Drimane sesquiterpenoids from the Aspergillus oryzae QXPC-4.

PubMed

Ren, Ren; Chen, Chao-Jun; Hu, Sha-Sha; Ge, Hui-Ming; Zhu, Wen-Yong; Tan, Ren-Xiang; Jiao, Rui-Hua

2015-03-01

Three new drimane sesquiterpenoids, astellolides C-E (1-3, resp.), four new drimane sesquiterpenoid p-hydroxybenzoates, astellolides F-I (4-7, resp.), together with two known compounds astellolides A and B (8 and 9, resp.), have been isolated from the liquid culture of Aspergillus oryzae (strain No. QXPC-4). Their structures were established by comprehensive analysis of spectroscopic data. The relative and absolute configurations were determined on the basis of NOESY and CD data, together with single-crystal X-ray diffraction analyses of compounds 1-3. The metabolites were evaluated for their cytotoxic activities, however, no compounds showed a significant cytotoxicity against the tested cell lines at a concentration of 20 μM. Copyright © 2015 Verlag Helvetica Chimica Acta AG, Zürich.

New Eudesmane-Type Sesquiterpenoids from the Mangrove-Derived Endophytic Fungus Penicillium sp. J-54.

PubMed

Qiu, Liuming; Wang, Pei; Liao, Ge; Zeng, Yanbo; Cai, Caihong; Kong, Fandong; Guo, Zhikai; Proksch, Peter; Dai, Haofu; Mei, Wenli

2018-03-28

Four new eudesmane-type sesquiterpenoids, penicieudesmol A-D ( 1 - 4 ), were isolated from the fermentation broth of the mangrove-derived endophytic fungus Penicillium sp. J-54. Their structures were determined by spectroscopic methods, the in situ dimolybdenum CD method, and modified Mosher's method. The bioassays results showed that 2 exhibited weak cytotoxicity against K-562 cells.

Pyrenophoric acid, a phytotoxic sesquiterpenoid penta-2,4-dienoic acid produced by a potential mycoherbicide, Pyrenophora semeniperda

Treesearch

Marco Masi; Susan Meyer; Alessio Cimmino; Anna Andolfi; Antonio Evidente

2014-01-01

A new phytotoxic sesquiterpenoid penta-2,4- dienoic acid, named pyrenophoric acid, was isolated from solid wheat seed culture of Pyrenophora semeniperda, a fungal pathogen proposed as a mycoherbicide for biocontrol of cheatgrass (Bromus tectorum) and other annual bromes. These bromes are serious weeds in winter cereals and also on temperate semiarid rangelands....

[Sesquiterpenoids of Coniogramme maxima].

PubMed

Chen, Yunfei; Liu, Shoujin; Wang, Fei

2012-04-01

To study sesquiterpenoids of Coniogramme maxima. Chemical constituents were separated by chromatography and their structures were identified according to physicochemical property and spectrum data. Fifteen compounds were separated by chromatography technique. Their structures were determined by spectral data, including 10 sesquiterpenoids as (3S)-pteroside D (1), epi-pterosin L (2), pterosin D (3), onitin (4), pterosin Z (5), onitisin (6), onitisin-glucopyranoside (7), onitin-15-O-beta-D-glucopyranoside (8), (2S,3R)-pterosin-L-2'-O-beta-D-glucopyranoside (9) and (3R)-peterosin D-3-O-beta-D-glucopyranoside (10). The other compounds were uracil (11), 3,4-dihydroxybenzaldehyde (12), 5-hydroxymethyl-2-furancarboxaldehyde (13), beta-sitosterol (14) and daucosterol (15). The above 15 compounds are separated from C. maxima for the first time, including 9 compounds being first separated from genus Coniogramme.

New Eudesmane-Type Sesquiterpenoids from the Mangrove-Derived Endophytic Fungus Penicillium sp. J-54

PubMed Central

Qiu, Liuming; Wang, Pei; Liao, Ge; Zeng, Yanbo; Cai, Caihong; Kong, Fandong; Guo, Zhikai; Proksch, Peter; Dai, Haofu; Mei, Wenli

2018-01-01

Four new eudesmane-type sesquiterpenoids, penicieudesmol A–D (1–4), were isolated from the fermentation broth of the mangrove-derived endophytic fungus Penicillium sp. J-54. Their structures were determined by spectroscopic methods, the in situ dimolybdenum CD method, and modified Mosher’s method. The bioassays results showed that 2 exhibited weak cytotoxicity against K-562 cells. PMID:29597304

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.

Pestaloporonins: Caryophyllene-Derived Sesquiterpenoids from a Fungicolous Isolate of Pestalotiopsis sp.

PubMed

Hwang, In Hyun; Swenson, Dale C; Gloer, James B; Wicklow, Donald T

2015-09-04

Three new sesquiterpenoids (pestaloporonins A-C; 1-3) related to the caryophyllene-derived punctaporonins were isolated from cultures of a fungicolous isolate of Pestalotiopsis sp. The structures of 1-3 were determined by analysis of NMR and HRMS data, and the structure of 1, including its absolute configuration, was confirmed by X-ray crystallographic analysis. Compounds 1 and 2 contain new bicyclic and tricyclic ring systems, respectively.

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.

Molecular cloning and expression of Hedychium coronarium farnesyl pyrophosphate synthase gene and its possible involvement in the biosynthesis of floral and wounding/herbivory induced leaf volatile sesquiterpenoids.

PubMed

Lan, Jian-bin; Yu, Rang-cai; Yu, Yun-yi; Fan, Yan-ping

2013-04-15

Farnesyl pyrophosphate synthase (FPPS EC 2.5.1.10) catalyzes the production of farnesyl pyrophosphate (FPP), which is a key precursor for many sesquiterpenoids such as floral scent and defense volatiles against herbivore attack. Here we report a new full-length cDNA encoding farnesyl diphosphate synthase from Hedychium coronarium. The open reading frame for full-length HcFPPS encodes a protein of 356 amino acids, which is 1068 nucleotides long with calculated molecular mass of 40.7 kDa. Phylogenetic tree analysis indicates that HcFPPS belongs to the plant FPPS super-family and has strong relationship with FPPS from Musa acuminata. Expression of the HcFPPS gene in Escherichia coli yielded FPPS activity. Tissue-specific and developmental analyses of the HcFPPS mRNA and corresponding volatile sesquiterpenoid levels in H. coronarium flowers revealed that the HcFPPS might play a regulatory role in floral volatile sesquiterpenoid biosynthesis. The emission of the FPP-derived volatile terpenoid correlates with strong expression of HcFPPS induced by mechanical wounding and Udaspes folus-damage in leaves, which suggests that HcFPPS may have an important ecological function in H. coronarium vegetative organ. Copyright © 2013 Elsevier B.V. All rights reserved.

Bioactivity-guided isolation of anti-hepatitis B virus active sesquiterpenoids from the traditional Chinese medicine: Rhizomes of Cyperus rotundus.

PubMed

Xu, Hong-Bo; Ma, Yun-Bao; Huang, Xiao-Yan; Geng, Chang-An; Wang, Hao; Zhao, Yong; Yang, Tong-Hua; Chen, Xing-Long; Yang, Cai-Yan; Zhang, Xue-Mei; Chen, Ji-Jun

2015-08-02

The rhizome of Cyperus rotundus (C. rotundus) is a well-known traditional Chinese medicine to cure hepatitis in many formulae, but the active components responsible for hepatitis have not been elucidated. According to our bioassay on HepG2.2.15 cell line in vitro, the ethanol extract of C. rotundus demonstrated potent anti-HBV activity. This current study was designed to isolate and identify the anti-HBV active constituents from the rhizomes of C. rotundus. Bioactivity and LC-MS guided fractionation on the extract of C. rotundus using various chromatographic techniques including open-column, Sephadex LH-20 and semi-preparative high performance liquid chromatography led to the isolation and identification of thirty-seven sesquiterpenoids. Structural elucidation of the isolates was carried out by extensive spectroscopic analyses (UV, IR, HRMS, 1D- and 2D -NMR). The anti-HBV activity and cytotoxicity were evaluated on the HBV-transfected HepG2.2.15 cell line in vitro. The cytotoxicity effects of the isolates were assessed by a MTT assay. The secretions of HBsAg and HBeAg in the culture medium were detected by ELISA method, and the load of HBV DNA was quantified by real-time fluorescent PCR technique. Five new patchoulane-type sesquiterpenoids, namely cyperene-3, 8-dione (1), 14-hydroxy cyperotundone (2), 14-acetoxy cyperotundone (3), 3β-hydroxycyperenoic acid (4) and sugetriol-3, 9-diacetate (5), along with 32 known sesquiterpenoids were isolated from the active fractions of C. rotundus. Compounds 2 and 3 were the first cyperotundone-type sesquiterpenoids with a hydroxyl group at C-14 position. Nine eudesmane-type sesquiterpenoids (15-21 and 23-24) significantly inhibited the HBV DNA replication with IC50 values of 42.7±5.9, 22.5±1.9, 13.2±1.2, 10.1±0.7, 14.1±1.1, 15.3±2.7, 13.8±0.9, 19.7±2.1 and 11.9±0.6 μM, respectively, of which, compounds 17, 21, 23 and 24 possessed high SI values of 250.4, 125.5,>259.6 and 127.5, respectively. Two patchoulane-type sesquiterpenoids (4 and 7) effectively suppressed the secretion of HBsAg in a dose-dependent manner with IC50 values of 46.6±14.3 (SI=31.0) and 77.2±13.0 (SI=1.7) μM, respectively. Compounds 2, 8, 12, 15, 17 and 25 possessed moderate activities against HBeAg secretion with IC50 values of 162.5±18.9 (SI=13.3), 399.2±90.0 (SI=10.6), 274.7±70.8 (SI=5.2), 313.9±87.5 (SI=7.2), 334.0±70.4 (SI=9.9) and 285.3±20.9 (SI=15.5) μM, respectively. This is the first study to reveal the anti-HBV constituents of C. rotundus, demonstrating that the eudesmane-type sesquiterpenoids might contribute to the anti-HBV activity of the rhizomes of C. rotundus. Copyright © 2015 Elsevier Ireland Ltd. All rights reserved.

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.

Induced Marine Fungus Chondrostereum sp. as a Means of Producing New Sesquiterpenoids Chondrosterins I and J by Using Glycerol as the Carbon Source

PubMed Central

Li, Hou-Jin; Jiang, Wen-Han; Liang, Wan-Ling; Huang, Jia-Xin; Mo, Yu-Fei; Ding, Yan-Qing; Lam, Chi-Keung; Qian, Xiao-Jun; Zhu, Xiao-Feng; Lan, Wen-Jian

2014-01-01

Chondrostereum sp., a marine fungus isolated from a soft coral Sarcophyton tortuosum, can yield hirsutane framework sesquiterpenoids. However, the metabolites profiles vary dramatically with the composition change of the culture media. This fungus was cultured in a liquid medium containing glycerol as the carbon source, and two new metabolites, chondrosterins I and J (1 and 2), were obtained. Their structures were elucidated primarily based on MS, NMR and X-ray single-crystal diffraction data. By comparison with the known hirsutane sesquiterpenoids, chondrosterins I and J have unique structural features, including a methyl was migrated from C-2 to C-6, and the methyl at C-3 was carboxylated. Compound 2 exhibited potent cytotoxic activities against the cancer cell lines CNE-1 and CNE-2 with the IC50 values of 1.32 and 0.56 μM. PMID:24402176

Discovery of methylfarnesoate as the annelid brain hormone reveals an ancient role of sesquiterpenoids in reproduction.

PubMed

Schenk, Sven; Krauditsch, Christian; Frühauf, Peter; Gerner, Christopher; Raible, Florian

2016-11-29

Animals require molecular signals to determine when to divert resources from somatic functions to reproduction. This decision is vital in animals that reproduce in an all-or-nothing mode, such as bristle worms: females committed to reproduction spend roughly half their body mass for yolk and egg production; following mass spawning, the parents die. An enigmatic brain hormone activity suppresses reproduction. We now identify this hormone as the sesquiterpenoid methylfarnesoate. Methylfarnesoate suppresses transcript levels of the yolk precursor Vitellogenin both in cell culture and in vivo , directly inhibiting a central energy-costly step of reproductive maturation. We reveal that contrary to common assumptions, sesquiterpenoids are ancient animal hormones present in marine and terrestrial lophotrochozoans. In turn, insecticides targeting this pathway suppress vitellogenesis in cultured worm cells. These findings challenge current views of animal hormone evolution, and indicate that non-target species and marine ecosystems are susceptible to commonly used insect larvicides.

Sesquiterpenoids from roots of Taraxacum laevigatum and Taraxacum disseminatum.

PubMed

Zielińiska, K; Kisiel, W

2000-08-01

Chromatographic separation of ethanolic root extracts of Taraxacum laevigatum and Taraxacum disseminatum afforded a total of eight germacrane- and eudesmane-type sesquiterpenoids. including new compounds, 1beta,3beta,6alpha-trihydroxy-4alpha( 15)-dihydrocostic acid methyl ester and its 1-O-beta-glucopyranoside. Their structures were established by spectroscopic analyses. In addition, the structure of 4alpha(15), 11beta(13)-tetrahydroridentin B-1-O-beta-glucopyranoside was elucidated by extensive NMR studies.

Three new drimane sesquiterpenoids from cultures of the fungus Penicillium sp.

PubMed

Ding, Jian-Hai; Ding, Zhang-Gui; Chunyu, Wei-Xun; Zhao, Jiang-Yuan; Wang, Hai-Bin; Liu, Shi-Wei; Wang, Fei

2017-08-01

Three new drimane sesquiterpenoids, 12-hydroxyalbrassitriol (1), drim-8(12)-en-6β,7α, 9α,11-tetraol (2), and drim-68(12)-dien-9α,11-diol (3), along with one known analog albrassitriol (4), were isolated from cultures of the tin mine tailings-associated fungus Penicillium sp. The new structures were determined on the basis of extensive spectroscopic analyses. All compounds were tested for their cytotoxicities against five human cancer cell lines.

Drimane Sesquiterpenoids and Isochromone Derivative from the Endophytic Fungus Pestalotiopsis sp. M-23.

PubMed

Kuang, Ce; Jing, Shu-Xi; Liu, Yan; Luo, Shi-Hong; Li, Sheng-Hong

2016-06-01

Three new drimane sesquiterpenoids (1-3) together with the known 2α-hydroxyisodrimeninol (4), and a new isochromone derivative (5), were obtained from the solid cultures of fungal strain Pestalotiopsis sp. M-23, an endophytic fungus isolated from the leaves of Leucosceptrum canum (Labiatae). Their structures were determined by comprehensive 1D and 2D NMR, and MS analyses. The metabolites were evaluated for their antibacterial activities, and compound 3 showed weak inhibitory activity against Bacillus subtilis.

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

Discovery of methylfarnesoate as the annelid brain hormone reveals an ancient role of sesquiterpenoids in reproduction

PubMed Central

Schenk, Sven; Krauditsch, Christian; Frühauf, Peter; Gerner, Christopher; Raible, Florian

2016-01-01

Animals require molecular signals to determine when to divert resources from somatic functions to reproduction. This decision is vital in animals that reproduce in an all-or-nothing mode, such as bristle worms: females committed to reproduction spend roughly half their body mass for yolk and egg production; following mass spawning, the parents die. An enigmatic brain hormone activity suppresses reproduction. We now identify this hormone as the sesquiterpenoid methylfarnesoate. Methylfarnesoate suppresses transcript levels of the yolk precursor Vitellogenin both in cell culture and in vivo, directly inhibiting a central energy–costly step of reproductive maturation. We reveal that contrary to common assumptions, sesquiterpenoids are ancient animal hormones present in marine and terrestrial lophotrochozoans. In turn, insecticides targeting this pathway suppress vitellogenesis in cultured worm cells. These findings challenge current views of animal hormone evolution, and indicate that non-target species and marine ecosystems are susceptible to commonly used insect larvicides. DOI: http://dx.doi.org/10.7554/eLife.17126.001 PMID:27894418

Molecular composition and paleobotanical origin of Eocene resin from northeast India

NASA Astrophysics Data System (ADS)

Rudra, Arka; Dutta, Suryendu; Raju, Srinivasan V.

2014-06-01

The molecular composition of fossil resins from early to middle Eocene coal from northeast India, has been analyzed for the first time to infer their paleobotanical source. The soluble component of fossil resin was analyzed using gas chromatography-mass spectrometry (GC-MS). The resin extracts are composed of cadalene-based C15 sesquiterpenoids and diagenetically altered triterpenoids. The macromolecular composition was investigated using pyrolysis gas chromatography-mass spectrometry (Py-GC-MS) and Fourier transform infrared (FTIR) spectroscopy. The major pyrolysis products are C15 bicyclic sesquiterpenoids, alkylated naphthalenes, benzenes and a series of C17-C34 n-alkene- n-alkane pairs. Spectroscopic analysis revealed the dominance of aliphatic components. The presence of cadalene-based sequiterpenoids confirms the resin to be Class II or dammar resin, derived from angiosperms of Dipterocarpaceae family. These sesquiterpenoids are often detected in many SE Asian fluvio-deltaic oils. Dipterocarpaceae are characteristic of warm tropical climate suggesting the prevalence of such climate during early Eocene in northeast India.

Psidials A-C, three unusual meroterpenoids from the leaves of Psidium guajava L.

PubMed

Fu, Hui-Zheng; Luo, Yong-Ming; Li, Chuang-Jun; Yang, Jing-Zhi; Zhang, Dong-Ming

2010-02-19

Three novel sesquiterpenoid-based meroterpenoids of psidials A-C (1-3) have been isolated from the leaves of Psidium guajava L. Their complete structures were elucidated by spectral and chemical methods, and that of 1 was confirmed by single-crystal X-ray diffraction analysis. Psidial B (2) and C (3) represented the new skeleton of the 3,5-diformylbenzyl phloroglucinol-coupled sesquiterpenoid. A possible biosynthetic pathway for 2-3 was postulated. 2-3 showed activity to enzyme PTP1B in 10 microM.

The complete genome sequence of Streptomyces albolongus YIM 101047, the producer of novel bafilomycins and odoriferous sesquiterpenoids.

PubMed

Yin, Min; Li, Guiding; Jiang, Yi; Han, Li; Huang, Xueshi; Lu, Tao; Jiang, Chenglin

2017-11-20

Streptomyces albolongus YIM 101047 produces novel bafilomycins and odoriferous sesquiterpenoids with cytotoxic and antimicrobial activities. Here, we report the complete genome sequence of S. albolongus YIM 101047, which consists of an 8,027,788bp linear chromosome. Forty-six putative biosynthetic gene clusters of secondary metabolites were found. The sesquiterpenoid gene cluster was on the left arm (0.09-0.10Mb), and the bafilomycin biosynthetic gene cluster was on the right arm (7.46-7.64Mb) of the chromosome. Twenty-two putative gene clusters with high or moderate similarity to important antibiotic biosynthetic gene clusters were found, including the antitumor agents bafilomycin, epothilone and hedamycin; the antibacterial/antifungal agents clavulanic acid, collismycin A, frontalamides, kanamycin, streptomycin and streptothricin; the protein phosphatase inhibitor RK-682; and the acute iron poisoning medication desferrioxamine B. The genome sequence reported here will enable us to study the biosynthetic mechanism of these important antibiotics and will facilitate the discovery of novel secondary metabolites with potential applications to human health. Copyright © 2017 Elsevier B.V. All rights reserved.

Traversing the fungal terpenome

PubMed Central

Quin, Maureen B.; Flynn, Christopher M.; Schmidt-Dannert, Claudia

2014-01-01

Fungi (Ascomycota and Basidiomycota) are prolific producers of structurally diverse terpenoid compounds. Classes of terpenoids identified in fungi include the sesqui-, di- and triterpenoids. Biosynthetic pathways and enzymes to terpenoids from each of these classes have been described. These typically involve the scaffold generating terpene synthases and cyclases, and scaffold tailoring enzymes such as e.g. cytochrome P450 monoxygenases, NAD(P)+ and flavin dependent oxidoreductases, and various group transferases that generate the final bioactive structures. The biosynthesis of several sesquiterpenoid mycotoxins and bioactive diterpenoids has been well-studied in Ascomycota (e.g. filamentous fungi). Little is known about the terpenoid biosynthetic pathways in Basidiomycota (e.g. mushroom forming fungi), although they produce a huge diversity of terpenoid natural products. Specifically, many trans-humulyl cation derived sesquiterpenoid natural products with potent bioactivities have been isolated. Biosynthetic gene clusters responsible for the production of trans-humulyl cation derived protoilludanes, and other sesquiterpenoids, can be rapidly identified by genome sequencing and bioinformatic methods. Genome mining combined with heterologous biosynthetic pathway refactoring has the potential to facilitate discovery and production of pharmaceutically relevant fungal terpenoids. PMID:25171145

Cyclodepsipeptides, sesquiterpenoids, and other cytotoxic metabolites from the filamentous fungus Trichothecium sp. (MSX 51320).

PubMed

Sy-Cordero, Arlene A; Graf, Tyler N; Adcock, Audrey F; Kroll, David J; Shen, Qi; Swanson, Steven M; Wani, Mansukh C; Pearce, Cedric J; Oberlies, Nicholas H

2011-10-28

Two new cyclodepsipeptides (1 and 2), two new sesquiterpenoids (3 and 4), and the known compounds guangomide A (5), roseotoxin S, and three simple trichothecenes were isolated from the cytotoxic organic extract of a terrestrial filamentous fungus, Trichothecium sp. The structures were determined using NMR spectroscopy and mass spectrometry. Absolute configurations of the cyclodepsipeptides were established by employing chiral HPLC, while the relative configurations of 3 and 4 were determined via NOESY data. The isolation of guangomide A was of particular interest, since it was reported previously from a marine-derived fungus.

The nature and origin of sesquiterpenoids in some tertiary fossil resins

NASA Astrophysics Data System (ADS)

Grantham, P. J.; Douglas, A. G.

1980-11-01

Analyses of two Tertiary fossil resins and a Tertiary montan wax have revealed the presence of a number of sesquiterpenoids. Using gas chromatographic retention data obtained on both polar and non-polar stationary phases and mass spectral comparisons with authentic compounds, the sesquiterpenoids α-cedrene, cedrane, cuparene, cedren-10-one, 8βH cedran-9-one and cuparenic acid have been identified in the fossil resin retinellite and a montain wax (both Oligocene) from lignite beds in the Bovey basin of Devon, England, and in the Pliocene fossil resin ionite from the lone valley of California. U.S.A. The sesquiterpenoids α-cedrene, cuparene and cuparenic acid are characteristic constituents of the essential oils of the Cupressaceae, a family of trees and shrubs of the order Coniferales, and it is argued that these fossil resins, and the montan wax, were derived from older forms of this family of plants. The ketones cedren-10-one and 8βH cedran-9-one, and the saturated hydrocarbon cedrane, are not reported to be constituents of modern genera of Cupressaceae and may have been formed during diagenesis. The cedrane occurring in these deposits appears to be a chemical hydrogenation product of α-cedrene. The ketones, on the other hand, may have resulted from the oxidation of α-cedrene although the mechanism of these reactions is not clear. If the ketones are not undetected constituents of these plants, then the presence in these deposits of both oxidised and fully-reduced α-cedrene products infers that separate phases of oxidation and reduction occurred during the diagenesis of the fossil resins and the montan wax.

Caryophyllene sesquiterpenoids from the endophytic fungus, Pestalotiopsis sp.

PubMed

Liu, Yi; Yang, Ming-Hua; Wang, Xiao-Bing; Li, Tian-Xiao; Kong, Ling-Yi

2016-03-01

Eight new caryophyllene sesquiterpenoids named pestaloporinates A-G (1-7) and 14-acetylhumulane (8) have been isolated from the solid cultures of an endophytic fungus Pestalotiopsis sp., which was obtained from the fresh stem bark of Melia azedarach Linn. Their structures as well as absolute configurations were determined by spectroscopic data, ECD experimentation, and single-crystal X-ray diffraction. Among all the isolates, compound 2 displayed potent inhibitory activity with IC50 value of 19.0 μM during the evaluation of nitric oxide (NO) inhibition in lipopolysaccharide (LPS)-induced RAW 264.7 macrophage cells. Copyright © 2015 Elsevier B.V. All rights reserved.

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.

Three new germacrane-type sesquiterpenes with NGF-potentiating activity from Valeriana officinalis var. latiofolia.

PubMed

Chen, Heng-Wen; Chen, Li; Li, Bin; Yin, Hai-Long; Tian, Ying; Wang, Qiong; Xiao, Yan-Hua; Dong, Jun-Xing

2013-11-14

Three new germacrane-type sesquiterpenoids, volvalerenal F (1), volvalerenal G (2) and volvalerenic acid D (3), along with five known compounds 4-8, were isolated from the CHCl₃ soluble partition of the ethanol extract of Valeriana officinalis var. latiofolia. The structures of the new compounds were determined on the basis of spectroscopic evidence, including their 1D- and 2D-NMR spectra, as well as mass spectrometry. The eight germacrane-type sesquiterpenoids showed nerve growth factor (NGF) potentiating activity, which mediates the neurite outgrowth in PC 12D cells. This study intends to reveal the chemical basis of the use of V. officinalis var. latiofolia as a dietary supplement.

Preparation of Sesquiterpenoids from Tussilago farfara L. by High-speed Counter-current Chromatography

PubMed Central

Cao, Kun; Xu, Yi; Zhao, Tian-Ming; Zhang, Qing

2016-01-01

Background: Sesquiterpenoids, such as tussilagone, has effects of raising blood pressure, antiplatelet aggregation, and anti-inflammation activities, which is regarded as index compound for quality control of Tussilago farfara L. Objective: This study was aimed to obtain an effective method for fast isolation of sesquiterpenoids from T. farfara L. by high-speed counter-current chromatography (HSCCC). Materials and Methods: A solvent optimization method for HSCCC was presented, i.e., the separation factors of compounds after the K values of solvent system should be investigated. Results: A ternary solvent system of n-hexane:methanol:water (5:8:2, v/v/v) was selected and applied for the HSCCC, and 56 mg of tussilagone (2) was isolated from T. farfara L., along with two other sesquiterpenoids 5.6 mg of 2,2-dimethyl-6-acetylchromanone (1) and 22 mg of 14-acetoxy-7 β-(3’-ethyl cis-crotonoyloxy)-lα-(2’-methylbutyryloxy)-notonipetranone (3) by HSCCC with high purities. Their chemical structures were elucidated by liquid chromatography-mass spectrometry and nuclear magnetic resonance experiments. Conclusion: These results offered an efficient strategy for preparation of potentially health-relevant phytochemicals from T. farfara L., which might be used for further chemical research and pharmacological studies by preparative HSCCC. SUMMARY The real separation efficiency has been verified by analytical HSCCC.A solvent optimization method for HSCCC was presented and applied to separate and prepare active compounds.A method for rapid and effective separation of target compound Tussilagone with high yield and purity from the flower buds of Tussilago farfara.Two other compounds 2,2-Dimethyl-6-acetylchromanone and 14-acetoxy-7β-(3’-ethyl cis-crotonoyloxy) -lα- (2’-methylbutyryloxy). notonipetranone hasbeen obtained with high purities from flower buds of Tussilago farfara. Abbreviations used: HSCCC: High-Speed Counter-Current Chromatography; LC-MS: Liquid Chromatograph-Mass Spectrometer; NMR: Nuclear Magnetic Resonance; TCM: Traditional Chinese Medicine; HPLC: High Performance Liquid Chromatography; ESI-MS: Electrospray Ionization Mass Spectrometry; PE: petroleum ether PMID:27867270

Preparative isolation and purification of three sesquiterpenoid lactones from Eupatorium lindleyanum DC. by high-speed counter-current chromatography.

PubMed

Yan, Guilong; Ji, Lilian; Luo, Yuming; Hu, Yonghong

2012-07-27

A high-speed counter-current chromatography (HSCCC) method was established for the preparative separation of three sesquiterpenoid lactones from Eupatorium lindleyanum DC. The two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water (1:4:2:3, v/v/v/v) was selected. From 540 mg of the n-butanol fraction of Eupatorium lindleyanum DC., 10.8 mg of 3β-hydroxy-8β-[4'-hydroxytigloyloxy]-costunolide, 17.9 mg of eupalinolide A and 19.3 mg of eupalinolide B were obtained in a one-step HSCCC separation, with purities of 91.8%, 97.9% and 97.1%, respectively, as determined by HPLC. Their structures were further identified by ESI-MS and ¹H-NMR.

Picrotoxane sesquiterpenoids from the stems of Dendrobium nobile and their absolute configurations and angiogenesis effect.

PubMed

Meng, Chun-Wang; He, Yu-Lin; Peng, Cheng; Ding, Xing-Jie; Guo, Li; Xiong, Liang

2017-09-01

Five picrotoxane sesquiterpenoids belonging to the unusual dendrobine-type (1 and 4) and the picrotoxinin-type (2, 3, and 5) were isolated from the stems of Dendrobium nobile Lindl. Their structures were established by spectroscopic analyses and physical properties. Compound 1 was a new dendrobine analogue. Although the planar structure of 2 and 3 had been reported, their absolute configurations were first determined by single-crystal X-ray diffraction and circular dichroism. Compound 2 exhibited angiogenesis effect against sunitinib-induced damage on intersegmental blood vessels in Tg (flk1: EGFP) and Tg (fli1: nEGFP) transgenic zebrafish at concentrations of 3.13, 6.25, 12.50, and 25.00μM. Copyright © 2017. Published by Elsevier B.V.

Gossypolhemiquinone, a dimeric sesquiterpenoid identified in cotton (Gossypium).

PubMed

Stipanovic, Robert; Puckhaber, Lorraine; Frelichowski, James; Esquivel, Jesus; Westbrook, John; O'Neil, Mike; Bell, Alois; Dowd, Michael; Hake, Kater; Duke, Sara

2016-02-01

The report that the cotton leaf perforator, Bucculatrix thurberiella, is one of the few insect herbivores to attack Gossypium thurberi prompted an investigation of the terpenoids present in the leaves of this wild species of cotton. Members of Gossypium produce subepidermal pigment glands in their leaves that contain the dimeric sesquiterpenoid gossypol as well as other biosynthetically related terpenoids. In addition to gossypol, a previously unknown dimeric sesquiterpenoid, gossypolhemiquinone (GHQ), was identified in trace amounts in G. thurberi, a member of the D genome. Other members of the D genome of Gossypium were subsequently found to contain this compound, but GHQ was not detected in commercial cotton cultivars. When fed to Helicoverpa zea in an artificial diet, GHQ delayed days-to-pupation, reduced pupal weights, and survival to adulthood to a lesser or equal extent than gossypol in comparison to the control diet. However, GHQ had a synergistic effect on survival and days-to-pupation when combined with gossypol at the highest dosage tested (0.18%; 15.5:84.5 GHQ:gossypol). Because gossypol exhibits anti-cancer activity, GHQ was also evaluated for its anti-cancer activity against the National Cancer Institute's 60-Human Tumor Cell Line Screen. Significant inhibitory activity against most of these cell lines was not observed, but the results may offer some promise against leukemia cancer cell lines. Published by Elsevier Ltd.

Sesquiterpenoids and lignans from the roots of Valeriana officinalis L.

PubMed

Wang, Peng-Cheng; Ran, Xin-Hui; Chen, Rui; Luo, Huai-Rong; Ma, Qing-Yun; Liu, Yu-Qing; Hu, Jiang-Miao; Huang, Sheng-Zhuo; Jiang, He-Zhong; Chen, Zhong-Quan; Zhou, Jun; Zhao, You-Xing

2011-10-01

Two new guaiane-type sesquiterpenoids, valerol A (1) and kessyl 3-acetate (2), together with nine known compounds, valeracetate (3), anismol A (4), orientalol C (5), spatulenol (6), 4α,10α-epoxyaromadendrane (7), (+)-8-hydroxypinoresinol (8), pinorespiol (9), pinoresinol 4-O-β-D-glucopyranoside (10), and 8-hydroxypinoresinol 4'-O-β-D-glucopyranoside (11) were isolated from the roots of Valeriana officinalis. The structures and relative configurations of 1 and 2 were elucidated on the basis of spectroscopic methods (1D- and 2D-NMR, MS, UV, and IR). These compounds were evaluated for inhibitory activity on acetylcholinesterase (AChE) and enhancing activity on nerve growth factor (NGF)-mediated neurite outgrowth in PC12 cells. Copyright © 2011 Verlag Helvetica Chimica Acta AG, Zürich.

Sesquiterpenoids and phenolics from Taraxacum hondoense.

PubMed

Kisiel, Wanda; Michalska, Klaudia

2005-09-01

Eleven sesquiterpene lactones, including the new guaianolide 11beta-hydroxydeacetylmatricarin-8-O-beta-glucopyranoside, along with four known phenolic glucosides were isolated from Taraxacum hondoense. The compounds were characterized by spectral methods.

Development of an efficient fractionation method for the preparative separation of sesquiterpenoids from Tussilago farfara by counter-current chromatography.

PubMed

Song, Kwangho; Lee, Kyoung Jin; Kim, Yeong Shik

2017-03-17

A novel application of counter-current chromatography (CCC) to enrich plant extracts using direct and continuous injection (CCC-DCI) was developed to fractionate sesquiterpenoids from the buds of Tussilago farfara L. In this study, an n-hexane-acetonitrile-water (HAcW) solvent system was separately pumped into the CCC column, and an extraction solution (45% acetonitrile) was directly and continuously injected into the CCC column. Since the extraction solution was used as a mobile phase in this method, solvent consumption could be greatly reduced. To enrich the extraction solution (315.9g/5.4L), only 4.2L water, 4.6L acetonitrile, and 1.2L n-hexane were used, including the extraction step. Finally, 6.8g of a sesquiterpenoid-enriched (STE) fraction was obtained from the crude extract (315.9g) of Tussilago farfara (1kg) in a single CCC run with a separation time of 8.5h. The sample injection capacity of CCC-DCI was greater than 300g; this amount of sample could not be handled in conventional CCC or other fractionation methods with the same column volume. Moreover, three major sesquiterpenoids (1: tussilagone, 2: 14-acetoxy-7β-(3'-ethyl cis-crotonoyloxy)-1α-(2'-methylburyryloxy)-notonipetranone, and 3: 7β-(3'-ethyl cis-crotonoyloxy)-1α-(2'-methylburyryloxy)-3, 14-dehydro-Z-notonipetranone) were purified from the STE fraction by CCC, and their chemical structures were elucidated by 1 H NMR and 13 C NMR. A quantification study was conducted, and the contents of compounds 1-3 in the CCC-DCI fraction were higher than those of conventional multi-step fractionations performed in series: solvent partitioning and open column chromatography. Furthermore, the average CCC-DCI recoveries were 96.1% (1), 96.9% (2), and 94.6% (3), whereas the open column chromatography recoveries were 77.7% (1), 66.5% (2), and 58.4% (3). The developed method demonstrates that CCC is a useful technique for enriching target components from natural products. Copyright © 2017 Elsevier B.V. All rights reserved.

Megalanthine, a bioactive sesquiterpenoid from Heliotropium megalanthum, its degradation products and their bioactivities.

PubMed

Macías, Francisco A; Simonet, Ana M; D'Abrosca, Brigida; Maya, Claudia C; Reina, Matías; González-Coloma, Azucena; Cabrera, Raimundo; Giménez, Cristina; Villarroel, Luis

2009-01-01

The new bioactive sesquiterpenoid (3R,6E)-2,6,10-trimethyl-3-(3-p-hydroxyphenylpropanoyloxy)-dodeca-6,11-diene-2,10-diol, named megalanthine, was isolated from the resinous exudates of Heliotropium megalanthum. The degradation products of this compound were identified. Several plant-defensive properties (insecticidal, antifungal, and phytotoxic) were evaluated after obtaining positive results in a preliminary etiolated wheat coleoptile bioassay. This bioassay showed the need to have both the phenolic and sesquiterpene moieties of the natural product present to achieve a biological effect. This result was confirmed in phytotoxicity bioassays. Megalanthine was ruled out as a significant plant-plant defense agent because of its lack of stability. The positive results recorded in the antifungal and antifeedant tests suggest, however, that this chemical is relevant in several ecological interactions involving H. megalanthum.

New Sesquiterpenoids and Anti-Platelet Aggregation Constituents from the Rhizomes of Curcuma zedoaria.

PubMed

Chen, Jih-Jung; Tsai, Tung-Han; Liao, Hsiang-Ruei; Chen, Li-Chai; Kuo, Yueh-Hsiung; Sung, Ping-Jyun; Chen, Chun-Lin; Wei, Chun-Sheng

2016-10-17

Two new sesquiterpenoids-13-hydroxycurzerenone ( 1 ) and 1-oxocurzerenone ( 2 )-have been isolated from the rhizomes of Curcuma zedoaria , together with 13 known compounds ( 3 - 15 ). The structures of two new compounds were determined through spectroscopic and MS analyses. Among the isolated compounds, 13-hydroxycurzerenone ( 1 ), 1-oxocurzerenone ( 2 ), curzerenone ( 3 ), germacrone ( 4 ), curcolone ( 5 ), procurcumenol ( 6 ), ermanin ( 7 ), curcumin ( 8 ), and a mixture of stigmast-4-en-3,6-dione ( 12 ) and stigmasta-4,22-dien-3,6-dione ( 13 ) exhibited inhibition (with inhibition % in the range of 21.28%-67.58%) against collagen-induced platelet aggregation at 100 μM. Compounds 1 , 5 , 7 , 8 , and the mixture of 12 and 13 inhibited arachidonic acid (AA)-induced platelet aggregation at 100 μM with inhibition % in the range of 23.44%-95.36%.

Methyl Farnesoate Plays a Dual Role in Regulating Drosophila Metamorphosis

PubMed Central

Wen, Di; Rivera-Perez, Crisalejandra; Abdou, Mohamed; Jia, Qiangqiang; He, Qianyu; Liu, Xi; Zyaan, Ola; Xu, Jingjing; Bendena, William G.; Tobe, Stephen S.; Noriega, Fernando G.; Palli, Subba R.; Wang, Jian; Li, Sheng

2015-01-01

Corpus allatum (CA) ablation results in juvenile hormone (JH) deficiency and pupal lethality in Drosophila. The fly CA produces and releases three sesquiterpenoid hormones: JH III bisepoxide (JHB3), JH III, and methyl farnesoate (MF). In the whole body extracts, MF is the most abundant sesquiterpenoid, followed by JHB3 and JH III. Knockout of JH acid methyl transferase (jhamt) did not result in lethality; it decreased biosynthesis of JHB3, but MF biosynthesis was not affected. RNAi-mediated reduction of 3-hydroxy-3-methylglutaryl CoA reductase (hmgcr) expression in the CA decreased biosynthesis and titers of the three sesquiterpenoids, resulting in partial lethality. Reducing hmgcr expression in the CA of the jhamt mutant further decreased MF titer to a very low level, and caused complete lethality. JH III, JHB3, and MF function through Met and Gce, the two JH receptors, and induce expression of Kr-h1, a JH primary-response gene. As well, a portion of MF is converted to JHB3 in the hemolymph or peripheral tissues. Topical application of JHB3, JH III, or MF precluded lethality in JH-deficient animals, but not in the Met gce double mutant. Taken together, these experiments show that MF is produced by the larval CA and released into the hemolymph, from where it exerts its anti-metamorphic effects indirectly after conversion to JHB3, as well as acting as a hormone itself through the two JH receptors, Met and Gce. PMID:25774983

New Gallotannin and other Phytochemicals from Sycamore Maple (Acer pseudoplatanus) Leaves.

PubMed

Zhang, Lu; Tu, Zong-cai; Yuan, Tao; Ma, Hang; Niesen, Daniel B; Wang, Hui; Seeram, Navindra P

2015-11-01

The maple (Acer) genus is a reported source of bioactive (poly)phenols, including gallotannins, but several of its members, such as the sycamore maple (A. pseudoplatanus), remain uninvestigated. Herein, thirty-nine compounds, including a new gallotannin, 1,2,3-tri-O-galloyl-6-O-(p-hydroxybenzoyl)-β-D- glucopyranoside (1), and thirty-eight (2-39) known compounds, consisting of four gallotannins, one ellagitannin, thirteen flavonoids, eight hydroxycinnamic acids, ten benzoic acid derivatives, and two sesquiterpenoids, were isolated from sycamore maple leaves. Their structures were determined based on NMR and mass spectral analyses. The isolates were evaluated for α-glucosidase inhibitory and antioxidant activities. Among the isolates, the gallotannins were the most potent α-glucosidase inhibitors with thirteen-fold more potent activity compared with the clinical drug, acarbose (IC50 = 16-31 vs. 218 µM). Similarly, the gallotannins showed the highest antioxidant activities, followed by the other phenolic sub-classes, while the sesquiterpenoids were inactive.

Sesquiterpene Synthase-3-Hydroxy-3-Methylglutaryl Coenzyme A Synthase Fusion Protein Responsible for Hirsutene Biosynthesis in Stereum hirsutum.

PubMed

Flynn, Christopher M; Schmidt-Dannert, Claudia

2018-06-01

The wood-rotting mushroom Stereum hirsutum is a known producer of a large number of namesake hirsutenoids, many with important bioactivities. Hirsutenoids form a structurally diverse and distinct class of sesquiterpenoids. No genes involved in hirsutenoid biosynthesis have yet been identified or their enzymes characterized. Here, we describe the cloning and functional characterization of a hirsutene synthase as an unexpected fusion protein of a sesquiterpene synthase (STS) with a C-terminal 3-hydroxy-3-methylglutaryl-coenzyme A (3-hydroxy-3-methylglutaryl-CoA) synthase (HMGS) domain. Both the full-length fusion protein and truncated STS domain are highly product-specific 1,11-cyclizing STS enzymes with kinetic properties typical of STSs. Complementation studies in Saccharomyces cerevisiae confirmed that the HMGS domain is also functional in vivo Phylogenetic analysis shows that the hirsutene synthase domain does not form a clade with other previously characterized sesquiterpene synthases from Basidiomycota. Comparative gene structure analysis of this hirsutene synthase with characterized fungal enzymes reveals a significantly higher intron density, suggesting that this enzyme may be acquired by horizontal gene transfer. In contrast, the HMGS domain is clearly related to other fungal homologs. This STS-HMGS fusion protein is part of a biosynthetic gene cluster that includes P450s and oxidases that are expressed and could be cloned from cDNA. Finally, this unusual fusion of a terpene synthase to an HMGS domain, which is not generally recognized as a key regulatory enzyme of the mevalonate isoprenoid precursor pathway, led to the identification of additional HMGS duplications in many fungal genomes, including the localization of HMGSs in other predicted sesquiterpenoid biosynthetic gene clusters. IMPORTANCE Hirsutenoids represent a structurally diverse class of bioactive sesquiterpenoids isolated from fungi. Identification of their biosynthetic pathways will provide access to this chemodiversity for the discovery and synthesis of molecules with new bioactivities. The identification and successful cloning of the previously elusive hirsutene synthase from the S. hirsutum provide important insights and strategies for biosynthetic gene discovery in Basidiomycota. The finding of a terpene synthase-HMGS fusion, the discovery of other sesquiterpenoid biosynthetic gene clusters with dedicated HMGS genes, and HMGS gene duplications in fungal genomes give new importance to the role of HMGS as a key regulatory enzyme in isoprenoid and sterol biosynthesis that should be exploited for metabolic engineering. Copyright © 2018 American Society for Microbiology.

Ligand binding pocket function of drosophila USP is necessary for metamorphosis

USDA-ARS?s Scientific Manuscript database

The widely accepted paradigm that epoxidized methyl farnesoates (“juvenile hormones,” JHs) are the principle sesquiterpenoid hormones regulating insect metamorphosis was assessed in Drosophila melanogaster. GC-MS analysis showed that methyl farnesoate, rather than methyl epoxyfarnesoate (= JH III), ...

Prenylated flavonol glycosides Epimedium grandiflorum: Cytotoxicity and evaluation against inflammation and metabolic disorders

USDA-ARS?s Scientific Manuscript database

Two new prenylated flavonol glycosides, epimedigrandiosides A and B (1 and 2), and 28 previously known compounds including prenylated flavonol derivatives, flavonol glycoside, megastigmanes, phenyl alkanoids, sesquiterpenoid glycoside, lignan, and hexene glucoside were isolated from the methanol ext...

The essence of insect metamorphosis and aging: electrical rewiring of cells driven by the principles of juvenile hormone-dependent Ca(2+)-homeostasis.

PubMed

De Loof, Arnold; De Haes, Wouter; Janssen, Tom; Schoofs, Liliane

2014-04-01

In holometabolous insects the fall to zero of the titer of Juvenile Hormone ends its still poorly understood "status quo" mode of action in larvae. Concurrently it initiates metamorphosis of which the programmed cell death of all internal tissues that actively secrete proteins, such as the fat body, midgut, salivary glands, prothoracic glands, etc. is the most drastic aspect. These tissues have a very well developed rough endoplasmic reticulum, a known storage site of intracellular Ca(2+). A persistent high [Ca(2+)]i is toxic, lethal and causal to apoptosis. Metamorphosis becomes a logical phenomenon if analyzed from: (1) the causal link between calcium toxicity and apoptosis; (2) the largely overlooked fact that at least some isoforms of Ca(2+)-ATPases have a binding site for farnesol-like endogenous sesquiterpenoids (FRS). The Ca(2+)-ATPase blocker thapsigargin, like JH a sesquiterpenoid derivative, illustrates how absence of JH might work. The Ca(2+)-homeostasis system is concurrently extremely well conserved in evolution and highly variable, enabling tissue-, developmental-, and species specificity. As long as JH succeeds in keeping [Ca(2+)]i low by keeping the Ca(2+)-ATPases pumping, it acts as "the status quo" hormone. When it disappears, its various inhibitory effects are lifted. The electrical wiring system of cells, in particular in the regenerating tissues, is subject to change during metamorphosis. The possibility is discussed that in vertebrates an endogenous farnesol-like sesquiterpenoid, probably farnesol itself, acts as a functional, but hitherto completely overlooked Juvenile anti-aging "Inbrome", a novel concept in signaling. Copyright © 2014 Elsevier Inc. All rights reserved.

Drimane Sesquiterpenoids Noncompetitively Inhibit Human α4β2 Nicotinic Acetylcholine Receptors with Higher Potency Compared to Human α3β4 and α7 Subtypes.

PubMed

Arias, Hugo R; Feuerbach, Dominik; Schmidt, Bernd; Heydenreich, Matthias; Paz, Cristian; Ortells, Marcelo O

2018-04-27

The drimane sesquiterpenoids drimenin, cinnamolide, dendocarbin A, and polygodial were purified from the Canelo tree ( Drimys winteri) and chemically characterized by spectroscopic methods. The pharmacological activity of these natural compounds were determined on hα4β2, hα3β4, and hα7 nicotinic acetylcholine receptors (AChRs) by Ca 2+ influx measurements. The results established that drimane sesquiterpenoids inhibit AChRs with the following selectivity: hα4β2 > hα3β4 > hα7. In the case of hα4β2 AChRs, the following potency rank order was determined (IC 50 's in μM): drimenin (0.97 ± 0.35) > cinnamolide (1.57 ± 0.36) > polygodial (62.5 ± 19.9) ≫ dendocarbin A (no activity). To determine putative structural features underlying the differences in inhibitory potency at hα4β2 AChRs, additional structure-activity relationship and molecular docking experiments were performed. The Ca 2+ influx and structural results supported a noncompetitive mechanism of inhibition, where drimenin interacted with luminal and nonluminal (TMD-β2 intrasubunit) sites. The structure-activity relationship results, i.e., the lower the ligand polarity, the higher the inhibitory potency, supported the nonluminal interaction. Ligand binding to both sites might inhibit the hα4β2 AChR by a cooperative mechanism, as shown experimentally ( n H > 1). Drimenin could be used as a molecular scaffold for the development of more potent inhibitors with higher selectivity for the hα4β2 AChR.

Relevance of trichothecenes in fungal physiology: Disruption of tri5 in Trichoderma arundinaceum

USDA-ARS?s Scientific Manuscript database

Trichothecenes are sesquiterpenoid mycotoxins produced mainly by Fusarium species. Harzianum A (HA), a non-phytotoxic trichothecene produced by Trichoderma arundinaceum, has recently been found to have antagonistic activity against fungal plant pathogens and to induce plant genes involved in defense...

Gossypolhemiquinone, a dimeric sesquiterpenoid identified in cotton (Gossypium)

USDA-ARS?s Scientific Manuscript database

The report that the cotton leaf perforator, Bucculatrix thurberiella, is one of the few insect herbivores to attack Gossypium thurberi prompted an investigation of the terpenoids present in the leaves of this wild species of cotton. Members of Gossypium produce subepidermal pigment glands in their ...

Gossypolone and Gossypolhemiquinone: Biological activity of terpenoids found in cotton (Gossypium)

USDA-ARS?s Scientific Manuscript database

The wild cotton plant, Gossypium thurberi grows in the Sonoran Desert in northern Mexico and southern Arizona, and is attacked by few herbivorous insects (Korban, 1999). In general, members of Gossypium produce a rich assortment of sesquiterpenoid and sesterterpenoids in the subepidermal pigment gl...

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.

Effect of trichothecene production on the plant defense response and fungal physiology: overexpression of Trichoderma arundinaceum tri4 gene in T. harzianum

USDA-ARS?s Scientific Manuscript database

Trichothecenes are fungal sesquiterpenoid compounds, the majority of which have phytotoxic activity. They contaminate food and feed stocks, resulting in potential harm to animals and human beings. Trichoderma brevicompactum and T. arundinaceum produce trichodermin and harzianum A (HA), respectively,...

Further sesquiterpenoids and phenolics from Taraxacum officinale.

PubMed

Kisiel, W; Barszcz, B

2000-06-01

Five germacrane- and guaiane-type sesquiterpene lactones, including two previously described taraxinic acid derivatives, were isolated from the roots of Taraxacum officinale, together with benzyl glucoside, dihydroconiferin, syringin and dihydrosyringin. The other three lactones were identified as 11beta, 13-dihydrolactucin, ixerin D and ainslioside. Moreover, the stereochemistry at C-11 in dihydrotaraxinic acid was assigned.

Production of trichodiene by Trichoderma harzianum alters the perception of this biocontrol strain by plants and antagonized fungi

USDA-ARS?s Scientific Manuscript database

Trichothecenes are phytotoxic sesquiterpenoid compounds of fungal origin which can act as virulence factors in plant diseases. Harzianum A (HA) is a non-phytotoxic trichothecene produced by Trichoderma arundinaceum. The first step in the biosynthesis of HA is the conversion of farnesyl diphosphate t...

Heterologous expression of tri5 gene in Trichoderma harzianum: Effect of trichodiene production on Trichoderma environmental interactions

USDA-ARS?s Scientific Manuscript database

Terpenes form a large class of compounds that have a variety of roles in mediating antagonistic and beneficial interactions among organisms. The trichothecenes are phytotoxic sesquiterpenoid compounds that have been extensively studied, mainly in the genus Fusarium, that can act as virulence factors...

Antifungal activity of Piper diospyrifolium Kunth (Piperaceae) essential oil

PubMed Central

Vieira, Silvia Cristina Heredia; de Paulo, Luis Fernando; Svidzinski, Terezinha Inez Estivaleti; Dias Filho, Benedito Prado; Nakamura, Celso Vataru; de Souza, Amanda; Young, Maria Cláudia Marx; Cortez, Diógenes Aparício Garcia

2011-01-01

In vitro activity of the essential oil from Piper diospyrifolium leaves was tested using disk diffusion techniques. The antifungal assay showed significant potencial antifungal activity: the oil was effective against several clinical fungal strains. The majority compounds in the essential oil were identified as sesquiterpenoids by GC-MS and GC-FID techniques. PMID:24031717

Allelopathic agents from Cyrtocymura cincta.

PubMed

Alvarez Valdés, D; Elías, A; Bardón, A

2001-01-01

The sesquiterpenoid fractions from the chloroform extracts of roots and aerial parts of the weed Cyrtocymura cincta (Griseb.) H. Robinson (Compositae) were tested to observe the effects on seed germination and growth of three dicot and four monocot species. Promotion and inhibition effects were observed according to the examined compound, specific seed or cultivar, and concentration.

The intensely sweet herb, Lippia dulcis Trev.: historical uses, field inquiries, and constituents.

PubMed

Compadre, C M; Robbins, E F; Kinghorn, A D

1986-01-01

Lippia dulcis Trev. (Verbenaceae) is the source of hernandulcin, the first known intensely sweet sesquiterpenoid, a compound which is a volatile oil constituent. The literature on the uses of this species, dating back to early colonial times in Mexico, has been examined. This plant began to be used as an official drug in the late 19th century for the treatment of coughs and bronchitis, and at that time preliminary phytochemical investigations were undertaken. Field work carried out in Mexico in 1981 and 1982 has indicated that there is still an active trade involving L. dulcis, which is sold primarily in market places for its alleged abortifacient activity. We have obtained no evidence, either from the literature or from field inquiries, that L. dulcis has ever been used for sweetening foods or beverages. Fourteen L. dulcis volatile oil constituents, mainly mono- and sesquiterpenoids, were identified by gas chromatography/mass spectrometry. The toxic compound, camphor, was found to constitute 53% w/w of the volatile oil of this species. The potential use of L. dulcis for the extraction of hernandulcin is discussed.

Anti-viral and cytotoxic norbisabolane sesquiterpenoid glycosides from Phyllanthus emblica and their absolute configurations.

PubMed

Lv, Jun-Jiang; Yu, Shan; Xin, Ying; Cheng, Rong-Rong; Zhu, Hong-Tao; Wang, Dong; Yang, Chong-Ren; Xu, Min; Zhang, Ying-Jun

2015-09-01

In an effort to identify anti-viral and cytotoxic compounds from Phyllanthus spp., 14 highly oxygenated norbisabolane sesquiterpenoids, phyllaemblicins H1-H14, were isolated from the roots of Phyllanthus emblica Linn, along with phyllaemblicins B and C and glochicoccinoside D. Their structures were determined on the basis of detailed spectroscopic analysis and chemical methods. Determination of absolute configurations of these compounds was facilitated by theoretical calculations of electronic circular dichroism (ECD) spectra using time-dependent density functional theory (TDDFT) for the aglycone components, and pre-column derivative/chiral HPLC analysis for the monosaccharides. The known glochicoccinoside D displayed potent activity against influenza A virus strain H3N2 and hand, foot and mouth virus EV71, with IC50 values of 4.5±0.6 and 2.6±0.7 μg/ml, respectively. Phyllaemblicin H1 showed moderate cytotoxicity against human cancer cell lines A-549 and SMMC-7721, with IC50 values of 4.7±0.7 and 9.9±1.3 μM, respectively. Copyright © 2015 Elsevier Ltd. All rights reserved.

New benzoate derivatives and hirsutane type sesquiterpenoids with antimicrobial activity and cytotoxicity from the solid-state fermented rice by the medicinal mushroom Stereum hirsutum.

PubMed

Ma, Ke; Bao, Li; Han, Junjie; Jin, Tao; Yang, Xiaoli; Zhao, Feng; Li, Shaifei; Song, Fuhang; Liu, Miaomiao; Liu, Hongwei

2014-01-15

In addition to the fruiting bodies, mushroom mycelia can be used as functional foods and nutraceutical materials. In this study, two new benzoate derivatives (1 and 2) and three new sesquiterpenoids (3-5) were isolated from the mycelia of Stereum hirsutum. Their chemical structures were elucidated by NMR experiments. The absolute configuration in 3 was assigned by X-ray crystallographic analysis. In bioactivities evaluation, compounds 1 and 2 showed antimicrobial effects against methicillin-resistant Staphylococcusaureus, and S. aureus with the MIC values of 25.0μg/mL; compounds 1 and 3 inhibited the NO overproduction in the LPS-induced macrophages with the IC50 values of 19.17 and 15.44μM, and also displayed cytotoxicity against A549 and HepG2 with IC50 in the range of 10-50μM. These results support the usage of the mycelia of S. hirsutum as a good functional food. Copyright © 2013 Elsevier Ltd. All rights reserved.

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.

Total Synthesis of Jiadifenolide**

PubMed Central

Paterson, Ian; Xuan, Mengyang; Dalby, Stephen M

2014-01-01

As a potent neurotrophic agent, the sesquiterpenoid jiadifenolide represents a valuable small-molecule lead for the potential therapeutic treatment of neurodegenerative diseases. A stereocontrolled total synthesis of this densely functionalized natural product is reported, central to which is an adventurous samarium-mediated cyclization reaction to establish the tricyclic core and the adjacent C5 and C6 quaternary stereocenters. PMID:24861364

Trichothecenes and aspinolides produced by Trichoderma arundinaceum regulate expression of Botrytis cinerea genes involved in virulence and growth

USDA-ARS?s Scientific Manuscript database

Trichoderma arundinaceum (Ta37) and Botrytis cinerea (B05.10) produce the sesquiterpenoids harzianum A (HA) and botrydial (BOT), respectively. Ta'Tri5, an HA non-producer mutant, produces high levels of the polyketide compounds aspinolides (Asp) B and C. We analyzed the role of HA and Asp in the B. ...

Essential oil from leaves of Lippia dulcis grown in Colombia.

PubMed

Moreno-Murillo, Bárbara; Quijano-Célis, Clara; Romero, Arturo R; Pino, Jorge A

2010-04-01

The chemical composition of the volatile compounds from the leaves of Lippia dulcis Trev. (Verbenaceae) from Colombia was studied by GC and GC/MS. Forty volatile compounds were identified, of which the major ones were alpha-copaene (18.0%), beta-caryophyllene (17.8%), and delta-cadinene (14.7%). The sweet bisabolane sesquiterpenoid, hernandulcin, formed only 1.1% of the leaf oil.

Suites of Terpene Synthases Explain Differential Terpenoid Production in Ginger and Turmeric Tissues

PubMed Central

Koo, Hyun Jo; Gang, David R.

2012-01-01

The essential oils of ginger (Zingiber officinale) and turmeric (Curcuma longa) contain a large variety of terpenoids, some of which possess anticancer, antiulcer, and antioxidant properties. Despite their importance, only four terpene synthases have been identified from the Zingiberaceae family: (+)-germacrene D synthase and (S)-β-bisabolene synthase from ginger rhizome, and α-humulene synthase and β-eudesmol synthase from shampoo ginger (Zingiber zerumbet) rhizome. We report the identification of 25 mono- and 18 sesquiterpene synthases from ginger and turmeric, with 13 and 11, respectively, being functionally characterized. Novel terpene synthases, (−)-caryolan-1-ol synthase and α-zingiberene/β-sesquiphellandrene synthase, which is responsible for formation of the major sesquiterpenoids in ginger and turmeric rhizomes, were also discovered. These suites of enzymes are responsible for formation of the majority of the terpenoids present in these two plants. Structures of several were modeled, and a comparison of sets of paralogs suggests how the terpene synthases in ginger and turmeric evolved. The most abundant and most important sesquiterpenoids in turmeric rhizomes, (+)-α-turmerone and (+)-β-turmerone, are produced from (−)-α-zingiberene and (−)-β-sesquiphellandrene, respectively, via α-zingiberene/β-sesquiphellandrene oxidase and a still unidentified dehydrogenase. PMID:23272109

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.

Structure-Activity Relationship Studies on Derivatives of Eudesmanolides from Inula Helenium as Toxicants against Aedes Aegypti Larvae and Adults

DTIC Science & Technology

2010-01-01

flavonoids , sesquiterpenoids, and triterpenoids, among others, were CHEMISTRY & BIODIVERSITY – Vol. 7 (2010)1682 Table 1. Larvicidal Activities of Various...Gainesville, FL 32608, USA c) Department of Chemistry , Louisiana State University, Baton Rouge, Louisiana 70803, USA AnAedes aegypti larval toxicity...bioassay was performed on compounds representing many classes of natural compounds including polyacetylenes, phytosterols, flavonoids

Colletotrichine A, a new sesquiterpenoid from Colletotrichum gloeosporioides GT-7, a fungal endophyte of Uncaria rhynchophylla.

PubMed

Chen, Xiao-Wei; Yang, Zhong-Duo; Sun, Jian-Hui; Song, Tong-Tong; Zhu, Bao-Ying; Zhao, Jun-Wen

2018-04-01

One new compound, Colletotrichine A (1), was produced by the fungal Colletotrichum gloeosporioides GT-7. The structure was established by 1D and 2D NMR spectra. Monoamine oxidase (MAO) and acetylcholinesterase (AChE) inhibitory activity of 1 was also evaluated. Compound 1 showed AChE-inhibiting activity with IC 50 value of 28 μg/mL.

Three new diterpenoids from the fruit of Vitex agnus-castus.

PubMed

Ono, Masateru; Nagasawa, Yumiko; Ikeda, Tsuyoshi; Tsuchihashi, Ryota; Okawa, Masafumi; Kinjo, Junei; Yoshimitsu, Hitoshi; Nohara, Toshihiro

2009-10-01

Three new labdane-type diterpenoids, viteagnusins F, G, and H, were isolated from the hexane extract of fruit (chasteberry) of Vitex agnus-castus L. (Verbenaceae) along with seven known compounds including four labdane-type diterpenoids, one norlabdane-type diterpenoid, one aromadendrane-type sesquiterpenoid, and one flavonoid. The chemical structures of the three new labdane-type diterpenoids were determined on the basis of spectroscopic data as well as chemical evidence.

Xanthanolides and xanthane epoxide derivatives from Xanthium strumarium.

PubMed

Mahmoud, A A

1998-12-01

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

The transcriptome of sesquiterpenoid biosynthesis in heartwood xylem of Western Australian sandalwood (Santalum spicatum).

PubMed

Moniodis, Jessie; Jones, Christopher G; Barbour, E Liz; Plummer, Julie A; Ghisalberti, Emilio L; Bohlmann, Joerg

2015-05-01

The fragrant heartwood oil of West Australian sandalwood (Santalum spicatum) contains a mixture of sesquiterpene olefins and alcohols, including variable levels of the valuable sesquiterpene alcohols, α- and β-santalol, and often high levels of E,E-farnesol. Transcriptome analysis revealed sequences for a nearly complete set of genes of the sesquiterpenoid biosynthetic pathway in this commercially valuable sandalwood species. Transcriptome sequences were produced from heartwood xylem tissue of a farnesol-rich individual tree. From the assembly of 12,537 contigs, seven different terpene synthases (TPSs), several cytochromes P450, and allylic phosphatases were identified, as well as transcripts of the mevalonic acid and methylerythritol phosphate pathways. Five of the S. spicatum TPS sequences were previously unknown. The full-length cDNA of SspiTPS4 was cloned and the enzyme functionally characterized as a multi-product sesquisabinene B synthase, which complements previous characterization of santalene and bisabolol synthases in S. spicatum. While SspiTPS4 and previously cloned sandalwood TPSs do not explain the prevalence of E,E-farnesol in S. spicatum, the genes identified in this and previous work can form a basis for future studies on natural variation of sandalwood terpenoid oil profiles. Copyright © 2014 Elsevier Ltd. All rights reserved.

Diversity of sesquiterpene synthases in the basidiomycete Coprinus cinereus

PubMed Central

Agger, Sean; Lopez-Gallego, Fernando; Schmidt-Dannert, Claudia

2009-01-01

SUMMARY Fungi are a rich source of bioactive secondary metabolites and mushroom-forming fungi (Agaricomycetes) are especially known for the synthesis of numerous bioactive and often cytotoxic sesquiterpenoid secondary metabolites. Compared to the large number of sesquiterpene synthases identified in plants, less than a handful of unique sesquiterpene synthases have been described from fungi. Here we describe the functional characterization of six sesquiterpene synthases (Cop1 to Cop6) and two terpene oxidizing cytochrome P450 monooxygenases (Cox1 and Cox2) from Coprinus cinereus. The genes were cloned and, except for cop5, functionally expressed in Escherichia coli and/or Saccharomyces cerevisiae. Cop1 and Cop2 each synthesize germacrene A as the major product. Cop3 was identified as a α-muurolene synthase, an enzyme that has not been described previously, while Cop4 synthesizes δ-cadinene as its major product. Cop6 was originally annotated as a trichodiene synthase homolog, but instead was found to catalyze highly specific the synthesis of α-cuprenene. Co-expression of cop6 and the two monooxygenase genes next to it yields oxygenated α-cuprenene derivatives, including cuparophenol, suggesting that these genes encode the enzymes for the biosynthesis of antimicrobial quinone sesquiterpenoids (known as lagopodins) that were previously isolated from C. cinereus and other Coprinus species. PMID:19400802

Volatile compounds in cryptic species of the Aneura pinguis complex and Aneura maxima (Marchantiophyta, Metzgeriidae).

PubMed

Wawrzyniak, Rafał; Wasiak, Wiesław; Bączkiewicz, Alina; Buczkowska, Katarzyna

2014-09-01

Aneura pinguis is one of the liverwort species complexes that consist of several cryptic species. Ten samples collected from different regions in Poland are in the focus of our research. Eight of the A. pinguis complex belonging to four cryptic species (A, B, C, E) and two samples of closely related species Aneura maxima were tested for the composition of volatile compounds. The HS-SPME technique coupled to GC/FID and GC/MS analysis has been applied. The fiber coated with DVB/CAR/PDMS has been used. The results of the present study, revealed the qualitative and quantitative differences in the composition of the volatile compounds between the studied species. Mainly they are from the group of sesquiterpenoids, oxygenated sesquiterpenoids and aliphatic hydrocarbons. The statistical methods (CA and PCA) showed that detected volatile compounds allow to distinguish cryptic species of A. pinguis. All examined cryptic species of the A. pinguis complex differ from A. maxima. Species A and E of A. pinguis, in CA and PCA, form separate clusters remote from two remaining cryptic species of A. pinguis (B and C) and A. maxima. Relationship between the cryptic species appeared from the chemical studies are in accordance with that revealed on the basis of DNA sequences. Copyright © 2014 Elsevier Ltd. All rights reserved.

The bouquet of grapevine (Vitis vinifera L. cv. Cabernet Sauvignon) flowers arises from the biosynthesis of sesquiterpene volatiles in pollen grains

PubMed Central

Martin, Diane M.; Toub, Omid; Chiang, Angela; Lo, Bernard C.; Ohse, Sebastian; Lund, Steven T.; Bohlmann, Jörg

2009-01-01

Terpenoid volatiles are important information molecules that enable pollinators to locate flowers and may protect reproductive tissues against pathogens or herbivores. Inflorescences of grapevine (Vitis vinifera L.) are composed of tiny green flowers that produce an abundance of sesquiterpenoid volatiles. We demonstrate that male flower parts of grapevines are responsible for sesquiterpenoid floral scent formation. We describe temporal and spatial patterns of biosynthesis and release of floral volatiles throughout the blooming of V. vinifera L. cv. Cabernet Sauvignon. The biosynthesis of sesquiterpene volatiles, which are emitted with a light-dependent diurnal pattern early in the morning at prebloom and bloom, is localized to anthers and, more specifically, within the developing pollen grains. Valencene synthase (VvValCS) enzyme activity, which produces the major sesquiterpene volatiles of grapevine flowers, is present in anthers. VvValCS transcripts are most abundant in flowers at prebloom stages. Western blot analysis identified VvValCS protein in anthers, and in situ immunolabeling located VvValCS protein in pollen grains during bloom. Histochemical staining, as well as immunolabeling analysis by fluorescent microscopy and transmission electron microscopy, indicated that VvValCS localizes close to lipid bodies within the maturing microspore. PMID:19359488

The structure-activity relationships of mansonone F, a potent anti-MRSA sesquiterpenoid quinone: SAR studies on the C6 and C9 analogs.

PubMed

Suh, Young-Ger; Kim, Sun Nam; Shin, Dong-Yun; Hyun, Soon-Sil; Lee, Do-Sang; Min, Kyung-Hoon; Han, Sae Mi; Li, Funan; Choi, Eung-Chil; Choi, Seong-Hak

2006-01-01

For the systematic SAR study on mansonone F, a series of C6 and C9 analogs of mansonone F have been synthesized and their anti-MRSA activities were evaluated. Most of the analogs exhibited good or excellent anti-MRSA activities. In particular, the 6-n-butylmansonone F showed fourfold higher antibacterial activities compared to that of vancomycin.

Terpenoids from Tripterygium doianum (Celastraceae).

PubMed

Tanaka, Naonobu; Duan, Hongquan; Takaishi, Yoshihisa; Kawazoe, Kazuyoshi; Goto, Satoru

2002-09-01

The extract of Tripterygium doianum (Celastraceae) afforded three triterpenoids [3beta-acetoxy-11-ursen-13alpha,30-olide, 25-chloro-24-hydroxytirucall-7-en-3-one and tirucall-7-en-3,24-dione], two sesquiterpenoids [5alpha-acetoxy-1beta,8alpha-bis-cinnamoyl-4alpha-hydroxydihydroagarofuran and 5alpha-acetoxy-1beta-benzoyl-8alpha-cinnamoyl-4alpha-hydroxydihydroagarofuran] and nine known triterpenoids. Their structures were established based on spectroscopic studies. Copyright 2002 Elsevier Science Ltd.

Sesquiterpenoids and phenolics from roots of Taraxacum udum.

PubMed

Michalska, Klaudia; Marciniuk, Jolanta; Kisiel, Wanda

2010-07-01

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

Flavonoids and terpenoids from Luma gayana (Barn.) Burret.

PubMed

Wächter, G A; Wangmaneerat, A; Caple, K M; Montenegro, G; Timmermann, B N

1999-12-01

The flavonoids 5-hydroxy-7-methoxyflavanone, 6,8-dimethyl-5,7-dihydroxyflavanone and 2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone, a mixture of alkyl esters of p-coumaric acid, the triterpenoids oleanolic acid and maslinic acid, the monoterpenoid 1 alpha,2 beta,4 beta-trihydroxy-p-menthane, the sesquiterpenoid clovandiol and beta-sitosterol were isolated from the aerial parts of Luma gayana (Barn.) Burret. This is the first report on the chemistry of this species.

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.

Volvalerine A, an unprecedented N-containing sesquiterpenoid dimer derivative from Valeriana officinalis var. latifolia.

PubMed

Wang, Peng-Cheng; Ran, Xin-Hui; Luo, Huai-Rong; Ma, Qing-Yun; Zhou, Jun; Hu, Jiang-Miao; Zhao, You-Xing

2016-03-01

Volvalerine A (1), a novel N-containing bisesquiterpenoid derivative with a dihydroisoxazole ring, and its possible biosynthetic precursor, 1-hydroxy-1,11,11-trimethyldecahydrocyclopropane azulene-10-one (2), were isolated from the roots of Valeriana officinalis var. latifolia. Their structures and relative configurations were identified using spectroscopic data and X-ray crystallography. A plausible biosynthetic pathway for 1 is also presented. Copyright © 2016 Elsevier B.V. All rights reserved.

Insights into the Sesquiterpenoid Pathway by Metabolic Profiling and De novo Transcriptome Assembly of Stem-Chicory (Cichorium intybus Cultigroup “Catalogna”)

PubMed Central

Testone, Giulio; Mele, Giovanni; Di Giacomo, Elisabetta; Gonnella, Maria; Renna, Massimiliano; Tenore, Gian Carlo; Nicolodi, Chiara; Frugis, Giovanna; Iannelli, Maria Adelaide; Arnesi, Giuseppe; Schiappa, Alessandro; Giannino, Donato

2016-01-01

Stem-chicory of the “Catalogna” group is a vegetable consumed for bitter-flavored stems. Type and levels of bitter sesquiterpene lactones (STLs) participate in conferring bitterness in vegetables. The content of lactucin—and lactucopocrin-like STLs was higher in “Molfettese” than “Galatina” landrace stalks, regardless of the cultivation sites, consistently with bitterness scores and gustative differences. The “Galatina” transcriptome assembly resulted in 58,872 unigenes, 77% of which were annotated, paving the way to molecular investigation of the STL pathway. Comparative transcriptome analysis allowed the identification of 69,352 SNPs and of 1640 differentially expressed genes that maintained the pattern independently of the site. Enrichment analyses revealed that 4 out of 29 unigenes were up-regulated in “Molfettese” vs “Galatina” within the sesquiterpenoid pathway. The expression of two germacrene A -synthase (GAS) and one -oxidase (GAO) genes of the costunolide branch correlated positively with the contents of lactucin-like molecules, supporting that STL biosynthesis regulation occurs at the transcriptional level. Finally, 46 genes encoding transcription factors (TFs) maintained a differential expression pattern between the two varieties regardless of the growth site; correlation analyses among TFs, GAS, GAO gene expressions and STLs contents suggest that one MYB and one bHLH may act in the pathway. PMID:27877190

Xanthorrhizol induced DNA fragmentation in HepG2 cells involving Bcl-2 family proteins

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

Tee, Thiam-Tsui, E-mail: thiamtsu@yahoo.com; Cheah, Yew-Hoong; Bioassay Unit, Herbal Medicine Research Center, Institute for Medical Research, Jalan Pahang, Kuala Lumpur

Highlights: Black-Right-Pointing-Pointer We isolated xanthorrhizol, a sesquiterpenoid compound from Curcuma xanthorrhiza. Black-Right-Pointing-Pointer Xanthorrhizol induced apoptosis in HepG2 cells as observed using SEM. Black-Right-Pointing-Pointer Apoptosis in xanthorrhizol-treated HepG2 cells involved Bcl-2 family proteins. Black-Right-Pointing-Pointer DNA fragmentation was observed in xanthorrhizol-treated HepG2 cells. Black-Right-Pointing-Pointer DNA fragmentation maybe due to cleavage of PARP and DFF45/ICAD proteins. -- Abstract: Xanthorrhizol is a plant-derived pharmacologically active sesquiterpenoid compound isolated from Curcuma xanthorrhiza. Previously, we have reported that xanthorrhizol inhibited the proliferation of HepG2 human hepatoma cells by inducing apoptotic cell death via caspase activation. Here, we attempt to further elucidate the mode of action ofmore » xanthorrhizol. Apoptosis in xanthorrhizol-treated HepG2 cells as observed by scanning electron microscopy was accompanied by truncation of BID; reduction of both anti-apoptotic Bcl-2 and Bcl-X{sub L} expression; cleavage of PARP and DFF45/ICAD proteins and DNA fragmentation. Taken together, these results suggest xanthorrhizol as a potent antiproliferative agent on HepG2 cells by inducing apoptosis via Bcl-2 family members. Hence we proposed that xanthorrhizol could be used as an anti-liver cancer drug for future studies.« less

Xanthorrhizol, a natural sesquiterpenoid, induces apoptosis and growth arrest in HCT116 human colon cancer cells.

PubMed

Kang, You-Jin; Park, Kwang-Kyun; Chung, Won-Yoon; Hwang, Jae-Kwan; Lee, Sang Kook

2009-11-01

Xanthorrhizol is a sesquiterpenoid from the rhizome of Curcuma xanthorrhiza. In our previous studies, xanthorrhizol suppressed cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) expression, inhibited cancer cell growth, and exerted an anti-metastatic effect in an animal model. However, the exact mechanisms for its inhibitory effects against cancer cell growth have not yet been fully elucidated. In the present study, we investigated the growth inhibitory effect of xanthorrhizol on cancer cells. Xanthorrhizol dose-dependently exerted antiproliferative effects against HCT116 human colon cancer cells. Xanthorrhizol also arrested cell cycle progression in the G0/G1 and G2/M phase and induced the increase of sub-G1 peaks. Cell cycle arrest was highly correlated with the downregulation of cyclin A, cyclin B1, and cyclin D1; cyclin-dependent kinase 1 (CDK1), CDK2, and CDK4; proliferating cell nuclear antigen; and inductions of p21 and p27, cyclin-dependent kinase inhibitors. The apoptosis by xanthorrhizol was markedly evidenced by induction of DNA fragmentation, release of cytochrome c, activation of caspases, and cleavage of poly-(ADP-ribose) polymerase. In addition, xanthorrhizol increased the expression and promoter activity of pro-apoptotic non-steroidal anti-inflammatory drug-activated gene-1 (NAG-1). These findings provide one plausible mechanism for the growth inhibitory activity of xanthorrhizol against cancer cells.

Syntheses and anti-MRSA activities of the C3 analogs of mansonone F, a potent anti-bacterial sesquiterpenoid: insights into its structural requirements for anti-MRSA activity.

PubMed

Shin, Dong-Yun; Kim, Sun Nam; Chae, Jung-Hyun; Hyun, Soon-Sil; Seo, Seung-Yong; Lee, Yong-Sil; Lee, Kwang-Ok; Kim, Seok-Ho; Lee, Yun-Sang; Jeong, Jae Min; Choi, Nam-Song; Suh, Young-Ger

2004-09-06

Syntheses and excellent anti-MRSA activities of the mansonone F analogs are reported. In addition, the minimal structural requirements for its anti-MRSA activities as well as its structure-activity relationship including the C3 substituents effects on anti-MRSA activity are also described. In particular, this study revealed that both ortho-quinone and tricyclic systems of mansonone F are essential for anti-MRSA activities.

Inhibition of lipopolysaccharide-induced inducible nitric oxide synthase and cyclooxygenase-2 expression by xanthanolides isolated from Xanthium strumarium.

PubMed

Yoon, Jeong Hoon; Lim, Hyo Jin; Lee, Hwa Jin; Kim, Hee-Doo; Jeon, Raok; Ryu, Jae-Ha

2008-03-15

Three sesquiterpenoids, xanthatin (1), xanthinosin (2), and 4-oxo-bedfordia acid (3) were isolated from Xanthium strumarium as inhibitors of nitric oxide synthesis in activated microglia (IC(50) values: 0.47, 11.2, 136.5 microM, respectively). Compounds 1 and 2 suppressed the expression of iNOS and COX-2 and the activity of NF-kappaB through the inhibition of LPS-induced I-kappaB-alpha degradation in microglia.

Colletotrichine B, a new sesquiterpenoid from Colletotrichum gloeosporioides GT-7, a fungal endophyte of Uncaria rhynchophylla.

PubMed

Chen, Xiao-Wei; Yang, Zhong-Duo; Li, Xiao-Fei; Sun, Jian-Hui; Yang, Li-Jun; Zhang, Xin-Guo

2018-02-08

One new compound, colletotrichine B (1), was produced by the fungal Colletotrichum gloeosporioides GT-7. The structure of 1 was elucidated on the basis of spectroscopic analysis and X-ray crystallographic analysis. Monoamine oxidase (MAO), acetylcholinesterase (AChE) and phosphoinositide 3-kinase (PI3Kα) inhibitory activity of 1 was also evaluated. Compound 1 showed only AChE inhibiting activity with IC 50 value of 38.0 ± 2.67 μg/mL.

Sesquiterpenoids isolated from the flower buds of Tussilago farfara L. inhibit diacylglycerol acyltransferase.

PubMed

Park, Hye Ran; Yoo, Mi Young; Seo, Jee Hee; Kim, Il Soon; Kim, Nam Ye; Kang, Ji Yun; Cui, Long; Lee, Chang-Soo; Lee, Chul-Ho; Lee, Hyun Sun

2008-11-26

Inhibition of acyl CoA:diacylglycerol acyltransferase (DGAT), which is a key enzyme in triglyceride synthesis in eukaryotic organisms, has been proposed as one of the drug targets for treating obesity, type II diabetes mellitus, and metabolic syndrome. Bioassay-guided fractionation of EtOH extract of the flower buds of Tussilago farfara , using an in vitro DGAT enzyme assay, resulted in the isolation of four known sesquiterpenoids, tussilagonone (1), tussilagone (2), 7beta-(3-ethyl-cis-crotonoyloxy)-1alpha-(2-methylbutyryloxy)-3,14-dehydro-Z-notonipetranone (3), and 8-angeloylxy-3,4-epoxy-bisabola-7(14),10-dien-2-one (4). DGAT1 inhibitory activity was studied by in vitro DGAT assay using rat liver microsomes and HepG2 cell microsomes. They showed DGAT1 inhibition with IC(50) values of 99.2 (1), 18.8 (2), 47.0 (3), and 211.1 (4) microM (for rat liver microsomes) and >1 mM (1), 49.1 (2), 160.7 (3), and 294.4 (4) microM (for HepG2 cell microsomes), respectively. Compound 2 showed the most potent inhibition against microsomal DGAT1 derived from rat liver and human hepatocellular carcinoma HepG2 cells and also significantly inhibited triglyceride synthesis by suppressing incorporation of [(14)C]acetate or [(14)C]glycerol into triglycerides in HepG2 cells. These findings suggest that tussilagone is a potential lead compound in the treatment of obesity and type 2 diabetes.

Regulation of Floral Terpenoid Emission and Biosynthesis in Sweet Basil (Ocimum basilicum).

PubMed

Jiang, Yifan; Ye, Jiayan; Li, Shuai; Niinemets, Ülo

2016-12-01

Past studies have focused on the composition of essential oil of Ocimum basilicum leaves, but data on composition and regulation of its aerial emissions, especially floral volatile emissions are scarce. We studied the chemical profile, within-flower spatial distribution (sepals, petals, pistils with stamina and pedicels), diurnal emission kinetics and effects of exogenous methyl jasmonate (MeJA) application on the emission of floral volatiles by dynamic headspace collection and identification using gas chromatography-mass spectrometry (GC-MS) and proton transfer reaction mass spectrometry (PTR-MS). We observed more abundant floral emissions from flowers compared with leaves. Sepals were the main emitters of floral volatiles among the flower parts studied. The emissions of lipoxygenase compounds (LOX) and monoterpenoids, but not sesquiterpene emissions, displayed a diurnal variation driven by light. Response to exogenous MeJA treatment of flowers consisted of a rapid stress response and a longer-term acclimation response. The initial response was associated with enhanced emissions of fatty acid derivatives, monoterpenoids, and sesquiterpenoids without variation of the composition of individual compounds. The longer-term response was associated with enhanced monoterpenoid and sesquiterpenoid emissions with profound changes in the emission spectrum. According to correlated patterns of terpenoid emission changes upon stress, highlighted by a hierarchical cluster analysis, candidate terpenoid synthases responsible for observed diversity and complexity of released terpenoid blends were postulated. We conclude that flower volatile emissions differ quantitatively and qualitatively from leaf emissions, and overall contribute importantly to O. basilicum flavor, especially under stress conditions.

Regulation of Floral Terpenoid Emission and Biosynthesis in Sweet Basil (Ocimum basilicum)

PubMed Central

Jiang, Yifan; Ye, Jiayan; Li, Shuai; Niinemets, Ülo

2018-01-01

Past studies have focused on the composition of essential oil of Ocimum basilicum leaves, but data on composition and regulation of its aerial emissions, especially floral volatile emissions are scarce. We studied the chemical profile, within-flower spatial distribution (sepals, petals, pistils with stamina and pedicels), diurnal emission kinetics and effects of exogenous methyl jasmonate (MeJA) application on the emission of floral volatiles by dynamic headspace collection and identification using gas chromatography-mass spectrometry (GC-MS) and proton transfer reaction mass spectrometry (PTR-MS). We observed more abundant floral emissions from flowers compared with leaves. Sepals were the main emitters of floral volatiles among the flower parts studied. The emissions of lipoxygenase compounds (LOX) and monoterpenoids, but not sesquiterpene emissions, displayed a diurnal variation driven by light. Response to exogenous MeJA treatment of flowers consisted of a rapid stress response and a longer-term acclimation response. The initial response was associated with enhanced emissions of fatty acid derivatives, monoterpenoids, and sesquiterpenoids without variation of the composition of individual compounds. The longer-term response was associated with enhanced monoterpenoid and sesquiterpenoid emissions with profound changes in the emission spectrum. According to correlated patterns of terpenoid emission changes upon stress, highlighted by a hierarchical cluster analysis, candidate terpenoid synthases responsible for observed diversity and complexity of released terpenoid blends were postulated. We conclude that flower volatile emissions differ quantitatively and qualitatively from leaf emissions, and overall contribute importantly to O. basilicum flavor, especially under stress conditions. PMID:29367803

A new diterpenoid glucoside and two new diterpenoids from the fruit of Vitex agnus-castus.

PubMed

Ono, Masateru; Eguchi, Keisuke; Konoshita, Masatarou; Furusawa, Chisato; Sakamoto, Junich; Yasuda, Shin; Ikeda, Tsuyoshi; Okawa, Masafumi; Kinjo, Junei; Yoshimitsu, Hitoshi; Nohara, Toshihiro

2011-01-01

A new labdane-type diterpenoid glucoside and two new labdane-type diterpenoids were isolated from the fruit (chasteberry) of Vitex agnus-castus L. (Verbenaceae) along with 14 known compounds comprising seven labdane-type diterpenoids, one halimane-type diterpenoid, two oleanane-type triterpenoids, two ursane-type triterpenoids, one aromadendrane-type sesquiterpenoid, and one flavonoid. Their structures were characterized on the basis of spectroscopic data as well as chemical evidence. Furthermore, the antioxidative activities of the flavonoid were evaluated using five different analyses.

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.

Cadinane sesquiterpenoids from the basidiomycete Stereum cf. sanguinolentum BCC 22926.

PubMed

Bunyapaiboonsri, Taridaporn; Yoiprommarat, Seangaroon; Nopgason, Rujirek; Komwijit, Somjit; Veeranondha, Sukitaya; Puyngain, Pucharapa; Boonpratuang, Thitiya

2014-09-01

Stereumins Q-U, together with known stereumins A, B, K, L, and N, as well as ent-strobilols E and G were isolated from the culture of Stereum cf. sanguinolentum BCC 22926. Their structures were elucidated by extensive spectroscopic analyses. The absolute configurations of stereumins A and Q, as well as ent-strobilol E were established by application of the modified Mosher's method. Stereumin T displayed antibacterial activity against Bacilluscereus with a MIC value of 3.97μM. Copyright © 2014 Elsevier Ltd. All rights reserved.

Isolation of cDNAs and functional characterisation of two multi-product terpene synthase enzymes from sandalwood, Santalum album L.

PubMed

Jones, Christopher G; Keeling, Christopher I; Ghisalberti, Emilio L; Barbour, Elizabeth L; Plummer, Julie A; Bohlmann, Jörg

2008-09-01

Sandalwood, Santalum album (Santalaceae) is a small hemi-parasitic tropical tree of great economic value. Sandalwood timber contains resins and essential oils, particularly the santalols, santalenes and dozens of other minor sesquiterpenoids. These sesquiterpenoids provide the unique sandalwood fragrance. The research described in this paper set out to identify genes involved in essential oil biosynthesis, particularly terpene synthases (TPS) in S. album, with the long-term aim of better understanding heartwood oil production. Degenerate TPS primers amplified two genomic TPS fragments from S. album, one of which enabled the isolation of two TPS cDNAs, SamonoTPS1 (1731bp) and SasesquiTPS1 (1680bp). Both translated protein sequences shared highest similarity with known TPS from grapevine (Vitis vinifera). Heterologous expression in Escherichia coli produced catalytically active proteins. SamonoTPS1 was identified as a monoterpene synthase which produced a mixture of (+)-alpha-terpineol and (-)-limonene, along with small quantities of linalool, myrcene, (-)-alpha-pinene, (+)-sabinene and geraniol when assayed with geranyl diphosphate. Sesquiterpene synthase SasesquiTPS1 produced the monocyclic sesquiterpene alcohol germacrene D-4-ol and helminthogermacrene, when incubated with farnesyl diphosphate. Also present were alpha-bulnesene, gamma-muurolene, alpha- and beta-selinenes, as well as several other minor bicyclic compounds. Although these sesquiterpenes are present in only minute quantities in the distilled sandalwood oil, the genes and their encoded enzymes described here represent the first TPS isolated and characterised from a member of the Santalaceae plant family and they may enable the future discovery of additional TPS genes in sandalwood.

Sesquiterpenoids in subtribe Centaureinae (Cass.) Dumort (tribe Cardueae, Asteraceae): distribution, (13)C NMR spectral data and biological properties.

PubMed

Bruno, Maurizio; Bancheva, Svetlana; Rosselli, Sergio; Maggio, Antonella

2013-11-01

Asteraceae Bercht. & J. Presl is one of the biggest and most economically important plant families. The taxonomy and phylogeny of Asteraceae is rather complex and according to the latest and most reliable taxonomic classification of Panero & Funk, based on the analysis of nine chloroplast regions, the family is divided into 12 subfamilies and 35 tribes. One of the largest tribes of Asteraceae is Cardueae Cass. with four subtribes (Carlininae, Echinopinae, Carduinae and Centaureinae) and more than 2500 species. Susanna & Garcia-Jacas have organized the genera of Centaureinae (about 800 species) into seven informal groups, which recent molecular studies have confirmed: 1. Basal genera; 2. Volutaria group; 3. Rhaponticum group; 4. Serratula group; 5. Carthamus group; 6. Crocodylium group; 7. Centaurea group. This review summarizes reports on sesquiterpenoids from the Centaureinae subtribe of the Asteraceae family, as well as the (13)C NMR spectral data described in the literature. It further reviews studies concerning the biological activities of these metabolites. For this work, literature data on sesquiterpenes from the Centaureinae subtribe were retrieved with the help of the SciFinder database and other similar data banks. All entries from 1958 until the end of 2011 were considered. This review is addressed to scientists working in the metabolomics field such as chemists, botanists, etc., the spectroscopic data reported make this work a good tool for structural elucidation, the biological section gives useful information to those who wish to study the structure activity relationships. Copyright © 2013 Elsevier Ltd. All rights reserved.

Attracting mutualists and antagonists: plant trait variation explains the distribution of specialist floral herbivores and pollinators on crops and wild gourds.

PubMed

Theis, Nina; Barber, Nicholas A; Gillespie, Sandra D; Hazzard, Ruth V; Adler, Lynn S

2014-08-01

• Floral traits play important roles in pollinator attraction and defense against floral herbivory. However, plants may experience trade-offs between conspicuousness to pollinators and herbivore attraction. Comparative studies provide an excellent framework to examine the role of multiple traits shaping mutualist and antagonist interactions.• To assess whether putative defensive and attractive traits predict species interactions, we grew 20 different Cucurbitaceae species and varieties in the field to measure interactions with pollinators and herbivores and in the greenhouse to assess trait variation. Cucurbits are characterized by the production of cucurbitacins, bitter nonvolatile terpenoids that are effective against generalist herbivores but can attract specialist beetles. We determined whether plant traits such as cucurbitacins predict herbivore resistance and pollinator attraction using an information-theoretic approach.• Mutualists and floral antagonists were attracted to the same cucurbit varieties once they flowered. However, rather than cucurbitacin concentration, we found that the size of the flower and volatile emissions of floral sesquiterpenoids explained both pollinator and floral herbivore visitation preference across cucurbit taxa. This pattern held across cucurbit taxa and within the Cucurbita genus.• Surprisingly, floral sesquiterpenoid volatiles, which are associated with direct defense, indirect defense, and attraction, rather than defense traits such as cucurbitacins, appeared to drive interactions with both pollinators and floral herbivores across cucurbit taxa. Identifying the relevant plant traits for attraction and deterrence is important in this economically valuable crop, particularly if pollinators and floral herbivores use the same plant traits as cues. © 2014 Botanical Society of America, Inc.

Abscisic acid negatively regulates elicitor-induced synthesis of capsidiol in wild tobacco.

PubMed

Mialoundama, Alexis Samba; Heintz, Dimitri; Debayle, Delphine; Rahier, Alain; Camara, Bilal; Bouvier, Florence

2009-07-01

In the Solanaceae, biotic and abiotic elicitors induce de novo synthesis of sesquiterpenoid stress metabolites known as phytoalexins. Because plant hormones play critical roles in the induction of defense-responsive genes, we have explored the effect of abscisic acid (ABA) on the synthesis of capsidiol, the major wild tobacco (Nicotiana plumbaginifolia) sesquiterpenoid phytoalexin, using wild-type plants versus nonallelic mutants Npaba2 and Npaba1 that are deficient in ABA synthesis. Npaba2 and Npaba1 mutants exhibited a 2-fold higher synthesis of capsidiol than wild-type plants when elicited with either cellulase or arachidonic acid or when infected by Botrytis cinerea. The same trend was observed for the expression of the capsidiol biosynthetic genes 5-epi-aristolochene synthase and 5-epi-aristolochene hydroxylase. Treatment of wild-type plants with fluridone, an inhibitor of the upstream ABA pathway, recapitulated the behavior of Npaba2 and Npaba1 mutants, while the application of exogenous ABA reversed the enhanced synthesis of capsidiol in Npaba2 and Npaba1 mutants. Concomitant with the production of capsidiol, we observed the induction of ABA 8'-hydroxylase in elicited plants. In wild-type plants, the induction of ABA 8'-hydroxylase coincided with a decrease in ABA content and with the accumulation of ABA catabolic products such as phaseic acid and dihydrophaseic acid, suggesting a negative regulation exerted by ABA on capsidiol synthesis. Collectively, our data indicate that ABA is not required per se for the induction of capsidiol synthesis but is essentially implicated in a stress-response checkpoint to fine-tune the amplification of capsidiol synthesis in challenged plants.

Advances in the Study of the Structures and Bioactivities of Metabolites Isolated from Mangrove-Derived Fungi in the South China Sea

PubMed Central

Wang, Xin; Mao, Zhi-Gang; Song, Bing-Bing; Chen, Chun-Hua; Xiao, Wei-Wei; Hu, Bin; Wang, Ji-Wen; Jiang, Xiao-Bing; Zhu, Yong-Hong; Wang, Hai-Jun

2013-01-01

Many metabolites with novel structures and biological activities have been isolated from the mangrove fungi in the South China Sea, such as anthracenediones, xyloketals, sesquiterpenoids, chromones, lactones, coumarins and isocoumarin derivatives, xanthones, and peroxides. Some compounds have anticancer, antibacterial, antifungal and antiviral properties, but the biosynthesis of these compounds is still limited. This review summarizes the advances in the study of secondary metabolites from the mangrove-derived fungi in the South China Sea, and their biological activities reported between 2008 and mid-2013. PMID:24084782

Chemical constituents and biological activities from branches of Colubrina asiatica.

PubMed

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

2018-05-01

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

Heartwood-specific transcriptome and metabolite signatures of tropical sandalwood (Santalum album) reveal the final step of (Z)-santalol fragrance biosynthesis.

PubMed

Celedon, Jose M; Chiang, Angela; Yuen, Macaire M S; Diaz-Chavez, Maria L; Madilao, Lufiani L; Finnegan, Patrick M; Barbour, Elizabeth L; Bohlmann, Jörg

2016-05-01

Tropical sandalwood (Santalum album) produces one of the world's most highly prized fragrances, which is extracted from mature heartwood. However, in some places such as southern India, natural populations of this slow-growing tree are threatened by over-exploitation. Sandalwood oil contains four major and fragrance-defining sesquiterpenols: (Z)-α-santalol, (Z)-β-santalol, (Z)-epi-β-santalol and (Z)-α-exo-bergamotol. The first committed step in their biosynthesis is catalyzed by a multi-product santalene/bergamotene synthase. Sandalwood cytochromes P450 of the CYP76F sub-family were recently shown to hydroxylate santalenes and bergamotene; however, these enzymes produced mostly (E)-santalols and (E)-α-exo-bergamotol. We hypothesized that different santalene/bergamotene hydroxylases evolved in S. album to stereo-selectively produce (E)- or (Z)-sesquiterpenols, and that genes encoding (Z)-specific P450s contribute to sandalwood oil formation if co-expressed in the heartwood with upstream genes of sesquiterpene biosynthesis. This hypothesis was validated by the discovery of a heartwood-specific transcriptome signature for sesquiterpenoid biosynthesis, including highly expressed SaCYP736A167 transcripts. We characterized SaCYP736A167 as a multi-substrate P450, which stereo-selectively produces (Z)-α-santalol, (Z)-β-santalol, (Z)-epi-β-santalol and (Z)-α-exo-bergamotol, matching authentic sandalwood oil. This work completes the discovery of the biosynthetic enzymes of key components of sandalwood fragrance, and highlights the evolutionary diversification of stereo-selective P450s in sesquiterpenoid biosynthesis. Bioengineering of microbial systems using SaCYP736A167, combined with santalene/bergamotene synthase, has potential for development of alternative industrial production systems for sandalwood oil fragrances. © 2016 The Authors The Plant Journal © 2016 John Wiley & Sons Ltd.

Reactive oxygen species and hormone signaling cascades in endophytic bacterium induced essential oil accumulation in Atractylodes lancea.

PubMed

Zhou, Jia-Yu; Li, Xia; Zhao, Dan; Deng-Wang, Meng-Yao; Dai, Chuan-Chao

2016-09-01

Pseudomonas fluorescens induces gibberellin and ethylene signaling via hydrogen peroxide in planta . Ethylene activates abscisic acid signaling. Hormones increase sesquiterpenoid biosynthesis gene expression and enzyme activity, inducing essential oil accumulation. Atractylodes lancea is a famous Chinese medicinal plant, whose main active components are essential oils. Wild A. lancea has become endangered due to habitat destruction and over-exploitation. Although cultivation can ensure production of the medicinal material, the essential oil content in cultivated A. lancea is significantly lower than that in the wild herb. The application of microbes as elicitors has become an effective strategy to increase essential oil accumulation in cultivated A. lancea. Our previous study identified an endophytic bacterium, Pseudomonas fluorescens ALEB7B, which can increase essential oil accumulation in A. lancea more efficiently than other endophytes; however, the underlying mechanisms remain unknown (Physiol Plantarum 153:30-42, 2015; Appl Environ Microb 82:1577-1585, 2016). This study demonstrates that P. fluorescens ALEB7B firstly induces hydrogen peroxide (H2O2) signaling in A. lancea, which then simultaneously activates gibberellin (GA) and ethylene (ET) signaling. Subsequently, ET activates abscisic acid (ABA) signaling. GA and ABA signaling increase expression of HMGR and DXR, which encode key enzymes involved in sesquiterpenoid biosynthesis, leading to increased levels of the corresponding enzymes and then an accumulation of essential oils. Specific reactive oxygen species and hormone signaling cascades induced by P. fluorescens ALEB7B may contribute to high-efficiency essential oil accumulation in A. lancea. Illustrating the regulation mechanisms underlying P. fluorescens ALEB7B-induced essential oil accumulation not only provides the theoretical basis for the inducible synthesis of terpenoids in many medicinal plants, but also further reveals the complex and diverse interactions among different plants and their endophytes.

Abscisic Acid Negatively Regulates Elicitor-Induced Synthesis of Capsidiol in Wild Tobacco1[W

PubMed Central

Mialoundama, Alexis Samba; Heintz, Dimitri; Debayle, Delphine; Rahier, Alain; Camara, Bilal; Bouvier, Florence

2009-01-01

In the Solanaceae, biotic and abiotic elicitors induce de novo synthesis of sesquiterpenoid stress metabolites known as phytoalexins. Because plant hormones play critical roles in the induction of defense-responsive genes, we have explored the effect of abscisic acid (ABA) on the synthesis of capsidiol, the major wild tobacco (Nicotiana plumbaginifolia) sesquiterpenoid phytoalexin, using wild-type plants versus nonallelic mutants Npaba2 and Npaba1 that are deficient in ABA synthesis. Npaba2 and Npaba1 mutants exhibited a 2-fold higher synthesis of capsidiol than wild-type plants when elicited with either cellulase or arachidonic acid or when infected by Botrytis cinerea. The same trend was observed for the expression of the capsidiol biosynthetic genes 5-epi-aristolochene synthase and 5-epi-aristolochene hydroxylase. Treatment of wild-type plants with fluridone, an inhibitor of the upstream ABA pathway, recapitulated the behavior of Npaba2 and Npaba1 mutants, while the application of exogenous ABA reversed the enhanced synthesis of capsidiol in Npaba2 and Npaba1 mutants. Concomitant with the production of capsidiol, we observed the induction of ABA 8′-hydroxylase in elicited plants. In wild-type plants, the induction of ABA 8′-hydroxylase coincided with a decrease in ABA content and with the accumulation of ABA catabolic products such as phaseic acid and dihydrophaseic acid, suggesting a negative regulation exerted by ABA on capsidiol synthesis. Collectively, our data indicate that ABA is not required per se for the induction of capsidiol synthesis but is essentially implicated in a stress-response checkpoint to fine-tune the amplification of capsidiol synthesis in challenged plants. PMID:19420326

Intraspecific variation in essential oil composition of the medicinal plant Lippia integrifolia (Verbenaceae). Evidence for five chemotypes.

PubMed

Marcial, Guillermo; de Lampasona, Marina P; Vega, Marta I; Lizarraga, Emilio; Viturro, Carmen I; Slanis, Alberto; Juárez, Miguel A; Elechosa, Miguel A; Catalán, César A N

2016-02-01

The aerial parts of Lippia integrifolia (incayuyo) are widely used in northwestern and central Argentina for their medicinal and aromatic properties. The essential oil composition of thirty-one wild populations of L. integrifolia covering most of its natural range was analyzed by GC and GC-MS. A total of one hundred and fifty two terpenoids were identified in the essential oils. Sesquiterpenoids were the dominant components in all but one of the collections analyzed, the only exception being a sample collected in San Juan province where monoterpenoids amounted to 51%. Five clearly defined chemotypes were observed. One possessed an exquisite and delicate sweet aroma with trans-davanone as dominant component (usually above 80%). Another with an exotic floral odour was rich in oxygenated sesquiterpenoids based on the rare lippifoliane and africanane skeletons. The trans-davanone chemotype is the first report of an essential oil containing that sesquiterpene ketone as the main constituent. The absolute configuration of trans-davanone from L. integrifolia was established as 6S, 7S, 10S, the enantiomer of trans-davanone from 'davana oil' (Artemisia pallens). Wild plants belonging to trans-davanone and lippifolienone chemotypes were propagated and cultivated in the same parcel of land in Santa Maria, Catamarca. The essential oil compositions of the cultivated plants were essentially identical to the original plants in the wild, indicating that the essential oil composition is largely under genetic control. Specimens collected near the Bolivian border that initially were identified as L. boliviana Rusby yielded an essential oil practically identical to the trans-davanone chemotype of L. integrifolia supporting the recent view that L. integrifolia (Gris.) Hieron. and L. boliviana Rusby are synonymous. Copyright © 2015 Elsevier Ltd. All rights reserved.

New sesquiterpenoids and a diterpenoid from Alpinia oxyphylla.

PubMed

Hou, Lei; Ding, Gang; Guo, Baolin; Huang, Wenhua; Zhang, Xiaojian; Sun, Zhiyong; Shi, Xiangfen

2015-01-16

The new compounds 2-methyl-6-isopropyl-7-hydroxymethyl naphthalene (1), oxyphyllenone H (2), epi-oxyphyllenone (6), (E)-labda-12,14-dien-15(16)-olide-17-oic acid (3), and two new natural products 4 and 5 were isolated from the ethyl acetate part of 95% ethanol extract of Alpinia oxyphylla, together with six known compounds 7-12. The inhibitory effects of compounds 1-12 on α-glucosidase were evaluated, and compounds 1, 3 and 6 showed moderate bioactive effect, with inhibitory rates of 10.3%, 10.0% and 11.5%, respectively, compared to the positive control acarbose (41.9%) at 20 µg/mL.

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).

Ganoderma pfeifferi--A European relative of Ganoderma lucidum.

PubMed

Lindequist, Ulrike; Jülich, Wolf-Dieter; Witt, Sabine

2015-06-01

In contrast to well-studied and broadly used Ganoderma species, such as Ganoderma lucidum and Ganoderma applanatum, knowledge regarding Ganoderma pfeifferi is very limited. Herein is an overview of the phytochemistry, biological activities and possible applications of this mushroom species. In addition to triterpenoids and polysaccharides, G. pfeifferi contains unique sesquiterpenoids and other small molecular weight compounds. Some of these compounds exhibit remarkable antimicrobial activities in vitro and in vivo against multi-resistant bacteria, such as MRSA. Antiviral properties, UV-protection abilities and other activities are also known. Potential issues arising from the conversion of research results into practical applications are discussed. Copyright © 2015 Elsevier Ltd. All rights reserved.

Smooth muscle relaxing flavonoids and terpenoids from Conyza filaginoides.

PubMed

Mata, R; Rojas, A; Acevedo, L; Estrada, S; Calzada, F; Rojas, I; Bye, R; Linares, E

1997-02-01

Activity-guided fractionation of the smooth muscle relaxing, chloroform-methanol (1:1) extract of Conyza filaginoides (D.C.) Hieron (Asteraceae) led to the isolation of three flavonoids (quercetin 3-glucoside, rutin, and pinostrobin), one sterol (alpha-spinasterol), a sesquiterpenoid (beta-caryophyllene 4,5-alpha-oxide), and two triterpenoids (erythrodiol and 3-beta-tridecanoyloxy-28-hydroxyolean-12-ene). 3-beta-Tridecanoyloxy-28-hydroxy-olean-12-ene is a new naturally occurring terpenoid. All the isolated compounds induced a concentration-dependent inhibition of the spontaneous contractions of rat ileum. The spasmolytic activity exhibited by the extract and active principles tends to support the traditional use of C filaginoides as an antispasmodic agent.

New sesquiterpenes, JBIR-27 and -28, isolated from a tunicate-derived fungus, Penicillium sp. SS080624SCf1.

PubMed

Motohashi, Keiichiro; Hashimoto, Junko; Inaba, Shigeki; Khan, Shams Tabrez; Komaki, Hisayuki; Nagai, Aya; Takagi, Motoki; Shin-ya, Kazuo

2009-05-01

In the course of our screening program for novel metabolites from tunicate-derived fungi, novel sesquiterpenoids, named JBIR-27 (1) and -28 (2), together with known sporogen-AO1 and phomenone, were isolated from the culture broth of Penicillium sp. SS080624SCf1. The structures of 1 and 2 were determined to be eremophilane analogs on the basis of extensive NMR and MS analyses. Sporogen-AO1, phomenone and 2 showed cytotoxicity against human cervical carcinoma cell line HeLa at IC(50) values of 8.3, 19 and 92 microM, respectively, whereas 1 was inactive at a concentration of 80 microM.

Comparative Study on Volatile Compounds of Alpinia japonica and Elettaria cardamomum.

PubMed

Asakawa, Yoshinori; Ludwiczuk, Agnieszka; Sakurai, Kazutoshi; Tomiyama, Kenichi; Kawakami, Yukihiro; Yaguchi, Yoshihiro

2017-08-01

The volatile compounds obtained from the ether extracts, headspace gases and steam distillates of Alpinia japonica and Elettaria cardamomum were analyzed by GC/MS. Both species were rich sources of naturally rare fenchane-type monoterpenoids, fenchene, fenchone, fenchyl alcohol and its acetate, together with 1,8-cineole. The distributions of volatile sesquiterpenoids were very poor in both species. Chiralities of fenchone in A. japonica and E. cardamomum were 99% of (1S,4R)-(+)-form. Camphor in A. japonica is composed of a mixture of (1R,4R)-(+)-form (94.3%) and (1S,4S)-(-)-form (5.7%). On the other hand, E. cardamomum produced only (1R,4R)-(+)-camphor (99%).

New skeletal sesquiterpenoids, caprariolides A-D, from Capraria biflora and their insecticidal activity.

PubMed

Collins, D O; Gallimore, W A; Reynolds, W F; Williams, L A; Reese, P B

2000-11-01

Four structurally novel isomeric sesquiterpenes have been isolated from the aerial parts of Capraria biflora. Caprariolides A (1), B (2), C (3), and D (4) have been determined by NMR spectroscopy experiments to be the (3S,5S,9R), (3R,5S,9R), (3R,5R,9R), and (3S,5R, 9R) isomers of 7-(furan-3'-yl)-3,9-dimethyl-1-oxaspiro[4. 5]dec-6-en-2-one, respectively. Both 1 and 2 were found to exhibit insecticidal activity against adult Cylas formicarius elegantulus, one of the most destructive insect pests of the sweet potato, Ipomoea sp.

Responses of the Housefly, Musca domestica, to the Hytrosavirus Replication: Impacts on Host's Vitellogenesis and Immunity

PubMed Central

Kariithi, Henry M.; Yao, Xu; Yu, Fahong; Teal, Peter E.; Verhoeven, Chelsea P.; Boucias, Drion G.

2017-01-01

Hytrosaviridae family members replicate in the salivary glands (SGs) of their adult dipteran hosts and are transmitted to uninfected hosts via saliva during feeding. Despite inducing similar gross symptoms (SG hypertrophy; SGH), hytrosaviruses (SGHVs) have distinct pathobiologies, including sex-ratio distortions in tsetse flies and refusal of infected housefly females to copulate. Via unknown mechanism(s), SGHV replication in other tissues results in reduced fecundity in tsetse flies and total shutdown of vitellogenesis and sterility in housefly females. We hypothesized that vitellogenesis shutdown was caused by virus-induced modulation of hormonal titers. Here, we used RNA-Seq to investigate virus-induced modulation of host genes/pathways in healthy and virus-infected houseflies, and we validated expression of modulated genes (n = 23) by RT-qPCR. We also evaluated the levels and activities of hemolymph AMPs, levels of endogenous sesquiterpenoids, and impacts of exogenous hormones on ovarian development in viremic females. Of the 973 housefly unigenes that were significantly modulated (padj ≤ 0.01, log2FC ≤ −2.0 or ≥ 2.0), 446 and 527 genes were downregulated and upregulated, respectively. While the most downregulated genes were related to reproduction (embryogenesis/oogenesis), the repertoire of upregulated genes was overrepresented by genes related to non-self recognition, ubiquitin-protease system, cytoskeletal traffic, cellular proliferation, development and movement, and snRNA processing. Overall, the virus, Musca domestica salivary gland hytrosavirus (MdSGHV), induced the upregulation of various components of the siRNA, innate antimicrobial immune, and autophagy pathways. We show that MdSGHV undergo limited morphogenesis in the corpora allata/corpora cardiaca (CA/CC) complex of M. domestica. MdSGHV replication in CA/CC potentially explains the significant reduction of hemolymph sesquiterpenoids levels, the refusal to mate, and the complete shutdown of egg development in viremic females. Notably, hormonal rescue of vitellogenesis did not result in egg production. The mechanism underlying MdSGHV-induced sterility has yet to be resolved. PMID:28424677

Identification and comparison of the volatile constituents of fresh and dried leaves of Spondias mombin found in North-central Nigeria: in vitro evaluation of their cytotoxic and antioxidant activities.

PubMed

Oladimeji, Abdulkabir Oladele; Aliyu, Medinat Bola; Ogundajo, Akintayo Lanre; Babatunde, Oluwatoyin; Adeniran, Oluremi Ishola; Balogun, Olaoye Solomon

2016-11-01

Various studies have shown that the leaf extracts of Spondias mombin Linn (Anacardiaceae) possess pharmacological properties such as antioxidant and antiviral effects. However, no biological activity from its essential oil has been reported in literature. To analyse the chemical constituents, cytotoxic activity and antioxidant capability of the essential oils from fresh and dried leaves of S. mombin. Hydrodistillation using Clevenger-type apparatus was employed to obtain the essential oil. Oil analysis was performed using an HP 6890 Gas Chromatograph coupled with an HP 5973 Mass Selective Detector. The cytotoxicity bioassay was carried out using the brine shrimp lethality test (10,000-0.01 μg/mL). Additionally, the reactive oxygen species scavenging potential of the two S. mombin oils (1000-200 μg/mL) were investigated using a hydroxyl radical scavenging and ferric iron reducing system. Chemical analysis of essential oils from S. mombin revealed the presence of 41 compounds, with predominance of monoterpenoids, sesquiterpenoids and non-terpenoids derivatives. In both fractions, the principal component was β-caryophellene (27.9-30.9%), followed by γ-cadinene (9.7-12.3%). There was an increase in the oxygenated monoterpenoid contents and a concomitant decrease in the amounts of sesquiterpenoids hydrocarbons observed on drying the leaves. The oil obtained from the fresh leaves was more active than that obtained from dried leaves, with LC 50 values (from the brine shrimp lethality assay) of 0.01 and 4.78 μg/mL, respectively. The two oils (from fresh and dried leaves) at 1.0 mg/mL scavenged hydroxyl radical by 83% and 99.8%, respectively. Moreover, they reduced ferric ion significantly and compared favourably with vitamin C. Essential oil derived from the leaves of S. mombin could hold promise for future application in the treatment of cancer-related diseases.

Sesquiterpenoids from the root of Panax Ginseng protect CCl4-induced acute liver injury by anti-inflammatory and anti-oxidative capabilities in mice.

PubMed

Wang, Weidong; Wang, Shijie; Liu, Jinping; Cai, Enbo; Zhu, Hongyan; He, Zhongmei; Gao, Yugang; Li, Pingya; Zhao, Yan

2018-06-01

The oxidative stress and inflammatory response play an important role in carbon tetracholoride (CCl 4 )-induced acute liver injury. In this work, sesquiterpenoids from the root of Panax Ginseng (SPG) were prepared, and then the hepatoprotective effects of SPG against CCl 4 -induced acute liver injury were investigated and the underlying mechanism was explored in mice. All mice were divided into four groups: the control, CCl 4 and SPG (2.5 and 10 mg/kg, dissolved in soybean oil, i.g.) groups. All mice were given continuous administration for 7 days, and injected with CCl 4 (0.1 mL/10 g body weight 0.2% CCl 4 solution in soybean oil, i.p.) 1 h after the end of the administration except the control group. Mice were sacrificed 24 h post-CCl 4 injection. The results indicated that SPG significantly reduced the increasement of serum AST and ALT levels induced by CCl 4 -treatment. And the histopathological analysis revealed that SPG treated mice had normal liver architecture and no necrosis. The decreased activities of SOD, GSH and CAT, and increased MDA level were inhibited by SPG treatment. At the same time, the levels of TNF-α, IL-1β and IL-6 were significantly decreased by SPG treatment. SPG treatment also reduced the heptic protein expressions of NF-κB p65, COX-2, MAPK p38, ERK and JNK in the liver. These fingdings demonstrated that SPG exhibited strong hepatoprective effect on the CCl 4 -induced acute liver injury, which was related to anti-oxidantive and anti-inflammatory capabilities; and the anti-inflammatory effect of SPG might mediated by the NF-κB and MAPKs signaling pathways. Taken together, SPG might be a potential material for drug and functional food development against chemical hepatic injury. Copyright © 2018. Published by Elsevier Masson SAS.

Neuroprotection against 6-OHDA toxicity in PC12 cells and mice through the Nrf2 pathway by a sesquiterpenoid from Tussilago farfara.

PubMed

Lee, Joohee; Song, Kwangho; Huh, Eugene; Oh, Myung Sook; Kim, Yeong Shik

2018-06-01

Oxidative stress plays a key role in neurodegenerative diseases such as Alzheimer's and Parkinson's diseases. Therefore, the nuclear factor-E2-related factor 2 (Nrf2), a key regulator of the antioxidative response, is considered to be important as a therapeutic target for neurodegenerative diseases. We investigated the underlying mechanism of Nrf2-mediated neuroprotective effects against oxidative stress in the PC12 cell line by 7β-(3-ethyl-cis-crotonoyloxy)-1α-(2-methylbutyryloxy)-3,14-dehydro-Z-notonipetranone (ECN), one of the sesquiterpenoids in Farfarae Flos. Pretreatment of PC12 cells with ECN had a protective effect against hydrogen peroxide (H 2 O 2 )- or 6-hydroxydopamine (6-OHDA)-induced cytotoxicity. ECN upregulated the ARE-luciferase activity and induced the mRNA expression of Nrf2 and antioxidant enzyme heme oxygenase-1 (HO-1). Knockdown of Nrf2 by small, interfering RNA (siRNA) abrogated the upregulation of HO-1, indicating that ECN had induced HO-1 via the Nrf2 pathway. Pretreatment with the thiol reducing agents, N-acetylcysteine (NAC) or dithiothreitol (DTT), attenuated Nrf2 activation and HO-1 expression. However, the non-thiol reducing antioxidant, Trolox, failed to inhibit HO-1 induction by ECN. These results suggest that ECN may directly interact with Kelch-like ECH-associated protein 1 (Keap1) and modify critical cysteine thiols present in the proteins responsible for Nrf2-mediated upregulation of HO-1. In a 6-OHDA-induced mouse model of PD, administration of ECN ameliorated motor impairments and dopaminergic neuronal damage. Taken together, ECN exerts neuroprotective effects by activating the Nrf2/HO-1 signaling pathway in both PC12 cells and mice. Thus, ECN, as an Nrf2 activator, could be an attractive therapeutic candidate for the neuroprotection or treatment of neurodegenerative diseases. Copyright © 2018 The Authors. Published by Elsevier B.V. All rights reserved.

Cyclic terpenoids of contemporary resinous plant detritus and of fossil woods, ambers and coals

USGS Publications Warehouse

Simoneit, B.R.T.; Grimalt, J.O.; Wang, T.-G.; Cox, R.E.; Hatcher, P.G.; Nissenbaum, A.

1986-01-01

Cyclic terpenoids present in the solvent extractable material of fossil woods, ambers and brown coals have been analyzed. The sample series chosen consisted of wood remains preserved in Holocene to Jurassic sediments and a set of of ambers from the Philippines (copalite), Israel, Canada and Dominican Republic. The brown coals selected were from the Fortuna Garsdorf Mine and Miocene formations on Fiji. The fossil wood extracts contained dominant diterpenoid or sesquiterpenoid skeletons, and aromatized species were present at high concentrations, with a major amount of two-ring aromatic compounds. Tricyclic diterpenoids were the predominant compounds in the ambers. Aromatized derivatives were the major components, consisting of one or two aromatic ring species with the abietane and occasionally pimarane skeletons. The saturated structures were comprised primarily of the abietane and pimarane skeletons having from three to five carbon (C1, C2, etc.) substituents. Kaurane and phyllocladane isomers were present in only minor amounts. Bicyclic sesquiterpenoids as saturated and partial or fully aromatized forms were also common in these samples, but only traces of sesterterpenoids and triterpenoid derivatives were found. The brown coal extracts were composed of major amounts of one- and two-ring aromatized terpenoids, with a greater proportion of triterpenoid derivatives than in the case of the woods and ambers. This was especially noticeable for the German coal, where the triterpenoids were predominant. Open C-ring aromatized structures were also present in this coal. Steroid compounds were not detectable, but some hopanes were found as minor components in the German brown coal. An overview of the skeletal structure classes identified in each sample, as well as the general mass spectrometric characteristics of the unknown compounds are included in the present paper. It can be concluded from these structural distributions that aromatization is the main process for the transformation of terrestrial cyclic terpenoids during diagenesis, constituting a general pathway for all terpenoids. ?? 1986 Pergamon Journals Ltd.

Search for β-Secretase Inhibitors from Natural Spices.

PubMed

Matsumura, Shinichi; Murata, Kazuya; Yoshioka, Yuri; Matsuda, Hideaki

2016-04-01

The growing number of Alzheimer's disease (AD) patients prompted us to seek effective natural resources for the prevention of AD. We focused on the inhibition of β-secretase, which is known to catalyze the production of senile plaque. Sixteen spices used in Asian countries were selected for the screening. Among the extracts tested, hexane extracts obtained from turmeric, cardamom, long pepper, cinnamon, Sichuan pepper, betel, white turmeric and aromatic ginger showed potent inhibitory activities. Their active principles were identified as sesquiterpenoids, monoterpenoids, fatty acid derivatives and phenylpropanoids using GC-MS analyses. The chemical structures and IC50 values of the compounds are disclosed. The results suggest that long-term consumption'of aromatic compounds from spices could be effective in the prevention of AD.

Effect of Soil Nutrient on Production and Diversity of Volatile Terpenoids from Plants

PubMed Central

Ormeño, E; Fernandez, C

2012-01-01

Terpenoid production (emission and storage) within foliage plays direct and indirect defensive and protective functions for the plant, mediates complex trophic relationships and controls the oxidation capacity of the atmosphere. Both biotic and abiotic conditions alter terpenoid production, with herbivory, light and temperature effects being reasonably well understood. In this manuscript, the state of the science about nutrient effect on terpenoid production is reviewed. The focus is on isoprene emissions and mono- and sesquiterpenoid emissions and concentrations according to fertilizing treatments and their potential interaction with other environmental factors. Ecological, physiological, biochemical and biophysical hypothesis formulated over research investigations are exposed and several points are highlighted as future research perspectives which could help to elucidate the apparent contrasting results. PMID:23097639

NO inhibitory constituents as potential anti-neuroinflammatory agents for AD from Blumea balsamifera.

PubMed

Ma, Jun; Ren, Quanhui; Dong, Bangjian; Shi, Zhaoyu; Zhang, Jie; Jin, Da-Qing; Xu, Jing; Ohizumi, Yasushi; Lee, Dongho; Guo, Yuanqiang

2018-02-01

Our continuous search for new nitric oxide (NO) inhibitory substances as anti-neuroinflammatory agents for AD resulted in the isolation of one new labdane diterpenoid and three new guaiane sesquiterpenoids, as well as ten known compounds from Blumea balsamifera. Their structures were elucidated by NMR spectroscopic data analysis and the time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculations. The anti-neuroinflammatory effects were examined by inhibiting NO release in LPS-induced murine microglial BV-2 cells. The possible mechanism of NO inhibition of some bioactive compounds was also investigated using molecular docking, which revealed the interactions of bioactive compounds with the iNOS protein. Copyright © 2017 Elsevier Inc. All rights reserved.

Thrombosis and systemic and cardiac oxidative stress and DNA damage induced by pulmonary exposure to diesel exhaust particles and the effect of nootkatone thereon.

PubMed

Nemmar, Abderrahim; Al-Salam, Suhail; Beegam, Sumaya; Yuvaraju, Priya; Ali, Badreldin H

2018-05-01

Adverse cardiovascular effects of particulate air pollution persist even at lower concentrations than those of the current air quality limit. Therefore, identification of safe and effective measures against particle-induced cardiovascular toxicity is needed. Nootkatone is a sesquiterpenoid in grapefruit with diverse bioactivities including anti-inflammatory and antioxidant effects. However, its protective effect on the cardiovascular injury induced by diesel exhaust particles (DEPs) has not been studied before. We assessed the possible protective effect of nootkatone (90 mg/kg) administered by gavage 1 h before intratracheal instillation of DEPs (30 μg/mouse). Twenty-four hours after the intratracheal administration of DEPs, various thrombotic and cardiac parameters were assessed. Nootkatone inhibited the prothrombotic effect induced by DEPs in pial arterioles and venules in vivo and platelet aggregation in whole blood in vitro. Also, nootkatone prevented the shortening of activated partial thromboplastin time and prothrombin time induced by DEPs. Nootkatone inhibited the increase of plasma concentration of fibrinogen, plasminogen activator inhibitor-1, interleukin-6, and lipid peroxidation induced by DEPs. Immunohistochemically, hearts showed an analogous increase in glutathione and nuclear factor erythroid-derived 2-like 2 expression by cardiac myocytes and endothelial cells after DEP exposure, and these effects were enhanced in mice treated with nootkatone + DEPs. Likewise, heme oxygenase-1 was increased in mice treated with nootkatone + DEPs compared with those treated with DEPs or nootkatone + saline. The DNA damage caused by DEPs was prevented by nootkatoone pretreatment. In conclusion, nootkatoone alleviates DEP-induced thrombogenicity and systemic and cardiac oxidative stress and DNA damage, at least partly, through nuclear factor erythroid-derived 2-like 2 and heme oxygenase-1 activation. NEW & NOTEWORTHY Nootkatoone, a sesquiterpenoid found in grapefruit, alleviates the thrombogenicity and systemic and cardiac oxidative stress and DNA damage in mice exposed to diesel exhaust particles. Nootkatone-induced boosting of nuclear factor erythroid-derived 2-like 2 and heme oxygenase-1 levels in the heart of mice exposed to diesel exhaust particles suggests that its protective effect is, at least partly, mediated through nuclear factor erythroid-derived 2-like 2 and heme oxygenase-1 activation.

HPLC-MS and GC-MS analyses combined with orthogonal partial least squares to identify cytotoxic constituents from turmeric (Curcuma longa L.).

PubMed

Jiang, Jianlan; Zhang, Huan; Li, Zidan; Zhang, Xiaohang; Su, Xin; Li, Yan; Qiao, Bin; Yuan, Yingjin

2013-08-01

We investigated the fingerprints of 48 batches of turmeric total extracts (TTE) by HPLC-MS-MS and GC-MS analyses and 43 characteristic peaks (22 constituents from HPLC-MS-MS; 21 from GC-MS) were analyzed qualitatively and quantitatively. An MTT {3-(4,5-dimethylthiazol-2-yl)- 2,5-diphenyltetrazolium bromide} assay was implemented to measure the cytotoxicity of the TTE against HeLa cells. Then we utilized orthogonal partial least squares analysis, which correlated the chemical composition of the TTE to its cytotoxic activity, to identify potential cytotoxic constituents from turmeric. The result showed that 19 constituents contributed significantly to the cytotoxicity. The obtained result was verified by canonical correlation analysis. Comparison with previous reports also indicated some interaction between the curcuminoids and sesquiterpenoids in turmeric.

Constituents of Senecio chionophilus with potential antitubercular activity.

PubMed

Gu, Jian-Qiao; Wang, Yuehong; Franzblau, Scott G; Montenegro, Gloria; Timmermann, Barbara N

2004-09-01

Two new sesquiterpenoids, (1S,4S,5R,10R)-1-hydroxy-6-isobutyryloxy-10H-9-oxofuranoeremophilane (1) and 1alpha-hydroxy-6beta-(2xi-methylbutyryloxy)-10alphaH-9-oxofuranoeremophilane (2), along with 21 known constituents, were isolated from the n-hexane and dichloromethane extracts of the above-ground biomass and roots of Senecio chionophilus. The structures of 1 and 2 were elucidated on the basis of spectroscopic evidence and chemical transformation methods. The absolute configuration of 1 was determined by Mosher ester methodology. All of the isolates were evaluated for their antitubercular potential against Mycobacterium tuberculosis in a microplate Alamar Blue assay. Compound 2, 6beta-angeloyloxy-1alpha-hydroxy-10alphaH-9-oxofuranoeremophilane (3), and 4'-hydroxyacetophenone (6) exhibited mild antitubercular activity at minimum inhibitory concentrations of 119, 114, and 121 microg/mL, respectively.

Unravelling Photochemical Relationships Among Natural Products from Aplysia dactylomela

PubMed Central

2016-01-01

Aplydactone (1) is a brominated ladderane sesquiterpenoid that was isolated from the sea hare Aplysia dactylomela together with the chamigranes dactylone (2) and 10-epi-dactylone (3). Given the habitat of A. dactylomela, it seems likely that 1 is formed from 2 through a photochemical [2 + 2] cycloaddition. Here, we disclose a concise synthesis of 1, 2, and 3 that was guided by excited state theory and relied on several highly stereoselective transformations. Our experiments and calculations confirm the photochemical origin of 1 and explain why it is formed as the sole isomer. Irradiation of 3 with long wavelength UV light resulted in a [2 + 2] cycloaddition that proceeded with opposite regioselectivity. On the basis of this finding, it seems likely that the resulting regioisomer, termed “8-epi-isoaplydactone”, could also be found in A. dactylomela. PMID:28149951

Effects of alismol isolated from Alismatis Rhizoma on calcium-induced contraction in the rabbit thoracic aorta

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

Matsuda, H.; Kobayashi, G.; Yamahara, J.

1987-10-12

The authors examined the inhibitory effects of alismol, a sesquiterpenoid isolated from Alismatis Rhizoma, on vascular contractions induced by high concentrations of K/sup +/ and Ca/sup 2 +/, and on /sup 45/Ca/sup 2 +/ retention in normal and in high K/sup +/-containing medium. Alismol affected neither the resting tension nor the /sup 45/Ca/sup 2 +/ retention in normal medium, but it inhibited sustained contraction and increased /sup 45/Ca/sup 2 +/ retention induced by high K/sup +/ concentrations. Alismol did not affect norepinephrine-induced contractions in normal medium, nor phasic contractions in Ca/sup 2 +/-free medium. These results suggested that alismol inhibitedmore » mainly Ca/sup 2 +/ influx through a voltage-dependent Ca/sup 2 +/ channel. 19 references, 6 figures.« less

Four new sesquiterpenes from the rhizomes of Curcuma phaeocaulis and their iNOS inhibitory activities.

PubMed

Ma, Jiang-Hao; Wang, Ying; Liu, Yue; Gao, Su-Yu; Ding, Li-Qin; Zhao, Feng; Chen, Li-Xia; Qiu, Feng

2015-05-01

Three new guaiane-type sesquiterpenes named phaeocaulisins K-M (1-3), and one germacrane-type sesquiterpenoid with new ring system of 1,5- and 1,8-ether groups named phagermadiol (4), were isolated from rhizomes of Curcuma phaeocaulis. Their structures were established based on extensive spectroscopic analysis. Compound 1, the first example of norsesquiterpene with tropone backbone, and compound 3 with a novel 1,2-dioxolane sesquiterpene alcohol were isolated from the genus Curcuma. All of the isolated compounds were tested for inhibitory activity against lipopolysaccharide-induced nitric oxide (NO) production in RAW 264.7 macrophages. Compound 3 inhibited NO production with IC50 value of 6.05 ± 0.43 μM. The plausible biosynthetic pathway for compounds 3 and 4 in C. phaeocaulis was also discussed.

A cadinene biopolymer in fossil and extant dammar resins as a source for cadinanes and bicadinanes in crude oils from South East Asia

NASA Astrophysics Data System (ADS)

Van Aarssen, B. G. K.; Cox, H. C.; Hoogendoorn, P.; De Leeuw, J. W.

1990-11-01

The chemical composition of a fossil resin from a Miocene outcrop in Brunei, South East Asia, is compared with its extant counterpart dammar, obtained from trees of the family Dipterocarpaceae, to establish the nature of the precursor of bicadinanes. The alcohol soluble fractions of the resins consist of functionalised triterpenoids and a small amount of sesquiterpenoids. None of the compounds present in this fraction bears any structural relation to bicadinanes. The alcohol insoluble fractions of the resins consist of a polymer based on cadinene. A structure for this polymer is proposed. Heating the polymer in dammar resin resulted in the formation of monomeric, dimeric, and trimeric cadinenes. It is thought that the naturally occurring bicadinanes result from dimeric cadinenes upon cyclisation.

An In-Silico Investigation of Phytochemicals as Antiviral Agents Against Dengue Fever.

PubMed

Powers, Chelsea N; Setzer, William N

2016-01-01

A virtual screening analysis of our library of phytochemical structures with dengue virus protein targets has been carried out using a molecular docking approach. A total of 2194 plant-derived secondary metabolites have been docked. This molecule set comprised of 290 alkaloids (68 indole alkaloids, 153 isoquinoline alkaloids, 5 quinoline alkaloids, 13 piperidine alkaloids, 14 steroidal alkaloids, and 37 miscellaneous alkaloids), 678 terpenoids (47 monoterpenoids, 169 sesquiterpenoids, 265 diterpenoids, 81 steroids, and 96 triterpenoids), 20 aurones, 81 chalcones, 349 flavonoids, 120 isoflavonoids, 74 lignans, 58 stilbenoids, 169 miscellaneous polyphenolic compounds, 100 coumarins, 28 xanthones, 67 quinones, and 160 miscellaneous phytochemicals. Dengue virus protein targets examined included dengue virus protease (NS2B-NS3pro), helicase (NS3 helicase), methyltransferase (MTase), RNA-dependent RNA polymerase (RdRp), and the dengue virus envelope protein. Polyphenolic compounds, flavonoids, chalcones, and other phenolics were the most numerous of the strongly docking ligands for dengue virus protein targets.

A novel diarylheptanoid-bearing sesquiterpene moiety from the rhizomes of Alpinia officinarum.

PubMed

Wei, Na; Zhou, Zhonglin; Wei, Qing; Wang, Yong; Jiang, Jun; Zhang, Junqing; Wu, Lixiang; Dai, Shuiping; Li, Youbin

2016-10-01

A new diarylheptanoid analogue-bearing sesquiterpene moiety, named Alpinisin A, was isolated from the rhizomes of Alpinia officinarum Hance. The new structure was determined by various spectroscopic techniques (1)H-nuclear magnetic resonance ((1)H NMR), (13)C-attached proton test ((13)C-APT), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC), (1)H-(1)H correlation spectroscopy ((1)H-(1)HCOSY), nuclear overhauser effect spectroscopy (NOESY) and high resolution electrospray ionization mass spectrometry (HR-ESI-MS). The compound was tested for cytotoxic activity in vitro against human tumour cell lines (gastric carcinoma cell -7901 (SGC-7901), Michigan Cancer Foundation-7 (MCF-7) and Caski), which showed significant inhibitory effects with IC50 levels of 11.42, 15.14 and 14.78 μM, respectively. The novel chemical structure characterised with a diarylheptanoid linked to a chain-like sesquiterpenoid should be highlighted.

Noncariogenic intense natural sweeteners.

PubMed

Kinghorn, A D; Kaneda, N; Baek, N I; Kennelly, E J; Soejarto, D D

1998-09-01

There is a definite relationship between the dietary consumption of sucrose and the incidence of dental caries. Noncaloric sucrose substitutes for use in the sweetening of foods, beverages, and medicines may be either synthetic compounds or natural products. In the United States, four potently sweet artificial sweeteners are approved, namely, saccharin, aspartame, acesulfame potassium, and sucralose. Highly sweet plant constituents are used in Japan and some other countries, including the diterpene glycoside stevioside and the protein thaumatin. Recent progress in a research project oriented towards the discovery and evaluation of novel potentially noncariogenic sweeteners from plants has focused on substances in the sesquiterpenoid, diterpenoid, triterpenoid, steroidal saponin, and proanthocyanidin structural classes. The feasibility of using Mongolian gerbil electrophysiological and behavioral assays to monitor the sweetness of plant extracts, chromatographic fractions, and pure isolates has been investigated. An in vivo cariogenicity study on the commercially available natural sweeteners stevioside and rebaudioside A has been carried out.

Study on the composition of the volatile fraction of Hamamelis virginiana.

PubMed

Engel, R; Gutmann, M; Hartisch, C; Kolodziej, H; Nahrstedt, A

1998-04-01

The volatile fractions, obtained by water distillation from the leaves and bark of Hamamelis virginiana L. were analysed in detail by GC-MS. About 175 (leaves) and 168 (bark) compounds have been identified or at least partly characterized on the basis of a computerized database (SeKoMS). The dominating substances were represented by a homologous series of alkanes, alkenes, aliphatic alcohols, related aldehydes, ketones, and fatty acid esters. Importantly, significant differences in the terpenoid and phenylpropanoid patterns of the products obtained from the bark and leaves are apparent: whereas the product of bark distillation was found to typically contain phenylpropanoids and mainly sesquiterpenoids, that obtained from the leaves included some distinct monoterpenoids detected in comparably higher amounts. The chemical composition of the volatiles, when taken together with the absence of specific accumulation sites of lipophilics, emphasizes the definition "volatile fraction" rather than "essential oil".

Cnidarians as a Source of New Marine Bioactive Compounds—An Overview of the Last Decade and Future Steps for Bioprospecting

PubMed Central

Rocha, Joana; Peixe, Luisa; Gomes, Newton C.M.; Calado, Ricardo

2011-01-01

Marine invertebrates are rich sources of bioactive compounds and their biotechnological potential attracts scientific and economic interest worldwide. Although sponges are the foremost providers of marine bioactive compounds, cnidarians are also being studied with promising results. This diverse group of marine invertebrates includes over 11,000 species, 7500 of them belonging to the class Anthozoa. We present an overview of some of the most promising marine bioactive compounds from a therapeutic point of view isolated from cnidarians in the first decade of the 21st century. Anthozoan orders Alcyonacea and Gorgonacea exhibit by far the highest number of species yielding promising compounds. Antitumor activity has been the major area of interest in the screening of cnidarian compounds, the most promising ones being terpenoids (monoterpenoids, diterpenoids, sesquiterpenoids). We also discuss the future of bioprospecting for new marine bioactive compounds produced by cnidarians. PMID:22073000

Metabolic fingerprinting of Cannabis sativa L., cannabinoids and terpenoids for chemotaxonomic and drug standardization purposes.

PubMed

Fischedick, Justin Thomas; Hazekamp, Arno; Erkelens, Tjalling; Choi, Young Hae; Verpoorte, Rob

2010-12-01

Cannabis sativa L. is an important medicinal plant. In order to develop cannabis plant material as a medicinal product quality control and clear chemotaxonomic discrimination between varieties is a necessity. Therefore in this study 11 cannabis varieties were grown under the same environmental conditions. Chemical analysis of cannabis plant material used a gas chromatography flame ionization detection method that was validated for quantitative analysis of cannabis monoterpenoids, sesquiterpenoids, and cannabinoids. Quantitative data was analyzed using principal component analysis to determine which compounds are most important in discriminating cannabis varieties. In total 36 compounds were identified and quantified in the 11 varieties. Using principal component analysis each cannabis variety could be chemically discriminated. This methodology is useful for both chemotaxonomic discrimination of cannabis varieties and quality control of plant material. Copyright © 2010 Elsevier Ltd. All rights reserved.

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.

[Exploring pharmacological principle of Artemisia carvifolia with textmining technology].

PubMed

Zhao, Yu-Ping; Wang, Hui; Yang, Guang; Qiu, Zhi-Dong; Qu, Xiao-Bo; Zhang, Xiao-Bo

2016-08-01

To explore the pharmacological principle of Artemisia carvifolia,the text mining technique was used. All the references of A. carvifolia were collected from PubMed database, and then the rules of the main ingredient,relative diseases, organs, tissues, proteins and metabolites were analyzed. Finally, a network was set up. Then it was found that the main ingredients included sesquiterpenoids,flavonoids,and volatileoils.The diseases such as malaria, cerebral malaria, falciparum malaria, visceral leishmaniasis and systemic lupus erythematosus were often treated with A. carvifolia. In association in organ were the liver, skin, trachea,lungs,and spleen.Correlations with tissues were mainly including macrophages, T lymphocytes, blood vessels, epithelial cells.The protein was correlation with it involved CYP450, PI3K, TNF-α, AASDPPT, DNA polymerase and so on. Comprehensive and systematic treatment principle of A. carvifolia was obtained by text mining, which was helpful in clinical application. Copyright© by the Chinese Pharmaceutical Association.

Solanum torvum responses to the root-knot nematode Meloidogyne incognita

PubMed Central

2013-01-01

Background Solanum torvum Sw is worldwide employed as rootstock for eggplant cultivation because of its vigour and resistance/tolerance to the most serious soil-borne diseases as bacterial, fungal wilts and root-knot nematodes. The little information on Solanum torvum (hereafter Torvum) resistance mechanisms, is mostly attributable to the lack of genomic tools (e.g. dedicated microarray) as well as to the paucity of database information limiting high-throughput expression studies in Torvum. Results As a first step towards transcriptome profiling of Torvum inoculated with the nematode M. incognita, we built a Torvum 3’ transcript catalogue. One-quarter of a 454 full run resulted in 205,591 quality-filtered reads. De novo assembly yielded 24,922 contigs and 11,875 singletons. Similarity searches of the S. torvum transcript tags catalogue produced 12,344 annotations. A 30,0000 features custom combimatrix chip was then designed and microarray hybridizations were conducted for both control and 14 dpi (day post inoculation) with Meloidogyne incognita-infected roots samples resulting in 390 differentially expressed genes (DEG). We also tested the chip with samples from the phylogenetically-related nematode-susceptible eggplant species Solanum melongena. An in-silico validation strategy was developed based on assessment of sequence similarity among Torvum probes and eggplant expressed sequences available in public repositories. GO term enrichment analyses with the 390 Torvum DEG revealed enhancement of several processes as chitin catabolism and sesquiterpenoids biosynthesis, while no GO term enrichment was found with eggplant DEG. The genes identified from S. torvum catalogue, bearing high similarity to known nematode resistance genes, were further investigated in view of their potential role in the nematode resistance mechanism. Conclusions By combining 454 pyrosequencing and microarray technology we were able to conduct a cost-effective global transcriptome profiling in a non-model species. In addition, the development of an in silico validation strategy allowed to further extend the use of the custom chip to a related species and to assess by comparison the expression of selected genes without major concerns of artifacts. The expression profiling of S. torvum responses to nematode infection points to sesquiterpenoids and chitinases as major effectors of nematode resistance. The availability of the long sequence tags in S. torvum catalogue will allow precise identification of active nematocide/nematostatic compounds and associated enzymes posing the basis for exploitation of these resistance mechanisms in other species. PMID:23937585

Hypolipidemic and antioxidant activity of mountain celery (Cryptotaenia japonica Hassk) seed essential oils.

PubMed

Cheng, Ming-Ching; Lin, Li-Yun; Yu, Tung-Hsi; Peng, Robert Y

2008-06-11

Mountain celery seed essential oils (MC-E) contained 109 compounds, including mainly nine kinds of monoterpenoids, 31 kinds of of sesquiterpenoids, and 22 kinds of alcohols. A successive gel column adsorption with solvent fractionation yielded four fractionates. The pentane fractionate revealed potent hypolipidemic but poor antioxidant activities. The ether fractionate exhibited strong hypolipidemic activity in addition to excellent 1,1-diphenyl-2-picrylhydrazyl free radical- and superoxide anion-scavenging capabilities. The third acetone fractionate only showed moderate superoxide anion-scavenging activity. Finally, the fourth methanol fractionate having a rather high content of gamma-selinene, 2-methylpropanal, and Z-9-octadecenamide uniquely revealed very strong superoxide anion-scavenging capability. All MC diets except the MC-E-added diet simultaneously exhibited both significant hypolipidemic and high-density lipoprotein-cholesterol (HDL-C)-elevating capabilities. However, all diets totally failed to affect the hepatic phospholipid levels. Conclusively, the MC-E can be fractionated by such a separation technology to produce products uniquely possessing hypolipidemic and HDL-C-elevating activities.

Organic geochemical investigation and coal-bed methane characteristics of the Guasare coals (Paso Diablo mine, western Venezuela)

USGS Publications Warehouse

Quintero, K.; Martinez, M.; Hackley, P.; Marquez, G.; Garban, G.; Esteves, I.; Escobar, M.

2011-01-01

The aim of this work was to carry out a geochemical study of channel samples collected from six coal beds in the Marcelina Formation (Zulia State, western Venezuela) and to determine experimentally the gas content of the coals from the Paso Diablo mine. Organic geochemical analyses by gas chromatography-mass spectrometry and isotopic analyses on-line in coalbed gas samples were performed. The results suggest that the Guasare coals were deposited in a continental environment under highly dysoxic and low salinity conditions. The non-detection of 18??(H)-oleanane does not preclude that the organic facies that gave rise to the coals were dominated by angiosperms. In addition, the presence of the sesquiterpenoid cadalene may indicate the subordinate contribution of gymnosperms (conifers) in the Paleocene Guasare mire. The average coalbed gas content obtained was 0.6 cm3/g. ??13C and D values indicate that thermogenic gas is prevalent in the studied coals. Copyright ?? Taylor & Francis Group, LLC.

TLC-bioautographic evaluation of in vitro anti-tyrosinase and anti-cholinesterase potentials of sandalwood oil.

PubMed

Misra, Biswapriya B; Dey, Satyahari

2013-02-01

Sandalwood oil, rich in sesquiterpenoid alcohols, has been used in traditional medicinal systems as a relaxant and coolant. Besides, sandalwood oil is used as an ingredient in numerous skin fairness enhancing cosmetics. However, there is no available information on biological activities that relate to the above applications. Hence, the anti-tyrosinase and anti-cholinesterase potentials of sandalwood oil were probed by both TLC-bioautographic and colorimetric methods. Results obtained from colorimetric assays indicated that sandalwood oil is a potent inhibitor of tyrosinase (IC50 = 171 microg mL(-1)) and cholinesterases (IC50 = 4.8-58 microg mL(-1)), in comparison with the positive controls used in the assays, kojic acid and physostigmine, respectively. The TLC-bioautographic assays indicated that alpha-santalol, the major constituent of the oil, is a strong inhibitor of both tyrosinase and cholinesterase. These in vitro results indicate that there is a great potential of this essential oil for use in the treatment of Alzheimer's disease, as well as in skin-care.

An In-Silico Investigation of Phytochemicals as Antiviral Agents Against Dengue Fever

PubMed Central

Powers, Chelsea N.; Setzer, William N.

2016-01-01

Abstract: A virtual screening analysis of our library of phytochemical structures with dengue virus protein targets has been carried out using a molecular docking approach. A total of 2194 plant-derived secondary metabolites have been docked. This molecule set comprised of 290 alkaloids (68 indole alkaloids, 153 isoquinoline alkaloids, 5 quinoline alkaloids, 13 piperidine alkaloids, 14 steroidal alkaloids, and 37 miscellaneous alkaloids), 678 terpenoids (47 monoterpenoids, 169 sesquiterpenoids, 265 diterpenoids, 81 steroids, and 96 triterpenoids), 20 aurones, 81 chalcones, 349 flavonoids, 120 isoflavonoids, 74 lignans, 58 stilbenoids, 169 miscellaneous polyphenolic compounds, 100 coumarins, 28 xanthones, 67 quinones, and 160 miscellaneous phytochemicals. Dengue virus protein targets examined included dengue virus protease (NS2B-NS3pro), helicase (NS3 helicase), methyltransferase (MTase), RNA-dependent RNA polymerase (RdRp), and the dengue virus envelope protein. Polyphenolic compounds, flavonoids, chalcones, and other phenolics were the most numerous of the strongly docking ligands for dengue virus protein targets. PMID:27151482

The induction of mycotoxins by trichothecene producing Fusarium species.

PubMed

Lowe, Rohan; Jubault, Mélanie; Canning, Gail; Urban, Martin; Hammond-Kosack, Kim E

2012-01-01

In recent years, many Fusarium species have emerged which now threaten the productivity and safety of small grain cereal crops worldwide. During floral infection and post-harvest on stored grains the Fusarium hyphae produce various types of harmful mycotoxins which subsequently contaminate food and feed products. This article focuses specifically on the induction and production of the type B sesquiterpenoid trichothecene mycotoxins. Methods are described which permit in liquid culture the small or large scale production and detection of deoxynivalenol (DON) and its various acetylated derivatives. A wheat (Triticum aestivum L.) ear inoculation assay is also explained which allows the direct comparison of mycotoxin production by species, chemotypes and strains with different growth rates and/or disease-causing abilities. Each of these methods is robust and can be used for either detailed time-course studies or end-point analyses. Various analytical methods are available to quantify the levels of DON, 3A-DON and 15A-DON. Some criteria to be considered when making selections between the different analytical methods available are briefly discussed.

Remarkable preservation of terpenoids and record of volatile signalling in plant-animal interactions from Miocene amber.

PubMed

Dutta, Suryendu; Mehrotra, Rakesh C; Paul, Swagata; Tiwari, R P; Bhattacharya, Sharmila; Srivastava, Gaurav; Ralte, V Z; Zoramthara, C

2017-09-08

Plants produce and release a large array of volatile organic compounds that play many ecological functions. These volatile plant metabolites serve as pollinator attractants, herbivore and pathogen repellents and protect plants from abiotic stresses. To date, the geological evolution of these organic compounds remains unknown. The preservation potential of these metabolites in the fossil record is very poor due to their low boiling points. Here we report a series of volatile sesquiterpenoids, including δ-elemene, α-copaene, β-elemene, β-caryophyllene, α-humulene, germacrene D, δ-cadiene and spathunenol, from early Miocene (~17 million year) amber from eastern India. The survival of these unaltered bioterpenoids can be attributed to the existence of extraordinary taphonomic conditions conducive to the preservation of volatile biomolecules through deep time. Furthermore, the occurrence of these volatiles in the early Miocene amber suggests that the plants from this period had evolved metabolic pathways to synthesize these organic molecules to play an active role in forest ecology, especially in plant-animal interactions.

Characterization of Stevia leaves by LC-QTOF MS/MS analysis of polar and non-polar extracts.

PubMed

Molina-Calle, M; Priego-Capote, F; Luque de Castro, M D

2017-03-15

Stevia is currently a well-known plant thanks to its sweeting power. Numerous studies that elucidate its composition were exclusively focused on determination of steviol and its glycosides. Untargeted analysis was applied to obtain a profile of main compounds present in extracts from Stevia (Stevia rebaudiana Bertoni) leaves using LC-MS in high resolution mode with a quadrupole-time of flight analyzer. Eighty-nine compounds were tentatively identified and classified into different families: flavonoids; quinic and caffeic acids and derivatives; diterpenoids (including steviol and glycosides); sesquiterpenoids; amino acids and derivatives; fatty amides and derivatives; fatty acids and derivatives; oligosaccharides; glycerolipids; purines; and retinoids. New steviol glycosides were tentatively identified and their possible structures proposed. Other compounds were tentatively identified in Stevia for the first time, such as fatty acid amides. These results reveal the wide range of compounds present in Stevia, which could be responsible for the nutraceutical effects ascribed to their leaves. Copyright © 2016 Elsevier Ltd. All rights reserved.

Chemical composition and evaluation of antinociceptive activity of the essential oil of Stevia serrata Cav. from Guatemala.

PubMed

Reis Simas, Daniel Luiz; Mérida-Reyes, Max Samuel; Muñoz-Wug, Manuel Alejandro; Cordeiro, Millena Santos; Giorno, Thais Biondino Sardella; Taracena, Edwin Adolfo; Oliva-Hernández, Bessie Evelyn; Martínez-Arévalo, José Vicente; Fernandes, Patricia Dias; Pérez-Sabino, Juan Francisco; Jorge Ribeiro da Silva, Antonio

2017-11-13

The composition and the antinociceptive activity of the essential oil of Stevia serrata Cav. from a population located in the west highlands of Guatemala were evaluated. A yield of 0.2% (w/w) of essential oil was obtained by hydrodistillation of the dried aerial parts of the plant. The essential oil analysed by GC-FID and GC-MS showed a high content of sesquiterpenoids, with chamazulene (60.1%) as the major component and 91.5% of the essential oil composition was identified. To evaluate antinociceptive activity in mice, the essential oil of S. serrata Cav. was administered as gavage, using three different doses. In the formalin test, the animals were pre-treated with oral doses of the essential oil before the administration of formalin. Oral administration of S. serrata Cav. essential oil produced a marked antinociceptive activity. Therefore, the plant could be domesticated as a source of essential oil rich in chamazulene for developing medicinal products.

Effect of farnesol on structure and composition of Staphylococcus epidermidis biofilm matrix.

PubMed

Gomes, Fernanda; Teixeira, Pilar; Cerca, Nuno; Azeredo, Joana; Oliveira, Rosário

2011-10-01

Staphylococcus epidermidis is the most frequent cause of nosocomial sepsis and catheter-related infections in which biofilm formation is considered to be one of the main virulence mechanisms. Moreover, their increased resistance to conventional antibiotic therapy enhances the need to develop new therapeutical agents. Farnesol, a natural sesquiterpenoid present in many essential oils, has been described as impairing bacterial growth. The aim of this study was to evaluate the effect of farnesol on the structure and composition of biofilm matrix of S. epidermidis. Biofilms formed in the presence of farnesol (300 μM) contained less biomass, and displayed notable changes in the composition of the biofilm matrix. Changes in the spacial structure were also verified by confocal scanning laser microscopy (CSLM). The results obtained by the quantification of extracellular polymers and by wheat germ agglutinin (WGA) fluorescent detection of glycoproteins containing β(1→4)-N-acetyl-D: -glucosamine support the hypothesis that farnesol causes disruption of the cytoplasmic membrane and consequently release of cellular content.

Optimization by Molecular Fine Tuning of Dihydro-β-agarofuran Sesquiterpenoids as Reversers of P-Glycoprotein-Mediated Multidrug Resistance.

PubMed

Callies, Oliver; Sánchez-Cañete, María P; Gamarro, Francisco; Jiménez, Ignacio A; Castanys, Santiago; Bazzocchi, Isabel L

2016-03-10

P-glycoprotein (P-gp) plays a crucial role in the development of multidrug resistance (MDR), a major obstacle for successful chemotherapy in cancer. Herein, we report on the development of a natural-product-based library of 81 dihydro-β-agarofuran sesquiterpenes (2-82) by optimization of the lead compound 1. The compound library was evaluated for its ability to inhibit P-gp-mediated daunomycin efflux in MDR cells. Selected analogues were further analyzed for their P-gp inhibition constant, intrinsic toxicity, and potency to reverse daunomycin and vinblastine resistances. Analogues 6, 24, 28, 59, and 66 were identified as having higher potency than compound 1 and verapamil, a first-generation P-gp modulator. SAR analysis revealed the size of the aliphatic chains and presence of nitrogen atoms are important structural characteristics to modulate reversal activity. The present study highlights the potential of these analogues as modulators of P-gp mediated MDR in cancer cells.

Antiproliferative Compounds of Cyphostemma greveana from a Madagascar Dry Forest[1

PubMed Central

Cao, Shugeng; Hou, Yanpeng; Brodie, Peggy; Miller, James S.; Randrianaivo, Richard; Rakotobe, Etienne; Rasamison, Vincent E.

2011-01-01

Bioassay-guided fractionation of the EtOH extracts obtained from a plant identified as Cyphostemma greveana Desc. (Vitaceae) led to the identification of one macrolide, lasiodiplodin (1), three sesquiterpenoids, 12-hydroxy-15-oxo-selina-4,1l-diene (2), 1β,6α-dihydroxyeudesm-4(15)-ene (3), and (7R*)-opposit-4(15)-ene-1β,7-diol (5), and the new diterpenoid, 16,18-dihydroxykolavenic acid lactone (4). All the isolates were tested against the A2780 human ovarian cancer cell line, and compound 4 and a fraction containing 5 as the major constituent showed antiproliferative activities with IC50 values of 0.44 μM (0.14 μg/mL) and 0.045 μg/mL, respectively. A semisynthesis of compound 5 was carried out, but the pure synthetic compound was inactive, indicating that the activity of the fraction containing it must be due to a very minor and as yet unidentified substance. PMID:21480509

Antiproliferative compounds of Cyphostemma greveana from a Madagascar dry forest.

PubMed

Cao, Shugeng; Hou, Yanpeng; Brodie, Peggy; Miller, James S; Randrianaivo, Richard; Rakotobe, Etienne; Rasamison, Vincent E; Kingston, David G I

2011-04-01

Bioassay-guided fractionation of the EtOH extracts obtained from a plant identified as Cyphostemma greveana Desc. (Vitaceae) led to the identification of one macrolide, lasiodiplodin (1), three sesquiterpenoids, 12-hydroxy-15-oxoselina-4,11-diene (2), 1β,6α-dihydroxyeudesm-4(15)-ene (3), and (7R*)-opposit-4(15)-ene-1β,7-diol (5), and a new diterpenoid, 16,18-dihydroxykolavenic acid lactone (4). All the isolates were tested against the A2780 human ovarian cancer cell line, and compound 4 and a fraction containing 5 as the major constituent showed antiproliferative activities with IC(50) values of 0.44 μM (0.14 μg/ml) and 0.045 μg/ml, respectively. A partial synthesis of compound 5 was carried out, but the pure synthetic compound was inactive, indicating that the activity of the fraction containing it must be due to a very minor and as yet unidentified substance. Copyright © 2011 Verlag Helvetica Chimica Acta AG, Zürich.

Nootkatone encapsulation by cyclodextrins: Effect on water solubility and photostability.

PubMed

Kfoury, Miriana; Landy, David; Ruellan, Steven; Auezova, Lizette; Greige-Gerges, Hélène; Fourmentin, Sophie

2017-12-01

Nootkatone (NO) is a sesquiterpenoid volatile flavor, used in foods, cosmetics and pharmaceuticals, possessing also insect repellent activity. Its application is limited because of its low aqueous solubility and stability; this could be resolved by encapsulation in cyclodextrins (CDs). This study evaluated the encapsulation of NO by CDs using phase solubility studies, Isothermal Titration Calorimetry, Nuclear Magnetic Resonance spectroscopy and molecular modeling. Solid CD/NO inclusion complex was prepared and characterized for encapsulation efficiency and loading capacity using UV-Visible. Thermal properties were investigated by thermogravimetric-differential thermal analysis and release studies were performed using multiple headspace extraction. Formation constants (K f ) proved the formation of stable inclusion complexes. NO aqueous solubility, photo- and thermal stability were enhanced and the release could be insured from solid complex in aqueous solution. This suggests that CDs are promising carrier to improve NO properties and, consequently, to enlarge its use in foods, cosmetics, pharmaceuticals and agrochemicals preparations. Copyright © 2016 Elsevier Ltd. All rights reserved.

Perception of bitterness, sweetness and liking of different genotypes of lettuce.

PubMed

Chadwick, M; Gawthrop, F; Michelmore, R W; Wagstaff, C; Methven, L

2016-04-15

Lettuce is an important leafy vegetable, consumed across the world, containing bitter sesquiterpenoid lactone (SL) compounds that may negatively affect consumer acceptance and consumption. We assessed liking of samples with differing absolute abundance and different ratios of bitter:sweet compounds by analysing recombinant inbred lines (RILs) from an interspecific lettuce mapping population derived from a cross between a wild (L. serriola acc. UC96US23) and domesticated lettuce (L. sativa, cv. Salinas). We found that the ratio of bitter:sweet compounds was a key determinant of bitterness perception and liking. We were able to demonstrate that SLs, such as 8-deoxylactucin-15-sulphate, contribute most strongly to bitterness perception, whilst 15-p-hydroxylphenylacetyllactucin-8-sulphate does not contribute to bitter taste. Glucose was the sugar most highly correlated with sweetness perception. There is a genetic basis to the biochemical composition of lettuce. This information will be useful in lettuce breeding programmes in order to produce leaves with more favourable taste profiles. Copyright © 2015 Elsevier Ltd. All rights reserved.

Evaluation of antiplasmodial and antileishmanial activities of herbal medicine Pseudelephantopus spiralis (Less.) Cronquist and isolated hirsutinolide-type sesquiterpenoids.

PubMed

Girardi, Cynthia; Fabre, Nicolas; Paloque, Lucie; Ramadani, Arba Pramundita; Benoit-Vical, Françoise; González-Aspajo, German; Haddad, Mohamed; Rengifo, Elsa; Jullian, Valérie

2015-07-21

Pseudelephantopus spiralis (Less.) Cronquist is distributed in the Caribbean, Mesoamerica and Latin America. Preparations of the plant are traditionally used in Latin America for the treatment of various diseases including fever, malaria, and spleen or liver inflammations. Aerial parts of P. spiralis were extracted with either ethanol or distilled water. Seven hirsutinolide-type sesquiterpenoids were isolated: 8-acetyl-13-ethoxypiptocarphol (1), diacetylpiptocarphol (2), piptocarphins A (3), F (4) and D (5), (1S(*),4R(*),8S(*),10R(*))-1,4-epoxy-13-ethoxy-1,8,10-trihydroxygermacra-5E,7(11)-dien-6,12-olide (6), and piptocarphol (7). Extracts and isolated compounds (2, 3, 5-7) were screened for their in vitro antiplasmodial activity against the chloroquine-resistant Plasmodium falciparum strain FcM29-Cameroon and antileishmanial activity against three stages of Leishmania infantum. Their cytotoxicities were also evaluated against healthy VERO cell lines and J774A.1 macrophages, the host cells of the Leishmania parasites in humans. Aqueous extracts showed a greater inhibitory effect than alcoholic extracts, with IC50 on P. falciparum of 3.0µg/mL versus 21.1µg/mL, and on L. infantum of 13.4µg/mL versus >50µg/mL. Both extracts were found to be cytotoxic to VERO cells (CC50<3µg/mL). Sesquiterpene lactones 2 and 3 showed the best activity against both parasites but failed in selectivity. Carbon 8 hydroxylated hirsutinolides 5-7 presented the particularity of exhibiting two conformers observed in solution during extensive NMR analyses in CD3OD and UHPLC-MS. The presence of a hydroxyl function at C-8 decreased the activity of 5-7 on the two parasites and also on VERO cells. The antiplasmodial activity displayed by the aqueous extract explains the traditional use of P. spiralis in the treatment of malaria. This activity seems to be attributable to the presence of sesquiterpene lactones 2 and 3, the most active against P. falciparum. Aqueous extract and compounds 2, 3 and 6 were also active against L. infantum but lacked in selectivity due to their cytotoxicity towards macrophages. Exploring the safety and antiplasmodial efficacy of this traditional remedy will require further toxicological and in vivo studies in the light of the cytotoxicity towards healthy cell lines displayed by the aqueous extract and compounds 2 and 3. Copyright © 2015 Elsevier Ireland Ltd. All rights reserved.

New Metabolites and Bioactive Chlorinated Benzophenone Derivatives Produced by a Marine-Derived Fungus Pestalotiopsis heterocornis.

PubMed

Lei, Hui; Lin, Xiuping; Han, Li; Ma, Jian; Ma, Qingjuan; Zhong, Jialiang; Liu, Yonghong; Sun, Tiemin; Wang, Jinhui; Huang, Xueshi

2017-03-13

Four new compounds, including two isocoumarins, pestaloisocoumarins A and B ( 1 , 2 ), one sesquiterpenoid degradation, isopolisin B ( 4 ), and one furan derivative, pestalotiol A ( 5 ), together with one known isocoumarin, gamahorin ( 3 ), and three chlorinated benzophenone derivatives, pestalachloride B ( 6 ), pestalachloride E ( 7 ) and a mixture of pestalalactone atropisomers ( 8a/8b ), were isolated from a culture of the fungus Pestalotiopsis heterocornis associated with sponge Phakellia fusca . These new chemical structures were established using NMR and MS spectroscopic data, as well as single-crystal X-ray crystallographic analysis and CD Cotton effects. All of the isolated compounds were evaluated for their antimicrobial and cytotoxic activities. Isocoumarins 1 - 3 , showed antibacterial activities against Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis with MIC values ranging from 25 to 100 μg/mL and weak antifungal activities. Chlorinated benzophenone derivatives 6 - 8 exhibited antibacterial activities against S. aureus and B. subtilis with MIC values ranging from 3.0 to 50 μg/mL and cytotoxicities against four human cancer cell lines with IC 50 values of 6.8-87.8 μM.

Nerolidol effects on mitochondrial and cellular energetics.

PubMed

Ferreira, Fernanda M; Palmeira, Carlos M; Oliveira, Maria M; Santos, Dario; Simões, Anabela M; Rocha, Sílvia M; Coimbra, Manuel A; Peixoto, Francisco

2012-03-01

In the present work, we evaluated the potential toxic effects of nerolidol, a sesquiterpenoid common in plants essential oils, both on mitochondrial and cellular energetics. Samples of enriched natural extracts of nerolidol (a racemic mixture of cis and trans isomers) were tested on rat liver mitochondria and a decrease in phosphorylative system was observed but not in the mitochondrial respiratory chain activity, which reflects a direct effect on F1-ATPase. Hence, respiratory control ratio was also decreased. Cellular ATP/ADP levels were significantly decreased in a concentration-dependent manner, possibly due to the direct effect of nerolidol on F(0)F(1)-ATPsynthase. Nerolidol stimulates respiratory activity probably due to an unspecific effect, since it does not show any protonophoric effect. Furthermore, we observed that mitochondrial permeability transition was delayed in the presence of nerolidol, possibly due to its antioxidant activity and because this compound decreases mitochondrial transmembrane electric potential. Our results also show that, in human hepatocellular liver carcinoma cell line (HepG2), nerolidol both induces cell death and arrests cell growth, probably related with the observed lower bioenergetic efficiency. Copyright © 2011 Elsevier Ltd. All rights reserved.

Secondary Metabolites Produced during the Germination of Streptomyces coelicolor.

PubMed

Čihák, Matouš; Kameník, Zdeněk; Šmídová, Klára; Bergman, Natalie; Benada, Oldřich; Kofroňová, Olga; Petříčková, Kateřina; Bobek, Jan

2017-01-01

Spore awakening is a series of actions that starts with purely physical processes and continues via the launching of gene expression and metabolic activities, eventually achieving a vegetative phase of growth. In spore-forming microorganisms, the germination process is controlled by intra- and inter-species communication. However, in the Streptomyces clade, which is capable of developing a plethora of valuable compounds, the chemical signals produced during germination have not been systematically studied before. Our previously published data revealed that several secondary metabolite biosynthetic genes are expressed during germination. Therefore, we focus here on the secondary metabolite production during this developmental stage. Using high-performance liquid chromatography-mass spectrometry, we found that the sesquiterpenoid antibiotic albaflavenone, the polyketide germicidin A, and chalcone are produced during germination of the model streptomycete, S. coelicolor . Interestingly, the last two compounds revealed an inhibitory effect on the germination process. The secondary metabolites originating from the early stage of microbial growth may coordinate the development of the producer ( quorum sensing ) and/or play a role in competitive microflora repression ( quorum quenching ) in their nature environments.

Secondary Metabolites Produced during the Germination of Streptomyces coelicolor

PubMed Central

Čihák, Matouš; Kameník, Zdeněk; Šmídová, Klára; Bergman, Natalie; Benada, Oldřich; Kofroňová, Olga; Petříčková, Kateřina; Bobek, Jan

2017-01-01

Spore awakening is a series of actions that starts with purely physical processes and continues via the launching of gene expression and metabolic activities, eventually achieving a vegetative phase of growth. In spore-forming microorganisms, the germination process is controlled by intra- and inter-species communication. However, in the Streptomyces clade, which is capable of developing a plethora of valuable compounds, the chemical signals produced during germination have not been systematically studied before. Our previously published data revealed that several secondary metabolite biosynthetic genes are expressed during germination. Therefore, we focus here on the secondary metabolite production during this developmental stage. Using high-performance liquid chromatography-mass spectrometry, we found that the sesquiterpenoid antibiotic albaflavenone, the polyketide germicidin A, and chalcone are produced during germination of the model streptomycete, S. coelicolor. Interestingly, the last two compounds revealed an inhibitory effect on the germination process. The secondary metabolites originating from the early stage of microbial growth may coordinate the development of the producer (quorum sensing) and/or play a role in competitive microflora repression (quorum quenching) in their nature environments. PMID:29326665

Terpenoids from rhizomes of Alpinia japonica inhibiting nitric oxide production.

PubMed

Li, Qiang-Ming; Luo, Jian-Guang; Yang, Ming-Hua; Kong, Ling-Yi

2015-03-01

A new sesquiterpenoid, 1, and three new diterpenoids, 3-5, along with five known compounds, 2 and 6-9, were isolated from rhizomes of Alpinia japonica. The structures of the new compounds were determined as (1R,4R,6S,7S,9S)-4α-hydroxy-1,9-peroxybisabola-2,10-diene (1), methyl (12E)-16-oxolabda-8(17),12-dien-15-oate (3), (12R)-15-ethoxy-12-hydroxylabda-8(17),13(14)-dien-16,15-olide (4), and methyl (11E)-14,15,16-trinorlabda-8(17),11-dien-13-oate (5) by means of spectroscopic data. The absolute configurations at C(4) in 1 and C(12) in 4 were deduced from the circular dichroism (CD) data of the in situ-formed [Rh2 (CF3 COO)4 ] complexes. Inhibitory effects of the isolates on NO production in lipopolysaccharide-induced RAW264.7 macrophages were evaluated, and 2-4, 6, and 7 were found to exhibit inhibitory activities with IC50 values between 14.6 and 34.3 μM. Copyright © 2015 Verlag Helvetica Chimica Acta AG, Zürich.

Dihydro-β-agarofurans from the roots of the Australian endemic rainforest tree Maytenus bilocularis act as leucine transport inhibitors.

PubMed

Wibowo, Mario; Wang, Qian; Holst, Jeff; White, Jonathan M; Hofmann, Andreas; Davis, Rohan A

2018-04-01

Phytochemical studies of the roots of the Australian plant, Maytenus bilocularis, resulted in the identification of six previously undescribed dihydro-β-agarofuran sesquiterpenoids, bilocularins D-I, along with three known natural products, namely 1α,2α,6β,15-tetraacetoxy-9β-benzoyloxydihydro-β-agarofuran, pristimerin, and celastrol. The structures of all compounds were characterized via analysis of 1D/2D NMR and MS data. The absolute configuration of bilocularin D was defined by X-ray crystallography analysis. Bilocularins D and G, 1α,2α,6β,15-tetraacetoxy-9β-benzoyloxydihydro-β-agarofuran, and celastrol inhibited leucine transport in the human prostate cancer cell line LNCaP with IC 50 values ranging from 2.5-27.9 μM, which were more potent than the L-type amino acid transporter (LAT) family inhibitor 2-aminobicyclo[2,2,1]-heptane-2-carboxylic acid (BCH). Bilocularins D-F are the first examples of dihydro-β-agarofurans bearing a hydroxyacetate group. Copyright © 2018 Elsevier Ltd. All rights reserved.

Phytochemical composition of the essential oil of different populations of Stachys lavandulifolia Vahl

PubMed Central

Pirbalouti, Abdollah Ghasemi; Mohammadi, Maryam

2013-01-01

Objective To examine the chemical variability in inflorescences of wild populations of Stachys lavandulifolia Vahl (S. lavandulifolia) collected throughout two provinces (Isfahan and Chaharmahal va Bakhtiary), Southwest Iran. Methods The essential oils of S. lavandulifolia Vahl from seven locations were obtained by hydro-distillation and analysed by gas chromatography and gas chromatography-mass spectrometry. Results The results revealed that distinct differences in the content of compounds depending on region of sample collection. The main constituents of the essential oils were α-thujone (0.3%-32.3%), α-pinene (trace to 37.3%), myrcene (0.5%-15.9%), β-phellandrene (1.1%-37.9%), germacrene D (0.4%-11.3%), Δ-cadinene (trace to 11.6%) and 1, 4-methano-1 H-indene (trace to 10.1%). Conclusions The results of the present study indicated that essential oil components of S. lavandulifolia Vahl can be varied with genetic (ecotype), environmental conditions and geographic origin. In general, the essential oils of various populations of S. lavandulifolia Vahl were rich in monoterpenoids and sesquiterpenoids. PMID:23593591

Chemical Composition of Volatiles; Antimicrobial, Antioxidant and Cholinesterase Inhibitory Activity of Chaerophyllum aromaticum L. (Apiaceae) Essential Oils and Extracts.

PubMed

Petrović, Goran M; Stamenković, Jelena G; Kostevski, Ivana R; Stojanović, Gordana S; Mitić, Violeta D; Zlatković, Bojan K

2017-05-01

The present study reports the chemical composition of the headspace volatiles (HS) and essential oils obtained from fresh Chaerophyllum aromaticum root and aerial parts in full vegetative phase, as well as biological activities of their essential oils and MeOH extracts. In HS samples, the most dominant components were monoterpene hydrocarbons. On the other hand, the essential oils consisted mainly of sesquiterpenoids, representing 73.4% of the root and 63.4% of the aerial parts essential oil. The results of antibacterial assay showed that the aerial parts essential oil and MeOH extract have no antibacterial activity, while the root essential oil and extract showed some activity. Both of the tested essential oils exhibited anticholinesterase activity (47.65% and 50.88%, respectively); MeOH extract of the root showed only 8.40% inhibition, while aerial part extract acted as an activator of cholinesterase. Regarding the antioxidant activity, extracts were found to be more effective than the essential oils. © 2017 Wiley-VHCA AG, Zurich, Switzerland.

Glucosylation and Other Biotransformations of T-2 Toxin by Yeasts of the Trichomonascus Clade

PubMed Central

Price, Neil P. J.; Kurtzman, Cletus P.

2012-01-01

Trichothecenes are sesquiterpenoid toxins produced by Fusarium species. Since these mycotoxins are very stable, there is interest in microbial transformations that can remove toxins from contaminated grain or cereal products. Twenty-three yeast species assigned to the Trichomonascus clade (Saccharomycotina, Ascomycota), including four Trichomonascus species and 19 anamorphic species presently classified in Blastobotrys, were tested for their ability to convert the trichothecene T-2 toxin to less-toxic products. These species gave three types of biotransformations: acetylation to 3-acetyl T-2 toxin, glycosylation to T-2 toxin 3-glucoside, and removal of the isovaleryl group to form neosolaniol. Some species gave more than one type of biotransformation. Three Blastobotrys species converted T-2 toxin into T-2 toxin 3-glucoside, a compound that has been identified as a masked mycotoxin in Fusarium-infected grain. This is the first report of a microbial whole-cell method for producing trichothecene glycosides, and the potential large-scale availability of T-2 toxin 3-glucoside will facilitate toxicity testing and development of methods for detection of this compound in agricultural and other products. PMID:23042183

Volatile chemicals identified in extracts from leaves of Japanese mugwort (Artemisia princeps pamp.).

PubMed

Umano, K; Hagi, Y; Nakahara, K; Shoji, A; Shibamoto, T

2000-08-01

Extracts from leaves of Japanese mugwort (Artemisia princeps Pamp.) were obtained using two methods: steam distillation under reduced pressure followed by dichloromethane extraction (DRP) and simultaneous purging and extraction (SPSE). A total of 192 volatile chemicals were identified in the extracts obtained by both methods using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). They included 47 monoterpenoids (oxygenated monoterpenes), 26 aromatic compounds, 19 aliphatic esters, 18 aliphatic alcohols, 17 monoterpenes (hydrocarbon monoterpenes), 17 sesquiterpenes (hydrocarbon sesquiterpenes), 13 sesquiterpenoids (oxygenated sesquiterpenes), 12 aliphatic aldehydes, 8 aliphatic hydrocarbons, 7 aliphatic ketones, and 9 miscellaneous compounds. The major volatile constituents of the extract by DRP were borneol (10.27 ppm), alpha-thujone (3.49 ppm), artemisia alcohol (2.17 ppm), verbenone (1.85 ppm), yomogi alcohol (1.50 ppm), and germacren-4-ol (1.43 ppm). The major volatile constituents of the extract by SPSE were 1,8-cineole (8.12 ppm), artemisia acetate (4.22 ppm), alpha-thujone (3.20 ppm), beta-caryophyllene (2.39 ppm), bornyl acetate (2.05 ppm), borneol (1.80 ppm), and trans-beta-farnesene (1. 78 ppm).

Antifeedant effect of polygodial and drimenol derivatives against Spodoptera frugiperda and Epilachna paenulata and quantitative structure-activity analysis.

PubMed

Montenegro, Iván J; Del Corral, Soledad; Diaz Napal, Georgina N; Carpinella, María C; Mellado, Marco; Madrid, Alejandro M; Villena, Joan; Palacios, Sara M; Cuellar, Mauricio A

2018-07-01

The antifeedant activity of 18 sesquiterpenoids of the drimane family (polygodial, drimenol and derivatives) was investigated. Polygodial, drimanic and nordrimanic derivatives were found to exert antifeedant effects against two insect species, Spodoptera frugiperda and Epilachna paenulata, which are pests of agronomic interest, indicating that they have potential as biopesticide agents. Among the 18 compounds tested, the epoxynordrimane compound (11) and isonordrimenone (4) showed the highest activity [50% effective concentration (EC 50 ) = 23.28 and 25.63 nmol cm - 2 , respectively, against S. frugiperda, and 50.50 and 59.00 nmol/cm 2 , respectively, against E. paenulata]. The results suggest that drimanic compounds have potential as new agents against S. frugiperda and E. paenulata. A quantitative structure-activity relationship (QSAR) analysis of the whole series, supported by electronic studies, suggested that drimanic compounds have structural features necessary for increasing antifeedant activity, namely a C-9 carbonyl group and an epoxide at C-8 and C-9. © 2018 Society of Chemical Industry. © 2018 Society of Chemical Industry.

Sesquiterpenes from the Saudi Red Sea: Litophyton arboreum with their cytotoxic and antimicrobial activities.

PubMed

Abou El-Kassem, Lamia T; Hawas, Usama W; El-Desouky, Samy K; Al-Farawati, Radwan

2018-01-26

A new pseudoguaiane-type sesquiterpene named litopharbol (1) was isolated from the methanolic extract of the Red Sea soft coral Litophyton arboreum, along with known sesquiterpenoids alismol (2), alismorientol B (3), teuhetenone A (4), and calamusin I (5); steroid, 24-methyl-cholesta-5,24(28)-diene-3β-ol (6), alkyl glyceryl ether, chimyl alcohol (7); sphingolipid, erythro-N-dodecanoyl-docosasphinga-(4E,8E)-dienine (8); and nitrogenous bases, thymine (9) and thymidine (10). The structures were determined on the basis of nuclear magnetic resonance (NMR) spectroscopic (1D and 2D NMR data including heteronuclear single quantum coherence spectroscopy, heteronuclear multiple-bond correlation spectroscopy, and nuclear Overhauser effect spectroscopy) and mass spectrometric analyses. Compounds 1-5 were explored for antimicrobial activity and cancer cell line sensitivity tests. Compound 1 exhibited antibacterial activity against Bacillus cereus with a minimum inhibition concentration of 1.8 μg/mL, whereas compound 3 showed significant potent cytotoxic effect against MCF-7 (breast cancer cells) with IC50 4.32 μM.

Terpenoids from Curcuma wenyujin increased glucose consumption on HepG2 cells.

PubMed

Zhou, Chang-Xin; Zhang, Li-Sha; Chen, Fei-Fei; Wu, Hao-Shu; Mo, Jian-Xia; Gan, Li-She

2017-09-01

Thirty four terpenoids, including two new cadinane-type sesquiterpenoids containing conjugated aromatic-ketone moieties, curcujinone A (1) and curcujinone B (2), were isolated from 95% ethanol extract of the root tubers of Curcuma wenyujin. Their structures were determined by spectroscopic methods, especially 2D NMR and HRMS techniques. The relative and absolute configurations of 1 and 2 were identified by quantum chemical DFT and TDDFT calculations of the 13 C NMR chemical shifts, ECD spectra, and specific optical rotations. All compounds and extracts were evaluated for their anti-diabetic activities with a glucose consumption model on HepG2 Cells. The petroleum fraction CWP (10μg/mL) and compounds curcumenol (4), 7α,11α-epoxy-5β-hydroxy-9-guaiaen-8-one (5), curdione (17), (1S, 4S, 5S 10S)-germacrone (18), zederone (20), a mixture of curcumanolide A (25) and curcumanolide B (26), gajutsulactone B (27), and wenyujinin C (30) showed promising activities with over 45% increasing of glucose consumption at 10μM. Copyright © 2017. Published by Elsevier B.V.

New Metabolites and Bioactive Chlorinated Benzophenone Derivatives Produced by a Marine-Derived Fungus Pestalotiopsis heterocornis

PubMed Central

Lei, Hui; Lin, Xiuping; Han, Li; Ma, Jian; Ma, Qingjuan; Zhong, Jialiang; Liu, Yonghong; Sun, Tiemin; Wang, Jinhui; Huang, Xueshi

2017-01-01

Four new compounds, including two isocoumarins, pestaloisocoumarins A and B (1, 2), one sesquiterpenoid degradation, isopolisin B (4), and one furan derivative, pestalotiol A (5), together with one known isocoumarin, gamahorin (3), and three chlorinated benzophenone derivatives, pestalachloride B (6), pestalachloride E (7) and a mixture of pestalalactone atropisomers (8a/8b), were isolated from a culture of the fungus Pestalotiopsis heterocornis associated with sponge Phakellia fusca. These new chemical structures were established using NMR and MS spectroscopic data, as well as single-crystal X-ray crystallographic analysis and CD Cotton effects. All of the isolated compounds were evaluated for their antimicrobial and cytotoxic activities. Isocoumarins 1–3, showed antibacterial activities against Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis with MIC values ranging from 25 to 100 μg/mL and weak antifungal activities. Chlorinated benzophenone derivatives 6–8 exhibited antibacterial activities against S. aureus and B. subtilis with MIC values ranging from 3.0 to 50 μg/mL and cytotoxicities against four human cancer cell lines with IC50 values of 6.8–87.8 μM. PMID:28335391

Essential Oils from Neotropical Piper Species and Their Biological Activities

PubMed Central

da Trindade, Rafaela; Alves, Nayara Sabrina; Figueiredo, Pablo Luís; Maia, José Guilherme S.; Setzer, William N.

2017-01-01

The Piper genus is the most representative of the Piperaceae reaching around 2000 species distributed in the pantropical region. In the Neotropics, its species are represented by herbs, shrubs, and lianas, which are used in traditional medicine to prepare teas and infusions. Its essential oils (EOs) present high yield and are chemically constituted by complex mixtures or the predominance of main volatile constituents. The chemical composition of Piper EOs displays interspecific or intraspecific variations, according to the site of collection or seasonality. The main volatile compounds identified in Piper EOs are monoterpenes hydrocarbons, oxygenated monoterpenoids, sesquiterpene hydrocarbons, oxygenated sesquiterpenoids and large amounts of phenylpropanoids. In this review, we are reporting the biological potential of Piper EOs from the Neotropical region. There are many reports of Piper EOs as antimicrobial agents (fungi and bacteria), antiprotozoal (Leishmania spp., Plasmodium spp., and Trypanosoma spp.), acetylcholinesterase inhibitor, antinociceptive, anti-inflammatory and cytotoxic activity against different tumor cells lines (breast, leukemia, melanoma, gastric, among others). These studies can contribute to the rational and economic exploration of Piper species, once they have been identified as potent natural and alternative sources to treat human diseases. PMID:29240662

Antifungal and Ichthyotoxic Sesquiterpenoids from Santalum album Heartwood.

PubMed

Kim, Tae Hoon; Hatano, Tsutomu; Okamoto, Keinosuke; Yoshida, Takashi; Kanzaki, Hiroshi; Arita, Michiko; Ito, Hideyuki

2017-07-08

In our continuing study on a survey of biologically active natural products from heartwood of Santalum album (Southwest Indian origin), we newly found potent fish toxic activity of an n -hexane soluble extract upon primary screening using killifish (medaka) and characterized α-santalol and β-santalol as the active components. The toxicity (median tolerance limit (TLm) after 24 h at 1.9 ppm) of α-santalol was comparable with that of a positive control, inulavosin (TLm after 24 h at 1.3 ppm). These fish toxic compounds including inulavosin were also found to show a significant antifungal effect against a dermatophytic fungus, Trichophyton rubrum . Based on a similarity of the morphological change of the immobilized Trichophyton hyphae in scanning electron micrographs between treatments with α-santalol and griseofulvin (used as the positive control), inhibitory effect of α-santalol on mitosis (the antifungal mechanism proposed for griseofulvin) was assessed using sea urchin embryos. As a result, α-santalol was revealed to be a potent antimitotic agent induced by interference with microtubule assembly. These data suggested that α-santalol or sandalwood oil would be promising to further practically investigate as therapeutic agent for cancers as well as fungal skin infections.

In vitro antimalarial studies of novel artemisinin biotransformed products and its derivatives.

PubMed

Gaur, Rashmi; Darokar, Mahendra P; Ajayakumar, P V; Shukla, Ram Sajiwan; Bhakuni, Rajendra Singh

2014-11-01

Biotransformation of antimalarial drug artemisinin by fungi Rhizopus stolonifer afforded three sesquiterpenoid derivatives. The transformed products were 1α-hydroxyartemisinin (3), 3.0%, a new compound, 10β-hydroxyartemisinin, 54.5% (4) and deoxyartemisinin (2) in 9% yield. The fungus expressed high-metabolism activity (66.5%). The chemical structures of the compounds were elucidated by 1D, 2D NMR spectrometry and mass spectral data. The major compound 10β-hydroxyartemisinin (4) was chemically converted to five new derivatives 5-9. All the compounds 3-9 were subjected for in vitro anti-malarial activity. 10β-Hydroxy-12β-arteether (8), IC50 at 18.29nM was found to be 10 times better active than its precursor 4 (184.56nM) and equipotent antimalarial with natural drug artemisinin whereas the α-derivative 9 is 3 times better than 4 under in vitro conditions. Therefore, the major biotransformation product 4 can be exploited for further modification into new clinically potent molecules. The results show the versatility of microbial-catalyzed biotransformations leading to the introduction of a hydroxyl group at tertiary position in artemisinin in derivative (3). Copyright © 2014 Elsevier Ltd. All rights reserved.

Methyl Jasmonate Induces Traumatic Resin Ducts, Terpenoid Resin Biosynthesis, and Terpenoid Accumulation in Developing Xylem of Norway Spruce Stems1

PubMed Central

Martin, Diane; Tholl, Dorothea; Gershenzon, Jonathan; Bohlmann, Jörg

2002-01-01

Norway spruce (Picea abies L. Karst) produces an oleoresin characterized by a diverse array of terpenoids, monoterpenoids, sesquiterpenoids, and diterpene resin acids that can protect conifers against potential herbivores and pathogens. Oleoresin accumulates constitutively in resin ducts in the cortex and phloem (bark) of Norway spruce stems. De novo formation of traumatic resin ducts (TDs) is observed in the developing secondary xylem (wood) after insect attack, fungal elicitation, and mechanical wounding. Here, we characterize the methyl jasmonate-induced formation of TDs in Norway spruce by microscopy, chemical analyses of resin composition, and assays of terpenoid biosynthetic enzymes. The response involves tissue-specific differentiation of TDs, terpenoid accumulation, and induction of enzyme activities of both prenyltransferases and terpene synthases in the developing xylem, a tissue that constitutively lacks axial resin ducts in spruce. The induction of a complex defense response in Norway spruce by methyl jasmonate application provides new avenues to evaluate the role of resin defenses for protection of conifers against destructive pests such as white pine weevils (Pissodes strobi), bark beetles (Coleoptera, Scolytidae), and insect-associated tree pathogens. PMID:12114556

Biogenic trypanocidal sesquiterpenes: lead compounds to design future trypanocidal drugs - a mini review

PubMed Central

2013-01-01

Human trypanosomiasis is a parasitic disease among poor people in Africa and Latin America. Therapy against African and American trypanosomiasis is based on a few drugs that often cause severe side-effects. Therefore, it is essential to develop drug discovery especially from natural origins. Sesquiterpenes, a diverse group of natural terpenoids, are found in essential oils of many plants and show a broad range of bioactivities. They act through multiple mechanisms in the chemotherapy of trypanosomiasis. Some of these active compounds contain hydroperoxides, aldehydes, alcohols, α,β-unsaturated γ-lactone and even halogenated moieties. Among the compounds reported, sesquiterpene lactones showed a potent anti-trypanosoma effect comparable with commercial trypanocidal drugs. Trypanocidal activity of sesquiterpene lactones mostly depends on the reaction between γ-lactone moieties and nucleophile groups of trypanithione, which is essential for Trypanosoma defense against the oxidative stresses. Elatol is a sesquiterpenoid from marine algae, with a different structure and considerable trypanocidal activity which could be an interesting candidate for further antiprotozoal investigations. To develop novel drugs with higher efficacy and lower toxicity from natural products, this review summarizes the more recent information on trypanocidal activities of various sesquiterpenes. PMID:23676125

Sesquiterpenoids with PTP1B Inhibitory Activity and Cytotoxicity from the Edible Mushroom Pleurotus citrinopileatus.

PubMed

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

2016-05-01

One new perhydrobenzannulated 5,5-spiroketal sesquiterpene, pleurospiroketal F (1), as well as six new modified bisabolene sesquiterpenes pleurotins A-F (2-7) were isolated from solid-state fermentation of Pleurotus citrinopileatus. The structures of compounds 1-7 were determined by NMR and MS spectroscopic analysis. The absolute configuration of 1 was determined by X-ray diffraction analysis, while the absolute configurations of 3-7 were assigned using the in situ dimolybdenum circular dichroism method and circular dichroism data comparison. Protein tyrosine phosphatase 1B plays a crucial role as a negative regulator of the insulin-dependent signal cascades. Therefore, the protein tyrosine phosphatase 1B inhibitor can be used for treating type 2 diabetes mellitus and obesity. Compounds 2 and 6 showed moderate inhibitory effects on protein tyrosine phosphatase 1B with IC50 s of 32.1 µM and 30.5 µM, respectively. The kinetic study confirmed compound 2 to be a noncompetitive inhibitor. Compounds 1-7 did not show cytotoxic activity against cancer cell lines (IC50 > 50 µM). Georg Thieme Verlag KG Stuttgart · New York.

Discovery of Highly Sweet Compounds from Natural Sources

NASA Astrophysics Data System (ADS)

Kinghorn, A. Douglas; Kennelly, Edward J.

1995-08-01

Sucrose, the most widely used sweetener globally, is of plant origin. In addition, a number of other plant constituents are employed as dietary sucrose substitutes in one or more countries, including the diterpenoid, stevioside, the triterpenoid, glycyrrhizin, and the protein, thaumatin. Accordingly, there has been much interest in discovering further examples of potently sweet compounds of natural origin, for potential use in foods, beverages, and medicines. Approximately 75 plant-derived compounds are presently known, mainly representative of the flavonoid, proanthocyandin, protein, steroidal saponin, and terpenoid chemotypes. In our program directed towards the elucidation of further highly sweet molecules from plants, candidate sweet-tasting plants for laboratory investigation are obtained from ethnobotanical observations in the field or in the existing literature. Examples of novel sweet-tasting compounds obtained so far are the sesquiterpenoids, hernandulcin and 4beta-hydroxyhemandulcin; the triterpenoids, abrusosides A-D; a semi-synthetic dihydroflavonol based on the naturally occurring substance, dihydroquercetin 3-acetate; and the proanthocyanidin, selligueain A. Natural product sweeteners may be of potential commercial use per se, and can be used for synthetic modification to produce improved sweeteners, and can also be of value scientifically to aid in the better understanding of structure-sweetness relationships.

Crataegus pinnatifida: chemical constituents, pharmacology, and potential applications.

PubMed

Wu, Jiaqi; Peng, Wei; Qin, Rongxin; Zhou, Hong

2014-01-30

Crataegus pinnatifida (Hawthorn) is widely distributed in China and has a long history of use as a traditional medicine. The fruit of C. pinnatifida has been used for the treatment of cardiodynia, hernia, dyspepsia, postpartum blood stasis, and hemafecia and thus increasing interest in this plant has emerged in recent years. Between 1966 and 2013, numerous articles have been published on the chemical constituents, pharmacology or pharmacologic effects and toxicology of C. pinnatifida. To review the pharmacologic advances and to discuss the potential perspective for future investigation, we have summarized the main literature findings of these publications. So far, over 150 compounds including flavonoids, triterpenoids, steroids, monoterpenoids, sesquiterpenoids, lignans, hydroxycinnamic acids, organic acids and nitrogen-containing compounds have been isolated and identified from C. pinnatifida. It has been found that these constituents and extracts of C. pinnatifida have broad pharmacological effects with low toxicity on, for example, the cardiovascular, digestive, and endocrine systems, and pathogenic microorganisms, supporting the view that C. pinnatifida has favorable therapeutic effects. Thus, although C. pinnatifida has already been widely used as pharmacological therapy, due to its various active compounds, further research is warranted to develop new drugs.

Compositional Variation and Bioactivity of the Leaf Essential Oil of Montanoa guatemalensis from Monteverde, Costa Rica: A Preliminary Investigation

PubMed Central

Flatt, Victoria D.; Campos, Carlos R.; Kraemer, Maria P.; Bailey, Brittany A.; Satyal, Prabodh; Setzer, William N.

2015-01-01

Background: Montanoa guatemalensis is a small to medium-sized tree in the Asteraceae that grows in Central America from Mexico south through Costa Rica. There have been no previous investigations on the essential oil of this tree. Methods: The leaf essential oils of M. guatemalensis were obtained from different individual trees growing in Monteverde, Costa Rica, in two different years, and were analyzed by gas chromatography—mass spectrometry. Results: The leaf oils from 2008 were rich in sesquiterpenoids, dominated by α-selinene, β-selinene, and cyclocolorenone, with lesser amounts of the monoterpenes α-pinene and limonene. In contrast, the samples from 2009 showed no α- or β-selinene, but large concentrations of trans-muurola-4(14),5-diene, β-cadinene, and cyclocolorenone, along with greater concentrations of α-pinene and limonene. The leaf oils were screened for cytotoxic and antimicrobial activities and did show selective cytotoxic activity on MDA-MB-231 breast tumor cells. Conclusion: M. guatemalensis leaf oil, rich in cyclocolorenone, α-selinene, and β-selinene, showed selective in vitro cytotoxic activity to MDA-MB-231 cells. The plant may be a good source of cyclocolorenone. PMID:28930215

Secondary metabolites from Ganoderma.

PubMed

Baby, Sabulal; Johnson, Anil John; Govindan, Balaji

2015-06-01

Ganoderma is a genus of medicinal mushrooms. This review deals with secondary metabolites isolated from Ganoderma and their biological significance. Phytochemical studies over the last 40years led to the isolation of 431 secondary metabolites from various Ganoderma species. The major secondary compounds isolated are (a) C30 lanostanes (ganoderic acids), (b) C30 lanostanes (aldehydes, alcohols, esters, glycosides, lactones, ketones), (c) C27 lanostanes (lucidenic acids), (d) C27 lanostanes (alcohols, lactones, esters), (e) C24, C25 lanostanes (f) C30 pentacyclic triterpenes, (g) meroterpenoids, (h) farnesyl hydroquinones (meroterpenoids), (i) C15 sesquiterpenoids, (j) steroids, (k) alkaloids, (l) prenyl hydroquinone (m) benzofurans, (n) benzopyran-4-one derivatives and (o) benzenoid derivatives. Ganoderma lucidum is the species extensively studied for its secondary metabolites and biological activities. Ganoderma applanatum, Ganoderma colossum, Ganoderma sinense, Ganoderma cochlear, Ganoderma tsugae, Ganoderma amboinense, Ganoderma orbiforme, Ganoderma resinaceum, Ganoderma hainanense, Ganoderma concinna, Ganoderma pfeifferi, Ganoderma neo-japonicum, Ganoderma tropicum, Ganoderma australe, Ganoderma carnosum, Ganoderma fornicatum, Ganoderma lipsiense (synonym G. applanatum), Ganoderma mastoporum, Ganoderma theaecolum, Ganoderma boninense, Ganoderma capense and Ganoderma annulare are the other Ganoderma species subjected to phytochemical studies. Further phytochemical studies on Ganoderma could lead to the discovery of hitherto unknown biologically active secondary metabolites. Copyright © 2015 Elsevier Ltd. All rights reserved.

Light Quality Dependent Changes in Morphology, Antioxidant Capacity, and Volatile Production in Sweet Basil (Ocimum basilicum)

PubMed Central

Carvalho, Sofia D.; Schwieterman, Michael L.; Abrahan, Carolina E.; Colquhoun, Thomas A.; Folta, Kevin M.

2016-01-01

Narrow-bandwidth light treatments may be used to manipulate plant growth, development and metabolism. In this report LED-based light treatments were used to affect yield and metabolic content of sweet basil (Ocimum basilicum L. cv “Ceasar”) grown in controlled environments. This culinary herb produces an aroma highly appreciated by consumers, primarily composed of terpenes/terpenoids, phenylpropanoids, and fatty-acid- derived volatile molecules. Basil plants were grown under narrow-bandwidth light conditions, and leaf area, height, mass, antioxidant capacity and volatile emissions were measured at various time points. The results indicate reproducible significant differences in specific volatiles, and in biochemical classes of volatiles, compared to greenhouse grown plants. For example, basil plants grown under blue/red/yellow or blue/red/green wavelengths emit higher levels of a subset of monoterpenoid volatiles, while a blue/red/far-red treatment leads to higher levels of most sesquiterpenoid volatile molecules. Specific light treatments increase volatile content, mass, and antioxidant capacity. The results show that narrow-bandwidth illumination can induce discrete suites of volatile classes that affect sensory quality in commercial herbs, and may be a useful tool in improving commercial production. PMID:27635127

Light Quality Dependent Changes in Morphology, Antioxidant Capacity, and Volatile Production in Sweet Basil (Ocimum basilicum).

PubMed

Carvalho, Sofia D; Schwieterman, Michael L; Abrahan, Carolina E; Colquhoun, Thomas A; Folta, Kevin M

2016-01-01

Narrow-bandwidth light treatments may be used to manipulate plant growth, development and metabolism. In this report LED-based light treatments were used to affect yield and metabolic content of sweet basil (Ocimum basilicum L. cv "Ceasar") grown in controlled environments. This culinary herb produces an aroma highly appreciated by consumers, primarily composed of terpenes/terpenoids, phenylpropanoids, and fatty-acid- derived volatile molecules. Basil plants were grown under narrow-bandwidth light conditions, and leaf area, height, mass, antioxidant capacity and volatile emissions were measured at various time points. The results indicate reproducible significant differences in specific volatiles, and in biochemical classes of volatiles, compared to greenhouse grown plants. For example, basil plants grown under blue/red/yellow or blue/red/green wavelengths emit higher levels of a subset of monoterpenoid volatiles, while a blue/red/far-red treatment leads to higher levels of most sesquiterpenoid volatile molecules. Specific light treatments increase volatile content, mass, and antioxidant capacity. The results show that narrow-bandwidth illumination can induce discrete suites of volatile classes that affect sensory quality in commercial herbs, and may be a useful tool in improving commercial production.

In-silico Leishmania target selectivity of antiparasitic terpenoids.

PubMed

Ogungbe, Ifedayo Victor; Setzer, William N

2013-07-03

Neglected Tropical Diseases (NTDs), like leishmaniasis, are major causes of mortality in resource-limited countries. The mortality associated with these diseases is largely due to fragile healthcare systems, lack of access to medicines, and resistance by the parasites to the few available drugs. Many antiparasitic plant-derived isoprenoids have been reported, and many of them have good in vitro activity against various forms of Leishmania spp. In this work, potential Leishmania biochemical targets of antiparasitic isoprenoids were studied in silico. Antiparasitic monoterpenoids selectively docked to L. infantum nicotinamidase, L. major uridine diphosphate-glucose pyrophosphorylase and methionyl t-RNA synthetase. The two protein targets selectively targeted by germacranolide sesquiterpenoids were L. major methionyl t-RNA synthetase and dihydroorotate dehydrogenase. Diterpenoids generally favored docking to L. mexicana glycerol-3-phosphate dehydrogenase. Limonoids also showed some selectivity for L. mexicana glycerol-3-phosphate dehydrogenase and L. major dihydroorotate dehydrogenase while withanolides docked more selectively with L. major uridine diphosphate-glucose pyrophosphorylase. The selectivity of the different classes of antiparasitic compounds for the protein targets considered in this work can be explored in fragment- and/or structure-based drug design towards the development of leads for new antileishmanial drugs.

Transcriptome Analysis of Thapsia laciniata Rouy Provides Insights into Terpenoid Biosynthesis and Diversity in Apiaceae

PubMed Central

Drew, Damian Paul; Dueholm, Bjørn; Weitzel, Corinna; Zhang, Ye; Sensen, Christoph W.; Simonsen, Henrik Toft

2013-01-01

Thapsia laciniata Rouy (Apiaceae) produces irregular and regular sesquiterpenoids with thapsane and guaiene carbon skeletons, as found in other Apiaceae species. A transcriptomic analysis utilizing Illumina next-generation sequencing enabled the identification of novel genes involved in the biosynthesis of terpenoids in Thapsia. From 66.78 million HQ paired-end reads obtained from T. laciniata roots, 64.58 million were assembled into 76,565 contigs (N50: 1261 bp). Seventeen contigs were annotated as terpene synthases and five of these were predicted to be sesquiterpene synthases. Of the 67 contigs annotated as cytochromes P450, 18 of these are part of the CYP71 clade that primarily performs hydroxylations of specialized metabolites. Three contigs annotated as aldehyde dehydrogenases grouped phylogenetically with the characterized ALDH1 from Artemisia annua and three contigs annotated as alcohol dehydrogenases grouped with the recently described ADH1 from A. annua. ALDH1 and ADH1 were characterized as part of the artemisinin biosynthesis. We have produced a comprehensive EST dataset for T. laciniata roots, which contains a large sample of the T. laciniata transcriptome. These transcriptome data provide the foundation for future research into the molecular basis for terpenoid biosynthesis in Thapsia and on the evolution of terpenoids in Apiaceae. PMID:23698765

Doxycycline hyclate-loaded bleached shellac in situ forming microparticle for intraperiodontal pocket local delivery.

PubMed

Phaechamud, Thawatchai; Chanyaboonsub, Nuttapong; Setthajindalert, Orn

2016-10-10

Bleached shellac (BS) is a water-insoluble polyester resin made up of sesquiterpenoid acids esterified with hydroxy aliphatic acids. In this study, BS dissolved in N-methyl pyrrolidone (NMP), dimethyl sulfoxide (DMSO) and 2-pyrrolidone was used as the internal phase of oil in oil emulsion using olive oil emulsified with glyceryl monostearate (GMS) as the external phase of in situ forming microparticles (ISM). Doxycycline hyclate (DH)-loaded BS ISMs were tested for emulsion stability, viscosity, rheology, transformation into microparticles, syringeability, drug release, surface topography, in vitro degradation and antimicrobial activities against Staphylococcus aureus, Streptococcus mutans and Porphyromonas gingivalis. All emulsions exhibited pseudoplastic flow and notably low syringeability force. Slower transformation from emulsion into microparticles of ISM prepared with 2-pyrrolidone was owing to slower solvent exchange of this solvent which promoted less porous structure of obtained BS matrix microparticles. The system containing 2-pyrrolidone exhibited a higher degradability than that prepared with DMSO. Developed DH-loaded BS ISMs exhibited a sustainable drug release for 47days with Fickian diffusion and effectively inhibited P. gingivalis, S. mutans and S. aureus. Therefore a DH-loaded BS ISM using olive oil containing GMS as the external phase and 2-pyrrolidone as a solvent was a suitable formulation for periodontitis treatment. Copyright © 2016 Elsevier B.V. All rights reserved.

Incorporation of absorption and metabolism into liver toxicity prediction for phytochemicals: A tiered in silico QSAR approach.

PubMed

Liu, Yitong

2018-05-18

An increased use of herbal dietary supplements has been associated with adverse liver effects such as elevated serum enzymes and liver failure. The safety assessment for herbal dietary supplements is challenging since they often contain complex mixtures of phytochemicals, most of which have unknown pharmacokinetic and toxicological properties. Rapid tools are needed to evaluate large numbers of phytochemicals for potential liver toxicity. The current study demonstrates a tiered approach combining identification of phytochemicals in liver toxic botanicals, followed by in silico quantitative structure-activity relationship (QSAR) evaluation of these phytochemicals for absorption (e.g. permeability), metabolism (cytochromes P450) and liver toxicity (e.g. elevated transaminases). First, 255 phytochemicals from 20 botanicals associated with clinical liver injury were identified, and the phytochemical structures were subsequently used for QSAR evaluation. Among these identified phytochemicals, 193 were predicted to be absorbed and then used to generate metabolites, which were both used to predict liver toxicity. Forty-eight phytochemicals were predicted as liver toxic, either due to parent phytochemicals or metabolites. Among them, nineteen phytochemicals have previous evidence of liver toxicity (e.g. pyrrolizidine alkaloids), while the majority were newly discovered (e.g. sesquiterpenoids). These findings help reveal new toxic phytochemicals in herbal dietary supplements and prioritize future toxicological testing. Published by Elsevier Ltd.

Characterization of the Drosophila Methoprene -tolerant gene product. Juvenile hormone binding and ligand-dependent gene regulation.

PubMed

Miura, Ken; Oda, Masahito; Makita, Sumiko; Chinzei, Yasuo

2005-03-01

Juvenile hormones (JHs) of insects are sesquiterpenoids that regulate a great diversity of processes in development and reproduction. As yet the molecular modes of action of JH are poorly understood. The Methoprene-tolerant (Met) gene of Drosophila melanogaster has been found to be responsible for resistance to a JH analogue (JHA) insecticide, methoprene. Previous studies on Met have implicated its involvement in JH signaling, although direct evidence is lacking. We have now examined the product of Met (MET) in terms of its binding to JH and ligand-dependent gene regulation. In vitro synthesized MET directly bound to JH III with high affinity (Kd = 5.3 +/- 1.5 nm, mean +/- SD), consistent with the physiological JH concentration. In transient transfection assays using Drosophila S2 cells the yeast GAL4-DNA binding domain fused to MET exerted JH- or JHA-dependent activation of a reporter gene. Activation of the reporter gene was highly JH- or JHA-specific with the order of effectiveness: JH III > JH II > JH I > methoprene; compounds which are only structurally related to JH or JHA did not induce any activation. Localization of MET in the S2 cells was nuclear irrespective of the presence or absence of JH. These results suggest that MET may function as a JH-dependent transcription factor.

Anti-Inflammatory Components from the Root of Solanum erianthum

PubMed Central

Chen, Yu-Chang; Lee, Hong-Zin; Chen, Hsin-Chun; Wen, Chi-Luan; Kuo, Yueh-Hsiung; Wang, Guei-Jane

2013-01-01

Two new norsesquiterpenoids, solanerianones A and B (1–2), together with nine known compounds, including four sesquiterpenoids, (−)-solavetivone (3), (+)-anhydro-β-rotunol (4), solafuranone (5), lycifuranone A (6); one alkaloid, N-trans-feruloyltyramine (7); one fatty acid, palmitic acid (8); one phenylalkanoid, acetovanillone (9), and two steroids, β-sitosterol (10) and stigmasterol (11) were isolated from the n-hexane-soluble part of the roots of Solanum erianthum. Their structures were elucidated on the basis of physical and spectroscopic data analyses. The anti-inflammatory activity of these isolates was monitored by nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophage RAW264.7 cells. The cytotoxicity towards human lung squamous carcinoma (CH27), human hepatocellular carcinoma (Hep 3B), human oral squamous carcinoma (HSC-3) and human melanoma (M21) cell lines was also screened by using an MTT assay. Of the compounds tested, 3 exhibited the strongest NO inhibition with the average maximum inhibition (Emax) at 100 μM and median inhibitory concentration (IC50) values of 98.23% ± 0.08% and 65.54 ± 0.18 μM, respectively. None of compounds (1–9) was found to possess cytotoxic activity against human cancer cell lines at concentrations up to 30 μM. PMID:23771024

The secondary metabolite euplotin C induces apoptosis-like death in the marine ciliated protist Euplotes vannus.

PubMed

Cervia, Davide; Di Giuseppe, Graziano; Ristori, Chiara; Martini, Davide; Gambellini, Gabriella; Bagnoli, Paola; Dini, Fernando

2009-01-01

The sesquiterpenoid euplotin C is a secondary metabolite produced by the ciliated protist Euplotes crassus and provides a mechanism for damping populations of potential competitors. Indeed, E. crassus is virtually resistant to its own product while different non-producer species representing an unbiased sample of the marine, interstitial, ciliate diversity are sensitive. For instance, euplotin C exerts a marked disruption of different homeostatic mechanisms in Euplotes vannus. We demonstrate by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay that euplotin C quickly decreases viability and mitochondrial function of E. vannus with a very high efficacy and at micromolar potency. In addition, euplotin C induces apoptosis in E. vannus as 4,6-diamino-2-phenylindole and terminal transferase dUTP nick end labeling staining show the rapid condensation and fragmentation of nuclear material in cells treated with euplotin C. These effects occur without detectable permeabilisation or rupture of cell membranes and with no major changes in the overall morphology, although some traits, such as vacuolisation and disorganized microtubules, can be observed by transmission electron microscopy. In particular, E. vannus show profound changes of the mitochondrial ultrastructure. Finally, we also show that caspase activity in E. vannus is increased by euplotin C. These data elucidate the pro-apoptotic role of euplotin C and suggest a mechanism for its impact on natural selection.

Chemical analysis of bioactive substances in seven siberian Saussurea species

NASA Astrophysics Data System (ADS)

Avdeeva, Elena; Reshetov, Yaroslav; Shurupova, Margarita; Zibareva, Larisa; Borisova, Evgeniia; Belousov, Mikhail

2017-11-01

Main groups of biologically active substances of seven siberian Saussurea species (S. controversa DC., S. latifolia Ledeb., S. parviflora (Poir.) DC., S. frolowii Ledeb, S. amara (L.) DC., S. salicifolia (L.) DC. and S. daurica Adams) have been studied using paper, thin-layer, performance liquid chromatography, IR spectroscopy, spectrophotometry and mass spectrometry with inductively coupled plasma. Siberian Saussurea species have a rich elemental composition and contain a variety of phenolic compounds, amino acids, polysaccharides. The majority of polysaccharides are accumulated by S. controversa, S. salicifolia and S. frolowii. These plants contain a significant amount of calcium that may be a species characteristic. All plants contain quercetin and its glycosides, in some species luteolin, kaempferol, glycosides of apigenin and myricetin were revealed. Phenolic acids with predominant content of caffeic, chlorogenic and cinnamic acids were found in all the species. The maximum amount of phenolic acids and flavonoids was determined in the grass of S. latifolia, S. controversa and S. daurica. Characteristic absorption bands of lactone carbonyl of sesquiterpenoids in IR spectrum found in S. latifolia, S. controversa, S. daurica, S. amara and S. salicifolia. HPLC / UV analysis showed that peaks with absorption maxima of 242-246 nm due to the presence of α,β-unsaturated ketone group in the structure of ecdysteroids were found in S. salicifolia, S. controversa, S. daurica and S. latifolia.

Chemical Composition and Insecticidal Activity of Essential Oils from Zanthoxylum dissitum Leaves and Roots against Three Species of Storage Pests.

PubMed

Wang, Cheng-Fang; Yang, Kai; You, Chun-Xue; Zhang, Wen-Juan; Guo, Shan-Shan; Geng, Zhu-Feng; Du, Shu-Shan; Wang, Yong-Yan

2015-05-04

This work aimed to investigate chemical composition of essential oils obtained from Zanthoxylum dissitum leaves and roots and their insecticidal activities against several stored product pests, namely the cigarette beetle (Lasioderma serricorne), red flour beetle (Tribolium castaneum) and black carpet beetle (Attagenus piceus). The analysis by GC-MS of the essential oils allowed the identification of 28 and 22 components, respectively. It was found that sesquiterpenoids comprised a fairly high portion of the two essential oils, with percentages of 74.0% and 80.9% in the leaves and roots, respectively. The main constituents identified in the essential oil of Z. dissitum leaves were δ-cadinol (12.8%), caryophyllene (12.7%), β-cubebene (7.9%), 4-terpineol (7.5%) and germacrene D-4-ol (5.7%), while humulene epoxide II (29.4%), caryophyllene oxide (24.0%), diepicedrene-1-oxide (10.7%) and Z,Z,Z-1,5,9,9-tetramethyl-1,4,7-cycloundecatriene (8.7%) were the major components in the essential oil of Z. dissitum roots. The insecticidal activity results indicated that the essential oil of Z. dissitum roots exhibited moderate contact toxicity against three species of storage pests, L. serricorne,T. castaneum and A. piceus, with LD50 values of 13.8, 43.7 and 96.8 µg/adult, respectively.

Sesquiterpenes and a monoterpenoid with acetylcholinesterase (AchE) inhibitory activity from Valeriana officinalis var. latiofolia in vitro and in vivo.

PubMed

Chen, Heng-Wen; He, Xuan-Hui; Yuan, Rong; Wei, Ben-Jun; Chen, Zhong; Dong, Jun-Xing; Wang, Jie

2016-04-01

Acetylcholinesterase Inhibitor (AchEI) is the most extensive in all anti-dementia drugs. The extracts and isolated compounds from the Valeriana genus have shown anti-dementia bioactivity. Four new sesquiterpenoids (1-4) and a new monoterpenoid (5) were isolated from the root of Valeriana officinalis var. latiofolia. The acetylcholinesterase (AchE) inhibitory activity of isolates was evaluated by modified Ellman method in vitro. Learning and memory ability of compound 4 on mice was evaluated by the Morris water maze. The contents of acetylcholine (Ach), acetylcholine transferase (ChAT) and AchE in mice brains were determined by colorimetry. The results showed IC50 of compound 4 was 0.161 μM in vitro. Compared with the normal group, the learning and memory ability of mice and the contents of Ach and ChAT decreased in model group mice (P<0.01), while the AchE increased (P<0.01). Compared with the model group, Ach and ChAT in the positive control group, the high-dose group and the medium-dose group increased (P<0.01), while the AchE decreased (P<0.01). Compound 4 can improve the learning and memory abilities of APPswe/PSΔE9 double-transgenic mice, and the mechanism may be related to the regulation of the relative enzyme in the cholinergic system. Copyright © 2016 Elsevier B.V. All rights reserved.

Biosynthesis of Germacrene A Carboxylic Acid in Chicory Roots. Demonstration of a Cytochrome P450 (+)-Germacrene A Hydroxylase and NADP+-Dependent Sesquiterpenoid Dehydrogenase(s) Involved in Sesquiterpene Lactone Biosynthesis

PubMed Central

de Kraker, Jan-Willem; Franssen, Maurice C. R.; Dalm, Marcella C. F.; de Groot, Aede; Bouwmeester, Harro J.

2001-01-01

Sprouts of chicory (Cichorium intybus), a vegetable grown in the dark, have a slightly bitter taste associated with the presence of guaianolides, eudesmanolides, and germacranolides. The committed step in the biosynthesis of these compounds is catalyzed by a (+)-germacrene A synthase. Formation of the lactone ring is the postulated next step in biosynthesis of the germacrene-derived sesquiterpene lactones. The present study confirms this hypothesis by isolation of enzyme activities from chicory roots that introduce a carboxylic acid function in the germacrene A isopropenyl side chain, which is necessary for lactone ring formation. (+)-Germacrene A is hydroxylated to germacra-1(10),4,11(13)-trien-12-ol by a cytochrome P450 enzyme, and is subsequently oxidized to germacra-1(10),4,11(13)-trien-12-oic acid by NADP+-dependent dehydrogenase(s). Both oxidized germacrenes were detected as their Cope-rearrangement products elema-1,3,11(13)-trien-12-ol and elema-1,3,11(13)-trien-12-oic acid, respectively. The cyclization products of germacra-1(10),4,11(13)-trien-12-ol, i.e. costol, were also observed. The (+)-germacrene A hydroxylase is inhibited by carbon monoxide (blue-light reversible), has an optimum pH at 8.0, and hydroxylates β-elemene with a modest degree of enantioselectivity. PMID:11299372

Warburgia: a comprehensive review of the botany, traditional uses and phytochemistry.

PubMed

Leonard, Carmen M; Viljoen, Alvaro M

2015-05-13

The genus Warburgia (Canellaceae) is represented by several medicinal trees found exclusively on the African continent. Traditionally, extracts and products produced from Warburgia species are regarded as important natural African antibiotics and have been used extensively as part of traditional healing practices for the treatment of fungal, bacterial and protozoal infections in both humans and animals. We here aim to collate and review the fragmented information on the ethnobotany, phytochemistry and biological activities of ethnomedicinally important Warburgia species and present recommendations for future research. Peer-reviewed articles using "Warburgia" as search term ("all fields") were retrieved from Scopus, ScienceDirect, SciFinder and Google Scholar with no specific time frame set for the search. In addition, various books were consulted that contained botanical and ethnopharmacological information. The ethnopharmacology, phytochemistry and biological activity of Warburgia are reviewed. Most of the biological activities are attributed to the drimane sesquiterpenoids, including polygodial, warburganal, muzigadial, mukaadial and ugandensial, flavonoids and miscellaneous compounds present in the various species. In addition to anti-infective properties, Warburgia extracts are also used to treat a wide range of ailments, including stomach aches, fever and headaches, which may also be a manifestation of infections. The need to record anecdotal evidence is emphasised and conservation efforts are highlighted to contribute to the protection and preservation of one of Africa's most coveted botanical resources. Copyright © 2015 Elsevier Ireland Ltd. All rights reserved.

Essential oil composition from two species of Piperaceae family grown in Colombia.

PubMed

Pino Benitez, Nayive; Meléndez León, Erika M; Stashenko, Elena E

2009-10-01

Essential oil compositions of aerial parts from two species in the Piper (Piperaceae family) genera: Piper lanceaefolium Kunth and Piper hispidum Sw., frequently called deflated (for the anti-inflammatory activity) or cord. Piperaceae leaves were collected in different regions of the Chocó department in northwestern Colombia and identified by botanists from Colombian National Herbarium, where a voucher of each specimen were deposited (No- COL 519993 and No- COL 519969, respectively). The essential oils were obtained by microwave-assisted hydrodistillation (MWHD) and analyzed by gas chromatography-mass spectrometry (GC-MS). The P. lanceaefolium essential oil was sesquiterpenoid type (71.7%). This composition was represented by sesquiterpenes hydrocarbons (58.5%) and by their oxygenated derivates (13.2%); the main compounds were, trans-beta-caryophyllene (11.6%) and germacrene D (10.7%) followed by alpha-selinene (7.8%), beta-pinene (5.4%), beta-selinene (4.8%), and alpha-cubebene (4.3%). The Piper hispidum essential oil also was sesquiterpene type (74.4%) and oxygenated sesquiterpenes (46.4%) followed by sesquiterpenes hydrocarbons (28.0%). The main compounds were trans-nerolidol (23.6%) and caryophyllene oxide (5.4%) followed by beta-elemene (5.1%), trans-beta-caryophyllene (5.1%), curzerene (4.9%), and germacrene B (4.5%). Trans-beta-caryophyllene presents the higher percentage of the common compounds in the two species' essential oil (11.6% and 5.1% in P. lanceaefolium and P. hispidum, respectively).

Hepatic protection and anticancer activity of curcuma: a potential chemopreventive strategy against hepatocellular carcinoma.

PubMed

Li, Yan; Shi, Xue; Zhang, Jingwen; Zhang, Xiang; Martin, Robert C G

2014-02-01

Malignant transformation of hepatocellular carcinoma (HCC) occurs through repetitive liver injury in a context of inflammation and oxidative DNA damage. A spectrum of natural sesquiterpenoids from curcuma oil has displayed antioxidant, anti-inflammatory and anti-carcinogenic properties. The aim of the study was to investigate the hepatoprotective and anti-HCC effects of curcuma oil in vivo and in vitro. Mice were pretreated with curcuma oil (100 mg/kg) for 3 days, then treated with Concanavalin A (30 mg/kg). The hepatic tissue was evaluated for histology, CD4+ cell, interferon-γ, apoptosis, lipid peroxidation, 8-hydroxy-deoxyguanosine and MnSOD. C57L/J mice were treated with curcuma oil and 107 Hepa1-6 cells directly inoculated into liver lobes. The effects of curcuma oil on cell growth and cell death were evaluated. In addition, MnSOD, HSP60, catalase, NF-κB and caspase-3 were also investigated in the Hepa1-6 cells treated with curcuma oil. Pretreatment with curcuma oil significantly attenuates inflammation and oxidative damage by Concanavalin A. Treatment with curcuma oil can decrease the incidence of HCC. Curcuma oil inhibits cell growth and induces cell death in Hepa1-6 cells. Curcuma protected mice with hepatic injury from inflammatory and oxidative stress. Curcuma oil can inhibit hepatoma cell growth in vivo and in vitro.

Hepatic protection and anticancer activity of curcuma: A potential chemopreventive strategy against hepatocellular carcinoma

PubMed Central

LI, YAN; SHI, XUE; ZHANG, JINGWEN; ZHANG, XIANG; MARTIN, ROBERT C.G.

2014-01-01

Malignant transformation of hepatocellular carcinoma (HCC) occurs through repetitive liver injury in a context of inflammation and oxidative DNA damage. A spectrum of natural sesquiterpenoids from curcuma oil has displayed anti-oxidant, anti-inflammatory and anti-carcinogenic properties. The aim of the study was to investigate the hepatoprotective and anti-HCC effects of curcuma oil in vivo and in vitro. Mice were pretreated with curcuma oil (100 mg/kg) for 3 days, then treated with Concanavalin A (30 mg/kg). The hepatic tissue was evaluated for histology, CD4+ cell, interferon-γ, apoptosis, lipid peroxidation, 8-hydroxy-deoxyguanosine and MnSOD. C57L/J mice were treated with curcuma oil and 107 Hepa1-6 cells directly inoculated into liver lobes. The effects of curcuma oil on cell growth and cell death were evaluated. In addition, MnSOD, HSP60, catalase, NF-κB and caspase-3 were also investigated in the Hepa1-6 cells treated with curcuma oil. Pretreatment with curcuma oil significantly attenuates inflammation and oxidative damage by Concanavalin A. Treatment with curcuma oil can decrease the incidence of HCC. Curcuma oil inhibits cell growth and induces cell death in Hepa1-6 cells. Curcuma protected mice with hepatic injury from inflammatory and oxidative stress. Curcuma oil can inhibit hepatoma cell growth in vivo and in vitro. PMID:24270742

Identification of Bioactivity, Volatile and Fatty Acid Profile in Supercritical Fluid Extracts of Mexican arnica.

PubMed

García-Pérez, J Saúl; Cuéllar-Bermúdez, Sara P; Arévalo-Gallegos, Alejandra; Rodríguez-Rodríguez, José; Iqbal, Hafiz M N; Parra-Saldivar, Roberto

2016-09-12

Supercritical fluid extraction (SFE) is a sustainable technique used for the extraction of lipophilic metabolites such as pigments and fatty acids. Arnica plant is considered a potential candidate material with high antioxidant and antimicrobial activities. Therefore, in this study, a locally available Heterotheca inuloides, also known as Mexican arnica, was analyzed for the extraction of high-value compounds. Based on different pressure (P), temperature (T), and co-solvent (CoS), four treatments (T) were prepared. A maximum 7.13% yield was recovered from T2 (T = 60 °C, P = 10 MPa, CoS = 8 g/min), followed by 6.69% from T4 (T = 60 °C, P = 30 MPa, CoS = 4 g/min). Some bioactive sesquiterpenoids such as 7-hydroxycadalene, caryophyllene and δ-cadinene were identified in the extracts by GC/MS. The fatty acid profile revealed that the main components were palmitic acid (C16:0), followed by linoleic acid (C18:2ω6c), α-linolenic acid (C18:3ω3) and stearic acid (C18:0) differing in percent yield per treatment. Antibacterial activities were determined by the agar diffusion method, indicating that all the treatments exerted strong antibacterial activity against S. aureus, C. albicans, and E. coli strains. The antioxidant capacity of the extracts was also measured by three in vitro assays, DPPH, TEAC and FRAP, using Trolox as a standard. Results showed high antioxidant capacity enabling pharmaceutical applications of Mexican arnica.

Identification of Bioactivity, Volatile and Fatty Acid Profile in Supercritical Fluid Extracts of Mexican arnica

PubMed Central

García-Pérez, J. Saúl; Cuéllar-Bermúdez, Sara P.; Arévalo-Gallegos, Alejandra; Rodríguez-Rodríguez, José; Iqbal, Hafiz M. N.; Parra-Saldivar, Roberto

2016-01-01

Supercritical fluid extraction (SFE) is a sustainable technique used for the extraction of lipophilic metabolites such as pigments and fatty acids. Arnica plant is considered a potential candidate material with high antioxidant and antimicrobial activities. Therefore, in this study, a locally available Heterotheca inuloides, also known as Mexican arnica, was analyzed for the extraction of high-value compounds. Based on different pressure (P), temperature (T), and co-solvent (CoS), four treatments (T) were prepared. A maximum 7.13% yield was recovered from T2 (T = 60 °C, P = 10 MPa, CoS = 8 g/min), followed by 6.69% from T4 (T = 60 °C, P = 30 MPa, CoS = 4 g/min). Some bioactive sesquiterpenoids such as 7-hydroxycadalene, caryophyllene and δ-cadinene were identified in the extracts by GC/MS. The fatty acid profile revealed that the main components were palmitic acid (C16:0), followed by linoleic acid (C18:2ω6c), α-linolenic acid (C18:3ω3) and stearic acid (C18:0) differing in percent yield per treatment. Antibacterial activities were determined by the agar diffusion method, indicating that all the treatments exerted strong antibacterial activity against S. aureus, C. albicans, and E. coli strains. The antioxidant capacity of the extracts was also measured by three in vitro assays, DPPH, TEAC and FRAP, using Trolox as a standard. Results showed high antioxidant capacity enabling pharmaceutical applications of Mexican arnica. PMID:27626416

Metabolic profiling of Zingiber zerumbet following Pythium myriotylum infection: investigations on the defensive role of the principal secondary metabolite, zerumbone.

PubMed

Keerthi, D; Geethu, C; Nair, R Aswati; Pillai, Padmesh

2014-03-01

Induced biosynthesis of bioactive secondary metabolites constitutes one of the mechanisms of plant basal innate immunity to fungal infection. Metabolic changes were studied in rhizomes of Zingiber zerumbet, a wild congener of ginger, after infection with soft rot-causative necrotrophic phytopathogen, Pythium myriotylum, by gas chromatography-mass spectrometry (GC-MS) analysis. Infection triggered a considerable alteration in the relative content of zerumbone and α-caryophyllene (humulene) with enhancement in zerumbone content (81.59%) and that of α-caryophyllene (11.91%) compared to 9.97 and 1.11%, respectively, in uninfected rhizomes. While zerumbone is the principal secondary metabolite in Z. zerumbet, α-caryophyllene is its immediate precursor. Principal component analysis (PCA) identified the correlations between metabolite changes in Z. zerumbet rhizomes and P. myriotylum infection. Radial diffusion assay with zerumbone indicated a concentration-dependent P. myriotylum growth inhibition with 93.75% inhibition observed at 700 μg and 50% maximal effective concentration (EC50) value of 206 μg. Scanning electron microscopy (SEM) analysis revealed that the mechanistic basis of zerumbone's antagonistic action on P. myriotylum growth involved the induction of aberrant morphology including severe hyphal deformities and membrane disruption. Results are discussed highlighting the critical role played by sesquiterpenoid zerumbone in affording resistance in Z. zerumbet and could expedite the development of appropriate strategies for biocontrol of Pythium spp., thus reducing the usage of broad-spectrum fungicides.

Heterologous expression of cytotoxic sesquiterpenoids from the medicinal mushroom Lignosus rhinocerotis in yeast.

PubMed

Yap, Hui-Yeng Yeannie; Muria-Gonzalez, Mariano Jordi; Kong, Boon-Hong; Stubbs, Keith A; Tan, Chon-Seng; Ng, Szu-Ting; Tan, Nget-Hong; Solomon, Peter S; Fung, Shin-Yee; Chooi, Yit-Heng

2017-06-12

Genome mining facilitated by heterologous systems is an emerging approach to access the chemical diversity encoded in basidiomycete genomes. In this study, three sesquiterpene synthase genes, GME3634, GME3638, and GME9210, which were highly expressed in the sclerotium of the medicinal mushroom Lignosus rhinocerotis, were cloned and heterologously expressed in a yeast system. Metabolite profile analysis of the yeast culture extracts by GC-MS showed the production of several sesquiterpene alcohols (C 15 H 26 O), including cadinols and germacrene D-4-ol as major products. Other detected sesquiterpenes include selina-6-en-4-ol, β-elemene, β-cubebene, and cedrene. Two purified major compounds namely (+)-torreyol and α-cadinol synthesised by GME3638 and GME3634 respectively, are stereoisomers and their chemical structures were confirmed by 1 H and 13 C NMR. Phylogenetic analysis revealed that GME3638 and GME3634 are a pair of orthologues, and are grouped together with terpene synthases that synthesise cadinenes and related sesquiterpenes. (+)-Torreyol and α-cadinol were tested against a panel of human cancer cell lines and the latter was found to exhibit selective potent cytotoxicity in breast adenocarcinoma cells (MCF7) with IC 50 value of 3.5 ± 0.58 μg/ml while α-cadinol is less active (IC 50  = 18.0 ± 3.27 μg/ml). This demonstrates that yeast-based genome mining, guided by transcriptomics, is a promising approach for uncovering bioactive compounds from medicinal mushrooms.

Ultra high performance liquid chromatography coupled with electrospray ionization/quadrupole time-of-flight mass spectrometry for the rapid analysis of constituents in the traditional Chinese medicine formula Wu Ji Bai Feng Pill.

PubMed

Duan, Shengnan; Qi, Wen; Zhang, Siwen; Huang, Kunkun; Yuan, Dan

2017-10-01

An ultra high performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight mass spectrometry method in both positive and negative ion modes was established in order to comprehensively investigate the major constituents in Wu Ji Bai Feng Pill. Briefly, a Waters ACQUITY UPLC HSS C 18 column was used to separate the aqueous extract of Wu Ji Bai Feng Pill. A total of 0.1% formic acid in acetonitrile and 0.1% aqueous formic acid v/v were used as the mobile phase. All analytes were determined using quadrupole time-of-flight mass spectrometry with electrospray ionization source in positive and negative ion modes. At length, a total of 173 components including flavones and their glycosides, monoterpene glycosides, triterpene saponins, phenethylalchohol glycosides, iridoid glycosides, phthalides, tanshinones, phenolic acids, sesquiterpenoids and cyclopeptides were identified or tentatively characterized in Wu Ji Bai Feng Pill in an analysis of 16.0 min based on the accurate mass and tandem mass spectrometry behaviors. The developed method is rapid and highly sensitive to characterize the chemical constituents of Wu Ji Bai Feng Pill, which could not only be used for chemical standardization and quality control of Wu Ji Bai Feng Pill, but also be helpful for further study in vivo metabolism of Wu Ji Bai Feng Pill. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Plectranthus amboinicus (Lour.) Spreng: Botanical, Phytochemical, Pharmacological and Nutritional Significance.

PubMed

Arumugam, Greetha; Swamy, Mallappa Kumara; Sinniah, Uma Rani

2016-03-30

Plectranthus amboinicus (Lour.) Spreng. is a perennial herb belonging to the family Lamiaceae which occurs naturally throughout the tropics and warm regions of Africa, Asia and Australia. This herb has therapeutic and nutritional properties attributed to its natural phytochemical compounds which are highly valued in the pharmaceutical industry. Besides, it has horticultural properties due to its aromatic nature and essential oil producing capability. It is widely used in folk medicine to treat conditions like cold, asthma, constipation, headache, cough, fever and skin diseases. The leaves of the plant are often eaten raw or used as flavoring agents, or incorporated as ingredients in the preparation of traditional food. The literature survey revealed the occurrence 76 volatiles and 30 non-volatile compounds belonging to different classes of phytochemicals such as monoterpenoids, diterpenoids, triterpenoids, sesquiterpenoids, phenolics, flavonoids, esters, alcohols and aldehydes. Studies have cited numerous pharmacological properties including antimicrobial, antiinflammatory, antitumor, wound healing, anti-epileptic, larvicidal, antioxidant and analgesic activities. Also, it has been found to be effective against respiratory, cardiovascular, oral, skin, digestive and urinary diseases. Yet, scientific validation of many other traditional uses would be appreciated, mainly to discover and authenticate novel bioactive compounds from this herb. This review article provides comprehensive information on the botany, phytochemistry, pharmacology and nutritional importance of P. amboinicus essential oil and its various solvent extracts. This article allows researchers to further explore the further potential of this multi-utility herb for various biomedical applications.

Phytochemical analysis of Pinus eldarica bark

PubMed Central

Iravani, S.; Zolfaghari, B.

2014-01-01

Bark extract of Pinus pinaster contains numerous phenolic compounds such as catechins, taxifolin, and phenolic acids. These compounds have received considerable attentions because of their anti-inflammatory, antimutagenic, anticarcinogenic, antimetastatic and high antioxidant activities. Although P. pinaster bark has been intensely investigated in the past; there is comparably less information available in the literature in regard to P. eldarica bark. Therefore, the aim of this study was to determine the chemical composition of P. eldarica commonly found in Iran. A reversed-phase high pressure liquid chromatography (RP-HPLC) method for the determination of catechin, caffeic acid, ferulic acid, and taxifolin in P. pinaster and P. eldarica was developed. A mixture of 0.1% formic acid in deionized water and 0.1% formic acid in acetonitrile was used as the mobile phase, and chromatographic separation was achieved on a Nova pack C18 at 280 nm. The two studied Pinus species contained high amounts of polyphenolic compounds. Among four marker compounds, the main substances identified in P. pinaster and P. eldarica were taxifolin and catechin, respectively. Furthermore, the composition of the bark oil of P. eldarica obtained by hydrodistillation was analyzed by gas chromatography/mass spectroscopy (GC/MS). Thirty-three compounds accounting for 95.1 % of the oil were identified. The oils consisted mainly of mono- and sesquiterpenoid fractions, especially α-pinene (24.6%), caryophyllene oxide (14.0%), δ-3-carene (10.7%), (E)-β-caryophyllene (7.9%), and myrtenal (3.1%). PMID:25657795

Spatial and temporal patterns of floral scent emission in Dianthus inoxianus and electroantennographic responses of its hawkmoth pollinator.

PubMed

Balao, Francisco; Herrera, Javier; Talavera, Salvador; Dötterl, Stefan

2011-05-01

Scent emission is important in nocturnal pollination systems, and plant species pollinated by nocturnal insects often present characteristic odor compositions and temporal patterns of emission. We investigated the temporal (day/night; flower lifetime) and spatial (different flower parts, nectar) pattern of flower scent emission in nocturnally pollinated Dianthusinoxianus, and determined which compounds elicit physiological responses on the antennae of the sphingid pollinator Hyles livornica. The scent of D.inoxianus comprises 68 volatile compounds, but is dominated by aliphatic 2-ketones and sesquiterpenoids, which altogether make up 82% of collected volatiles. Several major and minor compounds elicit electrophysiological responses in the antennae of H. livornica. Total odor emission does not vary along day and night hours, and neither does along the life of the flower. However, the proportion of compounds eliciting physiological responses varies between day and night. All flower parts as well as nectar release volatiles. The scent of isolated flower parts is dominated by fatty acid derivatives, whereas nectar is dominated by benzenoids. Dissection (= damage) of flowers induced a ca. 20-fold increase in the rate of emission of EAD-active volatiles, especially aliphatic 2-ketones. We suggest that aliphatic 2-ketones might contribute to pollinator attraction in D. inoxianus, even though they have been attributed an insect repellent function in other plant species. We also hypothesize that the benzenoids in nectar may act as an honest signal ('nectar guide') for pollinators. Copyright © 2011 Elsevier Ltd. All rights reserved.

Volatile Compounds from the Different Organs of Houttuynia cordata and Litsea cubeba (L. citriodora).

PubMed

Asakawa, Yoshinori; Tomiyama, Kenichi; Sakurai, Kazutoshi; Kawakami, Yukihiro; Yaguchi, Yoshihiro

2017-08-01

The volatile compounds obtained from the different organs of Houttuynia cordata (Saururaceae) and Litsea cubeba (Lauraceae) were analyzed by Gas Chromatography/Mass Spectrometry (GC/MS), Headspace Solid Phase Micro Extraction-Gas Chromatography/Mass Spectrometry (HS-SPME-GC/MS), and GC/olfactometry (GC/O). The major component of all parts of H. cordata is assigned as 4-tridecanone. Each organ produces myrcene as the major monoterpenoid. The major monoterpene in the rhizomes and roots was β-pinene instead of myrcene. 1-Decanal which was responsible for the unpleasant odor of this plant, was the predominant polyketide in both leaves and stems. The presence of 1-decanal was very poor in flowers, stem collected in summer, rhizomes, and roots. GC/MS analyses were very simple in case of the crude extracts of flowers. The content of sesquiterpenoids was extremely poor. (8Z)-Heptadecene, geranial, and neral were detected as the major components in Litsea cubeba. Odor-contributing components by GC/O analysis of the ether extract of the fresh flowers of L. cubeba were neral and geranial which played an important role in sweet-lemon fragrance of the flowers. The role of a high content of (8Z)-heptadecene was still unknown but it might play a significant role in the dispersion of the volatile monoterpene hydrocarbons and aldehydes. The flower volatiles of the Japanese L. cubeba were chemically quite different from those of the Chinese same species.

Mechanisms regulating nutrition-dependent developmental plasticity through organ-specific effects in insects

PubMed Central

Koyama, Takashi; Mendes, Cláudia C.; Mirth, Christen K.

2013-01-01

Nutrition, via the insulin/insulin-like growth factor (IIS)/Target of Rapamycin (TOR) signaling pathway, can provide a strong molding force for determining animal size and shape. For instance, nutrition induces a disproportionate increase in the size of male horns in dung and rhinoceros beetles, or mandibles in staghorn or horned flour beetles, relative to body size. In these species, well-fed male larvae produce adults with greatly enlarged horns or mandibles, whereas males that are starved or poorly fed as larvae bear much more modest appendages. Changes in IIS/TOR signaling plays a key role in appendage development by regulating growth in the horn and mandible primordia. In contrast, changes in the IIS/TOR pathway produce minimal effects on the size of other adult structures, such as the male genitalia in fruit flies and dung beetles. The horn, mandible and genitalia illustrate that although all tissues are exposed to the same hormonal environment within the larval body, the extent to which insulin can induce growth is organ specific. In addition, the IIS/TOR pathway affects body size and shape by controlling production of metamorphic hormones important for regulating developmental timing, like the steroid molting hormone ecdysone and sesquiterpenoid hormone juvenile hormone. In this review, we discuss recent results from Drosophila and other insects that highlight mechanisms allowing tissues to differ in their sensitivity to IIS/TOR and the potential consequences of these differences on body size and shape. PMID:24133450

Prolonged exposure to salt stress affects specialized metabolites-artemisinin and essential oil accumulation in Artemisia annua L.: metabolic acclimation in preferential favour of enhanced terpenoid accumulation accompanying vegetative to reproductive phase transition.

PubMed

Yadav, Ritesh Kumar; Sangwan, Rajender Singh; Srivastava, Avadesh K; Sangwan, Neelam S

2017-01-01

Artemisia annua accumulates substantial quantities of unique and highly useful antimalarial sesquiternoid artemisinin and related phytomolecules as well as its characteristic essential oil in its glandular trichomes. The phytomolecules are mainly produced in its leaves and inflorescences. Artemisia annua plants were grown under NaCl salinity (50, 100 and 200 mM) stress conditions imposed throughout the entire life cycle of the plant. Results revealed that specialized metabolites like artemisinin, arteannuin-B, artemisinic acid + dihydroartemisinic acid and essential oil accumulation were positively modulated by NaCl salinity stress. Interestingly, total content of monoterpenoids and sesquiterpenoids of essential oil was induced by NaCl salinity treatment, contrary to previous observations. Production of camphor, the major essential oil constituent was induced under the influence of treatment. The metabolic acclimation and manifestations specific to terpenoid pathway are analysed vis-a-vis vegetative to reproductive periods and control of the modulation. WRKY and CYP71AV1 play a key role in mediating the responses through metabolism in glandular trichomes. The distinctness of the salinity induced responses is discussed in light of differential mechanism of adaptation to abiotic stresses and their impact on terpenoid-specific metabolic adjustments in A. annua. Results provide potential indications of possible adaptation of A. annua under saline conditions for agrarian techno-economic benefaction.

Cannabis Pharmacology: The Usual Suspects and a Few Promising Leads.

PubMed

Russo, Ethan B; Marcu, Jahan

2017-01-01

The golden age of cannabis pharmacology began in the 1960s as Raphael Mechoulam and his colleagues in Israel isolated and synthesized cannabidiol, tetrahydrocannabinol, and other phytocannabinoids. Initially, THC garnered most research interest with sporadic attention to cannabidiol, which has only rekindled in the last 15 years through a demonstration of its remarkably versatile pharmacology and synergy with THC. Gradually a cognizance of the potential of other phytocannabinoids has developed. Contemporaneous assessment of cannabis pharmacology must be even far more inclusive. Medical and recreational consumers alike have long believed in unique attributes of certain cannabis chemovars despite their similarity in cannabinoid profiles. This has focused additional research on the pharmacological contributions of mono- and sesquiterpenoids to the effects of cannabis flower preparations. Investigation reveals these aromatic compounds to contribute modulatory and therapeutic roles in the cannabis entourage far beyond expectations considering their modest concentrations in the plant. Synergistic relationships of the terpenoids to cannabinoids will be highlighted and include many complementary roles to boost therapeutic efficacy in treatment of pain, psychiatric disorders, cancer, and numerous other areas. Additional parts of the cannabis plant provide a wide and distinct variety of other compounds of pharmacological interest, including the triterpenoid friedelin from the roots, canniprene from the fan leaves, cannabisin from seed coats, and cannflavin A from seed sprouts. This chapter will explore the unique attributes of these agents and demonstrate how cannabis may yet fulfil its potential as Mechoulam's professed "pharmacological treasure trove." © 2017 Elsevier Inc. All rights reserved.

Room temperature ionic liquids: new GC stationary phases with a novel selectivity for flavor and fragrance analyses.

PubMed

Cagliero, Cecilia; Bicchi, Carlo; Cordero, Chiara; Liberto, Erica; Sgorbini, Barbara; Rubiolo, Patrizia

2012-12-14

Ionic liquids (ILs) are of great interest as moderately polar to polar stationary phases for GC, because their selectivity differs markedly from that of conventionally used phases. In the flavor, fragrance and essential oil fields, analysts often deal with complex mixtures of compounds having similar structural and physical characteristics (e.g., mono- and sesquiterpenoids), therefore requiring an interactive combination between chromatographic and mass spectral data for correct identification. New GC stationary phases with different selectivity must therefore be continually tested. Performance and evolution over time of commercially available IL columns versus those commonly used in these fields are here evaluated, mainly in view of their routine use. Chromatographic and separative properties (efficiency, separation capability, inertness and/or activity) of commercially available IL columns were compared to those of columns coated with 5% phenyl-95% methylpolysiloxane, 14% cyanopropyl-86% polysiloxane, and polyethylene glycol, on different complexity samples, including standard mixtures of volatile suspected allergens and pesticides, and cornmint and vetiver essential oils. The results show that IL columns can successfully be used for a wide range of applications characteristic of these fields, mainly because of their unusual selectivity, in particular when separations based on functional groups are required. Moreover, the latest generation of IL columns (IL61 and IL60) presents chromatographic performance comparable to or only slightly lower than that of the conventional columns routinely used in these fields. Copyright © 2012 Elsevier B.V. All rights reserved.

Developmentally Regulated Sesquiterpene Production Confers Resistance to Colletotrichum gloeosporioides in Ripe Pepper Fruits

PubMed Central

Im, Soonduk; Han, Yun-Jeong; Lee, Sungbeom; Back, Kyoungwhan; Kim, Jeong-Il; Kim, Young Soon

2014-01-01

Sesquiterpenoid capsidiol, exhibiting antifungal activity against pathogenic fungus, is accumulated in infected ripe pepper fruits. In this study, we found a negative relation between the capsidiol level and lesion size in fruits infected with Colletotrichum gloeosporioides, depending on the stage of ripening. To understand the developmental regulation of capsidiol biosynthesis, fungal-induced gene expressions in the isoprenoid biosynthetic pathways were examined in unripe and ripe pepper fruits. The sterol biosynthetic pathway was almost shut down in healthy ripe fruits, showing very low expression of hydroxymethyl glutaryl CoA reductase (HMGR) and squalene synthase (SS) genes. In contrast, genes in the carotenoid pathway were highly expressed in ripe fruits. In the sesquiterpene pathway, 5-epi-aristolochene synthase (EAS), belonging to a sesquiterpene cyclase (STC) family, was significantly induced in the ripe fruits upon fungal infection. Immunoblot and enzyme activity analyses showed that the STCs were induced both in the infected unripe and ripe fruits, while capsidiol was synthesized discriminatively in the ripe fruits, implying diverse enzymatic specificity of multiple STCs. Thereby, to divert sterol biosynthesis into sesquiterpene production, infected fruits were pretreated with an SS inhibitor, zaragozic acid (ZA), resulting in increased levels of capsidiol by more than 2-fold in the ripe fruits, with concurrent reduction of phytosterols. Taken together, the present results suggest that the enhanced expression and activity of EAS in the ripe fruits play an important role in capsidiol production, contributing to the incompatibility between the anthracnose fungus and the ripe pepper fruits. PMID:25286411

The Full-Size ABCG Transporters Nb-ABCG1 and Nb-ABCG2 Function in Pre- and Postinvasion Defense against Phytophthora infestans in Nicotiana benthamiana

PubMed Central

Shibata, Yusuke; Ojika, Makoto; Sugiyama, Akifumi; Yazaki, Kazufumi; Jones, David A.; Kawakita, Kazuhito

2016-01-01

The sesquiterpenoid capsidiol is the major phytoalexin produced by Nicotiana and Capsicum species. Capsidiol is produced in plant tissues attacked by pathogens and plays a major role in postinvasion defense by inhibiting pathogen growth. Using virus-induced gene silencing-based screening, we identified two Nicotiana benthamiana (wild tobacco) genes encoding functionally redundant full-size ABCG (PDR-type) transporters, Nb-ABCG1/PDR1 and Nb-ABCG2/PDR2, which are essential for resistance to the potato late blight pathogen Phytophthora infestans. Silencing of Nb-ABCG1/2 compromised secretion of capsidiol, revealing Nb-ABCG1/2 as probable exporters of capsidiol. Accumulation of plasma membrane-localized Nb-ABCG1 and Nb-ABCG2 was observed at the site of pathogen penetration. Silencing of EAS (encoding 5-epi-aristolochene synthase), a gene for capsidiol biosynthesis, reduced resistance to P. infestans, but penetration by P. infestans was not affected. By contrast, Nb-ABCG1/2-silenced plants showed reduced penetration defense, indicating that Nb-ABCG1/2 are involved in preinvasion defense against P. infestans. Plastidic GGPPS1 (geranylgeranyl diphosphate synthase) was also found to be required for preinvasion defense, thereby suggesting that plastid-produced diterpene(s) are the antimicrobial compounds active in preinvasion defense. These findings suggest that N. benthamiana ABCG1/2 are involved in the export of both antimicrobial diterpene(s) for preinvasion defense and capsidiol for postinvasion defense against P. infestans. PMID:27102667

[Chemical composition of essential oils from leaves of Helicteres guazumifolia (Sterculiaceae), Piper tuberculatum (Piperaceae), Scoparia dulcis (Arecaceae) and Solanum subinerme (Solanaceae) from Sucre, Venezuela].

PubMed

Ordaz, Gabriel; D'Armas, Haydelba; Yáñez, Dayanis; Moreno, Shailili

2011-06-01

Essential oils, biosynthesized and accumulated in aromatic plants, have a wide range of applications in the pharmaceutical health, cosmetics, food and agricultural industry. This study aimed to analyze the secondary metabolites in some plant species in order to contribute to their chemotaxonomy. Leaves from Helicteres guazumifolia, Piper tuberculatum, Scoparia dulcis and Solanum subinerme were collected and their essential oils were obtained by means of hydro-distillation. The oil fraction was analyzed and identified by GC/MS. The extraction yields were of 0.004, 0.032, 0.016 and 0.005%, and the oil constituents of 88.00, 89.80, 87.50 and 89.47%, respectively. The principal oils found were: non-terpenoids volatile secondary metabolites (30.28%) in H. guazumifolia; sesquiterpenoids (20.82 and 26.09%) and oxigen derivated (52.19 and 25.18%) in P. tuberculatum and S. dulcis; and oxigen diterpenoids (39.67%) in S. subinerme. The diisobuthylphtalate (13.11%) in H. guazumifolia, (-)-spathulenol (11.37%) in P. tuberculatum and trans-phytol (8.29 and 36.00%) in S. dulcis and S. subinerme, were the principal constituents in their respective essential oils. The diisooctylphtalate were the essential oil common to all species, but the volatile compounds such as trans-pinane, L-linalool, beta-ionone, isophytol, neophytadiene, trans-phytol, dibutylphtalate and methyl hexadecanoate, were only detected in three of these essences. This suggests that these plants may require similar secondary metabolites for their ecological interactions, possibly due to common environmental factors.

Inhibition of Klebsiella pneumoniae growth by selected Australian plants: natural approaches for the prevention and management of ankylosing spondylitis.

PubMed

Winnett, V; Sirdaarta, J; White, A; Clarke, F M; Cock, I E

2017-04-01

A wide variety of herbal remedies are used in traditional Australian medicine to treat inflammatory disorders, including autoimmune inflammatory diseases. One hundred and six extracts from 40 native Australian plant species traditionally used for the treatment of inflammation and/or to inhibit bacterial growth were investigated for their ability to inhibit the growth of a microbial trigger for ankylosing spondylitis (K. pneumoniae). Eighty-six of the extracts (81.1%) inhibited the growth of K. pneumoniae. The D. leichardtii, Eucalyptus spp., K. flavescens, Leptospermum spp., M. quinquenervia, Petalostigma spp., P. angustifolium, S. spinescens, S. australe, S. forte and Tasmannia spp. extracts were effective K. pneumoniae growth inhibitors, with MIC values generally <1000 µg/mL. The T. lanceolata peppercorn extracts were the most potent growth inhibitors, with MIC values as low as 16 µg/mL. These extracts were examined by non-biased GC-MS headspace analysis and comparison with a compound database. A notable feature was the high relative abundance of the sesquiterpenoids polygodial, guaiol and caryophyllene oxide, and the monoterpenoids linalool, cineole and α-terpineol in the T. lanceolata peppercorn methanolic and aqueous extracts. The extracts with the most potent K. pneumoniae inhibitory activity (including the T. lanceolata peppercorn extracts) were nontoxic in the Artemia nauplii bioassay. The lack of toxicity and the growth inhibitory activity of these extracts against K. pneumoniae indicate their potential for both preventing the onset of ankylosing spondylitis and minimising its symptoms once the disease is established.

Phytotoxic effects of trichothecenes on the growth and morphology of Arabidopsis thaliana.

PubMed

Masuda, Daisuke; Ishida, Mamoru; Yamaguchi, Kazuo; Yamaguchi, Isamu; Kimura, Makoto; Nishiuchi, Takumi

2007-01-01

Non-volatile sesquiterpenoids, a trichothecene family of phytotoxins such as deoxynivalenol (DON) and T-2 toxin, contain numerous molecular species and are synthesized by phytopathogenic Fusarium species. Although trichothecene chemotypes might play a role in the virulence of individual Fusarium strains, the phytotoxic action of individual trichothecenes has not been systematically studied. To perform a comparative analysis of the phytotoxic action of representative trichothecenes, the growth and morphology of Arabidopsis thaliana growing on media containing these compounds was investigated. Both DON and diacetoxyscirpenol (DAS) preferentially inhibited root elongation. DON-treated roots were less organized compared with control roots. Moreover, preferential inhibition of root growth by DON was also observed in wheat plants. In addition, T-2 toxin-treated seedlings exhibited dwarfism with aberrant morphological changes (e.g. petiole shortening, curled dark-green leaves, and reduced cell size). These results imply that the phytotoxic action of trichothecenes differed among their molecular species. Cycloheximide (CHX)-treated seedlings displayed neither feature, although it is known that trichothecenes inhibit translation in eukaryotic ribosomes. Microarray analyses suggested that T-2 toxin caused a defence response, the inactivation of brassinosteroid (BR), and the generation of reactive oxygen species in Arabidopsis. This observation is in agreement with our previous reports in which trichothecenes such as T-2 toxin have an elicitor-like activity when infiltrated into the leaves of Arabidopsis. Since it has been reported that BR plays an important role in a broad range of disease resistance in tobacco and rice, inactivation of BR might affect pathogenicity during the infection of host plants by trichothecene-producing fungi.

Insights from zebrafish and mouse models on the activity and safety of ar-turmerone as a potential drug candidate for the treatment of epilepsy.

PubMed

Orellana-Paucar, Adriana Monserrath; Afrikanova, Tatiana; Thomas, Joice; Aibuldinov, Yelaman K; Dehaen, Wim; de Witte, Peter A M; Esguerra, Camila V

2013-01-01

In a previous study, we uncovered the anticonvulsant properties of turmeric oil and its sesquiterpenoids (ar-turmerone, α-, β-turmerone and α-atlantone) in both zebrafish and mouse models of chemically-induced seizures using pentylenetetrazole (PTZ). In this follow-up study, we aimed at evaluating the anticonvulsant activity of ar-turmerone further. A more in-depth anticonvulsant evaluation of ar-turmerone was therefore carried out in the i.v. PTZ and 6-Hz mouse models. The potential toxic effects of ar-turmerone were evaluated using the beam walking test to assess mouse motor function and balance. In addition, determination of the concentration-time profile of ar-turmerone was carried out for a more extended evaluation of its bioavailability in the mouse brain. Ar-turmerone displayed anticonvulsant properties in both acute seizure models in mice and modulated the expression patterns of two seizure-related genes (c-fos and brain-derived neurotrophic factor [bdnf]) in zebrafish. Importantly, no effects on motor function and balance were observed in mice after treatment with ar-turmerone even after administering a dose 500-fold higher than the effective dose in the 6-Hz model. In addition, quantification of its concentration in mouse brains revealed rapid absorption after i.p. administration, capacity to cross the BBB and long-term brain residence. Hence, our results provide additional information on the anticonvulsant properties of ar-turmerone and support further evaluation towards elucidating its mechanism of action, bioavailability, toxicity and potential clinical application.

Insights from Zebrafish and Mouse Models on the Activity and Safety of Ar-Turmerone as a Potential Drug Candidate for the Treatment of Epilepsy

PubMed Central

Orellana-Paucar, Adriana Monserrath; Afrikanova, Tatiana; Thomas, Joice; Aibuldinov, Yelaman K.; Dehaen, Wim; de Witte, Peter A. M.; Esguerra, Camila V.

2013-01-01

In a previous study, we uncovered the anticonvulsant properties of turmeric oil and its sesquiterpenoids (ar-turmerone, α-, β-turmerone and α-atlantone) in both zebrafish and mouse models of chemically-induced seizures using pentylenetetrazole (PTZ). In this follow-up study, we aimed at evaluating the anticonvulsant activity of ar-turmerone further. A more in-depth anticonvulsant evaluation of ar-turmerone was therefore carried out in the i.v. PTZ and 6-Hz mouse models. The potential toxic effects of ar-turmerone were evaluated using the beam walking test to assess mouse motor function and balance. In addition, determination of the concentration-time profile of ar-turmerone was carried out for a more extended evaluation of its bioavailability in the mouse brain. Ar-turmerone displayed anticonvulsant properties in both acute seizure models in mice and modulated the expression patterns of two seizure-related genes (c-fos and brain-derived neurotrophic factor [bdnf]) in zebrafish. Importantly, no effects on motor function and balance were observed in mice after treatment with ar-turmerone even after administering a dose 500-fold higher than the effective dose in the 6-Hz model. In addition, quantification of its concentration in mouse brains revealed rapid absorption after i.p. administration, capacity to cross the BBB and long-term brain residence. Hence, our results provide additional information on the anticonvulsant properties of ar-turmerone and support further evaluation towards elucidating its mechanism of action, bioavailability, toxicity and potential clinical application. PMID:24349101

Mechanism-based inactivation of CYP2C9 by linderane.

PubMed

Wang, Hui; Wang, Kai; Mao, Xu; Zhang, Qingqing; Yao, Tong; Peng, Ying; Zheng, Jiang

2015-01-01

1. Linderane (LDR), a furan-containing sesquiterpenoid, is found in Lindera aggregata (Sims) Kosterm, a common traditional Chinese herbal medicine. We thoroughly studied the irreversible inhibitory effect of LDR on cytochrome P450 2C9 (CYP2C9). 2. LDR caused a time- and concentration-dependent inactivation of CYP2C9. In addition, the inactivation of CYP2C9 by LDR was NADPH-dependent and irreversible. More than 50% of CYP2C9 activity was lost after its incubation with LDR at the concentration of 10 μM for 15 min at 30 °C. The maximal rate constant for inactivation (kinact) was found to be 0.0419 min(-1), and the concentration required for half-maximal inactivation (KI) was 1.26 μM, respectively. Glutathione (GSH), catalase, and superoxide dismutase (SOD) failed to protect CYP2C9 against inactivation by LDR. Diclofenac, a substrate of CYP2C9, prevented the enzyme from inactivation produced by LDR. The estimated partition ratio of the inactivation was approximately 227. 3. Two reactive intermediates, including furanoepoxide and γ-ketoenal, might be responsible for the observed enzyme inactivation. The formation of the intermediates was verified by chemical synthesis. Multiple P450 enzymes, including CYPs 1A2, 2B6, 2C9, 2C19, 2D6, 3A4, and 3A5, were found to be involved in the metabolic activation of LDR. In conclusion, LDR was characterized as a mechanism-based inactivator of CYP2C9.

Determination of the molecular signature of fossil conifers by experimental palaeochemotaxonomy - Part 1: The Araucariaceae family

NASA Astrophysics Data System (ADS)

Lu, Y.; Hautevelle, Y.; Michels, R.

2012-08-01

Several extant species of the Araucariaceae family (one of the families of conifers) were invested for the experimental artificial maturation by confined pyrolysis, in order to realize the transformation of biomolecules to geomolecules in laboratory conditions. The experimental study of diagenetized molecular signatures of the Araucariaceae species (common, inter- and infra-generic characteristics) allow to complete our knowledge in botanical palaeochemotaxonomy. Such knowledge is relevant to the reconstitution of palaeoflora and palaeoclimatic reconstruction, archaeology and environmental studies. In this work, major carbon skeleton types of Araucariaceae are detected in the organic solvent extracts of fresh and pyrolyzed plants using gas chromatography-mass spectrometry. The results show that all species of Araucariaceae are firstly characterized by a predominance of saturated tetracyclic diterpenoids. Moreover, the Araucaria genus shows a high relative abundance of bicyclic sesquiterpenoids, particularly compounds of the cadalane-type compounds accompanied by those of eudesmane-type, bisabolane-type as well as chamazulene, pentamethyl-dihydroindenes. Diterpenoids are of the labdane-type, isopimarane, abietane-type (essentially derived from abietanoic acids) as well as isohexyl alkylaromatic hydrocarbons. Compared to the tetracyclic diterpenoids, these compounds show a relatively lower abundance, reaching trace levels in the case of saturated abietanes. Distribution of sesqui- and diterpenoids of Agathis shows some similarities to that of Araucaria, with the exception of one species, in which the tetracyclic compounds are absent and the abietane-type (essentially derived from abietanoic acids) predominant. High similarities between the Wollemia and Araucaria genera are observed. Both are characterized by some high relative abundance of tetracyclic compounds with no predominance of other specific diterpenoids.

Extracting the Behaviorally Relevant Stimulus: Unique Neural Representation of Farnesol, a Component of the Recruitment Pheromone of Bombus terrestris

PubMed Central

Strube-Bloss, Martin F.; Brown, Austin; Spaethe, Johannes; Schmitt, Thomas; Rössler, Wolfgang

2015-01-01

To trigger innate behavior, sensory neural networks are pre-tuned to extract biologically relevant stimuli. Many male-female or insect-plant interactions depend on this phenomenon. Especially communication among individuals within social groups depends on innate behaviors. One example is the efficient recruitment of nest mates by successful bumblebee foragers. Returning foragers release a recruitment pheromone in the nest while they perform a ‘dance’ behavior to activate unemployed nest mates. A major component of this pheromone is the sesquiterpenoid farnesol. How farnesol is processed and perceived by the olfactory system, has not yet been identified. It is much likely that processing farnesol involves an innate mechanism for the extraction of relevant information to trigger a fast and reliable behavioral response. To test this hypothesis, we used population response analyses of 100 antennal lobe (AL) neurons recorded in alive bumblebee workers under repeated stimulation with four behaviorally different, but chemically related odorants (geraniol, citronellol, citronellal and farnesol). The analysis identified a unique neural representation of the recruitment pheromone component compared to the other odorants that are predominantly emitted by flowers. The farnesol induced population activity in the AL allowed a reliable separation of farnesol from all other chemically related odor stimuli we tested. We conclude that the farnesol induced population activity may reflect a predetermined representation within the AL-neural network allowing efficient and fast extraction of a behaviorally relevant stimulus. Furthermore, the results show that population response analyses of multiple single AL-units may provide a powerful tool to identify distinct representations of behaviorally relevant odors. PMID:26340263

Enzymatic synthesis of valerena-4,7(11)-diene by a unique sesquiterpene synthase from the valerian plant (Valeriana officinalis).

PubMed

Pyle, Bryan W; Tran, Hue T; Pickel, Benjamin; Haslam, Tegan M; Gao, Zhizeng; MacNevin, Gillian; Vederas, John C; Kim, Soo-Un; Ro, Dae-Kyun

2012-09-01

Valerian (Valeriana officinalis) is a popular medicinal plant in North America and Europe. Its root extract is commonly used as a mild sedative and anxiolytic. Among dozens of chemical constituents (e.g. alkaloids, iridoids, flavonoids, and terpenoids) found in valerian root, valerena-4,7(11)-diene and valerenic acid (C15 sesquiterpenoid) have been suggested as the active ingredients responsible for the sedative effect. However, the biosynthesis of the valerena-4,7(11)-diene hydrocarbon skeleton in valerian remains unknown to date. To identify the responsible terpene synthase, next-generation sequencing (Roche 454 pyrosequencing) was used to generate ∼ 1 million transcript reads from valerian root. From the assembled transcripts, two sesquiterpene synthases were identified (VoTPS1 and VoTPS2), both of which showed predominant expression patterns in root. Transgenic yeast expressing VoTPS1 and VoTPS2 produced germacrene C/germacrene D and valerena-4,7(11)-diene, respectively, as major terpene products. Purified VoTPS1 and VoTPS2 recombinant enzymes confirmed these activities in vitro, with competent kinetic properties (K(m) of ∼ 10 μm and k(cat) of 0.01 s(-1) for both enzymes). The structure of the valerena-4,7(11)-diene produced from the yeast expressing VoTPS2 was further substantiated by (13) C-NMR and GC-MS in comparison with the synthetic standard. This study demonstrates an integrative approach involving next-generation sequencing and metabolically engineered microbes to expand our knowledge of terpenoid diversity in medicinal plants. © 2012 The Authors Journal compilation © 2012 FEBS.

Effects of Trichothecene Production on the Plant Defense Response and Fungal Physiology: Overexpression of the Trichoderma arundinaceum tri4 Gene in T. harzianum.

PubMed

Cardoza, R E; McCormick, S P; Malmierca, M G; Olivera, E R; Alexander, N J; Monte, E; Gutiérrez, S

2015-09-01

Trichothecenes are fungal sesquiterpenoid compounds, the majority of which have phytotoxic activity. They contaminate food and feed stocks, resulting in potential harm to animals and human beings. Trichoderma brevicompactum and T. arundinaceum produce trichodermin and harzianum A (HA), respectively, two trichothecenes that show different bioactive properties. Both compounds have remarkable antibiotic and cytotoxic activities, but in addition, trichodermin is highly phytotoxic, while HA lacks this activity when analyzed in vivo. Analysis of Fusarium trichothecene intermediates led to the conclusion that most of them, with the exception of the hydrocarbon precursor trichodiene (TD), have a detectable phytotoxic activity which is not directly related to the structural complexity of the intermediate. In the present work, the HA intermediate 12,13-epoxytrichothec-9-ene (EPT) was produced by expression of the T. arundinaceum tri4 gene in a transgenic T. harzianum strain that already produces TD after transformation with the T. arundinaceum tri5 gene. Purified EPT did not show antifungal or phytotoxic activity, while purified HA showed both antifungal and phytotoxic activities. However, the use of the transgenic T. harzianum tri4 strain induced a downregulation of defense-related genes in tomato plants and also downregulated plant genes involved in fungal root colonization. The production of EPT by the transgenic tri4 strain raised levels of erg1 expression and reduced squalene accumulation while not affecting levels of ergosterol. Together, these results indicate the complex interactions among trichothecene intermediates, fungal antagonists, and host plants. Copyright © 2015, American Society for Microbiology. All Rights Reserved.

Effects of Trichothecene Production on the Plant Defense Response and Fungal Physiology: Overexpression of the Trichoderma arundinaceum tri4 Gene in T. harzianum

PubMed Central

Cardoza, R. E.; McCormick, S. P.; Malmierca, M. G.; Olivera, E. R.; Alexander, N. J.; Monte, E.

2015-01-01

Trichothecenes are fungal sesquiterpenoid compounds, the majority of which have phytotoxic activity. They contaminate food and feed stocks, resulting in potential harm to animals and human beings. Trichoderma brevicompactum and T. arundinaceum produce trichodermin and harzianum A (HA), respectively, two trichothecenes that show different bioactive properties. Both compounds have remarkable antibiotic and cytotoxic activities, but in addition, trichodermin is highly phytotoxic, while HA lacks this activity when analyzed in vivo. Analysis of Fusarium trichothecene intermediates led to the conclusion that most of them, with the exception of the hydrocarbon precursor trichodiene (TD), have a detectable phytotoxic activity which is not directly related to the structural complexity of the intermediate. In the present work, the HA intermediate 12,13-epoxytrichothec-9-ene (EPT) was produced by expression of the T. arundinaceum tri4 gene in a transgenic T. harzianum strain that already produces TD after transformation with the T. arundinaceum tri5 gene. Purified EPT did not show antifungal or phytotoxic activity, while purified HA showed both antifungal and phytotoxic activities. However, the use of the transgenic T. harzianum tri4 strain induced a downregulation of defense-related genes in tomato plants and also downregulated plant genes involved in fungal root colonization. The production of EPT by the transgenic tri4 strain raised levels of erg1 expression and reduced squalene accumulation while not affecting levels of ergosterol. Together, these results indicate the complex interactions among trichothecene intermediates, fungal antagonists, and host plants. PMID:26150463

Monitoring the dynamic emission of biogenic volatile organic compounds from Cryptomeria japonica by enclosure measurement

NASA Astrophysics Data System (ADS)

Lin, Chun-Ya; Chang, Tzu-Cheng; Chen, Yu-Han; Chen, Ying-Ju; Cheng, Sen-Sung; Chang, Shang-Tzen

2015-12-01

Research on biogenic volatile organic compounds (BVOCs) emitted from trees is essential in the world since these BVOCs play an important role in the atmospheric process which may further influence on the air quality. However, little is known about BVOCs emitted from trees in the field in Taiwan. Hence, this study intends to establish an enclosure technique coupled with in situ sampling to facilitate the collection of BVOCs emitted from Cryptomeria japonica leaves. Furthermore, the emission model derived from the relationship between emission rate and temperature was applied to estimate the emission of BVOCs in the field. Results from GC-MS showed that the BVOCs emitted from intact leaves contain 14 monoterpenoids and 4 sesquiterpenoid. The emission rate of the major constituent, sabinene, was 0.42 μg h-1 g-1 around noon on September 11, 2013. Sabinene varies with the changing temperature inside the bag. These findings indicated that the enclosure technique can collect the BVOCs emitted from intact leaves and monitor the dynamic changes in emission. Two determinants, basal emission rate (at 30 °C) and β coefficient, of sabinene were further measured, and they were 1.29 μg h-1 g-1 and 0.18 °C-1, respectively. By using these two determinants and data of meteorology and forest resource, the emission of monoterpenes from C. japonica stand was estimated to be 1.13 mg m-2 h-1 in July in Xitou area. Taken together, the results provide valuable information for estimation of BVOCs from tree species in Taiwan for the first time.

Volatiles Emitted from Maize Ears Simultaneously Infected with Two Fusarium Species Mirror the Most Competitive Fungal Pathogen

PubMed Central

Sherif, Mohammed; Becker, Eva-Maria; Herrfurth, Cornelia; Feussner, Ivo; Karlovsky, Petr; Splivallo, Richard

2016-01-01

Along with barley and rice, maize provides staple food for more than half of the world population. Maize ears are regularly infected with fungal pathogens of the Fusarium genus, which, besides reducing yield, also taint grains with toxic metabolites. In an earlier work, we have shown that maize ears infection with single Fusarium strains was detectable through volatile sensing. In nature, infection most commonly occurs with more than a single fungal strain; hence we tested how the interactions of two strains would modulate volatile emission from infected ears. For this purpose, ears of a hybrid and a dwarf maize variety were simultaneously infected with different strains of Fusarium graminearum and F. verticillioides and, the resulting volatile profiles were compared to the ones of ears infected with single strains. Disease severity, fungal biomass, and the concentration of the oxylipin 9-hydroxy octadecadienoic acid, a signaling molecule involved in plant defense, were monitored and correlated to volatile profiles. Our results demonstrate that in simultaneous infections of hybrid and dwarf maize, the most competitive fungal strains had the largest influence on the volatile profile of infected ears. In both concurrent and single inoculations, volatile profiles reflected disease severity. Additionally, the data further indicate that dwarf maize and hybrid maize might emit common (i.e., sesquiterpenoids) and specific markers upon fungal infection. Overall this suggests that volatile profiles might be a good proxy for disease severity regardless of the fungal competition taking place in maize ears. With the appropriate sensitivity and reliability, volatile sensing thus appears as a promising tool for detecting fungal infection of maize ears under field conditions. PMID:27729923

Effect of natural and semi-synthetic cadinanes from Heterotheca inuloides on NF-κB, Nrf2 and STAT3 signaling pathways and evaluation of their in vitro cytotoxicity in human cancer cell lines.

PubMed

Egas, Verónica; Millán, Estrella; Collado, Juan A; Ramírez-Apan, Teresa; Méndez-Cuesta, Carlos A; Muñoz, Eduardo; Delgado, Guillermo

2017-06-15

The effects of ten natural cadinane sesquiterpenoids isolated from Heterotheca inuloides on the pathways of the NF-κB, Nrf2 and STAT3 transcription factors were studied for the first time. The main constituent in this species, 7-hydroxy-3,4-dihydrocadalene (1), showed anti-NF-κB activity and activated the antioxidant Nrf2 pathway, which may explain the properties reported for the traditional use of the plant. In addition to the main metabolite, a structurally similar compound, 7-hydroxy-cadalene (2), also displayed anti-NF-κB activity. Thus, both natural compounds were used as templates for the preparation of a novel semi-synthetic derivative set, including esters and carbamates, which were evaluated for their potential in vitro antiproliferative activities against six human cancer cell lines. Carbamate derivatives 32 and 33 were found to exhibit potent activity against human colorectal adenocarcinoma and showed important selectivity in cancer cells. Among ester derivatives, compound 13 was determined to be a more potent NF-κB inhibitor and Nrf2 activator than its parent, 7-hydroxy-3,4-dihydrocadalene (1). Furthermore, this compound decreases levels of phospho-IκBα, a protein complex involved in the NF-κB activation pathway. Molecular simulations suggest that all active compounds interact with the activation loop of the IKKβ subunit in the IKK complex, which is the responsible of IκBα phosphorylation. Thus, we identified two natural, and one semi-synthetic, NF-κB and Nrf2 modulators and two new promising cytotoxic compounds. Copyright © 2017 Elsevier Ltd. All rights reserved.

Floral scent in natural hybrids of Ipomopsis (Polemoniaceae) and their parental species

PubMed Central

Bischoff, Mascha; Jürgens, Andreas; Campbell, Diane R.

2014-01-01

Background and Aims Floral traits, such as floral volatiles, can contribute to pre-zygotic reproductive isolation by promoting species-specific pollinator foraging. When hybrid zones form, floral traits could also influence post-zygotic isolation. This study examined floral volatiles in parental species and natural hybrids in order to explore potential scent mediation of pre-zygotic and post-zygotic isolation. Methods Floral bouquets were analysed for the sister species Ipomopsis aggregata and I. tenuituba and their natural hybrids at two contact sites differing in both hybridization rate and temporal foraging pattern of hawkmoth pollinators. Floral volatiles were quantified in diurnal and nocturnal scent samples using gas chromatography–mass spectrometry. Key Results The bouquets of parental species and hybrids showed qualitative overlap. All flowers emitted similar sets of monoterpenoid, sesquiterpenoid, aliphatic and benzenoid compounds, but separated into groups defined by multivariate analysis of quantitative emissions. The parental species differed most strikingly in the nitrogenous compound indole, which was found almost exclusively in nocturnal bouquets of I. tenuituba. Natural hybrid bouquets were highly variable, and showed emission rates of several compounds that appeared transgressive. However, indole emission rates were intermediate in the hybrids compared with rates in the parents. Volatile bouquets at the contact site with lower hybridization did not show greater species specificity in overall scent emission, but I. tenuituba presented a stronger indole signal during peak hawkmoth activity at that site. Conclusions The two species of Ipomopsis differed in patterns of floral bouquets, with indole emitted in nocturnal I. tenuituba, but not in I. aggregata. Natural hybrid bouquets were not consistently intermediate between the parents, although hybrids were intermediate in indole emission. The indole signal could potentially serve as a hawkmoth attractant that mediates reproductive isolation both before and after hybrid formation. PMID:24355404

Terpenoid Metabolism in Wild-Type and Transgenic Arabidopsis PlantsW⃞

PubMed Central

Aharoni, Asaph; Giri, Ashok P.; Deuerlein, Stephan; Griepink, Frans; de Kogel, Willem-Jan; Verstappen, Francel W. A.; Verhoeven, Harrie A.; Jongsma, Maarten A.; Schwab, Wilfried; Bouwmeester, Harro J.

2003-01-01

Volatile components, such as terpenoids, are emitted from aerial parts of plants and play a major role in the interaction between plants and their environment. Analysis of the composition and emission pattern of volatiles in the model plant Arabidopsis showed that a range of volatile components are released, primarily from flowers. Most of the volatiles detected were monoterpenes and sesquiterpenes, which in contrast to other volatiles showed a diurnal emission pattern. The active terpenoid metabolism in wild-type Arabidopsis provoked us to conduct an additional set of experiments in which transgenic Arabidopsis overexpressing two different terpene synthases were generated. Leaves of transgenic plants constitutively expressing a dual linalool/nerolidol synthase in the plastids (FaNES1) produced linalool and its glycosylated and hydroxylated derivatives. The sum of glycosylated components was in some of the transgenic lines up to 40- to 60-fold higher than the sum of the corresponding free alcohols. Surprisingly, we also detected the production and emission of nerolidol, albeit at a low level, suggesting that a small pool of its precursor farnesyl diphosphate is present in the plastids. Transgenic lines with strong transgene expression showed growth retardation, possibly as a result of the depletion of isoprenoid precursors in the plastids. In dual-choice assays with Myzus persicae, the FaNES1-expressing lines significantly repelled the aphids. Overexpression of a typical cytosolic sesquiterpene synthase resulted in the production of only trace amounts of the expected sesquiterpene, suggesting tight control of the cytosolic pool of farnesyl diphosphate, the precursor for sesquiterpenoid biosynthesis. This study further demonstrates the value of Arabidopsis for studies of the biosynthesis and ecological role of terpenoids and provides new insights into their metabolism in wild-type and transgenic plants. PMID:14630967

The terpene synthase gene family in Tripterygium wilfordii harbors a labdane-type diterpene synthase among the monoterpene synthase TPS-b subfamily.

PubMed

Hansen, Nikolaj L; Heskes, Allison M; Hamberger, Britta; Olsen, Carl E; Hallström, Björn M; Andersen-Ranberg, Johan; Hamberger, Björn

2017-02-01

Tripterygium wilfordii (Celastraceae) is a medicinal plant with anti-inflammatory and immunosuppressive properties. Identification of a vast array of unusual sesquiterpenoids, diterpenoids and triterpenoids in T. wilfordii has spurred investigations of their pharmacological properties. The tri-epoxide lactone triptolide was the first of many diterpenoids identified, attracting interest due to the spectrum of bioactivities. To probe the genetic underpinning of diterpenoid diversity, an expansion of the class II diterpene synthase (diTPS) family was recently identified in a leaf transcriptome. Following detection of triptolide and simple diterpene scaffolds in the root, we sequenced and mined the root transcriptome. This allowed identification of the root-specific complement of TPSs and an expansion in the class I diTPS family. Functional characterization of the class II diTPSs established their activities in the formation of four C-20 diphosphate intermediates, precursors of both generalized and specialized metabolism and a novel scaffold for Celastraceae. Functional pairs of the class I and II enzymes resulted in formation of three scaffolds, accounting for some of the terpenoid diversity found in T. wilfordii. The absence of activity-forming abietane-type diterpenes encouraged further testing of TPSs outside the canonical class I diTPS family. TwTPS27, close relative of mono-TPSs, was found to couple with TwTPS9, converting normal-copalyl diphosphate to miltiradiene. The phylogenetic distance to established diTPSs indicates neo-functionalization of TwTPS27 into a diTPS, a function not previously observed in the TPS-b subfamily. This example of evolutionary convergence expands the functionality of TPSs in the TPS-b family and may contribute miltiradiene to the diterpenoids of T. wilfordii. © 2016 The Authors The Plant Journal © 2016 John Wiley & Sons Ltd.

S-Carvone Suppresses Cellulase-Induced Capsidiol Production in Nicotiana tabacum by Interfering with Protein Isoprenylation1[C][W

PubMed Central

Huchelmann, Alexandre; Gastaldo, Clément; Veinante, Mickaël; Zeng, Ying; Heintz, Dimitri; Tritsch, Denis; Schaller, Hubert; Rohmer, Michel; Bach, Thomas J.; Hemmerlin, Andréa

2014-01-01

S-Carvone has been described as a negative regulator of mevalonic acid (MVA) production by interfering with 3-hydroxy-3-methyl glutaryl coenzyme A reductase (HMGR) activity, a key player in isoprenoid biosynthesis. The impact of this monoterpene on the production of capsidiol in Nicotiana tabacum, an assumed MVA-derived sesquiterpenoid phytoalexin produced in response to elicitation by cellulase, was investigated. As expected, capsidiol production, as well as early stages of elicitation such as hydrogen peroxide production or stimulation of 5-epi-aristolochene synthase activity, were repressed. Despite the lack of capsidiol synthesis, apparent HMGR activity was boosted. Feeding experiments using (1-13C)Glc followed by analysis of labeling patterns by 13C-NMR, confirmed an MVA-dependent biosynthesis; however, treatments with fosmidomycin, an inhibitor of the MVA-independent 2-C-methyl-d-erythritol 4-phosphate (MEP) isoprenoid pathway, unexpectedly down-regulated the biosynthesis of this sesquiterpene as well. We postulated that S-carvone does not directly inhibit the production of MVA by inactivating HMGR, but possibly targets an MEP-derived isoprenoid involved in the early steps of the elicitation process. A new model is proposed in which the monoterpene blocks an MEP pathway–dependent protein geranylgeranylation necessary for the signaling cascade. The production of capsidiol was inhibited when plants were treated with some inhibitors of protein prenylation or by further monoterpenes. Moreover, S-carvone hindered isoprenylation of a prenylable GFP indicator protein expressed in N. tabacum cell lines, which can be chemically complemented with geranylgeraniol. The model was further validated using N. tabacum cell extracts or recombinant N. tabacum protein prenyltransferases expressed in Escherichia coli. Our study endorsed a reevaluation of the effect of S-carvone on plant isoprenoid metabolism. PMID:24367019

Antimetastatic potential of vernolide-A, a sesquiterpenoid from Vernonia cinerea L.

PubMed

Pratheeshkumar, P; Kuttan, Girija

2012-01-01

The inhibitory effect of vernolide-A (C(21)H(28)O(7)) on lung metastasis induced by B16F-10 melanoma cells was studied using C57BL/6 mice. Vernolide-A was administered in three different modalities such as simultaneously with tumor, prophylactic to tumor and after tumor development. Maximum inhibition in the metastasis was observed when vernolide-A was administered simultaneously with tumor. There was 89.39% inhibition of lung tumor nodule formation and 88.51% increase in the life span of metastatic tumor-bearing animals. Highly elevated levels of lung hydroxyproline, lung uronic acid, lung hexosamine, serum sialic acid, serum γ-glutamyl transpeptidase (GGT) and serum vascular endothelial growth factor (VEGF) in the metastatic control animals were found to be significantly lowered in the vernolide-A-treated animals. Histopathological analysis of lung tissues also correlated with these results. Vernolide-A administration downregulated the expression of matrix metalloproteinase-2 (MMP-2), MMP-9, extracellular-signal-regulated kinase-1 (ERK-1), ERK-2 and VEGF in the lung tissue of B16F-10 melanoma challenged animals. In the in vitro system, vernolide-A showed a significant inhibition of invasion of B16F-10 melanoma cells across the collagen matrix. Vernolide-A treatment also inhibited the migration of B16F-10 melanoma cells across a polycarbonate filter in vitro. Vernolide-A could inhibit MMP-2 and MMP-9 protein expression in gelatin zymographic analysis of B16F-10 cells. (3)H-thymidine proliferation assay showed that vernolide-A could inhibit the proliferation of B16F-10 melanoma cells in vitro. These results indicate that vernolide-A could inhibit the metastatic progression of B16F-10 melanoma cells in mice.

Metabolic engineering of geranic acid in maize to achieve fungal resistance is compromised by novel glycosylation patterns.

PubMed

Yang, Ting; Stoopen, Geert; Yalpani, Nasser; Vervoort, Jacques; de Vos, Ric; Voster, Alessandra; Verstappen, Francel W A; Bouwmeester, Harro J; Jongsma, Maarten A

2011-07-01

Many terpenoids are known to have antifungal properties and overexpression of these compounds in crops is a potential tool in disease control. In this study, 15 different mono- and sesquiterpenoids were tested in vitro against two major pathogenic fungi of maize (Zea mays), Colletotrichum graminicola and Fusarium graminearum. Among all tested terpenoids, geranic acid showed very strong inhibitory activity against both fungi (MIC<46 μM). To evaluate the possibility of enhancing fungal resistance in maize by overexpressing geranic acid, we generated transgenic plants with the geraniol synthase gene cloned from Lippia dulcis under the control of a ubiquitin promoter. The volatile and non-volatile metabolite profiles of leaves from transgenic and control lines were compared. The headspaces collected from intact seedlings of transgenic and control plants were not significantly different, although detached leaves of transgenic plants emitted 5-fold more geranyl acetate compared to control plants. Non-targeted LC-MS profiling and LC-MS-MS identification of extracts from maize leaves revealed that the major significantly different non-volatile compounds were 2 geranic acid derivatives, a geraniol dihexose and 4 different types of hydroxyl-geranic acid-hexoses. A geranic acid glycoside was the most abundant, and identified by NMR as geranoyl-6-O-malonyl-β-d-glucopyranoside with an average concentration of 45μM. Fungal bioassays with C. graminicola and F. graminearum did not reveal an effect of these changes in secondary metabolite composition on plant resistance to either fungus. The results demonstrate that metabolic engineering of geraniol into geranic acid can rely on the existing default pathway, but branching glycosylation pathways must be controlled to achieve accumulation of the aglycones. Copyright © 2011 Elsevier Inc. All rights reserved.

Speciated measurements of semivolatile and intermediate volatility organic compounds (S/IVOCs) in a pine forest during BEACHON-RoMBAS 2011

DOE PAGES

Chan, A. W. H.; Kreisberg, N. M.; Hohaus, T.; ...

2016-02-02

Understanding organic composition of gases and particles is essential to identifying sources and atmospheric processing leading to organic aerosols (OA), but atmospheric chemical complexity and the analytical techniques available often limit such analysis. Here we present speciated measurements of semivolatile and intermediate volatility organic compounds (S/IVOCs) using a novel dual-use instrument (SV-TAG-AMS) deployed at Manitou Forest, CO, during the Bio-hydro-atmosphere interactions of Energy, Aerosols, Carbon, H 2O, Organics & Nitrogen – Rocky Mountain Biogenic Aerosol Study (BEACHON-RoMBAS) 2011 campaign. This instrument provides on-line speciation of ambient organic compounds with 2 h time resolution. The species in this volatility range aremore » complex in composition, but their chemical identities reveal potential sources. Observed compounds of biogenic origin include sesquiterpenes with molecular formula C 15H 24 (e.g., β-caryophyllene and longifolene), which were most abundant at night. A variety of other biogenic compounds were observed, including sesquiterpenoids with molecular formula C 15H 22, abietatriene and other terpenoid compounds. Many of these compounds have been identified in essential oils and branch enclosure studies but were observed in ambient air for the first time in our study. Semivolatile polycyclic aromatic hydrocarbons (PAHs) and alkanes were observed with highest concentrations during the day and the dependence on temperature suggests the role of an evaporative source. Using statistical analysis by positive matrix factorization (PMF), we classify observed S/IVOCs by their likely sources and processes, and characterize them based on chemical composition. The total mass concentration of elutable S/IVOCs was estimated to be on the order of 0.7 µg m –3 and their volatility distributions are estimated for modeling aerosol formation chemistry.« less

Gene expression and metabolism preceding soft scald, a chilling injury of 'Honeycrisp' apple fruit.

PubMed

Leisso, Rachel S; Gapper, Nigel E; Mattheis, James P; Sullivan, Nathanael L; Watkins, Christopher B; Giovannoni, James J; Schaffer, Robert J; Johnston, Jason W; Hanrahan, Ines; Hertog, Maarten L A T M; Nicolaï, Bart M; Rudell, David R

2016-10-12

'Honeycrisp' is an apple cultivar that is susceptible to soft scald, a chilling injury expressed as necrotic patches on the peel. Improved understanding of metabolism associated with the disorder would improve our understanding of soft scald and contribute to developing more effective management strategies for apple storage. It was expected that specific gene expression and specific metabolite levels in the peel would be linked with soft scald risk at harvest and/or specific time points during cold storage. Fruit from nine 'Honeycrisp' apple orchards that would eventually develop different incidences of soft scald between 4 and 8 weeks of cold air storage were used to contrast and determine differential transcriptomic and metabolomic changes during storage. Untargeted metabolic profiling revealed changes in a number of distinct pathways preceding and concurrent with soft scald symptom development, including elevated γ-aminobutryic acid (GABA), 1-hexanol, acylated steryl glycosides, and free p-coumaryl acyl esters. At harvest, levels of sesquiterpenoid and triterpenoid acyl esters were relatively higher in peel of fruit that did not later develop the disorder. RNA-seq driven gene expression profiling highlighted possible involvement of genes and associated metabolic processes with soft scald development. These included elevated expression of genes involved in lipid peroxidation and phenolic metabolism in fruit with soft scald, and isoprenoid/brassinosteroid metabolism in fruit that did not develop soft scald. Expression of other stress-related genes in fruit that developed soft scald included chlorophyll catabolism, cell wall loosening, and lipid transport while superoxide dismutases were up-regulated in fruit that did not develop the disorder. This study delineates the sequential transcriptomic and metabolomic changes preceding soft scald symptom development. Changes were differential depending on susceptibility of fruit to the disorder and could be attributed to key stress related and mediating pathways.

Characterizing the binding interaction between antimalarial artemether (AMT) and bovine serum albumin (BSA): Spectroscopic and molecular docking methods.

PubMed

Shi, Jie-Hua; Pan, Dong-Qi; Wang, Xiou-Xiou; Liu, Ting-Ting; Jiang, Min; Wang, Qi

2016-09-01

Artemether (AMT), a peroxide sesquiterpenoides, has been widely used as an antimalarial for the treatment of multiple drug-resistant strains of plasmodium falciparum malaria. In this work, the binding interaction of AMT with bovine serum albumin (BSA) under the imitated physiological conditions (pH7.4) was investigated by UV spectroscopy, fluorescence emission spectroscopy, synchronous fluorescence spectroscopy, Fourier transform infrared spectroscopy (FT-IR), circular dichroism (CD), three-dimensional fluorescence spectroscopy and molecular docking methods. The experimental results indicated that there was a change in UV absorption of BSA along with a slight red shift of absorption wavelength, indicating that the interaction of AMT with BSA occurred. The intrinsic fluorescence of BSA was quenched by AMT due to the formation of AMT-BSA complex. The number of binding sites (n) and binding constant of AMT-BSA complex were about 1 and 2.63×10(3)M(-1) at 298K, respectively, suggesting that there was stronger binding interaction of AMT with BSA. Based on the analysis of the signs and magnitudes of the free energy change (ΔG(0)), enthalpic change (ΔH(0)) and entropic change (ΔS(0)) in the binding process, it can be concluded that the binding of AMT with BSA was enthalpy-driven process due to |ΔH°|>|TΔS°|. The results of experiment and molecular docking confirmed the main interaction forces between AMT and BSA were van der Waals force. And, there was a slight change in the BSA conformation after binding AMT but BSA still retains its secondary structure α-helicity. However, it had been confirmed that AMT binds on the interface between sub-domain IIA and IIB of BSA. Copyright © 2016 Elsevier B.V. All rights reserved.

Molecular Determinants of Juvenile Hormone Action as Revealed by 3D QSAR Analysis in Drosophila

PubMed Central

Beňo, Milan; Farkaš, Robert

2009-01-01

Background Postembryonic development, including metamorphosis, of many animals is under control of hormones. In Drosophila and other insects these developmental transitions are regulated by the coordinate action of two principal hormones, the steroid ecdysone and the sesquiterpenoid juvenile hormone (JH). While the mode of ecdysone action is relatively well understood, the molecular mode of JH action remains elusive. Methodology/Principal Findings To gain more insights into the molecular mechanism of JH action, we have tested the biological activity of 86 structurally diverse JH agonists in Drosophila melanogaster. The results were evaluated using 3D QSAR analyses involving CoMFA and CoMSIA procedures. Using this approach we have generated both computer-aided and species-specific pharmacophore fingerprints of JH and its agonists, which revealed that the most active compounds must possess an electronegative atom (oxygen or nitrogen) at both ends of the molecule. When either of these electronegative atoms are replaced by carbon or the distance between them is shorter than 11.5 Å or longer than 13.5 Å, their biological activity is dramatically decreased. The presence of an electron-deficient moiety in the middle of the JH agonist is also essential for high activity. Conclusions/Significance The information from 3D QSAR provides guidelines and mechanistic scope for identification of steric and electrostatic properties as well as donor and acceptor hydrogen-bonding that are important features of the ligand-binding cavity of a JH target protein. In order to refine the pharmacophore analysis and evaluate the outcomes of the CoMFA and CoMSIA study we used pseudoreceptor modeling software PrGen to generate a putative binding site surrogate that is composed of eight amino acid residues corresponding to the defined molecular interactions. PMID:19547707

Ecological Roles and Biological Activities of Specialized Metabolites from the Genus Nicotiana.

PubMed

Jassbi, Amir Reza; Zare, Somayeh; Asadollahi, Mojtaba; Schuman, Meredith C

2017-10-11

Species of Nicotiana grow naturally in different parts of the world and have long been used both medicinally and recreationally by human societies. More recently in our history, Nicotiana tabacum has attracted interest as one of the most economically important industrial crops. Nicotiana species are frequently investigated for their bioactive natural products, and the ecological role of their specialized metabolites in responses to abiotic stress or biotic stress factors like pathogens and herbivores. The interest of tobacco companies in genetic information as well as the success of a few wild tobacco species as experimental model organisms have resulted in growing knowledge about the molecular biology and ecology of these plants and functional studies of the plant's natural products. Although a large number of reviews and books on biologically active natural products already exists, mostly from N. tabacum, we focus our attention on the ecological roles and biological activity of natural products, versus products from cured and processed material, in this Review. The studied compounds include alkaloids, aromatic compounds, flavonoids, volatiles, sesquiterpenoids, diterpenes alcohols, and sugar esters from trichomes of the plants, and recently characterized acyclic hydroxygeranyllinalool diterpene glycosides (HGL-DTGs). In this Review (1800s-2017), we describe the above-mentioned classes of natural products, emphasizing their biological activities and functions as they have been determined either in bioassay-guided purification approaches or in bioassays with plants in which the expression of specific biosynthetic genes has been genetically manipulated. Additionally, a review on the history, taxonomy, ecology, and medicinal application of different Nicotiana species growing around the globe presented in this Review may be of interest for pharmacognosists, natural products, and ecological chemists.

Optimisation of solid-phase microextraction combined with gas chromatography-mass spectrometry based methodology to establish the global volatile signature in pulp and skin of Vitis vinifera L. grape varieties.

PubMed

Perestrelo, Rosa; Barros, António S; Rocha, Sílvia M; Câmara, José S

2011-09-15

The volatiles (VOCs) and semi-volatile organic compounds (SVOCs) responsible for aroma are mainly present in skin of grape varieties. Thus, the present investigation is directed towards the optimisation of a solvent free methodology based on headspace-solid-phase microextraction (HS-SPME) combined with gas chromatography-quadrupole mass spectrometry (GC-qMS) in order to establish the global volatile composition in pulp and skin of Bual and Bastardo Vitis vinifera L. varieties. A deep study on the extraction-influencing parameters was performed, and the best results, expressed as GC peak area, number of identified compounds and reproducibility, were obtained using 4 g of sample homogenised in 5 mL of ultra-pure Milli-Q water in a 20 mL glass vial with addition of 2g of sodium chloride (NaCl). A divinylbenzene/carboxen/polydimethylsiloxane fibre was selected for extraction at 60°C for 45 min under continuous stirring at 800 rpm. More than 100 VOCs and SVOCs, including 27 monoterpenoids, 27 sesquiterpenoids, 21 carbonyl compounds, 17 alcohols (from which 2 aromatics), 10 C(13) norisoprenoids and 5 acids were identified. The results showed that, for both grape varieties, the levels and number of volatiles in skin were considerably higher than those observed in pulp. According to the data obtained by principal component analysis (PCA), the establishment of the global volatile signature of grape and the relationship between different part of grapes-pulp and skin, may be an useful tool to winemaker decision to define the vinification procedures that improves the organoleptic characteristics of the corresponding wines and consequently contributed to an economic valorization and consumer acceptance. Copyright © 2011 Elsevier B.V. All rights reserved.

Isolation and characterisation of 13 pterosins and pterosides from bracken (Pteridium aquilinum (L.) Kuhn) rhizome.

PubMed

Mohammad, Rizgar Hassan; Nur-E-Alam, Mohammad; Lahmann, Martina; Parveen, Ifat; Tizzard, Graham J; Coles, Simon J; Fowler, Mark; Drake, Alex F; Heyes, Derren; Thoss, Vera

2016-08-01

Systematic phytochemical investigations of the underground rhizome of Pteridium aquilinum (L.) Kuhn (Dennstaedtiaceae) afforded thirty-five pterosins and pterosides. By detailed analysis of one- and two-dimensional nuclear magnetic resonance spectroscopy, circular dichroism (CD) and high-resolution mass spectrometric data, thirteen previously undescribed pterosins and pterosides have been identified. Interestingly, for the first time 12-O-β-D-glucopyranoside substituted pterosins, rhedynosides C and D, and the sulfate-containing pterosin, rhedynosin H, alongside the two known compounds, histiopterosin A and (2S)-pteroside A2, were isolated from the rhizomes of subsp. aquilinum of bracken. In addition, six-membered cyclic ether pterosins and pterosides, rhedynosin A and rhedynoside A, are the first examples of this type of pterosin-sesquiterpenoid. Additionally, the three previously reported compounds (rhedynosin I, (2S)-2-hydroxymethylpterosin E and (2S)-12-hydroxypterosin A) were obtained for the first time from plants as opposed to mammalian metabolic products. Single crystal X-ray diffraction analysis was applied to the previously undescribed compounds (2R)-rhedynoside B, (2R)-pteroside B and (2S)-pteroside K, yielding the first crystal structures for pterosides, and three known pterosins, (2S)-pterosin A, trans-pterosin C and cis-pterosin C. Rhedynosin C is the only example of the cyclic lactone pterosins with a keto group at position C-14. Six selected pterosins ((2S)-pterosin A, (2R)-pterosin B and trans-pterosin C) and associated glycosides ((2S)-pteroside A, (2R)-pteroside B and pteroside Z) were assessed for their anti-diabetic activity using an intestinal glucose uptake assay; all were found to be inactive at 300 μM. Copyright © 2016 Elsevier Ltd. All rights reserved.

Ectopic Terpene Synthase Expression Enhances Sesquiterpene Emission in Nicotiana attenuata without Altering Defense or Development of Transgenic Plants or Neighbors1[W

PubMed Central

Schuman, Meredith C.; Palmer-Young, Evan C.; Schmidt, Axel; Gershenzon, Jonathan; Baldwin, Ian T.

2014-01-01

Sesquiterpenoids, with approximately 5,000 structures, are the most diverse class of plant volatiles with manifold hypothesized functions in defense, stress tolerance, and signaling between and within plants. These hypotheses have often been tested by transforming plants with sesquiterpene synthases expressed behind the constitutively active 35S promoter, which may have physiological costs measured as inhibited growth and reduced reproduction or may require augmentation of substrate pools to achieve enhanced emission, complicating the interpretation of data from affected transgenic lines. Here, we expressed maize (Zea mays) terpene synthase10 (ZmTPS10), which produces (E)-α-bergamotene and (E)-β-farnesene, or a point mutant ZmTPS10M, which produces primarily (E)-β-farnesene, under control of the 35S promoter in the ecological model plant Nicotiana attenuata. Transgenic N. attenuata plants had specifically enhanced emission of target sesquiterpene(s) with no changes detected in their emission of any other volatiles. Treatment with herbivore or jasmonate elicitors induces emission of (E)-α-bergamotene in wild-type plants and also tended to increase emission of (E)-α-bergamotene and (E)-β-farnesene in transgenics. However, transgenics did not differ from the wild type in defense signaling or chemistry and did not alter defense chemistry in neighboring wild-type plants. These data are inconsistent with within-plant and between-plant signaling functions of (E)-β-farnesene and (E)-α-bergamotene in N. attenuata. Ectopic sesquiterpene emission was apparently not costly for transgenics, which were similar to wild-type plants in their growth and reproduction, even when forced to compete for common resources. These transgenics would be well suited for field experiments to investigate indirect ecological effects of sesquiterpenes for a wild plant in its native habitat. PMID:25187528

Features of citrus terpenoid production as revealed by carotenoid, limonoid and aroma profiles of two pummelos (Citrus maxima) with different flesh color.

PubMed

Liu, Cuihua; Yan, Fuhua; Gao, Huijun; He, Min; Wang, Zhuang; Cheng, Yunjiang; Deng, Xiuxin; Xu, Juan

2015-01-01

Terpenoids are major components of carotenoids, limonoids and aromas in citrus fruits, resulting in fruit coloration, bitterness and aroma. In this study the carotenoid, limonoid and volatile profiles of red-flesh Chuhong pummelo (CH) and pale green-flesh Feicui pummelo (FC) were investigated by HPLC and GC/MS. Large differences were found in constituents of carotenoids and limonoids in juice sacs and flavedo and of aromas in flavedo of the two pummelos. For carotenoids in juice sacs, CH contained 57 times the amount in FC, mainly all-trans-lycopene and phytoene, whereas in flavedo it contained only 25% of that in FC, the latter showing a high proportion of β-carotene and other chloroplastic carotenoids. In comparison with FC, limonin and nomilin aglycone production was boosted in juice sacs of CH while being almost absent in flavedo. For volatiles in flavedo, the total amount was significantly higher in CH. PCA suggested that germacrene-type sesquiterpenoids, etc. were principal in distinguishing volatile profiles of the two pummelos. The data showed a different tissue-biased pattern of carotenoid and limonoid aglycone synthesis in pummelos with different flesh color, and the possible independently regulated synthesis of those metabolites in different fruit tissues. Furthermore, decreased carotenoid and limonoid aglycone production accompanied by increased accumulation of volatile terpenoids in flavedo of red-flesh CH was identified, indicating that a total capacity or a balance of production of various terpenoids might exist in pummelo fruit tissues. It was also suggested that substrate concentration is not the key factor affecting product concentrations during the synthesis of monoterpene derivatives. © 2014 Society of Chemical Industry.

A genetically-based latitudinal cline in the emission of herbivore-induced plant volatile organic compounds.

PubMed

Wason, Elizabeth L; Agrawal, Anurag A; Hunter, Mark D

2013-08-01

The existence of predictable latitudinal variation in plant defense against herbivores remains controversial. A prevailing view holds that higher levels of plant defense evolve at low latitudes compared to high latitudes as an adaptive plant response to higher herbivore pressure on low-latitude plants. To date, this prediction has not been examined with respect to volatile organic compounds (VOCs) that many plants emit, often thus attracting the natural enemies of herbivores. Here, we compared genetically-based constitutive and herbivore-induced aboveground vegetative VOC emissions from plants originating across a gradient of more than 10° of latitude (>1,500 km). We collected headspace VOCs from Asclepias syriaca (common milkweed) originating from 20 populations across its natural range and grown in a common garden near the range center. Feeding by specialist Danaus plexippus (monarch) larvae induced VOCs, and field environmental conditions (temperature, light, and humidity) also influenced emissions. Monarch damage increased plant VOC concentrations and altered VOC blends. We found that genetically-based induced VOC emissions varied with the latitude of plant population origin, although the pattern followed the reverse of that predicted-induced VOC concentration increased with increasing latitude. This pattern appeared to be driven by a greater induction of sesquiterpenoids at higher latitudes. In contrast, constitutive VOC emission did not vary systematically with latitude, and the induction of green leafy volatiles declined with latitude. Our results do not support the prevailing view that plant defense is greater at lower than at higher latitudes. That the pattern holds only for herbivore-induced VOC emission, and not constitutive emission, suggests that latitudinal variation in VOCs is not a simple adaptive response to climatic factors.

Speciated measurements of semivolatile and intermediate volatility organic compounds (S/IVOCs) in a pine forest during BEACHON-RoMBAS 2011

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

Chan, A. W. H.; Kreisberg, N. M.; Hohaus, T.

Understanding organic composition of gases and particles is essential to identifying sources and atmospheric processing leading to organic aerosols (OA), but atmospheric chemical complexity and the analytical techniques available often limit such analysis. Here we present speciated measurements of semivolatile and intermediate volatility organic compounds (S/IVOCs) using a novel dual-use instrument (SV-TAG-AMS) deployed at Manitou Forest, CO, during the Bio-hydro-atmosphere interactions of Energy, Aerosols, Carbon, H 2O, Organics & Nitrogen – Rocky Mountain Biogenic Aerosol Study (BEACHON-RoMBAS) 2011 campaign. This instrument provides on-line speciation of ambient organic compounds with 2 h time resolution. The species in this volatility range aremore » complex in composition, but their chemical identities reveal potential sources. Observed compounds of biogenic origin include sesquiterpenes with molecular formula C 15H 24 (e.g., β-caryophyllene and longifolene), which were most abundant at night. A variety of other biogenic compounds were observed, including sesquiterpenoids with molecular formula C 15H 22, abietatriene and other terpenoid compounds. Many of these compounds have been identified in essential oils and branch enclosure studies but were observed in ambient air for the first time in our study. Semivolatile polycyclic aromatic hydrocarbons (PAHs) and alkanes were observed with highest concentrations during the day and the dependence on temperature suggests the role of an evaporative source. Using statistical analysis by positive matrix factorization (PMF), we classify observed S/IVOCs by their likely sources and processes, and characterize them based on chemical composition. The total mass concentration of elutable S/IVOCs was estimated to be on the order of 0.7 µg m –3 and their volatility distributions are estimated for modeling aerosol formation chemistry.« less

Hormonal regulation of Drosophila microRNA let-7 and miR-125 that target innate immunity.

PubMed

Garbuzov, Alina; Tatar, Marc

2010-01-01

The steroid 20-hydroxy-ecdysone (20-HE) and the sesquiterpenoid Juvenile Hormone (JH) coordinate insect life stage transitions. 20-HE exerts these effects by the sequential induction of response genes. In the nematode Caenorhabditis elegans hormones also play a role in such transitions, but notably, microRNA such as let-7 and lin-4 have likewise been found to help order developmental steps. Little is known about the corresponding function of homologous microRNA in Drosophila melanogaster, and the way microRNA might be regulated by 20-HE in the fly is ambiguous. Here we used Drosophila S2 cells to analyze the effects of 20-HE on D. melanogaster microRNA let-7 and miR-125, the homolog of lin-4. The induction by 20-HE of let-7 and miR-125 in S2 cells is inhibited by RNAi knockdown of the ecdysone receptor and, as previously shown, by knockdown of its cofactor broad-complex C. To help resolve the currently ambiguous role of 20-HE in the control of microRNA, we show that nanomolar concentrations of 20-HE primes cells to subsequently express microRNA when exposed to micromolar levels of 20-HE. We then explore the role microRNA plays in the established relationship between 20-HE and the induction of innate immunity. We show that the 3'UTR of the antimicrobial peptide diptericin has a let-7 binding site and that let-7 represses translation from this site. We conclude that 20-HE facilitates the initial expression of innate immunity while it simultaneously induces negative regulation via microRNA control of antimicrobial peptide translation.

Phylogenetic fragrance patterns in Nicotiana sections Alatae and Suaveolentes.

PubMed

Raguso, Robert A; Schlumpberger, Boris O; Kaczorowski, Rainee L; Holtsford, Timothy P

2006-09-01

We analyzed floral volatiles from eight tobacco species (Nicotiana; Solanaceae) including newly discovered Brazilian taxa (Nicotiana mutabilis and "Rastroensis") in section Alatae. Eighty-four compounds were found, including mono- and sesquiterpenoids, nitrogenous compounds, benzenoid and aliphatic alcohols, aldehydes and esters. Floral scent from recent accessions of Nicotiana alata, Nicotiana bonariensis and Nicotiana langsdorffii differed from previously published data, suggesting intraspecific variation in scent composition at the level of biosynthetic class. Newly discovered taxa in Alatae, like their relatives, emit large amounts of 1,8-cineole and smaller amounts of monoterpenes on a nocturnal rhythm, constituting a chemical synapomorphy for this lineage. Fragrance data from three species of Nicotiana sect. Suaveolentes, the sister group of Alatae, (two Australian species: N. cavicola, N. ingulba; one African species: N. africana), were compared to previously reported data from their close relative, N. suaveolens. Like N. suaveolens, N. cavicola and N. ingulba emit fragrances dominated by benzenoids and phenylpropanoids, whereas the flowers of N. africana lacked a distinct floral scent and instead emitted only small amounts of an aliphatic methyl ester from foliage. Interestingly, this ester also is emitted from foliage of N. longiflora and N. plumbaginifolia (both in section Alatae s.l.), which share a common ancestor with N. africana. This result, combined with the synapomorphic pattern of 1,8 cineole emission in Alatae s.s., suggests that phylogenetic signal explains a major component of fragrance composition among tobacco species in sections Alatae and Suaveolentes. At the intraspecific level, interpopulational scent variation is widespread in sect. Alatae, and may reflect edaphic specialization, introgression, local pollinator shifts, genetic drift or artificial selection in cultivation. Further studies with genetically and geographically well-defined populations are needed to distinguish between these possibilities.

Tyrosinase inhibitory activity, molecular docking studies and antioxidant potential of chemotypes of Lippia origanoides (Verbenaceae) essential oils.

PubMed

da Silva, Alessandra P; Silva, Natália de F; Andrade, Eloísa Helena A; Gratieri, Tais; Setzer, William N; Maia, José Guilherme S; da Silva, Joyce Kelly R

2017-01-01

The essential oils (EOs) of the aerial parts of Lippia origanoides (LiOr), collected in different localities of the Amazon region, were obtained by hydrodistillation and analyzed by GC and CG-MS. Principle component analysis (PCA) based on chemical composition grouped the oils in four chemotypes rich in mono- and sesquiterpenoids. Group I was characterized by 1,8-cineole and α-terpineol (LiOr-1 and LiOr-4) and group II by thymol (LiOr-2). The oil LiOr-3 showed β-caryophyllene, α-phellandrene and β-phellandrene as predominant and LiOr-5 was rich in (E)-nerolidol and β-caryophyllene. All samples were evaluated for antioxidant activity and inhibition of tyrosinase in vitro and in silico. The highest antioxidant activity by the DPPH free radical method was observed in LiOr-2 and LiOr-5 oils (132.1 and 82.7 mg TE∙mL-1, respectively). The tyrosinase inhibition potential was performed using L-tyrosine and L-DOPA as substrates and all samples were more effective in the first step of oxidation. The inhibition by samples LiOr-2 and LiOr-4 were 84.7% and 62.6%, respectively. The samples LiOr-1, LiOr-4 and LiOr-5 displayed an interaction with copper (II) ion with bathochromic shift around 15 nm. In order to elucidate the mechanism of inhibition of the main compounds, a molecular docking study was carried out. All compounds displayed an interaction between an oxygen and Cu or histidine residues with distances less than 4 Å. The best docking energies were observed with thymol and (E)-nerolidol (-79.8 kcal.mol-1), which suggested H-bonding interactions with Met281 and His263 (thymol) and His259, His263 ((E)-nerolidol).

A basic leucine zipper transcription factor, AabZIP1, connects abscisic acid signaling with artemisinin biosynthesis in Artemisia annua.

PubMed

Zhang, Fangyuan; Fu, Xueqing; Lv, Zongyou; Lu, Xu; Shen, Qian; Zhang, Ling; Zhu, Mengmeng; Wang, Guofeng; Sun, Xiaofen; Liao, Zhihua; Tang, Kexuan

2015-01-01

Artemisinin is a sesquiterpenoid especially synthesized in the Chinese herbal plant, Artemisia annua, which is widely used in the treatment of malaria. Artemisinin accumulation can be enhanced by exogenous abscisic acid (ABA) treatment. However, it is not known how ABA signaling regulates artemisinin biosynthesis. A global expression profile and phylogenetic analysis as well as the dual-LUC screening revealed that a basic leucine zipper family transcription factor from A. annua (namely AabZIP1) was involved in ABA signaling to regulate artemisinin biosynthesis. AabZIP1 had a higher expression level in the inflorescences than in other tissues; ABA treatment, drought, and salt stress strongly induced the expression of AabZIP1. Yeast one-hybrid assay and electrophoretic mobility shift assay (EMSA) showed that AabZIP1 bound to the ABA-responsive elements (ABRE) in the promoter regions of the amorpha-4,11-diene synthase (ADS) gene and CYP71AV1, which are two key structural genes of the artemisinin biosynthetic pathway. A mutagenesis assay showed that the C1 domain in the N-terminus of AabZIP1 was important for its transactivation activity. Furthermore, the activation of ADS and CYP71AV1 promoters by AabZIP1 was enhanced by ABA treatment in transient dual-LUC analysis. The AabZIP1 variant with C1 domain deletion lost the ability to activate ADS and CYP71AV1 promoters regardless of ABA treatment. Notably, overexpression of AabZIP1 in A. annua resulted in significantly increased accumulation of artemisinin. Our results indicate that ABA promotes artemisinin biosynthesis, likely through 1 activation of ADS and CYP71AV1 expression by AabZIP in A. annua. Meanwhile, our findings reveal the potential value of AabZIP1 in genetic engineering of artemisinin production. Copyright © 2015 The Author. Published by Elsevier Inc. All rights reserved.

Genetic Transformation of Artemisia carvifolia Buch with rol Genes Enhances Artemisinin Accumulation.

PubMed

Dilshad, Erum; Cusido, Rosa Maria; Ramirez Estrada, Karla; Bonfill, Mercedes; Mirza, Bushra

2015-01-01

The potent antimalarial drug artemisinin has a high cost, since its only viable source to date is Artemisia annua (0.01-0.8% DW). There is therefore an urgent need to design new strategies to increase its production or to find alternative sources. In the current study, Artemisia carvifolia Buch was selected with the aim of detecting artemisinin and then enhancing the production of the target compound and its derivatives. These metabolites were determined by LC-MS in the shoots of A. carvifolia wild type plants at the following concentrations: artemisinin (8μg/g), artesunate (2.24μg/g), dihydroartemisinin (13.6μg/g) and artemether (12.8μg/g). Genetic transformation of A. carvifolia was carried out with Agrobacterium tumefaciens GV3101 harboring the rol B and rol C genes. Artemisinin content increased 3-7-fold in transgenics bearing the rol B gene, and 2.3-6-fold in those with the rol C gene. A similar pattern was observed for artemisinin analogues. The dynamics of artemisinin content in transgenics and wild type A.carvifolia was also correlated with the expression of genes involved in its biosynthesis. Real time qPCR analysis revealed the differential expression of genes involved in artemisinin biosynthesis, i.e. those encoding amorpha-4, 11 diene synthase (ADS), cytochrome P450 (CYP71AV1), and aldehyde dehydrogenase 1 (ALDH1), with a relatively higher transcript level found in transgenics than in the wild type plant. Also, the gene related to trichome development and sesquiterpenoid biosynthesis (TFAR1) showed an altered expression in the transgenics compared to wild type A.carvifolia, which was in accordance with the trichome density of the respective plants. The trichome index was significantly higher in the rol B and rol C gene-expressing transgenics with an increased production of artemisinin, thereby demonstrating that the rol genes are effective inducers of plant secondary metabolism.

Jasmonate-Mediated Induced Volatiles in the American Cranberry, Vaccinium macrocarpon: From Gene Expression to Organismal Interactions

PubMed Central

Rodriguez-Saona, Cesar R.; Polashock, James; Malo, Edi A.

2013-01-01

Jasmonates, i.e., jasmonic acid (JA) and methyl jasmonate (MeJA), are signaling hormones that regulate a large number of defense responses in plants which in turn affect the plants’ interactions with herbivores and their natural enemies. Here, we investigated the effect of jasmonates on the emission of volatiles in the American cranberry, Vaccinium macrocarpon, at different levels of biological organization from gene expression to organismal interactions. At the molecular level, four genes (BCS, LLS, NER1, and TPS21) responded significantly to gypsy moth larval feeding, MeJA, and mechanical wounding, but to different degrees. The most dramatic changes in expression of BCS and TPS21 (genes in the sesquiterpenoid pathway) were when treated with MeJA. Gypsy moth-damaged and MeJA-treated plants also had significantly elevated expression of LLS and NER1 (genes in the monoterpene and homoterpene biosynthesis pathways, respectively). At the biochemical level, MeJA induced a complex blend of monoterpene and sesquiterpene compounds that differed from gypsy moth and mechanical damage, and followed a diurnal pattern of emission. At the organismal level, numbers of Sparganothis sulfureana moths were lower while numbers of parasitic wasps were higher on sticky traps near MeJA-treated cranberry plants than those near untreated plants. Out of 11 leaf volatiles tested, (Z)-3-hexenyl acetate, linalool, and linalool oxide elicited strong antennal (EAG) responses from S. sulfureana, whereas sesquiterpenes elicited weak EAG responses. In addition, mortality of S. sulfureana larvae increased by about 43% in JA treated cranberry plants as compared with untreated plants, indicating a relationship among adult preference, antennal sensitivity to plant odors, and offspring performance. This study highlights the role of the jasmonate-dependent defensive pathway in the emissions of herbivore-induced volatiles in cranberries and its importance in multi-trophic level interactions. PMID:23641249

Toxicity of basil oil constituents and related compounds and the efficacy of spray formulations to Dermatophagoides farinae (Acari: Pyroglyphidae).

PubMed

Perumalsamy, Haribalan; Kim, Jae Yeon; Kim, Jun-Ran; Hwang, Kum Na Ra; Ahn, Young-Joon

2014-05-01

Pyroglyphid house dust mites are the most common cause of allergic symptoms in humans. An assessment was made of the toxicity of basil, Ocimum basilicum L, essential oil, 11 basil oil constituents, seven structurally related compounds, and another 22 previously known basil oil constituents to adult American house dust mites, Dermatophagoides farinae Hughes. The efficacy of four experimental spray formulations containing basil oil (1, 2, 3, and 4% sprays) was also assessed. Results were compared with those of two conventional acaricides benzyl benzoate and N,N-diethyl-3-methylbenzamide. The active principles of basil oil were determined to be citral, alpha-terpineol, and linalool. Citral (24 h LC50, 1.13 microg/cm2) and menthol (1.69 microg/cm2) were the most toxic compounds, followed by methyl eugenol (5.78 microg/cm2). These compounds exhibited toxicity greater than benzyl benzoate (LC50, 8.41 microg/cm2) and N,N-diethyl-3-methylbenzamide (37.67 microg/cm2). Potent toxicity was also observed with eugenol, menthone, spathulenol, alpha-terpineol, nerolidol, zerumbone, and nerol (LC50, 12.52-21.44 microg/cm2). Interestingly, the sesquiterpenoid alpha-humulene, lacking only the carbonyl group present in zerumbone, was significantly less effective than zerumbone, indicating that the alpha,beta-unsaturated carbonyl group of zerumbone is a prerequisite component for toxicity. These compounds were consistently more toxic in closed versus open containers, indicating that their mode of delivery was largely a result of vapor action. Basil oil applied as 3 and 4% sprays provided 97 and 100% mortality against the mites, respectively, whereas permethrin (cis:trans, 25:75) 2.5 g/liter spray treatment resulted in 17% mortality. Our results indicate that practical dust mite control in indoor environments can be achieved by basil oil spray formulations (3 and 4% sprays) as potential contact-action fumigants.

In silico analysis sheds light on the structural basis underlying the ribotoxicity of trichothecenes-A tool for supporting the hazard identification process.

PubMed

Dellafiora, Luca; Galaverna, Gianni; Dall'Asta, Chiara

2017-03-15

Deoxynivalenol is a food borne mycotoxin belonging to the trichothecenes family that may cause severe injuries in human and animals. The inhibition of protein synthesis via the interaction with the ribosome has been identified as a crucial mechanism underlying toxic action. However, it is not still fully understood how and to what extent compounds belonging to trichothecenes family affect human and animal health. In turn, this scenario causes delay in managing the related health risk. Aimed at supporting the hazard identification process, the in silico analysis may be a straightforward tool to investigate the structure-activity relationship of trichothecenes, finding out molecules of possible concern to carry forth in the risk assessment process. In this framework, this work investigated through a molecular modeling approach the structural basis underlying the interaction with the ribosome under a structure-activity relationship perspective. To identify further forms possibly involved in the total trichothecenes-dependent ribotoxic load, the model was challenged with a set of 16 trichothecene modified forms found in plants, fungi and animals, including also compounds never tested before for the capability to bind and inhibit the ribosome. Among them, only the regiospecific glycosylation in the position 3 of the sesquiterpenoid scaffold (i.e. T-2 toxin-3-glucuronide, α and β isomers of T-2 toxin-3-glucoside and deoxynivalenol-3-glucuronide) was found impairing the interaction with the ribosome, while the other compounds tested (i.e. neosolaniol, nivalenol, fusarenon-X, diacetoxyscirpenol, NT-1 toxin, HT-2 toxin, 19- and 20-hydroxy-T-2 toxin, T-2 toxin triol and tetraol, and 15-deacetyl-T-2 toxin), were found potentially able to inhibit the ribosome. Accordingly, they should be included with high priority in further risk assessment studies in order to better characterize the trichothecenes-related hazard. Copyright © 2017 Elsevier B.V. All rights reserved.

Jasmonate-Mediated Induced Volatiles in the American Cranberry, Vaccinium macrocarpon: From Gene Expression to Organismal Interactions.

PubMed

Rodriguez-Saona, Cesar R; Polashock, James; Malo, Edi A

2013-01-01

Jasmonates, i.e., jasmonic acid (JA) and methyl jasmonate (MeJA), are signaling hormones that regulate a large number of defense responses in plants which in turn affect the plants' interactions with herbivores and their natural enemies. Here, we investigated the effect of jasmonates on the emission of volatiles in the American cranberry, Vaccinium macrocarpon, at different levels of biological organization from gene expression to organismal interactions. At the molecular level, four genes (BCS, LLS, NER1, and TPS21) responded significantly to gypsy moth larval feeding, MeJA, and mechanical wounding, but to different degrees. The most dramatic changes in expression of BCS and TPS21 (genes in the sesquiterpenoid pathway) were when treated with MeJA. Gypsy moth-damaged and MeJA-treated plants also had significantly elevated expression of LLS and NER1 (genes in the monoterpene and homoterpene biosynthesis pathways, respectively). At the biochemical level, MeJA induced a complex blend of monoterpene and sesquiterpene compounds that differed from gypsy moth and mechanical damage, and followed a diurnal pattern of emission. At the organismal level, numbers of Sparganothis sulfureana moths were lower while numbers of parasitic wasps were higher on sticky traps near MeJA-treated cranberry plants than those near untreated plants. Out of 11 leaf volatiles tested, (Z)-3-hexenyl acetate, linalool, and linalool oxide elicited strong antennal (EAG) responses from S. sulfureana, whereas sesquiterpenes elicited weak EAG responses. In addition, mortality of S. sulfureana larvae increased by about 43% in JA treated cranberry plants as compared with untreated plants, indicating a relationship among adult preference, antennal sensitivity to plant odors, and offspring performance. This study highlights the role of the jasmonate-dependent defensive pathway in the emissions of herbivore-induced volatiles in cranberries and its importance in multi-trophic level interactions.

Composition and Antibacterial Activity of the Essential Oils of Orthosiphon stamineus Benth and Ficus deltoidea Jack against Pathogenic Oral Bacteria.

PubMed

Azizan, Nuramirah; Mohd Said, Shahida; Zainal Abidin, Zamirah; Jantan, Ibrahim

2017-12-05

In this study, the essential oils of Orthosiphon stamineus Benth and Ficus deltoidea Jack were evaluated for their antibacterial activity against invasive oral pathogens, namely Enterococcus faecalis , Streptococcus mutans , Streptococcus mitis , Streptococcus salivarius , Aggregatibacter actinomycetemcomitans , Porphyromonas gingivalis and Fusobacterium nucleatum . Chemical composition of the oils was analyzed using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The antibacterial activity of the oils and their major constituents were investigated using the broth microdilution method (minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC)). Susceptibility test, anti-adhesion, anti-biofilm, checkerboard and time-kill assays were also carried out. Physiological changes of the bacterial cells after exposure to the oils were observed under the field emission scanning electron microscope (FESEM). O. stamineus and F. deltoidea oils mainly consisted of sesquiterpenoids (44.6% and 60.9%, respectively), and β-caryophyllene was the most abundant compound in both oils (26.3% and 36.3%, respectively). Other compounds present in O. stamineus were α-humulene (5.1%) and eugenol (8.1%), while α-humulene (5.5%) and germacrene D (7.7%) were dominant in F. deltoidea . The oils of both plants showed moderate to strong inhibition against all tested bacteria with MIC and MBC values ranging 0.63-2.5 mg/mL. However, none showed any inhibition on monospecies biofilms. The time-kill assay showed that combination of both oils with amoxicillin at concentrations of 1× and 2× MIC values demonstrated additive antibacterial effect. The FESEM study showed that both oils produced significant alterations on the cells of Gram-negative bacteria as they became pleomorphic and lysed. In conclusion, the study indicated that the oils of O. stamineus and F. deltoidea possessed moderate to strong antibacterial properties against the seven strains pathogenic oral bacteria and may have caused disturbances of membrane structure or cell wall of the bacteria.

Tyrosinase inhibitory activity, molecular docking studies and antioxidant potential of chemotypes of Lippia origanoides (Verbenaceae) essential oils

PubMed Central

Silva, Natália de F.; Andrade, Eloísa Helena A.; Gratieri, Tais; Setzer, William N.; Maia, José Guilherme S.

2017-01-01

The essential oils (EOs) of the aerial parts of Lippia origanoides (LiOr), collected in different localities of the Amazon region, were obtained by hydrodistillation and analyzed by GC and CG-MS. Principle component analysis (PCA) based on chemical composition grouped the oils in four chemotypes rich in mono- and sesquiterpenoids. Group I was characterized by 1,8-cineole and α-terpineol (LiOr-1 and LiOr-4) and group II by thymol (LiOr-2). The oil LiOr-3 showed β-caryophyllene, α-phellandrene and β-phellandrene as predominant and LiOr-5 was rich in (E)-nerolidol and β-caryophyllene. All samples were evaluated for antioxidant activity and inhibition of tyrosinase in vitro and in silico. The highest antioxidant activity by the DPPH free radical method was observed in LiOr-2 and LiOr-5 oils (132.1 and 82.7 mg TE∙mL-1, respectively). The tyrosinase inhibition potential was performed using L-tyrosine and L-DOPA as substrates and all samples were more effective in the first step of oxidation. The inhibition by samples LiOr-2 and LiOr-4 were 84.7% and 62.6%, respectively. The samples LiOr-1, LiOr-4 and LiOr-5 displayed an interaction with copper (II) ion with bathochromic shift around 15 nm. In order to elucidate the mechanism of inhibition of the main compounds, a molecular docking study was carried out. All compounds displayed an interaction between an oxygen and Cu or histidine residues with distances less than 4 Å. The best docking energies were observed with thymol and (E)-nerolidol (-79.8 kcal.mol-1), which suggested H-bonding interactions with Met281 and His263 (thymol) and His259, His263 ((E)-nerolidol). PMID:28459864

Novel beta-1,3-, 1,6-oligoglucan elicitor from Alternaria alternata 102 for defense responses in tobacco.

PubMed

Shinya, Tomonori; Ménard, Rozenn; Kozone, Ikuko; Matsuoka, Hideaki; Shibuya, Naoto; Kauffmann, Serge; Matsuoka, Ken; Saito, Mikako

2006-06-01

A novel elicitor that induces chitinases in tobacco BY-2 cells was isolated from Alternaria alternata 102. Six other fungi, including A. alternata IFO 6587, could not induce, or weakly induce chitinase activity. The purified elicitor was soluble in 75% methanol and showed the chitinase-inducing activity when applied at concentrations of as low as 25 ng x mL(-1). Structural determination by methylation analysis, reducing-end analysis, MALDI-TOF/MS, and NMR spectroscopy indicated that the elicitor was a mixture of beta-1,3-, 1,6-oligoglucans mostly with a degree of polymerization of between 8 and 17. Periodate oxidation of the elicitor suggested that the 1,6-linked and nonreducing terminal residues are essential for the elicitor activity. Further analysis of the elicitor responses in BY-2 cells indicated that the activity of this beta-1,3-, 1,6-glucan elicitor was about 1000 times more potent than that of laminarin, which is a known elicitor of defense responses in tobacco. Analyzing the expression of defense-related genes indicated that a phenylalanine ammonia-lyase gene and a coumaroyl-CoA O-methyltransferase gene were transiently expressed by this beta-1,3-, 1,6-glucan elicitor. The elicitor induced a weak oxidative burst but did not induce cell death in the BY-2 cells. In the tissue of tobacco plants, this beta-1,3-, 1,6-glucan elicitor induced the expression of basic PR-3 genes, the phenylpropanoid pathway genes, and the sesquiterpenoid pathway genes. In comparison with laminarin and laminarin sulfate, which are reported to be potent elicitors of defense responses in tobacco, the expression pattern of genes induced by the purified beta-1,3-, 1,6-glucan elicitor was more similar to that induced by laminarin than to that induced by laminarin sulfate.

Analysis of essential oils and fragrances with a new generation of highly inert gas chromatographic columns coated with ionic liquids.

PubMed

Cagliero, Cecilia; Bicchi, Carlo; Cordero, Chiara; Liberto, Erica; Rubiolo, Patrizia; Sgorbini, Barbara

2017-04-28

In the fields of essential oils and fragrances, samples often consist of mixtures of compounds with similar structural and physical characteristics (e.g. mono- and sesquiterpenoids), whose correct identification closely depends on the synergic combination of chromatographic and mass spectral data. This sample complexity means that new GC stationary phases with different selectivities are continually being investigated. Ionic liquids (ILs) are of great interest as GC stationary phases in this field because of their selectivity (significantly different than that of currently phases) and their high temperature stability. A first generation of IL GC columns was found to be competitive when applied to these field, in terms of selectivity and efficiency, compared to conventional columns (polydimethylsiloxane, (e.g. OV-1), methyl-polysiloxane 5%-phenyl (e.g. SE-52), 7%-cyanopropyl, 7%-phenyl polysiloxane (e.g. OV-1701), and polyethylen glycol (e.g. PEG-20M). However, these columns showed significant activity towards polar or active analytes, which primarily affected their quantitative performance. A new generation of highly-inactive columns coated with three of the most widely-used ionic liquid GC stationary phases has recently been introduced; these phases are SLB-IL60i (1,12-di(tripropylphosphonium) dodecane bis(trifluoromethylsulfonyl) imide [NTf 2 ], SLB-IL76i (tri-(tripropylphosphonium-hexanamido)-triethylamine [NTf 2 ]), and SLB-IL111i (1,5-di (2,3-dimethyllimidazolium) pentane [NTf 2 ]). This study carefully tested the new inert IL columns, in view of their routine application in the fragrance and essential oil fields. They were found to have unusually high selectivity, comparable to that of first-generation IL columns, while their inertness and efficiency were competitive with those of currently-used conventional columns. The IL column performance of first and second generations was compared, through the quali-quantitative analysis of components in a group of different complexity samples; these included the Grob test, a standard mixture of "suspected" skin allergens, and the essential oils of chamomile and sandalwood. Copyright © 2017 Elsevier B.V. All rights reserved.

Psychoneuropharmacological activities and chemical composition of essential oil of fresh fruits of Piper guineense (Piperaceae) in mice.

PubMed

Oyemitan, Idris Ajayi; Olayera, Omotola Aanuoluwa; Alabi, Akeeb; Abass, Luqman Adewale; Elusiyan, Christianah Abimbola; Oyedeji, Adebola Omowumi; Akanmu, Moses Atanda

2015-05-26

Piper guineense Schum & Thonn (Piperaceae) is a medicinal plant used in the Southern States of Nigeria to treat fever, mental disorders and febrile convulsions. This study aims at determining the chemical composition and the central nervous system (CNS) activities of the essential oil obtained from the plant׳s fresh fruits in order to rationalize its folkloric use. Essential oil of P. guineense (EOPG) obtained by hydrodistillation was analysed by GC/MS. EOPG (50-200mg/kg, i.p.) was evaluated for behavioural, hypothermic, sedative, muscle relaxant, anti-psychotic and anticonvulsant activities using standard procedures. Analysis of the oil reveals 44 compounds of which 30 compounds constituting 84.7% were identified. The oil was characterized by sesquiterpenoids (64.4%) while only four monoterpeneoids (21.3%) were found present in the oil. Major compounds identified were β-sesquiphellandrene (20.9%), linalool (6.1%), limonene (5.8%), Z-β-bisabolene (5.4%) and α-pinene (5.3%). The EOPG (50-200mg/kg, i.p.) caused significant (p<0.01) inhibition on rearing {F(4,20)=43}, locomotor {F(4,20)=22} activity and decreased head dips in hole board {F(4,20)=7} indicating CNS depressant effect; decreased rectal temperature {F(4,20)=7-16}, signifying hypothermic activity; decreased ketamine-induced sleep latency {F(4,20)=7.8} and prolonged total sleeping time {F(4,20)=8.8}, indicating sedative effect; reduced muscular tone on the hind-limb grip test {F(4,20)=22}, inclined board {F(4,20)=4-49} and rota rod {F(4,20)=13-106}, implying muscle relaxant activity; induced catalepsy {F(4,20)=47-136}, inhibited apomorphine-induced climbing behaviour {F(4,20)=9} and inhibited apomorphine-induced locomotor {F(4,20)=16}, suggesting anti-psychotic effect; and protected mice against pentylenetetrazole-induced convulsions, indicating anticonvulsant potential. The most abundant component of the fresh fruits essential oil of P. guineense was β-sesquiphellandrene (20.9%); and the oil possesses CNS depressant, hypothermic, sedative, muscle relaxant, antipsychotic and anticonvulsant activities, thus providing scientific basis for its ethnomedicinal applications. Copyright © 2015 Elsevier Ireland Ltd. All rights reserved.

Chemical Composition and In Vitro Cytotoxicity of Essential Oils from Leaves and Flowers of Callistemon citrinus from Western Himalayas.

PubMed

Kumar, Dharmesh; Sukapaka, Mahesh; Babu, G D Kiran; Padwad, Yogendra

2015-01-01

Plant-based traditional system of medicine continues to play an important role in healthcare. In order to find new potent source of bioactive molecules, we studied the cytotoxic activity of the essential oils from the flowers and leaves of Callistemon citrinus. This is the first report on anticancer potential of essential oils of C. citrinus. Cytotoxicity of essential oil was evaluated using sulfo-rhodamine B (SRB) assay against human lung carcinoma (A549), rat glioma (C-6), human colon cancer (Colo-205) and human cervical cancer (SiHa) cells. Apoptosis induction was evaluated by caspase-3/7 activity which was further confirmed by western blotting. Percentage cell apoptosis was determined by Annexin V based dead cell assay followed by DNA content as cell cycle analysis against A549 and C-6 cells. While 3-(4,5-dimethythiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay was used to check the toxicity against normal human peripheral blood mononuclear cells (PBMCs), the immunomodulatory activity on mouse splenocytes was evaluated using SRB assay. The GC and GC-MS analysis of these essential oils revealed high content of α-pinene (32.3%), limonene (13.1%) and α-terpineol (14.6%) in leaf sample, whereas the flower oil was dominated by 1,8-cineole (36.6%) followed by α-pinene (29.7%). The leaf oil contained higher amount of monoterpene hydrocarbons (52.1%) and sesquiterpenoids (14%) as compared to flower oil (44.6% and 1.2%, respectively). However, the flower oil was predominant in oxygenated monoterpenes (43.5%). Although both leaf and flower oils showed highest cytotoxicity on A549 cells (61.4%±5.0 and 66.7%±2.2, respectively), only 100 μg/mL flower oil was significantly active against C-6 cells (69.1%±3.1). Interestingly, no toxicity was recorded on normal cells. Higher concentration of 1,8-cineole and/or synergistic effect of the overall composition were probably responsible for the efficacy of flower and leaf oils against the tested cells. These oils may form potential source of natural anti-cancer compounds and play important role in human health.

Ethnobotany, phytochemistry and pharmacology of Arctotis arctotoides (L.f.) O. Hoffm.: A review.

PubMed

Saleh-E-In, Md Moshfekus; Van Staden, Johannes

2018-06-28

Arctotis arctotoides (Asteraceae) is part of the genus Arctotis. Arctotis is an African genus of approximately 70 species that occur widely in the African continent with diverse medicinal values. This plant is used for the treatment of indigestion and catarrh of the stomach, epilepsy, topical wounds and skin disorders among the ethnic groups in South Africa and reported to have a wide spectrum of pharmacological properties. The aim of the present review is to appraise the botany, traditional uses, phytochemistry, pharmacological potential, analytical methods and safety issues of A. arctotoides. Additionally, this review will help to fill the existing gaps in knowledge and highlight further research prospects in the field of phytochemistry and pharmacology. Information on A. arctotoides was collected from various resources, including books on African medicinal herbs and Zulu medicinal plants, theses, reports and the internet databases such as SciFinder, Google Scholar, Pubmed, Scopus, Web of Science, and Mendeley by using a combination of various meaningful keywords. This review surveys the available literature of the species from 1962 to April 2017. In vitro and in vivo studies of the medicinal properties of A. arctotoides were reviewed. The main isolated and identified compounds were reported as sesquiterpenes, farnesol derivatives, germacranolide, guaianolides and some steroids, of which, nine were reported as antimicrobial. Monoterpenoids and sesquiterpenoids were the predominant essential oil compound classes of the leaves, flowers, stems and roots. The present review revealed potential pharmacological properties such as anti-oxidant, antibacterial, antifungal and anticancer activities of plant extracts as well as isolated compounds. Moreover, the review reports the safety profile (toxicity) of the crude extracts that had been screened on brine shrimps, rats and human cell lines. The present review has focused on the phytochemistry, botany, ethnopharmacology, biological activities and toxicological information of A. arctotoides. On the basis of reported data, A. arctotoides has emerged as a good source of natural medicine for the treatment of microbial infections, skin diseases, anti-inflammatory and anticancer agents and also provides new insights for further isolation of new bioactive compounds, especially the discovery of antimicrobial, anti-inflammatory and anticancer novel therapeutic lead drug molecules. Additionally, intensive investigations regarding pharmacological properties, safety assessment and efficacy with their mechanism of action could be future research interests before starting clinical trials for medicinal practices. Copyright © 2018 Elsevier B.V. All rights reserved.

Chemical Composition and In Vitro Cytotoxicity of Essential Oils from Leaves and Flowers of Callistemon citrinus from Western Himalayas

PubMed Central

Kumar, Dharmesh; Sukapaka, Mahesh; Babu, G. D. Kiran; Padwad, Yogendra

2015-01-01

Background Plant-based traditional system of medicine continues to play an important role in healthcare. In order to find new potent source of bioactive molecules, we studied the cytotoxic activity of the essential oils from the flowers and leaves of Callistemon citrinus. This is the first report on anticancer potential of essential oils of C. citrinus. Methods Cytotoxicity of essential oil was evaluated using sulfo-rhodamine B (SRB) assay against human lung carcinoma (A549), rat glioma (C-6), human colon cancer (Colo-205) and human cervical cancer (SiHa) cells. Apoptosis induction was evaluated by caspase-3/7 activity which was further confirmed by western blotting. Percentage cell apoptosis was determined by Annexin V based dead cell assay followed by DNA content as cell cycle analysis against A549 and C-6 cells. While 3-(4,5-dimethythiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay was used to check the toxicity against normal human peripheral blood mononuclear cells (PBMCs), the immunomodulatory activity on mouse splenocytes was evaluated using SRB assay. Results The GC and GC-MS analysis of these essential oils revealed high content of α-pinene (32.3%), limonene (13.1%) and α-terpineol (14.6%) in leaf sample, whereas the flower oil was dominated by 1,8-cineole (36.6%) followed by α-pinene (29.7%). The leaf oil contained higher amount of monoterpene hydrocarbons (52.1%) and sesquiterpenoids (14%) as compared to flower oil (44.6% and 1.2%, respectively). However, the flower oil was predominant in oxygenated monoterpenes (43.5%). Although both leaf and flower oils showed highest cytotoxicity on A549 cells (61.4%±5.0 and 66.7%±2.2, respectively), only 100 μg/mL flower oil was significantly active against C-6 cells (69.1%±3.1). Interestingly, no toxicity was recorded on normal cells. Conclusion Higher concentration of 1,8-cineole and/or synergistic effect of the overall composition were probably responsible for the efficacy of flower and leaf oils against the tested cells. These oils may form potential source of natural anti-cancer compounds and play important role in human health. PMID:26308916

Could essential oils enhance biopolymers performance for wound healing? A systematic review.

PubMed

Pérez-Recalde, Mercedes; Ruiz Arias, Ignacio E; Hermida, Élida B

2018-01-01

Millions of people in the world suffer from chronic wounds of different etiologies such as diabetic foot and leg ulcers, without solutions nowadays. Molecules obtained from plants offer an alternative to aid wound healing. Strong evidence about essential oils (EO) anti-inflammatory and antimicrobial properties is thoroughly described in literature and their chemical compositions are well characterized. More recently, EO effects in experimental wounds have begun to be analyzed. We aim to summarize the evidence of EO in experimental wounds, and the possibility of combining them with biopolymers commonly used in skin regeneration. Electronic databases such as ScienceDirect, PubMed and Scopus were used to search scientific contributions until March 2017, using relevant keywords. In a first step, literature focusing on EO and/or mono- or sesqui-terpenoids effects in rodent wounds was identified and summarized. In all cases, chemical structures and EO composition were detailed, as well as references to in vitro activities previously determined, e.g. antibacterial, antioxidant or anti-inflammatory. In a second step, scientific literature devoted to combine EO and biopolymers with the focus set on wound healing innovations, was collected and analyzed. Treatments with EO from species of genders Lavandula, Croton, Blumea, Eucalyptus, Pinus, Cymbopogon, Eucalyptus, Cedrus, Abies, Rosmarinus, Origanum, Salvia and Plectranthus, have shown positive results in rodent wounds. All of these EO were mainly composed by monoterpenoids-thymol, 1,8-cineole, linalool-or monoterpenes, as limonene or pinenes. Experimental wounds in rodents have shown faster closure rate, better collagen deposition and/or enhanced fibroblasts proliferation. In blends with biopolymers, several EO combined with chitosan, alginate, gelatin or collagen, were processed to give active films or nanofibers, with antioxidant, anti-inflammatory or antimicrobial activities. Curiously, all of these works were carried out since 2010. There is significant evidence about the effectivity of EO as wound healers. The incorporation of EO into a polymer matrix that contributes to wound healing is still incipient. However, scientific based evidence of the EO incorporation in resorbable polymeric scaffolds was found and analyzed herein. In summary, EO-biopolymer dressings or scaffolds have become promising artifacts regarding wound treatments, especially in chronic wounds, where treating infection and inflammation are still important issues. Copyright © 2017 Elsevier GmbH. All rights reserved.

Chemical and Antimicrobial Analyses of Sideritis romana L. subsp. purpurea (Tal. ex Benth.) Heywood, an Endemic of the Western Balkan.

PubMed

Tadić, Vanja; Oliva, Alessandra; Božović, Mijat; Cipolla, Alessia; De Angelis, Massimiliano; Vullo, Vincenzo; Garzoli, Stefania; Ragno, Rino

2017-08-23

A comprehensive study on essential oil and different solvent extracts of Sideritis romana L. subsp. purpurea (Tal. ex Benth.) Heywood (Lamiaceae) from Montenegro is reported. The gas chromatography-mass spectrometry analysis of the essential oil revealed a total of 43 components with bicyclogermacrene (23.8%), germacrene D (8%), ( E )-caryophyllene (7.9%) and spathulenol (5.5%) as the major ones. Sesquiterpenoid group was found to be the most dominant one (64.8%), with 19.9% of the oxygenated forms. In the crude methanol extract of the investigated plant, obtained by Sohhlet exraction, the total phenol content was 14.7 ± 0.4 mg of GA/g, the total flavonoids were 0.29 ± 0.03% expressed as hyperoside percentage, whereas the total tannins content was 0.22 ± 0.04% expressed as pyrogallol percentage. For the antimicrobial activity determination, the following microorganisms have been used: methicillin-susceptible Staphylococcus aureus (MSSA (American Type Culture Collection (ATCC) 29213)) and methicillin-resistant S. aureus (MRSA (clinical strain)), Escherichia coli (ATCC 25922), carbapenem-susceptible Klebsiella pneumoniae (clinical strain), carbapenem-resistant K. pneumoniae (clinical strain) and Candida albicans (ATCC 14053). The essential oil showed high potency against MSSA and MRSA, both at high (~5 × 10⁵ CFU/mL) and low (~5 × 10³ CFU/mL) inoculum. With respect to MSSA, the minimal inhibitory concentration (MIC) value was 0.307 mg/mL, with bactericidal activity obtained at 0.615 mg/mL, while, in the case of MRSA, the MIC and minimal bactericidal concentration (MBC) values were 0.076 and 0.153 mg/mL, respectively. Regarding anti- Candida albicans activity, the MIC value was 2.46 mg/mL without reaching fungicidal activity. In addition to the observed essential oil efficacy, different solvent extracts were analyzed for their antimicrobial activity. Similarly to the essential oil, thehighest efficacy was observed against both MSSA and MRSA strains, at high and low inoculums, in the case of the 1,2-dichloroethane and methanol extracts. A potent fungicidal activity has been also found for the n -hexane and 1,2-dichloroethane extracts. It can be concluded that Sideritis romana L. subsp. purpurea (Tal. ex Benth.) Heywood provides a wide range of application in different fields such as phytochemistry, pharmacology, toxicology or pharmacognosy.

Transcriptomic analysis reveals the gene expression profile that specifically responds to IBA during adventitious rooting in mung bean seedlings.

PubMed

Li, Shi-Weng; Shi, Rui-Fang; Leng, Yan; Zhou, Yuan

2016-01-12

Auxin plays a critical role in inducing adventitious rooting in many plants. Indole-3-butyric acid (IBA) is the most widely employed auxin for adventitious rooting. However, the molecular mechanisms by which auxin regulate the process of adventitious rooting are less well known. The RNA-Seq data analysis indicated that IBA treatment greatly increased the amount of clean reads and the amount of expressed unigenes by 24.29 % and 27.42 % and by 4.3 % and 5.04 % at two time points, respectively, and significantly increased the numbers of unigenes numbered with RPKM = 10-100 and RPKM = 500-1000 by 13.04 % and 3.12 % and by 24.66 % and 108.2 % at two time points, respectively. Gene Ontology (GO) enrichment analysis indicated that the enrichment of down-regulated GOs was 2.87-fold higher than that of up-regulated GOs at stage 1, suggesting that IBA significantly down-regulated gene expression at 6 h. The GO functional category indicated that IBA significantly up- or down-regulated processes associated with auxin signaling, ribosome assembly and protein synthesis, photosynthesis, oxidoreductase activity and extracellular region, secondary cell wall biogenesis, and the cell wall during the development process. Kyoto Encyclopedia of Genes and Genomes (KEGG) pathway enrichment indicated that ribosome biogenesis, plant hormone signal transduction, pentose and glucuronate interconversions, photosynthesis, phenylpropanoid biosynthesis, sesquiterpenoid and triterpenoid biosynthesis, ribosome, cutin, flavonoid biosynthesis, and phenylalanine metabolism were the pathways most highly regulated by IBA. A total of 6369 differentially expressed (2-fold change > 2) unigenes (DEGs) with 3693 (58 %) that were up-regulated and 2676 (42 %) down-regulated, 5433 unigenes with 2208 (40.6 %) that were up-regulated and 3225 (59.4 %) down-regulated, and 7664 unigenes with 3187 (41.6 %) that were up-regulated and 4477 (58.4 %) down-regulated were detected at stage 1, stage 2, and between stage 1 and stage 2, respectively, suggesting that IBA treatment increased the number of DEGs. A total of 143 DEGs specifically involved in plant hormone signaling and 345 transcription factor (TF) genes were also regulated by IBA. qRT-PCR validation of the 36 genes with known functions indicated a strong correlation with the RNA-Seq data. The changes in GO functional categories, KEGG pathways, and global DEG profiling during adventitious rooting induced by IBA were analyzed. These results provide valuable information about the molecular traits of IBA regulation of adventitious rooting.

Enhanced artemisinin yield by expression of rol genes in Artemisia annua.

PubMed

Dilshad, Erum; Cusido, Rosa Maria; Palazon, Javier; Estrada, Karla Ramirez; Bonfill, Mercedes; Mirza, Bushra

2015-10-29

Despite of many advances in the treatment of malaria, it is still the fifth most prevalent disease worldwide and is one of the major causes of death in the developing countries which accounted for 584,000 deaths in 2013, as estimated by World Health Organization. Artemisinin from Artemisia annua is still one of the most effective treatments for malaria. Increasing the artemisinin content of A. annua plants by genetic engineering would improve the availability of this much-needed drug. In this regard, a high artemisinin-yielding hybrid of A. annua produced by the centre for novel agricultural products of the University of York, UK, was selected (artemisinin maximally 1.4 %). As rol genes are potential candidates of biochemical engineering, genetic transformation of A. annua with Agrobacterium tumefaciens GV3101 harbouring vectors with rol B and rol C genes was carried out with the objective of enhancement of artemisinin content. Transgenic lines produced were analysed by the LC-MS for quantitative analysis of artemisinin and analogues. These high artemisinin yielding transgenics were also analysed by real time quantitative PCR to find the molecular dynamics of artemisinin enhancement. Genes of artemisinin biosynthetic pathway were studied including amorphadiene synthase (ADS), cytochrome P450, (CYP71AV1) and aldehyde dehydrogenase 1 (ALDH1). Trichome-specific fatty acyl-CoA reductase 1(TAFR1) is an enzyme involved in both trichome development and sesquiterpenoid biosynthesis and both processes are important for artemisinin biosynthesis. Thus, real time qPCR analysis of the TAFR1 gene was carried out, and trichome density was determined. Transgenics of rol B gene showed two- to ninefold (the decimal adds nothing in the abstract, please simplify to two- to ninefold) increase in artemisinin, 4-12-fold increase in artesunate and 1.2-3-fold increase in dihydroartemisinin. Whereas in the case of rol C gene transformants, a fourfold increase in artemisinin, four to ninefold increase in artesunate and one- to twofold increase in dihydroartemisinin concentration was observed. Transformants with the rol B gene had higher expression of these genes than rol C transformants. TAFR1 was also found to be more expressed in rol gene transgenics than wild type A. annua, which was also in accordance with the trichome density of the respective plant. Thus it was proved that rol B and rol C genes are effective in the enhancement of artemisinin content of A. annua, rol B gene being more active to play part in this enhancement than rol C gene.

Cellular engineering of Artemisia annua and Artemisia dubia with the rol ABC genes for enhanced production of potent anti-malarial drug artemisinin.

PubMed

Kiani, Bushra Hafeez; Suberu, John; Mirza, Bushra

2016-05-04

Malaria is causing more than half of a million deaths and 214 million clinical cases annually. Despite tremendous efforts for the control of malaria, the global morbidity and mortality have not been significantly changed in the last 50 years. Artemisinin, extracted from the medicinal plant Artemisia sp. is an effective anti-malarial drug. In 2015, elucidation of the effectiveness of artemisinin as a potent anti-malarial drug was acknowledged with a Nobel prize. Owing to the tight market and low yield of artemisinin, an economical way to increase its production is to increase its content in Artemisia sp. through different biotechnological approaches including genetic transformation. Artemisia annua and Artemisia dubia were transformed with rol ABC genes through Agrobacterium tumefacienes and Agrobacterium rhizogenes methods. The artemisinin content was analysed and compared between transformed and untransformed plants with the help of LC-MS/MS. Expression of key genes [Cytochrome P450 (CYP71AV1), aldehyde dehydrogenase 1 (ALDH1), amorpha-4, 11 diene synthase (ADS)] in the biosynthetic pathway of artemisinin and gene for trichome development and sesquiterpenoid biosynthetic (TFAR1) were measured using Quantitative real time PCR (qRT-PCR). Trichome density was analysed using confocal microscope. Artemisinin content was significantly increased in transformed material of both Artemisia species when compared to un-transformed plants. The artemisinin content within leaves of transformed lines was increased by a factor of nine, indicating that the plant is capable of synthesizing much higher amounts than has been achieved so far through traditional breeding. Expression of all artemisinin biosynthesis genes was significantly increased, although variation between the genes was observed. CYP71AV1 and ALDH1 expression levels were higher than that of ADS. Levels of the TFAR1 expression were also increased in all transgenic lines. Trichome density was also significantly increased in the leaves of transformed plants, but no trichomes were found in control roots or transformed roots. The detection of significantly raised levels of expression of the genes involved in artemisinin biosynthesis in transformed roots correlated with the production of significant amounts of artemisinin in these tissues. This suggests that synthesis is occurring in tissues other than the trichomes, which contradicts previous theories. Transformation of Artemisia sp. with rol ABC genes can lead to the increased production of artemisinin, which will help to meet the increasing demand of artemisinin because of its diverse pharmacological and anti-malarial importance.

Organic geochemistry and petrology of subsurface Paleocene-Eocene Wilcox and Claiborne Group coal beds, Zavala County, Maverick Basin, Texas, USA

USGS Publications Warehouse

Hackley, Paul C.; Warwick, Peter D.; Hook, Robert W.; Alimi, Hossein; Mastalerz, Maria; Swanson, Sharon M.

2012-01-01

Coal samples from a coalbed methane exploration well in northern Zavala County, Maverick Basin, Texas, were characterized through an integrated analytical program. The well was drilled in February, 2006 and shut in after coal core desorption indicated negligible gas content. Cuttings samples from two levels in the Eocene Claiborne Group were evaluated by way of petrographic techniques and Rock–Eval pyrolysis. Core samples from the Paleocene–Eocene Indio Formation (Wilcox Group) were characterized via proximate–ultimate analysis in addition to petrography and pyrolysis. Two Indio Formation coal samples were selected for detailed evaluation via gas chromatography, and Fourier transform infrared (FTIR) and 13C CPMAS NMR spectroscopy. Samples are subbituminous rank as determined from multiple thermal maturity parameters. Elevated rank (relative to similar age coal beds elsewhere in the Gulf Coast Basin) in the study area is interpreted to be a result of stratigraphic and/or structural thickening related to Laramide compression and construction of the Sierra Madre Oriental to the southwest. Vitrinite reflectance data, along with extant data, suggest the presence of an erosional unconformity or change in regional heat flow between the Cretaceous and Tertiary sections and erosion of up to >5 km over the Cretaceous. The presence of liptinite-rich coals in the Claiborne at the well site may indicate moderately persistent or recurring coal-forming paleoenvironments, interpreted as perennially submerged peat in shallow ephemeral lakes with herbaceous and/or flotant vegetation. However, significant continuity of individual Eocene coal beds in the subsurface is not suggested. Indio Formation coal samples contain abundant telovitrinite interpreted to be preserved from arborescent, above-ground woody vegetation that developed during the middle portion of mire development in forested swamps. Other petrographic criteria suggest enhanced biological, chemical and physical degradation at the beginning and end of Indio mire development. Fluorescence spectra of sporinite and resinite are consistent and distinctly different from each other, attributed to the presence of a greater proportion of complex asphaltene and polar molecules in resinite. Gas chromatography of resinite-rich coal shows sesquiterpenoid and diterpenoid peaks in the C14–17 range, which are not present in resinite-poor coal. Quantities of extracts suggest bitumen concentration below the threshold for effective source rocks [30–50 mg hydrocarbon/g total organic carbon (HC/g TOC)]. Saturate/aromatic and pristane/phytane (Pr/Ph) ratios are different from values for nearby Tertiary-reservoired crude oil, suggesting that the Indio coals are too immature to source liquid hydrocarbons in the area. However, moderately high HI values (200–400 mg HC/g rock) may suggest some potential for naphthenic–paraffinic oil generation where buried more deeply down stratigraphic/structural dip. Extractable phenols and C20+ alkanes are suggested as possible intermediates for acetate fermentation in microbial methanogenesis which may, however, be limited by poor nutrient supply related to low rainfall and meteoric recharge rate or high local sulfate concentration.