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Sample records for laevad olid puust

  1. Synthesis of alkyl-substituted 2-halo-4-aminomethyl-2-buten-4-olides

    SciTech Connect

    Tyvorskii, V.I.; Tishchenko, I.G.; Kukharev, A.S.; Yushkevich, E.V.; Vlasov, S.F.

    1986-05-01

    The reaction of esters of alkyl-substituted (E)-5-amino-4-hydroxy-2,3,epoxy-valeric acids with some hydrohalic acids gave the corresponding 2-halo-4-amino-methyl-2-buten-4-olides, the hydrochlorides of which have diuretic activity.

  2. 2-buten-4-olide, an endogenous feeding suppressant, improves spatial performance through brain acidic fibroblast growth factor in mice.

    PubMed

    Li, X L; Aou, S; Li, A J; Hori, T; Tooyama, I; Oomura, Y

    2001-12-01

    Endogenous sugar acid 2-buten-4-olide, a satiety substance, has been shown to increase the blood glucose, norepinephrine, and glucocorticoid concentrations that are known to modulate learning and memory processes. The glucose-induced release of acidic fibroblast growth factor facilitated the hippocampus-dependent memory function. In the present study, we investigated the effect of 2-buten-4-olide on the spatial performance of male DDY mice undergoing the water maze task. The intraperitoneal injection of 2-buten-4-olide (5 mg/kg) facilitated the spatial performance, which was indicated by a reduction in the escape latency in which the mouse finds and climbs the goal platform in comparison to the vehicle-injected control mice. In the probe test after removing the platform, the 2-buten-4-olide-treated mice stayed a longer time in the quadrant where the platform was originally located and crossed more frequently at the platform location than did the control mice. The pretreatment of acidic fibroblast growth factor antibody injected into the lateral ventricle eliminated the effect of 2-buten-4-olide both during the training sessions and during the probe test. Therefore, 2-buten-4-olide was found to improve the spatial performance, and this effect is mediated, at least in part, by acidic fibroblast growth factor.

  3. Wedelolides A and B: novel sesquiterpene delta-lactones, (9R)-eudesman-9,12-olides, from Wedelia trilobata.

    PubMed

    That, Quang Ton; Jossang, Jean; Jossang, Akino; Kim, Phi Phung Nguyen; Jaureguiberry, Ginette

    2007-09-14

    Two new sesquiterpene lactones, wedelolides A (1) and B (2), were isolated by bioassay-guided fractionation from the leaves of Wedelia trilobata, together with known trilobolides 6-O-isobutyrate (3) and 6-O-methacrylate (4). The compounds 1 and 2 were the first examples of an unprecedented framework: a novel sesquiterpene delta-lactone, (9R)-eudesman-9,12-olide. The structures of the antimalarial wedelolides A (1) and B (2) were determined on the basis of MS and 2D NMR spectral analysis. The absolute configuration of eight carbon stereocenters of compounds 1 and 2 was determined to be 1S,4S,5S,6R,7S,8S,9R,10S by mean of auxiliary chiral MTPA derivatives.

  4. Syntheses and reactions of some new 2-arylidene-4-(biphenyl-4-yl)-but-3-en-4-olides with a study of their biological activity.

    PubMed

    Khan, M S Y; Husain, A

    2002-07-01

    2-Arylidene-4-(biphenyl-4-yl)but-3-en-4-olides also known as 3-arylidene-5-(biphenyl-4-yl)-2(3H)-furanones were prepared from 3-(4-phenyl-benzoyl) propionic acid and aromatic aldehydes. Some of the selected butenolides were reacted with ammonia and benzylamine to give corresponding pyrrolones and N-benzylpyrrolones respectively, which were characterized on the basis of 1H NMR and MS data and elemental analysis results. These compounds were tested for anti-inflammatory and anti-microbial actions. A few compounds were found to have promising anti-inflammatory activity while a fair in number of compounds showed a good anti-fungal activity and a promising antibacterial activity against S. aureus and E. coli.

  5. Bioactive (3Z,5E)-11,20-Epoxybriara-3,5-dien-7,18-olide Diterpenoids from the South China Sea Gorgonian Dichotella gemmacea

    PubMed Central

    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. PMID:21892354

  6. Rational design, synthesis and characterization of highly fluorescent optical switches for high-contrast optical lock-in detection (OLID) imaging microscopy in living cells

    PubMed Central

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

    2010-01-01

    A major challenge in cell biology is to elucidate molecular mechanisms that underlie the spatio-temporal control of cellular processes. These studies require microscope imaging techniques and associated optical probes that provide high-contrast and high-resolution images of specific proteins and their complexes. Auto-fluorescence however, can severely compromise image contrast and represents a fundamental limitation for imaging proteins within living cells. We have previously shown that optical switch probes and optical lock-in detection (OLID) image microscopy improve image contrast in high background environments. Here, we present the design, synthesis and characterization of amino- reactive and cell permeable optical switches that integrate the highly fluorescent fluorophore, tetramethylrhodamine (TMR) and spironaphthoxazine (NISO), a highly efficient optical switch. The NISO moiety in TMR-NISO undergoes rapid and reversible, excited-state driven transitions between a colorless spiro (SP)-state and a colored merocyanine (MC)-state in response to irradiation with 365 nm and >530 nm light. In the MC-state, the TMR (donor) emission is almost completely extinguished by Förster resonance energy transfer (FRET) to the MC probe (acceptor), whereas in the colorless SP-state, the quantum yield for TMR fluorescence is maximal. Irradiation of TMR-NISO with a defined sequence of 365 nm and 546 nm manipulates the levels of SP and MC with concomitant modulation of FRET efficiency and the TMR fluorescence signal. High fidelity optical switching of TMR fluorescence is shown for TMR-NISO probes in vitro and for membrane permeable TMR-NISO within living cells. PMID:20674372

  7. 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

  8. The Effect of (1S,2S,3E,7E,11E)-3,7,11,15-Cembratetraen-17,2-Olide (LS-1) from Lobophyyum sp. on the Apoptosis Induction of SNU-C5 Human Colorectal Cancer Cells

    PubMed Central

    Kim, Eun-Ji; Kang, Jung Il; Tung, Nguyen-Huu; Kim, Young-Ho; Hyun, Jin Won; Koh, Young Sang; Chang, Weon-Young; Yoo, Eun Sook; Kang, Hee-Kyoung

    2016-01-01

    (1S,2S,3E,7E,11E)-3,7,11,15-cembratetraen-17,2-olide (LS-1), a marine cembrenolide diterpene, has anticancer activity against colon cancer cells such as HT-29, SNU-C5/5-FU (fluorouracil-resistant SNU-C5) and SNU-C5. However, the action mechanism of LS-1 on SNU-C5 human colon cancer cells has not been fully elucidated. In this study, we investigated whether the anticancer effect of LS-1 could result from apoptosis via the modulation of Wnt/β-catenin and the TGF-β pathways. When treated with the LS-1, we could observe the apoptotic characteristics such as apoptotic bodies and the increase of sub-G1 hypodiploid cell population, increase of Bax level, decrease of Bcl-2 expression, cleavage of procaspase-3 and cleavage of poly (ADP-ribose) polymerase in SNU-C5 cells. Furthermore, the apoptosis induction of SNU-C5 cells upon LS-1 treatment was also accompanied by the down-regulation of Wnt/β-catenin signaling pathway via the decrease of GSK-3β phosphorylation followed by the decrease of β-catenin level. In addition, the LS-1 induced the activation of TGF-β signaling pathway with the decrease of carcinoembryonic antigen which leads to decrease of c-Myc, an oncoprotein. These data suggest that the LS-1 could induce the apoptosis via the down-regulation of Wnt/β-catenin pathway and the activation of TGF-β pathway in SNU-C5 human colon cancer cells. The results support that the LS-1 might have potential for the treatment of human colon cancer. PMID:27469141

  9. 12-Nitro-methyl-14-deoxy-andro-graph-olide.

    PubMed

    Quan, Ji-Cai; Chen, Jing; Xu, Hao; Hu, Chen-Hui; Wang, Jin-Tang

    2008-06-28

    In the mol-ecule of the title compound {systematic name: 3-[2-(6-hydr-oxy-5-hydroxy-methyl-5,8a-dimethyl-2-methyl-ene-per-hydro-1-napth-yl)-1-(nitro-meth-yl)eth-yl]-2(4H)-furan-one}, C(21)H(31)NO(6), the cyclo-hexane rings have chair conformations. Intra-molecular O-H⋯O hydrogen bonding results in the formation of a six-membered non-planar ring with a twist conformation. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into infinite chains along the c axis.

  10. 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

  11. 3β-Acet­oxy-12α-chloro-d-friedooleanan-28,14β-olide

    PubMed Central

    Froelich, Anna; Kowiel, Marcin; Bednarczyk-Cwynar, Barbara; Zaprutko, Lucjusz; Gzella, Andrzej K.

    2011-01-01

    The title compound, C32H49ClO4, was obtained along with nitrile and lactam products in the POCl3-catalysed Beckmann rearrangement from 3β-acet­oxy-12-hydroxyiminoolean-28-olic acid methyl ester. The mechanism of the transformation leading to the title compound remains unclear and requires further investigation. Rings A, B and E are in chair conformations, ring C has a twisted-boat conformation, ring D a conformation halfway between boat and twisted-boat and rings D and E are cis-fused. In the crystal, mol­ecules are connected by weak inter­molecular C—H⋯O hydrogen bonds into layers extending parallel to the bc plane. PMID:21522426

  12. 15α,20β-Dihydr­oxy-6β-meth­oxy-6,7-seco-6,20-ep­oxy-1,7-olide-ent-kaur-16-ene

    PubMed Central

    Yan, Fu-Lin; Zhan, He-Qin; Feng, Chuang; Di, Xue-Mei

    2010-01-01

    The title compound, C21H30O6, a natural ent-kaurane diterpenoid, was obtained from the medicinal plant Isodon serra. The five rings in the mol­ecule exhibit the expected cis and trans junctions. The three six-membered rings adopt chair, twist-boat and boat conformations, while two five-membered rings adopt envelope conformations. There are two mol­ecules in the asymmetric unit, related by a non-crystallographic twofold screw axis; the main difference is in the different degrees of distortion of ring B. In the crystal, the mol­ecules are linked by inter­molecular O—H⋯O hydrogen bonds, forming chains along the b axis. PMID:21580740

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

    USDA-ARS?s Scientific Manuscript database

    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...

  14. Synthesis of γ- and δ-lactone natural products by employing a trans-cis isomerization/lactonization strategy.

    PubMed

    Ono, Machiko; Kato, Keisuke; Akita, Hiroyuki

    2013-01-01

    Alkaline hydrolysis of 4-hydroxy- or/and 5-hydroxy-(2E)-alkenoate followed by acid treatment gave the corresponding (2E)-alkenoic acids which were subjected to lactone formation reaction without further purification. The crude acids were treated with 2,4,6-trichlorobenzoyl chloride in pyridine to afford γ-lactone or δ-lactone, respectively, accompanied by trans-cis isomerization. By this procedure, (±)-(4,5)-trans-5-benzyloxy-2-hexen-4-olide (90% overall yield), (S)-5-hydroxy-2-penten-4-olide (86% overall yield), (4S,5R)-5-hydroxy-2-hexen-4-olide (86% overall yield), (4R,5S)-5-hydroxy-2-hexen-4-olide (82% overall yield), (S)-parasorbic acid (58% overall yield) and natural product, (5R,7S)-7-hydroxy-2-octen-5-olide (euscapholide: 20% overall yield) were synthesized.

  15. [Studies on the constituents of Scutellaria species. XV. On the diterpenoid constituents of the leaves of Scutellaria alpina L].

    PubMed

    Miyaichi, Y; Kizu, H; Yamaguchi, Y; Tomimori, T

    1994-04-01

    From the leaves of Scutellaria alpina L., four new neo-clerodane diterpenes (1-4) were isolated. The structures of 1-4 were shown to be (4S)-19-acetoxy-8 beta-hydroxy-6 alpha-benzoyloxy-4,18-epoxy-neo-cleroda-11,13- dien-15,16-olide, (4S)-19-acetoxy-8 beta-hydroxy-6 alpha-tigloyloxy-4,18-epoxy-neo-cleroda-11,13- dien-15,16-olide, (4S, 11S)-11-acetoxy-8 beta,19-dihydroxy-6 alpha-tigloyloxy-4,18-epoxy-neo- clerod-13-en-15,16-olide, and (4S)-19-acetoxy-8 beta-hydroxy-6 alpha, 7 beta-dibenzoyloxy-4,18-epoxy-neo- cleroda-11,13-dien-15,16-olide, respectively, by the chemical and spectral data.

  16. New steroidal lactones and homomonoterpenic glucoside from fruits of Malva sylvestris L.

    PubMed

    Mustafa, Akhlaq; Ali, Mohammed

    2011-01-01

    Phytochemical investigation of the ethanolic extract of defatted fruits of Malva sylvestris Linn. (Malvaceae) led to the isolation of six new steroidal lactones and a homomonoterpenic glucoside along with beta-sitosterol-3-beta-D-glucopyranoside. The structures of new phytoconstituents have been elucidated as cholest-5-en-3a-ol-18(21)-olide (sylvestrosterol A), cholest-9(11)-en-3alpha-ol-18(21)-olide (sylvestrosterol B), cholest-4,6,22-trien-3alpha-ol-18(21)-olide (sylvestrosterol C), 2-methyl-6-methylene-n-decan-2-olyl- 3beta-D-glucopyranoside (malvanoyl glucoside), cholest-7-en-18(21)-olide-3alpha-olyl-3beta-D-glucopyranoside (sylvestrogenin A), cholest-9(11)-en-18(21)-olide-3alpha-olyl-3beta-D-glucopyranoside (sylvestrogenin B) and cholest-5-en-8(21)-olide-3alpha-olyl-3beta-D-glucopyranoside (sylvestrogenin C).The structures of all these phytoconstituents have been established on the basis of spectral data analysis and chemical reactions.

  17. Isolation of two new bioactive sesquiterpene lactone glycosides from the roots of Ixeris dentata.

    PubMed

    Park, SeonJu; Nhiem, Nguyen Xuan; Lee, Taek Hwan; Kim, Nanyoung; Kim, Sun Yeou; Chae, Han-Jung; Kim, Seung Hyun

    2015-10-15

    Two new sesquiterpene lactone glycosides, 3-O-β-d-glucopyranosyl-8-hydroxy-(1,5,6,7,11)-guaia-3,10(14)-dien-12,6-olide (1) and 3-O-β-d-glucopyranosyl-8-(4-hydroxyphenylacetyloxy)-(1.5.6,7)-guaia-3,10(14),11(13)-trien-12,6-olide (2), and 12 known sesquiterpene lactone derivatives (3-14) were isolated from the roots of Ixeris dentata. Their structures were determined by extensive spectroscopic methods including 1D and 2D NMR and MS spectra data. All compounds were tested for their ability to inhibit lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV-2 microglial cell. 3-O-β-d-Glucopyranosyl-8-(4-hydroxyphenylacetyloxy)-(1.5.6,7)-guaia-3,10(14),11(13)-trien-12,6-olide (2) showed the most potent inhibitory activity at a concentration of 20μM.

  18. Sensitized photooxidation of furanoeremophilane with singlet oxygen and their biogenetic relationship.

    PubMed

    Li, Yun-Sen; Wang, Zheng-Tao; Luo, Shi-De; Li, Shao-Shun; Zhu, Da-Yuan

    2006-07-10

    In an attempt to explore the biogenetic relationship of furanoeremophilane derivatives and eremophilan-8alpha,12-olides, produced in Ligularia and their structure-activity relationship, we studied the photosensitized oxidation of furanoeremophilane-type sesquiterpenes. Under the condition of several solvents solution Irradiation with a 200 W incandescent lamp of furanoeremophilan-14beta,6alpha-olide isolated from Ligularia vellerea, in various solutions with methylene blue, rose bengal, toluidine blue and safranine T gave several products. The products were isolated by chromatographic procedure and their structures were elucidated as eremophilan-14beta,6alpha,8alpha,12-diolide derivatives by NMR, IR and MS methods. A reaction mechanism has been proposed.

  19. Attraction of agrilus planipennis fairmaire (Coleoptera: Buprestidae) to a volatile pheromone: effects of release rate, host volatile and trap placement

    USDA-ARS?s Scientific Manuscript database

    Attraction of emerald ash borer, Agrilus planipennis Fairmaire, to a volatile pheromone was demonstrated in three field experiments using baited green sticky traps. A dose-response curve was generated for male A. planipennis to increasing release rates of (3Z)-dodecen-12-olide, (3Z)-lactone, in com...

  20. Novel lanostane and rearranged lanostane-type triterpenoids from Abies sachalinensis - II -.

    PubMed

    Gao, Hui Yuan; Wu, Li Jun; Nakane, Takahisa; Shirota, Osamu; Kuroyanagi, Masonori

    2008-04-01

    In the previous work we reported five A-seco-rearranged lanostane triterpenoids as antibacterial constituents from the ethyl acetate soluble fraction of Abies sachalinensei leaves. In further study on the isolation of constituents from the ethyl acetate soluble fraction, two new rearranged lanostane and lanostane-type triterpenoids (3, 4) and three reported compound (1, 2, 5) were isolated. The structures of new compound 3 and 4 were determined to be 3,4-seco-4(28),6,8(14),24-mariesatetraen-26,23-olide-23-hydroxy-3-oic acid and 3,4-seco-4(28),7,24-lanostatrien-26,23-olide-23-hydroxy-3-oic acid, respectively, by spectral studies on HR-MS, (1)H-NMR, (13)C-NMR, and 2D-NMR spectra. Compound 1 was identified with pindrolactone and its structure was revised as 7,14,22Z,24-mariesatetraen-26,23-olide-3alpha-ol. Structures of 2 and 5 were determined as 7,14,24-mariesatrien-26,23-olide-3alpha,23-diol and 3alpha-hydroxy-7,14,24E-mariesatrien-23-oxo-26-oic acid. Of these compounds, 2, 3 and 4 were obtained as lactol tautomer mixtures at gamma-lactone structures of side chains.

  1. A new antifungal eudesmanolide glycoside isolated from Sphaeranthus indicus Linn. (Family Compositae).

    PubMed

    Mishra, Bhuwan B; Kishore, Navneet; Tiwari, Vinod K

    2016-03-08

    A new antifungal eudesmanolide glycoside 11,13-dihydro-3-O-(β-digitoxopyranose)-7α-hydroxy eudasman-6,12-olide (2) in addition to known compounds 1 and 3, has been isolated from Sphaeranthus indicus Linn. Its structure was determined by spectral analysis (UV, IR, 1D and 2D NMR and mass spectrum).

  2. Putative pheromone for the emerald ash borer, Agrilus planipennis (Coleoptera: Buprestidae)

    USDA-ARS?s Scientific Manuscript database

    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 about 10 times more abundant from females. It was readily sensed by both male and female antennae...

  3. Antimicrobial activity of clerodane diterpenoids from Polyalthia longifolia seeds.

    PubMed

    Marthanda Murthy, M; Subramanyam, M; Hima Bindu, M; Annapurna, J

    2005-06-01

    The diterpenoids 16alpha-hydroxy-cleroda-3,13 (14)-Z-diene-15,16-olide (1) and 16-oxo-cleroda-3, 13(14)-E-diene-15-oic acid (2), isolated from the hexane extract of the seeds of Polyalthia longifolia, demonstrated significant antibacterial and antifungal activities.

  4. 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.

  5. Beckmann rearrangement within the ring C of oleanolic acid lactone: Synthesis, structural study and reaction mechanism analysis

    NASA Astrophysics Data System (ADS)

    Froelich, Anna; Bednarczyk-Cwynar, Barbara; Zaprutko, Lucjusz; Gzella, Andrzej

    2017-05-01

    Synthesis, spectral and X-ray analysis of three compounds, i.e. 3β-acetoxy-12-hydroxyimino-18β-oleanan-28,13β-olide (substrate) and 3β-acetoxy-12-nitrile-12,13-seco-15(14 → 13)-abeoolean-14(27)-en-28,13β-olide and 3β-acetoxy-12-oxo-12a-aza-C-homoolean-13(18)-en-28-oic acid (Beckmann rearrangement reaction products) are described. Structural analysis revealed that the oxime group in the ring C in substrate molecule had an E-configuration. The nitrile product with retained lactone group was a result of major transformations within rings C and D of oleanane skeleton. In lactam product free carboxyl group and a double bond in ring D instead of lactone system were formed in Beckmann rearrangement reaction.

  6. Decalactone production by Yarrowia lipolytica under increased O2 transfer rates.

    PubMed

    Aguedo, M; Gomes, N; Garcia, E Escamilla; Waché, Y; Mota, M; Teixeira, J A; Belo, I

    2005-10-01

    Yarrowia lipolytica converts methyl ricinoleate to gamma-decalactone, a high-value fruity aroma compound. The highest amount of 3-hydroxy-gamma-decalactone produced by the yeast (263 mg l(-1)) occurred by increasing the k(L)a up to 120 h(-1) at atmospheric pressure; above it, its concentration decreased, suggesting a predominance of the activity of 3-hydroxyacyl-CoA dehydrogenase. Cultures were grown under high-pressure, i.e., under increased O(2) solubility, but, although growth was accelerated, gamma-decalactone production decreased. However, by applying 0.5 MPa during growth and biotransformation gave increased concentrations of dec-2-en-4-olide and dec-3-en-4-olide (70 mg l(-1)).

  7. New sesquiterpenoids from Ambrosia artemisiifolia L.

    PubMed

    Ding, Wenbing; Huang, Rui; Zhou, Zhongshi; Li, Youzhi

    2015-03-10

    A new pseudoguaianolide 1 and two new guaiane-type sesquiterpene glucosides 2 and 3, were isolated from the aerial parts of Ambrosia artemisiifolia L together with two known sesquiterpene dilactones 4 and 5. The new compounds were determined on the basis of spectroscopic and chemical methods to be 3β-acetoxy-4β-hydroxy-1α,7α, 10β,11αH-pseudoguaia-12,8β-olide (1), 1β,7β,9β,10β,13αH-guaia-4(5)-en-12,6β-olide 9-O-β-d-glucoside (2) and 4β-hydroxy-1α,5α,7α,9αH-guaia-10(14),11(13)-dien-12-acid 9-O-β-d-glucoside (3). The isolated compounds were evaluated for cytotoxicity against human promyelocytic leukemia HL-60 cell lines in vitro, but were all inactive.

  8. Two new sesquiterpenes from Chloranthus japonicus Sieb.

    PubMed

    Lu, Qiang-Qiang; Shi, Xin-Wei; Zheng, Shao-Jun; Zhou, Jun-Hui; Cui, Xin-Ai; Gao, Jin-Ming

    2016-11-01

    Two new sesquiterpenes, namely, 1β,10β-dihydroxy-eremophil-7(11), 8-dien-12,8-olide (1) and 8,12-epoxy-1β-hydroxyeudesm-3,7,11-trien-9-one (2), together with three known sesquiterpenoids, shizukolidol (3), 4α-hydroxy-5α(H)-8β-methoxy-eudesm-7(11)-en-12,8-olide (4), and neolitacumone B (5), and two known monoterpenes, (3R,4S,6R)-p-menth-1-en-3,6-diol (6) and (R)-p-menth-1-en-4,7-diol (7), were isolated from the whole plant of Chloranthus japonicus Sieb. Their structures were elucidated on the basis of spectroscopic data analysis and comparison with those of related known compounds. Compounds 4-7 were isolated from this plant for the first time.

  9. Cytotoxic effect of triterpenoids from the root bark of Hibiscus syriacus.

    PubMed

    Shi, Li-Shian; Wu, Chao-Hsuan; Yang, Te-Chun; Yao, Chen-Wen; Lin, Hang-Ching; Chang, Wen-Liang

    2014-09-01

    In this study, 4 new triterpenoids-3β- acetoxy-olean-11-en,28,13β-olide (1), 3β- acetoxy-11α,12α-epoxy-olean-28,13β-olide (2), 19α-epi-betulin (3), and 20, 28-epoxy-17β,19β-lupan-3β-ol (4)-and 12 known compounds, were isolated from the root bark of Hibiscus syriacus L. by using acetone extraction. Their structures were characterized by extensive spectroscopic analysis. To investigate cytotoxicity, A549 human lung cancer cells were exposed to the extract and the compounds identified from it. Significantly reduced cell viability was observed with betulin-3-caffeate (12) (IC50, 4.3 μM). The results of this study indicate that betulin-3-caffeate (12) identified from H. syriacus L. may warrant further investigation for potential as anticancer therapies. Copyright © 2014 Elsevier B.V. All rights reserved.

  10. 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.

  11. Permeable Reactive Barriers: Lessons Learned/New Directions

    DTIC Science & Technology

    2005-02-01

    treatment was not clear. It is possible that the nitrate was reduced to ammonia abiotically or that some microbially mediated denitrification within the...industrial needs. For consideration in a PRB design, the zeolitic mineral clinoptilolite olid solution composition [(Ca, Mg, Na2, K2) (Al2Si10O24...2005 An example pilot program evaluating the use of the zeolite clinoptilolite to remove Sr-90 from groundwater was initiated in 1999 at the West

  12. Investigation of Sheath Phenomena in Electronegative Glow Discharges.

    DTIC Science & Technology

    1985-04-01

    the heavy ,olid line refers to the ground state of the neutrl molecuie XY. The :uclear sepration oscillates then between P, ard R2. The thinner "ui...curve of the neutral molecule by an amount of energy equal to the electron affinity (E a) of atom Y. The solid region represents the range over which the...can also enhance the cross bection for dissociative attachment due to the centrifugal stretching occurriny in the excited states, but in a less

  13. 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.

  14. A new sesquiterpene lactone glucoside with inhibitory effect on K562 cells from Ixeris sonchifolia (Bge) Hance.

    PubMed

    He, W-F; Xu, B-B; Pan, J-C; Lu, J-C; Song, S-J; Xu, S-X

    2006-09-01

    A new minor sesquiterpene lactone glucoside, ixerin ZA (1), together with 16 known compounds, were isolated from the whole plants of Ixeris sonchifolia (Bge) Hance. The structure of 1 was elucidated as 1(10),3,11(13)-guaiatriene-12,6-olide-2-one-3-O-[6'-(p-metheoxyphenylacetyl)]-beta-glucopyranoside on the basis of spectroscopic and chemical evidence. Compound 1 exhibited an inhibitory effect on K562 cells.

  15. Compliant Material Coating Response to a Turbulent Boundary Layer,

    DTIC Science & Technology

    1982-05-01

    this we apply the Ash code model Honte Carlo pres- sure simulations.13 We consider a flat plate, with zero pressure gradient immersed immediately...litude and circular frequency, respectively. Both sets of calculations were made for zero immersion depth ocean surface (Z • 0) motion. The äolid...when subjected to ran- dom turbulent loads. The non-linear frequency dependence of the shear modulus for one of the materials, " plastisol " (PVC) is

  16. The Environmental Assessment and Management (TEAM) Guide: New Hampshire Supplement

    DTIC Science & Technology

    2010-03-01

    ASTM - the American Society for Testing and Materials (NHCAR Env-A 101). • Automotive - that which pertains to roadway vehicles with...1204.03) [Revised March 2004]. • Coal - all s olid fuels cl assified an an thracite, bituminous, lig nite, o r s ubbituminous a ccording to th e ASTM ...Standard Specification for Classification of Coals by Rank, ASTM D 388-77, coal refuse, and petroleum coke. The term includes coal-derived synthetic

  17. Achillinin A, a cytotoxic guaianolide from the flower of Yarrow, Achillea millefolium.

    PubMed

    Li, Yong; Zhang, Man-Li; Cong, Bin; Wang, Si-Ming; Dong, Mei; Sauriol, Françoise; Huo, Chang-Hong; Shi, Qing-Wen; Gu, Yu-Cheng; Kiyota, Hiromasa

    2011-01-01

    Achillinin A (2β,3β-epoxy-1α,4β,10α-trihydroxyguai-11(13)-en-12,6α-olide, 1), a new guaianolide isolated from the flower of Achillea millefolium, exhibited potential antiproliferative activity to A549, RERF-LC-kj and QG-90 cells with 50% inhibitory concentration (IC(50)) values of 5.8, 10 and 0.31 µM, respectively.

  18. 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.

  19. 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

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

    PubMed

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

    2013-02-05

    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.

  1. Anticancer activity of sesquiterpene lactone from plant food (Carpesium rosulatum) in human cancer cell lines.

    PubMed

    Moon, Hyung-In; Zee, Okpyo

    2011-03-01

    In the search for anticancer compounds against human cancer cells (A549, SK-OV-3, SK-MEL-2, XF498, HCT15), it was found that the chloroform extracts obtained from the whole plant food of Carpesium rosulatum MlQ exhibited significant anticancer activity. The structures and stereochemistry of these compounds were established on the basis of analysis of spectra including melting point, [α](D)(25), infrared, ultraviolet, electron ionization mass spectrometry, mass spectrometry, (1)H-nuclear magnetic resonance, (13)C-nuclear magnetic resonance and some chemical transformations as follows: compound 1, 4β,10α-dihydroxy-guaia-8α,12-olide; compound 2, 4β,10α-dihydroxy-1(2),11(13)-guaiadien-8α,12-olide; and compound 3, 3β,8β-dihydroxy-1α,5α-guaian-10(14)-ene-6α,12-olide. Anticancer activity of compounds obtained from C. rosulatum on five tumor cells line was evaluated by sulforhodamine B methods. Compound 2 was significantly effective on the five human tumor cell lines.

  2. Cytotoxic and ACAT-inhibitory sesquiterpene lactones from the root of Ixeris dentata forma albiflora.

    PubMed

    Ahn, Eun-Mi; Bang, Myun-Ho; Song, Myoung-Chong; Park, Mi-Hyun; Kim, Hwa-Young; Kwon, Byoung-Mog; Baek, Nam-In

    2006-11-01

    Ixeris dentata forma albiflora was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and H2O. Eight sesquiterpenes were isolated through repeated silica gel and octadecyl silica gel (C18, ODS) column chromatography of the EtOAc and n-BuOH fractions. Physicochemical analysis using NMR, MS and IR revealed the chemical structures of the sesquiterpenes, which were zaluzanin (1), 9a-hydroxyguaian-4(15),10(14),11(13)-triene-6,12-olide (2), 3beta-O-beta-D-glucopyranosyl-8beta-hydroxyguaian-4(15),10(14)-diene-6,12-olide (3), 3-O-beta-D-glucopyranosyl-8beta-hydroxyguauan-10(14)-ene-6,12-olide (4), ixerin M (5), glucozaluzanin C (6), crepiside I (7), and ixerin D (8). This is the first time that these sesquiterpene lactones have been isolated from this plant. Compounds 1, 2 and 7 revealed relatively high cytotoxicities on human colon carcinoma cell and lung adenocarcinoma cell, while compounds 5 and 7 showed acyl-CoA: cholesterol acyltransferase (ACAT) inhibitory activity.

  3. Identification, synthesis and mass spectrometry of a macrolide from the African reed frog Hyperolius cinnamomeoventris

    PubMed Central

    Menke, Markus; Peram, Pardha Saradhi; Starnberger, Iris; Hödl, Walter; Jongsma, Gregory FM; Blackburn, David C; Rödel, Mark-Oliver; Vences, Miguel

    2016-01-01

    The contents of the gular glands of the male African reed frog Hyperolius cinnamomeoventris consist of a mixture of aliphatic macrolides and sesquiterpenes. While the known macrolide gephyromantolide A was readily identified, the structure of another major component was suggested to be a tetradecen-13-olide. The synthesis of the two candidate compounds (Z)-5- and (Z)-9-tetradecen-13-olide revealed the former to be the naturally occurring compound. The synthesis used ring-closing metathesis as key step. While the Hoveyda–Grubbs catalyst furnished a broad range of isomeric products, the (Z)-selective Grubbs catalyst lead to pure (Z)-products. Analysis by chiral GC revealed the natural frog compound to be (5Z,13S)-5-tetradecen-13-olide (1). This compound is also present in the secretion of other hyperoliid frogs as well as in femoral glands of male mantellid frogs such as Spinomantis aglavei. The mass spectra of the synthesized macrolides as well as their rearranged isomers obtained during ring-closing metathesis showed that it is possible to assign the location of the double bond in an unsaturated macrolide on the basis of its EI mass spectrum. The occurrence of characteristic ions can be explained by the fragmentation pathway proposed in the article. In contrast, the localization of a double bond in many aliphatic open-chain compounds like alkenes, alcohols or acetates, important structural classes of pheromones, is usually not possible from an EI mass spectrum. In the article, we present the synthesis and for the first time elucidate the structure of macrolides from the frog family Hyperoliidae. PMID:28144343

  4. 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.

  5. 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

  6. Inuloxins A-D, phytotoxic bi-and tri-cyclic sesquiterpene lactones produced by Inula viscosa: potential for broomrapes and field dodder management.

    PubMed

    Andolfi, Anna; Zermane, Nadjia; Cimmino, Alessio; Avolio, Fabiana; Boari, Angela; Vurro, Maurizio; Evidente, Antonio

    2013-02-01

    Four phytotoxic bi- and tri-cyclic sesquiterpene lactones, named inuloxins A-D, were isolated together with the known α-costic acid, from the aerial parts of Inula viscosa (family Asteraceae), a widespread Mediterranean plant well known for its content of pharmacologically active metabolites. The structures of inuloxins A-D were established by spectroscopic and chemical methods and determined to be: (4E,7R*,8R*,10S*)-3-oxo-germacra-4,11(13)-dien-8β-12-olide (A), its 11,13-dihydro analogue (B), (5R*,7R*,8R*,10R*)-1,15-methylene-5β-hydroxy-eudesm-1(15),11(13)-dien-8β-12-olide (C), and (7R*,8R*)-1,4-dimethyl-4-hydroxy-secoeudesm-5(10),11(13)-dien-8β-12-olide (D). The S absolute stereochemistry at C-5 of 5-hydroxyhexan-2-yl side chain of inuloxin D was assigned by applying an advanced Mosher's method. The phytotoxic activity of inuloxins A-D, that of the diazo and monoacetyl derivatives (of inuloxin A and C, resply), as well as that of α-costic acid was evaluated against two parasitic plant species, i.e. crenate broomrape (Orobanche crenata) and field dodder (Cuscuta campestris). Inuloxins A, C and D were the most active on both parasites and caused up to 100% inhibition of the seed germination. Inuloxin B was less active on Cuscuta and completely inactive against Orobanche. The main metabolite α-costic acid had a suppressive effect on the dodder seed germination but had a stimulating action on the broomrape seed germination. These preliminary results allowed to suppose some structure-activity relationships.

  7. Screening of Thai medicinal plant extracts and their active constituents for in vitro antimalarial activity.

    PubMed

    Ichino, C; Soonthornchareonnon, N; Chuakul, W; Kiyohara, H; Ishiyama, A; Sekiguchi, H; Namatame, M; Otoguro, K; Omura, S; Yamada, H

    2006-04-01

    To discover antimalarial substances from plants cultivated in Thailand 80%-EtOH extracts from selected plants were screened for in vitro antimalarial activity against the drug resistant K1 strain of Plasmodium falciparum. In total, 86 Thai medicinal plant samples representing 48 species from 35 genera in 16 families were screened and two species (Polyalthia viridis and Goniothalamus marcanii) were found to show notable antimalarial activity (IC50: 10.0 and 6.3 microg/mL). Marcanine A and 16-hydroxycleroda-3,13(14)Z-dien-15,16-olide were identified as the respective major active constituents in P. viridis and G. marcanii, respectively.

  8. 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).

  9. Environmental Inventory Report. East St. Louis and Vicinity, Cahokia Canal Drainage Area, Madison and St. Clair Counties, Illinois. Volume 5.

    DTIC Science & Technology

    1981-05-01

    olid It neceeaw ad Identify by block nmbi) Water and Sediment Quality Terrestial Communities Air pollution Cultural Studies Noise pollution ...SEDIMENT QUALITY -ThomeAAon VOLUME 2- ADVERSE ENVIRONMENTAL FACTORS I’ll AIR POLLUTION -Thoxuton IV NOISE POLLUTION -Thonton g VOLUME 3 BIOLOGICAL ELEMENTS V...C-4 I.. ++ +L.+ CL. 6e 0. m ) 0 LA% 0- e 4) - grO 4j* - M ~ 04 a% -T 4.-~ .D -T N. eq 0 fl- 0oL.C - 0 t- c 04 V mV C- 4N 4-i 4-j 04- 04- -T M -- T

  10. Spasmolytic constituents from Eucalyptus camaldulensis var. obtusa leaves.

    PubMed

    Begum, S; Farhat, F; Sultana, I; Siddiqui, B S; Shaheen, F; Gilani, A H

    2000-09-01

    Phytochemical studies on the leaves of Eucalyptus camaldulensis var. obtusa have resulted in the isolation of a new triterpenoid camaldulin (3beta-formyloxyurs-11-en-28,13beta-olide) (1) along with ursolic acid lactone acetate (2), ursolic acid lactone (3), betulinic acid (4), and beta-sitosterol 3-O-beta-D-glucopyranoside (5). The structures were assigned on the basis of 1D and 2D NMR studies. Compounds 1-3 were tested for spasmolytic activity and were found to possess calcium antagonist activity.

  11. Two new terpenoids from endophytic fungus Periconia sp. F-31.

    PubMed

    Ge, Han-Lin; Zhang, De-Wu; Li, Li; Xie, Dan; Zou, Jian-Hua; Si, Yi-Kang; Dai, Jungui

    2011-01-01

    Two new terpenoids, (+)-(3S,6S,7R,8S)-periconone A (1) and (-)-(1R,4R,6S,7S)-2-caren-4,8-olide (2), have been isolated from an endophytic fungus Periconia sp., which was collected from the plant Annona muricata. Their structures were elucidated on the basis of extensive spectroscopic analyses. In the in vitro assays, the two compounds showed low cytotoxic activities against six human tumor cell lines (HCT-8, Bel-7402, BGC-823, A549, A2780 and MCF-7) with IC(50)>10(-5) M.

  12. 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.

  13. Two new triterpenoids from Photinia serrulata.

    PubMed

    Song, Yaling; Wang, Yuehu; Lu, Qing; Gao, Jinming; Bi, Minggang; Cheng, Yongxian

    2007-12-20

    Two new triterpenoids, 2alpha,3beta,11alpha,13beta-tetrahydroxy-12-ketooleanan-28-oic acid(1) and 3beta-hydroxy-12-keto-9(11)-ursen-28,13beta-olide (2) were isolated from the leaves ofPhotinia serrulata. Their structures were identified by spectral methods. Compounds 1 and2 were assessed for cytotoxic activity against three human tumor cell lines (A-549, HCT-8,and BEL-7402), and they showed no cytotoxic effects at concentrations up to 5microg/mL.

  14. Secondary metabolites from Senecio burtonii (Compositae).

    PubMed

    Ndom, J C; Mbafor, J T; Azebaze, A G B; Vardamides, J C; Kakam, Z; Kamdem, A F W; Deville, A; Ngando, T M; Fomum, Z T

    2006-04-01

    A cacalolide derivative named 4alpha-[2'-hydroxymethylacryloxy]-1beta-hydroxy-14-(5-->6) abeo eremophilan-12,8-olide and a shikimic acid derivative named (3'E)-(1alpha)-3-hydroxymethyl-4beta,5alpha-dimethoxycyclohex-2-enyloctadec-3'-enoate along with three known compounds, octacosan-1-ol, 3beta-hydroxyolean-12-en-28-oic acid and 3beta-acetoxyolean-12-en-28-oic acid were isolated from Senecio burtonii. Their structures and relative configurations were established on the basis of spectroscopic analysis.

  15. Four new Sesquiterpenoids from Sphaeranthus indicus.

    PubMed

    Emani, Lakshma Reddy; Ravada, Suryachandra Rao; Garaga, Machi Raju; Meka, Bharani; Golakoti, Trimurtulu

    2017-11-01

    Isolation and characterisation of two new eudesmanolides, 5α-hydroperoxy-7α-hydroxy-isosphaerantholide (1) and (11α,13-dihydro-7α-hydroxyfrullanolide-13-yl)-adenine (2) from the flower heads of Sphaeranthus indicus are described. In addition, 5α-hydroxy-isosphaerantholide (3) and 11α,13-dihydro-eudesman-3,5,7-triene-6α-12-olide (4) are reported first time as a metabolite of S. indicus and as a natural product, respectively. The structures of these compounds were established from rigorous analysis of their high-resolution mass, IR, UV, (1)H NMR, (13)C NMR and 2D NMR spectral data.

  16. Alkaloids and Sesquiterpenes from the South China Sea Gorgonian Echinogorgia pseudossapo

    PubMed Central

    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. PMID:22163197

  17. An Application of the Theory of Materials with Variable Bonding to Solid Propellant.

    DTIC Science & Technology

    1979-06-01

    states as the corresponding sol utions of an ordinary differential equation . A, 3.? ba~ ic Structure Let an open neiqhhourhood 0 of unity in the s t r ic...n, P., Ordinary Di fferential Equations , John W iley & Sons , 1973. 3 Co l eman , B. D., & W . No l l, “Foundation s of Linear Viscoelasticity ,” Rev...COOKE‘~...~~Directc~~.$’olid Rock ivisi ~9~1I TO ALL RECIPIENTS OF AFRPL-TR-78-37 ERRATA On Page 17, the line following Equation (5,3) is incorrect. This

  18. Two new sesquiterpene lactones from Montanoa tomentosa ssp. microcephala.

    PubMed

    Braca, A; Cioffi, G; Morelli, I; Venturella, F; Pizza, C; De Tommasi, N

    2001-11-01

    Two new sesquiterpene lactones: 8alpha-(4'-acetoxymethacryloyloxy)-3alpha,9beta-dihydroxy-1(10)E,4Z,11(13)-germacratrien-12,6alpha-olide (1) and 8alpha-(2'E)-(2'-acetoxymethyl-2'-butenoyloxy)-3alpha,9beta-dihydroxy-1(10)E,4Z,11(13)-germacratrien-12,6alphaolide (2), together with the known zoapatanolide A were isolated from the aerial parts of Montanoa tomentosa Cerv. in La Llave et Lex ssp. microcephala (Sch. Bip. In K. Koch) V.A. Funk (Asteraceae). The structures of all compounds were established on the basis of 1D, 2D NMR, and EIMS analysis.

  19. Identification and synthesis of macrolide pheromones of the grain beetle Oryzaephilus surinamensis and the frog Spinomantis aglavei.

    PubMed

    Hötling, Susann; Haberlag, Birte; Tamm, Matthias; Collatz, Jana; Mack, Patrick; Steidle, Johannes L M; Vences, Miguel; Schulz, Stefan

    2014-03-10

    Macrolide lactones, the so called cucujolides derived from unsaturated fatty acids, are aggregation pheromones of cucujid grain beetles. Thirty years ago, Oehlschlarger et al. showed that (3Z,6Z)-dodeca-3,6-dien-11-olide (4) and the respective 12-olide (7) attract the sawtoothed grain beetle Oryzaephilus surinamensis, whereas (5Z,8Z,13R)-tetradeca-5,8-dien-13-olide (5) increases the response synergistically. The frass of this beetle is attractive for its parasitoid Cephalonomia tarsalis, which potentially can be used for pest control. A GC/MS analysis of attractive frass showed the presence of 5, together with an unknown isomer. Cucujolide V was tentatively identified also in the femoral glands, pheromone-releasing structures, of the Madagascan mantelline frog Spinomantis aglavei. Therefore, a new route to synthesize doubly unsaturated macrolides allowing the flexible attachment of the side chain was developed. A straightforward method to obtain Z configured macrolides involves ring-closing alkyne metathesis (RCAM) followed by Lindlar-catalyzed hydrogenation. This methodology was extended to homoconjugated diene macrolides by using RCAM after introduction of one Z configured double bond in the precursor by Wittig reaction. A tungsten benzylidyne complex was used as the catalyst in the RCAM reaction, which afforded the products in high yield at room temperature. With the synthetic material at hand, the unknown isomer was identified as the new natural product (5Z,8Z,12R)-tetradeca-5,8-dien-12-olide, cucujolide X (8). Furthermore, the route also allowed the synthesis of cucujolide V in good yield. The natural products were identified by the synthesis of enantiomerically pure or enriched material and gas chromatography on chiral phases. The new macrolide (R)-8 proved to be biologically active, attracting female O. surinamensis, but no males. The synthetic material allowed the identification of (R)-5 in both the beetle and the frog. © 2014 WILEY

  20. IR, VCD, 1H and 13C NMR experimental and theoretical studies of a natural guaianolide: Unambiguous determination of its absolute configuration

    NASA Astrophysics Data System (ADS)

    Bercion, Sylvie; Buffeteau, Thierry; Lespade, Laure; Martin, Marie-Anna Couppe deK.

    2006-06-01

    7,10-Epoxy -1,5-guaia-3, 11-dien-8, 12-olide has been isolated from dried leaves of Hedyosmum arborescens Swartz. The structure, vibrational frequencies, infrared and VCD intensities, NMR 1H and 13C spectra have been calculated by the density functional theory (DFT) method at the B3LYP/6-31+G(d,p) levels for four stereoisomers of this natural guaianolide. This study shows that the comparison of the experimental and calculated 1H and 13C NMR spectra allows the determination of the most favorable diastereoisomers but is not sufficient to access to the absolute configuration of the 7,10-epoxy guaianolide since the two remaining enantiomers possess the same NMR spectra. The absolute configuration of this natural compound can be unambiguously established only by the comparison of the calculated and experimental VCD spectra. Indeed, a very good agreement between experimental and theoretical VCD spectra was obtained in the mid-infrared range for the 7 S, 10 R-epoxy-1 R,5 R-guaia-3,11-dien-8 S,12-olide stereoisomer.

  1. 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.

  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. Optical lock-in detection imaging microscopy for contrast-enhanced imaging in living cells.

    PubMed

    Marriott, Gerard; Mao, Shu; Sakata, Tomoyo; Ran, Jing; Jackson, David K; Petchprayoon, Chutima; Gomez, Timothy J; Warp, Erica; Tulyathan, Orapim; Aaron, Holly L; Isacoff, Ehud Y; Yan, Yuling

    2008-11-18

    One of the limitations on imaging fluorescent proteins within living cells is that they are usually present in small numbers and need to be detected over a large background. We have developed the means to isolate specific fluorescence signals from background by using lock-in detection of the modulated fluorescence of a class of optical probe termed "optical switches." This optical lock-in detection (OLID) approach involves modulating the fluorescence emission of the probe through deterministic, optical control of its fluorescent and nonfluorescent states, and subsequently applying a lock-in detection method to isolate the modulated signal of interest from nonmodulated background signals. Cross-correlation analysis provides a measure of correlation between the total fluorescence emission within single pixels of an image detected over several cycles of optical switching and a reference waveform detected within the same image over the same switching cycles. This approach to imaging provides a means to selectively detect the emission from optical switch probes among a larger population of conventional fluorescent probes and is compatible with conventional microscopes. OLID using nitrospirobenzopyran-based probes and the genetically encoded Dronpa fluorescent protein are shown to generate high-contrast images of specific structures and proteins in labeled cells in cultured and explanted neurons and in live Xenopus embryos and zebrafish larvae.

  4. 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

  5. Optical lock-in detection imaging microscopy for contrast-enhanced imaging in living cells

    PubMed Central

    Marriott, Gerard; Mao, Shu; Sakata, Tomoyo; Ran, Jing; Jackson, David K.; Petchprayoon, Chutima; Gomez, Timothy J.; Warp, Erica; Tulyathan, Orapim; Aaron, Holly L.; Isacoff, Ehud Y.; Yan, Yuling

    2008-01-01

    One of the limitations on imaging fluorescent proteins within living cells is that they are usually present in small numbers and need to be detected over a large background. We have developed the means to isolate specific fluorescence signals from background by using lock-in detection of the modulated fluorescence of a class of optical probe termed “optical switches.” This optical lock-in detection (OLID) approach involves modulating the fluorescence emission of the probe through deterministic, optical control of its fluorescent and nonfluorescent states, and subsequently applying a lock-in detection method to isolate the modulated signal of interest from nonmodulated background signals. Cross-correlation analysis provides a measure of correlation between the total fluorescence emission within single pixels of an image detected over several cycles of optical switching and a reference waveform detected within the same image over the same switching cycles. This approach to imaging provides a means to selectively detect the emission from optical switch probes among a larger population of conventional fluorescent probes and is compatible with conventional microscopes. OLID using nitrospirobenzopyran-based probes and the genetically encoded Dronpa fluorescent protein are shown to generate high-contrast images of specific structures and proteins in labeled cells in cultured and explanted neurons and in live Xenopus embryos and zebrafish larvae. PMID:19004775

  6. Two new aliphatic lactones from the fruits of Coriandrum sativum L.

    PubMed Central

    2012-01-01

    Background The present paper describes the isolation and characterization of two new aliphatic δ-lactones along with three glycerides and n-nonadecanyl cetoleate from the fruits of Coriandrum sativum L. (Apiaceae). The structures of all the isolated phytoconstituents have been established on the basis of spectral data analysis and chemical reactions. Results Phytochemical investigation of the methanolic extract of C. sativum L. (Apiaceae) fruits resulted in the isolation of two new aliphatic δ-lactones characterized as 2α-n-heptatriacont-(Z)-3-en-1,5-olide (1) (coriander lactone) and 2α-n-tetracont-(Z,Z)-3,26-dien-18α-ol-1,5-olide (2) (hydroxy coriander lactone) together with glyceryl-1,2-dioctadec-9,12-dienoate-3-octadec-9-enoate (3); glyceryl-1,2,3-trioctadecanoate (4); n-nonadecanyl-n-docos-11-enoate (5) and oleiyl glucoside (6). Conclusions Phytochemical investigation of the methanolic extract of C. sativum gave coriander lactone and hydroxy coriander lactone as the new phytoconstituents. PMID:22800677

  7. 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.

  8. A new triterpene and protective effect of Periploca somaliensis Browicz fruits against CCl₄-induced injury on human hepatoma cell line (Huh7).

    PubMed

    Abdel-Monem, Azza R; Kandil, Zeinab A; Abdel-Naim, Ashraf B; Abdel-Sattar, Essam

    2015-01-01

    The potential hepatoprotective effect of the methanolic extract of Periploca somaliensis Browicz fruits, its different fractions (n-hexane, chloroform and n-butanol) and the major isolated compound ursolic acid was evaluated using the human hepatoma cell line (Huh7) based on the changes in the activity of aspartate aminotransferase, alanine transaminase, glutathione and superoxide dismutase. Each sample was tested at three different concentrations (1000, 100 and 10 μg/mL). All tested samples exhibited a potent concentration-independent cytoprotective effect relative to silymarin as a reference standard. Chromatographic fractionation of the chloroform-soluble fraction of the methanol extract of P. somaliensis Browicz fruits afforded two known triterpenes, namely ursolic acid, and 11α,12α-epoxy-3β-hydroxy-olean-13β,28-olide, and a newly discovered one, namely 3β-hydroxy-urs-11-en-13β,28-olide. The structures of the isolated compounds were elucidated by the analysis of 1D and 2D NMR spectral data.

  9. Protein tyrosine phosphatase 1B inhibitory activities of ursane- and lupane-type triterpenes from Sorbus pohuashanensis.

    PubMed

    Li, Dongxia; Li, Wei; Higai, Koji; Koike, Kazuo

    2014-04-01

    Protein tyrosine phosphatase 1B (PTP1B) is a non-transmembrane protein tyrosine phosphatase, and has received much attention as a molecular target for the treatment of insulin resistance diseases because of its critical roles in negatively regulating insulin- and leptin-signaling cascades. Six ursane-type triterpenes, 3β-acetoxy-urs-12-ene-28-oic acid (1), pomolic acid-3β-acetate (2), pomolic acid (3), ursolaldehyde (4), euscaphic acid (5) and 3β-acetoxy-urs-11-en-28,13-olide (6), and a lupane-type triterpene, betulinic acid (7), from the fruits of Sorbus pohuashanensis, exhibited significant PTP1B inhibitory activity, with IC50 values ranging from 3.5 to 54.8 μM. Kinetics analyses revealed that compounds 2, 3, and 7 are non-competitive PTP1B inhibitors, and compounds 1 and 6 are mixed-type PTP1B inhibitors.

  10. 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.

  11. Bioinspired Asymmetric Synthesis of Hispidanin A.

    PubMed

    Li, Fuzhuo; Tu, Qian; Chen, Sijia; Zhu, Lei; Lan, Yu; Gong, Jianxian; Yang, Zhen

    2017-05-15

    The first enantiospecific synthesis of hispidanin A (4), a dimeric diterpenoid from the rhizomes of Isodon hispida, was achieved with a longest linear sequence of 12 steps in 6.5 % overall yield. A key component is the use of the abundant and naturally occurring diterpenoids (+)-sclareolide and (+)-sclareol as starting materials, which enables the gram-scale preparation of the key intermediates totarane (1) and s-trans-12E,14-labdadien-20,8β-olide (2). Subsequently a thermal or an erbium-catalyzed intermolecular Diels-Alder reaction of totarane (1) with labdadienolide (2) provide convergent and rapid access to the natural product hispidanin A (4). The synthetic studies have offered significant impetus for the efficient construction of these architecturally complex natural products. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  12. A nor-diterpene from Salvia sahendica leaves.

    PubMed

    Mofidi Tabatabaei, Sahar; Salehi, Peyman; Moridi Farimani, Mahdi; Neuburger, Markus; De Mieri, Maria; Hamburger, Matthias; Nejad-Ebrahimi, Samad

    2017-08-01

    Phytochemical investigation of n-hexane extract of Salvia sahendica by normal phase column chromatography resulted in the isolation of six compounds. Structures were established by 1D and 2D NMR spectroscopy, and HRMS, as a new norditerpene 1, and known terpenoids, sclareol (2), oleanolic acid (3), β-sitosterol (4), salvigenin (5) and 3α-hydroxy-11α,12α-epoxyoleanan-28,13β-olide (6). The absolute configuration of 1 was confirmed by a combination of X-ray single crystal analysis and electronic circular dichroism spectroscopy. In vitro cytotoxic activity on breast cancer cell line (MDA-MB-231) and also the antimicrobial activity of the pure compounds were tested against Staphylococcus aureus, Bacilus cereus and Escherichia coli.

  13. A new labdane diterpene from the flowers of Solidago canadensis.

    PubMed

    Bradette-Hébert, Marie-Eve; Legault, Jean; Lavoie, Serge; Pichette, André

    2008-01-01

    A new labdane diterpene, 9alpha,16xi-dihydroxy-6-oxo-7,13-labdadien-15,16-olide (solicanolide, 1) and six known compounds identified as quercetin (2), 3-O-caffeoylquinic acid (3, neochlorogenic acid), 5-O-caffeoylquinic acid (4, chlorogenic acid), 4,5-di-O-caffeoylquinic acid (5), 3,5-di-O-caffeoylquinic acid (6) and 3,4-di-O-caffeoylquinic acid (7) were isolated from the flowers of Solidago canadensis. To our knowledge, compound 7 was isolated for the first time in S. canadensis. This work describes the isolation of compounds 1-7 and the structure elucidation of a new compound identified as compound 1. Solicanolide (1) showed cytotoxic activity against A549 (IC(50): 13+/-2 microM), DLD-1 (IC(50): 26+/-2 microM) and WS1 (IC(50): 17+/-1 microM) cell lines.

  14. 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.

  15. Analysis and Calculation by Integral Methods of Laminar Compressible Boundary Layer with Heat Transfer and with and Without Pressure Gradient

    DTIC Science & Technology

    1955-01-01

    hI ’Uher an I ’lI 5 l’i it ’ ll t/, Iis I 4’(l i0o l ir o ll th dllt’ \\\\ Ill’ Iv trl’ sf1411 e111/ 41. ’ developed. Ths111 rflclto 1i’e tilt hidt...551)v LAIABO iRLAYEoin ANALYS;ISvo olid Ir conrariit liiimer, a cmmetiiR Vait ofra eq *11 viilli v iate! 1 K i nnd -doc (re .3) 1111 q l~~ofa sprateiof...where44 seq(jll(’h 1. ThuIllS-. o14Jpj41i4g cquat11ion. 40l 4)1 14414 37 14fil q/ (A- 1)! opi,, :;S) i l( 1114’ lli lo1414141 oIf Ilvilt- Ir lsfl rate14I

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

    PubMed

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

    2015-06-01

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

  17. A new ent-clerodane diterpenoid from Crassocephalum bauchiense Huch. (Asteraceae).

    PubMed

    Tchinda, Alembert T; Mouokeu, Simplice R; Ngono, Rosalie A N; Ebelle, Madeleine R E; Mokale, Aristide L K; Nono, Diane K; Frédérich, Michel

    2015-01-01

    A phytochemical investigation of the whole plant of Crassocephalum bauchiense Huch. resulted in the isolation of a new clerodane diterpenoid, ent-2β,18,19-trihydroxycleroda-3,13-dien-16,15-olide (1), together with two known flavonoids 3',5-dihydroxy-4',5',6,7,8-pentamethoxyflavone (2) and 4',5-dihydroxy-3',5',6,7,8-pentamethoxyflavone (3). The compounds were tested against the chloroquine-sensitive 3D7 strain of Plasmodium falciparum. Compound 2 showed weak activity (IC50 = 10.1 g/mL) whilst compounds 1 and 3 were inactive. The structures of the compounds were elucidated by using detailed spectral analyses, especially (1)H and (13)C NMR, (1)H-(1)H COSY, NOESY, HMBC and HR-ESI-MS.

  18. 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

  19. Acylperoxylated and seco-mexicanolides from stems of Khaya anthotheca.

    PubMed

    Ferreira, Izabel C Piloto; Cortez, Diógenes A Garcia; das G F da Silva, M Fátima; Fo, Edson Rodrigues; Vieira, Paulo C; Fernandes, João B

    2005-03-01

    The stems of Khaya anthotheca yielded two new limonoids, which were identified on the basis of spectroscopic analysis as 1alpha,8alpha-oxido-3beta-acetoxy-2alpha-acylperoxy-1alpha,14alpha-dihydroxy-[3.3.1(10,2)]-bicyclomeliac-7,19-olide (3) and 3-acetoxy-8,14-dien-8,30-seco-khayalactone (4). Methyl 1alpha,2beta,3alpha,6,8alpha,14beta-hexahydroxy-[4.2.1(10,30).1(1,4)]-tricyclomeliac-7-oate, scopoletin, and 3-O-beta-D-glucopyranosylsitosterol were also isolated. The limonoids were of little value to clarify the basis of the nonresistance against Hypsipyla grandella.

  20. Cytotoxic and Anti-Inflammatory Metabolites from the Soft Coral Scleronephthya gracillimum

    PubMed Central

    Fang, Hui-Yu; Hsu, Chi-Hsin; Chao, Chih-Hua; Wen, Zhi-Hong; Wu, Yang-Chang; Dai, Chang-Feng; Sheu, Jyh-Horng

    2013-01-01

    Five new pregnane-type steroids, sclerosteroids J–N (1–5), and a diterpenoid with a new chemotype 3-methyl-5-(10′-acetoxy-2′,6′,10′-trimethylundecyl)-2-penten-5-olide (6), have been isolated from a soft coral Scleronephthya gracillimum. The structures of the metabolites were determined by extensive spectroscopic analysis. Compound 4 exhibited cytotoxicity against HepG2, A549, and MDA-MB-231 cancer cell lines. Furthermore, steroids 2 and 4 were found to significantly inhibit the accumulation of the pro-inflammatory iNOS protein, and 1, 2, 4 and 5 could effectively reduce the accumulation of COX-2 protein in LPS-stimulated RAW264.7 macrophage cells. PMID:23760015

  1. Diterpene glycosides from the seeds of Pharbitis nil.

    PubMed

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

    2009-06-01

    Six new ent-kaurane diterpene glycosides, pharbosides A-F (1-6), and a new ent-gibbane diterpene glycoside, pharboside G (7), together with three known ent-kaurane diterpenoids, 7beta,16beta,17-trihydroxy-ent-kauran-6alpha,19-olide (8), 6beta,7beta,16alpha,17-tetrahydroxy-ent-kauranoic acid (9), and 6beta,7beta,16beta,17-tetrahydroxy-ent-kauranoic acid (10), were isolated from an ethanolic extract of the seeds of Pharbitis nil. The structures of the new compounds were determined by spectroscopic methods including 1D and 2D NMR analysis. The absolute configurations of the compounds were clarified by CD spectroscopic studies. Full NMR data assignments of the three known compounds (8-10) are reported. The isolated compounds were evaluated for their cytotoxic activities against four human cancer cell lines.

  2. Quassinoids from Eurycoma longifolia.

    PubMed

    Miyake, Katsunori; Tezuka, Yasuhiro; Awale, Suresh; Li, Feng; Kadota, Shigetoshi

    2009-12-01

    Ten new structurally diverse quassinoids (1-10) and 14 known compounds were isolated from the stems of Eurycoma longifolia. The new compounds were two eurycomanone-type C(20) quassinoids (1, 2), one klaineanone-type C(20) quassinoid (3), one C(19) quassinoid (4) with a 1,2-seco-1-nor-6(5-->10)-abeo-picrasan-2,5-olide skeleton, and six eurycomalactone-type C(19) quassinoids (5-10). Compounds 5 and 6 both possessed a 3,4-epoxy group observed for the first time in eurycomalactones. Compound 1 had an alpha-oriented OH group at C-14 that had not been reported previously in eurycomanone-type quassinoids. All of the isolates were evaluated for cytotoxicity toward the highly metastatic HT-1080 human fibrosarcoma cell line, and compounds 11, 23, and 24 showed potent cytotoxicity (IC(50) values 0.93-1.1 microM).

  3. Isolation of an alpha-methylene-gamma-butyrolactone derivative, a toxin from the plant pathogen Lasiodiplodia theobromae.

    PubMed

    He, Guochun; Matsuura, Hideyuki; Yoshihara, Teruhiko

    2004-10-01

    Lasiodiplodia theobromae is known as a multi-infectious microorganism that causes considerable crop damage, particularly to tropical fruits. When the fruits are infected by L. theobromae, the typical symptom is the appearance of black spots on the surface of the infected fruit. When injected in to the peel of banana, the culture filtrate of L. theobromae induced formation of black spots. The structure of the isolated compound responsible for this effect was determined to be (3S,4R)-3-carboxy-2-methylene-heptan-4-olide on the basis of analysis of MS, IR, and 1H and 13C NMR spectroscopic data, including HMQC, HMBC, and 1H-1H COSY experiments. The active compound was not only isolated from the culture filtrate derived from potato dextrose medium, but also from the extract of infected peels of bananas.

  4. Two New 3,4;9,10-seco-Cycloartane Type Triterpenoids from Illicium difengpi and Their Anti-Inflammatory Activities

    PubMed Central

    Li, Chuntong; Xi, Fengmin; Mi, Junling; Chen, Wansheng

    2013-01-01

    A pair of new 3,4;9,10-seco-cycloartane type triterpenoid stereoisomerides: 24R,25-dihydroxy-3,4;9,10-seco-4(28)-cycloarten-10,3-olide (1) named Illiciumolide A and 24S,25-dihydroxy-3,4;9,10-seco-4(28)-cycloarten-10,3-olide (2) named Illiciumolide B were isolated from the stem bark of Illicium difengpi, as well as five known biogenetically related triterpenoids, including sootepin E (3), betulinic acid (4), lupeol (5), (all-Z)-1,5,9,13,17,21-hexamethyl-1,5,9,13,17,21-cyclotertracosahexaene (6), and (all-E)-2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene (7). The structures of two new compounds were determined on the basis of spectroscopic analysis including 1D-, 2D-NMR, and MS techniques. Two assays were conducted: inhibition of tumor necrosis factor-alpha (TNF-α) and inhibition of nuclear factor kappa B (NF-κB) in RAW264. 7 cells induced by lipopolysaccharide (LPS). It was observed that compounds 1, 2 and 7 showed significant inhibition of TNF-α production and NF-κB release. The molecule docking results showed that compounds 1 and 2 got high fitness scores with dual specificity mitogen-activated protein kinase kinase 1 (MPKK1), whose activation plays a pivotal role between TNF-α and activation of NF-κB. The anti-HIV-1 potency of compounds 1–5 was also discussed, in addition to the results of computer-aided screening for targets. PMID:23762173

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

    PubMed

    Silk, Peter J; Ryall, Krista; Mayo, Peter; Lemay, Matthew A; Grant, Gary; Crook, Damon; Cossé, Allard; Fraser, Ivich; Sweeney, Jon D; Lyons, D Barry; Pitt, Doug; Scarr, Taylor; Magee, David

    2011-08-01

    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/electroantennographic (GC/EAD) analysis of synthetic (3Z)-lactone, which contained 10% (3E)-lactone, showed a strong response of male and female antennae to both isomers. EAG analysis with 0.01- to 100-μg dosages showed a positive dose response, with females giving significantly higher responses than males. In field experiments with sticky purple prism traps, neither lactone isomer affected catches when combined with ash foliar or cortical volatiles (green leaf volatiles or Phoebe oil, respectively). However, on green prism traps, the (3Z)-lactone significantly increased capture of male A. planipennis when traps were deployed in the canopy. Captures of males on traps with both (3E)-lactone and (3Z)-hexenol or with (3Z)-lactone and (3Z)-hexenol were increased by 45-100%, respectively, compared with traps baited with just (3Z)-hexenol. In olfactometer bioassays, males were significantly attracted to (3E)-lactone, but not the (3Z)-lactone or a 60:40 (3E):(3Z) blend. The combination of either (3E)- or (3Z)-lactone with Phoebe oil was not significantly attractive to males. Males were highly attracted to (3Z)-hexenol and the (3Z)-lactone + (3Z)-hexenol combination, providing support for the field trapping results. These data are the first to demonstrate increased attraction with a combination of a pheromone and a green leaf volatile in a Buprestid species.

  6. Use of a Doehlert factorial design to investigate the effects of pH and aeration on the accumulation of lactones by Yarrowia lipolytica.

    PubMed

    García, E Escamilla; Belin, J-M; Waché, Y

    2007-11-01

    To detect rate-limiting steps in the production of lactones by studying the combined effect of pH and aeration on their accumulation. A Doehlert experimental design was chosen to evaluate the accumulation of four lactones in the pH (3.5-7.3) and K(L)a (4.1 h(-1) to 26 h(-1)) experimental domain. The accumulation of gamma-decalactone was higher at pH around 5 and increased at low aeration reaching 496 mg l(-1) at pH 6.35 and K(L)a 4.5 h(-1). The specific accumulation increased at low aeration. The 3-hydroxy-gamma-decalactone accumulation was higher at low pH and high aeration conditions: 660 mg l(-1) at pH 4.4 and 26 h(-1). For dec-2-en-4-olide and dec-3-en-4-olide, lower amounts were reached (104 mg l(-1) and 66 mg l(-1), respectively). Although the accumulation of the four lactones should be related to catalytic steps requiring oxygen, the accumulation of gamma-decalactone was higher in low aeration conditions whereas the one of 3-hydroxy-gamma-decalactone was promoted for high aeration. Decenolides accumulate independently of pH or aeration. This study gives new insights into the catabolism of lipids, such as the role of co-factor regulation and the fact that the 3-hydroxylactone dehydration step is insensitive to pH or aeration.

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

    PubMed

    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. © 2014 The Authors. Microbial Biotechnology published by John Wiley & Sons Ltd and Society for Applied Microbiology.

  8. Dienelactone hydrolase from Pseudomonas sp. strain B13.

    PubMed Central

    Ngai, K L; Schlömann, M; Knackmuss, H J; Ornston, L N

    1987-01-01

    Dienelactone hydrolase (EC 3.1.1.45) catalyzes the conversion of cis- or trans-4-carboxymethylenebut-2-en-4-olide (dienelactone) to maleylacetate. An approximately 24-fold purification from extracts of 3-chlorobenzoate-grown Pseudomonas sp. strain B13 yielded a homogeneous preparation of the enzyme. The purified enzyme crystallized readily and proved to be a monomer with a molecular weight of about 30,000. Each dienelactone hydrolase molecule contains two cysteinyl side chains. One of these was readily titrated by stoichiometric amounts of p-chloromercuribenzoate, resulting in inactivation of the enzyme; the inactivation could be reversed by the addition of dithiothreitol. The other cysteinyl side chain appeared to be protected in the native protein against chemical reaction with p-chloromercuribenzoate. The properties of sulfhydryl side chains in dienelactone hydrolase resembled those that have been characterized for bacterial 4-carboxymethylbut-3-en-4-olide (enol-lactone) hydrolases (EC 3.1.1.24), which also are monomers with molecular weights of about 30,000. The amino acid composition of the dienelactone hydrolase resembled the amino acid composition of enol-lactone hydrolase from Pseudomonas putida, and alignment of the NH2-terminal amino acid sequence of the dienelactone hydrolase with the corresponding sequence of an Acinetobacter calcoaceticus enol-lactone hydrolase revealed sequence identity at 8 of the 28 positions. These observations foster the hypothesis that the lactone hydrolases share a common ancestor. The lactone hydrolases differed in one significant property: the kcat of dienelactone hydrolase was 1,800 min-1, an order of magnitude below the kcat observed with enol-lactone hydrolases. The relatively low catalytic activity of dienelactone hydrolase may demand its production at the high levels observed for induced cultures of Pseudomonas sp. strain B13. PMID:3804973

  9. A novel design of whole-genome microarray probes for Saccharomyces cerevisiae which minimizes cross-hybridization

    PubMed Central

    Talla, Emmanuel; Tekaia, Fredj; Brino, Laurent; Dujon, Bernard

    2003-01-01

    Background Numerous DNA microarray hybridization experiments have been performed in yeast over the last years using either synthetic oligonucleotides or PCR-amplified coding sequences as probes. The design and quality of the microarray probes are of critical importance for hybridization experiments as well as subsequent analysis of the data. Results We present here a novel design of Saccharomyces cerevisiae microarrays based on a refined annotation of the genome and with the aim of reducing cross-hybridization between related sequences. An effort was made to design probes of similar lengths, preferably located in the 3'-end of reading frames. The sequence of each gene was compared against the entire yeast genome and optimal sub-segments giving no predicted cross-hybridization were selected. A total of 5660 novel probes (more than 97% of the yeast genes) were designed. For the remaining 143 genes, cross-hybridization was unavoidable. Using a set of 18 deletant strains, we have experimentally validated our cross-hybridization procedure. Sensitivity, reproducibility and dynamic range of these new microarrays have been measured. Based on this experience, we have written a novel program to design long oligonucleotides for microarray hybridizations of complete genome sequences. Conclusions A validated procedure to predict cross-hybridization in microarray probe design was defined in this work. Subsequently, a novel Saccharomyces cerevisiae microarray (which minimizes cross-hybridization) was designed and constructed. Arrays are available at Eurogentec S. A. Finally, we propose a novel design program, OliD, which allows automatic oligonucleotide design for microarrays. The OliD program is available from authors. PMID:14499002

  10. Terpenoids from rhizomes of Alpinia japonica inhibiting nitric oxide production.

    PubMed

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

    2015-03-01

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

  11. 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.

  12. The fungicidal terpenoids and essential oil from Litsea cubeba in Tibet.

    PubMed

    Yang, Yu; Jiang, Jiazheng; Qimei, Luobu; Yan, Xiaojing; Zhao, Junxia; Yuan, Huizhu; Qin, Zhaohai; Wang, Mingan

    2010-10-13

    A new C₉ monoterpenoid acid (litseacubebic acid, 1) and a known monoterpene lactone (6R)-3,7-dimethyl-7-hydroxy-2-octen-6-olide (2), along with three known compounds--vanillic acid (3), trans-3,4,5-trimethoxylcinnamyl alcohol (4), and oxonantenine (5)--were isolated with bioassay-guided purification from the fruit extract of Litsea cubeba collected in Tibet. The structure of 1 was elucidated by MS, ¹H-NMR, ¹³C-NMR, COSY, HSQC, HMBC, NOE spectral data as 2,6-dimethyl-6-hydroxy-2E,4E-hepta-2,4-diene acid. Additionally 33 compounds were identified from the essential oil of L. cubeba. The preliminary bioassay results showed that 1 and 2 have good fungicidal activities against Sclerotinia sclerotiorum, Thanatephorus cucumeris, Pseudocer-cospora musae and Colletotrichum gloeosporioides at the concentration of 588 and 272 μM, and the essential oil has good fungicidal activities against T. cucumeris and S. sclerotiorum, with IC₅₀ values of 115.58 and 151.25 μg/mL, repectively.

  13. Artefact formation during acid hydrolysis of saponins from Medicago spp.

    PubMed

    Tava, Aldo; Biazzi, Elisa; Mella, Mariella; Quadrelli, Paolo; Avato, Pinarosa

    2017-02-28

    Artefact compounds obtained during acid hydrolysis of saponins from Medicago spp. (Fabaceae), have been monitored and evaluated by GC-FID. Their identification has been performed by GC-MS and (1)H and (13)C NMR. Saponins with different substituents on the triterpenic pentacyclic aglycones were considered, and their hydrolysis products were detected and quantified during 10 h of time course reaction. From soyasapogenol B glycoside the well known soyasapogenols B, C, D and F were obtained together with a previously undescribed sapogenol artefact identified as 3β,22β,24-trihydroxyolean-18(19)-en and named soyasapogenol H. From a zanhic acid saponin two major artefact compounds identified as 2β,3β,16α-trihydroxyolean-13(18)-en-23,28-dioic acid and 2β,3β,16α-trihydroxyolean-28,13β-olide-23-oic acid were obtained, together with some zanhic acid. Other compounds, detected in very small amount in the reaction mixture, were also tentatively identified based on their GC-MS and UV spectra. The other most characteristic saponins in Medicago spp., hederagenin, bayogenin and medicagenic acid glycosides, under acidic condition of hydrolysis, released instead the correspondent aglycones and generated a negligible amount of artefacts. Nature of artefacts and mechanism of their formation, involving a stable tertiary carbocation, is here proposed and discussed for the first time.

  14. Bioactive diterpenoids from Croton laevigatus.

    PubMed

    Zhang, Jun-Sheng; Tang, Ya-Qi; Huang, Jia-Luo; Li, Wei; Zou, Yi-Hong; Tang, Gui-Hua; Liu, Bo; Yin, Sheng

    2017-09-18

    Eight previously undescribed diterpenoids, crolaevinoids A-H, including two halimanes, four clerodanes, and two laevinanes, along with six known analogues were isolated from the twigs of Croton laevigatus. The structures of the previously undescribed were elucidated by spectroscopic analysis, and their absolute configurations were determined by combination of a single crystal X-ray diffraction and CD analysis (exciton chirality and Rh2(OCOCF3)4-induced methods). Crolaevinoids A and B represent the first halimane diterpenoids with a unique lactone bridge between C-12 and C-17. All compounds were evaluated for their inhibitory effects on the nitric oxide (NO) production induced by lipopolysaccharide (LPS) in RAW264.7 macrophage cells. Furocrotinsulolide A and 3,4,15,16-diepoxy-cleroda-13(16),14-diene-12,17-olide exhibited pronounced inhibition of NO production with IC50 values of 10.4 ± 0.8 and 6.0 ± 1.0 μM, respectively, being more potent than the positive control, quercetin (IC50 = 13.1 ± 1.9 μM). Copyright © 2017 Elsevier Ltd. All rights reserved.

  15. 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

  16. [Bioactivity of endophytic actinomycetes from medicinal plants and secondary metabolites from strain D62].

    PubMed

    Liu, Ning; Zhang, Hui; Zheng, Wen; Huang, Ying; Wang, Hai-Bin

    2007-10-01

    It is believed that genetic recombination of the endophytes with the hosts that occurred in evolutionary time could result in some endophytes producing certain phytochemical originally characteristic of the host. Based on this widely accepted hypothesis, there have been increasing research efforts focused on screening for novel natural products from endophytes. In this study, antimicrobial and antitumor activities of 165 actinomycetes isolated from medicinal plants collected from Xishuangbanna were tested by agar diffusion method and WST-8 assay respectively. The results showed that over 42% of the isolates exhibited antagonism against pathogenic strains, and 54.5% displayed excellent inhibition against mouse melanoma cell line B16 or/and human alveolar epithelial cell line A549. These results are superior to those of soil actinomycetes, indicating tremendous potential of endophytic of actinomycetes for exploration. Six compounds that had both antimicrobial and antitumor activities were separated and purified from isolate Streptomyces sp. D62 by resin adsorption, silica-gel column and sephadex chromatography, etc. On the basis of spectral analyses, they were identified as antimycin A4a (1), antimycin A7a (2), antimycin A2a (3), antimycin A1a (4), 10-hydroxy-10-methyl-dodec-2-en-1,4-olide (5) and 6-(2-(4-aminophenyl)-2-oxoethyl)-3,5-dimethyl-tetrahydropyran-2-one(6), with the last one defined as a novel compound. Based on all these results, it is convinced that endophytic actinomycetes are a promising resource for bioactive natural product discovery.

  17. Isolation, structure elucidation and biological activity of metabolites from Sch-642305-producing endophytic fungus Phomopsis sp. CMU-LMA.

    PubMed

    Adelin, Emilie; Servy, Claudine; Cortial, Sylvie; Lévaique, Hélène; Martin, Marie-Thérèse; Retailleau, Pascal; Le Goff, Géraldine; Bussaban, Boonsom; Lumyong, Saisamorn; Ouazzani, Jamal

    2011-12-01

    Eight polyketide compounds were isolated from the cultivation broth of Phomopsis sp. CMU-LMA. We have recently described LMA-P1, a bicyclic 10-membered macrolide, obtained as a bioconversion derivative of Sch-642305, the major compound isolated in this study. Benquinol is the ethyl ester derivative of the 13-dihydroxytetradeca-2,4,8-trienoic acid produced by Valsa ambiens. This compound is concomitantly produced with the 6,13-dihydroxytetradeca-2,4,8-trienoic acid (DHTTA) previously isolated from Mycosphaerellarubella. The absolute configuration of the new compound, (2R,3R,4S,5R)-3-hydroxy-2,4-dimethyl-5-[(S,Z)-3-methylpentenyl]-tetrahydro-pyranone LMA-P2 was confirmed by X-ray crystallography. The δ-lactone 2,3-dihydroxytetradecan-5-olide (DHTO) was previously isolated from Seiridium unicorne. This compound may form through the cyclization of the methyl-2,3,5-trihydroxytridecanoate LMA-P3, a new linear polyketide isolated in this study. Benquoine, a new 14-membered lactone generated from the cyclization of benquinol, is proposed as the key precursor for the biosynthesis of Sch-642305. Antimicrobial activity and cancer cell viability inhibition by the new compounds were investigated. Benquoine exhibits antimicrobial activity against Gram positive bacteria, and cytotoxicity against HCT-116 cancer cell line.

  18. [Triterpenoid sapogenins in the genus Grindelia].

    PubMed

    Kreutzer, S; Schimmer, O; Waibel, R

    1990-08-01

    A saponin fraction has been isolated from the ethanolic extract of Grindeliae herba. The saponin fraction showed strong haemolytic activity. The saponins were detected after separation on TLC by their color reactions and Rf values as well as by their haemolytic activity on blood agar. After hydrolysis, the chemical reactions and Rf values of the sapogenins were described. The main sapogenin was isolated by preparative chromatography and its structure was elucidated by mass, 1H-NMR, 13C-NMR, IR, and UV spectra. The compound is a new natural triterpenoid sapogenin lactone and is named grindeliasapogenin D. Spectral evidence is presented to establish its structure as 2 beta,3 beta,16 alpha,23-tetrahydroxyoleanan-28,13 beta-olide. Two further sapogenins present in small amounts were identified chromatographically as oleanolic acid and bayogenin using authentic reference substances. The aerial parts of Grindelia robusta Nutt, and G. lanceolata Nutt. (Asteraceae) (as well as two commercial extracts) were also investigated with respect to their saponin fraction. The 3 sapogenins mentioned above were detected in all samples. The antibiotic potency of the crude drug is not associated with the saponin fraction but is at least partially due to the resin fraction.

  19. Contact sensitization to calocephalin, a sesquiterpene lactone of the guaianolide type from cushion bush (Leucophyta brownii, Compositae).

    PubMed

    Paulsen, Evy; Christensen, Lars P; Hindsén, Monica; Andersen, Klaus E

    2013-11-01

    Cushion bush [Leucophyta brownii Cass. = Calocephalus brownii (Cass.) F. Muell.] is an Australian Compositae shrub that has been introduced into Scandinavia as a pot plant. The first case of sensitization occurred in a gardener, and the main allergen was identified as the guaianolide calocephalin. To present the identification of the main allergen, and to assess the prevalence of sensitization to calocephalin in Compositae-allergic patients. Calocephalin was isolated from a dichloromethane extract of aerial parts of cushion bush. Calocephalin 0.1% ethanol was included in the plant series in Malmö, Sweden, and Odense, Denmark. Nuclear magnetic resonance (NMR) analysis of calocephalin resulted in a revision of its chemical structure to 4α-acetoxy-1α,2α-epoxy-5α,10αH-guai-11(13)-en-12,8β-olide. The prevalence of patch test positivity was up to 28% in aimed patch testing. Despite strongly positive patch test reactions, the relevance was unknown in the majority of cases, and only 1 person was occupationally sensitized. Calocephalin is a potent contact allergen, but, as cushion bush is a low-maintenance pot plant, primary sensitization is most likely to occur through occupational exposure. Positive reactions in Compositae-sensitive persons probably occur because of cross-reactivity, and patients should be warned about contact with cushion bush plants. © 2013 John Wiley & Sons A/S. Published by John Wiley & Sons Ltd.

  20. Allergenic sesquiterpene lactones from cushion bush (Leucophyta brownii Cass.): new and old sensitizers in a shrub-turned-a-pot plant.

    PubMed

    Paulsen, Evy; Hyldgaard, Mette G; Andersen, Klaus E; Andersen, Flemming; Christensen, Lars P

    2017-05-01

    The Australian cushion bush (Leucophyta brownii) of the Compositae family of plants has become a popular pot and container plant. The plant produces the sesquiterpene lactone allergen calocephalin. To assess the sensitizing potential of sesquiterpene lactones from cushion bush. Eleven Compositae-sensitive patients were patch tested with seven sesquiterpene lactones isolated from cushion bush. Six of seven sesquiterpene lactones elicited positive reactions in 4 of 11 patients. The well-known sesquiterpene lactone pseudoivalin and its derivative pseudoivalin acetate, as well as calocephalin and tomentosin, were confirmed to be sensitizers, whereas leucophytalin A and 4α-hydroxy-5αH,10αH-1,11(13)-guaidien-8β,12-olide were shown to be allergenic for the first time. The patch test reaction patterns seem to follow the chemical patterns, which may eventually make it possible to trace primary sensitizers and advise patients more precisely. © 2017 John Wiley & Sons A/S. Published by John Wiley & Sons Ltd.

  1. Role of beta-oxidation enzymes in gamma-decalactone production by the yeast Yarrowia lipolytica.

    PubMed

    Waché, Y; Aguedo, M; Choquet, A; Gatfield, I L; Nicaud, J M; Belin, J M

    2001-12-01

    Some microorganisms can transform methyl ricinoleate into gamma-decalactone, a valuable aroma compound, but yields of the bioconversion are low due to (i) incomplete conversion of ricinoleate (C(18)) to the C(10) precursor of gamma-decalactone, (ii) accumulation of other lactones (3-hydroxy-gamma-decalactone and 2- and 3-decen-4-olide), and (iii) gamma-decalactone reconsumption. We evaluated acyl coenzyme A (acyl-CoA) oxidase activity (encoded by the POX1 through POX5 genes) in Yarrowia lipolytica in lactone accumulation and gamma-decalactone reconsumption in POX mutants. Mutants with no acyl-CoA oxidase activity could not reconsume gamma-decalactone, and mutants with a disruption of pox3, which encodes the short-chain acyl-CoA oxidase, reconsumed it more slowly. 3-Hydroxy-gamma-decalactone accumulation during transformation of methyl ricinoleate suggests that, in wild-type strains, beta-oxidation is controlled by 3-hydroxyacyl-CoA dehydrogenase. In mutants with low acyl-CoA oxidase activity, however, the acyl-CoA oxidase controls the beta-oxidation flux. We also identified mutant strains that produced 26 times more gamma-decalactone than the wild-type parents.

  2. 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).

  3. 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.

  4. (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

    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.

  5. Role of β-Oxidation Enzymes in γ-Decalactone Production by the Yeast Yarrowia lipolytica

    PubMed Central

    Waché, Yves; Aguedo, Mario; Choquet, Armelle; Gatfield, Ian L.; Nicaud, Jean-Marc; Belin, Jean-Marc

    2001-01-01

    Some microorganisms can transform methyl ricinoleate into γ-decalactone, a valuable aroma compound, but yields of the bioconversion are low due to (i) incomplete conversion of ricinoleate (C18) to the C10 precursor of γ-decalactone, (ii) accumulation of other lactones (3-hydroxy-γ-decalactone and 2- and 3-decen-4-olide), and (iii) γ-decalactone reconsumption. We evaluated acyl coenzyme A (acyl-CoA) oxidase activity (encoded by the POX1 through POX5 genes) in Yarrowia lipolytica in lactone accumulation and γ-decalactone reconsumption in POX mutants. Mutants with no acyl-CoA oxidase activity could not reconsume γ-decalactone, and mutants with a disruption of pox3, which encodes the short-chain acyl-CoA oxidase, reconsumed it more slowly. 3-Hydroxy-γ-decalactone accumulation during transformation of methyl ricinoleate suggests that, in wild-type strains, β-oxidation is controlled by 3-hydroxyacyl-CoA dehydrogenase. In mutants with low acyl-CoA oxidase activity, however, the acyl-CoA oxidase controls the β-oxidation flux. We also identified mutant strains that produced 26 times more γ-decalactone than the wild-type parents. PMID:11722925

  6. Antibacterial and Synergistic Activity of Pentacyclic Triterpenoids Isolated from Alstonia scholaris.

    PubMed

    Wang, Chao-Min; Chen, Hsiao-Ting; Wu, Zong-Yen; Jhan, Yun-Lian; Shyu, Ching-Lin; Chou, Chang-Hung

    2016-01-25

    (1) BACKGROUND: Alstonia scholaris (Apocynaceae) is an important medicinal plant that has been historically used in "Dai" ethnopharmacy to treat infectious diseases in China. Although various pharmacological activities have been reported, the antimicrobial constitutes of A. scholaris have not yet been identified. The objective of this study is to evaluate the antibacterial constitutes from the leaf extract of A. scholaris and to assess the synergistic effects of isolated compounds with antibiotics against bacterial pathogens.; (2) METHODS: The chemical constitutes isolated from the leaf extract of A. scholaris were structurally identified by NMR. The antibacterial and synergistic effect of compounds was assessed by calculating the minimal inhibitory concentration (MIC), checkerboard dilution test, and time-kill assay.; (3) RESULTS: Six pentacyclic triterpenoids were structurally identified as (1) lupeol, (2) betulin, (3) 3-hydroxy-11-ursen-28,13-olide, (4) betulinic acid, (5) oleanolic acid and (6) ursolic acid. Both oleanolic and ursolic acid showed antibacterial activity but were limited to Gram-positive bacteria. Ursolic acid showed a synergistic effect with ampicillin and tetracycline against both Bacillus cereus and S. aureus.; (4) CONCLUSION: These findings reflect that pentacyclic triterpenoids are the antibacterial chemicals in A. scholaris. The ability of ursolic acid to enhance the activity of antibiotics can constitute a valuable group of therapeutic agents in the future.

  7. Antibacterial constituents from Melodinus suaveolens.

    PubMed

    Li, Jiang-Ling; Lunga, Paul-Keilah; Zhao, Yun-Li; Qin, Xu-Jie; Yang, Xing-Wei; Liu, Ya-Ping; Luo, Xiao-Dong

    2015-04-01

    To investigate the non-alkaloidal chemical constituents of the stems and leaves of Melodinus suaveolens and their antibacterial activities. Compounds were isolated and purified by repeated silica gel, Sephadex LH-20, RP18, and preparative HPLC. Their structures were elucidated by comparison with published spectroscopic data, as well as on the basis of extensive spectroscopic analysis. The antibacterial screening assays were performed by the dilution method. Fourteen compounds were isolated, and identified as lycopersene (1), betulinic aldehyde (2), 3β-acetoxy-22,23,24,25,26,27-hexanordammaran-20-one (3), 3a-acetyl-2, 3, 5-trimethyl-7a-hydroxy-5-(4,8,12-trimethyl-tridecanyl)-1,3a,5,6,7,7a-hexahydro-4-oxainden-1-one (4), 3β-hydroxy-28-norlup-20(29)-ene-17β-hydroperoxide (5), 3β-hydroxy-28-norlup-20(29)-ene-17α-hydroperoxide (6), β-sitosterol (7), 28-nor-urs-12-ene-3β, 17β-diol (8), α-amyrin (9), ergosta-4,6,8(14),22-tetraen-3-one (10), 3β-hydroxy-urs-11-en-28,13β-olide (11), betulin (12), obtusalin (13), and ursolic acid (14). Among the isolates, compounds 1, 2, 6, 8, 10, and 14 showed potent antibacterial activities against the four bacteria. This is the first report of the antibacterial activity of the constituents of Melodinus suaveolens.

  8. (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

  9. 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.

  10. Triterpene hexahydroxydiphenoyl esters and a quinic acid purpurogallin carbonyl ester from the leaves of Castanopsis fissa.

    PubMed

    Huang, Yong-Lin; Tsujita, Takaaki; Tanaka, Takashi; Matsuo, Yosuke; Kouno, Isao; Li, Dian-Peng; Nonaka, Gen-ichiro

    2011-11-01

    Triterpene hexahydroxydiphenoyl (HHDP) esters have only been isolated from Castanopsis species, and the distribution of these esters in nature is of chemotaxonomical interest. In this study, the chemical constituents of the leaves of Castanopsis fissa were examined in detail to identify and isolate potential HHDP esters. Together with 53 known compounds, 3,4-di-O-galloyl-1-O-purpurogallin carbonyl quinic acid (1) and 3,24-(S)-HHDP-2α,3β,23,24-tetrahydroxytaraxastan-28,20β-olide (2) were isolated and their structures were elucidated by spectroscopic and chemical methods. The polyphenols of the leaves were mainly composed of galloyl quinic acids, triterpenes HHDP esters, ellagitannins and flavonol glycosides. In particular, the isolation yields of 1,3,4-trigalloyl quinic acid and compound 2 were 1.53% and 0.27%, respectively, from the fresh leaves. The presence of lipid soluble HHDP esters of oleanane-type triterpenes as one of the major metabolites is an important chemotaxonomical discovery. Lipase inhibition activities and ORAC values of the major constituents were compared. The triterpene HHDP ester showed moderate lipase inhibition activity and myricitrin gave the largest ORAC value.

  11. In vitro antileishmanial effects of antibacterial diterpenes from two Ethiopian Premna species: P. schimperi and P. oligotricha.

    PubMed

    Habtemariam, Solomon

    2003-06-06

    Three antibacterial diterpenes: (5R,8R,9S,10R)-12-oxo-ent-3,13(16)-clerodien-15-oic acid (1), 16-hydroxy-clerod-3,13(14)-diene-15,16-olide (2) and ent-12-oxolabda-8,13(16)-dien-15-oic acid (3) were previously isolated form Premna schimperi and P. oligotricha. Since andrographolide and other structurally related diterpenes were shown to have antileishmanial activity, the aim of the present study was to assess the in vitro effect of premna diterpenes against Leishmania aethiopica; the causative agent of cutaneous leishmaniasis in Ethiopia. The diterpenes showed potent concentration-dependant suppressive effect on the viability of axenically cultured amastigotes of L. aethiopica. The clerodane diterpenes 1 and 2 were most active (LD50 values 1.08 and 4.12 microg/ml respectively) followed by andrographolide and 3. Compounds 1 and 2 appear to be over 20 and 10-times respectively more selective to leishmania amastigotes than the permissive host cell line, THP-1 cells or the promastigotes stage of the parasites. The clerodane diterpenes (1, 2) which were more potent and selective than labdanes (andrographolide and 3) are promising for further studies and/or development.

  12. In vitro antileishmanial effects of antibacterial diterpenes from two Ethiopian Premna species: P. schimperi and P. oligotricha

    PubMed Central

    Habtemariam, Solomon

    2003-01-01

    Background Three antibacterial diterpenes: (5R,8R,9S,10R)-12-oxo-ent-3,13(16)-clerodien-15-oic acid (1), 16-hydroxy-clerod-3,13(14)-diene-15,16-olide (2) and ent-12-oxolabda-8,13(16)-dien-15-oic acid (3) were previously isolated form Premna schimperi and P. oligotricha. Since andrographolide and other structurally related diterpenes were shown to have antileishmanial activity, the aim of the present study was to assess the in vitro effect of premna diterpenes against Leishmania aethiopica; the causative agent of cutaneous leishmaniasis in Ethiopia. Results The diterpenes showed potent concentration-dependant suppressive effect on the viability of axenically cultured amastigotes of L. aethiopica. The clerodane diterpenes 1 and 2 were most active (LD50 values 1.08 and 4.12 μg/ml respectively) followed by andrographolide and 3. Compounds 1 and 2 appear to be over 20 and 10-times respectively more selective to leishmania amastigotes than the permissive host cell line, THP-1 cells or the promastigotes stage of the parasites. Conclusion The clerodane diterpenes (1, 2) which were more potent and selective than labdanes (andrographolide and 3) are promising for further studies and/or development. PMID:12793911

  13. Sesquiterpenes and diterpenes from Ambrosia arborescens.

    PubMed

    De Leo, Marinella; Saltos, Mariela Beatriz Vera; Puente, Blanca Fabiola Naranjo; De Tommasi, Nunziatina; Braca, Alessandra

    2010-05-01

    Six compounds, eudesm-11(13)-en-4beta,9beta-diol, 15R,16-dihydroxy-3-oxoisopimar-9(11)-ene, 15S,16-dihydroxy-3-oxoisopimar-9(11)-ene, 1alpha-hydroxy-7-oxo-iso-anhydrooplopanone, 10alpha-hydroxy-11,13-dihydro-5-epi-psilostachyin, and 4beta-hydroxypseudoguaian-12,6-olide 4-O-beta-d-glucopyranoside, together with 12 known sesquiterpenes, were isolated from the leaves of Ambrosia arborescens. Structures were elucidated by 1D and 2D NMR spectroscopy including 1D-TOCSY, DQF-COSY, 2D-ROESY, HSQC, and HMBC experiments, as well as by ESI mass spectrometry. The absolute configuration of the 15,16-diol moiety in 15R,16-dihydroxy-3-oxoisopimar-9(11)-ene and 15S,16-dihydroxy-3-oxoisopimar-9(11)-ene was determined using Snatzke's method. All compounds were evaluated for antiproliferative activity. Copyright 2010 Elsevier Ltd. All rights reserved.

  14. Phytotoxic Eremophilanes from Ligularia macrophylla.

    PubMed

    Cantrell, Charles L; Duke, Stephen O; Fronczek, Frank R; Osbrink, Weste L A; Mamonov, Leonid K; Vassilyev, Juriy I; Wedge, David E; Dayan, Franck E

    2007-12-26

    Systematic bioassay-guided fractionation of the methylene chloride extract of the roots from Ligularia macrophylla was performed to identify both phytotoxic and antifungal compounds. Four phytotoxic eremophilanes (furanoeremophilan-14beta,6alpha-olide, 6beta-angeloyloxy-10beta-hydroxyfuranoeremophilane, eremophil-7(11)-ene-12,8alpha;14beta,6alpha-diolide, and 3alpha-angeloyloxybakkenolide A) and two antifungal fatty acids (linoleic acid and alpha-linolenic acid) were isolated. The X-ray crystal structure determination of 6beta-angeloyloxy-10beta-hydroxyfuranoeremophilane is reported here for the first time. All four eremophilanes substantially inhibited growth of the monocot Agrostis stolonifera (bentgrass) while demonstrating little activity against the dicot Lactuca sativa (lettuce) at 1000 microM. In a dose-response screening of all compounds for growth inhibitory activity against Lemna paucicostata, 6beta-angeloyloxy-10beta-hydroxyfuranoeremophilane was the most active with an IC50 of 2.94+/-0.16 microM. This compound also caused the greatest reduction of photosynthetic electron flow; however, its mode of action remains to be determined. Evaluation of isolated compounds for activity against the Formosan subterranean termite, Coptotermes formosanus, is also reported. At a concentration of 0.5% (wt/wt), 6beta-angeloyloxy-10beta-hydroxyfuranoeremophilane significantly reduced the consumption of filter paper by C. formosanus.

  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. Pinolide, a new nonenolide produced by Didymella pinodes , the causal agent of ascochyta blight on Pisum sativum.

    PubMed

    Cimmino, Alessio; Andolfi, Anna; Fondevilla, Sara; Abouzeid, Mohamed A; Rubiales, Diego; Evidente, Antonio

    2012-05-30

    An aggressive isolate of Didymella pinodes isolated from pea ( Pisum sativum ) produced four different metabolites in vitro. The metabolites isolated from the culture filtrates were characterized by spectroscopic and optical methods. A new nonenolide, named pinolide, was isolated and characterized as (2S*,7R*,8S*,5E,9R*)-2,7,8-trihydroxy-9-propyl-5-nonen-9-olide. Pinolidoxin, the main toxin produced by D. pinodes, was also isolated together with two other closely related nonenolides, identified as herbarumin II and 2-epi-herbarumin II. Herbarumin II and 2-epi-herbarumin II have been previously isolated from the fungi Phoma herbarum and Paraphaeosphaeria recurvifoliae , respectively, but described here to be isolated for the first time from D. pinodes. When tested on leaves of the host plant and other legumes and weeds, pinolidoxin was phytotoxic in all of the plant species, whereas the other three nonenolides did not produce any symptoms. The importance of the stereochemistry of the hydroxy group at C-7 on phytotoxicity also is discussed.

  17. 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. Copyright © 2015. Published by Elsevier Ltd.

  18. 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

    2013-07-15

    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.

  19. Antioxidant compounds from the stem bark of Garcinia atroviridis.

    PubMed

    Tan, Wen-Nee; Khairuddean, Melati; Wong, Keng-Chong; Tong, Woei-Yenn; Ibrahim, Darah

    2016-08-01

    A new xanthone, namely garcinexanthone G (1), along with eight known compounds, stigmasta-5,22-dien-3β-ol (2), stigmasta-5,22-dien-3-O-β-glucopyranoside (3), 3β-acetoxy-11α,12α-epoxyoleanan-28,13β-olide (4), 2,6-dimethoxy-p-benzoquinone (5), 1,3,5-trihydroxy-2-methoxyxanthone (6), 1,3,7-trihydroxyxanthone (7), kaempferol (8) and quercetin (9), were isolated from the stem bark of Garcinia atroviridis. Their structures were elucidated based on spectroscopic methods including nuclear magnetic resonance (NMR-1D and 2D), UV, IR, and mass spectrometry. All the isolated compounds were evaluated for their antioxidant properties based on the DPPH radical scavenging activities. Results showed that 1,3,7-trihydroxyxanthone and quercetin showed significant antioxidant activities with EC50 values of 16.20 and 12.68 μg/ml, respectively, as compared to the control, ascorbic acid (7.4 μg/ml).

  20. Identification of In-Chain-Functionalized Compounds and Methyl-Branched Alkanes in Cuticular Waxes of Triticum aestivum cv. Bethlehem

    PubMed Central

    Racovita, Radu C.; Jetter, Reinhard

    2016-01-01

    In this work, cuticular waxes from flag leaf blades and peduncles of Triticum aestivum cv. Bethlehem were investigated in search for novel wax compounds. Seven wax compound classes were detected that had previously not been reported, and their structures were elucidated using gas chromatography-mass spectrometry of various derivatives. Six of the classes were identified as series of homologs differing by two methylene units, while the seventh was a homologous series with homologs with single methylene unit differences. In the waxes of flag leaf blades, secondary alcohols (predominantly C27 and C33), primary/secondary diols (predominantly C28) and esters of primary/secondary diols (predominantly C50, combining C28 diol with C22 acid) were found, all sharing similar secondary hydroxyl group positions at and around C-12 or ω-12. 7- and 8-hydroxy-2-alkanol esters (predominantly C35), 7- and 8-oxo-2-alkanol esters (predominantly C35), and 4-alkylbutan-4-olides (predominantly C28) were found both in flag leaf and peduncle wax mixtures. Finally, a series of even- and odd-numbered alkane homologs was identified in both leaf and peduncle waxes, with an internal methyl branch preferentially on C-11 and C-13 of homologs with even total carbon number and on C-12 of odd-numbered homologs. Biosynthetic pathways are suggested for all compounds, based on common structural features and matching chain length profiles with other wheat wax compound classes. PMID:27820857

  1. 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. © 2015 International Union of Biochemistry and Molecular Biology.

  2. 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

  3. Investigation of the Antiproliferative Properties of Natural Sesquiterpenes from Artemisia asiatica and Onopordum acanthium on HL-60 Cells in Vitro

    PubMed Central

    Molnár, Judit; Szebeni, Gábor J.; Csupor-Löffler, Boglárka; Hajdú, Zsuzsanna; Szekeres, Thomas; Saiko, Philipp; Ocsovszki, Imre; Puskás, László G.; Hohmann, Judit; Zupkó, István

    2016-01-01

    Plants and plant extracts play a crucial role in the research into novel antineoplastic agents. Four sesquiterpene lactones, artecanin (1), 3β-chloro-4α,10α-dihydroxy-1α,2α-epoxy-5α,7αH-guaia-11(13)-en-12,6α-olide (2), iso-seco-tanapartholide 3-O-methyl ether (3) and 4β,15-dihydro-3-dehydrozaluzanin C (4), were isolated from two traditionally used Asteraceae species (Onopordum acanthium and Artemisia asiatica). When tested for antiproliferative action on HL-60 leukemia cells, these compounds exhibited reasonable IC50 values in the range 3.6–13.5 μM. Treatment with the tested compounds resulted in a cell cycle disturbance characterized by increases in the G1 and G2/M populations, while there was a decrease in the S phase. Additionally, 1–3 elicited increases in the hypodiploid (subG1) population. The compounds elicited concentration-dependent chromatin condensation and disruption of the membrane integrity, as revealed by Hoechst 33258–propidium staining. Treatment for 24 h resulted in significant increases in activity of caspases-3 and -9, indicating that the tested sesquiterpenes induced the mitochondrial pathway of apoptosis. The proapoptotic properties of the sesquiterpene lactones were additionally demonstrated withannexin V staining. Compounds 1 and 2 increased the Bax/Bcl-2 expression and decreased the expressions of CDK1 and cyclin B2, as determined at the mRNA level by means of RT-PCR. These experimental results indicate that sesquiterpene lactones may be regarded as potential starting structures for the development of novel anticancer agents. PMID:26901188

  4. 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.

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

    PubMed Central

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

    2013-01-01

    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. PMID:23297195

  6. Different types of dienelactone hydrolase in 4-fluorobenzoate-utilizing bacteria.

    PubMed Central

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

    1990-01-01

    Of various benzoate-utilizing bacteria tested, Alcaligenes eutrophus 335, A. eutrophus H16, A. eutrophus JMP222, A. eutrophus JMP134, Alcaligenes strain A7, and Pseudomonas cepacia were able to grow with 4-fluorobenzoate as the sole source of carbon and energy. P. cepacia also utilizes 3-fluorobenzoate. Except for A. eutrophus JMP134, which is known to grow with 2,4-dichlorophenoxyacetate and 3-chlorobenzoate (R. H. Don and J. M. Pemberton, J. Bacteriol. 145:681-686, 1981), the strains were unable to grow at the expense of these compounds or 4-chlorobenzoate. Assays of cell extracts revealed that all strains express dienelactone hydrolase and maleylacetate reductase activities in addition to enzymes of the catechol branch of the 3-oxoadipate pathway when growing with 4-fluorobenzoate. Induction of dienelactone hydrolase and maleylacetate reductase apparently is not necessarily connected to synthesis of catechol 1,2-dioxygenase type II and chloromuconate cycloisomerase activities, which are indispensable for the degradation of chlorocatechols. Substrate specificities of the dienelactone hydrolases provisionally differentiate among three types of this activity. (i) Extracts of A. eutrophus 335, A. eutrophus H16, A. eutrophus JMP222, and Alcaligenes strain A7 convert trans-4-carboxymethylenebut-2-en-4-olide (trans-dienelactone) much faster than the cis-isomer (type I). (ii) The enzyme present in P. cepacia shows the opposite preference for the isomeric substrates (type II). (iii) Cell extracts of A. eutrophus JMP134, as well as purified dienelactone hydrolase from Pseudomonas strain B13 (E. Schmidt and H.-J. Knackmuss, Biochem. J. 192:339-347, 1980), hydrolyze both dienelactones at rates that are of the same order of magnitude (type III). This classification implies that A. eutrophus JMP134 possesses at least two different dienelactone hydrolases, one of type III encoded by the plasmid pJP4 and one of type I, which is also present in the cured strain JMP222. PMID

  7. The effect of compactin, a potent inhibitor of 3-hydroxy-3-methylglutaryl coenzyme-A reductase activity, on cholesterogenesis and serum cholesterol levels in rats and chicks.

    PubMed

    Fears, R; Richards, D H; Ferres, H

    1980-04-01

    Compactin, [7-(1,2,6,7,8,8a-hexahydro-2-methyl-8-(2-methylbutyrylox)naphthyl)-3-hydroxyheptan-5-olide], a potent competitive inhibitor of the rate-determining step in cholesterol biosynthesis, was used to study the influence of changes in cholesterogenesis on serum cholesterol levels. Up to 3 h after a single oral dose (20 or 50 mg/kg) or after the last of a series of daily oral doses (50 mg/kg for 7 or 28 days) to young, male normolipidaemic rats, compactin consistently inhibited cholesterogenesis measured using 3H20 in liver, ileum and other extrahepatic tissues without affecting fatty acid synthesis. Compactin did not reduce serum or tissue cholesterol nor affect the serum concentration of other lipids nor the ratio between lipoprotein classes. A diurnal variation in the effect of compactin on cholesterogenesis was observed. For example, by 12--20 h after dosing, cholesterogenesis at all sites was increased above the comparable control value, indicating the induction of enzyme synthesis and overall there was little effect on the mass of cholesterol synthesized per day. Similar results were obtained using male chicks. Inhibition of cholesterogenesis by compactin was also observed in cholestyramine-treated rats, in which cholesterol turnover was markedly increased, and even in cholesterol-fed rats, in which cholesterogenesis already was repressed. In neither case, however, was inhibition of cholesterogenesis accompanied by a hypocholesterolaemic effect. It is concluded that a more persistent suppression of cholesterogenesis, than that observed with compactin in the rat, may be required in order to affect serum cholesterol concentrations.

  8. Comparison of total phenolic content, scavenging activity and HPLC-ESI-MS/MS profiles of both young and mature leaves and stems of Andrographis paniculata.

    PubMed

    Chua, Lee Suan; Yap, Ken Choy; Jaganath, Indu Bala

    2013-12-01

    The total phenolic content and radical scavenging activity of Andrographis paniculata has been investigated to estimate the amount of phenolic compounds and diterpene lactones, respectively in the plant extracts. The stem extracts exhibited higher total phenolic content and scavenging activity than those of the leaf extracts from both young and mature plants. A range of 19.6-47.8 mg extract of A. paniculata from different parts of the plant is equivalent to the scavenging activity exhibited by one mg of standard Trolox. HPLC-ESI-MS/MS was also used to identify simultaneously the phytochemicals from the leaves and stems of both young and mature plant samples. Of the identified compounds, seven of the sixteen diterpene lactones, three of the six flavonoids, five of the six phenolic acids and two cyclic acids are reported here for the first time for this species. Multivariate statistical approaches such as Hierarchiral Component Analysis (HCA) and Principle Component Analysis (PCA) have clustered the plant extracts into the leaf and stem groups, regardless of plant age. Further classification based on the phytochemical profiles revealed that mostly phenolic acids and flavonoids were from the young leaf extracts, and diterpenoids and their glycosides from the mature leaf extracts. However, the phytochemical profiles for the stems of both young and mature plants were not significantly different as presented in the dendrogram of HCA and the score plot of PCA. The marker for mature plants might be the m/z 557 ion (dihydroxyl dimethyl 19-[(beta-D-glucopyranosyl)oxy]-19-oxo-ent-labda-8(17),13-dien-16,15-olide), whereas the m/z 521 ion (propyl neoandrographolide) could be the marker for leaf extracts.

  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. Three new triterpenes from Nerium oleander and biological activity of the isolated compounds.

    PubMed

    Fu, Liwei; Zhang, Shujun; Li, Na; Wang, Jinlan; Zhao, Ming; Sakai, Junichi; Hasegawa, Toshiaki; Mitsui, Tomokazu; Kataoka, Takao; Oka, Seiko; Kiuchi, Miwa; Hirose, Katutoshi; Ando, Masayoshi

    2005-02-01

    New ursane-type triterpene 1, oleanane-type triterpene 2, and dammarane-type triterpene 15 were isolated from the leaves of Nerium oleander together with 12 known triterpenes, 3beta-hydroxy-12-ursen-28-oic acid (ursolic acid, 3), 3beta,27-dihydroxy-12-ursen-28-oic acid (4), 3beta,13beta-dihydroxyurs-11-en-28-oic acid (5), 3beta-hydroxyurs-12-en-28-aldehyde (6), 28-norurs-12-en-3beta-ol (7), urs-12-en-3beta-ol (8), urs-12-ene-3beta,28-diol (9), 3beta-hydroxy-12-oleanen-28-oic acid (oleanolic acid, 10), 3beta,27-dihydroxy-12-oleanen-28-oic acid (11), 3beta-hydroxy-20(29)-lupen-28-oic acid (betulinic acid, 12), 20(29)-lupene-3beta,28-diol (betulin, 13), and (20S,24R)-epoxydammarane-3beta,25-diol (14). On the basis of their spectroscopic data, the structures of the new compounds 1, 2, and 15 were established as 3beta,20alpha-dihydroxyurs-21-en-28-oic acid, 3beta,12alpha-dihydroxyoleanan-28,13beta-olide, and (20S,24S)-epoxydammarane-3beta,25-diol, respectively. The anti-inflammatory activity of the seven isolated compounds and methyl esters of ursolic acid and oleanoic acid in vitro was examined on the basis of inhibitory activity against the induction of the intercellular adhesion molecule-1 (ICAM-1). The anticancer activity of the 14 isolated compounds, including 1, 2, 15, and methyl esters of ursolic acid and oleanolic acid in vitro was examined on the basis of the cell growth inhibitory activities toward three kinds of human cell lines.

  11. 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.

  12. A clerodane diterpene from Polyalthia longifolia as a modifying agent of the resistance of methicillin resistant Staphylococcus aureus.

    PubMed

    Gupta, Vivek Kumar; Tiwari, Nimisha; Gupta, Priyanka; Verma, Surjeet; Pal, Anirban; Srivastava, Santosh Kumar; Darokar, Mahendra Pandurang

    2016-06-01

    Staphylococcus aureus infections are raising serious concern across the world. The effectiveness of conventional drugs is continuously decreasing due to global emergence of multidrug resistance (MDR) and therefore, new resistance-modifying agents (RMAs) are highly needed. Clerodane diterpene 16α-hydroxycleroda-3,13(14)-Z-dien-15,16-olide (CD) from leaves of Polyalthia longifolia (Sonn.) Thwaites (Annonaceae) as RAM will be useful in improving the current treatment strategies for staphylococcal infections. In the present study, we determine the resistance-modifying activity of CD using clinical isolates of MRSA. Further, the influence of CD on innate immune response was also evaluated in vitro and in vivo. The nature of potential interactions was determined by fractional inhibitory concentration indices (FICIs) calculated from microdilution assays and time-kill curves. The result of in vitro combination study showed that CD significantly reduced MIC of fluoroquinolones up to 16-folds (FICI 0.315-0.500), while in S. aureus infected Swiss albino mice model, combination of CD with norfloxacin, significantly (p<0.01, p<0.001) lowered the systemic microbial burden in blood, liver, kidney, lung and spleen tissues in comparison to CD, norfloxacin alone as well as untreated control. Flow cytometry analysis clearly showed that CD significantly inhibited EtBr efflux and extended post-antibiotic effect. In qRT-PCR analysis, CD alone as well as in combination, significantly modulated the expression of various efflux pump genes including norA up to 2-fold in clinical isolate MRSA-ST2071. Further, the in vitro combination study of the CD (10, 5, 2.5µg/ml) along with the norfloxacin (10µg/ml) depicted a significant decline in the pro-inflammatory cytokines, IL6 and TNF-α. In septic shock mice model, CD did not exhibit any significant changes in the level of pro-inflammatory cytokines. This is the first report on drug resistance-modifying potential of CD through inhibition of