Triterpenoid saponins from Bongardia chrysogonum

Two new triterpenoid saponins, 3-O-[beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->4)-alph a-L-arabinopyranosyl]-hederagenin (1) and 3-O-[beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->4)-alph a-L-arabinopyranosyl]-hederagenin 28-O-[beta-L-glucopyranosyl-(1-->6)-beta-L-glucopyranosyl] ester (2), together with five known saponins, were isolated from an ethanolic extract of the tubers of Bongardia chrysogonum. The structures of 1 and 2 were determined on the basis of spectroscopic studies.     

Triterpenoid saponins from Symplocos lancifolia

Three new bidesmosidic saponins (1-3) and a new ursane triterpenoid, 2α,3β,11α,23-tetrahydroxyurs-12-en-28-oic acid (4), along with seven known compounds, were isolated from a methanolic extract of the leaves of Symplocos lancifolia. The bidesmosidic saponins were found to possess the same sugar unit part, composed of two β-d-glucose moieties and one α-l-rhamnose moiety, linked to maslinic acid, arjunolic acid, and asiatic acid, respectively. Their structures were elucidated by interpretation of their 1D and 2D NMR spectra and completed by analysis of the HRESIMS data. The antibacterial activity of the isolated triterpenoids was evaluated against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Pseudomonas aeruginosa, and several showed activity against Gram-positive bacteria.     

Triterpenoid saponins from Patrinia scabra简

AIM： To study the chemical constituents and bioactivity of the roots ofPatrinia scabra Bunge. METHODS： The chemical constituents were isolated using various chromatographic methods, and the structures were elucidated on the basis of spectral analysis and chemical methods. In addition, cytotoxic activities toward HepG2 cells were tested by the MTT method. RESULTS： A new triterpenoid saponin, 3-O-（4＇-isovaleryl）-O-β-D-xylose-12,30-dihydroxy-oleanane-28,13-1actone-22-O- β-D-glucoside （1）, along with two known triterpenoid saponins, acanthopanax saponin CP3 （2） and foetoside C （3）, were isolated. CONCLUSION： The aglycone of compound 1 was a new skeleton derivative of oleanolic acid. Compound 2 showed strong cyto- toxicity to HePG2 cells （IC50 1.49 umol.L-1）.     

Triterpenoid saponins from Campsiandra guayanensis

Thirteen new triterpenoid saponins (1-13) were isolated from the aerial parts of Campsiandra guayanensis. Their structures were elucidated by 1D and 2D NMR experiments including 1D-TOCSY, DQF-COSY, ROESY, HSQC, and HMBC spectroscopy, as well as ESIMS analysis. The aglycon moieties of 1-10 were assigned as oleanane derivatives and those of 11-13 as lupane derivatives.     

Triterpenoid saponins from Isertia pittieri.

Two new 27-nor-triterpenoid saponins, pyrocincholic acid 3 beta-O-beta-D-quinovopyranosyl-28-[beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranosyl] ester (1) and pyrocincholic acid 3 beta-O-beta-D-quinovopyranosyl(1-->6)-beta-D-glucopyranosyl-28-[beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl] ester (2) were isolated from the stem bark of Isertia pittieri, together with two known bidesmosidic quinovic acid glycosides. The structures of 1 and 2 were determined on the basis of spectroscopic studies.     

Triterpenoid saponins from Ilex kudincha.

Ten new triterpene saponins, ilekudinosides A-J (2, 6-8, 10, 13-17), together with seven known triterpene saponins, ilexoside XLVIII (1); cynarasaponin C (5); latifolosides A (9), C (3), G (12), and H (4); and kudinoside G (11), were isolated from an aqueous extract of the leaves of Ilex kudincha. They possessed oleanane- and ursane-type triterpenoids as the aglycons. The structures were elucidated by 1D and 2D NMR experiments, including ROE difference, HOHAHA difference, 1H-1H COSY, and 1H-13C COSY (HMQC, HMBC) methods and sugar analysis. Compounds 1 and 5 exhibited acyl CoA cholesteryl acyl transferase (ACAT) inhibitory activity.     

牛膝中的三萜皂苷类成分(英文)

目的:对牛膝(Achyranthese bidentata Bl.)根中的化学成分进行研究。方法:采用D101大孔树脂柱、硅胶柱、反相中压柱、凝胶柱和制备液相进行化学分离和纯化, 并利用各种波谱技术进行结构鉴定。结果:从牛膝中分离并鉴定了5个皂苷类化合物, 分别为:牛膝皂苷 C(1)、牛膝皂苷 D(2)、竹节参皂苷Ⅳ(3)、人参皂苷Ro(4)和姜状三七苷 R1(5)。结论:化合物1为首次从自然界中获得,化合物3为首次从苋科植物中分离得到。     

Triterpenoid saponins from the fruits of Caryocar glabrum

Twenty-one new triterpenoid saponins, named caryocarosides (1-21), glycosides of 2beta-hydroxyoleanolic acid, hederagenin, bayogenin, and gypsogenic acid, have been isolated from the fruits of Caryocar glabrum along with nine known triterpenoid saponins (22-30) that are described for the first time from a plant in the Caryocaraceae. Their structures were established by 1D and 2D NMR techniques ((13)C, COSY, TOCSY, HSQC, HMBC, and ROESY experiments), ESIMS, and acid hydrolysis. The isolated compounds could be classified into two series: glucosides (1-8, 22, 27, and 30) derived from the 3-O-monoglucoside and glucuronides (9-21, 23-26, 28, and 29) derived from the 3-O-monoglucuronide. In 22 of the saponins (1-8, 12-22, and 24-26), a galactose moiety was linked to C-3 of a glucuronic acid or a glucose moiety. The galactose was substituted in position 3 by a second galactose unit (6, 7, 20, and 21) or by a xylose unit (8). Seven saponins (4, 5, 16-19, and 26) were found to be bidesmosides with one glucose unit linked to C-28 of the aglycon. The hemolytic activity of the major saponins (2, 3, 5, 12-15, 17, 24, and 28) was measured on sheep erythrocytes in order to establish structure-activity relationships based on the type of sugar attached to the aglycon and on the structure of this aglycon.     

Triterpenoid saponins from the fruits of Caryocar villosum

Fourteen new triterpenoid saponins (1-14) were isolated from the methanol extract of the fruits of Caryocar villosum along with 10 known saponins. Their structures were established on the basis of extensive NMR (1H, 13C, COSY, TOCSY, ROESY, HSQC, and HMBC) and ESIMS studies. The toxicity of the methanolic extracts of the peel and the pulp of fruits and the crude saponin fraction of the peel was assessed using the Artemia salina test. The antimicrobial activities of caryocarosides IV-21 (14), II-1 (16), III-1 (17), and IV-9 (20) and of saponin 23 were also studied in vitro on Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Mycobacterium smegmatis, and Enterococcus faecalis bacteria.     

Triterpenoid saponins from the fruits of Ternstroemia japonica

Three new triterpenoidal monodesmosides (1-3) and three new triterpenoidal bisdesmosides (4-6), together with two known saponins (7 and 8), were isolated from the fresh fruits of Ternstroemia japonica. The structures of 1-6 (ternstroemiasides A-F) were elucidated on the basis of spectral analysis and chemical degradation.     

Biologically active triterpenoid saponins from Acanthopanax senticosus

Three new triterpenoid saponins, acanthopanaxosides A (1), B (7), and C (13), were isolated from the leaves of Acanthopanax senticosus, together with 12 known saponins. The structures of these new saponins were established as 3-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-30-nor-olean-12,20(29)-dien-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-6-O-acetyl-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (1), 3-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-6-O-acetyl-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (7), and 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-3beta-hydroxyolean-12-ene-28,29-dioic acid (13), on the basis of spectroscopic analysis and chemical degradation. Among the known compounds, sessiloside and tauroside H1 are reported for the first time from A. senticosus. The biological activity of compounds 1-15 was examined against pancreatic lipase. Ciwujianoside C1 (6), tauroside H1 (11), 3-O-alpha-rhamnopyranosyl-(1-->2)-alpha-arabinopyranosyl mesembryanthemoidigenic acid (12), acanthopanaxoside C (13), sessiloside (14), and chiisanoside (15) inhibited pancreatic lipase activity in vitro. In turn, ciwujianosides C2 (3), D2 (5), C4 (8), and C3 (10) and hederasaponin B (9) enhanced this enzyme.     

Triterpenoid saponins from the roots of Pulsatilla koreana

Six new saponins, five lupanes (1-5) and one oleanane (6), along with 11 known saponins, were isolated from the roots of Pulsatilla koreana. The structures of the new saponins were found to be 23-hydroxy-3beta-[(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (1), 23-hydroxy-3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (2), 3beta-[(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (3), 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (4), 23-hydroxy-3beta-[(O-beta-D-glucopyranosyl-(1-->4)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (5), and hederagenin 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside (6). Their structures were determined on the basis of 1D and 2D NMR ((13)C NMR, (1)H NMR, (1)H-(1)H COSY, HMQC, and HMBC) methods, FABMS, and hydrolysis. All isolated compounds were evaluated for their cytotoxic activity against A-549 human lung carcinoma cells.     

太白银莲花地上部分三萜皂苷类化学成分的研究

目的 研究太白银莲花Anemone taipaiensis地上部分化学成分,并初步评估其肿瘤细胞增殖抑制活性。方法 采用正相硅胶、Sephadex LH-20凝胶、ODS反相柱色谱以及半制备高效液相色谱等手段进行分离纯化;根据波谱数据(1D-NMR、2D-NMR及MS)和理化性质鉴定化合物结构;采用MTT法评估化合物对2种人源肿瘤细胞(人急性早幼粒白血病HL-60细胞和人肝癌HepG2细胞)的增殖抑制活性。结果 从太白银莲花地上部分70%乙醇提取物的正丁醇萃取部位分离得到7个齐墩果烷型三萜皂苷类化合物,分别鉴定为常春藤皂苷元-3β-O-β-D-吡喃葡萄糖-(1→3)-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖(1→4)-β-D-吡喃葡萄糖苷(1)、3β-O-β-D-吡喃木糖-(1→3)-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖-齐墩果酸-28-O-β-D-吡喃葡萄糖酯苷(2)、cernusoide C(3)、medicago-saponin P1(4)、常春藤皂苷元-3β-O-β-D-吡喃木糖-(1→3)-α-L-吡喃鼠李糖-(1→2)-[β-D-吡喃葡萄糖-(1...     

虎舌红根茎三萜皂苷类成分的研究

目的研究虎舌红Ardisia mamillata Hance根茎三萜皂苷类成分。方法虎舌红根茎80%乙醇提取物采用硅胶柱、Sephadex LH-20、重结晶等进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。结果从中分离得到7个化合物,分别鉴定为cyclaminorin(1)、ardisicrispin B(2)、3β-O-{α-L-吡喃鼠李糖基-(1→3)-β-D-吡喃葡萄糖基-(1→4)-α-L-吡喃阿拉伯糖基}-16-酮-西克拉敏A(3)、3β-O-{α-L-吡喃鼠李糖基-(1→3)-[β-D-吡喃木糖基-(1→2)]-β-D-吡喃葡萄糖基-(1→4)-α-L-吡喃阿拉伯糖基}-16-酮-西克拉敏A(4)、3β-O-{α-L-吡喃鼠李糖基-(1→3)-β-D-吡喃木糖糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-α-L-吡喃阿拉伯糖基}-16α, 28-二羟基-12-烯-30-齐墩果酸(5)、3β-O-{α-L-吡喃鼠李糖基(1→3)-[β-D-吡喃木糖基-(1→2)]-β-D-吡喃葡萄糖基-(1→4)-[β-D-吡喃葡萄糖基-(1→2]-α-L-吡喃阿拉伯糖基}-16α-羟基-13β, 28-环氧-齐墩果烷(6)、3β-O-{α-L-吡喃鼠李糖基(1→3)-[β-D-吡喃木糖基-(1→2)]-β-D-吡喃葡萄糖基-(1→4)-[β-D-吡喃葡萄糖基-(1→2)]-α-L-吡喃阿拉伯糖基}-16α-羟基-30-乙酰氧基-13, 28-环氧-齐墩果烷(7)。结论化合物4～7为首次从该植物中分离得到,化合物5为首次从该属植物中分离得到。     

江苏细柱五加果实指纹图谱研究△

目的:研究建立江苏细柱五加果实中三萜皂苷类成分HPLC-ELSD指纹图谱分析方法,为其质量控制和药材鉴别提供依据。方法:采用HPLC-ELSD色谱法,使用AlltimaTM-C18色谱柱(250mm×4.6mm,5μm),流动相为乙腈-甲醇-0.5%醋酸水,梯度洗脱,流速为1.0mL·min-1,柱温为35℃。ELSD检测器条件:漂移管温度106℃,载气为氮气,流速为2.9L·min-1,进样20μL。结果:在选定的色谱条件下确定14个共有峰,各批次药材均具有上述特征,但特征峰的相对含量分布差异导致色谱概貌存在一定差异。确定了细柱五加果实中2个三萜皂苷类成分,相对保留时间31min为chikusetsusaponinⅣa峰(10号),相对保留时间50min为3β-[(O-β-D-glucopyranu-ronosyl]oxy)-olean-12-ene-28-olcacid峰(14号),不同批次的10批细柱五加果实中HPLC-ELSD指纹图谱特征峰分离度好,谱峰匹配一致。结论:该方法准确、简单、稳定,其色谱指纹图谱可用于江苏细柱五加果实的鉴别和质量控制。     

无梗五加叶化学成分的研究

 目的:研究无梗五加叶的化学成分。方法:利用各种色谱技米进行分离纯化，根据理化常数和光语数据等进行结构鉴定。结果:从无梗五加叶中分得两种化合物，其结构分别鉴定为:I，(1R)-1,11α-二经基-3,4-开环-羽扇豆-4(23),20(29)-二烯-3, 28一二酸3,11-内酯28-氧-α-L- 吡喃鼠李糖基(1→　4)-β-D-吡喃蔺萄糖基((1→6)-β-D-吡喃葡 萄糖苷；Ⅱ，β-谷甾醇。结论:化合物I系首次从该植物中分出，并且为主要成分。     

刺五加叶化学成分及药理作用研究

目的将刺五加叶的国内外研究进展概况进行整理总结,为刺五加叶的开发利用提供参考。方法查阅近30年相关文献,对刺五加叶所含化学成分、药理作用以及现代临床应用等内容进行归纳整理。结果刺五加叶中主要含有皂苷类、黄酮类以及有机酸类等化合物,有调控心脑血管系统,抑制癌细胞增殖,降低尿糖、血糖,抗炎、抗菌、抗应激、增强免疫力、抗疲劳等药理作用。结论刺五加叶具有保护心脑血管系统、抗肿瘤、降血糖等药理作用。刺五加注射液、刺五加片(胶囊)广泛应用于临床医疗,保健食品五加参茶能够明显改善神经衰弱、失眠等症。     

藏柴胡中三萜皂苷类成分的研究

该研究主要探究藏柴胡中的三萜皂苷类成分。采用大孔吸附树脂,MCI,硅胶,ODS,MDS柱色谱以及半制备高效液相色谱等分离纯化方法,从藏柴胡70%乙醇(含0.5%氨水)提取物中得到12个化合物。利用高分辨质谱、核磁共振等波谱手段鉴定其结构分别为柴胡皂苷b2(1),柴胡皂苷a(2),柴胡皂苷b1(3),柴胡皂苷d(4),hydroxysaikosaponin a(5),柴胡皂苷b3(6),柴胡皂苷c(7),柴胡皂苷i(8),柴胡皂苷f(9),chikusaikosidesⅡ(10),柴胡皂苷s(11),柴胡皂苷I(12)。12个化合物均属齐墩果烷型三萜皂苷类化合物,其中化合物1,3,5,8~9,11~12均为首次从该植物中分离得到。体外抗流感病毒实验表明在20μmol·L-1下,化合物2,4,6,8,11~12对流感病毒WSN33具有较明显抑制作用,其抑制率分别为91.3%,88.6%,53.4%,61.3%,77.3%,57.4%。     

刺五加叶皂苷对实验性脑缺血大鼠的保护作用

目的观察刺五加叶皂苷(ASLS)对大鼠实验性脑缺血的保护作用。方法采用大鼠结扎双侧颈总动脉伴低血压模型,探讨ASLS对实验性脑缺血大鼠脑含水量、脑组织病理、超氧化物歧化酶(SOD)、丙二醛(MDA)、钙离子(Ca2 )及乳酸(LA)的影响。结果ASLS能明显降低实验性脑缺血大鼠的脑含水量、改善脑组织病理变化,提高脑组织SOD活性,降低MDA、Ca2 、LA水平。结论ASLS对大鼠实验性脑缺血具有明显保护作用,可能与其抑制脂质过氧化物损害、提高抗氧化酶活性及降低LA酸中毒和细胞内钙超载有关。     

Triterpene saponins from the leaves of Ilex kudingcha

Nine new triterpene saponins, ilekudinosides K-S (1-9), and eight known triterpene saponins were isolated from the 70% ethanol extract of the leaves of Ilex kudingcha. The new saponins were characterized as 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-alpha-kudinlactone (1), 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranosyl-beta-kudinlactone (2), 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl-gamma-kudinlactone (3), 3-O-beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl-alpha-kudinlactone (4), 3-O-beta-D-glucopyranosyl(1-->2)-alpha-L-arabinopyranosyl-alpha-kudinlactone (5), 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranosyl-alpha-kudinlactone (6), 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-beta-kudinlactone (7), 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl-beta-kudinlactone (8), and 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-gamma-kudinlactone (9), respectively. The structures and stereochemistry of compounds 1-9 were elucidated by spectroscopic data interpretation and chemical degradation.