, Sangkeun; Shin, Kee-Sun; Ryoo, In-Ja; Hong, Young-Soo; Oh, Hyuncheol; Hwang, Bang Yeon; Hirota, Hiroshi; Takahashi, Shunji; Kim, Bo Yeon; Osada, Hiroyuki; Jang, Jae-Hyuk; Ahn, Jong Seog

2015-11-15

During the chemical investigation of marine-derived fungus, an unusual diketopiperazine (DKP) alkaloid, haenamindole (1), was isolated from a culture of the marine-derived fungus Penicillium sp. KCB12F005. The structure of 1, which possesses benzyl-hydroxypiperazindione and phenyl-pyrimidoindole rings system in the molecule, was elucidated by analysis of NMR and MS data. The stereochemistry of 1 was determined by ROESY and advanced Marfey's method. Copyright © 2015 Elsevier Ltd. All rights reserved.

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.

Polyketides with Immunosuppressive Activities from Mangrove Endophytic Fungus Penicillium sp. ZJ-SY₂.

PubMed

Liu, Hongju; Chen, Senhua; Liu, Weiyang; Liu, Yayue; Huang, Xishan; She, Zhigang

2016-11-25

Nine polyketides, including two new benzophenone derivatives, peniphenone ( 1 ) and methyl peniphenone ( 2 ), along with seven known xanthones ( 3 - 9 ) were obtained from mangrove endophytic fungus Penicillium sp. ZJ-SY₂ isolated from the leaves of Sonneratia apetala . Their structures were elucidated on the basis of MS, 1D, and 2D NMR data. Compounds 1 , 3 , 5 , and 7 showed potent immunosuppressive activity with IC 50 values ranging from 5.9 to 9.3 μg/mL.

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.

Three new Anthraquinones, one new Benzochromene and one new Furfural glycoside from Lasianthus acuminatissimus.

PubMed

Huang, Teng; Ming, Jianxin; Zhong, Jialiang; Zhong, Youquan; Wu, Huaqiang; Liu, Hongdong; Li, Bin

2018-06-01

Three new anthraquinones, lasianthurin B (1), C (2), lasianthuoside D (3), a new benzochromene, lasianthurin D (4), and a new furfural glycoside, lasianthuoside E (5), together with one known compound 4- hydroxymethyl-2-furaldehyde (6) were isolated from an alcohol extract of the root of Lasianthus acuminatissimus. Their structures were elucidated on the basis of extensive spectroscopic data analysis (including 1D, 2D NMR, X-ray, and MS experiments) and comparsion to literature data.

(+/-)-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.

Capgermacrenes A and B, Bioactive Secondary Metabolites from a Bornean Soft Coral, Capnella sp.

PubMed Central

Phan, Chin-Soon; Ng, Shean-Yeaw; Kim, Eun-A; Jeon, You-Jin; Palaniveloo, Kishneth; Santhanaraju Vairappan, Charles

2015-01-01

Two new bicyclogermacrenes, capgermacrenes A (1) and B (2), were isolated with two known compounds, palustrol (3) and litseagermacrane (4), from a population of Bornean soft coral Capnella sp. The structures of these metabolites were elucidated based on spectroscopic data. Compound 1 was found to inhibit the accumulation of the LPS-induced pro-inflammatory IL-1β and NO production by down-regulating the expression of iNOS protein in RAW 264.7 macrophages. PMID:25996100

Antitumor Compounds from the Stout Camphor Mushroom Taiwanofungus camphoratus (Higher Basidiomycetes) Spent Culture Broth.

PubMed

Jia, Wei; Bai, Yan-Yan; Zhang, Zhong; Feng, Na; Feng, Jie; Yan, Meng-Qiu; Zhu, Li-Na; Jia, Xin-Cheng; Wang, Ming-Dao; Zhang, Jing-song; Fan, Hua

2015-01-01

A known compound, 5-(hydroxymethyl) furan-2-carbaldehyde, and a novel compound, 3-isobutyl-1-methoxy-4-(4'-(3-methylbut-2-enyloxy)phenyl)-1H-pyrrole-2,5-dione were isolated from spent broth from submerged cultures of Taiwanofungus camphoratus. Their structures were elucidated by nuclear magnetic resonance (1H, 13C, and 2D) and mass spectra. These compounds inhibited the proliferation of K562 and HepG2 tumor cells in vitro.

New alkaloids of the sarpagine group from Rauvolfia serpentina hairy root culture.

PubMed

Sheludko, Yuri; Gerasimenko, Irina; Kolshorn, Heinz; Stöckigt, Joachim

2002-07-01

Three new monoterpenoid indole alkaloids, 19(S),20(R)-dihydroperaksine (1), 19(S),20(R)-dihydroperaksine-17-al (2), and 10-hydroxy-19(S),20(R)-dihydroperaksine (3), along with 16 known alkaloids 4-19 were isolated from hairy root culture of Rauvolfia serpentina, and their structures were elucidated by 1D and 2D NMR analyses. Taking into account the stereochemistry of the new alkaloids and results of preliminary enzymatical studies, the putative biosynthetical relationships between the novel alkaloids are discussed.

27-Hydroxyoleanolic acid type triterpenoid saponins from Anemone raddeana rhizome.

PubMed

Fan, Li; Lu, Jin-Cai; Xue, Jiao; Gao, Song; Xu, Bei-Bei; Cao, Bai-Yi; Zhang, Jing-Jing

2010-02-01

Two new 27-hydroxyoleanolic acid type triterpenoid saponins were isolated from the rhizomes of Anemone raddeana Regel. The structures of the two compounds were elucidated as 27-hydroxyoleanolic acid 3-O-beta-D-glucopyranosyl (1 --> 2)-alpha-L-arabinopyranoside (1) and 3-O-alpha-L-rhamnopyranosyl (1 --> 2)[beta-D-glucopyranosyl (1 --> 4)]-alpha-L-arabinopyranosyl-27-hydroxyoleanolic acid 28-O-alpha-L-rhamnopyranosyl (1 --> 4)-beta-D-glucopyranosyl (1 --> 6)-beta-D-glucopyranoside (2) on the basis of chemical and spectral evidence.

(+)- and (-)-Cajanusine, a pair of new enantiomeric stilbene dimers with a new skeleton from the leaves of Cajanus cajan.

PubMed

Li, Xiao-Long; Zhao, Bing-Xin; Huang, Xiao-Jun; Zhang, Dong-Mei; Jiang, Ren-Wang; Li, Ying-Jie; Jian, Yu-Qing; Wang, Ying; Li, Yao-Lan; Ye, Wen-Cai

2014-01-03

A pair of new enantiomeric stilbene dimers, (+)- and (-)-cajanusine [(+)-1 and (-)-1], with a unique coupling pattern were isolated from the leaves of Cajanus cajan . Their structures including absolute configurations were elucidated on the basis of comprehensive spectroscopic and single-crystal X-ray diffraction analyses, as well as CD calculations. The plausible biogenetic pathway of 1 was also proposed. Additionally, (±)-1, (+)-1, and (-)-1 exhibited inhibitory activities on the growth of human hepatocellular carcinoma cells.

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.

Quinolizidine alkaloids from Lupinus lanatus

NASA Astrophysics Data System (ADS)

Neto, Alexandre T.; Oliveira, Carolina Q.; Ilha, Vinicius; Pedroso, Marcelo; Burrow, Robert A.; Dalcol, Ionara I.; Morel, Ademir F.

2011-10-01

In this study, one new quinolizidine alkaloid, lanatine A ( 1), together with three other known alkaloids, 13-α- trans-cinnamoyloxylupanine ( 2), 13-α-hydroxylupanine ( 3), and (-)-multiflorine ( 4) were isolated from the aerial parts of Lupinus lanatus (Fabaceae). The structures of alkaloids 1- 4 were elucidated by spectroscopic data analysis. The stereochemistry of 1 was determined by single crystal X-ray analysis. Bayesian statistical analysis of the Bijvoet differences suggests the absolute stereochemistry of 1. In addition, the antimicrobial potential of alkaloids 1- 4 is also reported.

Neosordarin and hydroxysordarin, two new antifungal agents from Sordaria araneosa.

PubMed

Davoli, Paolo; Engel, Günther; Werle, Andreas; Sterner, Olov; Anke, Timm

2002-04-01

Two novel antifungal agents belonging to the sordarin family have been isolated from fermentations of Sordaria araneosa by bioassay-guided purification and their structures elucidated by NMR techniques. Neosordarin (1) is closely related to the recently discovered hypoxysordarin (2), with only small differences on the aliphatic side chain acylating the hydroxyl in the 3'-position of the sordarose moiety. Hydroxysordarin (3) closely resembles sordarin (4), the only slight difference being the replacement of sordarose with altrose as the sugar unit.

Medicinal flowers. XXXVI.1) Acylated oleanane-type triterpene saponins with inhibitory effects on melanogenesis from the flower buds of Chinese Camellia japonica.

PubMed

Nakamura, Seikou; Fujimoto, Katsuyoshi; Nakashima, Souichi; Matsumoto, Takahiro; Miura, Tomoko; Uno, Kaoru; Matsuda, Hisashi; Yoshikawa, Masayuki

2012-01-01

Four acylated oleanane-type triterpene oligoglycosides, sanchakasaponins E-H, were isolated from the flower buds of Camellia japonica cultivated in Yunnan province, China, together with four known triterpene oligoglycosides. The chemical structures of the new triterpene oligoglycosides were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of the triterpene oligoglycoside constituents on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells were investigated.

Isopalhinine A, a unique pentacyclic Lycopodium alkaloid from Palhinhaea cernua.

PubMed

Dong, Liao-Bin; Gao, Xiu; Liu, Fei; He, Juan; Wu, Xing-De; Li, Yan; Zhao, Qin-Shi

2013-07-19

A new pentacyclic (5/6/6/6/7) Lycopodium alkaloid named isopalhinine A (1), which possesses a sterically congested architecture built with a tricyclo[4.3.1.0(3,7)]decane (isotwistane) moiety and a 1-azabicyclo[4.3.1]decane moiety, and palhinines B (2) and C (3) were isolated from Palhinhaea cernua. The structure and absolute configuration of 1 were elucidated by a combination of NMR spectra, optical rotation calculation, and X-ray diffraction experiment. A possible biogenetic pathway was also proposed.

Vanillic acid derivatives from the green algae Cladophora socialis as potent protein tyrosine phosphatase 1B inhibitors.

PubMed

Feng, Yunjiang; Carroll, Anthony R; Addepalli, Rama; Fechner, Gregory A; Avery, Vicky M; Quinn, Ronald J

2007-11-01

A novel vanillic acid derivative (1) and its sulfate adduct (2) were isolated from a green algae, Cladophora socialis. The structures of 1 and 2 were elucidated from NMR and HRESIMS experiments. Both compounds showed potent inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), an enzyme involved in the regulation of insulin cell signaling. Compounds 1 and 2 had IC50 values of 3.7 and 1.7 microM, respectively.

Volvalerelactones A and B, two new sesquiterpenoid lactones with an unprecedented skeleton from Valeriana officinalis var. latifolia.

PubMed

Wang, Peng-Cheng; Ran, Xin-Hui; Luo, Huai-Rong; Hu, Jiang-Miao; Chen, Rui; Ma, Qing-Yun; Dai, Hao-Fu; Liu, Yu-Qing; Xie, Ming-Jin; Zhou, Jun; Zhao, You-Xing

2011-06-17

Volvalerelactones A and B (1 and 2), two new sesquiterpenoid lactones with an unprecedented 3/7/6 tricyclic ring system, were isolated from the roots of Valeriana officinalis var. latifolia. Their structures and relative configurations were elucidated by spectroscopic data and single-crystal X-ray diffraction crystallography, and the absolute configuration was assigned by computational methods. The possible biosynthetic pathways of 1 and 2 were also proposed. © 2011 American Chemical Society

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.

Purpurediolin and purpurenin, two new cytotoxic adjacent bis-tetrahydrofuran annonaceous acetogenins from the seeds of Annona purpurea.

PubMed

Chávez, D; Mata, R

1998-05-01

Two novel cytotoxic acetogenins, purpurediolin (1) and purpurenin (2), were isolated from the seeds of Annona purpurea. Their structures were elucidated by a combination of chemical and spectral methods including MS and NMR measurements. In addition, six known acetogenins were obtained, namely, bullatacin, squamocin (annonin I), motrilin (squamocin C), annoglaucin, xylomatenin, and annonacin A. Compounds 1 and 2 exhibited potent cytotoxic activity in vitro against six human solid tumor cell lines.

Lactone Derivatives Produced by a Phaeoacremonium sp., an Endophytic Fungus from Senna spectabilis.

PubMed

Silva, Geraldo H; Zeraik, Maria L; de Oliveira, Camila M; Teles, Helder L; Trevisan, Henrique C; Pfenning, Ludwig H; Nicolli, Camila P; Young, Maria C M; Mascarenhas, Yvonne P; Abreu, Lucas M; Saraiva, Amanda C; Medeiros, Alexandra I; Bolzani, Vanderlan da S; Araujo, Angela R

2017-05-26

Three new isoaigialones, A, B, and C (1-3), along with aigialone (4), were isolated from the crude EtOAc extract of a Phaeoacremonium sp., an endophytic fungus obtained from the leaves of Senna spectabilis. The structures of these compounds were elucidated based on the analysis of spectroscopic data. Compounds 2 and 4 were active against the phytopathogenic fungi Cladosporium cladosporioides and C. sphaerospermum. This is the first report of metabolites produced by an Phaeoacremonium sp., associated with S. spectabilis.

Erinacine S, a Rare Sesterterpene from the Mycelia of Hericium erinaceus.

PubMed

Chen, Chien-Chih; Tzeng, Tsai-Teng; Chen, Chin-Chu; Ni, Ching-Li; Lee, Li-Ya; Chen, Wan-Ping; Shiao, Young-Ji; Shen, Chien-Chang

2016-02-26

A new sesterterpene, erinacine S, and one cyathane diterpene xyloside, erinacine A, were isolated from the ethanol extract of the mycelia of Hericium erinaceus. Their structures were elucidated by spectroscopic and X-ray analysis. A 30-day oral course of erinacines A and S attenuated Aβ plaque burden in the brains of 5-month-old female APP/PS1 transgenic mice. Moreover, erinacines A and S significantly increased the level of insulin-degrading enzyme in cerebral cortex.

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.

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.

Bridging the gap between modules in isolation and as part of networks: A systems framework for elucidating interaction and regulation of signalling modules

NASA Astrophysics Data System (ADS)

Menon, Govind; Krishnan, J.

2016-07-01

While signalling and biochemical modules have been the focus of numerous studies, they are typically studied in isolation, with no examination of the effects of the ambient network. In this paper we formulate and develop a systems framework, rooted in dynamical systems, to understand such effects, by studying the interaction of signalling modules. The modules we consider are (i) basic covalent modification, (ii) monostable switches, (iii) bistable switches, (iv) adaptive modules, and (v) oscillatory modules. We systematically examine the interaction of these modules by analyzing (a) sequential interaction without shared components, (b) sequential interaction with shared components, and (c) oblique interactions. Our studies reveal that the behaviour of a module in isolation may be substantially different from that in a network, and explicitly demonstrate how the behaviour of a given module, the characteristics of the ambient network, and the possibility of shared components can result in new effects. Our global approach illuminates different aspects of the structure and functioning of modules, revealing the importance of dynamical characteristics as well as biochemical features; this provides a methodological platform for investigating the complexity of natural modules shaped by evolution, elucidating the effects of ambient networks on a module in multiple cellular contexts, and highlighting the capabilities and constraints for engineering robust synthetic modules. Overall, such a systems framework provides a platform for bridging the gap between non-linear information processing modules, in isolation and as parts of networks, and a basis for understanding new aspects of natural and engineered cellular networks.

Bridging the gap between modules in isolation and as part of networks: A systems framework for elucidating interaction and regulation of signalling modules.

PubMed

Menon, Govind; Krishnan, J

2016-07-21

While signalling and biochemical modules have been the focus of numerous studies, they are typically studied in isolation, with no examination of the effects of the ambient network. In this paper we formulate and develop a systems framework, rooted in dynamical systems, to understand such effects, by studying the interaction of signalling modules. The modules we consider are (i) basic covalent modification, (ii) monostable switches, (iii) bistable switches, (iv) adaptive modules, and (v) oscillatory modules. We systematically examine the interaction of these modules by analyzing (a) sequential interaction without shared components, (b) sequential interaction with shared components, and (c) oblique interactions. Our studies reveal that the behaviour of a module in isolation may be substantially different from that in a network, and explicitly demonstrate how the behaviour of a given module, the characteristics of the ambient network, and the possibility of shared components can result in new effects. Our global approach illuminates different aspects of the structure and functioning of modules, revealing the importance of dynamical characteristics as well as biochemical features; this provides a methodological platform for investigating the complexity of natural modules shaped by evolution, elucidating the effects of ambient networks on a module in multiple cellular contexts, and highlighting the capabilities and constraints for engineering robust synthetic modules. Overall, such a systems framework provides a platform for bridging the gap between non-linear information processing modules, in isolation and as parts of networks, and a basis for understanding new aspects of natural and engineered cellular networks.

[Study on anti-tumor chemical constituents from pericarps of Juglans mandshurica].

PubMed

Zhou, Yuan-yuan; Meng, Ying; Jiang, Yan-qiu; Liu, Zhao-xi; Yang, Bing-you

2014-11-01

To study the anti-tumor chemical components of the pericarps of Juglans mandshurica. The chemical constituents were isolated and purified by AB-8 macroporous adsorption resin, silica gel, Sephadex LH-20 columns and recrystallization. The structures were elucidated on the basis of physicochemical properties and NMR spectral data analysis. From the pericarps of Juglans mandshurica, twelve compounds were separated and identified as 3-methoxy juglone(1), 3-ethoxy juglone(2), 1,8-di-hydroxy anthraquinone (3), juglone (4), 2α, 3α, 19α-trihydroxy ursolic acid (5), 1α, 3β-dihydroxy-olean-18-ene (6), methyl gallate (7), pterocarine(8), quercetin(9), kaempferol(10), daucosterol(11), and β-sitosterol(12). Compounds 1 - 3 and 6 are isolated from the pericarps of Juglans mandshurica for the first time. Compounds 5 and 7 are isolated from Juglans genus for the first time.

A new cytotoxic sesquiterpene quinone produced by Penicillium sp. F00120 isolated from a deep sea sediment sample.

PubMed

Lin, Xiuping; Zhou, Xuefeng; Wang, Fazuo; Liu, Kaisheng; Yang, Bin; Yang, Xianwen; Peng, Yan; Liu, Juan; Ren, Zhe; Liu, Yonghong

2012-01-01

A new fungal strain, displaying strong toxic activity against brine shrimp larvae, was isolated from a deep sea sediment sample collected at a depth of 1300 m. The strain, designated as F00120, was identified as a member of the genus Penicillium on the basis of morphology and ITS sequence analysis. One new sesquiterpene quinone, named penicilliumin A (1), along with two known compounds ergosterol (2) and ergosterol peroxide (3), were isolated and purified from the cultures of F00120 by silica gel column, Sephadex LH-20 column, and preparative thin layer chromatography. Their structures were elucidated by detailed nuclear magnetic resonance (NMR) and mass spectroscopic (MS) analysis as well as comparison with literature data. The new compound penicilliumin A inhibited in vitro proliferation of mouse melanoma (B16), human melanoma (A375), and human cervical carcinoma (Hela) cell lines moderately.

Secondary metabolites from endemic species Iris adriatica Trinajstić ex Mitić (Iridaceae).

PubMed

Bukvički, Danka; Novaković, Miroslav; Ab Ghani, Nurunajah; Marin, Petar D; Asakawa, Yoshinori

2018-08-01

This manuscript describes the first detailed chemical investigation of endemic species Iris adriatica, including isolation and structure elucidation. Chemical analyses of the rhizome CH 2 Cl 2 /MeOH (2:1) extract revealed fourteen secondary metabolites, mainly isoflavonoids. Among isoflavonoids, two groups have been found: nigricin-type and tectorigenin-type. Dominant group of the isolated compounds has been nigricin-type isoflavones: nigricin, nigricin-4'-(1-O-β-D-glucopyranoside) and nigricin-4'-(1-O-β-D-glucopyranosyl (1-6)-β-D-glucopyranoside) with 2.5, 10 and 1% of the total extract, respectively. Irisxanthone - xanthone C-glucoside, β-sitosterol, benzophenone and one of its derivatives have also been found. Nigricin-type isoflavonoids and irisxanthone can be considered as possible chemotaxonomic markers for I. adriatica. 5,3',5'-Trimethoxy-6,7-methylenedioxyisoflavone-4'-(1-O-β-D-glucopyranoside) and benzophenone have been isolated from Iris species for the first time.

A cytotoxic and apoptosis-inducing sesquiterpenoid isolated from the aerial parts of Artemisia princeps PAMPANINI (Sajabalssuk).

PubMed

Bang, Myun-Ho; Han, Min-Woo; Song, Myoung-Chong; Cho, Jin-Gyeong; Chung, Hae-Gon; Jeong, Tae-Sook; Lee, Kyung-Tae; Choi, Myung-Sook; Kim, Se-Young; Baek, Nam-In

2008-08-01

Repeated silica gel and octadecyl silica gel (ODS) column chromatography of the aerial parts of Artemisia princeps PAMPANINI (Sajabalssuk) led to the isolation of a new sesquiterpenoid, 3-((S)-2-methylbutyryloxy)-costu-1(10),4(5)-dien-12,6 alpha-olide (2), along with two previously reported sesquiterpenoids: 8 alpha-angeloyloxy-3beta,4 beta-epoxy-6 beta H,7 alpha H,8 beta H-guaia-1(10),11(13)-dien-12,6 alpha-olide (1, carlaolide B) and 3beta,4 beta-epoxy-8 alpha-isobutyryloxy-6 beta H,7 alpha H,8 beta H-guaia-1(10),11(13)-dien-12,6 alpha-olide (3, carlaolide A). The structure of compound 2 was elucidated by spectroscopic data analysis, including one dimensional (1D) and two dimensional (2D) nuclear magnetic resonance (NMR) experiments. Of the isolates, compound 2 exhibited potent cytotoxicity against human cervix adenocarcinoma cells and induced apoptosis.

New zwitterionic monoterpene indole alkaloids from Uncaria rhynchophylla.

PubMed

Guo, Qiang; Yang, Hongshuai; Liu, Xinyu; Si, Xiali; Liang, Hong; Tu, Pengfei; Zhang, Qingying

2018-01-31

Four new zwitterionic monoterpene indole alkaloids, rhynchophyllioniums A-D (1-4), together with eight known alkaloids (5-12), were isolated from the hook-bearing stems of Uncaria rhynchophylla. Their structures were elucidated by extensive spectroscopic data analysis of MS, 1D and 2D NMR, and ECD, and the zwitterionic forms and absolute configurations of 1 and 2 were unambiguously confirmed by single crystal X-ray diffraction analysis. All the isolates, including the monoterpene indole alkaloids with free C-22 carboxyl group and those with C-22 carboxyl methyl ester, were proved to be naturally coexisting in the herb by LC-MS analysis. This is the first report of monoterpene indole alkaloids that exist in the form of zwitterion. Additionally, the cytotoxic activities of all isolates against A549, HepG2, and MCF-7 cell lines are reported. Copyright © 2018 Elsevier B.V. All rights reserved.