Sample records for laevad olid puust

  1. 2-buten-4-olide, an endogenous feeding suppressant, improves spatial performance through brain acidic fibroblast growth factor in mice.


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


    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.

  2. 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


    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

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


    Khan, M S Y; Husain, A


    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.

  4. 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


    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

  5. 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


    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

  6. 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


    (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

  7. 12-Nitro-methyl-14-deoxy-andro-graph-olide.


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


    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.

  8. 3β-Acet­oxy-12α-chloro-d-friedooleanan-28,14β-olide

    PubMed Central

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


    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

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

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

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


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


    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.

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


    Mustafa, Akhlaq; Ali, Mohammed


    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.

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


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


    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.

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


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


    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).

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

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


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


    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)).

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


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


    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.

  17. Two new sesquiterpenes from Chloranthus japonicus Sieb.


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


    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.

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


    Takayanagi, Tomomi; Ishikawa, Toru; Kitajima, Junichi


    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.

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


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


    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.

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

    DTIC Science & Technology


    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

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


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


    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.

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


    Moon, Hyung-In; Zee, Okpyo


    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.

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


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


    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.

  4. 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


    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

  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


    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.


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


    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.


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


    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. Secondary metabolites from Senecio burtonii (Compositae).


    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


    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.

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


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


    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.

  10. Two new triterpenoids from Photinia serrulata.


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


    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.

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


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


    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.

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


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


    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.

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

    DTIC Science & Technology


    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

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


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


    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.

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


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


    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.

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


    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


    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.

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


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


    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.

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


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


    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.

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


    Rajiv, P; Rajeshwari, Sivaraj; Venckatesh, Rajendran


    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.

  20. Quassinoids from Eurycoma longifolia.


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


    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).

  1. 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.


    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

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


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


    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.

  3. 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


    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.

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


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


    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.

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


    He, Guochun; Matsuura, Hideyuki; Yoshihara, Teruhiko


    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.

  6. Dienelactone hydrolase from Pseudomonas sp. strain B13.

    PubMed Central

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


    Dienelactone hydrolase (EC 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, 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

  7. 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


    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

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


    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


    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.

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


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


    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).

  10. 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


    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

  11. 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


    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

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


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


    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.

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


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


    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.

  14. (R)-Desmolactone is a sex pheromone or sex attractant for the endangered valley elderberry longhorn beetle Desmocerus californicus dimorphus and several congeners (Cerambycidae: Lepturinae).


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


    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.

  15. [Triterpenoid sapogenins in the genus Grindelia].


    Kreutzer, S; Schimmer, O; Waibel, R


    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.

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


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


    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. Phytotoxic Eremophilanes from Ligularia macrophylla.


    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


    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.

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


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


    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.

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

    PubMed Central

    Jameel, Mohammad; Ali, Abuzer; Ali, Mohammed


    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

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


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


    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.

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


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


    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.

  2. (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.


    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

  3. Antibacterial constituents from Melodinus suaveolens.


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


    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.

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


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


    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.

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


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


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

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


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


    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.

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


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


    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.

  8. 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)


    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.

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


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


    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.

  10. 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.


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


    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.

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

    PubMed Central

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


    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

  12. 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


    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

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


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


    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.

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


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


    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.

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


    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


    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.

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


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


    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.

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


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


    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.