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Sample records for laevad olid puust

  1. Synthesis and antifungal activity of 7-methyl-7-hydroxy-2,3-benzo[c]octa-1,6-olide.

    PubMed

    Zhao, Jin; Dong, Hong-Bo; Yang, Ming-Yan; Du, Juan; Jiang, Jia-Zheng; Wang, Ming-An

    2014-01-01

    The racemic 7-methyl-7-hydroxy-2,3-benzo[c]octa-1,6-olide, the analog of natural product (6R)-3,7-dimethyl-7-hydroxy-2-octen-1,6-olide, was totally synthesized using easily available (E)-2-(2-carboxyvinyl)benzoic acid as a raw material in nine-step reactions including three key steps of Wittig reaction, epoxidation, and cyclization, with an overall yield of 10.3%. The bioassay results showed that ( ± )-2 exhibited stronger antifungal activity than the natural product ( ± )-1 and (R)-1 against Alternaria solani with an EC₅₀ value of 27.36 μg/ml. PMID:24456253

  2. Two new 11alpha,12alpha-epoxy-ursan-28,13beta-olides and other triterpenes from Cecropia catharinensis.

    PubMed

    Machado, E C; Yunes, R A; Malheiros, A; Gomez, E C; Delle Monache, F

    2008-01-01

    Three new triterpenes, 2alpha-acetoxy-3beta,19alpha-dihydroxy-11alpha,12alpha-epoxy-ursan-28,13beta-olide, 3beta-acetoxy-2alpha,19alpha-dihydroxy-11alpha,12alpha-epoxy-ursan-28,13beta-olide and 2-O-acetyl-euscaphic acid together eight known triterpenes were isolated from the roots and stems of Cecropia catharinensis. Their structures were determined by detailed analysis of NMR spectra and the relative configurations established by difference nOe experiments. In addition, four flavonoid glucosides (vitexin, isovitexin, orientin and isoorientin) were found in the leaves.

  3. 2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides: synthesis, reactions and biological activity.

    PubMed

    Husain, Asif; Khan, M S Y; Hasan, S M; Alam, M M

    2005-12-01

    2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides (1-17) were prepared from 3-(4-phenoxy-benzoyl)propionic acid and aromatic aldehydes. Some of the selected butenolides were reacted with ammonia and benzylamine to give corresponding 3-arylidene-5-(4-phenoxy-phenyl)-2(3H)-pyrrolones (18-23) and 3-arylidene-5-(4-phenoxy-phenyl)-1-benzyl-2(3H)-pyrrolones (24-29) respectively, which were characterized on the basis of 1H-, 13C-NMR, Mass spectrometric data and elemental analysis results. These compounds were tested for anti-inflammatory and antimicrobial actions. The compounds, which showed significant anti-inflammatory activity, were screened for their analgesic and ulcerogenic activities. Five new compounds (5, 6, 7, 25 and 26), out of 29 showed very good anti-inflammatory activity in the carrageenan induced rat paw edema test, with significant analgesic activity in the acetic acid induced writhing test together with negligible ulcerogenic action. Antibacterial activity against Staphylococcus aureus and Escherichia coli as well as antifungal activity against Candida albicans were expressed as the corresponding minimum inhibitory concentration (MIC) values. Compound 21, 22 and 23 showed excellent activity against C. albicans with MIC-10 microg/ml. Out of the above-mentioned compounds, 22 and 23 also showed good activity against S. aureus with MIC-20 and 15 microg/ml respectively. PMID:15878219

  4. Production of a highly potent epoxide through the microbial metabolism of 3β-acetoxyurs-11-en-13β,28-olide by Aspergillus niger culture.

    PubMed

    Ali, Sajid; Nisar, Muhammad; Gulab, Hussain

    2016-09-01

    Context 3β-Acetoxyurs-11-en-13β,28-olide (I), a triterpenoid, is found in most plant species. Pharmacologically triterpenes are very effective compounds with potent anticancer, anti-HIV and antimicrobial activities. Objectives Microbial transformation of 3β-acetoxyurs-11-en-13β,28-olide (I) was performed in order to obtain derivatives with improved pharmacological potential. Materials and methods Compound (I, 100 mg) was incubated with Aspergillus niger culture for 12 d. The metabolite formed was purified through column chromatography. Structure elucidation was performed through extensive spectroscopy (IR, MS and NMR). In vitro α- and β-glucosidase inhibitory, and antiglycation potentials of both substrate and metabolite were evaluated. Results Structure of metabolite II was characterized as 3β-acetoxyurs-11,12-epoxy-13β,28-olide (II). Metabolite II was found to be an oxidized product of compound I. In vitro α- and β-glucosidases revealed that metabolite II was a potent and selective inhibitor of α-glucosidase (IC50 value = 3.56 ± 0.38 μM), showing that the inhibitory effect of metabolite II was far better than compound I (IC50 value = 14.7 ± 1.3 μM) as well as acarbose (IC50 value = 545 ± 7.9 μM). Antiglycation potential of compound II was also high with 82.51 ± 1.2% inhibition. Thus, through oxidation, the biological potential of the substrate molecule can be enhanced. Conclusion Biotransformation can be used as a potential tool for the production of biologically potent molecules.

  5. Production of a highly potent epoxide through the microbial metabolism of 3β-acetoxyurs-11-en-13β,28-olide by Aspergillus niger culture.

    PubMed

    Ali, Sajid; Nisar, Muhammad; Gulab, Hussain

    2016-09-01

    Context 3β-Acetoxyurs-11-en-13β,28-olide (I), a triterpenoid, is found in most plant species. Pharmacologically triterpenes are very effective compounds with potent anticancer, anti-HIV and antimicrobial activities. Objectives Microbial transformation of 3β-acetoxyurs-11-en-13β,28-olide (I) was performed in order to obtain derivatives with improved pharmacological potential. Materials and methods Compound (I, 100 mg) was incubated with Aspergillus niger culture for 12 d. The metabolite formed was purified through column chromatography. Structure elucidation was performed through extensive spectroscopy (IR, MS and NMR). In vitro α- and β-glucosidase inhibitory, and antiglycation potentials of both substrate and metabolite were evaluated. Results Structure of metabolite II was characterized as 3β-acetoxyurs-11,12-epoxy-13β,28-olide (II). Metabolite II was found to be an oxidized product of compound I. In vitro α- and β-glucosidases revealed that metabolite II was a potent and selective inhibitor of α-glucosidase (IC50 value = 3.56 ± 0.38 μM), showing that the inhibitory effect of metabolite II was far better than compound I (IC50 value = 14.7 ± 1.3 μM) as well as acarbose (IC50 value = 545 ± 7.9 μM). Antiglycation potential of compound II was also high with 82.51 ± 1.2% inhibition. Thus, through oxidation, the biological potential of the substrate molecule can be enhanced. Conclusion Biotransformation can be used as a potential tool for the production of biologically potent molecules. PMID:26736075

  6. Bioactive (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids from the South China Sea gorgonian Dichotella gemmacea.

    PubMed

    Li, Cui; La, Ming-Ping; Sun, Peng; Kurtan, Tibor; Mandi, Attila; Tang, Hua; Liu, Bao-Shu; Yi, Yang-Hua; Li, Ling; Zhang, Wen

    2011-01-01

    Six new (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids, gemmacolides N-S (1-6), were isolated together with four known analogues, juncenolide D, and juncins R, S and U (7-10), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by the detailed analysis of spectroscopic data in combination with the comparison with reported data. The absolute configuration of 1 was determined by a TDDFT calculation of its solution ECD spectrum, affording the determination of absolute configuration of other analogues by simply comparing their ECD spectra with that of 1. The cytotoxic and antimicrobial activities of these compounds were evaluated. In preliminary in vitro bioassays, compounds 4, 5, 6, 8 and 9 showed cytotoxicity against A549 and MG63, while compounds 1, 2, 4, 7-10 showed antimicrobial activity against the fungus Septoria tritici and the bacterium Escherichia coli.

  7. 16-hydroxy-cleroda-3,13-dien-16,15-olide induced glioma cell autophagy via ROS generation and activation of p38 MAPK and ERK-1/2.

    PubMed

    Thiyagarajan, Varadharajan; Sivalingam, Kalai Selvi; Viswanadha, Vijaya Padma; Weng, Ching-Feng

    2016-07-01

    16-hydroxy-cleroda-3,13-dien-16,15-olide (HCD), a natural product isolated from medicinal plant Polyalthia longifolia exhibits anticancer activity through caspase-independent apoptosis in brain tumors, as previously reported. This study further attempted to investigate the involvement of HCD-induced autophagy in brain tumor cell lines neuroblastoma N18 and glioma C6 through the induction of reactive oxygen species (ROS) and the activation of p38 and ERK-1/2 pathway. The results demonstrated that HCD increased the hyper-generation of ROS and decreased cellular antioxidant enzymes, such as superoxide dismutase (SOD), glutathione (GSH), glutathione peroxidase (GPx), and glutathione s transferase (GST). Furthermore, HCD increased the expressions of autophagic marker proteins LC3-II and Beclin-1 in a time- and dose-dependent manner. Additionally, HCD was found to significantly induce p-p38 MAPK and p-ERK-1/2 proteins by Western blot, which implies that HCD is a potential therapeutic anticancer agent that exerts its activity through inducing ROS-mediation for the autophagy of brain tumor cells.

  8. 4-Hydroxy-2,3-Dimethyl-2-Nonen-4-Olide Has an Inhibitory Effect on Pro-Inflammatory Cytokine Production in CpG-Stimulated Bone Marrow-Derived Dendritic Cells

    PubMed Central

    Manzoor, Zahid; Koo, Jung-Eun; Ali, Irshad; Kim, Jung-Eun; Byeon, Sang-Hee; Yoo, Eun-Sook; Kang, Hee-Kyoung; Hyun, Jin-Won; Lee, Nam-Ho; Koh, Young-Sang

    2016-01-01

    This study was intended to assess the anti-inflammatory properties of 4-hydroxy-2,3-dimethyl-2-nonen-4-olide (Comp) isolated from Ulva pertusa Kjellman on production of pro-inflammatory cytokines. Comp revealed remarkable inhibitory effects on production of pro-inflammatory cytokines in bone marrow-derived dendritic cells (BMDCs). Comp pre-treatment in the CpG DNA-stimulated BMDCs exhibited strong inhibition of interleukin (IL)-12 p40 and IL-6 production with IC50 values ranging from 7.57 ± 0.2 to 10.83 ± 0.3, respectively. It revealed an inhibitory effect on the phosphorylation of ERK1/2, JNK1/2, and p38, and on activator protein (AP)-1 reporter activity. Comp displayed noteworthy inhibitory effects on phosphorylation and degradation of IκBα, and on NF-κB reporter activity. In summary, these data propose that Comp has substantial anti-inflammatory properties and warrants further study concerning its potential use as a therapeutic agent for inflammation-associated maladies. PMID:27153074

  9. A focal adhesion kinase inhibitor 16-hydroxy-cleroda-3,13-dien-16,15-olide incorporated into enteric-coated nanoparticles for controlled anti-glioma drug delivery.

    PubMed

    Thiyagarajan, Varadharajan; Lin, Shi-Xiang; Lee, Chia-Hung; Weng, Ching-Feng

    2016-05-01

    16-Hydroxy-cleroda-3,13-dien-16,15-olide (HCD) which is extracted from a medicinal plant, Polyalthia longifolia, was shown to exhibit anticancer activity through apoptosis and FAK inhibition in our previous study. To improve its solubility and efficacy, a novel HCD delivery system using copper-substituted mesoporous silica nanoparticles (MSNs) was designed as a delivery vehicle, and the outer surfaces of MSNs were further coated with enteric polymers to prevent the drug from leaching in the stomach acid. All the data regarding synthesis and physical characterization, including Zeta potential, FT-IR spectra, N2 adsorption-desorption isotherms (BET), drug loading, powder X-ray diffraction, Thermo gravimetric analysis (TGA), Transmission electron microscopy (TEM), and Scanning electron microscopy (SEM) were well characterized. The non-coated MSN-HCD exposed to acidic pH (1.2) showed a rapid degradation of the drug, whereas the enteric-coated samples presented a sustained release profile in the gastrointestinal pHs. Cell cytotoxicity was further confirmed by the MTT-C6 Glioma cell line, in vitro. When compared with the control and pure HCD, the MSN-HCD revealed a potential anti-proliferation effect via the synergistic effect of the drug and the MSN vehicle. Additionally, this MSN-HCD had the effect of increasing the reactive oxygen species (ROS) levels and altered the Mitochondria membrane potential (MMP) in C6 cell line. The in vivo anti-tumor efficacy of enteric-coated MSN-HCD was evaluated by C6 Glioma bearing xenograft nude mice, and enteric-coated MSN-HCD clearly exhibited the greatest anti-glioma activity, as compared to the pure HCD and the untreated control. In terms of the effective treatment of brain glioma, this study provides conclusive evidence of the successful development of the anti-cancer agent HCD conjugated with enteric-coated MSN as a delivery control mechanism with enhanced dissolution characteristics. PMID:26851441

  10. The anticancer effect of (1S,2S,3E,7E,11E)-3,7,11, 15-cembratetraen-17,2-olide(LS-1) through the activation of TGF-β signaling in SNU-C5/5-FU, fluorouracil-resistant human colon cancer cells.

    PubMed

    Kim, Eun-Ji; Kang, Jung-Il; Kwak, Jeon-Won; Jeon, Chan-Hee; Tung, Nguyen-Huu; Kim, Young-Ho; Choi, Cheol-Hee; Hyun, Jin-Won; Koh, Young-Sang; Yoo, Eun-Sook; Kang, Hee-Kyoung

    2015-03-16

    The anticancer effect of (1S,2S,3E,7E,11E)-3,7,11,15-cembratetraen-17,2-olide (LS-1) from Lobophytum sp. has been already reported in HT-29 human colorectal cancer cells. In this study, we examined the effect of LS-1 on the apoptosis induction of SNU-C5/5-FU, fluorouracil-resistant human colon cancer cells. Furthermore, we investigated whether the apoptosis-induction effect of LS-1 could arise from the activation of the TGF-β pathway. In SNU-C5/5-FU treated with LS-1 of 7.1 μM (IC50), we could observe the various apoptotic characteristics, such as the increase of apoptotic bodies, the increase of the sub-G1 hypodiploid cell population, the decrease of the Bcl-2 level, the increase of procaspase-9 cleavage, the increase of procaspase-3 cleavage and the increase of poly(ADP-ribose) polymerase cleavage. Interestingly, the apoptosis-induction effect of LS-1 was also accompanied by the increase of Smad-3 phosphorylation and the downregulation of c-Myc in SNU-C5/5-FU. LS-1 also increased the nuclear localization of phospho-Smad-3 and Smad-4. We examined whether LS-1 could downregulate the expression of carcinoembryonic antigen (CEA), a direct inhibitor of TGF-β signaling. LS-1 decreased the CEA level, as well as the direct interaction between CEA and TGF-βR1 in the apoptosis-induction condition of SNU-C5/5-FU. To examine whether LS-1 can induce apoptosis via the activation of TGF-β signaling, the SNU-C5/5-FU cells were treated with LS-1 in the presence or absence of SB525334, a TGF-βRI kinase inhibitor. SB525334 inhibited the effect of LS-1 on the apoptosis induction. These findings provide evidence demonstrating that the apoptosis-induction effect of LS-1 results from the activation of the TGF-β pathway via the downregulation of CEA in SNU-C5/5-FU.

  11. 3-Oxo-18α-olean-28,13β-olide

    PubMed Central

    Santos, R. C.; Pinto, R. M. A.; Matos Beja, A.; Salvador, J. A. R.; Paixão, J. A.

    2010-01-01

    The title terpene, C30H46O3, is a 28,13β-lactone of oleanolic acid prepared with bis­muth trifluoro­methane­sulfonate (OTf), Bi(OTf)3·xH2O. All rings are trans-fused. The X-ray study shows the inversion of the orientation of 18-H in the lactonization reaction. A quantum chemical ab-initio Roothaan Hartree–Fock calculation of the equilibrium geometry of the isolated mol­ecule gives values for bond lengths and valency angles in close agreement with experimental values. The calculation also reproduces the observed mol­ecular conformation, with puckering parameters that agree well with those determined from the crystallographic study. PMID:21588427

  12. Evidence for a volatile sex pheromone in Agrilus planipennis Fairmaire (Coleoptera: Buprestidae) that synergizes attraction to a host foliar volatile

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Analysis by gas chromatography/ mass spectrometry (GC/MS) of volatiles from virgin female emerald ash borer, Agrilus planipennis Fairmaire, confirmed the emission of (3Z)-lactone [(3Z)-dodecen-12-olide] but not its geometric isomer, (3E)-lactone [(3E)-dodecen-12-olide]. Gas chromatographic/ electroa...

  13. Two new diterpenoids from Leonotis leonurus R. Br.

    PubMed

    Narukawa, Yuji; Komori, Miyuki; Niimura, Akiko; Noguchi, Hitomi; Kiuchi, Fumiyuki

    2015-01-01

    Two new diterpenoids, 14α-hydroxy-9α,13α-epoxylabd-5(6)-en-7-on-16,15-olide (1) and 13ξ-hydroxylabd-5(6),8(9)-dien-7-on-16,15-olide (2) along with six known diterpenoids were isolated from the aerial parts of Leonotis leonurus R. Br. These structures were determined on the basis of spectroscopic analyses. Some of the isolated compounds showed weak to moderate estrogen sulfotransferase inhibitory activity.

  14. Three new ursane-type triterpenoids from the aerial parts of Isodon excisoides.

    PubMed

    Jiao, Ke; Li, Huo-Yun; Zhang, Peng; Pi, Hui-Fang; Ruan, Han-Li; Wu, Ji-Zhou

    2013-09-01

    Three new ursane-type triterpenoids, 2α,3β-dihydroxy-11α,12α-epoxy-urs-28,13β-olide (1), 2α,3β,24-trihydroxy-11α,12α-epoxy-urs-28,13β-olide (2), and 2α,3α,24-trihydroxy-11,20(30)-dien-urs-28,13β-olide (6), together with six known ursane-type triterpenoids (3-5, 7-9), were isolated from the EtOAc extract of the aerial parts of Isodon excisoides. Their structures were elucidated on the basis of 1D NMR and 2D NMR analyses as well as HRMS experiments. PMID:24152070

  15. Hikiokoshins A-I, diterpenes from the leaves of Isodon japonicus.

    PubMed

    Tanaka, Naonobu; Tsuji, Eri; Sakai, Kanae; Gonoi, Tohru; Kobayashi, Jun'ichi

    2014-06-01

    Diterpenes, hikiokoshins A-I, and twelve known diterpenes were isolated from the leaves of Isodon japonicus (Burm. f.) H. Hara (Lamiaceae). The hikiokoshins A-I possess various skeletons such as ternifonane {hikiokoshin A}, ent-6,7:8,15-diseco-6,8-cyclokauran-7,20-olide {hikiokoshin B}, ent-6,7-secokauran-7,20-olide {hikiokoshin C}, and ent-7,20-epoxykaurane {hikiokoshins D-I}. Their structures were elucidated on the basis of spectroscopic analysis. Antimicrobial activities of hikiokoshins A and B were evaluated. PMID:24702849

  16. Two new triterpenoids from the resin of Styrax tonkinensis.

    PubMed

    Wang, Feng; Wang, Yi-Bo; Chen, Huan; Chen, Lei; Liang, Sheng-Wang; Wang, Shu-Mei

    2015-01-01

    Two new triterpenoids, 3β,6β-dihydroxy-12-oxo-13Hα-olean-28,19β-olide (1) and 3-oxo-olean-11,13(18)-dien-28,19β-olide (2) were isolated from the resin of Styrax tonkinensis (Pier.) Craib. The structures of both triterpenoids were determined by physicochemical and spectroscopic methods. Compound 1 is the second triterpene found with cis-fused C/D ring from the resin, which is rarely observed in oleanane-type triterpenes. PMID:25908248

  17. Triterpenoids from the roots of Actinidia chinensis.

    PubMed

    Zhou, Xue-Feng; Zhang, Peng; Pi, Hui-Fang; Zhang, Yong-Hui; Ruan, Han-Li; Wang, Hui; Wu, Ji-Zhou

    2009-08-01

    Two new triterpenoids, 1 and 2, were isolated from the hepatoprotective AcOEt fraction of the roots of Actinidia chinensis, together with eight known 12-en-28-oic acids of oleanane or ursane type, 3-10. The two new compounds were elucidated as 2alpha,3beta-dihydroxyurs-12-en-28,30-olide (1) and 2alpha,3beta,24-trihydroxyurs-12-en-28,30-olide (2), on the basis of spectroscopic (IR, NMR, and MS) analyses. The chemotaxonomic significances of some triterpenoids were also discussed.

  18. Identification of triterpenoids in chloroform extract of Agarista mexicana by MS and NMR.

    PubMed

    Pérez Gutiérrez, Rosa Martha

    2006-02-01

    Detailed structural study of the major triterpenoids from chloroform extract of Agarista mexicana revealed the presence of new pentacyclic triterpene lactone 3ss-hydroxy-ursan-28ss, 19ss-olide together with four known compounds, 12-ursene, campesterol, stigmasterol, sitosterol. These compounds were isolated by chromatography and their structures confirmed by NMR experiments and by MS.

  19. New Antiplasmodial Diterpenes from Gutierrezia sarothrae.

    PubMed

    Su, Qingxi; Dalal, Seema; Goetz, Michael; Cassera, Maria B; Kingston, David G I

    2016-06-01

    Bioassay guided fractionation of the MeOH extract of the plant Gutierrezia sarothrae (Asteraceae) using an assay for antiplasmodial activity against the drug-resistant Dd2 strain of Plasmodium falciparum led to the isolation of the two new diterpenes 3α-angeloyloxy-15-hydroxylabda-7,13-dien-16,15-olid-18-oic acid (1) and 3α-angeloyloxy-15-methoxylabda-7,13-dien-16,15-olid-18-oic acid (2). The structures of 1 and 2 were elucidated by interpretation of 1D and 2D NMR spectroscopic data, mass spectrometry, and comparison with the data of related compounds reported in the literature. Compound 1 exhibited moderate antiplasmodial activity with an IC50 values of 10.4 ± 4.3 μM. PMID:27534100

  20. Sesquiterpene lactone glucosides and alkyl glycosides from the fruit of cumin.

    PubMed

    Takayanagi, Tomomi; Ishikawa, Toru; Kitajima, Junichi

    2003-06-01

    From the polar portion of the methanolic extract of cumin (fruit of Cuminum cyminum L.), two sesquiterpenoid glucosides, cuminoside A and B, and two alkyl glycosides were isolated together with five known compounds. Their structures were established as (1S,5S,6S,10S)-10-hydroxyguaia-3,7(11)-dien-12,6-olide beta-D-glucopyranoside, (1R,5R,6S,7S,9S,10R,11R)-1,9-dihydroxyeudesm-3-en-12,6-olide 9-O-beta-D-glucopyranoside, methyl beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside and ethane-1,2-diol 1-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside, respectively.

  1. Antiproliferative Diterpenes from a Malleastrum sp. from the Madagascar dry forest.

    PubMed

    Liu, Yixi; Wiedle, C Houston; Brodie, Peggy J; Callmander, Martin W; Rakotondrajaona, R; Rakotobe, Etienne; Rasamison, Vincent E; Kingston, David G I

    2015-09-01

    An ethanol extract of leaves of the plant species Malleastrum sp. collected in northern Madagascar afforded the new clerodane diterpene 18-oxo-cleroda-3,13-dien-16,15-olide (1), together with the three known clerodane diterpenes 16,18-dihydroxykolavenic acid lactone (2), solidagolactone (3) and (-)-kolavenol (4), and the known labdane diterpene 3-oxo-ent-Iabda-8(17),13-dien-15,16-olide (5). Compounds 1, 3, and 4 showed moderate antiproliferative activities against the A2780 ovarian cancer cell line, with the IC50 values of 3.01 ± 0.8, 7.84 ± 0.2, and 17.9 ± 3 µM, respectively. The structure elucidations of all compounds were carried out based on analysis of NMR and mass spectroscopic data. The relative stereochemistry of compound 1 was determined by NOESY NMR spectrum.

  2. Guaianolide sesquiterpenes from Pulicaria crispa (Forssk.) Oliv.

    PubMed

    Stavri, Michael; Mathew, K T; Gordon, Andrew; Shnyder, Steven D; Falconer, Robert A; Gibbons, Simon

    2008-06-01

    A phytochemical study of the asteraceous herb Pulicaria crispa (Forssk.) Oliv. resulted in the characterisation of three guaianolide sesquiterpenes, 2alpha,4alpha-dihydroxy-7alphaH,8alphaH,10alphaH-guaia-1(5),11(13)-dien-8beta,12-olide (1), 1alpha,2alpha-epoxy-4beta-hydroxy-5alphaH,7alphaH,8alphaH,10alphaH-guaia-11(13)-en-8beta,12-olide (2) and 5,10-epi-2,3-dihydroaromatin (3). The structures were assigned on the basis of extensive 1 and 2D NMR experiments. Compound 3 exhibited weak antimycobacterial activity against Mycobacterium phlei with a minimum inhibitory concentration of 0.52 mM and cytotoxicity (IC50 of 5.8+/-0.2 microM) in a human bladder carcinoma cell line, EJ-138.

  3. Two new triterpenoids from fruiting bodies of fungus Ganoderma lucidum.

    PubMed

    Zhao, Zhen-Zhu; Yin, Rong-Hua; Chen, He-Ping; Feng, Tao; Li, Zheng-Hui; Dong, Ze-Jun; Cui, Bao-Kai; Liu, Ji-Kai

    2015-01-01

    Two new triterpenoids, (24E)-9α,11α-epoxy-3β-hydroxylanosta-7,24-dien-26-al (1) and (22Z,24Z)-13-hydroxy-3-oxo-14(13 → 12)abeo-lanosta-8,22,24-trien-26,23-olide (2) were isolated from dried fruiting bodies of fungus Ganoderma lucidum. The structures of these two new compounds were elucidated on the basis of extensive spectroscopic analyses. Compound 1 possessed a lanostane skeleton, while compound 2 was based on a rare 14 (13 → 12)abeo-lanostane skeleton with a 26,23-olide moiety. Both of them were evaluated for their antifungal and cytotoxic activities. Neither of them displayed obvious inhibition on Candida albicans and five human cancer cell lines.

  4. Purification and characterization of 4-methylmuconolactone methylisomerase, a novel enzyme of the modified 3-oxoadipate pathway in the gram-negative bacterium Alcaligenes eutrophus JMP 134.

    PubMed Central

    Pieper, D H; Stadler-Fritzsche, K; Knackmuss, H J; Engesser, K H; Bruce, N C; Cain, R B

    1990-01-01

    4-Carboxymethyl-4-methylbut-2-en-4-olide (4-methyl-2-enelactone) isomerase, transforming 4-methyl-2-enelactone to 3-methyl-2-enelactone, was purified from a derivative strain of Pseudomonas sp. B13, named B13 FR1, carrying the plasmid pFRC2OP. This plasmid contained the isomerase gene cloned from Alcaligenes eutrophus JMP 134, which uses 4-methyl-2-enelactone as a carbon source. The enzyme consists of a single peptide chain of Mr 40,000 as judged by SDS/PAGE. In addition to 4-methyl-2-enelactone, the putative reaction intermediate, 1-methyl-3,7-dioxo-2,6-dioxy-bicyclo[3.3.0]octane (1-methylbislactone), was a substrate for the enzyme, but kinetic data presented did not favour its role as a reaction intermediate. Isomeric methyl-substituted 4-carboxymethylbut-2-en-4-olides were neither substrates nor inhibitors. Possible reaction mechanisms are discussed. PMID:2241929

  5. Aliphatic and eudesmalolide esters extracted from the roots of Inula racemosa Hook

    PubMed Central

    Khan, Maria; Mir, S.R.; Ali, Abuzar; Yusuf, Mohammad; Ali, Mohammed

    2014-01-01

    Background: Phytochemical investigation of hydroalcoholic extract of the root of Inula racemosa Hook. Materials and Methods: Open silica gel column chromatographic techniques with different solvent systems was used for isolation of aliphatic and eudesmalolide esters from hydroalcoholic extract of the root of Inula racemosa. The structure elucidation of the compounds was done on the basis of spectral data analysis, chemical reactions and comparision with literature data. Results: Phytochemical investigation of the hydroalcoholic extract of the root of Inula racemosa Hook. f. led to the isolation of (5z, 13z)-n-decanyl-n-docos-5, 13-dienoate, a new fatty acid ester, two new sesquiterpenic ester identified as 15-[(13z, 18′z, 20′z)-n-tricos-13, 18, 20-trienyl]-eudesmal-4 (11), 6, 12 (13)-trien-8,14-olide-15-oate and 15- [(16′z), (21′z)-n- tetracos-16′, 21′- dienyl]-eudesmal-4 (11) 6, 12 (13)-trien-8, 14-olide-15-oate, two new eudesmanolide ester i.e. 15-[(16z)-n-monadec-16′- enyl]-eudesmal-4 (11) 6, 12 (13)-trien-8,14-olide-15-oate and 15-[(16′z)-n-tetracos-16′- enyl]-endesmal-4 (11), 6, 12 (13)-trien-8,14-olide-15-oate along with the known compound n-Hexadecanyl n-docosanoate. Conclusion: Five new phytoconstituents were identified along with one known compound as aliphatic and eudesmalolide esters from the hydroalcoholic extract of the root of Inula racemosa, as mentioned above. PMID:24695458

  6. Phytochemical investigation of the seeds of Althea officinalis L.

    PubMed

    Rani, Sunita; Khan, Suroor A; Ali, M

    2010-09-01

    Phytochemical investigation of the seeds of Althea officinalis L. (Malvaceae) led to the isolation of three new phytoconstituents, identified as n-hexacos-2-enyl-1,5-olide (altheahexacosanyl lactone), 2beta-hydroxycalamene (altheacalamene) and 5,6-dihydroxycoumarin-5-dodecanoate-6beta-D-glucopyranoside (altheacoumarin glucoside), along with the known phytoconstituents lauric acid, beta-sitosterol and lanosterol. The structures of these compounds were established on the basis of spectral analysis and chemical reactions.

  7. New triterpenoids of mallotus repandus

    PubMed

    Huang; Wang; Lin

    1999-06-01

    Three new triterpenoids-3alpha-hydroxy-13alpha-ursan-28,12beta-olide 3-benzoate (1), 3alpha-hydroxy-28beta-methoxy-13alpha-ursan-28, 12beta-epoxide 3-benzoate (2), and 3alpha-hydroxy-13alpha-ursan-28-oic acid (3)-and four known compounds were isolated from the stem and root bark of Mallotus repandus.

  8. Reversible optical control of cyanine fluorescence in fixed and living cells: optical lock-in detection immunofluorescence imaging microscopy

    PubMed Central

    Yan, Yuling; Petchprayoon, Chutima; Mao, Shu; Marriott, Gerard

    2013-01-01

    Optical switch probes undergo rapid and reversible transitions between two distinct states, one of which may fluoresce. This class of probe is used in various super-resolution imaging techniques and in the high-contrast imaging technique of optical lock-in detection (OLID) microscopy. Here, we introduce optimized optical switches for studies in living cells under standard conditions of cell culture. In particular, a highly fluorescent cyanine probe (Cy or Cy3) is directly or indirectly linked to naphthoxazine (NISO), a highly efficient optical switch that undergoes robust, 405/532 nm-driven transitions between a colourless spiro (SP) state and a colourful merocyanine (MC) state. The intensity of Cy fluorescence in these Cy/Cy3-NISO probes is reversibly modulated between a low and high value in SP and MC states, respectively, as a result of Förster resonance energy transfer. Cy/Cy3-NISO probes are targeted to specific proteins in living cells where defined waveforms of Cy3 fluorescence are generated by optical switching of the SP and MC states. Finally, we introduce a new imaging technique (called OLID-immunofluorescence microscopy) that combines optical modulation of Cy3 fluorescence from Cy3/NISO co-labelled antibodies within fixed cells and OLID analysis to significantly improve image contrast in samples having high background or rare antigens. PMID:23267183

  9. The chafer pheromone buibuilactone and ant pyrazines are also produced by marine bacteria.

    PubMed

    Dickschat, Jeroen S; Wagner-Döbler, Irene; Schulz, Stefan

    2005-04-01

    Headspace extracts obtained from agar plate cultures of two marine bacteria from the North Sea (Germany), Loktanella strain BIO-204 and Dinoroseobacter shibae strain DFL-27, were analyzed by GC-MS. Several gamma-lactones and one delta-lactone were identified, besides pyrazines and some sulfur compounds. The absolute configuration of the major lactone (R,Z)-dodec-5-en-4-olide, known as buibuilactone, a pheromone of several scarab beetles, was determined by a new catalytic enantioselective synthesis and GC on a chiral stationary phase. Unsaturated lactones in the extracts included (E)-dodec-5-en-4-olide and the regioisomer (Z)-dodec-6-en-4-olide, previously identified as a component of black-tailed deer urine. The pyrazines 2-butyl-3,6-dimethylpyrazine and 2-isopentyl-3,6-dimethylpyrazine were identified by comparison with synthesized material. The latter compound is a known ant pheromone, as is another identified pyrazine, 2-ethyl-3,6-dimethylpyrazine. The striking similarity between insect pheromones and these bacterial volatiles is discussed, suggesting the possibility of more widespread occurrence of symbiosis between microorganisms and insects than previously thought. PMID:16124260

  10. Cytotoxic and antibacterial cembranoids from a South China Sea soft coral, Lobophytum sp.

    PubMed

    Zhao, Min; Yin, Jian; Jiang, Wei; Ma, Minshan; Lei, Xinxiang; Xiang, Zheng; Dong, Jianyong; Huang, Kexin; Yan, Pengcheng

    2013-04-01

    Chemical examination of a South China Sea soft coral Lobophytum sp. led to the isolation of three new α-methylene-γ-lactone-containing cembranoids, (1R*,3R*, 4R*,14R*,7E,11E)-3,4-epoxycembra-7,11,15(17)-trien-16,14-olide (1), (1R*,7S*,14S*,3E, 11E)-7-hydroperoxycembra-3,8(19),11,15(17)-tetraen-16,14-olide (2), and (1R*,7S*,14S*, 3E,11E)-18-acetoxy-7-hydroperoxycembra-3,8(19),11,15(17)-tetraen-16,14-olide (3), along with eleven known analogues 4-14. The structures of the new compounds were elucidated through extensive spectroscopic analysis, including 1D and 2D NMR data. Compounds 1-3 exhibited moderate cytotoxic activity against the selected tumor cell lines. Moreover, 2 and 3 were found to be moderate inhibitors against the bacteria S. aureus and S. pneumoniae.

  11. A Biologically Active Analog of the Sex Pheromone of the Emerald Ash Borer, Agrilus planipennis.

    PubMed

    Silk, P J; Ryall, K; Mayo, P; MaGee, D I; Leclair, G; Fidgen, J; Lavallee, R; Price, J; McConaghy, J

    2015-03-01

    The emerald ash borer, Agrilus planipennis (Coleoptera: Buprestidae) (EAB), is an invasive species causing unprecedented levels of mortality to ash trees in its introduced range. The female-produced sex pheromone of EAB has been shown to contain the macrocyclic lactone (3Z)-dodecen-12-olide. This compound and its geometrical isomer, (3E)-dodecen-12-olide, have been demonstrated previously to be EAG active and, in combination with a host-derived green leaf volatile, (3Z)-hexenol, to be attractive to male EAB in green prism traps deployed in the ash tree canopy. In the current study, we show that the saturated analog, dodecan-12-olide, is similarly active, eliciting an antennal response and significant attraction of EAB in both olfactometer and trapping bioassays in green traps with (3Z)-hexenol. Conformational modeling of the three lactones reveals that their energies and shapes are very similar, suggesting they might share a common receptor in EAB antennae. These findings provide new insight into the pheromone ecology of this species, highlighting the apparent plasticity in response of adults to the pheromone and its analog. Both of the unsaturated isomers are costly to synthesize, involving multistep, low-yielding processes. The saturated analog can be made cheaply, in high yield, and on large scale via Mitsunobu esterification of a saturated ω-hydroxy acid or more simply by Baeyer-Villiger oxidation of commercially available cyclododecanone. The analog can thus provide an inexpensive option as a lure for detection surveys as well as for possible mitigation purposes, such as mating disruption. PMID:25786893

  12. Metabolomic Profiling and Genomic Study of a Marine Sponge-Associated Streptomyces sp

    PubMed Central

    Viegelmann, Christina; Margassery, Lekha Menon; Kennedy, Jonathan; Zhang, Tong; O’Brien, Ciarán; O’Gara, Fergal; Morrissey, John P.; Dobson, Alan D. W.; Edrada-Ebel, RuAngelie

    2014-01-01

    Metabolomics and genomics are two complementary platforms for analyzing an organism as they provide information on the phenotype and genotype, respectively. These two techniques were applied in the dereplication and identification of bioactive compounds from a Streptomyces sp. (SM8) isolated from the sponge Haliclona simulans from Irish waters. Streptomyces strain SM8 extracts showed antibacterial and antifungal activity. NMR analysis of the active fractions proved that hydroxylated saturated fatty acids were the major components present in the antibacterial fractions. Antimycin compounds were initially putatively identified in the antifungal fractions using LC-Orbitrap. Their presence was later confirmed by comparison to a standard. Genomic analysis of Streptomyces sp. SM8 revealed the presence of multiple secondary metabolism gene clusters, including a gene cluster for the biosynthesis of the antifungal antimycin family of compounds. The antimycin gene cluster of Streptomyces sp. SM8 was inactivated by disruption of the antimycin biosynthesis gene antC. Extracts from this mutant strain showed loss of antimycin production and significantly less antifungal activity than the wild-type strain. Three butenolides, 4,10-dihydroxy-10-methyl-dodec-2-en-1,4-olide (1), 4,11-dihydroxy-10-methyl-dodec-2-en-1,4-olide (2), and 4-hydroxy-10-methyl-11-oxo-dodec-2-en-1,4-olide (3) that had previously been reported from marine Streptomyces species were also isolated from SM8. Comparison of the extracts of Streptomyces strain SM8 and its host sponge, H. simulans, using LC-Orbitrap revealed the presence of metabolites common to both extracts, providing direct evidence linking sponge metabolites to a specific microbial symbiont. PMID:24893324

  13. Metabolomic profiling and genomic study of a marine sponge-associated Streptomyces sp.

    PubMed

    Viegelmann, Christina; Margassery, Lekha Menon; Kennedy, Jonathan; Zhang, Tong; O'Brien, Ciarán; O'Gara, Fergal; Morrissey, John P; Dobson, Alan D W; Edrada-Ebel, RuAngelie

    2014-06-01

    Metabolomics and genomics are two complementary platforms for analyzing an organism as they provide information on the phenotype and genotype, respectively. These two techniques were applied in the dereplication and identification of bioactive compounds from a Streptomyces sp. (SM8) isolated from the sponge Haliclona simulans from Irish waters. Streptomyces strain SM8 extracts showed antibacterial and antifungal activity. NMR analysis of the active fractions proved that hydroxylated saturated fatty acids were the major components present in the antibacterial fractions. Antimycin compounds were initially putatively identified in the antifungal fractions using LC-Orbitrap. Their presence was later confirmed by comparison to a standard. Genomic analysis of Streptomyces sp. SM8 revealed the presence of multiple secondary metabolism gene clusters, including a gene cluster for the biosynthesis of the antifungal antimycin family of compounds. The antimycin gene cluster of Streptomyces sp. SM8 was inactivated by disruption of the antimycin biosynthesis gene antC. Extracts from this mutant strain showed loss of antimycin production and significantly less antifungal activity than the wild-type strain. Three butenolides, 4,10-dihydroxy-10-methyl-dodec-2-en-1,4-olide (1), 4,11-dihydroxy-10-methyl-dodec-2-en-1,4-olide (2), and 4-hydroxy-10-methyl-11-oxo-dodec-2-en-1,4-olide (3) that had previously been reported from marine Streptomyces species were also isolated from SM8. Comparison of the extracts of Streptomyces strain SM8 and its host sponge, H. simulans, using LC-Orbitrap revealed the presence of metabolites common to both extracts, providing direct evidence linking sponge metabolites to a specific microbial symbiont. PMID:24893324

  14. A Biologically Active Analog of the Sex Pheromone of the Emerald Ash Borer, Agrilus planipennis.

    PubMed

    Silk, P J; Ryall, K; Mayo, P; MaGee, D I; Leclair, G; Fidgen, J; Lavallee, R; Price, J; McConaghy, J

    2015-03-01

    The emerald ash borer, Agrilus planipennis (Coleoptera: Buprestidae) (EAB), is an invasive species causing unprecedented levels of mortality to ash trees in its introduced range. The female-produced sex pheromone of EAB has been shown to contain the macrocyclic lactone (3Z)-dodecen-12-olide. This compound and its geometrical isomer, (3E)-dodecen-12-olide, have been demonstrated previously to be EAG active and, in combination with a host-derived green leaf volatile, (3Z)-hexenol, to be attractive to male EAB in green prism traps deployed in the ash tree canopy. In the current study, we show that the saturated analog, dodecan-12-olide, is similarly active, eliciting an antennal response and significant attraction of EAB in both olfactometer and trapping bioassays in green traps with (3Z)-hexenol. Conformational modeling of the three lactones reveals that their energies and shapes are very similar, suggesting they might share a common receptor in EAB antennae. These findings provide new insight into the pheromone ecology of this species, highlighting the apparent plasticity in response of adults to the pheromone and its analog. Both of the unsaturated isomers are costly to synthesize, involving multistep, low-yielding processes. The saturated analog can be made cheaply, in high yield, and on large scale via Mitsunobu esterification of a saturated ω-hydroxy acid or more simply by Baeyer-Villiger oxidation of commercially available cyclododecanone. The analog can thus provide an inexpensive option as a lure for detection surveys as well as for possible mitigation purposes, such as mating disruption.

  15. Identification of a Grain Beetle Macrolide Pheromone and Its Synthesis by Ring-Closing Metathesis Using a Terminal Alkyne.

    PubMed

    Hötling, Susann; Bittner, Celine; Tamm, Matthias; Dähn, Sonja; Collatz, Jana; Steidle, Johannes L M; Schulz, Stefan

    2015-10-16

    A major C18-macrolide was found during analysis of the frass of the storage beetle Oryzaephilus surinamensis to be (9Z,12Z,15R)-octadeca-9,12-dien-15-olide (10, cucujolide XI). The synthesis used ring-closing alkyne metathesis as a key step. The highly active 2,4,6-trimethylbenzylidyne molybdenum complex [MesCMo{OC(CF3)2Me}3] (12) allowed the use of a terminal alkyne and afforded the product in excellent yield. Bioassays proved the activity of the R-enantiomer 10 in the aggregation of the beetle. Cucujolide XI is the first macrolide pheromone oxidized at the ω-4 position.

  16. Inhibition effects of isolated compounds from Artemisia rubripes Nakai of the classical pathway on the complement system.

    PubMed

    Jung, Seil; Lee, Jai-Heon; Lee, Young-Choon; Moon, Hyung-In

    2012-04-01

    The study evaluated the anticomplement activity from isolated compounds from Artemisia rubripes Nakai from South Korea on the classical pathway. In the previous works, Artemisia rubripes chloroform extracts showed inhibitory activity against complement system. The chromatographic separation of a chloroform chloride extract of Artemisia rubripes led to the isolation of three compounds. Their structures were characterized to be scopoletin (1), 11,(13)-triene-6,12-olide (2), and 1β,6α-dihydroxy-4(15)-eudesmene (3) by spectroscopic data. This is the first report of anticomplement activity of isolated compounds from Artemisia rubripes.

  17. Saponins from the roots of Zygophyllum gaetulum and their effects on electrically-stimulated guinea-pig ileum.

    PubMed

    Aquino, R; Tortora, S; Fkih-Tetouani, S; Capasso, A

    2001-02-01

    A new ursanolide, 3beta-O-alpha-L-rhamnopyranosyl-(1->2)-O-alpha-L-arabinopyranosyl-(1->2)-beta-D-glucopyranosyl)oxy]-ursan-20beta,28-olide, zygophyloside N (1), and three known quinovic acid glycosides were isolated from the methanolic extract of the roots of Zygophyllum gaetulum. The crude extract, some fractions and 3-O-beta-D-glucopyranosyl quinovic acid 28-beta-D-glucopyranosyl ester, significantly and dose-dependently, are able to reduce the electrically-induced contractions of isolated guinea-pig ileum. The structure of compound (1) was determined, using 1D and 2D NMR techniques.

  18. Cucurbitane-type triterpenoids from the fruit pulp of Momordica charantia.

    PubMed

    Liao, Yun-Wen; Chen, Chiy-Rong; Kuo, Yueh-Hsiung; Hsu, Jue-Liang; Shih, Wen-Ling; Cheng, Hsueh-Ling; Huang, Tzou-Chi; Chang, Chi-I

    2012-12-01

    Three new cucurbitane-type triterpenoids, 5beta,19-epoxy-23(R)-methoxycucurbita-6,24-dien-3beta-ol (1), 5beta,19-epoxy-23(S)-methoxycucurbita-6,24-dien-3beta-ol (2), and 3beta-hydroxy-23(R)-methoxycucurbita-6,24-dien-5beta,19-olide (3), were isolated from the fruit pulp of Momordica charantia. Their structures were established on the basis of extensive NMR (1H, 13C, COSY, HMQC, HMBC, and NOESY) and EI-MS studies. Compound 1 exhibited cytotoxic activity against the SK-Hep 1 cell line.

  19. Antennally active macrolide from the emerald ash borer Agrilus planipennis emitted predominantly by females.

    PubMed

    Bartelt, Robert J; Cossé, Allard A; Zilkowski, Bruce W; Fraser, Ivich

    2007-07-01

    The macrocyclic lactone (3Z)-dodecen-12-olide was identified from the emissions of the emerald ash borer, Agrilus planipennis, feeding on ash foliage. The compound was detected from both sexes but was ca. 10 times more abundant from females. It was readily sensed by antennae of both males and females. Identification was confirmed by synthesis. The behavioral effects of the lactone remain unstudied in A. planipennis, but a verified pheromonal function could lead to improved monitoring for this invasive pest. The lactone is part of the pheromone of Cryptolestes pusillus, an unrelated beetle species.

  20. A new labdane diterpene from the rhizomes of Alpinia officinarum.

    PubMed

    Zou, Qiong-Yu; Wu, Hai-Feng; Tang, Yu-Lian; Chen, Di-Zhao

    2016-01-01

    A new labdane diterpene, (Z)-12,14-labdadien-15(16)-olide-17-oic acid (1), and a new natural cadinane sesquiterpene, 4-isopropyl-6-methyl-1-naphthalenemethanol (2), were isolated from the ethanolic extract of the rhizomes of Alpinia officinarum, together with three other products, galangin (3), kaempferol (4) and quercetin (5). Their structures were elucidated by using extensive spectroscopic methods. Compounds 1 and 2 showed no remarkable cytotoxic activity against HeLa and HepG2 cancer cell lines with IC50>50 μg mL(- 1).

  1. Alkaloids and sesquiterpenes from the South China Sea gorgonian Echinogorgia pseudossapo.

    PubMed

    Gao, Cheng-Hai; Wang, Yi-Fei; Li, Shen; Qian, Pei-Yuan; Qi, Shu-Hua

    2011-01-01

    Five zoanthoxanthin alkaloids (1-5) and four sesquiterpenes (6-9) were isolated from the South China Sea gorgonian Echinogorgia pseudossapo. Their structures were determined on the bases of extensive spectroscopic analyses, including 1D and 2D NMR data. Among them, pseudozoanthoxanthins III and IV (1-2), 8-hydroxy-6β-methoxy-14- oxooplop-6,12-olide (6) and 3β-methoxyguaian-10(14)-en-2β-ol (7) were new, 1 and 3 showed mild anti-HSV-1 activity, and 7 showed significant antilarval activity towards Balanus amphitrite larvae.

  2. Ursane-type nortriterpenes with a five-membered A-ring from Rubus innominatus.

    PubMed

    Chen, Zhenzhong; Tong, Ling; Feng, Yuanli; Wu, Jizhou; Zhao, Xiaoya; Ruan, Hanli; Pi, Huifang; Zhang, Peng

    2015-08-01

    Two nortriterpenes (rubuminatus A and B), which contain a distinctive contracted a five-membered A-ring ursane-type skeleton, and six triterpenes along with 17 known triterpenes were isolated from the roots of Rubus innominatus S. Moore. These structures were determined to be 19α-hydroxy-2-oxo-nor- A(3)-urs-12-en-28-oic acid, 1β,19α-dihydroxy-2-oxo-nor-A(3)-urs-12-en-28-oic acid, 1β,2α,3α,19α-tetrahy droxyurs-12-en-23-formyl-28-oic acid, 1β,2α,3α,19α,23- pentahydroxyurs-11-en-28-oic acid, 1-oxo-siaresinolic acid, 2α,3α-dihydroxyolean-11,13(18)-dien-19β,28-olide, 1β,2α,3α-trihydroxy-19-oxo- 18,19-seco-urs-11,13(18)-dien-28-oic acid, and 2-O-benzoyl alphitolic acid based on extensive spectroscopic analyses. In vitro anti-inflammatory abilities to modulate the production of TNF-α, IL-1β, and IL-6 in LPS-induced RAW 264.7 macrophages of the compounds were determined. Rubuminatus A and B, as well as 1-oxo-siaresinolic acid and 2α,3α-dihydroxyolean-11,13(18)-dien-19β,28-olide, exhibited significant inhibitory effects on these cytokines.

  3. Combination of chromatographic and spectroscopic methods for the isolation and characterization of polar guaianolides from Achillea asiatica.

    PubMed

    Glasl, S; Gunbilig, D; Narantuya, S; Werner, I; Jurenitsch, J

    2001-11-30

    Four polar guaianolides, 8alpha-angeloxy-2alpha,4alpha, 10beta-trihydroxy-6betaH,7alphaH, 11betaH-1(5)-guaien- 12,6alpha-olide; 8alpha-angeloxy-1beta,2beta:4beta,5beta-diepoxy- 10beta-hydroxy-6betaH,7alphaH,11betaH-12,6alpha-guaianolide; 8alpha-angeloxy-4alpha, 10beta-dihydroxy-2-oxo-6betaH, 7alphaH, 11betaH- 1(5)-guaien- 12,6alpha-olide and 8-desacetyl-matricarin, were isolated from Achillea asiatica and characterized by TLC, MS, IR, HPLC and diode array detection. Purified extracts were separated by means of flash chromatography. HPLC separations were achieved using different methanol-water gradients as mobile phase and LiChrospher 100-RP8 5 microm or Zorbax SB-C8 3.5 microm as stationary phases. The chromatographical data are compared to those of the proazulene 8alpha-tigloxy-artabsin which shows antiinflammatory effects. By means of these characteristics the identification of the guaianolides with potential antiphlogistic properties is also possible from other sources.

  4. Highly hydroxylated guaianolides of Achillea asiatica and Middle European Achillea species.

    PubMed

    Glasl, S; Presser, A; Gunbilig, D; Werner, I; Narantuya, S; Haslinger, E; Jurenitsch, J; Kubelka, W

    2001-12-01

    From flower heads of Achillea asiatica (L.) Serg., three new guaianolides were isolated by repeated column chromatography and HPLC. The constitution and the stereochemistry of these new, labile compounds were determined by MS, one ((1)H, (13)C, selective (1)H-TOCSY and (1)H-NOESY) and two-dimensional NMR experiments ((1)H, (1)H-COSY, (1)H, (13)C-HSQC, (1)H, (13)C-HMBC). The substances were identified as 8 alpha-angeloxy-2 alpha, 4 alpha,10 beta-trihydroxy-6 beta H,7 alpha H, 11 beta H-1(5)-guaien-12,6 alpha-olide (1), 8 alpha-angeloxy-1 beta,2 beta:4 beta,5 beta-diepoxy-10 beta-hydroxy-6 beta H, 7 alpha H, 11 beta H-12,6 alpha-guaianolide (2) and 8 alpha-angeloxy-4 alpha,10 beta-dihydroxy-2-oxo-6 beta H,7 alpha H, 11 beta H-1(5)-guaien-12,6 alpha-olide (3). They were also detected in Middle European species (Achillea collina, Achillea ceretanica (2x and 4x), Achillea roseoalba, Achillea asplenifolia) by HPLC, TLC and off line MS and have not been described before. The possibility that these compounds might be products of an oxidation process is discussed.

  5. Alcohol absorption inhibitors from bay leaf (Laurus nobilis): structure-requirements of sesquiterpenes for the activity.

    PubMed

    Yoshikawa, M; Shimoda, H; Uemura, T; Morikawa, T; Kawahara, Y; Matsuda, H

    2000-08-01

    Through a bioassay-guided separation using inhibitory activity on blood ethanol elevation in oral ethanol-loaded rat, various sesquiterpenes having an alpha-methylene-gamma-butyrolactone moiety, costunolide (1), dehydrocostus lactone (2), zaluzanin D (3), reynosin (4), santamarine (5), 3alpha-acetoxyeudesma-1,4(15),11(13)-trien-12,6alpha-+ ++olide (6) and 3-oxoeudesma-1,4,11(13)-trien-12,6alpha-olide (7), were isolated as the active principle from the leaves of Laurus nobilis (bay leaf, laurel). In order to characterize the structure requirement for the activity, several reduction products (2a-2d) and amino acid adducts (2e, 2f) of the alpha-methylene-gamma-butyrolactone moiety were synthesized from 2 and the inhibitory activities of these sesquiterpenes, together with alpha-methylene-gamma-butyrolactone (12) and its related compounds (13-16), were examined. These results indicated that the gamma-butyrolactone or gamma-butyrolactol moiety having alpha-methylene or alpha-methyl group was essential for the inhibitory activity on ethanol absorption. Since 1, 2 and 12 showed no significant effect on glucose absorption, these sesquiterpenes appeared to selectively inhibit ethanol absorption. In addition, the acute toxicities of 1 and 2 in a single oral administration were found to be lower than that of 12.

  6. Diterpenoids and triterpenoids from Euphorbia guyoniana.

    PubMed

    Haba, Hamada; Lavaud, Catherine; Harkat, Hassina; Alabdul Magid, Abdulmagid; Marcourt, Laurence; Benkhaled, Mohammed

    2007-05-01

    Two new compounds with tigliane and cycloartane skeletons: 4,12-dideoxy(4alpha)phorbol-13-hexadecanoate (1) and 24-methylenecycloartane-3,28-diol (2), respectively, in addition of four known diterpenoids and 13 triterpenoids: 3-benzoyloxy-5,15-diacetoxy-9,14-dioxojatropha-6(17),11-diene (4), ent-abieta-8(14),13(15)-dien-16,12-olide (5), ent-8alpha,14alpha-epoxyabieta-11,13(15)-dien-16,12-olide (6), ent-3-hydroxyatis-16(17)-ene-2,14-dione (7), 3beta-hydroxytaraxer-14-en-28-oic acid (8), beta-sitosteryl-3beta-glucopyranoside-6'-O-palmitate (9), multiflorenyl acetate (10), multiflorenyl palmitate (11), peplusol (12), 24-methylenecycloartanol (3), lanosterol (13), euferol (14), butyrospermol (15), cycloartenol (16), obtusifoliol (17), cycloeucalenol (18) and beta-sitosterol (19), were isolated from the roots of Euphorbia guyoniana. Their structures were established on the basis of physical and spectroscopic analysis, including 1D and 2D homo- and heteronuclear NMR experiments (COSY, HSQC, HMBC and NOESY) and by comparison with the literature data.

  7. Ursane-type nortriterpenes with a five-membered A-ring from Rubus innominatus.

    PubMed

    Chen, Zhenzhong; Tong, Ling; Feng, Yuanli; Wu, Jizhou; Zhao, Xiaoya; Ruan, Hanli; Pi, Huifang; Zhang, Peng

    2015-08-01

    Two nortriterpenes (rubuminatus A and B), which contain a distinctive contracted a five-membered A-ring ursane-type skeleton, and six triterpenes along with 17 known triterpenes were isolated from the roots of Rubus innominatus S. Moore. These structures were determined to be 19α-hydroxy-2-oxo-nor- A(3)-urs-12-en-28-oic acid, 1β,19α-dihydroxy-2-oxo-nor-A(3)-urs-12-en-28-oic acid, 1β,2α,3α,19α-tetrahy droxyurs-12-en-23-formyl-28-oic acid, 1β,2α,3α,19α,23- pentahydroxyurs-11-en-28-oic acid, 1-oxo-siaresinolic acid, 2α,3α-dihydroxyolean-11,13(18)-dien-19β,28-olide, 1β,2α,3α-trihydroxy-19-oxo- 18,19-seco-urs-11,13(18)-dien-28-oic acid, and 2-O-benzoyl alphitolic acid based on extensive spectroscopic analyses. In vitro anti-inflammatory abilities to modulate the production of TNF-α, IL-1β, and IL-6 in LPS-induced RAW 264.7 macrophages of the compounds were determined. Rubuminatus A and B, as well as 1-oxo-siaresinolic acid and 2α,3α-dihydroxyolean-11,13(18)-dien-19β,28-olide, exhibited significant inhibitory effects on these cytokines. PMID:25944373

  8. Cytotoxic sesquiterpene lactones from the aerial parts of Inula aucheriana.

    PubMed

    Gohari, Ahmad Reza; Mosaddegh, Mahmoud; Naghibi, Farzaneh; Eslami-Tehrani, Bahara; Pirani, Atefeh; Hamzeloo-Moghadam, Maryam; Read, Roger W

    2015-01-01

    Inula aucheriana DC is a member of the family Asteraceae which is known to produce cytotoxic secondary metabolites noted as sesquiterpene lactones. In the present study, sesquiterpene lactones inuchinenolide B, 6-deoxychamissonolide (stevin) and 14-acetoxy-1β,5α,7αH-4β-hydroxy-guai-9(10),11(13)-dien-12,8α-olide were isolated from I. aucheriana. Inuchinenolide B and 14-acetoxy-1β,5α,7αH-4β-hydroxy-guai-9(10),11(13)-dien-12,8α-olide were further evaluated by the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) assay to demonstrate cytotoxic activity with IC50 values of (56.6, 19.0), (39.0, 11.8), and (55.7, 15.3) μg/mL against HepG-2, MCF-7 and A-549 cells, respectively. The cytotoxic activity of the two evaluated sesquiterpene lactones partly explains the cytotoxic activity that was previously observed for the extracts of Inula aucheriana. The isolated compounds could be further investigated in cancer research studies.

  9. Degradation of toluene by ortho cleavage enzymes in Burkholderia fungorum FLU100

    PubMed Central

    Dobslaw, Daniel; Engesser, Karl-Heinrich

    2015-01-01

    Burkholderia fungorum FLU100 simultaneously oxidized any mixture of toluene, benzene and mono-halogen benzenes to (3-substituted) catechols with a selectivity of nearly 100%. Further metabolism occurred via enzymes of ortho cleavage pathways with complete mineralization. During the transformation of 3-methylcatechol, 4-carboxymethyl-2-methylbut-2-en-4-olide (2-methyl-2-enelactone, 2-ML) accumulated transiently, being further mineralized only after a lag phase of 2 h in case of cells pre-grown on benzene or mono-halogen benzenes. No lag phase, however, occurred after growth on toluene. Cultures inhibited by chloramphenicol after growth on benzene or mono-halogen benzenes were unable to metabolize 2-ML supplied externally, even after prolonged incubation. A control culture grown with toluene did not show any lag phase and used 2-ML as a substrate. This means that 2-ML is an intermediate of toluene degradation and converted by specific enzymes. The conversion of 4-methylcatechol as a very minor by-product of toluene degradation in strain FLU100 resulted in the accumulation of 4-carboxymethyl-4-methylbut-2-en-4-olide (4-methyl-2-enelactone, 4-ML) as a dead-end product, excluding its nature as a possible intermediate. Thus, 3-methylcyclohexa-3,5-diene-1,2-diol, 3-methylcatechol, 2-methyl muconate and 2-ML were identified as central intermediates of productive ortho cleavage pathways for toluene metabolism in B. fungorum FLU100. PMID:25130674

  10. Alkylphloroglucinol derivatives and triterpenoids with soluble epoxide hydrolase inhibitory activity from Callistemon citrinus.

    PubMed

    Khanh, Pham Ngoc; Duc, Ho Viet; Huong, Tran Thu; Son, Ninh The; Ha, Vu Thi; Van, Doan Thi; Tai, Bui Huu; Kim, Ji Eun; Jo, Ah Reum; Kim, Young Ho; Cuong, Nguyen Manh

    2016-03-01

    Phytochemical analysis of the leaves and stems of Callistemon citrinus (Curtis) Skeels led to the isolation of two new alkylphloroglucinols, gallomyrtucommulone E and F (1 and 2), along with four other known alkylphloroglucinol derivatives, gallomyrtucommulone A (3), endoperoxide G3 (4), myrtucommulone B (5), callistenone B (6) and five known triterpenoids, including betulinic acid (7), 3β-acetylmorolic acid (8), 3β-hydroxy-urs-11-en-13(28)-olide (9), diospyrolide (10) and ursolic acid (11). The structures of the natural compounds were determined from the spectroscopic evidences including 1D-/2D-NMR and HR-MS spectrometry. All the isolated compounds were assessed for the effects on the sEH inhibitory activity. The acylphloroglucinols myrtucommulone B (5)/callistenone B (6) (in mixture), and two triterpenoids, ursolic acid (11) and 3β-hydroxy-urs-11-en-13(28)-olide (9) displayed strong inhibition of sEH activity, with IC50 values of 0.7, 11.2 and 24.8 μM, respectively. PMID:26548595

  11. Antiproliferative Scalarane-Based Metabolites from the Red Sea Sponge Hyrtios erectus.

    PubMed

    Elhady, Sameh S; Al-Abd, Ahmed M; El-Halawany, Ali M; Alahdal, Abdulrahman M; Hassanean, Hashim A; Ahmed, Safwat A

    2016-01-01

    Two new sesterterpenes analogs, namely, 12-acetoxy,16-epi-hyrtiolide (1) and 12β-acetoxy,16β-methoxy,20α-hydroxy-17-scalaren-19,20-olide (2), containing a scalarane-based framework along with seven previously reported scalarane-type sesterterpenes (3-9) have been isolated from the sponge Hyrtios erectus (order Dictyoceratida) collected from the Red Sea, Egypt. The structures of the isolated compounds were elucidated on the basis of their spectroscopic data and comparison with reported NMR data. Compounds 1-9 exhibited considerable antiproliferative activity against breast adenocarcinoma (MCF-7), colorectal carcinoma (HCT-116) and hepatocellular carcinoma cells (HepG2). Compounds 3, 5 and 9 were selected for subsequent investigations regarding their mechanism of cell death induction (differential apoptosis/necrosis assessment) and their influence on cell cycle distribution. PMID:27399730

  12. Simulations of circular dichroism spectra of a pair of diterpene enantiomers by time-dependent density functional theory

    NASA Astrophysics Data System (ADS)

    Liaw, Chih-Chuang; Chang, Jia-Lin; Chen, Shou-Fong; Huang, Jhih-Hong; Sie, Jyun-Fu; Cheng, Yung-Yi

    2011-11-01

    We present the first theoretical study on a pair of diterpene enantiomers of formula C 21H 34O 5, which were newly isolated from plants and identified as 3β,5β-dihydroxy-16 α/ β-methoxyhalima-13(14)-en-15,16-olide. The equilibrium geometries and harmonic vibrational frequencies of their low-lying conformers were obtained by using the AM1 and B3LYP/6-31+G(d) methods. At the optimized geometries, rotatory strengths of six excited states of each conformer were computed by the time-dependent density functional theory. The electronic circular dichroism spectra were simulated by taking Boltzmann averaging and considering the solvent effect, from which the absolute configurations of the enantiomers were determined. Their vibrational circular dichroism spectra were also predicted.

  13. Novel bioactive diterpenoids from Aframomum aulacocarpos.

    PubMed

    Ayafor, J F; Tchuendem, M H; Nyasse, B; Tillequin, F; Anke, H

    1994-07-01

    Three new labdane diterpenes, 12 alpha,17-epoxy-3 beta-hydroxy-8(9),13- labdadien-16,15-olide (aulacocarpinolide) [1], methyl 8 beta,17:14 zeta,15-diepoxy-3 beta-hydroxy- 12E-labden-16-oate (aulacocarpin A) [2], and methyl 8 beta,17:14 zeta,15-diepoxy-3 beta,6 beta- dihydroxy-12E-labden-16-oate (aulacocarpin B) [3] have been isolated from the Cameroonian spice, Aframomum aulacocarpos, and their structures elucidated using spectroscopic techniques. The known bioactive diterpene dialdehyde, 8 beta,17-epoxy-12E-labdene-15,16-dial (aframodial) [4] was also isolated. Compounds 1-3 showed weak antimicrobial and cytotoxic activities.

  14. Two new labdane diterpenoids from the rhizomes of Isodon yuennanensis.

    PubMed

    Huang, Zhen-Yuan; Huang, Bo; Xiao, Chao-Jiang; Dong, Xiang; Jiang, Bei

    2015-01-01

    Two new labdane diterpenoids, s-trans-8(17),12E,14-labdatrien-20-oic acid (1), s-trans-12E,14-labdadien-20,8β-olide (2), along with 10 known compounds, hinokiol (3), ursonic acid (4), 2α,3α-dihydroxyolean-12-en-28-oic acid (5), 2α,3β,23-trihydroxyolean-12-en-28-oic acid (6), ethyl 3-(3,4-dihydroxyphenyl)lactate (7), ethyl rosmarinate (8), (Z,E)-2-(3,4-dihydroxyphenyl)ethenyl caffeic ester (9), tridecanoic acid (10), β-sitosterol (11) and daucosterol (12), were isolated from the 70% acetone extract of the rhizomes of Isodon yuennanensis. Their structures were elucidated based on the analyses of extensive spectroscopic data and physicochemical properties. PMID:25420949

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

    PubMed

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

    2015-06-01

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

  16. Antiproliferative Scalarane-Based Metabolites from the Red Sea Sponge Hyrtios erectus

    PubMed Central

    Elhady, Sameh S.; Al-Abd, Ahmed M.; El-Halawany, Ali M.; Alahdal, Abdulrahman M.; Hassanean, Hashim A.; Ahmed, Safwat A.

    2016-01-01

    Two new sesterterpenes analogs, namely, 12-acetoxy,16-epi-hyrtiolide (1) and 12β-acetoxy,16β-methoxy,20α-hydroxy-17-scalaren-19,20-olide (2), containing a scalarane-based framework along with seven previously reported scalarane-type sesterterpenes (3–9) have been isolated from the sponge Hyrtios erectus (order Dictyoceratida) collected from the Red Sea, Egypt. The structures of the isolated compounds were elucidated on the basis of their spectroscopic data and comparison with reported NMR data. Compounds 1–9 exhibited considerable antiproliferative activity against breast adenocarcinoma (MCF-7), colorectal carcinoma (HCT-116) and hepatocellular carcinoma cells (HepG2). Compounds 3, 5 and 9 were selected for subsequent investigations regarding their mechanism of cell death induction (differential apoptosis/necrosis assessment) and their influence on cell cycle distribution. PMID:27399730

  17. Fourier transform-infrared spectroscopy and Gas chromatography-mass spectroscopy: reliable techniques for analysis of Parthenium mediated vermicompost.

    PubMed

    Rajiv, P; Rajeshwari, Sivaraj; Venckatesh, Rajendran

    2013-12-01

    Fourier transform infrared spectroscopy (FT-IR) and Gas chromatography-mass spectroscopy have been carried out to investigate the chemical composition of Parthenium mediated vermicompost. Four different concentrations of Parthenium and cow dung mixtures were vermicomposted using the earthworms (Eudrilus eugeniae). FT-IR spectra reveal the absence of Parthenin toxin (sesquiterpene lactone) and phenols in vermicompost which was obtained from high concentration of cow dung mixed treatments. GC-MS analysis shows no phenolic compounds and predominant level of intermediate metabolites such as 4,8,12,16-Tetramethylheptadecan-4-olide (7.61%), 2-Pentadecanone, 6,10,14-trimethyl- (5.29%) and Methyl 16-methyl-heptadecanoate (4.69%) during the vermicomposting process. Spectral results indicated that Parthenin toxin and phenols can be eradicated via vermicomposting if mixed with appropriate quantity of cow dung.

  18. Fourier transform-infrared spectroscopy and Gas chromatography-mass spectroscopy: Reliable techniques for analysis of Parthenium mediated vermicompost

    NASA Astrophysics Data System (ADS)

    Rajiv, P.; Rajeshwari, Sivaraj; Venckatesh, Rajendran

    2013-12-01

    Fourier transform infrared spectroscopy (FT-IR) and Gas chromatography-mass spectroscopy have been carried out to investigate the chemical composition of Parthenium mediated vermicompost. Four different concentrations of Parthenium and cow dung mixtures were vermicomposted using the earthworms (Eudrilus eugeniae). FT-IR spectra reveal the absence of Parthenin toxin (sesquiterpene lactone) and phenols in vermicompost which was obtained from high concentration of cow dung mixed treatments. GC-MS analysis shows no phenolic compounds and predominant level of intermediate metabolites such as 4,8,12,16-Tetramethylheptadecan-4-olide (7.61%), 2-Pentadecanone, 6,10,14-trimethyl- (5.29%) and Methyl 16-methyl-heptadecanoate (4.69%) during the vermicomposting process. Spectral results indicated that Parthenin toxin and phenols can be eradicated via vermicomposting if mixed with appropriate quantity of cow dung.

  19. Microbial metabolism of haloaromatics: isolation and properties of a chlorobenzene-degrading bacterium

    SciTech Connect

    Reineke, W.; Knackmuss, H.J.

    1984-02-01

    A chlorobenzene-degrading bacterium was isolated by continuous enrichment from a mixture of soil and sewage samples. This organism, strain WR1306, was grown in a chemostat on a mineral medium with chlorobenzene being supplied through the vapor phase with a critical D/sub c/ value at a dilution rate of 0.55 h/sup -1/. Maximum growth rates in batch culture were accomplished at substrate concentrations of less than or equal to 0.5 mM in the culture medium. During growth on chlorobenzene, stoichiometric amounts of chloride were released. Respiration data and enzyme activities in cell extracts as well as the isolation of 3-chlorocatechol from the culture fluid are consistent with the degradation of chlorobenzene via 3-chloro-cis-1,2-dihydroxycyclohexa-3,5-diene, 3-chlorocatechol, 2-chloro-cis, cis-muconate, trans-4-carboxymethylenebut-2-en-4-olide, maleylacetate, and 3-oxoadipate. 55 references.

  20. New eudesmane sesquiterpenes from Alpinia oxyphylla and determination of their inhibitory effects on microglia.

    PubMed

    Jiang, Bei; Wang, Wen-Jing; Li, Man-Ping; Huang, Xiao-Jun; Huang, Feng; Gao, Hao; Sun, Ping-Hua; He, Ming-Fang; Jiang, Zheng-Jin; Zhang, Xiao-Qi; Ye, Wen-Cai

    2013-07-01

    The fruits of Alpinia oxyphylla are used as healthcare products for the protection on neurons and prevention of dementia. Two new noreudesmane sesquiterpenoids, (5R,7S,10S)-5-hydroxy-13-noreudesma-3-en-2,11-dione (1) and (10R)-13-noreudesma-4,6-dien-3,11-dione (2), and a new eudesmane sesquiterpenoid, (5S,8R,10R)-2-oxoeudesma-3,7(11)-dien-12,8-olide (3), as well as 12 known sesquiterpenoids, were isolated from the fruits of A. oxyphylla. The structures of the new compounds (1-3) were elucidated on the basis of spectroscopic data and circular dichroism experiments. All isolates were evaluated their neuroprotective potential by inhibitory assay on nitric oxide (NO) and tumor necrosis factor-α (TNF-α) production in lipopolysaccharide (LPS)-induced mouse microglia BV-2 cells.

  1. 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.

  2. [Cembranoid diterpenes from soft coral Sinularia sp].

    PubMed

    Lv, Fang; Wang, Xianjie; Dai, Rongji; Deng, Yulin

    2010-01-01

    A soft coral Sinularia sp., collected from the South China Sea, was selected to investigate the bioactive and chemical constituents. The EtOAc fraction were isolated by repeatedly silica gel and Sephadex LH-20 column chromatography to obtain lobophytolide A (1), 3-dehydroxylpresinularolide B (2), sarcophine (3), 3 beta-acetoxyisolobophytolide (4), Crassocolide D (5), (3E,7E,11E)-6-acetoxy-3,7,11,15(17)-cembratrien-16,14-olide (6). The structures of compounds 1-6 were determined on the basis of spectroscopic data analysis. All compounds were tested against a small panel of human tumor cell lines. And these compounds were obtained for the first time from this coral.

  3. Enzymatic formation, stability, and spontaneous reactions of 4-fluoromuconolactone, a metabolite of the bacterial degradation of 4-fluorobenzoate.

    PubMed Central

    Schlömann, M; Fischer, P; Schmidt, E; Knackmuss, H J

    1990-01-01

    Enzymatic conversion of 4-fluorocatechol in the simultaneous presence of partially purified preparations of catechol 1,2-dioxygenase from Pseudomonas cepacia and muconate cycloisomerase from Alcaligenes eutrophus 335 yielded a product that was unambiguously identified as (+)-4-fluoromuconolactone [(+)-4-carboxymethyl-4-fluoro-but-2-en-4-olide]. This compound was shown to be the only major product formed from 3-fluoro-cis,cis-muconate by the action of muconate cycloisomerases from A. eutrophus 335, A. eutrophus JMP134, and P. cepacia as well as by the action of dichloromuconate cycloisomerase from A. eutrophus JMP134. This finding implies that dichloromuconate cycloisomerase, like the muconate cycloisomerases, catalyzes primarily a cycloisomerization reaction, which only in the case of chloro- and bromo-substituted substrates is connected to a dehalogenation. 4-Fluoromuconolactone at pH 7 decomposes by spontaneous reactions mainly to maleylacetate, which then decarboxylates to give cis-acetylacrylate. Although significant amounts of an unidentified compound are also formed from the fluorolactone, HF elimination to the two isomeric dienelactones (4-carboxymethylenebut-2-en-4-olides) is negligible. However, all spontaneous reactions proceed so slowly that an enzymatic conversion of 4-fluoromuconolactone must be assumed. Participation of dienelactone hydrolases in this reaction is indicated by their induction during growth of various strains with 4-fluorobenzoate. However, experiments with cell extracts of P. putida A3.12 suggest that at least one other hydrolytic enzyme is able to contribute to 4-fluoromuconolactone conversion. In light of these observations, earlier proposals for a 4-fluorobenzoate degradative pathway are discussed. PMID:2394680

  4. Improving detection tools for emerald ash borer (Coleoptera: Buprestidae): comparison of multifunnel traps, prism traps, and lure types at varying population densities.

    PubMed

    Crook, Damon J; Francese, Joseph A; Rietz, Michael L; Lance, David R; Hull-Sanders, Helen M; Mastro, Victor C; Silk, Peter J; Ryall, Krista L

    2014-08-01

    The emerald ash borer, Agrilus planipennis Fairmaire (Coleoptera: Buprestidae), is a serious invasive pest of North American ash (Fraxinus spp.) that has caused devastating mortality since it was first identified in North America in 2002. In 2012, we conducted field trapping assays that tested the efficacy of purple prism and fluon-coated green multifunnel (Lindgren funnel) traps. Traps were baited with combinations of several lures that were previously shown to be attractive to A. planipennis: manuka oil--a sesquiterpene-rich oil, (3Z)-hexenol--a green leaf volatile, or (3Z)-dodecen-12-olide [= (3Z)-lactone], a sex pheromone. Eighty-nine blocks (trap lines) were tested throughout nine states along the outer edges of the currently known A. planipennis infestation in North America. Trap catch was highest on fluon-coated green multifunnel traps, and trap detections at sites with low A. planipennis population density ranged from 72 to 76% for all trap and lure types tested. (3Z)-hexenol and (3Z)-lactone baited traps functioned as well as (3Z)-hexenol and manuka oil-baited traps. Independent of the lure used, detection rates on green fluon-coated multifunnel traps were comparable with glued purple prism traps in areas with low A. planipennis population densities. PMID:25195441

  5. Screening alpha-glucosidase and alpha-amylase inhibitors from natural compounds by molecular docking in silico.

    PubMed

    Jhong, Chien-Hung; Riyaphan, Jirawat; Lin, Shih-Hung; Chia, Yi-Chen; Weng, Ching-Feng

    2015-01-01

    The alpha-glucosidase inhibitor is a common oral anti-diabetic drug used for controlling carbohydrates normally converted into simple sugars and absorbed by the intestines. However, some adverse clinical effects have been observed. The present study seeks an alternative drug that can regulate the hyperglycemia by down-regulating alpha-glucosidase and alpha-amylase activity by molecular docking approach to screen the hyperglycemia antagonist against alpha-glucosidase and alpha-amylase activities from the 47 natural compounds. The docking data showed that Curcumin, 16-hydroxy-cleroda-3,13-dine-16,15-olide (16-H), Docosanol, Tetracosanol, Antroquinonol, Berberine, Catechin, Quercetin, Actinodaphnine, and Rutin from 47 natural compounds had binding ability towards alpha-amylase and alpha-glucosidase as well. Curcumin had a better biding ability of alpha-amylase than the other natural compounds. Analyzed alpha-glucosidase activity reveals natural compound inhibitors (below 0.5 mM) are Curcumin, Actinodaphnine, 16-H, Quercetin, Berberine, and Catechin when compared to the commercial drug Acarbose (3 mM). A natural compound with alpha-amylase inhibitors (below 0.5 mM) includes Curcumin, Berberine, Docosanol, 16-H, Actinodaphnine/Tetracosanol, Catechin, and Quercetin when compared to Acarbose (1 mM). When taken together, the implication is that molecular docking is a fast and effective way to screen alpha-glucosidase and alpha-amylase inhibitors as lead compounds of natural sources isolated from medicinal plants.

  6. Cytotoxic triterpenoids and steroids from the bark of Melia azedarach.

    PubMed

    Wu, Shi-Biao; Bao, Qiu-Ying; Wang, Wen-Xuan; Zhao, Yun; Xia, Gang; Zhao, Zheng; Zeng, Huaqiang; Hu, Jin-Feng

    2011-06-01

    Two new triterpenoids (1, 2) and two new steroids (3, 4) along with twelve related known compounds (5-16) were isolated from the bark of Melia azedarach. The new structures were elucidated by means of spectroscopic methods and molecular modeling studies and found to be 21,24-cycloeupha-7-ene-3 β,16 β,21 α,25-tetrol (1), 3 β-acetoxy-12 β-hydroxy-eupha-7,24-dien-21,16 β-olide (2), 29-hydroperoxy-stigmasta-7,24(28) E-dien-3 β-ol (3), and 24 ξ-hydroperoxy-24-vinyl-lathosterol (4). All isolated compounds were tested for their cytotoxic activity against three human cancer cell lines (A549, H460, HGC27) using the CellTiter Glo™ luminescent cell viability assay. Among them, compounds 2- 4, 24 ξ-hydroperoxy-24-vinyl-cholesterol (6), kulinone (7), meliastatin 3 ( 8), 3-oxo-olean-12-en-28-oic acid (10), and (22 E,24 S)-5 α,8 α-epidioxy-24-methyl-cholesta-6,22-dien-3 β-ol (12) were found to have cytotoxic effects, with IC₅₀ values of 5.6-21.2 µg/mL.

  7. An abietane diterpene from Salvia cuspidata and some new derivatives are active against Trypanosoma cruzi.

    PubMed

    Lozano, E S; Spina, R M; Tonn, C E; Sosa, M A; Cifuente, D A

    2015-12-01

    The Plant Kingdom is an excellent source for obtaining natural compounds with antiprotozoal activity. In the present work, we studied the effect of the diterpene 12-hydroxy-11,14-diketo-6,8,12-abietatrien-19,20-olide (HABTO) obtained from the aerial parts of Salvia cuspidata on Trypanosoma cruzi epimastigotes. This compound was found to inhibit parasite growth even at low concentrations (IC50 5 μg/mL) and with low toxicity on mammalian cells. In addition, this diterpene induced an intense vacuolization within the parasites. In order to obtain analogs with greater lipophilicity, chemical modifications on the enol moiety were carried out to obtain the acetyl (AABTO), the sylil (SABTO) and the allyl (ALLABTO) derivatives. We observed that the SABTO was the most effective one on the parasites, and the effect could be attributed to a greater lipophilicity of this compound. Taking into account these data we conclude that the increase of lipophilicity by chemical modifications is an adequate strategy for improving the trypanocidal activity of this kind abietane diterpenes.

  8. A Modeling and Experimental Framework for Controls for Fuel Cells

    SciTech Connect

    Lu, Ning; Sun, Xin; Khaleel, Mohammad A.

    2006-03-15

    OLID oxide fuel cells (SOFCs) hold the promise of playing a major role in future power grids either as distributed generators (DGs) or as stand-alone power units because of their higher efficiency, lower emission, modular structure, and higher generation capability over other DGs or batteries. SOFCs operate at temperatures ranging from 600 C to 1000 C. To avoid thermal shock during heat-up as well as operation, inlet flow (fuel and air) temperatures and speeds must be carefully controlled to maintain the temperature gradient within the SOFC stack. Furthermore, increased fuel flow tends to decrease the fuel utilization and increase uniformity of the reaction rates across the active area, while decreased fuel flow tends to increase the fuel utilization but it can cause local fuel depletion and cold spots that exacerbate temperature non-uniformities [1]. Therefore, when maintaining reasonable fuel utilization at any loading level, the air flow rate and the fuel flow rate must be adjusted so that the fuel distribution and temperature gradient across the cell is more uniform.

  9. Differential growth inhibitory effects of highly oxygenated guaianolides isolated from the Middle Eastern indigenous plant Achillea falcata in HCT-116 colorectal cancer cells.

    PubMed

    Tohme, Rita; Al Aaraj, Lamis; Ghaddar, Tarek; Gali-Muhtasib, Hala; Saliba, Najat A; Darwiche, Nadine

    2013-01-01

    Medicinal plants play a crucial role in traditional medicine and in the maintenance of human health worldwide. Sesquiterpene lactones represent an interesting group of plant-derived compounds that are currently being tested as lead drugs in cancer clinical trials. Achillea falcata is a medicinal plant indigenous to the Middle Eastern region and belongs to the Asteraceae family, which is known to be rich in sesquiterpene lactones. We subjected Achillea falcata extracts to bioassay-guided fractionation against the growth of HCT-116 colorectal cancer cells and identified four secotanapartholides, namely 3-β-methoxy-isosecotanapartholide (1), isosecotanapartholide (2), tanaphallin (3), and 8-hydroxy-3-methoxyisosecotanapartholide (4). Three highly oxygenated guaianolides were isolated for the first time from Achillea falcata, namely rupin A (5), chrysartemin B (6), and 1β, 2β-epoxy-3β,4α,10α-trihydroxyguaian-6α,12-olide (7). These sesquiterpene lactones showed no or minor cytotoxicity while exhibiting promising anticancer effects against HCT-116 cells. Further structure-activity relationship studies related the bioactivity of the tested compounds to their skeleton, their lipophilicity, and to the type of functional groups neighboring the main alkylating center of the molecule. PMID:23860275

  10. Fragrant volatile sesquiterpenoids isolated from the essential oil of Laggera pterodonta by using olfactory-guided fractionation.

    PubMed

    Gu, Jian-Long; Li, Zhi-Jian; Zhang, Hong-Xia; Du, Zhi-Zhi

    2014-09-01

    Chemical composition of the essential oil from Laggera pterodonta (Compositae) was inverstigated. GC/MS Analyses led to the identification of 68 components, representing more than 96% of the total oil. By focusing on the woody note fraction of the essential oil, one new bisabolane-type sesquiterpenoid, bisabola-2,7(14),11-trien-10-ol (1), together with ten known compounds, bisabolol oxide B (2), ylangenol (3), copaborneol (4), guai-11-en-10-ol (5), spathulenol (6), aromadendran-10-ol (7), caryophyllenol (8), 5α,7α-eudesm-11(13)-en-4α-ol (9), γ-costic acid (10), and eudesma-4(15),11(13)-diene-12,5β-olide (11), were isolated by using olfactory-guided fractionation. The structures of the eleven compounds were determined by NMR and MS analyses. All the volatile compounds reported here were isolated for the first time from this plant. On the basis of preliminary odor assessment, the odor of the woody-note fractions of the essential oil was assumed to be due to these isolated sesquiterpenoids. PMID:25238080

  11. Bioactive-guided identification of labdane diterpenoids from aerial parts of Aristeguietia glutinosa as anti-Trypanosoma cruzi agents.

    PubMed

    Varela, Javier; Lavaggi, María L; Cabrera, Mauricio; Rodríguez, Alejandra; Miño, Patricio; Chiriboga, Ximena; Cerecetto, Hugo; González, Mercedes

    2012-09-01

    A bioactive-guided investigation of the hydro-ethanolic extract of aerial parts of Aristeguietia glutinosa Lam. resulted in the isolation of two diterpenoids, (+)-15-hydroxy-labd-7-en-17-al (1) and (+)-13,14,15,16-tetranor-labd-7-en-17,12-olide (2), as the anti-Trypanosoma cruzi active principles. The structures of 1 and 2 were determined by spectroscopic analysis. The hydro-ethanolic extract showed anti-T. cruzi activity (IC50 = 19.6 microg/mL) whereas the isolated compounds 1 and 2 were near to seven- and one and a half-fold (IC50 = 3.0 and 15.6 microg/mL), respectively more active than the original extract. Labdene 1, equipotent as the reference compound (Nifurtimox), displayed low hemolytic activity, low toxicity against murine macrophages, and absence of mutagenicity. These results support the vernacular medicinal use of this plant as an anti-T. cruzi agent. PMID:23074890

  12. (R)-Desmolactone Is a Sex Pheromone or Sex Attractant for the Endangered Valley Elderberry Longhorn Beetle Desmocerus californicus dimorphus and Several Congeners (Cerambycidae: Lepturinae)

    PubMed Central

    Ray, Ann M.; Arnold, Richard A.; Swift, Ian; Schapker, Philip A.; McCann, Sean; Marshall, Christopher J.; McElfresh, J. Steven; Millar, Jocelyn G.

    2014-01-01

    We report here that (4R,9Z)-hexadec-9-en-4-olide [(R)-desmolactone] is a sex attractant or sex pheromone for multiple species and subspecies in the cerambycid genus Desmocerus. This compound was previously identified as a female-produced sex attractant pheromone of Desmocerus californicus californicus. Headspace volatiles from female Desmocerus aureipennis aureipennis contained (R)-desmolactone, and the antennae of adult males of two species responded strongly to synthetic (R)-desmolactone in coupled gas chromatography-electroantennogram analyses. In field bioassays in California, Oregon, and British Columbia, traps baited with synthetic (R)-desmolactone captured males of several Desmocerus species and subspecies. Only male beetles were captured, indicating that this compound acts as a sex-specific attractant, rather than as a signal for aggregation. In targeted field bioassays, males of the US federally threatened subspecies Desmocerus californicus dimorphus responded to the synthetic attractant in a dose dependent manner. Our results represent the first example of a “generic” sex pheromone used by multiple species in the subfamily Lepturinae, and demonstrate that pheromone-baited traps may be a sensitive and efficient method of monitoring the threatened species Desmocerus californicus dimorphus, commonly known as the valley elderberry longhorn beetle. PMID:25521293

  13. Three new triterpenoid saponins from root of Gardenia jasminoides Ellis.

    PubMed

    Wang, Jing; Lu, Jincai; Lv, Chongning; Xu, Tanye; Jia, Lingyun

    2012-12-01

    Three new compounds (Gardeniside A-C), 11α,12α-epoxy-3β-[(O-β-D-glucuronopyranoside-6'-O-methly ester)oxy]olean-28,13-olide (1), siaresinolic acid 3-O-β-D-glucuronopyranoside-6'-O-methly ester (2), and 3-O-β-D- glucuronopyranoside-6'-O-methly ester-siaresinolic acid-28-O-β-D- glucopyranoside (3), with seven known compounds oleanolic acid 3-O-β-D- glucuronopyranoside-6'-O-methly ester (4), oleanolic acid 3-O-β-D- glucuropyranoside (5), hederagenin 3-O-β-D- glucuronopyranoside-6'-O- methly ester (6), chikusetsusaponin IVa methyl ester (7), chikusetsusaponin (8), chikusetsusaponin IVa butyl ester (9), siaresinolic acid 28-o-β-d-glucopyranosyl ester (10) were isolated from the root of Gardenia jasminoides Ellis. Six compounds (1, 4-7, and 9) showed cytotoxic activities against HeLa, A549, MCF-7 and A354-S2 cell lines. PMID:22796399

  14. Chemical structure and biodegradability of halogenated aromatic compounds. Halogenated muconic acids as intermediates.

    PubMed Central

    Schmidt, E; Remberg, G; Knackmuss, H J

    1980-01-01

    Substituted muconic acids were prepared from the corresponding catechols by pyrocatechase II from Pseudomonas sp. B13. The stabilities of substituted muconic acids were compared under different pH conditions. 3-Substituted cis, cis-muconic acids cycloisomerized readily in slightly acidic solutions, whereas 2-chloro- and 2-fluoro-cis,cis-muconic acids were stable under these conditions and could be isolated as crystalline compounds. They were isomerized to the cis, trans-form in highly acidic solution (pH 1), particularly when heated to 80 degrees C. Cycloisomerization of 2-chloro-cis,cis-muconic acid in 75% (v/v) H2SO4 yields 4-carboxymethyl-2-chloro-but-2-en-4-olide (4-chloro-2,5-dihydro-5-oxo-3H-furan-2-ylacetic acid). THe cis,cis-configuration of 2-chloromuconic acid was certified by 1H n.m.r. spectroscopy and by enzymic cycloisomerization. Although the cis,cis-configuration of 2-fluoromuconic acid was confirmed by corresponding spectroscopic data, it was not cycloisomerized by crude extracts or cycloisomerase II preparations from Pseudomonas sp. B13. PMID:7305905

  15. Influence of Finite Element Software on Energy Release Rates Computed Using the Virtual Crack Closure Technique

    NASA Technical Reports Server (NTRS)

    Krueger, Ronald; Goetze, Dirk; Ransom, Jonathon (Technical Monitor)

    2006-01-01

    Strain energy release rates were computed along straight delamination fronts of Double Cantilever Beam, End-Notched Flexure and Single Leg Bending specimens using the Virtual Crack Closure Technique (VCCT). Th e results were based on finite element analyses using ABAQUS# and ANSYS# and were calculated from the finite element results using the same post-processing routine to assure a consistent procedure. Mixed-mode strain energy release rates obtained from post-processing finite elem ent results were in good agreement for all element types used and all specimens modeled. Compared to previous studies, the models made of s olid twenty-node hexahedral elements and solid eight-node incompatible mode elements yielded excellent results. For both codes, models made of standard brick elements and elements with reduced integration did not correctly capture the distribution of the energy release rate acr oss the width of the specimens for the models chosen. The results suggested that element types with similar formulation yield matching results independent of the finite element software used. For comparison, m ixed-mode strain energy release rates were also calculated within ABAQUS#/Standard using the VCCT for ABAQUS# add on. For all specimens mod eled, mixed-mode strain energy release rates obtained from ABAQUS# finite element results using post-processing were almost identical to re sults calculated using the VCCT for ABAQUS# add on.

  16. New phytoconstituents from the aerial parts of Fumaria parviflora Lam

    PubMed Central

    Jameel, Mohammad; Ali, Abuzer; Ali, Mohammed

    2014-01-01

    Fumaria parviflora Lam. (Fumariaceae) is an annual herb found throughout the world. Traditionally it has great significance in various disorders. In folk medicine of Turkey it is used against hepato-biliary dysfunction and imported from Iran. In Charaka and Sushruta, it is recommended for treatment of fevers, blood disorders, chronic skin diseases, urinary diseases and cough. The compounds were isolated from methanolic extract of the plants by column chromatography using silica gel (60-120 mesh) as stationary phase and structure of the isolated compounds have been established on the basis of spectral data analysis and chemical reactions. Phytochemical investigation of its aerial parts led to the isolation of five new compounds characterized as (5αH,11αH)-8-oxo-homoiridolide (1), n-docosanyl-2-O-β-D-glucopyranosyl salicylate (2), 2-methyl-6-hydroxymethylenedodecan-10-oyl-12, 15-olide14-O-β-D-xylopyranoside (3), 4-oxo-stigmast-5-en-3β-ol-D-glucopyranoside (4) and salicylic acid-O-β-D-xylopyranoside (5) along with the known compounds α-D-glucopyranosyl hexadecanoate (6) and α-D-glucopyranosyl- (2 → 1ʹ)-α-D-glucopyranoside (7). The isolated compounds are useful as they will provide essential data and information for the further researchers and development of effective analytical marker for identity, purity and quality control of this traditional plant in future. PMID:24959414

  17. Male-produced pheromone of Spathius agrili, a parasitoid introduced for the biological control of the invasive emerald ash borer, Agrilus planipennis.

    PubMed

    Cossé, Allard A; Petroski, Richard J; Zilkowski, Bruce W; Vermillion, Karl; Lelito, Jonathan P; Cooperband, Miriam F; Gould, Juli R

    2012-04-01

    The braconid wasp, Spathius agrili, has been released in the U.S. as a biocontrol agent for the invasive emerald ash borer (Coleoptera: Buprestidae: Agrilus planipennis), a destructive pest of ash trees (Fraxinus spp.). We identified and synthesized seven male-specific volatile compounds. Three of these, dodecanal, (4R,11E)-tetradecen-4-olide, and (Z)-10-heptadecen-2-one, were the key behaviorally active components in flight tunnel bioassays. Male specificity was demonstrated by gas chromatographic comparison of male and female volatile emissions and whole body extracts. Identifications were aided by coupled gas chromatographic-mass spectrometric (GC-MS) analysis, microchemical reactions, NMR, chiral GC analysis, and GC and MS comparison with authentic standards. Both the racemic and chiral forms of the γ-lactone, as well as both E- and Z-isomers were synthesized. Flight tunnel behavioral tests showed positive male and female S. agrili responses to both natural pheromone and synthetic blends, with upwind flight and landing on the source. Large field-cage tests, using yellow sticky traps baited with pheromone, captured approximately 50% of the released male and female wasps in 24-h periods. The use of pheromone-baited traps in the field could simplify the current detection method for determining parasitoid establishment (i.e., laboriously felling and peeling ash trees for recovery of S. agrili from infested EAB larvae).

  18. Improving detection tools for emerald ash borer (Coleoptera: Buprestidae): comparison of multifunnel traps, prism traps, and lure types at varying population densities.

    PubMed

    Crook, Damon J; Francese, Joseph A; Rietz, Michael L; Lance, David R; Hull-Sanders, Helen M; Mastro, Victor C; Silk, Peter J; Ryall, Krista L

    2014-08-01

    The emerald ash borer, Agrilus planipennis Fairmaire (Coleoptera: Buprestidae), is a serious invasive pest of North American ash (Fraxinus spp.) that has caused devastating mortality since it was first identified in North America in 2002. In 2012, we conducted field trapping assays that tested the efficacy of purple prism and fluon-coated green multifunnel (Lindgren funnel) traps. Traps were baited with combinations of several lures that were previously shown to be attractive to A. planipennis: manuka oil--a sesquiterpene-rich oil, (3Z)-hexenol--a green leaf volatile, or (3Z)-dodecen-12-olide [= (3Z)-lactone], a sex pheromone. Eighty-nine blocks (trap lines) were tested throughout nine states along the outer edges of the currently known A. planipennis infestation in North America. Trap catch was highest on fluon-coated green multifunnel traps, and trap detections at sites with low A. planipennis population density ranged from 72 to 76% for all trap and lure types tested. (3Z)-hexenol and (3Z)-lactone baited traps functioned as well as (3Z)-hexenol and manuka oil-baited traps. Independent of the lure used, detection rates on green fluon-coated multifunnel traps were comparable with glued purple prism traps in areas with low A. planipennis population densities.

  19. Phytochemical composition, protective and therapeutic effect on gastric ulcer and α-amylase inhibitory activity of Achillea biebersteinii Afan.

    PubMed

    Abd-Alla, Howaida I; Shalaby, Nagwa M M; Hamed, Manal A; El-Rigal, Nagy Saba; Al-Ghamdi, Samira N; Bouajila, Jalloul

    2016-01-01

    Three sesquiterpene lactones [two germacranolides (micranthin and sintenin) and one guaianolide (4β,10α-dihydroxy-5β,7β,8βH-guaia-1,11(13)dien-12,8α-olide)] and four derivatives of 3-methoxy flavones (santin, quercetagetin-3,6,3'-trimethyl ether, quercetagetin-3,6-dimethyl ether, and 5,7 dihydroxy 3,3',4'-trimethoxy flavone) were isolated from the ethyl acetate extract (EAE) of the aerial parts of Achillea biebersteinii Afan. (Asteraceae). Evaluation of protective and therapeutic effects of EAE against ethanol-induced gastric ulcer in rats was carried. Antiulcer activity evaluation was done through measuring ulcer indices, stomach acidity, gastric volume and lesion counts. Oxidative stress markers; malondialdehyde, glutathione and superoxide dismutase were also estimated. The work was extended to determine the histopathological assessment of the stomach. Gastric ulcer exhibited a significant elevation of the ulcer index and oxidative stress markers. The extract attenuated these increments and recorded protective and therapeutic effects against gastric ulcer. Hyperglycaemia increases the mucosal susceptibility to ulcerogenic stimuli and predisposes gastric ulceration. In vitro α-amylase inhibitory assay was applied to evaluate the post prandial antihyperglycaemia activity. The result showing that the EAE has the ability to reduce starch-induced postprandial glycaemic excursions by virtue of potent intestinal α-amylase inhibitory activity. These findings demonstrated the remarkable potential of A. biebersteinii as valuable source of antiulcer agent with post prandial hyperglycaemia lowering effect.

  20. 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.

  1. Antimicrobial activities of novel mannosyl lipids isolated from the biocontrol fungus Simplicillium lamellicola BCP against phytopathogenic bacteria.

    PubMed

    Le Dang, Quang; Shin, Teak Soo; Park, Myung Soo; Choi, Yong Ho; Choi, Gyung Ja; Jang, Kyoung Soo; Kim, In Seon; Kim, Jin-Cheol

    2014-04-16

    The antagonistic fungus Simplicillium lamellicola BCP has been developed as a microbial biopesticide that effectively controls the development of various plant diseases caused by both pathogenic bacteria and pathogenic fungi. Antibacterial bioassay-directed fractionation was used to isolate mannosyl lipids from S. lamellicola BCP, and the structures of these compounds were elucidated using spectral analysis and chemical degradation. Three novel mannosyl lipids were characterized and identified as halymecins F and G and (3R,5R)-3-O-β-D-mannosyl-3,5-dihydrodecanoic acid. Massoia lactone and (3R, 5R)-3-hydroxydecan-5-olide were also isolated from S. lamellicola BCP. The three novel compounds inhibited the growth of the majority of phytopathogenic bacteria that were tested, and halymecin F displayed the strongest antibacterial activity. Agrobacterium tumefaciens was the most sensitive to the three novel compounds, with IC₅₀ values ranging from 1.58 to 24.8 μg/mL. The ethyl acetate extract of the fermentation broth from the antagonistic fungus effectively reduced the bacterial wilt caused by Ralstonia solanacearum on tomato seedlings. These results indicate that S. lamellicola BCP suppresses the development of plant bacterial diseases through the production of antibacterial metabolites. PMID:24660753

  2. Effects of Pheromone Release Rate and Trap Placement on Trapping of Agrilus planipennis (Coleoptera: Buprestidae) in Canada.

    PubMed

    Ryall, Krista L; Silk, Peter J; Fidgen, Jeff; Mayo, Peter; Lavallée, Robert; Guertin, Claude; Scarr, Taylor

    2015-06-01

    The emerald ash borer, Agrilus planipennis Fairmaire (Coleoptera: Buprestidae), is a devastating insect pest in its introduced range. A trapping system that increases trap catches or detection rates in low-density populations would be beneficial for survey programs. Five trapping experiments were conducted to investigate factors influencing capture rates of male beetles on dark green traps baited with the A. planipennis pheromone, (3Z)-dodecen-12-olide ((3Z)-lactone), plus the green leaf volatile, (3Z)-hexenol. Low doses (0.001-1.0 mg) of (3Z)-lactone + (3Z)-hexenol did not consistently increase captures of male A. planipennis. In other experiments, mean captures of males were significantly higher on traps baited with a moderate dose (3.0 mg/septum) of (3Z)-lactone + (3Z)-hexenol, compared with lower doses (0.001, 0.1, and 1.0 mg) or (3Z)-hexenol alone. Next, we demonstrated that addition of (3Z)-lactone to traps baited with (3Z)-hexenol resulted in significantly greater increases in male captures when pairs of traps were placed on the same tree, than when traps were placed on adjacent trees. Moreover, significantly more A. planipennis were captured on pheromone-baited traps placed in the southern versus northern aspect of the crown. These results highlight the importance of experimental set-up for elucidating lure treatment effects and also suggests the (3Z)-lactone may be more active at close range. Our findings increase our understanding of the pheromone ecology of this species and lend support toward the use of dark green traps baited with 3.0 mg (3Z)-lactone + (3Z)-hexenol deployed in the south aspect of the canopy for detection programs for this insect. PMID:26313980

  3. Interaction of Visual and Chemical CUES in Promoting Attraction of Agrilus planipennis.

    PubMed

    Domingue, Michael J; Andreadis, Stefanos S; Silk, Peter J; Ryall, Krista L; Baker, Thomas C

    2016-06-01

    Female emerald ash borers, Agrilus planipennis (Coleoptera: Buprestidae), emit a macrocyclic lactone, (Z)-3-dodecen-12-olide, that increases field trap captures on large-panel prism traps when co-emitted with the green leaf volatile (Z)-3-hexenol. We assessed attraction to these compounds by using visual decoy-baited branch traps, which attract males by mimicking a living female resting upon a leaf. Pairs of branch traps, with and without visual decoy beetles, were placed on green ash, Fraxinus pennsylvanica, trees, which were assigned different odor treatments: 1) no odor, 2) (Z)-3-hexenol alone, and 3) (Z)-3-hexenol-plus-lactone. Male captures were positively affected by the presence of decoys and the emission of either (Z)-3-hexenol or (Z)-3-hexenol plus lactone. The decoy-baited traps with the combination of (Z)-3-hexenol plus lactone caught more males than any other treatment. Greater male captures were associated with continuing captures later in the season, suggesting that decoy and odor attractants remain attractive throughout the flight period. Female captures were not affected by the visual decoys, but odors did influence captures, with the (Z)-3-hexenol plus lactone treatment catching the greatest number of females. The rare female trap captures were negatively correlated with the more common male captures on the odorless and (Z)-3-hexenol-baited traps, but were not correlated with male captures when the lactone was added. Thus, in the absence of the lactone, the visual signal of other conspecifics can inhibit female attraction. However, the pheromone attracts both sexes independently of the visual signal on the trap. PMID:27234006

  4. Chemical characterization of territorial marking fluid of male Bengal tiger, Panthera tigris.

    PubMed

    Burger, B V; Viviers, M Z; Bekker, J P I; le Roux, M; Fish, N; Fourie, W B; Weibchen, G

    2008-05-01

    The territorial marking fluid of the male Bengal tiger, Panthera tigris, consists of a mixture of urine and a small quantity of lipid material that may act as a controlled-release carrier for the volatile constituents of the fluid. Using gas chromatography and gas chromatography-mass spectrometry, 98 volatile compounds and elemental sulfur were identified in the marking fluid. Another 16 volatiles were tentatively identified. The majority of these compounds were alkanols, alkanals, 2-alkanones, branched and unbranched alkanoic acids, dimethyl esters of dicarboxylic acids, gamma- and delta-lactones, and compounds containing nitrogen or sulfur. Several samples of the marking fluid contained pure (R)-3-methyl-2-octanone, (R)-3-methyl-2-nonanone, and (R)-3-methyl-2-decanone, but these ketones were partly or completely racemized in other samples. The gamma-lactone (S)-(+)-(Z)-6-dodecen-4-olide and the C(8) to C(16) saturated (R)-gamma-lactones and (S)-delta-lactones were present in high enantiomeric purities. The chiral carboxylic acids, 2-methylnonanoic acid, 2-methyldecanoic acid, 2-methylundecanoic acid, and 2-ethylhexanoic acid were racemates. Cadaverine, putrescine, and 2-acetylpyrroline, previously reported as constituents of tiger urine, were not detected. The dominant contribution of some ketones, fatty acids, and lactones to the composition of the headspace of the marking fluid suggests that these compounds may be important constituents of the pheromone. Although it constitutes only a small proportion, the lipid fraction of the fluid contained larger quantities of the volatile organic compounds than the aqueous fraction (urine). The lipid derives its role as controlled-release carrier of the chemical message left by the tiger, from its affinity for the volatiles of the marking fluid. Six proteins with masses ranging from 16 to 69 kDa, inter alia, the carboxylesterase-like urinary protein known as cauxin, previously identified in the urine of the domestic cat

  5. Clerodane type diterpene as a novel antifungal agent from Polyalthia longifolia var. pendula.

    PubMed

    Bhattacharya, Asish K; Chand, Hemender R; John, Jyothis; Deshpande, Mukund V

    2015-04-13

    Bioactivity-guided chemical examination of methanolic extract of leaves of Polyalthia longifolia var. pendula led to the isolation of the active constituent, a diterpene 1 which was identified as 16α-hydroxycleroda-3,13(14)Z-dien-15,16-olide on the basis of its spectral data. Among the tested strains, diterpene 1 was found to exhibit antifungal activities having MIC90 values of 50.3, 100.6 and 201.2 μM against Candida albicans NCIM3557, Cryptococcus neoformans NCIM3542 (human pathogens) and Neurospora crassa NCIM870 (saprophyte), respectively. Initial, structure-activity-relationship (SAR) data generated by synthesizing some derivatives revealed that the double bond between C3-C4 and the free hydroxyl group at C16 are crucial for the antifungal activity of the diterpene 1. The mode of action of 1 in C. albicans is due to compromised cell membrane permeability and also probably due to disruption of cell wall structures. The red blood cell haemolysis of all the compounds (1-4) did not show any significant haemolysis and was found to be less than 15% for all the compounds when tested at highest concentration, i.e. 1200 μM. Interestingly, all the tested compounds inhibited Y-H transition in dimorphic C. albicans NCIM3557 at much lower concentration than their MIC90 values. Determination of ROS generation by diterpene 1 using DCFH-DA and DHR123 (dihydrorhodamine) staining of C. albicans NCIM3557 indicated production of intracellular ROS as a mechanism of antifungal activity.

  6. A clerodane diterpene inhibit adipogenesis by cell cycle arrest and ameliorate obesity in C57BL/6 mice.

    PubMed

    Beg, Muheeb; Shankar, Kripa; Varshney, Salil; Rajan, Sujith; Singh, Suriya Pratap; Jagdale, Pankaj; Puri, Anju; Chaudhari, Bhushan P; Sashidhara, Koneni V; Gaikwad, Anil Nilkanth

    2015-01-01

    A clerodane diterpene, 16α-Hydroxycleroda-3, 13 (14) Z-dien-15, 16-olide (compound 1) isolated from Polyalthia longifolia had previously been reported as a new structural class of HMG-CoA reductase inhibitor apart from statins. Statins are known to be anti-adipogenic in nature. The distant structural similarity between compound 1 and lovastatin (polyketide class of compound) prompted us to investigate effects of diterpene compound 1 on adipogenesis and thereby obesity. High content microscopy proved diterpene compound 1 exhibits better anti-adipogenic activity and less toxicity in differentiating adipocytes. Moreover, it reduced expression levels of PPARγ, C/EBPα and GLUT4 during differentiation in a time and concentration dependent manner. Diterpene compound 1 during early differentiation reduced MDI induced-Akt/mTOR phosphorylation and expression of cell cycle proteins, and thereby halted mitotic clonal expansion, the decisive factor in early adipogenesis. Further, its anti-adipogenic activity was validated in murine mesenchymal cell-line C3H10T1/2 and human mesenchymal stem cell models of adipogenic differentiation. When compound 1 was administered along with HFD, for another 8 weeks in 2 month HFD fed overweight mice (with BMI > 30 and impaired glucose tolerance), it attenuated weight gain and epididymal fat accumulation. It improved body glucose tolerance, reduced HFD induced increase in total cholesterol and leptin/adiponectin ratio. All these effects were comparable with standard anti-obesity drug Orlistat with added edge of potently decreasing circulating triglyceride levels comparable with normal chow fed group. Histological analysis shows that compound 1 inhibit adipocyte hypertrophy and decreased steatosis in hepatocytes. Both in vivo and in vitro results demonstrate a potential value of compound 1 as a novel anti-adipogenic and anti-obesity agent.

  7. High-Contrast Fluorescence Imaging in Fixed and Living Cells Using Optimized Optical Switches

    PubMed Central

    Wu, Liangxing; Dai, Yingrui; Jiang, Xiaoli; Petchprayoon, Chutima; Lee, Jessie E.; Jiang, Tao; Yan, Yuling; Marriott, Gerard

    2013-01-01

    We present the design, synthesis and characterization of new functionalized fluorescent optical switches for rapid, all-visible light-mediated manipulation of fluorescence signals from labelled structures within living cells, and as probes for high-contrast optical lock-in detection (OLID) imaging microscopy. A triazole-substituted BIPS (TzBIPS) is identified from a rational synthetic design strategy that undergoes robust, rapid and reversible, visible light-driven transitions between a colorless spiro- (SP) and a far-red absorbing merocyanine (MC) state within living cells. The excited MC-state of TzBIPS may also decay to the MC-ground state emitting near infra-red fluorescence, which is used as a sensitive and quantitative read-out of the state of the optical switch in living cells. The SP to MC transition for a membrane-targeted TzBIPS probe (C12-TzBIPS) is triggered at 405 nm at an energy level compatible with studies in living cells, while the action spectrum of the reverse transition (MC to SP) has a maximum at 650 nm. The SP to MC transition is complete within the 790 ns pixel dwell time of the confocal microscope, while a single cycle of optical switching between the SP and MC states in a region of interest is complete within 8 ms (125 Hz) within living cells, the fastest rate attained for any optical switch probe in a biological sample. This property can be exploited for real-time correction of background signals in living cells. A reactive form of TzBIPS is linked to secondary antibodies and used, in conjunction with an enhanced scope-based analysis of the modulated MC-fluorescence in immuno-stained cells, for high-contrast immunofluorescence microscopic analysis of the actin cytoskeleton. PMID:23755140

  8. Larvae of the parasitoid wasp Ampulex compressa sanitize their host, the American cockroach, with a blend of antimicrobials.

    PubMed

    Herzner, Gudrun; Schlecht, Anja; Dollhofer, Veronika; Parzefall, Christopher; Harrar, Klaus; Kreuzer, Andreas; Pilsl, Ludwig; Ruther, Joachim

    2013-01-22

    Food resources contaminated with spoilage or pathogenic microorganisms pose severe problems to all higher organisms. Here, we describe a food-hygienic strategy of the emerald cockroach wasp Ampulex compressa. The wasp larvae develop on and inside the American cockroach Periplaneta americana, a host that can harbor various putrefactive microbes, as well as human and insect pathogens. From P. americana, we isolated the Gram-negative bacterium Serratia marcescens, which is a potent entomopathogen that can rapidly kill insect larvae. It is also known as a food contaminant and as an opportunistic human pathogen. Using behavioral observations and chemical analyses, we demonstrated that A. compressa larvae impregnate their cockroach hosts from inside with large amounts of an oral secretion containing a blend of γ-lactones and isocoumarins with (R)-(-)-mellein [(R)-(-)-3,4-diydro-8-hydroxy-3-methylisocoumarin] and micromolide [(4R,9Z)-octadec-9-en-4-olide] as dominant components. We fractionated hexane extracts of the secretion and investigated the antimicrobial properties of the fraction containing the lactones and isocoumarins, as well as of synthetic (R)-(-)-mellein and micromolide, against S. marcescens and a Gram-positive bacterium, Staphylococcus hyicus, in broth microdilution assays. The test fraction inhibited growth of both tested bacteria. The activity of the fraction against S. marcescens was explained by (R)-(-)-mellein alone, and the activity against S. hyicus was explained by the combined action of (R)-(-)-mellein and micromolide. Our data suggest that the specific combination of antimicrobials in the larval secretion provides an effective frontline defense against the unpredictable spectrum of microbes that A. compressa larvae may encounter during their development inside their cockroach hosts.

  9. The microbiological transformation of two 15beta-hydroxy-ent-kaurene diterpenes by Gibberella fujikuroi.

    PubMed

    Fraga, Braulio M; Guillermo, Ricardo; Hernández, Melchor G

    2004-01-01

    The incubation of 15beta-hydroxy-3-oxo-ent-kaur-16-ene (1) with the fungus Gibberella fujikuroi afforded 11beta-hydroxy-3,15-dioxo-ent-kaurane (6), 11beta,15beta-dihydroxy-3-oxo-ent-kaur-16-ene (8), 7beta,11beta,15beta-trihydroxy-3-oxo-ent-kaur-16-ene (9), 7alpha,11beta-dihydroxy-3,15-dioxo-ent-kaurane (7), and 7alpha,11beta,15beta-trihydroxy-3-oxo-ent-kaur-16-ene (10). The incubation of 15beta-hydroxy-ent-kaur-2,16-diene (3) with the same fungus yielded 7alpha,11beta-dihydroxy-15-oxo-ent-kaur-2-ene (12), 7alpha,11beta,15beta-trihydroxy-ent-kaur-2,16-diene (13), 7beta,15beta-dihydroxy-ent-kaur-2,16-dien-19,6-olide (14), 1beta,7beta,15beta-trihydroxy-ent-kaur-2,16-dien-19-oic acid (15), 7alpha,11beta,16alpha-trihydroxy-15-oxo-ent-kaur-2-ene (17), and 7alpha,15beta,17-trihydroxy-11beta,16beta-epoxy-ent-kaur-2-ene (19). These results indicated that a 3-oxo group in ent-kaur-16-ene derivatives inhibits the oxidation at C-19, typical of the biosynthetic pathway of gibberellins and kaurenolides, while a 2,3-double bond or a 15beta-OH does not. In both substrates a 15beta-alcohol directs hydroxylations at C-11(beta) and C-7(alpha), while in those with a 2,3-double bond the functionalization of C-1(beta) is favored.

  10. 4-sulfomuconolactone hydrolases from Hydrogenophaga intermedia S1 and Agrobacterium radiobacter S2.

    PubMed

    Halak, Sad; Basta, Tamara; Bürger, Sibylle; Contzen, Matthias; Wray, Victor; Pieper, Dietmar Helmut; Stolz, Andreas

    2007-10-01

    The 4-carboxymethylen-4-sulfo-but-2-en-olide (4-sulfomuconolactone) hydrolases from Hydrogenophaga intermedia strain S1 and Agrobacterium radiobacter strain S2 are part of a modified protocatechuate pathway responsible for the degradation of 4-sulfocatechol. In both strains, the hydrolase-encoding genes occur downstream of those encoding the enzymes that catalyze the lactonization of 3-sulfomuconate. The deduced amino acid sequences of the 4-sulfomuconolactone hydrolases demonstrated the highest degree of sequence identity to 2-pyrone-4,6-dicarboxylate hydrolases, which take part in the meta cleavage pathway of protocatechuate. The 4-sulfomuconolactone hydrolases did not convert 2-pyrone-4,6-dicarboxylate, and the 2-pyrone-4,6-dicarboxylate hydrolase from Sphingomonas paucimobilis SYK-6 did not convert 4-sulfomuconolactone. Nevertheless, the presence of highly conserved histidine residues in the 4-sulfomuconolactone and the 2-pyrone-4,6-dicarboxylate hydrolases and some further sequence similarities suggested that both enzymes belong to the metallo-dependent hydrolases (the "amidohydrolase superfamily"). The 4-sulfomuconolactone hydrolases were heterologously expressed as His-tagged enzyme variants. Gel filtration experiments suggested that the enzymes are present as monomers in solution, with molecular weights of approximately 33,000 to 35,000. 4-Sulfomuconolactone was converted by sulfomuconolactone hydrolases to stoichiometric amounts of maleylacetate and sulfite. The 4-sulfomuconolactone hydrolases from both strains showed pH optima at pH 7 to 7.5 and rather similar catalytic constant (k(cat)/K(M))values. The suggested 4-sulfocatechol pathway from 4-sulfocatechol to maleylacetate was confirmed by in situ nuclear magnetic resonance analysis using the recombinantly expressed enzymes.

  11. Degradation of p-chlorotoluene by a mutant of Pseudomonas sp. strain JS6

    SciTech Connect

    Haigler, B.E.; Spain, J.C. )

    1989-02-01

    Pseudomonas sp. strain JS6 grows on chlorobenzene, p-dichlorobenzene, or toluene as a sole source of carbon and energy. It does not grow on p-chlorotoluene (p-CT). Growth on glucose in the presence of p-CT resulted in the accumulation of 4-chloro-2,3- dihydroxy-1-methyl benzene (3-chloro-6- methylcatechol), 4-chloro- 2,3-dihydroxy-1-methyl cyclohexa- 4,6-diene (p-CT dihydrodoil), and 2-methyl-4-carboxy methylenebut-2-en-4-olide (2-methyl dienelactone). Strain JS21, a spontaneous mutant capable of growth on p-CT, was isolated from cultures of strain JS6 after extended exposure to p-CT. In addition to growing on p-CT, JS21 grew on all of the substrates that supported growth of the parent strain, including p-dichlorobenzene, chlorobenzene, benzene, toluene, benzoate, p-hydroxybenzoate, phenol, and ethylbenzene. The pathway for degradation of p-CT by JS21 was investigated by respirometry, isolation of intermediates, and assay of enzymes in cell extracts. p-CT was converted to 3-chloro-6-methylcatechol by dioxygenase and dihydrodiol dehydrogenase enzymes. 3-Chloro-6-methylcatechol underwent ortho ring cleavage catalyzed by a catechol 1,2-dioxygenase to form 2-chloro-5-methyl-cis,cis-muconate, which was converted to 2-methyl dienelactone. A dienelactone hydrolase converted 2-methyl dienelactone to 2-methylmaleylacetic acid. Preliminary results indicate that a change in wild-type induction patterns allows JS21 to grow on p-CT.

  12. Chemical characterization of territorial marking fluid of male Bengal tiger, Panthera tigris.

    PubMed

    Burger, B V; Viviers, M Z; Bekker, J P I; le Roux, M; Fish, N; Fourie, W B; Weibchen, G

    2008-05-01

    The territorial marking fluid of the male Bengal tiger, Panthera tigris, consists of a mixture of urine and a small quantity of lipid material that may act as a controlled-release carrier for the volatile constituents of the fluid. Using gas chromatography and gas chromatography-mass spectrometry, 98 volatile compounds and elemental sulfur were identified in the marking fluid. Another 16 volatiles were tentatively identified. The majority of these compounds were alkanols, alkanals, 2-alkanones, branched and unbranched alkanoic acids, dimethyl esters of dicarboxylic acids, gamma- and delta-lactones, and compounds containing nitrogen or sulfur. Several samples of the marking fluid contained pure (R)-3-methyl-2-octanone, (R)-3-methyl-2-nonanone, and (R)-3-methyl-2-decanone, but these ketones were partly or completely racemized in other samples. The gamma-lactone (S)-(+)-(Z)-6-dodecen-4-olide and the C(8) to C(16) saturated (R)-gamma-lactones and (S)-delta-lactones were present in high enantiomeric purities. The chiral carboxylic acids, 2-methylnonanoic acid, 2-methyldecanoic acid, 2-methylundecanoic acid, and 2-ethylhexanoic acid were racemates. Cadaverine, putrescine, and 2-acetylpyrroline, previously reported as constituents of tiger urine, were not detected. The dominant contribution of some ketones, fatty acids, and lactones to the composition of the headspace of the marking fluid suggests that these compounds may be important constituents of the pheromone. Although it constitutes only a small proportion, the lipid fraction of the fluid contained larger quantities of the volatile organic compounds than the aqueous fraction (urine). The lipid derives its role as controlled-release carrier of the chemical message left by the tiger, from its affinity for the volatiles of the marking fluid. Six proteins with masses ranging from 16 to 69 kDa, inter alia, the carboxylesterase-like urinary protein known as cauxin, previously identified in the urine of the domestic cat

  13. New Abietane Diterpenes from Euphorbia Pseudocactus Berger (Euphorbiaceae) and Their Antimicrobial Activity

    PubMed Central

    Abdel-Monem, Azza Ramy; Abdelrahman, Enas Hussein

    2016-01-01

    Background: Euphorbia is the largest genus in Euphorbiaceae. Terpenoids were isolated from most species of this genus. Objective: Since no previous study was reported about Euphorbia pseudocactus Berger, we started here a phytochemical investigation on this species to isolate and identify its terpenoid constituents and to estimate the antimicrobial activity of the isolated compounds. Materials and Methods: The n-hexane fraction of the ethanolic extract of E. pseudocactus Berger was chromatographed on silica gel columns, the structures of the isolated compounds (1–5) were identified based on their MS, 1 D, and 2 D NMR spectral data. The antimicrobial activity of the n-hexane fraction and the isolated compounds (1–4) was investigated using diffusion plate method against Gram-positive (Staphylococcus aureus [12600] and Bacillus subtilis [6051]) and Gram-negative (Pseudomonas aeruginosa [10145] and Escherichia coli [11775]) bacteria, yeast (Candida albicans [7102]), and fungi (Aspergillus flavus). Results: Two triterpenes (glut-5-en-3 β-ol [1] and olean-12,15-diene-3 β-ol [2]) and three abietane diterpene (3-hydoxy-19-cyclopropenoyloxy-abietane [3], ent-abieta-9,12,14-triene-12,16-olide [4], and 12,19-dihydroxy-abieta-5-ene [5]) were isolated. Compound 1 exhibited no antibacterial activity against the tested bacteria, compound 2 and n-hexane fraction exhibited weak activity, whereas compounds 3 and 4 showed moderate activity. All samples showed no activity against the tested yeast and fungi. Discussion and Conclusion: Five compounds were isolated for the 1st time from E. pseudocactus Berger, three of them (3–5) are new natural compounds. As the major isolated compound (1) exhibited no antimicrobial activity, the observed activity of the n-hexane fraction is mainly due to its diterpenoid constituents. SUMMARY Two known triterpenes and three new diterpenes were isolated from n-hexane fraction of Euphorbia pseudocactusThe abietane diterpenoids showed higher

  14. Characterization of the genes encoding the 3-carboxy-cis,cis-muconate-lactonizing enzymes from the 4-sulfocatechol degradative pathways of Hydrogenophaga intermedia S1 and Agrobacterium radiobacter S2.

    PubMed

    Halak, Sad; Basta, Tamara; Bürger, Sibylle; Contzen, Matthias; Stolz, Andreas

    2006-11-01

    Hydrogenophaga intermedia strain S1 and Agrobacterium radiobacter strain S2 form a mixed bacterial culture which degrades sulfanilate (4-aminobenzenesulfonate) by a novel variation of the beta-ketoadipate pathway via 4-sulfocatechol and 3-sulfomuconate. It was previously proposed that the further metabolism of 3-sulfomuconate is catalysed by modified 3-carboxy-cis,cis-muconate-lactonizing enzymes (CMLEs) and that these 'type 2' enzymes were different from the conventional CMLEs ('type 1') from the protocatechuate pathway in their ability to convert 3-sulfomuconate in addition to 3-carboxy-cis,cis-muconate. In the present study the genes for two CMLEs (pcaB2S1 and pcaB2S2) were cloned from H. intermedia S1 and A. radiobacter S2, respectively. In both strains, these genes were located close to the previously identified genes encoding the 4-sulfocatechol-converting enzymes. The gene products of pcaB2S1 and pcaB2S2 were therefore tentatively identified as type 2 enzymes involved in the metabolism of 3-sulfomuconate. The genes were functionally expressed and the gene products were shown to convert 3-carboxy-cis,cis-muconate and 3-sulfomuconate. 4-Carboxymethylene-4-sulfo-but-2-en-olide (4-sulfomuconolactone) was identified by HPLC-MS as the product, which was enzymically formed from 3-sulfomuconate. His-tagged variants of both CMLEs were purified and compared with the CMLE from the protocatechuate pathway of Pseudomonas putida PRS2000 for the conversion of 3-carboxy-cis,cis-muconate and 3-sulfomuconate. The CMLEs from the 4-sulfocatechol pathway converted 3-sulfomuconate with considerably higher activities than 3-carboxy-cis,cis-muconate. Also the CMLE from P. putida converted 3-sulfomuconate, but this enzyme demonstrated a clear preference for 3-carboxy-cis,cis-muconate as substrate. Thus it was demonstrated that in the 4-sulfocatechol pathway, distinct CMLEs are formed, which are specifically adapted for the preferred conversion of sulfonated substrates.