Two New Oleanane Saponins from Anemone flaccida

Two new oleanane saponins, named flaccidoside II and III, were isolated from the rhizome of ANEMONE FLACCIDA Fr. Schmidt. On the basis of spectroscopic analysis and chemical transformation their structures were elucidated as 3- O-[alpha- L-rhamnopyranosyl-(1-->2)-beta- D-xylopyranosyl]-oleanolic acid 28- O-[alpha- L-rhamnopyranosyl-(1-->4)-beta- D-glucopyranosyl-(1-->6)-beta- D-glucopyranoside] and 3- O-[beta- D-glucopyranosyl-(1-->2)-beta- D-xylopyranosyl]-oleanolic acid 28- O-[alpha- L-rhamnopyranosyl-(1-->4)-beta- D-glucopyranosyl-(1-->6)-beta- D-glucopyranoside].     

Triterpenoid saponins from Anemone flaccida induce apoptosis activity in HeLa cells

Five triterpenoid saponins were isolated from Anemone flaccida Fr. Schmidt. Their structures were identified as glycoside St-I4a (1), glycoside St-J (2), anhuienoside E (3), hederasaponin B (4), and flaccidoside II (5). Compounds 1–2 were isolated from Anemone family for the first time, and compounds 3–4 were isolated from this plant for the first time. The inhibitory effects of saponins on proliferation of HeLa cells were studied by MTT assay, the apoptosis-induction activity was observed by cell-cycle analysis and caspase-3 expression assay. The antitumor activities of the saponins were ranked in the following order: 5>3>4>1>2. The data presented here indicated that naturally occurring triterpenoid saponins can be regarded as excellent structures for the potential development of new anticancer agents.     

Triterpenoid saponins from Anemone begoniifolia

A new triterpenoid saponin, begoniifolide D (1), along with eight known ones (2-9) has been isolated from the methanol extracts of Anemone begoniifolia Lévl. et Vant. Their structures have been elucidated by spectroscopic and chemical methods.     

Triterpenoid Saponins from Primula denticulata

Two triterpene glycosides denticin ( 1) and denticulatin ( 2) have been isolated from the whole plant of PRIMULA DENTICULATA Sm. and their structures were established by spectral and chemical studies as 3beta-{ O-beta- D-glucopyranosyl-(1-->4)-[ O-beta- D-xylopyranosyl-(1-->2)]- O-(beta- D-glucopyranosyl-(1-->4)-[ O-beta- D-glucopyranosyl-(1-->2)]-alpha- L-arabinopyranosyloxy}-16alpha-hydroxy-13beta, 28-epoxyolean-30-al and 3beta-{ O-beta- D-glucopyranosyl-(1-->2)- O-beta- D-glucopyranosyl-(1-->4)-[ O-beta- D-xylopyranosyl-(1-->2)]- O-beta- D-glucopyranosyl-(1-->4)-[ O-beta- D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyloxy}-16alpha-hydroxy-13beta,28-epoxyolean-30-al, respectively.     

Triterpenoid Saponins from Caltha palustris

Three triterpenoid saponins, hederagenin-3- O-alpha- L-arabinopyranoside, oleanolic acid-3- O-alpha- L-rhamnopyranosyl-(1-->2)-alpha- L-arabinopyranoside and hederagenin-3- O-alpha- L-rhamnopyranosyl-(1-->2)-alpha- L-arabinopyranoside, have been isolated from CALTHA PALUSTRIS (Ranunculaceae). The structures were determined by spectroscopic analysis of the acetates.     

Triterpenoid saponins from the rhizomes of Anemone flaccida and their inhibitory activities on LPS-induced NO production in macrophage RAW264.7 cells

A new ursane-type triterpenoid saponin, flaccidoside IV (1), and three new oleanane-type triterpenoid saponins, flaccidosides V–VII (2–4), along with 17 known saponins (5–21), were isolated from the rhizomes of Anemone flaccida. The structures of the new triterpenoid saponins were determined based on spectroscopic analyses and chemical methods. All the isolated saponins were tested for their inhibitory activities on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages, and several bisdesmosidic oleanane-type triterpenoid saponins (2, 7, and 10) showed significant inhibitory activities, which indicated they had potential anti-inflammatory activities under their noncytotoxic concentrations in vitro.     

Triterpenoid saponins from the root of Anemone tomentosa

Three new triterpenoid saponins, tomentoside A (1), B (2) and C (3), along with four known saponins (4?C7) were isolated from the root of Anemone tomentosa. The structures of the new compounds were elucidated as 3-O-??-d-ribopyranosyl-(1??3)-??-l-rhamnopyranosyl-(1??2)-[??-d-glucopyranosyl-(1??4)]-??-l-arabinopyranosyl hederagenin 28-O-??-l-rhamnopyranosyl-(1??4)-??-d-glucopyranosyl-(1??6)-??-d-glucopyranoside (1), 3-O-??-d-ribopyranosyl-(1??3)-??-l-rhamnopyranosyl-(1??2)-[??-d-glucopyranosyl-(1??4)]-??-d-xylopyranosyl hederagenin 28-O-??-l-rhamnopyranosyl-(1??4)-??-d-glucopyranosyl-(1??6)-??-d-glucopyranoside (2) and 3-O-??-d-galactopyranosyl-(1??3)-??-l-rhamnopyranosyl-(1??2)-??-d-xylopyranosyl oleanolic acid 28-O-??-l-rhamnopyranosyl-(1??4)-??-d-glucopyranosyl-(1??6)-??-d-glucopyranoside (3) on the basis of chemical and spectral evidence. In the oligosaccharide chains of compound 3, the characteristic d-galactose residue is a rare structural feature and secondly encountered among triterpenoid saponins from Anemone.     

异叶梁王茶中三萜皂苷的研究

从异叶粱王茶树皮的醇提取物中分离得到两种新的三萜皂苷化学物，异叶梁王茶苷Ⅶ［ｌ］和异叶梁王茶苷Ⅷ［２］；以及一种已知化合物梁王茶苷Ⅱ［３］。经光谱和化学分析，分别鉴定为３－Ｏ－β－（２’，４’－Ｏ－二乙酰基）－Ｄ－吡喃木糖－３β－羟齐墩果－１２－烯－２８，２９－双羧酸－２８－Ｏ－［α－Ｌ－吡喃鼠李糖（１－４）－β－Ｄ－吡喃葡萄糖（１－６）－β－Ｄ－吡喃葡萄糖］酯苷［１］；３－Ｏ－β－（３’－Ｏ－乙酰基）－Ｄ－吡喃木糖－３β－羟齐墩果－１２－烯－２８，２９－双羧酸－２８－Ｏ－［α－Ｌ－吡喃鼠李糖（１－４）－β－Ｄ－吡喃葡萄糖（１－６）－β－Ｄ－吡喃葡萄糖］酯苷［２］。     

中药墨旱莲中的三萜皂苷

从中药墨旱莲Eclipta prostrataL．中分离得到5个三萜皂苷,根据理化性质和光谱数据,分别鉴定为eclalbasaponins Ⅱ(1),Ⅰ(2),Ⅲ(3),3-O[β-D-吡喃葡糖(1→2)-β-D-吡喃葡糖]-16R-乙氧基-齐墩果酸-28-O-β-D-吡喃葡糖苷(4)和3-O[β-D-吡喃葡糖(1→2)-β-D-吡喃葡糖]-刺囊酸-28-Oβ-D-吡喃葡糖苷(5)。化合物4和5为新化合物,分别命名为eclalbasaponins XI和eclalbasaponins XII。化合物1和5具有诱导稻瘟霉菌丝变形活性。     

Triterpenoid Saponins from the Leaves of Ilex Kudincha

Abstract

Eight new triterpenoid saponins, kudinosides I-P along with three known saponins were isolated from the leaves of Ilex kudincha. The aglycone moiety of kudinosides I-K was determined as a new triterpene (kudinolic acid), a fore-genin for the lactonic triterpene. The structures of all saponins were established on the basis of spectroscopic and chemical evidence. The biogenesis of the triterpene with lactonic moiety was briefly discussed.     

异叶梁王茶中三萜皂甙的研究

从异叶梁王茶树皮的醇提取物中分离得到两种新的三萜皂苷化学物，异叶梁王茶苷Ⅶ[1]和异叶梁王茶苷Ⅷ[2]；以及一种已知化合物梁王茶苷Ⅱ[3]。经光谱和化学分析，分别鉴定为3－0－β－（2′，4′-O-二乙酰基）－D－吡喃木糖－3β－羟齐墩果－12－烯－28，29双羧酸－28－O－[α－L－吡喃鼠李糖（1－4）－β－D－吡喃葡萄糖（1－6）－β－D－吡喃葡萄糖]酯苷[1]；3－O－β－（3′－O－乙酰基）－D－吡喃木糖－3β－羟齐墩果－12－烯－28，29－双羟酸－28－O－［α－L－吡喃鼠李糖（1－4）－β－D－吡喃葡萄糖（1－6）－β－D－吡喃葡萄糖］酯苷［2］。     

蜈蚣三七有效成分W3对小鼠脾淋巴细胞增殖的影响

目的：研究林荫银莲花根茎蜈蚣三七中所含有效成分W3对小鼠脾淋巴细胞增殖的影响.方法：利用硅胶柱和C18色谱柱分离纯化W3,采用四甲基偶氮唑蓝法分别检测蜈蚣三七总皂苷、W3及其苷元齐墩果酸对小鼠脾淋巴细胞体外增殖反应的影响.结果：W3对正常增殖的淋巴细胞活性无明显影响;剂量≥0.1μmol·L-1时,W3对刀豆蛋白诱导的淋巴细胞增殖活性有显著的抑制作用（P＜0.05）.结论：蜈蚣三七有效成分W3具有较强的抑制淋巴细胞增殖活性.     

Triterpenoid Saponins from the Root Bark of Araliataibaiensis

从太白木（ＡｒａｌｉａｔａｉｂａｉｅｎｓｉｓＺ．Ｚ．ＷａｎｇｅｔＨ．Ｃ．Ｚｈｅｎｇ）根皮中首次分离得到四个三萜皂甙，根据理化性质和光谱数据，分别鉴定为齐墩果酸３Ｏ［βＤ吡喃木糖（１→２）］［βＤ吡喃葡萄糖（１→３）］βＤ吡喃葡萄糖醛酸甙（１），ｔａｒａｓａｐｏｎｉｎⅤ（２），３Ｏ｛［βＤ吡喃木糖（１→２）］［βＤ吡喃葡萄糖（１→３）］βＤ吡喃葡萄糖醛酸乙酯｝齐墩果酸２８ＯβＤ吡喃葡萄糖甙（３）和３Ｏ｛［βＤ吡喃木糖（１→２）］［βＤ吡喃葡萄糖（１→３）］βＤ吡喃葡萄糖醛酸丁酯｝齐墩果酸２８ＯβＤ吡喃葡萄糖甙（４）。１为新天然产物，３和４为新化合物，分别命名为太白木皂甙Ⅵ（ｔａｉｂａｉｅｎｏｓｉｄｅⅥ）、太白木皂甙Ⅶ（ｔａｉｂａｉｅｎｏｓｉｄｅⅦ）和太白木皂甙Ⅷ（ｔａｉｂａｉｅｎｏｓｉｄｅⅧ）。     

太白Song木根皮的三萜皂甙成分研究

从太原song木（Sralia taibaiensis Z.Z.Wang et H.C.Zheng)根皮中首次分离得到四个三萜皂甙，根据理化性质和光谱数据，分别鉴定为齐墩果酸－3－O－[β－D－吡喃木糖1－→2）][β-D-吡喃葡萄糖（1→3)]-β-D-吡喃葡萄糖醛酸甙（1），tarasaponin V(2),3-O-{[β-D-吡喃木糖（1→2）][β-D-吡喃葡萄糖（1→3）]-β-D吡喃葡萄糖醛酸乙酯}－齐墩果酸－28－O－β－D－吡喃葡萄糖甙（3）和3－O－{[β=D 吡喃木糖（1→2)][β－D吡喃葡萄糖（1→）]-β-D吡喃葡萄糖醛酸丁酯}－齐墩果酸28－O－β－D－吡喃葡萄糖甙（4），1为新天然产物，3和4为新化合物，分别命名为太白Song木皂甙VI（taibaienoside VI),太白Song木皂甙Ⅶ（taibaienosideⅦ)和太白Song木皂甙Ⅷ（taibaienosideⅧ)。     

Three New Triterpenoid Saponins from the Seeds of Vaccaria segetalis

Abstract

Three new triterpenoid saponins, named segetoside G (1), H (2) and I (3), have been isolated from the seeds of Vaccaria segetails. On the basis of chemical reaction and spectral data, their structures have been established as: 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L-arabinofuranosyl (1 → 3)]-β-D-(4-O-acetyl)-fucopyranosyl-gypsogenin-3-O-β-D-gal-actopyranosyl-(1 → 2)-β-D-(6-O-butyl ester)-glucuronopyranoside (1), 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L-(5-O-acetyl)-arabinofuranosyl-(1 → 3)]-β-D-(4-O-acetyl)-fucopyranosyl-gypsogenin-3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranoside (2) and 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L-(5-O-acetyl)-arabinofuranosyl-(1 → 3)]-β-D-(4-O-acetyl)-fucopyranosyl-quillaic acid-3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranoside (3).     

Triterpenoid Saponins from Leaves and Stems of Panax Quinquefolium L

In the chemical investigation on the saponin composition of leaves and stems of Panax quinquefolium L., two new minor dammarane saponins, quinquenoside L₁ (1) and L₂ (2) have been isolated. By means of physico-chemical evidences and spectral analysis their structures were established as 3-O-[β-D-glucopyranosyl-(1-2)-β-D-glucopyranosyl]-20-O-β-D-glucopyranosy-dammara-23,25-diene-3β, 12β, 20(S)-triol (1) and 3-O-[β-D-glucopyranosyl-(1-2)-β-D-glucopyranosyl]-20-O-β-D-D-glucopyranosyl-(24Z)-dammar-24-ene-3β, 12β, 20(S), 26-tetraol (2).     

金银花中三萜皂甙的分离与结构确定

金银花中三萜皂甙的分离与结构确定娄红祥，田进国，苑辉卿，季梅，吕木坚，郎伟君（山东医科大学药学系，济南２５００１２）（北京大学化学系仪器分析中心，北京１００８７１）金银花为忍冬科植物忍冬ＬｏｎｉｃｅｒａｊａｐｏｎｉｃａＴｈｕｎｂ．的花蕾，具有抗菌，抗...     

Triterpenoid Saponins from Leaves and Stems of Panax Quinquefolium L

Abstract

In the chemical investigation on the saponin composition of leaves and stems of Panax quinquefolium L., two new minor dammarane saponins, quinquenoside L₁ (1) and L₂ (2) have been isolated. By means of physico-chemical evidences and spectral analysis their structures were established as 3-O-[β-D-glucopyranosyl-(1-2)-β-D-glucopyranosyl]-20-O-β-D-glucopyranosy-dammara-23,25-diene-3β, 12β, 20(S)-triol (1) and 3-O-[β-D-glucopyranosyl-(1-2)-β-D-glucopyranosyl]-20-O-β-D-D-glucopyranosyl-(24Z)-dammar-24-ene-3β, 12β, 20(S), 26-tetraol (2).     

冬青属苦丁茶中的三萜及其皂苷类化合物

OBJECTIVE Triterpenes and triterpenoid saponins in two species of Genus Ilex,namely Ilex latifolia and Ilex kudincha that are widely used as a kind of popular tea "Kudingcha" in China,were introduced.METHODS The recent investigations were reviewed,and the