北风菌中的甾体和甾体苷类化合物

摘要：从口蘑科真菌北风菌(Pleurotus ostreatus(Jacq．：Fr．)Kummer)的乙酸乙酯部分分离鉴定了12个甾体类化合物,其中包括8个麦角甾醇类甾体及4个甾体苷。利用现代波谱技术及化学方法,鉴定了一个新化合物3-O-β-D-glucopyranosyl-22E, 24R-ergosta-7, 22-diene-5a, 613, 9α-triolo 其余11个已知化合物分别为22E,24R-ergosta-7, 22-di-ene-3β, 5a, 6β3, 9α-tetraol, 3-O-β-D-glueopyranosyl-22E, 24R-ergosta-7, 22-diene-5α, 6β-diol、22E, 24R-ergosta-7, 22-di-ene-3β, 5α, 6β-triol, 22E, 24R-ergosta-5, 7, 22-tfien-3β-ol 3-O-β-D-glueopyranoside, ergosterol, 22E, 24R-ergosta-7, 22-dien-3β-ol 3-O-β -D-glueopyranoside, 22E, 24R-ergosta-7, 22-diene-3β-ol、 22E, 24R-ergosta-4, 6, 8, 22-tetraen-3-one、22E, 24R-ergosta-7, 22-diene-313, 5ct, 6a-tfiol, ergosterol peroxide 和 22E, 24R-ergosta-7, 22-diene-3β, 5α-diol-6-oneo     

槐生拜尔孔菌(槐耳)中的甾体类化合物及其酪氨酸酶抑制活性

本试验研究了槐生拜尔孔菌(槐耳)Vanderbylia robiniophila大米固体发酵物中的甾体类化合物及其酪氨酸酶抑制活性。采用硅胶柱层析、ODS柱层析、凝胶柱层析和高效液相色谱(high performance liquid chromatography,HPLC)等色谱法分离纯化槐生拜尔孔菌发酵产物,利用质谱(mass spectrometer, MS)、核磁共振(nuclear magnetic resonance, NMR)等方法进行结构鉴定得到10个甾体类化合物。化合物的结构分别鉴定为:isocyathisterol (1)、fortisterol (2)、7α-methoxy-5α,6α-epoxyergosta-8(14),22-diene-3β-triol (3)、(3β,5α,6β,22E)-6-methoxyergosta-7,22-diene-3,5-diol (4)、citreoanthrasteroid B (5)、(22E,24S)-5α,8α-epidioxy-24-methyl-cholesta-6,9(11),22-trien-3β-ol (6...     

飞蛾藤中的新C_(30)甾体类化合物(英文)

A novel C30 sterol, (22E, 24ξ)-24-n-propylcholest-7, 22-dien-3β-ol (racemosol, 1), along withscopoletin (2), scopolin (3), umbelliferone (4), methylβ-D-frucopyranoside (5), syringaresinol-4-O-β-D-glucopyranoside (6), quercetin-3-O-β-D-glucopyranoside (7), quercetin-3-O-α-L-rhamnopyranoside (8),eupatilin (9), kaempferol-3-O-β-D-glucopyranoside (10) and (E）-N-2-(2,3-dihydroxyphenyl) ethyl cinnamamide(11), was isolated from the whole plants of Porana racemosa Roxb. Their structures were elucidatedpredominantly by spectral evidence.     

开口箭根茎中甾体化合物的研究

从开口箭根茎部位共分离得到9个甾体化合物,经波谱数据分析结合文献对照分别鉴定为3-epi-neoruscogenin-3-β-D-glucopyranoside(1),3-epi-ruscogenin-3-β-D-glucopyranoside(2),ranmogenin A(3),convallagenin B(4),3-epi-neoruscogenin(5),tupichigenin E(6),(20S,22R)-spirost-25(27)-ene-1β,2β,3β,4β,5β,7α-hexaol-6-one(7),β-谷甾醇(8)和胡萝卜苷(9)。其中化合物1、2和4为首次从该植物中分离得到。     

知母中甾体皂苷类成分的研究(英文)

从中药知母(Anemarrhena asphodeloides Bge.)的70%乙醇提取物中分离得到6个化合物,经波谱学方法和与已知样品对照鉴定为:3-O-β-D-glucopyranosyl-(1→2)-β-D-galactopyranosyl-(3β,5β)-pregn-16(17)-ene-20-one(1)、timosaponin AIII(2)、timosaponin BIII(3)、22-hydroxy-5β-furost-3β,15α-diol-3-O-β-D-glucopyranosyl(1→2)-β-D-galactopyranoside(4)、timosaponin G(5)、β-daucosterol(6)。其中化合物1为新天然产物,命名为知母孕甾A,是知母中首次发现的C21甾体类化合物,经HR ESI-MS、1D NMR、2D NMR确定其结构,并首次对其核磁数据进行归属。     

拟白蘑子实体化学成分研究

从高等真菌拟白蘑(Tricholomopsis rutalis)干燥子实体的甲醇提取物中分离并鉴定了6个化合物,它们分别是软脂酸甲酯(1)、软脂酸(2)、麦角甾-5,7,22-三烯-3β-醇(3)、5α,8α-过氧化麦角甾-6,22-二烯-3β-醇(4)、麦角甾-7,22-二烯-3β,5α,6β-三醇(5)和5α,8α-过氧化麦角甾-6,22-二烯-3β-O-葡萄糖苷(6).以上化合物均为首次从拟白蘑中获得.     

亚稀褶黑菇的化学成分

从剧毒蘑菇─亚稀褶黑菇(Russula subnigricans Hongo)子实体中分离出5个已知化合物,经波谱分析鉴定为4个麦角甾醇(22E,24R)-ergosta-7,22-diene-3β,5α,6α,9α-tetraol(1)、(22E,24R)-ergosta-7,22-dien-3β,5α,9α-trihydroxy-6-one(2)、(22E,24R)-ergosta-7,22-dien-3β,5α,6β-triol(3)、(22E,24R)-5α,8α-epidioxyergosta-6,22-dien-3β-ol(4)和神经酰胺(2S,3S,4R,2′R)-2-(2′-hydroxytetracosanoylamino)octadecane-1,3,4-triol(5)。     

飞蛾藤中的新C30甾体类化合物

从毛叶飞蛾藤(Porana racemosa Roxb.)全草的95%乙醇提取物中分离并鉴定了11个化合物,其中一新的C30甾体化合物鉴定为(22E,24ξ)-24-正丙基胆甾-7,22-二烯-3β-醇(飞蛾藤素,1).其余10个已知化合物分别为东莨菪素(2)、东莨菪苷(3)、伞形华内酯(4)、β-D-甲基吡喃果糖苷(5)、丁香脂素4-O-β-D-吡喃葡萄糖苷(6)、斛皮素-3-O-β-D-吡喃葡萄糖苷(7)、斛皮素-3-O-α-L-吡喃鼠李糖苷(8)、异泽兰黄素(9)、山奈素-3-O-β-D-吡喃葡萄糖苷(10)和(E)-N-2-(2,3-二羟基苯基)乙基肉桂酰胺(11).     

黑刺菝葜中的甾体皂苷

从黑刺菝葜(Smitax scobinicaulis C.H.Wringh)根茎中再次分离得到2个新的甾体皂苷化合物,经理化、光谱分析及与标准样品对照,鉴定化合物Ⅲ为(25D)螺甾-5-烯-3β,17α,27-三羟基-3-O-β-D-吡喃葡萄糖-(1→4)-O-[α-L-吡喃阿拉伯糖(1→6)]-β-D-吡喃葡萄糖甙。化合物Ⅳ为(25D)螺甾-3β,17α,27-三羟基-3-O-β-D-吡喃葡萄糖-(1→4)-O-[α-L-吡喃阿拉伯糖(1→6)]-β-D-吡喃葡萄糖甙。     

苦竹内生真菌Fusarium sp. S13的化学成分研究(英文)

从苦竹内生真菌Fusarium sp.S13的发酵液提取物中分离得到8个化合物,通过波谱技术分别鉴定为:cerevisterol(1),(22E,24S)-24-methyl-5α-cholesta-7,22-diene-3β,5α,6β,9α-tetraol(2),ergosterol peroxide(3),3β,5α,9α-trihydroxy-6β-methoxyergosta-7,22-dien(4),ergosta-7,22-dien-6β-methoxy-3β,5α-diol(5),ergosta-4,6,8(14),22-tetraen-3-one(6),25-hydroxy-ergosta-4,6,8(14),22-tetraen-3-one(7),ergosta-7,22-dien-3β,6β-diol(8)。海虾致死实验结果显示化合物1-8均显示出不同程度的毒性。     

4-Desmethylsterol composition of citrus rootstocks of different salt exclusion capacity

Fibrous roots from seedlings of three citrus rootstocks (Rungpur lime, Kharna khatta and Etrog citron) grown hydroponically for 6 weeks in the presence or absence of 50 mM NaCl were analysed for their content of free, esterified, and glycosidic sterols. Leaf chloride analyses indicated that Rangpur lime was a good Cl- excluder and the other two rootstocks were Cl- accumulators.
On a dry weight basis and in the absence of NaCI only the free 4-desmethyIsterol levels showed significant rootstock differences. Kharna khatta had the highest, and Rangpur lime the lowest, free stcrol levels. Sitostcrol was the major component of all sterol fractions of Rangpur lime, the esterified fraction of the other rootstocks, and the glycosidic sterol fraction of Kharna khatta. The ratio of sitosterol to stigmasterol was highest in Rangpur lime and lowest in Etrog citron in all cases and the ratio of apos;more-planar apos; to apos;less-planar apos; free sterols was highest in Etrog citron and lowest in Rangpur lime.
Treatment with 50 mM NaCI resulted in an increase in free sterol levels in Rangpur lime and a decrease in Kharna khatta. Steryl ester levels were unaffected in Rangpur lime but were significantly reduced in the other rootstocks. In all three sterol fractions the sitosterol/stigmasterol ratio was decreased. A decrease in the ratio of apos;more-planarapos; to apos;less-planarapos; free sterols was observed only in Kharna khatta and, more notably, Etrog citron. Salt-induced changes in the apos;more-planar apos; to apos;less-planar apos; free sterol ratio correlated well with salt exclusion capacity.     

STEROLS OF CEPHALEUROS (TRENTEPOHLIACEAE), A PARASITIC GREEN ALGA1

24-Ethylcholesterol, 24-ethylcholesta-5,7,22-trienol, dihydrolanosterol, 24-ethylcholesta-7,22-dienol, and 4-methyl-24-ethylcholesta-7,22-dienol were identified in cultured Cephaleuros in small quantities. Cholesterol made up 19% of the total sterol. The principal sterol, making up 65% of the total sterol, was 4,24-dimethylcholest-7-enol, a new algal sterol. This is the first report of this sterol as the principal sterol of any living organism.     

In vivo conversion of [4-14C]sitosterol and [22,23-3H]sitosterol to stigmasterol in barley seedlings

Six-day-old barley seedlings were allowed to take up [4-¹⁴C]sitosterol and [22, 23-³H]sitosterol for 2.5 hr and the incorporation into the sterol fractions was determined after 0, 6, 12 and 24 hr. Sitosterol was readily incorporated into every sterol class. The ³H/¹⁴C ratio in the free forms dropped when compared with the ³H/¹⁴C ratio of the administered sitosterol. In the free sterol, radioactive stigmasterol, showing a ³H/¹⁴C ratio half that of the sitosterol ³H/¹⁴C ratio, was isolated and its radiochemical purity established by dilution with carrier material and crystallization to constant specific activity.     

A simple synthesis of 3β-acetoxy-20-oxomethylpregn-5-ene and 3β-acetoxy-20-hydroxymethylpregn-5-ene

3β-Acetoxy-20-oxomethylpregn-5-ene and 3β-acetoxy-20-hydroxymethylpregn-5-ene were synthesized from (22R, 23R)-sitost-5-ene-3β,22,23-triol in 66% overall yields.     

Sterols from some sponges

The sterol composition of four sponges was determined by a combination of gas chromatography and mass spectrometry. Cliona viridis and Chondrosia reniformis contained mainly C₂₇-C₂₉Δ⁵ mono- and di-unsaturated sterols. Halichondria bowerbanki and Hymeniacidon sanguinea contained stanols and Δ⁵-sterols. Cholestanol was the major component of the sterol mixtures.     

Sterols from some black sea ulvaceae

The free and esterified sterol composition of Ulva rigida and Enteromorpha linza (Ulvaceae) from the Black Sea was investigated. The main sterol component of Ulva rigida was identified as fucosterol. The influence of the season and water pollution on the sterol composition was investigated. The origin of the C₂₆,- and C₂₅-sterols and of saringasterol in these seaweeds is discussed.     

Composition sterolique et morphogeneses reproductrices chez Gnomonia leptostyla

Sterol components of Gnomonia leptostyla mycelia have been investigated from in vitro cultures in which sexual and asexual morphogenesis are induced by temperature and light conditions. The nature and content of free sterols and sterol esters were determined by MIKE spectrometry. Relations between sterol composition (total sterols; Δ^5,7 and Δ⁵ sterols) and reproductive morphogenesis are discussed, particularly with respect to the degree of sexuality induced.     

Effects of diet and metamorphosis upon the sterol composition of the butterfly Morpho peleides

Whole body sterol metabolism in insects has seldom been studied. We were able to design an appropriate study at a butterfly farm in Belize. We collected six larvas of butterfly (Morpho peleides), their food (leaves of Pterocarpus bayessii), and their excretions. In addition, six adult butterflies were collected. The sterols of the diet, the larva, and adult butterfly were analyzed by gas-liquid chromatography. The structures of these sterols were identified by digitonin precipitation, GC-MS, and NMR. Four sterols (cholesterol, campesterol, stigmasterol, and sitosterol) and a sterol mixture were found in the food, the body, and the excreta of the larva. The tissue sterol content of the larva was 326 microg. They consumed 276 microg of sterols per day. Their excretion was 185 microg per day as sterols. The total tissue sterol contents of the larva and butterfly were similar, but they had different sterol compositions, which indicated interconversion of sterols during development. There was a progressive increase in the cholesterol content from larva to butterfly and a decrease in the content of sitosterol and other plant sterols, which were likely converted to cholesterol. Our data indicated an active sterol metabolism in butterfly larva. Diet played an important role in determining its sterol composition. During metamorphosis, there was an interconversion of sterols. This is the first paper documenting the fecal sterol excretion in insects as related to dietary intakes.     

Composition of the sterol fraction in horse chestnut

The Δ⁷-and Δ⁵-sterol fractions were isolated from the unsaponifiable matter of ripe, air dried, chestnut seed. The Δ⁷-sterol fraction amounted to 18.4% and the Δ⁵-sterol fraction amounted to 8.2% of the unsaponifiable matter. In the Δ⁷-sterol fraction three components were identified as Δ⁷-campesterol, α-spinasterol and Δ⁷-stigmastenol. One component was probably Δ^5,7-stigmastadienol and five components remained unidentified. Δ⁷-stigmastenol and α- spinasterol were the major components and amounted to 74.8% of the fraction. In the Δ⁵-sterol fraction at least ten components were found. Five of them were identified as cholesterol, campesterol, stigmasterol, sitosterol and Δ⁴-stigmasten-3-one. Stigmasterol and sitosterol amounted to 73.6% of the fraction.     

Sterols and steryl esters in some Brassica and Sinapis seeds

The qualitative and quantitative composition of sterols in the free form and esterified to fatty acids was studied in seed oils from Brassica napus, B. campestris, B..iuncea, B. nigra, Sinapis alba and S. aruefisis (Brassica kaber). Sitosterol, followed by campesterol, predominated in both the free and the esterified sterols. The free sterols were richer in brassicasterol (ca 10–20%) than the steryl esters (3–10%). Small amounts of δ⁵-avenasterol and δ⁷-stigmastenol were also found in the Brassica oils, often more in the esterified than in the free form. The quantity of sterols was studied only in Brassica campestris, which had ca 0.3 % in the free as well as in the esterified form. In Sinapis alba, ca 10% of the sterols in the free form and 20 % in the esterified sterols were δ⁵-avenasterol. This compared to only a few per cent in both the free and esterified sterols in the Brassica oils. Similarly, ca 2 % of cholesterol was found among the sterols of Sinapis alba but only traces in the Brassica oils. The similarity of sterol compositions among the cultivated brassicas and wild mustard (Sinapis arvensis), and the specific characteristics of the sterols in white mustard (Sinapis alba) adds further weight to the suggestion that wild mustard should be treated as Brassica kaber and strengthens the generic separation of Sinapis alba.