升麻中新三萜皂苷类成分研究

目的:开发利用升麻Cimicifuga foetida资源,从中寻找新的天然活性成分。方法:利用各种色谱技术进行分离纯化,根据理化性质和各种波谱技术辅以化学方法进行结构鉴定。结果:从升麻根茎80％的乙醇浸膏的EtOAc提取部分中分得4个升麻三萜皂苷类成分,分别鉴定为:7,8-二脱氢-27-脱氧升麻亭(7,8-didehydro-27-de-oxyactein,1),24-氧-乙酰升麻醇-3-O-β-D-木糖苷(23R,24R)[24-O-acetylshengmanol-3-O-β-D-xyl(23R,24R),2],升麻醇(cimigenol,3),升麻醇-3-O-β-D-木糖苷(cimigenol-3-O-β-D-xyl,4)。结论:化合物1为新化合物,2-4为首次从该植物中分得的化合物。体外抗骨质疏松药理活性筛选(以SRB法检测)结果表明,化合物1,2和4在浓度为10-9kg·L^-1时,对大鼠成骨肉瘤细胞株(URM106)有明显的增殖作用。     

黄三七皂苷类化学成分的研究

 目的开发利用黄三七Souliea vaginata资源,从中寻找新的天然活性成分。方法利用各种色谱技术进行分离纯化,根据理化性质和各种波谱技术进行结构鉴定。结果分离鉴定了5个三萜皂苷,分别为升麻醇木糖苷(1)、23-表-26-去氧阿特素(2)、26-去氧阿特素(3)、25-脱水升麻醇木糖苷(4)和升麻醇-3-O-β-D-吡喃木糖(1→3)-β-D-吡喃木糖苷(5)。结论化合物2 ～5均为本属首次分离得到。     

23-O-乙酰升麻醇-3-O-β-D-木糖苷对HepG2细胞的细胞毒性及其作用机制

目的：研究自兴安升麻提取的23-O-乙酰升麻醇-3-O-β-D-木糖苷对HepG2细胞的细胞毒性及其作用机制。方法: 利用MTT法进行细胞毒活性测定；用AO/EB染色法观察细胞个体的凋亡；以流式细胞光度术研究细胞周期的改变并验证凋亡的产生；用蛋白印迹技术从分子水平阐明该化合物的细胞毒作用机制。结果： 23-O-乙酰升麻醇-3-O-β-D-木糖苷可以明显抑制HepG2细胞生长,IC₅₀为16 μmol·L^-1。同时该化合物可以使HepG2细胞产生凋亡形态学变化和G2-M细胞周期阻滞,并使PARP蛋白裂解,bcl-2,Bax,cdc 2和cyclin B 等凋亡和细胞周期相关蛋白表达改变。结论： 23-O-乙酰升麻醇-3-O-β-D-木糖苷对HepG2细胞具有明显的细胞毒作用,该化合物可诱导HepG2细胞凋亡和G₂-M周期阻滞,其凋亡机制涉及caspases家族激活,bcl-2和Bax表达改变,而G₂-M周期阻滞与cdc 2和cyclin B下调直接相关。     

斜方复叶耳蕨的化学成分研究

目的:对斜方复叶耳蕨Arachniodes rhomboidea地上部分进行化学成分分离鉴定。方法:采用不同色谱技术进行分离,用波谱和化学方法确定化合物结构。结果:分离鉴定6个黄酮醇类化合物,分别为山柰酚(1)、山柰素-3-O-α-L-鼠李糖苷(2)、山柰素-3-O-β-D-葡萄糖苷(3)、山柰素-3,7-O-α-L-鼠李糖苷(4)、槲皮素-3-O-β-D-葡萄糖苷(5)、山柰素-3-O-β-D-芸香糖苷(6)。结论:所有化合物均为首次从该植物中得到。     

类叶升麻的化学成分研究

目的：研究我国药用植物类叶升麻Actaea asiatica 根茎的化学成分,为阐明其有效成分提供依据。方法：利用硅胶柱色谱,反相柱色谱,半制备液相进行分离,根据化合物的光谱数据(IR,MS,¹H-NMR,¹³C-NMR)和化学方法鉴定其结构。结果：从根茎的醋酸乙酯萃取物中分离得到6个化合物,分别鉴定为25-O-乙酰升麻醇(1),12β-羟基升麻醇(2),23-epi-26-deoxyactein(3),27-deoxyacetylacteol(4),26-deoxycimicifugenin(5)及β-谷甾醇(6)。结论：以上化合物均为首次从该属植物中分离得到。     

24-O-乙酰升麻醇-3-O-β-D-木糖苷对HepG2细胞的细胞毒性及其作用机制

 目的研究24-O-乙酰升麻醇-3-O-β-D-木糖苷对HepG2细胞的细胞毒性及其作用机制。方法利用MTT法进行细胞毒活性初筛;用荧光染色细胞形态学观察法、流式细胞术和蛋白质杂交技术从细胞和分子水平研究该化合物的细胞毒作用机制。结果24-O-乙酰升麻醇-3-O-β-D-木糖苷可以抑制HepG2细胞生长,IC₅₀值为13μmol·L^-1。该化合物可以诱导HepG2细胞凋亡和G₂/M细胞周期阻滞。进一步分子水平研究表明,该化合物可使PARP蛋白裂解,抗凋亡蛋白bcl2下调,凋亡蛋白Bax上调,细胞周期素cyclinB和细胞周期素依赖性激酶cdc2表达下调。结论24-O-乙酰升麻醇-3-O-β-D-木糖苷通过诱导细胞凋亡和G₂/M细胞周期阻滞来发挥细胞毒作用,其凋亡机制涉及caspases家族激活,bcl2下调和Bax表达上调,而G₂/M周期阻滞与cdc2和cyclinB下调直接相关。     

青蛇藤正丁醇部分苷类成分的分离与鉴定

目的 :研究青蛇藤的化学成分。方法 :应用硅胶 ,SephadexLH-2 0 ,RP-18柱色谱及HPLC进行分离、纯化 ,根据理化常数和光谱分析鉴定结构。结果 :从正丁醇萃取部分分离鉴定了 8个苷类成分 :杠柳苷-(Ⅰ) ,山柰酚- 3-O-α-D 阿拉伯糖苷 (Ⅱ) ,山柰酚 3-O-β-D-葡萄糖苷 (Ⅲ ) ,3′ ,4′ ,5 ,7-tetrahydroxy flavanone 2 (S)- 3′-O-β-D-glucopyra-noside(Ⅳ) ,(+) syringaresinol-4′-O-β-D-monoglucoside(Ⅴ) ,sinapateglucose 1 ester(Ⅵ) ,erigesideC(Ⅶ) ,2,6 dimethoxy 4 hydroxyphenol1-O-β-D-glucoside(Ⅷ )。 结论 :所有化合物均为首次从青蛇藤中分离得到。     

罗布麻花化学成分研究

目的:研究罗布麻花中的化学成分。方法:采用硅胶、Sephadex LH-20及ODS柱色谱分离,用波谱学方法确定结构。结果:从乙醇提取物的醋酸乙酯萃取部分分得7个化合物,其结构鉴定为山柰酚(Ⅰ),槲皮素(Ⅱ),槲皮素-3-O-β-D-葡萄糖苷(Ⅲ),山柰酚-3-O-β-D-葡萄糖苷(Ⅳ),香草酸(Ⅴ),槲皮素-3-O-β-D-吡喃葡萄糖基(2→1)-O-β-D-葡萄吡喃糖苷(Ⅵ),胡萝卜苷(Ⅶ)。结论:化合物Ⅰ,Ⅴ,Ⅵ,Ⅶ均为首次从该植物中分离得到。     

复叶耳蕨地上部分黄酮类化合物

 目的研究复叶耳蕨(Arachniodes exilis)地上部分的化学成分。方法利用硅胶、C₁₈反相硅胶、Sephadex LH-20凝胶等色谱技术对其提取物进行分离纯化,根据化合物的理化性质和光谱数据进行结构鉴定。结果分离得到6个黄酮类化合物,分别为:柚皮芸香苷(1),芒花苷(2),圣草次苷(3),木犀草素-7-O-芸香糖苷(4),5,7-二羟基色原酮-7-O-芸香糖苷(5)和5,7-二羟基色原酮(6)。结论化合物1~6均为首次从该种植物中分离得到。     

细梗胡枝子化学成分研究

目的:研究豆科植物细梗胡枝子Lespedeza virgata的化学成分。方法:将乙醇提取物的醋酸乙酯部分进行反复柱色谱,利用质谱对分离得到的单体进行结构鉴定。结果:分离并鉴定了7个化合物,包括4个黄酮类化合物和3个酚酸类化合物。其中4个黄酮类化合物,分别为槲皮素-3-O-[2″-O-(E-6-O-阿魏酰基)-β-D-葡萄糖]-β-D-半乳糖苷(1),7-O-α-吡喃鼠李糖基山柰酚苷(2),7-O-α-L吡喃鼠李糖基-山柰酚-3-O-β-D-吡喃葡萄糖苷(3),槲皮素(4),3个酚酸类化合物,分别为对羟基反式肉桂酸(5),原儿茶酸(6),对羟基苯甲酸(7)。结论:7个化合物均为首次从该植物中分离获得。     

Cycloartane triterpenoids from Cimicifuga yunnanensis induce apoptosis of breast cancer cells (MCF7) via p53‐dependent mitochondrial signaling pathway

The present study was carried out to investigate the antitumor activity of five cycloartane triterpenoids isolated from Cimicifuga yunnanensis on the breast cancer cell line MCF7 and its corresponding drug resistant subline R‐MCF7, including cimigenol‐3‐O‐β‐d ‐xylopyranoside (compound 1), 25‐O‐acetylcimigenol‐3‐O‐β‐d ‐xylopyranoside (compound 2), 25‐chlorodeoxycimigenol‐3‐O‐β‐d ‐xylopyranoside (compound 3), 25‐O‐acetylcimigenol‐3‐O‐α‐l ‐arabinopyranoside (compound 4) and 23‐O‐acetylcimigenol‐3‐O‐β‐d ‐xylopyranoside (compound 5). The results showed that compounds 2–5 have relatively high antitumor activity on both MCF7 and R‐MCF7 cells. The involvement of apoptosis as a major cause of cycloartane triterpenoids‐induced cell death was further confirmed. The results of RT‐PCR showed that compounds 2–5 increased the expression of p53 and bax, which led to the loss of mitochondrial potential and then resulted in the activation of caspase‐7. These findings collectively demonstrated that compounds 2–5 induced apoptosis of MCF7 via p53‐dependent mitochondrial pathway. Copyright © 2010 John Wiley & Sons, Ltd.     

Cimiracemosides I-P,new 9,19-cyclolanostane triterpene glycosides from Cimicifuga racemosa

Eight new and 13 known triterpene glycosides, along with the known compounds glyceryl-1-palmitate and daucosterol-6'-linoleate were isolated from the roots/rhizomes of Cimicifuga racemosa. The new compounds, designated as cimiracemosides I-P (1, 3-9), were determined by spectral analysis to be 7-dehydro-23-epi-12,26-dideoxyacteol-3-O-beta-D-xylopyranoside (1), 12-O-acetyl-25-anhydrocimigenol-3-O-alpha-L-arabinopyranoside (3), 12-O-acetyl-25-anhydrocimigenol-3-O-beta-D-xylopyranoside (4), 4',23-O-diacetylshengmanol-3-O-beta-D-xylopyranoside (5), 4',23-O-diacetylshengmanol-3-O-alpha-L-arabinopyranoside (6), 23-epi-acetylacteol-3-O-alpha-L-arabinopyranoside (7), 4'-O-acetyl-26-deoxyactein (8), and 16beta:23;24:25-diepoxy-12beta-O-acetyl-3beta-hydroxy-9,19-cyclolanost-23,26-olide-O- beta-D-xylopyranoside (9).     

Steroidal saponins from the rhizomes of Polygonatum sibiricum

Four new steroidal saponins, named neosibiricosides A-D (1-4), were isolated from the rhizomes of Polygonatum sibiricum, along with two known spirostanol glycosides. The structures of the new glycosides were elucidated by spectroscopic methods and acid hydrolysis as (23S,24R,25R)-1-O-acetylspirost-5-ene-1beta,3beta,23,24-tetrol 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)-beta-D-fucopyranoside (1), (25S)-1-O-acetylspirost-5-ene-1beta,3beta-diol 3-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside (2), (25S)-spirost-5-en-3beta-ol 3-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-(1-->4)-2-O-acetyl-beta-D-galactopyranoside (3), and (25R,S)-spirost-5-en-3beta-ol 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside (4). The cytotoxic activity of the isolated compounds was evaluated with human MCF-7 breast cancer cells.     

Cucurbitane-type triterpenoids from the stems of momordica charantia

Four new cucurbitane-type triterpenes, cucurbita-5,23(E)-diene-3beta,7beta,25-triol (1), 3beta-acetoxy-7beta-methoxycucurbita-5,23(E)-dien-25-ol (2), cucurbita-5(10),6,23(E)-triene-3beta,25-diol (5), and cucurbita-5,24-diene-3,7,23-trione (6), together with four known triterpenes, 3beta,25-dihydroxy-7beta-methoxycucurbita-5,23(E)-diene (3), 3beta-hydroxy-7beta,25-dimethoxycucurbita-5,23(E)-diene (4), 3beta,7beta,25-trihydroxycucurbita-5,23(E)-dien-19-al (7), and 25-methoxy-3beta,7beta-dihydroxycucurbita-5,23(E)-dien-19-al (8), were isolated from the methyl alcohol extract of the stems of Momordica charantia. The structures of the new compounds were elucidated by spectroscopic methods.     

New steroidal glycosides from the fruits of Tribulus terrestris

Three new steroidal saponins (1-3) were isolated from the fruits of Tribulus terrestris. Their structures were assigned by spectroscopic methods (IR, HRESIMS, 1D- and 2D-NMR) as 26-O-beta-D-glucopyranosyl-(25S)-5beta-furost-20(22)-en-3bet a, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl- (1-->4)]-beta-D-glucopyranoside (1), 26-O-beta-D-glucopyranosyl-(25S)-5beta-furost-20(22)-en-3bet a, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1 -->4)]-beta-D-galactopyranoside (2), and 25(S)-5beta-spirostan-3beta-ol-3-O-alpha-L-rhamnopyranosyl-( 1-->2)-[b eta-D-glucopyranosyl-(1-->4)]-beta-D-galactopyranoside (3). Compound 3 showed cytotoxicity against a human malignant melanoma cell line (SK-MEL).     

Biotransformation of cycloartane-type triterpenes by the fungus Glomerella fusarioides

Biotransformation of three cycloartane-type triterpenes, cycloartenol (1), 24-methylenecycloartanol (2), and cycloartenone (3), by the fungus Glomerella fusarioides was studied. Compound 1 was converted to 3, cycloart-25-ene-3beta,24-diol (4), and cycloartane-3beta,24,25-triol (5). Compound 2 was metabolized to cycloeucalenol (6) and two new compounds, 24-methylcycloartane-3beta,24,24(1)-triol (7) and 24(1)-methoxy-24-methylcycloartane-3beta,24-diol (8). Compound 3 was converted into two new metabolites, 4alpha,4beta,14alpha-trimethyl-9beta,19-cyclopregnane-3,20-dione (9) and 25-hydroxy-24-methoxycycloartan-3-one (14), and four known compounds, viz., cycloartane-3,24-dione (10), 24-hydroxycycloart-25-en-3-one (11), (23E)-25-hydroxycycloart-23-en-3-one (12), and 24,25-dihydroxycycloartan-3-one (13). The structures of four new metabolites, 7, 8, 9, and 14, were established by spectroscopic methods.     

Cheilanthane sesterterpenes, protein kinase inhibitors, from a marine sponge of the genus Ircinia

Four cheilanthane sesterterpenoids, 25-hydroxy-13(24),15,17-cheilanthatrien-19,25-olide (1), 13,16-epoxy-25-hydroxy-17-cheilanthen-19,25-olide (2), 25-hydroxy-13(24),17-cheilanthadien-16,19-olide (3), and 16,25-dihydroxy-13(24),17-cheilanthadien-19,25-olide (4), were isolated from the marine sponge Irciniasp. Compounds 1, 3, and 4 are new natural products. The four compounds inhibit MSK1 (mitogen and stress activated kinase) and MAPKAPK-2 (mitogen activated protein kinase activated protein kinase), two protein kinases involved in mitogen and stress signal transduction.     

Constituents of the stigmas of Crocus sativus and their tyrosinase inhibitory activity

Four new compounds, crocusatins F (1), G (2), H (3), and I (4a), together with 21 known compounds, were isolated from an aqueous extract of the stigmas of Crocus sativus (saffron). The structures of 1-4 were established by spectral methods. The tyrosinase inhibitory activities of all 25 compounds isolated were evaluated in vitro using mushroom tyrosinase. Among them, crocusatin H (3), crocin-1 (5), and crocin-3 (6) showed significant tyrosinase inhibitory activity.     

Triterpene glycosides from Cimicifuga racemosa

Eight new triterpene glycosides named cimiracemosides A-H, respectively, and eight known triterpene glycosides were isolated from the rhizome extracts of black cohosh (Cimicifuga racemosa). The new compounds were determined by spectral data to be 21-hydroxycimigenol-3-O-alpha-L-arabinopyranoside (1), 21-hydroxycimigenol-3-O-beta-D-xylopyranoside (2), cimigenol-3-O-alpha-L-arabinopyranoside (3), 12beta-acetoxycimigenol-3-O-alpha-L-arabinopyranoside (4), 24-acetylisodahurinol-3-O-beta-D-xylopyranoside (5), 20(S),22(R), 23(S),24(R)-16beta:23;22:25-diepoxy-12beta-acetoxy-3be ta,23, 24-trihydroxy-9,19-cycloanost-7-ene-3-O-beta-D-xylopyranoside (6), 20(S),22(R),23(S),24(R)-16beta:23;22:25-diepoxy-12beta -acetoxy-3beta, 23,24-trihydroxy-9,19-cycloanost-7-en-3-O-alpha-L-arabinopyrano side (7), and 20(S),22(R),23(S), 24(R)-16beta:23;22:25-diepoxy-12beta-acetoxy-3beta,23, 24-trihydroxy-9,19-cycloanostane-3-O-beta-D-xylopyranoside (8).     

海南狗牙花化学成分的研究

目的：对夹竹桃科植物海南狗牙花Ervatamia hainanensis中化学成分进行系统研究。方法：用硅胶柱色谱法和光谱分析法分离和鉴定化学成分。结果：从海南狗牙花中分离到8个化合物：α-amyrin acetate(1),11-oxo-α-amyrin acetate(2),β-谷甾醇(β-sitosteol,3),cycloart-23-ene-3β,25-diol(4),cycloart-25-ene-3β,24-diol(5),5α,8α-epidioxyergosta-6,22-dien-3β-ol(6),ibogamin-3-one(7),β-胡萝卜苷(β-daucosterol,8)。结论：化合物1,2,4～7为首次从该植物中获得。