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题名: 三种石竹科植物中的环肽和配糖体
作者: 丁中涛
学位类别: 博士
答辩日期: 1998
授予单位: 中国科学院昆明植物研究所
授予地点: 中国科学院昆明植物研究所
导师: 周俊
关键词: 石竹科 ; 多荚草 ; 二蕊荷莲豆 ; 金铁锁 ; 环肽 ; 三萜皂甙 ; 黄酮甙
学位专业: 植物学
中文摘要: 多荚草(Polycarpon prostralum (Forssk.) Aschers.et Schwein. ex Aschers.),二蕊荷莲豆(Drymaria diandra Bl.)和金铁锁(Psammosilene tunicoides W.C.Wu et C.Y.Wu)为三种不同属的石竹科植物,据文献记载均有一定的药理活性,其中多荚草在民间视为有毒,具有散瘀止痛,祛风活血的功效,用于治疗跌打损伤;二蕊荷莲豆则具有清热解毒,祛风逐湿的功能,民间用于治疗急性肝炎,慢性肾炎,消化不良等症;而金铁锁是云南民间重要的药用植物,具有镇痛,抗炎和抑菌等生理活性,常用于止血止痛,活血祛瘀等为了寻找这三种植物的活性成分,同时作为石竹科环肽系列研究的继续,我们研究了这三种植物的化学成分,从中分离得到四十一个化合物,鉴定了其中的三十六个,包括九个新环肽,九个新三萜甙和三个新奇的黄酮甙。本论文主要报道了这些新化合物的分离和结构鉴定情况。一.多荚草中的环肽和三萜皂甙: 多荚草属是石竹科中的一个小属,只包括十六种植物。有报道从其中两种植物中分离得到了一些三萜皂甙。我们从采集于云南西双版纳的多荚草中分离鉴定了三个新环肽:多荚草环肽A-C(Polycarponins A-C),其中多荚草环肽A是一环九肽,多荚草环肽B和C为环八肽(图1)。从多荚草乙醇提取物的正丁醇部分,分离鉴定了五个新的四糖三萜皂甙(图2,3):多荚草皂甙A-E(Prostratosides A-E)。它们均为柴胡皂甙的类似物。从伞形科柴胡属(Bupleurum)和唇形科风轮菜属(Clinopodium)属植物中分离得到的柴胡皂甙大多是以葡萄糖,岩藻糖和鼠李糖为糖基的三糖或二糖甙。而多荚草皂甙A-E是以葡萄糖,阿拉伯糖,木糖为糖基的四糖甙,并且多荚草皂甙A-C的甙元上还有乙酰基取代。我们还从多荚草乙醇提取物的乙酸乙酯部分分离得到四个新的单糖甙(图4):多荚草皂甙F-I(ProstratosidesF-I)。它们也是柴胡皂甙的类似物。其中多荚草皂甙F-H甙元的16位是羰基,这是较为少见的。将多荚草皂甙D和G及多荚草环肽C送至国家新药筛选中心(上海)作抗炎活性筛选。结果表明多荚草皂甙D对二甲苯所致的小鼠耳壳肿大有轻微的抑制作用,而多荚草皂甙G和多荚草环肽C则未表现出此种作用 二.二蕊荷莲豆中的环肽和黄酮甙: 荷莲豆属植物的化学成分研究并不广泛。我们从采集于云南西双版纳的二蕊荷莲豆中分离鉴定了四个新环肽(图5):二蕊荷莲豆环肽A-D(Drymariains A-D),其中二蕊荷莲豆环肽B(环六肽)具有相对较高的含量(2.l克,0.O11%);二蕊荷莲豆环肽D则是一个新奇的环八肽,它具有双环结构,而且在核磁共振溶剂(氘代吡啶和氘代丙酮)中呈现出组成均等的两种构象异构体。从二蕊荷莲豆乙醇提取物的正丁醇部分,分离鉴定了三个新奇的黄酮甙(图6):二蕊荷莲豆黄酮甙A-C(Drymariatins A-C),其中二蕊荷莲豆黄酮甙A的甙元较一般的黄酮骨架多了一个乙烯基,而且氧甙位置在乙烯基上;二蕊荷莲豆黄酮甙B和C则是双糖甙,其中一个糖以氧甙键相连,另一个糖以碳甙键相连,而且以碳甙键相连的糖分别为不常见的二去氧糖和二去氧羰基糖。将已分离得到的二蕊荷莲豆环肽B,二蕊荷莲豆黄酮甙B以及一个已知的生物碱(荷莲豆碱Cordatanine)送至国家新药筛选中心(上海)作抗肿瘤活性筛选。筛选表明:上述三个化合物对HL60人白血病细胞(四氮唑盐还原法,MTT法)和BEL-7402人肝癌细胞(磺酰罗丹明B蛋白染色法,SRB法)的生长均未表现出抑制作用。对上述三个化合物的抗肝炎活性筛选正在进行之中。三.金铁锁中的环肽: 金铁锁是石竹科单种属植物,是著名的云南白药的组成成分之一。其皂甙的研究已有报道。我们从购于云南白药厂的金铁锁药材中分离得到两个环二肽:环(缬氨酸-丙氨酸),环(丙氨酸-丙氨酸);两个环八肽:金铁锁环肽A和B(Psammosilenins A和B)以及两个环二肽的混合物:环(丙氨酸-亮氨酸),环(丙氨酸一异亮氨酸)。它们的化学结构通过波谱方法得以确定(图7)。其中两个环八肽为新化合物,而四个环二肽则是新的天然产物(已有合成报道)。四.综述: 总结了从1990年到现在石竹科植物的化学成分研究概况。参考了76篇文献,并列出了l22个新化合物(包括环肽,三萜皂甙和蜕皮甾酮及其甙)的化学结构。
英文摘要: Plants belonging to the Caryophyllaceae are widely distributed in all of the world, especially in the area of the Mediterranean and the Far East. In China, about 62 species (17 genera) of this family have been used as traditional medicines. In order to search for biologically active compounds, and as a series of investigation on Caryophyllaceae cyclic peptides, the chemical studies on three plants belonging to Caryophyllaceae were carried out, and 41 compounds were obtained. The structures of 36 compounds were determined, incoluding nine new cyclopeptides, nine new triterpenoid saponins and three novel flavonoid glycosides. This thesis is concerned with the isolation and the structure elucidation of these new compounds. 1. Cyclic Peptides and Triterpenoid Saponins from Polycarpon prostratum Three new cyclic peptides(named polycarponins A-C) and nine new triterpenoid saponins(named prostratosides A-I) were isolated from the whole plants of polycarpon prostratum (Forssk.) Aschers. et Schwein. ex Aschers. which is said to be toxic and exhibits anti-inflammatory and anodynic activities. Their structures were determined by detailed spectroscopic analysis (including 2D- NMR) as cyclo(-Pro_1-Gly-Phe_1-Phe_2-Ala_1-Ile_1-Ala_2 -Ile_2-Pro_2-), cyclo(-Gly_1-Ile-Val_1-Leu_1-Val_2-Gly_2-Leu_2-Pro-), cyclo(-Pro_1-Thr-Leu_1-Pro_2-Pro_3-Val-Leu_2-Phe-), 3-0-{β-D-xylopyranosyl-(1 → 2)-β-D-glucopyranosyl-(1 → 4)-[β-D-glucopyranosyl-(1 → 2)]-α-L-arabinopyranoside}-22α- acetoxy -saikogenin G, 3-0-{β-D-xylopyranosyl-(1 → 2)- β-D-glucopyranosyl-(1 → 4)-[β-D-glucopyranosyl-(1 → 2)]-α-L-arabinopyranoside}-16α-hydroxy-22α-acetoxy-saikogenin E, 3-0-{β-D-xylopyranosyl-(1 → 2)-β-D- glucopyranosyl-(1 → 4)-[β-D-glucopyranosyl-(1 → 2)]-α-L-arabinopyranoside}-21β- acetoxy-saikogenin G, 3-O-{β-D-xylopyranosyl-(1 → 2)-β- D-glucopyranosyl-(1 → 4)- [β-D-glucopyranosyl-(1 → 2)]-α-L-arabinopyranoside} -saikogenin D, 3-O-{β-D- xylo-pyranosyl-(1 → 2)-β-D-glucopyranosyl-(1 → 4)-[β- D-glucopyranosyl-(1 → 2)]-α- L-arabinopyranoside}- saikogenin G, 3-O-α-L-arabinopyranosyl -22α-hydroxy-16-ketosaikogenin F, 3-O-α-L-arabinopyranosyl -16-ketosaikogenin F, 3-O-α-L- arabinopyranosyl-22α-hydroxy-16-ketosaikogenin E, 3-O-α- L-arabinopyranosyl-16α-hydroxy-22α-acetoxy-saikogenin E. 2. Cyclic Peptides and Flavonoid Glycosides from Drymaria diandra Four new cyclopeptides(named drymariains A-D) and three novel flavonoid glycosides(named drymariatins A-C) were isolated from the whole plants of Drymaria diandra Bl. which is used as a folk drug for treatment of acute hepatitis in China. On the basis of spectroscopic studies, their structures were elucidated as cyclo(-Phe_1-Pro_1-Pro_2-Pro_3-Phe_2-Phe_3 -Val-Ile-Ala-), cyclo(-Pro_1-Phe-Tyr-Pro_2-Gly-Leu-), cyclo(-Pro-Pro-Phe-Phe-Val-Ile-Ala-Phe-Leu-), cyclo(-Tyr_1-Pro_1-Tyr_2-Phe-Val-Asp-Pro_2-Gly-), 6- trans-[2"-O-(α-L-rhamnopyranosyl)]- ethenyl- 5, 7, 4' -trihydroxyl-flavone, 6-C-(β-D-2'"-deoxy-fucopyranosyl) -7-O-(β-D-glucopyranosyl)-5, 4'-dihydroxyl-flavone, 6-C-(β-D-kerriopyranosyl) -7- O-(β-D-glucopyranosyl)-5, 4'- dihydroxyl-flavone. 3. Cyclic Peptides from Psammosilene tunicoides Psammosilene tunicoides W.C. Wu et C. Y. Wu is a famous medical herb in Yunnan Province, China, from which two cyclic octapeptides (Psammosilenins A and B), two cyclic dipeptides and a mixture of other two cyclic dipeptides, were isolated. Their structures were determined as cyclo(-Pro_1-Phe_1-Pro_2-Phe_2-Phe_3-Ala-Pro_3-Leu-), cyclo(-Pro_1-Gly-Phe_1-Val-Pro_2-Phe_2-Thr-Ile-), cyclo(-Ala-Ala-), cyclo (-Val-Ala-), cyclo(-Ala-Leu-) and cyclo(-Ala-Ile-) by NMR and MS analysis respectively. 4. Chemical Studies on the Plants of Caryophyllaceae from 1990 to 1998 (Review) The chemical investigations on the species belonging to Caryophyllaceae were reviewed with 76 references from 1990 to now. It covered 34 species (14 genera), from which 127 new compounds were isolated. And the structures of 122 new compounds,including cyclopeptides,triterpenoid saponins and ecdysteriods, were list in this review.
语种: 中文
内容类型: 学位论文
URI标识: http://ir.kib.ac.cn/handle/151853/486
Appears in Collections:昆明植物所硕博研究生毕业学位论文_学位论文

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