共查询到20条相似文献,搜索用时 15 毫秒
1.
Zakaria Cheikh-Ali Timothée Okpekon François Roblot Christian Bories Matthieu Cardao Jean-Christophe Jullian Erwan Poupon Pierre Champy 《Phytochemistry letters》2011,4(3):240-244
Two novel labdane diterpenoids, 15ξ-methoxy-labdan-8(17),11(E),13(14)-trien-15,16-olide (1) and 12(S)-hydroxy-15ξ-methoxy-labdan-8(17),13(14)-dien-15,16-olide (2) were isolated from the rhizomes of Aframomum sceptrum K. Schum (Zingiberaceae). Their structures were established on the basis of their spectroscopic data. Stigmast-4-en-6β-ol-3-one and caryophylene oxide were also obtained. In vitro trypanocidal and leishmanicidal activities of labdanes 1 and 2 were evaluated. Compound 2 exhibited activity similar to that of reference drugs against Leishmania donovani. 相似文献
2.
《Journal of enzyme inhibition and medicinal chemistry》2013,28(3):348-355
The biotransformation of dehydroepiandrosterone (1) with Macrophomina phaseolina was investigated. A total of eight metabolites were obtained which were characterized as androstane-3,17-dione (2), androst-4-ene-3,17-dione (3), androst-4-ene-17β-ol-3-one (4), androst-4,6-diene-17β-ol-3-one (5), androst-5-ene-3β,17β-diol (6), androst-4-ene-3β-ol-6,17-dione (7), androst-4-ene-3β,7β,17β?triol (8), and androst-5-ene-3β,7α,17β-triol (9). All the transformed products were screened for enzyme inhibition, among which four were found to inhibit the β-glucuronidase enzyme, while none inhibited the α-chymotrypsin enzyme. 相似文献
3.
J. Jizba G. V. Samoukina T. Ivanova-Kovacheva N. V. Kandybin 《Folia microbiologica》1992,37(6):461-462
Mixtures of 5,6,7,7a-tetrahydro-3H-pyrrolizin-3-one (1) and 5,6,7,7a-tetrahydro-3H-pyrrolizin-7a-ol-3-one (2) isolated from shaken cultures ofStreptomyces griseus exhibited contact killing effects on larvae ofLeptinotarsa decemlineata andAedes aegypti comparable with those of macrotetrolides and the commercial bioinsecticide Bactoculicid, respectively.Galleria mellonella (caterpillars),Anagasta kühniella andTetranychus urticae were insensitive to this action. 相似文献
4.
《Biocatalysis and Biotransformation》2013,31(4):141-146
AbstractBiotransformation of 5α-hydroxycaryophylla-4(12),8(13)-diene (1) was studied with Cunninghamella elegans and Rhizopus stolonifer. Incubation of 1 with C. elegans gave regioselective oxidative addition (hydration) and isomerization at the C-4(12) exocyclic double bond and hydroxylation at C-3 and C-15, and thus provided two polar metabolites, (3Z),8(14)-caryophylladiene-5α,(11R)-15-diol (2) and 3β,4β,5α-trihydroxycaryophylla-8(13)-ene (3). Incubation of 1 with R. stolonifer gave a transannular cyclization reaction and afforded 2β-methoxyclovan-9-one (4), clovan-2β-ol-9-one (5) and 8-methoxycaryolane-5α,13β-diol (6). Compounds 3 and 6 are new compounds described here for the first time; their structures were deduced with the help of different spectroscopic techniques. 相似文献
5.
Franz Schwarzenberger Kristina Tomov Dana Hole
kov Bernd Matern Erich Mstl 《Zoo biology》1996,15(2):159-171
The metabolism and excretion of progesterone in different animal species results in several fecal 5-reduced progesterone metabolites (pregnanes), which in recent studies were quantified using progesterone antibodies. To increase the accuracy of fecal 20-oxo-pregnane evaluations in the black rhinoceros, enzyme immunoassays (EIA) using antibodies against 5α-pregnane-3β-ol-20-one 3HS:BSA (5α-20-one EIA) and 5β-pregnane-3α-ol-20-one 3HS:BSA (5β-20-one EIA) were developed. The assays showed high crossreactivities with pregnanes containing a 20-oxo group and are referred to as group-specific; results of these assays were compared with an EIA using an antibody against 6HS-progesterone (4-ene-20-one EIA). Fecal samples of both subspecies of the black rhinoceros (Diceros bicornis michaeli, n = 5, and Diceros bicornis minor, n = 1) during pregnancy were collected 1–3 times/week. HPLC separation showed three major immunoreactive fecal 20-oxo-pregnane peaks; their elution profiles and different crossreactivities in the three EIAs provided strong evidence that these peaks are 5α-pregnane-3, 20-dione, 5α-pregnane-3α-ol-20-one, and 5α-pregnane-3β-ol-20-one. Pregnane values in the pregnant animals continuously increased between months 3–7 and were significantly (P < 0.01) elevated above the levels of nonpregnant animals (0.2 μg/g) by week 11. During months 6–13 concentrations in the 5α-20-one and in the 5β-20-one EIA (5–11 μg/g) were significantly (P < 0.01) higher than in the 4-ene-20-one EIA (1.5–3 μg/g). In conclusion, the immunoreactive fecal 20-oxo-pregnane metabolites in the black rhinoceros are determined more accurately with antibodies against pregnane-20-one-C3 conjugates, as compared with a progesterone antibody. © 1996 Wiley-Liss, Inc. 相似文献
6.
Suspension cultured cells of Caragana chamlagu (Leguminosae) converted zerumbone (1) into zerumbone epoxide (2) as the intermediate, (2R,3R,7R)-2,3-epoxy-9-humulen-8-one (3) and (2R,3S,7R)-2,3-epoxy-9-humulen-8-one (4) as new sesquiterpenes in 11%, 36% and 21% yields, respectively. 相似文献
7.
Rong Sun Xi Zheng Xin Wang Li-Zhi Dang Zhong-Shan Yang Shao-Liu Luo Ke-Qin Zhang Guo-Hong Li 《Phytochemistry letters》2011,4(3):320-322
A basidiomycete fungus, Stereum sp. YMF1.1684, was studied for its ability to produce new compounds on nutrient-enriched cultivation media. One new benzofuran, 2-hydroxy-1-((S)-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-5-yl)propan-1-one, named as phenostereum A (1) and one novel dimer benzofuran, named as phenostereum B (2) were isolated from EtOAc extract of the culture broth of the fungus Stereum sp. YMF1.1684. The structures were elucidated using spectroscopic data from 1D, 2D NMR and HRESIMS experiments. 相似文献
8.
Meiwen Huang Shungang Jiao Fuxing Ge Wuken Shana Anni Li Xiaochun Zhou Changxin Liu Pengfei Tu Xingyun Chai 《化学与生物多样性》2021,18(3):e2001065
Two enantiomeric humulane sesquiterpenes, namely (+)-alashanoid N ( 1a ) and (−)-alashanoid N ( 1b ), along with two known analogs ((2R,3R,5R)-2,3-epoxy-6,9-humuladien-5-ol-8-one ( 2 ) and (2R,3S,5R)-2,3-epoxy-6,9-humuladien-5-ol-8-one ( 3 )), were described from the peeled stems of a folk Mongolian herbal medicine Syringa pinnatifolia. Their structures were characterized based on UV, IR, NMR, and HR-ESI-MS data analyses, and the absolute configurations were determined by data analysis of X-ray diffraction and quantum chemical calculations. (+/−)-Alashanoid N showed inhibition against NO production in RAW 264.7 macrophage cells with IC50 values of 90.1 μM and 71.7 μM, and protective effect against oxygen-glucose deprivation injury to H9c2 cells at a concentration of 20 μM and 5 μM, respectively. 相似文献
9.
《Bioscience, biotechnology, and biochemistry》2013,77(4):966-970
(1S,6R)-2,7(14),10-bisabolatrien-1-ol-4-one and (+)-7(14),10-bisaboladien-1-ol-4-one were isolated and identified from Cryptomeria japonica as antifeedants against Locusta migratoria L. which is well known as a serious pest to cereals throughout the world. These compounds strongly inhibited the feeding of L. migratoria only when they were combined, but each compound alone did not show any activity. 相似文献
10.
Yasuo Shimizu Shigeki Matsuto Yasuyuki Mizunuma Ikunosuke Okada 《Bioscience, biotechnology, and biochemistry》2013,77(6):845-853
Seven weakly acidic compounds were newly detected as flavor components of roast barley by using column and gas-liquid chromatographies. These compounds were characterized and identified by MS, IR, UV and NMR spectroscopies and the mixed melting point test.These are 5-hydroxymaltol, maltol, 5-methylcyclopent-2-en-2-ol-1-one, phenol, m-cresol, pyrocatechol, resorcinol and an unidentified compound (MW 128). Maltol, 5-methylcyclopent-2-en-2-ol-1-one and 5-hydroxymaltol have so-called “sugary flavor,” and these compounds appear to concern with the sweet fragrant flavor of roast barley together with vanillin previously identified.Phenol, m-cresol, pyrocatechol and resorcinol which have a strong characteristic odor are supposed to concern with the smoky flavor of roast barley. 相似文献
11.
Phytochemical investigation of the underground parts of Liriope graminifolia (Linn.) Baker resulted in the isolation of two new steroidal saponins lirigramosides A (1) and B (2) along with four known compounds. The structures were determined by extensive spectral analysis, including two-dimensional (2D) NMR spectroscopy and chemical methods, to be 3-O-{β-d-xylopyranosyl-(1→3)-α-l-arabinopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→4)]-β-d-glucopyranosyl-(25S)-spirost-5-ene-3β,17α-diol (1), 1-O-[α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranosyl]-(25R)-ruscogenin (2), 1-O-β-d-xylopyranosyl-3-O-α-l-rhamnopyranosyl-(25S)-ruscogenin (3), 3-O-α-l-rhamnopyranosyl-1-O-sulfo-(25S)-ruscogenin (4), methylophiopogonanone B (5), and 5,7-dihydroxy-3-(4-methoxybenzyl)-6-methyl-chroman-4-one, (ophiopogonanone B, 6), respectively. Compound 1 has a new (25S)-spirost-5-ene-3β,17α-diol ((25S)-pennogenin) aglycone moiety. The isolated compounds were evaluated for their cytotoxic activities against Hela and SMMC-7721 cells. 相似文献
12.
It has been shown that the cultured cells of Digitalis purpruea are capable of transforming progesterone (I) to 5α-pregnane-3,20-dione (II), 5α-pregnan-3β-ol-20-one (III), its glucoside (IV), 5α-pregnane-3β,20α-diol (V), its glucoside (VI), 5α-pregnane-3β,20β-diol (VII), its glucoside (VIII), Δ4-pregnen-20α-ol-3-one (IX), its glucoside (X), Δ-pregnen-20β-ol-3-one (XI) and its glucoside (XII). 5α-Pregnan-3β-ol-20-one glucoside (IV), 5α-pregnane-3β,20α-diol glucoside (VI), 5α-pregnane-3β,20β-diol glucoside (VIII), Δ4-pregnen-20α-ol-3-one glucoside (X) and Δ4-pregnen-20β-ol-3-one glucoside (XII) have been found for the first time as new metabolises by plant tissue cultures. A scheme for the biotransformation of progesterone (I) has been proposed, and the reduction and glucosidation activities distinctly have been observed in these cultured cells. 相似文献
13.
《Inorganica chimica acta》1986,125(4):197-201
Ten new diorganotin dichloride adducts of hormones of the type R2SnCl2·2L [where R = Me, Et, n-Bu, Oct and Ph; L = 4-androsten-17ß-ol-3-one (A); 5-androsten-3ß-ol-17-one (B); 4-androsten-17α- methyl-17ß-ol-3-one (C) and 3,17-dihydroxy-5- pregnene-20-one (D)] have been prepared and characterized at 297 K and 223 K. Spectroscopic measurements (IR; Raman; 1H, 13C, 119Sn NMR) suggest the dissociation or fast ligand exchange in solution at 297 K. Hexa-coordinated adducts with bonding through carbonyl oxygen and trans-R groups in octahedral geometry are formulated at 223 K. 相似文献
14.
I. Molnár N. Hayashi K.-P. Choi H. Yamamoto M. Yamashita Y. Murooka 《Molecular microbiology》1993,7(3):419-428
A new metabolite of cholesterol was found in reaction mixtures containing cholesterol or 4-cholesten-3-one as a substrate and extra- or intracellular protein extracts from recombinant Streptomyces lividans and Escherichia coli strains carrying cloned DNA fragments of Streptomyces sp. SA-COO, the producer of Streptomyces cholesterol oxidase. The new metabolite was identified as 4-cholesten-6-ol-3-one based on comparisons of its high-performance liquid chromatography, gas chromatography/mass spectrometry, infrared and proton-nuclear magnetic resonance spectra with those of an authentic standard. Genetic analyses showed that the enzyme responsible for the production of 4-cholesten-6-ol-3-one is cholesterol oxidase encoded by the choA gene. Commercially purified cholesterol oxidase (EC 1.1.3.6.) of a Streptomyces sp., as well as of Brevibacterium sterolicum and a Pseudomonas sp., and a highly purified recombinant Streptomyces cholesterol oxidase were also able to catalyse the 6-hydroxylation reaction. Hydrogen peroxide accumulating in the reaction mixtures as a consequence of the 3β-hydroxysteroid oxidase activity of the enzyme was shown to have no role in the formation of the 6-hydroxylated derivative. We propose a possible scheme of a branched reaction pathway for the concurrent formation of 4-cholesten-3-one and 4-chotesten-6-ol-3-one by cholesterol oxidase, and the observed differences in the rate of formation of the 6-hydroxy-ketosteroid by the enzymes of different bacterial sources are also discussed. 相似文献
15.
为了解柯拉斯那(Aquilaria crassna)的化学成分,从其所产沉香中分离得到10个化合物,经波谱分析分别鉴定为:6,8-羟基-2-(2-苯乙基)色酮(1),6,8-二羟基-2-[2-(4-甲氧基苯)乙基]色酮(2),rel-(1a R,2R,3R,7b S)-1a,2,3,7b-tetrahydro-2,3-dihydroxy-5-(2-phenylethyl)-7H-oxireno[f][1]benzopyran-7-one(3),rel-(1a R,2R,3R,7b S)-1a,2,3,7b-tetrahydro-2,3-dihydroxy-[2-(4-methoxyphenyl)-ethyl]-7H-oxireno[f][1]benzopyran-7-one(4),rel-(1a R,2R,3R,7b S)-1a,2,3,7b-tetrahydro-2,3-dihydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)-ethyl]-7H-oxireno[f][1]benzopyran-7-one(5),oxidoagarochromone B(6),oxidoagarochromone C(7),(5S,6R,7S,8R)-2-[2-(3′-hydroxy-4′-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone(8),6,7-cis-dihydroxy-2-(2-phenylethyl)-5,6,7,8-tetrahydrochromone(9),N-trans-feruloyltyramine(10)。化合物3~5和8~10为首次从柯拉斯那沉香中分离得到。化合物1,3,6,7,9和10对乙酰胆碱酯酶具有一定的抑制活性,化合物4对人慢性髓原白血病细胞株K-562和人胃癌细胞株SGC-7901均具有较小的抑制作用,化合物1和3对人肝癌细胞株BEL-7402也有抑制活性。 相似文献
16.
Yoshinobu Naoshima Yuichi Hayashi Itsuo Ichimoto Hiroo Ueda 《Bioscience, biotechnology, and biochemistry》2013,77(7):1393-1397
A new synthetic method of cyclotene (3-methyl-2-cyclopenten-2-ol-1-one) (I) and its derivatives has been investigated. The reaction of 2-cyclopenten-2-ol-1-one and aniline in toluene gave the corresponding ketimine derivative (V) in good yield. The methylation of (V) afforded (I) and 5,5-dimethyl-2-cyclopenten-2-ol-1-one (II) as the major reaction products, and 3,5-dimethyl-2-cyclopenten-2-ol-1-one (III) and 3,5,5-trimethyl-2-cyclopenten-2-ol-1-one (II) as the minor products. Similarly, ketimine derivative of (I) was alkylated with methyl iodide and ethyl iodide to yield the corresponding (II), (III), and 5-methyl-5-ethyl-2-cyclopenten-2-ol-1-one (VII), 3-methyl-5-ethyl-2-cyclopenten-2-ol-1-one (VIII), respectively, as the major products. 相似文献
17.
Estrogen-primed female rats were administered progesterone, 5 a-pregnan-3,20-dione, 5a-pregnan-3a-ol-20-one, 5a-pregnan-3β-ol-20-one, 4-pregnen-20a-ol-3-one, and 5a-pregnan-20a-ol-3-one in oil or oil alone and tested for the display of lordosis behavior 3 and 5 hr after progestin treatment. Progesterone was the most effective progestin in facilitating lordosis behavior. 5a-Pregnan- 3,20-dione and 5a-pregnan-3a-ol-20-one were partially effective, while the other progestins were no more effective than oil. The data suggest that the neuronal system which controls lordosis behavior is not entirely specific for progesterone. 相似文献
18.
为了解黄皮种子中的酰胺类生物碱及其杀线虫活性,运用多种色谱学及波谱学方法分离并鉴定了10个酰胺类生物碱,分别为:N-甲基桂皮酰胺(1),clausenalansamide A(2),3-dehydroxy-3-methoxyl-clausenalansamide A(3),clausenalansamide B(4),黄皮新肉桂酰胺B(5),N-(2-苯乙基)肉桂酰胺(6),2′-dehydroxy-2′-oxo-clausenalansamide B(7),lansamide-7(8),homoclausenamide(9),1,5-dihydro-5-hydroxy-1-methyl-3,5-diphenyl-2H-pyrrol-2-one(10)。其中,化合物3,7,10为新天然产物。首次对黄皮种子中的酰胺类生物碱2~8进行全齿复活线虫致死活性的测试,发现所测化合物均有致死活性,其中,化合物2,3,5和8有较强的致死活性,且均优于阳性对照除线磷,可为相关农药的研发提供科学依据。 相似文献
19.
Available online from an cytotoxic endophytic fungus Botryotinia fuckeliana A-S-3, three cytochalasans phenochalasin B (4), [12]-cytochalasin (5) and one [1,3] dioxacyclotridecino (6), along with two new ent-eudesmane sesquiterpenes, 1-keto-4α,15-epoxyeudesm-11-ol (1), and ent-4(15)-eudesmen-5,6-ol-1-one (2), and one known ent-eudesmane sesquiterpene ent-4(15)-eudesmen-11-ol-1-one (3) were isolated. The structures of these compounds were elucidated by interpretation of spectroscopic data. Among these compounds, two cytotoxic constituents were identified. 相似文献
20.
Halise Inci Gul Murat Cizmecioglu Sevil Zencir Mustafa Gul Pakize Canturk Mustafa Atalay 《Journal of enzyme inhibition and medicinal chemistry》2013,28(3):804-807
Chalcones (1,3-diaryl-2-propen-1-ones) are α, β-unsaturated ketones with cytotoxic and anticancer properties. Several reports have shown that compounds with cytotoxic properties may also interfere with DNA topoisomerase functions. Five derivatives of 4′-hydroxychalcones were examined for cytotoxicity against transformed human T (Jurkat) cells as well as plasmid supercoil relaxation experiments using mammalian DNA topoisomerase I. The compounds were 3-phenyl-1-(4′-hydroxyphenyl)-2-propen-1-one (I), 3-(p-methylphenyl)-1-(4′-hydroxyphenyl)-2-propen-1-one (II), 3-(p-methoxyphenyl)-1-(4′-hydroxyphenyl)-2-propen-1-one (III), 3-(p-chlorophenyl)-1-(4′-hydroxyphenyl)-2-propen-1-one (IV), and 3-(2- thienyl)-1-(4′-hydroxyphenyl)-2-propen-1-one (V). The order of the cytotoxicity of the compounds was; IV > III > II > I > V. Compound IV, had the highest Hammett and log P values (0.23 and 4.21, respectively) and exerted both highest cytotoxicity and strongest DNA topoisomerase I inhibition. Compounds I and II gave moderate interference with the DNA topoisomerase I while III & V did not interfere with the enzyme. 相似文献