共查询到20条相似文献,搜索用时 31 毫秒
1.
From the extract of the fruits of Solanum xanthocarpum (Solanaceae), five new steroidal compounds were isolated and characterized: 4α-methyl-24ξ-ethyl-5α-cholest-7-en-3β,22ξ-diol (1), 3β,22ξ-dihydroxy-4α-methyl-24ξ-ethyl-5α-cholest-7-en-6-one (2), 3β-benzoxy-14β,22ξ-dihydroxy-4α-methyl-24ξ-ethyl-5α-cholest-7-en-6-one (3), 3β-benzoxy-14α,22ξ-dihydroxy-4α-methyl-24ξ-ethyl-5α-cholest-7-en-6-one (4) and 3β-(p-hydroxy)-benzoxy-22ξ-hydroxy-4α-methyl-24ξ-ethyl-5α-cholest-7-en-6-one (5). 相似文献
2.
A series of 7α- and 7β- alkyl derivatives of steroidal 4-en- and 5-en-3-ones were prepared by 1,6-conjugate addition of organocopper reagents to various steroidal 4,6-dien-3-ones of the androstane, estrane and gonane series. Biological study of these and related compounds revealed that 17β-hydroxy-7α-methyl-5-androsten-3-one (2), 17β-hydroxy-7α-methyl-5-estren-3-one acetate and 17β-hydroxy-7α-methyl-4-estren-3-one acetate had significant anti-implantational and antidecidual activities. The contragestative effects were associated with the latter antihormonal properties, and not with the androgenicity of these compounds. 相似文献
3.
The potential for biotransformation of the substrate 17β-hydroxyandrost-4-en-3-one (testosterone) by six filamentous fungi, namely, Rhizopus oryzae ATCC 11145, Mucor plumbeus ATCC 4740, Cunninghamella echinulata var. elegans ATCC 8688a, Aspergillus niger ATCC 9142, Phanerochaete chrysosporium ATCC 24725 and Whetzelinia sclerotiorum ATCC 18687, was investigated. In this study both free cells and macerated mycelia immobilised in calcium alginate were utilised and the results (products, % yields, % transformation) were compared. In general the encapsulated cells of the microorganisms effectively generated products similar to those found using free cells. However, with immobilised macerated mycelia, isolation of the transformation products was expedited by the simple work up procedure, and their purification was facilitated by the absence of fungal secondary metabolites. Twenty seven analogues of testosterone were generated, wherein the androstane skeleton was functionalised at C-1β, -2β, -6β, -7α, -11α, -14, -15α, -15β and -16β by the moulds. Redox chemistry was also observed. Seven of the analogues, 6β,11α,17β-trihydroxyandrost-4-en-3-one, 6β,14α,17β-trihydroxyandrost-4-en-3-one, 2,6β-dihydroxyandrosta-1,4-diene-3,17-dione, 2β,16β-dihydroxyandrost-4-ene-3,17-dione, 2β,6β-dihydroxyandrost-4-ene-3,17-dione, 2β,15β,17β-trihydroxyandrost-4-en-3-one and 2β,3α,17β-trihydroxyandrost-4-ene, were novel compounds. Five others, namely, 7α,17β-dihydroxyandrost-4-en-3-one, 6β,14α-dihydroxyandrost-4-ene-3,17-dione, 15α,17β-dihydroxyandrost-4-en-3-one, 16β,17α-dihydroxyandrost-4-en-3-one and 2β,16β,17β-trihydroxyandrost-4-en-3-one, were fully characterised for the first time. 相似文献
4.
二萜佛司可林I、J、K、L,已从毛喉鞘蕊花分离得到。本文根据一维和二维的核磁共振谱详细描述了它们的光谱特征,二萜佛司可林K、L是首次报道。 相似文献
5.
本文对采自海南三亚海域的疏枝刺柳珊瑚(Echinogorgia pseudossapo)化学成分进行研究,分离到11个甾醇类化合物。经波谱数据分析,分别鉴定为cholest-5-en-3β-ol(1),24-methylene-cholest-4-ene-3β,6β-diol(2),24-norcholesta-22-en-3β-ol(3),acanthovagasteroid A(4),calicoferol E(5),calicoferol F(6),6-hydroxy-cholest-4-ene-3-one(7),echinoflorasterol(8),echissaposterol(9),24-methylcholest-5-en-3β,7α-diol(10)和24-methylcholest-5,22(E)-dien-3β,7α-diol(11)。除化合物8外,其余化合物均首次从该种海洋动物中分离得到。 相似文献
6.
云南割舌树的化学成分 总被引:4,自引:0,他引:4
从云南割舌树(Walsura yunnanensis C.Y.Wu.)树皮的乙醇提取物中分离鉴定了12个化合物,它们分别是walsurol(1),tocopherol(2),sitoindoside Ⅰ(3),3β-stigmast-5-en-3-yl-β-D-xylopyranoside(4),stigmast-4-en-6β-ol-3-one(5),7-oxositosterol(6),3β-hydroxy-5α,8α-epidioxyergosta-6,22-diene(7),(-)epicatechin(8),3,5-dihydroxy-4-methoxylphenylethanol(9),间三甲氧基苯,(β-谷甾醇和胡萝卜甙,新化合物1命名为割舌醇(walsurol)。 相似文献
7.
8.
从肋果茶(Sladenia celastrifolia)95%乙醇提取物的乙酸乙酯部位中分离得到15个萜类化合物,经波谱学方法分别鉴定为sladeniafolin A(1),grasshopper ketone (2),(3S,5R,6S,7E,9R) -7-megastigmene-3,6,9-triol (3),hedytriol (4),(3S,5R,6R,7E,9R) -3,5,6,9-tetrahydroxy-7-megastigmene(5),1′S*,4′R*-8-(4′-hydroxy-2′,6′,6′-trimethylcyclohex-2-enyl)-6-methyloct-3E,5E,7E-trien -2-one (6),2α,3α,19α,23-tetrahydroxyurs-12-en-28-oic acid (7),2α,3β,19α,23-tetrahydroxyurs-12-en-28-oic acid(8),pomolic acid(9),3-O-acetyl pomolic acid(10),ursaldehyde (11),camarolide (12),3β-hydroxyurs-11-en-13β(28) -olide (13),3β-hydroxy -11α,12α-epoxy-urs-13β,28-olide (14)和28-0-β-D-glucopyranosyl euscaphic acid (15).以上化合物均首次从该植物中分离得到,其中1为新的C9裂环烯醚萜. 相似文献
9.
Edward J. Parish Mitsuhiro Tsuda George J. Schroepfer 《Chemistry and physics of lipids》1979,24(3):209-236
The chemical syntheses of a number of 14α-alkyl substituted 15-oxygenated sterols have been pursued to permit evaluation of their activity in the inhibition of the biosynthesis of cholesterol and other biological effects. Described herein are the first chemical syntheses of 14α-ethyl-5α-cholest-7-en-3β-ol-15-one, bis-3β,15α-acetoxy-14α-ethyl-5α-cholest-7-ene, 3β-acetoxy-14α-ethyl-5α-cholest-7-en-15β-ol, 14α-ethyl-5α-cholest-7-en-3β,15β-diol, 14α-ethyl-5α-cholest-7-en-3β,15α-diol, 3β-hexadecanoyloxy-14α-ethyl-5α-cholest-7-en-15α-ol, 3β-hexadecanoyloxy-14α-ethyl-5α-cholest-7-en-15β-ol, bis-3β,15α-hexadecanoyloxy-14α-ethyl-5α-cholest-7-ene, 3β-hexadecanoyloxy-14α-ethyl-5α-cholest-7-en-15-one, 3α-benzoyloxy-14α-ethyl-5α-cholest-7-en-15-one, 14α-ethyl-5α-cholest-7-en-3α-ol-15-one, 14α-ethyl-5α-cholest-7-en-15-on-3β-yl pyridinium sulfate, 14α-ethyl-5α-cholest-7-en-15-on-3β-yl potassium sulfate (monohydrate), 14α-ethyl-5α-cholest-7-en-15-on-3α-yl pyridinium sulfate, 14α-ethyl-5α-cholest-7-en-15-on-3α-yl potassium sulfate (monohydrate), 3β-ethoxy-14α-ethyl-5α-cholest-7-en-15-one, 3β-acetoxy-14α-n-propyl-5α-cholest-7-en-15-one, 14α-n-propyl-5α-cholest-7-en-3β-ol-15-one, bis-3β, 15α-acetoxy-14α-n-propyl-5α-cholest-7-ene, 3β-acetoxy-14α-n-propyl-5α-cholest-7-en-15β-ol, 14α-n-propyl-5α-cholest-7-en-3β, 15α-diol, 14α-n-propyl-5α-cholest-7-en-3β, 15β-diol, 14α-n-butyl-5α-cholest-7-en-3β-ol-15-one, 3β-acetoxy-14-α-n-butyl-5α-cholest-7-en-15-one, bis-3β,15α-acetoxy-14α-n-butyl-5α-cholest-7-ene, 3β-acetoxy-14α-n-butyl-5α-cholest-7-en-15β-ol, 14α-n-butyl-5β-cholest-7-en-3β, 15β-diol, and 14α-n-butyl-5α-cholest-7-en-3β, 15α-diol. 相似文献
10.
The thermal decomposition of the allylic alcohols 5α-cholest-6-ene-3β,5-diol, cholest-5-ene-3β,7α-diol, and cholest-5-ene-3β,7β-diol and of the allylic hydroperoxides 3β-hydroxy-5α-cholest-6-ene-5-hydroperoxide, 3β-hydroxycho lest-5-ene-7α-hydroperoxide, and 3β-hydroxycholest-5ene-7β-hydroperoxide to six common major pyrolysis products cholest-5-ene-3β,7α-diol, cholest-5-ene-3β,7β-diol, 3β-hydroxycholest-5-en-7-one, cholesta-3,5-dien-7-one, cholesta-4,6-dien-3-one, and cholesta2,4,6-triene was established. 相似文献
11.
《Phytochemistry》1999,52(8):1581-1585
Two serratane triterpenoids were isolated from the stem bark of Picea jezoenis var. hondoensis, together with two known compounds, 3β-methoxyserrat-14-en-21-one and 3β-methoxyserrat-14-en-21α-ol. The serratane triterpenoids were characterized as 14β,15β-epoxy-3α-methoxyserratan-21β-ol and 3α-methoxy-21β-hydroxyserrat-14-en-16-one, on the basis of chemical and spectroscopic evidence. 相似文献
12.
Inhibition of sterol synthesis in L cells by 14alpha-ethyl-5alpha-cholest-7-en-15alpha-ol-3-one at nanomolar concentrations 总被引:1,自引:0,他引:1
G J Schroepfer D L Raulston A A Kandutsch 《Biochemical and biophysical research communications》1977,79(2):406-410
14α-Ethyl-5α-cholest-7-en-15α-ol-3-one was prepared in 85% yield by selective oxidation of the 3β-hydroxyl function of 14α-ethyl-5α-cholest-7-en-3β,15α-diol by cholesterol oxidase. 14α-Ethyl-5α-cholest-7-en-15α-ol-3-one caused a 50% inhibition of the incorporation of [1-14C]-acetate into digitonin-precipitable sterols at a concentration of 6 × 10?9M in L cells and a 50% reduction in level of 3-hydroxy-3-methyl-glutaryl coenzyme A reductase activity in the same cells at a concentration of 4 × 10?8 M. 相似文献
13.
Treatment of 3β-benzoyloxy-14α, 15α-epoxy-5α-cholest-7-ene with boron trifluoride-etherate gave, in 43% yield, 3β-benzoyloxy-5α, 14β-cholest-7-en-15-one with the unnatural C ring juncture. Reduction of the latter compound with lithium aluminum hydride gave 15α, 14β-cholest-7-en-3β, 15α-diol and 5α, 14β-cholest-7-en-3β, 15β-diol in 9% and 81% yields, respectively. 相似文献
14.
石山巴豆( Croton euryphyllus)为大戟科( Euphorbiaceae)巴豆属( Croton)植物,主要分布于西南各省的岩溶石山地区,民间用于杀虫和治疗跌打损伤。为了阐明其化学物质基础,该研究采用硅胶柱层析、Sephadex LH-20、HPLC等方法对石山巴豆枝叶醇提物进行分离纯化。结果表明:共分离得到16个化合物,分别鉴定为异毛叶巴豆萜(1), jatrophoidin (2),山藿香定(3),异山藿香素(4),山藿香素(5),赖百当-13-烯-8,15-二醇(6),7-酮基-β-谷甾醇(7),(22E)-5α,8β-表二氧麦角甾-6,22-二烯-3β-醇(8),豆甾烷-4-烯-6β-醇-3-酮(9),齐墩果烷-12-烯-2α,3β-二醇(10),东莨菪内酯(11),催吐萝芙木醇(12), lyratol F (13),罗布麻酚A (14),芹菜素(15),金色酰胺醇酯(16)。所有化合物均为首次从该植物中分离得到,其中化合物8-16为首次从巴豆属中发现。 相似文献
15.
The aim of this study was to synthesize different ester derivatives of dehydroepiandrosterone with therapeutic potential as antiandrogens.The biological effect of these steroids was demonstrated in in vivo as well as in vitro experiments. In the in vivo experiments, we measured the activity of seven steroids on the weight of the prostate and seminal vesicles of gonadectomized hamsters treated with testosterone. For the in vitro studies, we determined the IC50 values by measuring the concentration of the steroidal derivatives that inhibits 50% of the activity of 5α-reductase present in human prostate and also its binding capacity to the androgen receptors (AR) obtained from rat’s prostate cytosol. The results from these experiments indicated that compounds 7 5α,6β-dibromo-3β-propanoyloxyandrostan-17-one, 8 5α,6β-dibromo-3β-butanoyloxyandrostan-17-one and 9 5α,6β-dibromo-3β-(3′-oxapentanoyloxy)-androstan-17-one, significantly decreased the weight of the prostate and seminal vesicles as compared to testosterone treated animals; this reduction of the weight of these glands was comparable to that produced by Finasteride 11. On the other hand, compounds 4 3β-acetoxyandrost-5-en-17-one, 5 3β-hexanoyloxyandrost-5-en-17-one 6 3β-(3′-oxapentanoyloxy)-androst-5-en-17-one, 7 and 12 dehydroepiandrosterone, (commercially available) inhibited the enzyme 5α-reductase. Compounds 4, 5, 6, 8 and 9 (IC50 values of 5.2 ± 1.2, 0.049 ± 0.002, 6.4 ± 1.1, 0.10 ± 0.045, and 6.8 ± 0.9 nM, respectively) exhibited the highest inhibitory activity. However, none of these compounds binds to the AR. 相似文献
16.
Li-Hong Shan Hong-Min Liu Ke-Xue Huang Gui-Fu Dai Chen Cao Rui-Jing Dong 《Bioorganic & medicinal chemistry letters》2009,19(23):6637-6639
A series of novel 3β, 7α, 11α-trihydroxy-pregn-21-benzylidene-5-en-20-one derivatives were synthesized and characterized by NMR, HRMS. The pregnenolone (1) was first biotransformed by Mucor circinelloides var lusitanicus to 3β, 7α, 11α-trihydroxy-pregn-5-en-20-one (3), then 3 was treated with various benzaldehydes to produce 3β, 7α, 11α-trihydroxy-pregn-21-benzylidene-5-en-20-one derivatives. These derivatives showed remarkable activity against EC109 cells. The absolute configuration of 3 was also confirmed by signal-crystal X-ray analysis. 相似文献
17.
The pattern of androgenic metabolites in blood, muscle, caput and cauda epididymidis has been investigated in functionally hepatectomized 24 hours castrated rats, 3 hours after the intra-muscular injection of 200 μCi of 3H -3α-diol. Identification of the radioactive metabolites showed only negligible differences between the epididymal regions. In both caput and cauda the main metabolite was DHT (17β-hydroxy-5α-androstane-3-one); 3α- and 3β-diol, androsterone (3α-hydroxy-5α-androstane-17-one), 5-A-dione (5α-androstane-3,17-dione), Δ16-3α-ol (5α-androst-l6-en-3α-ol), Δ16-3β-ol (5α-androst-l6-en-3α-ol) and Δ16-3-one (5α-androst-l6-en-3-one) were also present. and were the predominant metabolites in blood and muscle. No Δ16 compounds could be detected and in constrast to epididymis, more than 50% of the radioactivity was associated with polar compounds. From determination of total radioactivity, it was seen that retention by epididymis varied from two to four times that of muscle. Purification and identification of the radioactivity associated with the nuclear fraction demonstrated that DHT was the only nuclear bound androgen.It is suggested from these results that at least one effect of 3α-diol on the rat epididymis is exerted through its conversion to DHT. 相似文献
18.
Progesterone-4-14C was extensively metabolized during incubation with dispersed trophoblast prepared from chorionic membranes of the 21-day sheep conceptus. Of the metabolites formed, 17,20α-dihydroxypregn-4-en-3-one, 20α-hydroxypregn-4-en-3-one, 20(β-hydroxypregn-4-en-3-one, 5α-pregnane-3α,17,20α-triol, 5β-pregnane-3ga, 17,20α-triol, 5β-pregnane-3g,20α-diol, 3β-hydroxy-5α-pregnan-20-one, 3α-hydroxy-5β-pregnan-20-one, 20β-hydroxy-5β-pregnan-3-one, 5α-pregnane-3,20-dione and 5β-pregnane-3,20-dione were identified. These findings indicate that the sheep conceptus acquires extensive steroid metabolizing capability very early in pregnancy. 相似文献
19.
R. P. Litvinovskaya A. V. Baranovsky M. A. Averkova V. A. Khripach 《Russian Journal of Bioorganic Chemistry》2007,33(3):320-325
Androstane and Δ15-androstane analogues of brassinosteroids were synthesized from dehydroepiandrosterone. The key stage, hydroxylation of 17β-acetoxyandrost-2-en-6-one double bond with OsO4, yielded the corresponding 2α,3α-and 2β,3β-diols. The target 2α,3α-isopropylidenedioxy-6,6-ethylenedioxy-5α-androst-15-en-17-one and its 2β,3β-isomer were obtained by dehydrosilylation of the corresponding silylenol ethers with palladium acetate. 相似文献
20.
George J. Schroepfer Edward J. Parish Alemka Kisic Dianne M. Frome Andrew A. Kandutsch 《Chemistry and physics of lipids》1981,29(3):201-211
The chemical syntheses of 5α-cholestane-3β,14α,15β-triol, 5α-cholestane-14α-ol-3,15-dione, 5α-cholestane-3β,14α-diol-15-one, 14α,15α-epoxy-5α-cholestan-3β-ol, and 5α-cholest-8(14)-en-3β-ol-15-one oxime are described. All of these compounds were found to be potent inhibitors of sterol synthesis in cultured mouse L cells. However, the former three compounds had little or no effect on the levels of 3-hydroxy-3-methylgutaryl (HMG)-CoA reductase in the same cells. In contrast, in the case of the latter two compounds, the concentrations required to cause a 50% inhibition of the synthesis of digitonin-precipitable sterols were comparable to those required to cause a 50% reduction in the levels of HMG-CoA reductase in the same cells. 5α-Cholest-8(14)-en-3β-ol-15-one oxime had no effect on serum cholesterol levels when administered to male rats at a level of 0.15% in a cholesterol-free diet. 相似文献