Two new bioactive triterpene glycosides from the sea cucumber Pseudocolochirus violaceus

By activity-guided fractionation, two new triterpene glycosides, violaceusides A (1) and B (2), were isolated from the sea cucumber Pseudocolochirus violaceus as active compounds causing morphological abnormality of Pyricularia oryzae mycelia. By extensive 2D NMR techniques and chemical evidence, the structures of the two new glycosides were established as 16beta-acetoxy-3-O-[3-O-methyl-beta-D-glucopyranosyl-(1 --> 3)-beta-D-xylopyranosyl-(1 --> 4)-beta-D-quinovopyranosyl-(1 --> 2)-4-O-sodiumsulphate-beta-D-xylopyranosyl]-holosta-7,24-diene-3beta-ol (1) and 16beta-acetoxy-3-O-[3-O-methyl-beta-D-glucopyranosyl-(1 --> 3)-beta-D-xylopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 2)-4-O-sodiumsulphate-beta-D-xylopyranosyl]-holosta-7,24-diene-3beta-ol (2), respectively. The two glycosides also exhibited significant cytotoxicity against HL-60 and BEL-7402 cancer cell lines.     

紫伪翼手参中4个甾醇苷的分离鉴定

目的研究中国南海紫伪黑手参的化学成分。方法应用多种色谱技术分离，运用波谱分析和化学方法鉴定化合物的结构。结果分离得到4个甾醇苷单体并分别鉴定为：24-甲基-5α-胆甾烷-7，22Z-二烯-3β-O-β-吡喃木糖苷（Ⅰ），24-甲基-5α-胆甾烷-7，24（28）-二烯-3β-O-β-D-吡喃木糖苷（Ⅱ），24-甲基-5α-胆甾烷-7-烯-3β-O-β-D-吡喃木糖苷（Ⅲ）和24-乙基-5α-胆甾烷-7-烯-3β-O-D-吡喃木糖苷（Ⅳ）。结论4个化合物均为首次从海参中获得单体。     

Lecanorosides A and B,two new triterpene glycosides from the sea cucumber Actinopyga lecanora

Two new sulphated triterpene glycosides, lecanorosides A (1) and B (2), along with the known compounds holothurins A (3), A₁ (4), and B (5), were isolated from the sea cucumber Actinopyga lecanora. Their structures were deduced from extensive spectral analysis (NMR and MS) and chemical evidence. Glycosides 1 and 4 showed marginal in vitro cytotoxicity against two human tumour cell lines.     

Hillasides A and B, two new cytotoxic triterpene glycosides from the sea cucumber Holothuria hilla Lesson

Two new triterpene glycosides, hillasides A (1) and B (2), were isolated from the sea cucumber H. hilla Lesson, together with one known glycoside holothuria B (3). Their structures were deduced by extensive spectral analysis and chemical evidences. The presence of conjugated double bonds [22E,24-diene] in the aglycone of 1 is a rare structural feature among sea cucumber glycosides. The two glycosides showed significant cytotoxicity against eight human tumour cell lines (A-549, MCF-7, IA9, CAKI-1, PC-3, KB, KB-VIN and HCT-8) with IC₅₀ in the range of 0.1-3.8 μg/ml.     

糙海参中具有抗真菌活性的三萜皂苷(英文)

为了研究糙海参体内的化学成分,寻找结构新颖具有抗真菌活性的三萜皂苷类成分。应用多种色谱分离技术对糙海参体内的化学成分进行分离纯化,根据化合物的理化性质、波谱数据及化学方法鉴定其结构。分离得到3个三萜皂苷化合物,分别为scabraside A (1)、echinoside A (2) 和holothurin A₁ (3),并对其抗真菌活性进行了研究 (1≤MIC₈₀≤16 μg·mL⁻¹)。化合物1为新的三萜皂苷化合物,化合物2和3为首次从该海参中分离得到,它们均显示显著的抗真菌活性。     

可疑翼手参中的一个新三萜皂苷

目的：寻找结构新颖的三萜皂苷类化合物。方法：采用多种色谱方法．对属于枝手目瓜参科的可疑翼手参体内成分进行了分离纯化；并采用多种光谱(IR．UV，ESI-MS，2D-NMR)和化学方法对所分离化合物的结构进行了确定。结果与结论：得到一个新的三萜皂苷类化合物，我们把该化合物命名为coloehiroside A(1)。     

Two new coumarin glycosides from Herpetospermum caudigerum

Phytochemical investigation on the seeds of Herpetospermum caudigerum afforded two new coumarin glycosides A and B (1 and 2), together with a known compound herpetolide A (3). Their structures were determined by spectroscopic methods, including 2D NMR techniques. Compound 3 exhibited cytotoxicity against HepG2 cells with IC₅₀ value of 6.47 μg/ml. Compound 2 showed anti-hepatitis B virus activity with HBsAg secretion by 33.1% at 200 μg/ml.     

Two new secoiridoid glycosides from Verbena officinalis

Two new secoiridoid glycosides, verbenoside A (1) and verbenoside B (2), have been isolated from the ethanol extract of the aerial parts of Verbena officinalis L. Their structures were elucidated on the basis of spectroscopic evidences, especially 1D, 2D NMR, and MS experiments.     

玉足海参中一个新的三萜皂苷脱硫衍生物

目的分离并鉴定玉足海参体内皂苷类化合物的结构。方法将自玉足海参体内提取得到的皂苷leu-cospilotaside A溶于吡啶∶二氧六环(1∶1)的混合液中。120℃加热3h,应用多种色谱技术对回流产物进行分离纯化,根据化合物的理化性质和波谱数据鉴定其结构。结果分离并鉴定了1个三萜皂苷类化合物:3-O-{-βD-吡喃奎诺糖(1(2)-β-D-吡喃木糖}-海参烷-9-烯-22-酮-3β,12α,17α,25α-四醇。结论玉足海参中提取的三萜皂苷leucospilotaside A脱硫衍生物为新化合物。     

Two new alkyl glycosides from Clerodendranthus spicatus

Two new alkyl glycosides, 3-O-β-d-apifuranosyl-(1 → 6)-O-β-d-glucopyranosyl-(3S)-oct-1-en-3-ol (1, clerspide A) and 3-O-β-d-apifuranosyl-(1 → 6)-[β-d-xylopyranosyl-(1 → 2)]-O-β-d-glucopyranosyl-(3S)-oct-1-en-3-ol (2, clerspide B), have been isolated from the whole plants of Clerodendranthus spicatus (Labiatae). Their structures were established on the basis of spectroscopic analyses and chemical method.     

Terminoside A,a new triterpene glycoside from the bark of Terminalia arjuna inhibits nitric oxide production in murine macrophages

Terminoside A (1), a new oleanane-type triterpene was isolated from the acetone fraction of the ethanolic extract of stem bark of Terminalia arjuna. The structure was established as olean-1α,3β,22β-triol-12-en-28-oic acid-3β-D-glucopyranoside. On the basis of spectral data and chemical reactions, terminoside A, potently inhibited nitric oxide (NO) production and decreased inducible nitric oxide synthase (iNOS) levels in lipopolysaccharide-stimulated macrophages.     

Two new dimeric secoiridoid glycosides from the fruits of Ligustrum lucidum

Two new secoiridoid glycosides, ligusides A and B (1 and 2), as well as seven known compounds (3–9), were isolated from the fruits of Ligustrum lucidum. Their structures were elucidated on the basis of spectroscopic and chemical analysis.     

Two new sesquiterpene lactone glycosides from Artemisia frigida Willd.

The investigation of EtOAc-soluble fraction from the aerial parts of Artemisia frigida has led to the isolation of two new sesquiterpene lactone glycosides, named as artemofriginoside A and artemofriginoside B. Their structures were characterized as 3β-(β-d-glucopyranosyloxy)-8β-(p-hydroxyphenylacetyloxy)-4(15),10(14),11(13)-guaiatrien-1α,5β,6β,7αH-12,6-olide (1) and β-(β-d-glucopyranosyloxy)-8β-(2-hydroxy-3-methylbutanoyloxy)-4(15),10(14),11(13)-guaiatrien-1α,5β,6β,7αH-12,6-olide (2), on the basis of 1D and 2D NMR spectral analysis.     

糙海参中具有细胞毒活性的三萜皂苷

目的 研究糙海参（Holothuria scabra Jaeger）具有生物活性的三萜皂苷类。方法 应用大孔树脂柱色谱、正相硅胶柱色谱、反相硅胶柱色谱和HPLC对糙海参体内三萜皂苷活性成分进行分离纯化,根据化合物的理化性质和波谱数据鉴定其结构。结果 分离并鉴定了5个三萜皂苷类化合物,分别为：scabraside C (1)、holothurin A1 (2)、echinoside A (3)、24-dehydroechioside A (4) 和 holothurin A (5), 化合物1-5对人白血病细胞HL-60,MOLT-4和人肺癌细胞的抑制率较强。结论 化合物1-5为首次从糙海参中分离得到,其中化合物1为新化合物。5个化合物均显示显著的体外细胞毒活性。     

Two new triterpene saponins from Lysimachia capillipes

Two new saponins, capilliposide G (1) and capilliposide H (2), were isolated from the whole plants of Lysimachia capillipes. Their structures were determined by 1D and 2D NMR, MS technique and chemical methods.     

Two new triterpene saponins from Lysimachia capillipes

Two new saponins, capilliposide G (1) and capilliposide H (2), were isolated from the whole plants of Lysimachia capillipes. Their structures were determined by 1D and 2D NMR, MS technique and chemical methods.     

Two new glycosides from Carduus acanthoides

Two new glycosides, syringic acid-4-O-β-l-arabinopyranoside (1) and kaempferol-3-O-α-l-rhamnopyranosyl-7-O-β-d-glucuronopyranoside (2), were isolated from whole plants of Carduus acanthoides (Asteraceae), and their structures were elucidated on the basis of spectroscopic analysis.     

Two new triterpene saponins from Lysimachia davurica

Two new saponins, named davuricoside L (1) and davuricoside O (2), have been isolated from the whole plants of Lysimachia davurica. Their structures were determined by 1D and 2D NMR, FAB-MS techniques, and chemical methods.     

Two new triterpene saponins from Lysimachia davurica

Two new saponins, named davuricoside L (1) and davuricoside O (2), have been isolated from the whole plants of Lysimachia davurica. Their structures were determined by 1D and 2D NMR, FAB-MS techniques, and chemical methods.     

Nobilisides A - C, three new triterpene glycosides from the sea cucumber Holothuria nobilis

Three new triterpene glycosides, named nobilisides A ( 1), B ( 2) and C ( 3), were isolated from the sea cucumber Holothuria nobilis Selenka. Their structures were deduced by extensive spectral analysis and chemical evidence. Compounds 1 and 3 are non-sulfated monoglycosides while 2 is a sulfated diglycoside. The presence of two conjugated double bonds [22 E,24-diene and 7,9(11)-diene] in the aglycone of 1 is a rare structural feature among sea cucumber glycosides, while 2 and 3 possess the same 22,25-epoxy moiety as their side chains. All three glycosides exhibited significant cytotoxicity against human tumor cell lines.