Pregnane glycosides from Solanum nigrum

Two new pregnane saponins, solanigroside A (1) and solanigroside B (2), along with two known compounds (3 and 4), were isolated from 60% ethanolic extract of the dried herb of Solanum nigrum L. The structures of 1 and 2 were elucidated as 5alpha-pregn-16-en-3beta-ol-20-one 3-O-beta-D-xylopyranosyl-(1 --> 3)-O-[alpha-L-arabinopyranosyl-(1 --> 2)]-O-beta-D-glucopyranosyl-(1 --> 4)-O-[alpha-L-rhamnopyranosyl-(1 --> 2)]-O-beta-D-galactopyranoside (1) and 5alpha-pregn-16-en-3beta-ol-20-one 3-O-beta-D-glucopyranosyl-(1 --> 2)-O-[beta-D-glucopyranosyl-(1 --> 3)]-O-beta-D-glucopyranosyl-(1 --> 4)-O-beta-D-galactopyranoside (2), respectively, on the basis of extensive spectroscopic analysis as well as comparison with reported spectroscopic data of related compounds. This paper deals with the isolation and structural characterisation of pregnane glycosides from S. nigrum L.     

A new chromone and a new aliphatic ester isolated from Daldinia eschscholtzii

Abstract

A new chromone and a new aliphatic ester were isolated from the EtOAc extract of myceliums of Daldinia eschscholtzii. Their structures were elucidated as (R)-5-hydroxy-8-methoxy-2-methylchroman-4-one (1) and (E)-6-(non-3-en-1-yl) -2H-pyran-2-one (2) by interpretation of the spectroscopic evidence.     

A new bisabolane sesquiterpenoid from Euphorbia chrysocoma

The new sesquiterpenoid (6R)-2-chloro-6-[(1S)-1,5-dimethylhex-4-en-1-yl]-3-methylcyclohex-2-en-1-one (1), together with ten known compounds, (6R)-6-[(1S)-1,5-dimethylhex-4-en-1-yl]-3-methylcyclohex-2-en-1-one (2), bauerenol acetate (3), lupenone (4), alpha-amyrenone (5), beta-sitosterol (6), stigmasterol (7), beta-amyrin (8), ursolic acid (9), betulinic acid (10), scopolin (11), have been isolated from the roots of Euphorbia chrysocoma Lévl. et Vant. Their structures have been elucidated by spectroscopic data.     

6-hydroxy-4-en-3-one sterols from the marine sponge Iotrochoto birotulata

Five sterols with a nucleus skeleton of 6-hydroxy-4-en-3-one, namely cholesta-6beta-hydroxy-4-en-3-one (1), ergosta-6beta-hydroxy-4,24(28)-dien-3-one (2), ergosta-6alpha-hydroxy-4,24(28)-dien-3-one (3), ergosta-6alpha-hydroxy-4,22-E-dien-3-one (4), and ergosta-28-methyl-6beta-hydroxy-4,24(28)-dien-3-one (5) have been isolated from the marine sponge Iotrochoto birotulata, collected from the southern China sea. Sterols 2-4 are new compounds, and 1 has been isolated from marine organisms for the first time. The structures have been elucidated on the basis of extensive spectroscopic and chemical properties.     

江南卷柏的化学成分

从江南卷柏（Selaginella mollendorfii Hieron.）全草中分离并鉴定了15个化合物,分别为：扁柏双黄酮（1）,穗花杉双黄酮（2）,2,3-dihydroamentoflavone（3）,银杏双黄酮（4）,去甲基银杏双黄酮（5）,罗汉松双黄酮 A （6）,7-O-methylamentoflavone （7）,5-carboxymethyl-7,4′-dihydroxyflavone （8）,5-carboxymethyl-7,4′-dihydroxyflavanone （9）,大黄素甲醚（10）,大黄素（11）,大黄酸（12）,stigmast-4-en-3-one （13）,6β-hydroperoxystigmast-4-en-3-one （14）, anabellamide（15）。其中化合物10~15为首次从该植物中分离得到。     

Cytotoxic triterpenes from Ligulariopsis shichuana

Five olean-12-ene triterpenes (1-5) were isolated from the whole plant of Ligulariopsis shichuana. Their structures were elucidated by spectroscopic methods, including IR, EIMS positive HRSIMS, 1DNMR, and 2DNMR. Among them, 16beta,28-dihydroxyolean-12-en-3-one (3), olean-12-en-3beta,6beta,16beta,28-tetraol (4), 6beta,16beta-dihydroxyolean-12-en-3-one (5) are new compounds. In addition, compounds 4 and 5 showed cytotoxic activities on human hepatomacells (SMMC-7721), human ovarian neoplasm cells (HO-8910) and human hepatocytes cells (LO2).     

中国南海海绵Spheciospongia sp.中的甾体化合物

目的研究中国南海海绵Spheciospongia sp.的化学成分。方法采用多种色谱方法分离纯化,依据理化性质、波谱数据和文献对照的方法鉴定结构。结果从中国南海海绵Spheciospongia sp.石油醚提取物中分离鉴定了6个甾体类化合物:胆甾醇(cholesterol,1),胆甾-4-稀-3-酮(cho-lest-4-en-3-one,2),胆甾-3,6-二酮(cholest-3,6-dione,3),3β-羟基-胆甾-5-稀-7-酮(3β-hydroxy-cholest-5-en-7-one,4),6β-羟基-胆甾-4-稀-3-酮(6β-hydroxy-cholest-4-en-3-one,5),胆甾-3β,5α,6β-三醇(cholest-3β,5α,6β-triol,6)。结论化合物2-6为首次从该属海绵中分离得到。     

Biotransformation of dehydroparadols byAspergillus niger

To prove uniqueness of allylic alcohol formation from α,β-unsaturated ketones by mammal enzymes, a metabolic pattern of dehydroparadols, non-pungent synthetic analogs of shogaol byAspergillus niger was examined. Two biotransformation products of a dehydroparadol, 1-(4-hydroxy-3-methoxyphenyl)-non-1-en-3-one were accumulated in the culture broth ofA. niger. They were characterized as 1-(4-hydroxy-3-methoxyphenyl)-non-1-en-9-ol-3-one and 1-(4-hydroxy-3-methoxyphenyl)-nonan-9-ol-3-one by UV, NMR and mass spectroscopic analyses. Accumulation of allylic alcohol metabolites was not observed.     

Triterpene Saponins from Xeromphis nilotica

Photo-diode-array detector-assisted RP- and NP-HPLC analysis of a methanol extract of the seeds of Centaurea moschata L. (Compositae) led to the isolation of a novel steroidal glucoside which, on the basis of spectroscopic evidence, was identified as (20 R) -15a-hydroxy-8ß, 9a, 14a, 17a-pregn-4-en-3-one 20- O -ß-D-Glucopyranoside [1].     

Two new phenol derivatives from Stereum hirsutum FP-91666

Two new phenol derivatives, 2-(3-methyl-2-buten-1-yl)-4-methoxyethyl-phenol (1) and 5-hydroxy-4-(hydroxymethyl)-2-(3-methylbut-2-en-1-yl)cyclohex-4-en-1-one (2), together with eight known compounds consisting of phenol derivatives (3 and 4), niacinamide (5), and five ergosta type compounds (6–10), were isolated from solid fermentation products of Stereum hirsutum FP-91666. Two new structures were elucidated by extensive spectroscopic methods, including 1D NMR and 2D NMR, and HR-EI-MS experiments.     

New monoterpenes from Mentha microphylla

Four new monoterpenes, (1 R*,2 S*)-1,2-dihydroxy- p-menth-4(8)-en-3-one ( 1), (4 S*)-4-hydroxy- p-mentha-1,8-dien-3-one ( 2), (4 S*)-4-methoxy- p-mentha-1,8-dien-3-one ( 3), and (3 R*,4 R*,6 S*)-3-acetoxy-6-hydroxy- p-mentha-1,8-diene ( 4) together with four known compounds have been isolated from the aerial parts of Mentha microphylla. The structures were determined using spectroscopic methods particularly high resolution (1)H-, (13)C-NMR as well as 2D (1)H- (1)H COSY, HMQC and HMBC analysis.     

New sesquiterpenes from the roots of Ligularia dentata

Phytochemical investigation of the roots of Ligularia dentata has resulted in the isolation of three new bisabolane sesquiterpenes: 1alpha,3beta,10,11 -tetrahydroxy-2alpha,5alpha,8-triangeloyl-oxybisabola-(7)14-en-4-one, 1alpha,3beta,10-trihydroxy-11 -methoxy-2alpha,5alpha,8-triangeloyloxybisabola-7(14)-en-4-one, and lalpha, 3beta,10-trihydroxy-2alpha,5alpha,8-triangeloyloxybisabola-7(14),11(12)-dien-4-one. Their structures were elucidated with spectro-scopic methods and 2D-NMR techniques as well as chemical transformations. In addition, three known phenolic norsesquiterpenes, liguhodgsonal, ligujapone, and 2-hydroxy-platyphyllide have also been obtained.     

New oleanene-type triterpene saponins from Pueraria peduncularis

Two new oleanane-type triterpene saponins named pedunsaponins B (2) and C (3) were isolated from the roots of Pueraria peduncularis. Their structures were determined to be 3-O-(6-O-methyl)-beta-glucuronopyranosyl-3beta,15alpha-dihydroxyolean-12-en-16-one (2), and 3-O-beta-glucopyranosyl-(1 --> 3)-beta-glucuronopyranosyl-3beta,15alpha-dihydroxyoleana-12-en-16-one (3), on the basis of spectroscopic evidence.     

Alkyl phloroglucinol derivatives from Syzygium levinei and their differentiation-inducing activity

Eleven compounds have been identified from the whole plants of Syzygium levinei (Myrtaceae) on the basis of spectroscopic analysis and chemical methods. Among these compounds, (Z)-1-(2,6-dihydroxy-4-methoxyphenyl)-oct-5-en-1-one (1), (3 E,7 Z)-1-(2,6-dihydroxy-4-methoxyphenyl)-deca-3,7-dien-1-one (2), and 1-(2-O-beta-D-glucopyranosyl-5,6-dihydroxy-4-methoxyphenyl)-octan-1-one (3) were characterized as new alkyl phloroglucinol derivatives, and 1-(2,6-dihydroxy-4-methoxyphenyl)-hexan-1-one (4) was identified as a new natural product. Compounds 1, 2, and 4 were found to inhibit the proliferation of leukemia K562 and HL-60 cells and also to induce the differentiation of K562 cells as determined by the appearance of matured morphology and the increase in the intracellular hemoglobin level.     

蛇莓的化学成分

目的研究蔷薇科植物蛇莓(Duchesnea indica Focke)的化学成分。方法采用多种色谱技术对蛇莓的化学成分进行分离纯化,经理化数据和光谱数据分析鉴定其结构。结果从蛇莓中分离得到9个化合物,结构鉴定为短叶苏木酚酸(1)、短叶苏木酚酸甲酯(2)、短叶苏木酚(3)、山柰酚-3-O-α-L-鼠李糖基-(1→3)-α-L-鼠李糖基-(1→6)-β-D-半乳糖苷(4)、山柰酚-3-O-α-L-鼠李糖基-(1→6)-β-D-半乳糖苷(5)、乌苏酸(6)、齐墩果酸(7)、β-谷甾醇(8)、(24R)-6β-羟基-24-乙基-胆甾-4-烯-3-酮(9)。结论化合物1、2、4、5、7、9为首次从本属植物中分离得到。     

Two new steroidal saponins from the biotransformation product of the rhizomes of Dioscorea nipponica

Two new steroidal saponins, dioscins E (1) and F (2), along with nine known steroidal saponins, were isolated from the biotransformation product of the rhizomes of Dioscorea nipponica using Aspergillus oryzae. The structures of new compounds were established as 25(R)-spirost-5-en-21β-methyl-3β-ol-3-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranoside (1) and (25R)-spirost-5-en-3β-ol-7-one 3-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranoside (2) by detailed spectroscopic analyses including 1D and 2D NMR spectral data ((1)H-(1)H COSY, HSQC, and HMBC) and MS spectrometry.     

Two new monoterpene glycosides and a new (+)-jasmololone glucoside from Bidens parviflora Willd

Two new monoterpene glycosides named bidensmenthosides A, B and a new (+)-jasmololone glucoside, were isolated from the air-dried whole plant of Bidens parviflora Willd. Their structures were determined as (1S, 3S, 4R)-3-hydroxy-p-menth-6-one 3-O-beta-D-glucopyranoside (1), (3R, 4R)-3-hydroxy-p-menth-1 (2)-en-6-one 3-O-beta-D-glucopyranoside (2) and (4R)-hydroxy-3-methyl-2-(2 Z-pentenyl)-cyclopent-2-enone 4-O-beta-D-glucopyranoside (3) based on spectroscopic analysis and physiochemical properties, respectively. The bidensmenthosides A, B and aglycone of 3 were found to reduce 2, 2-diphenyl-1-picrylhydrazyl (DPPH) radicals.     

A new bisabolane sesquiterpenoid from Euphorbia chrysocoma

The new sesquiterpenoid (6R)-2-chloro-6-[(1S)-1,5-dimethylhex-4-en-1-yl]-3-methylcyclohex-2-en-1-one (1), together with ten known compounds, (6R)-6-[(1S)-1,5-dimethylhex-4-en-1-yl]-3-methylcyclohex-2-en-1-one (2), bauerenol acetate (3), lupenone (4), α-amyrenone (5), β-sitosterol (6), stigmasterol (7), β-amyrin (8), ursolic acid (9), betulinic acid (10), scopolin (11), have been isolated from the roots of Euphorbia chrysocoma Lévl. et Vant. Their structures have been elucidated by spectroscopic data.     

蒺藜果实的化学成分研究

目的研究蒺藜果实中的化学成分。方法利用硅胶柱色谱、凝胶柱色谱、高效液相色谱等手段进行分离,根据理化性质及波谱数据鉴定结构。结果与结论从蒺藜果实的乙酸乙酯萃取液中分离得到7个已知成分,分别鉴定为棕榈酸单甘油酯（1）、琥珀酸（2）、香草酸（3）、3-羟基-豆甾-5-烯-7-酮（4）、4-ketopinoresinol（5）、蒺藜酰胺（6）、N-反式咖啡酰基对羟基苯乙胺（7）。化合物1-5为从该植物中首次分离得到。     

岭南山竹子树皮化学成分研究

目的研究藤黄属植物岭南山竹子树皮中的化学成分。方法利用硅胶、Sephadex LH-20等色谱法对山竹子树皮中的化学成分进行分离以及根据所获单体化合物的理化性质和光谱数据（紫外、核磁共振、质谱）鉴定其结构。结果从山竹子树皮中分离得到7个单体化合物,经鉴定分别为10-hydroxybotryococcene（1）、peplusol（2）、stigmast-4-en-3-one（3）、parvifiol（4）、1,2-benzenedicarboxylic acid bis（2-methyl heptyl）ester（5）、camboginol（6）、pedunxanthone C（7）。结论化合物1～7均为首次从该种植物中分离得到。