中国科学院昆明植物研究所机构知识库
Advanced  
KIB OpenIR  > 昆明植物所硕博研究生毕业学位论文  > 学位论文
题名: 四种药用植物抗HIV活性成分研究
作者: 王易芬
学位类别: 博士
答辩日期: 2003
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: 罗士德
中文摘要: 本论文对具有抗HIV活性的四种药用植物:黄花紫茉莉(Mirabilis jalara L.)、滇黄精(Polygonatum kingianum Coll.et Hemsl)、水青树(Tetracentron sinense Oliv.)、多花钩儿茶(B erchemia floribuna Brongn.)的化学成分、活性成分进行了初步研究。通过硅胶、葡聚糖凝胶(LH-20)、反相硅胶(RP-8和RP-18)、MCI CHP-20P、D-101大孔树脂等分离材料和多种分离技术,从四种植物中共分离、鉴定了85个化合物,包括单菇、三萜、甾体、黄酮、香豆素、木质素、生物碱、酚性小分子化合物及其贰类化合物。其中14个新化合物,结构类型涉及鱼藤酮、黄酮贰、四氢蔡酮糖甙、木质素、叫垛生物碱、叫噪里嗦酮及酚性小分子化合物,并对部份化合物进行了初步的抗HIV一IRT活性及抗菌活性研究。第一章为黄花紫茉莉化学成分及抗HIV活性研究。从其根中共分离鉴定了19个化合物,包括二个6a,12a-二氢鱼藤酮(1-2),四个6a,12a-去氢鱼藤酮(3-6),一个异黄酮试(7),两个生物碱(8,17),一个二氢黄酮贰(9),一个甘油酷(10),四个达码烷型三菇试(11-14),两个苯甲醛类化合物(15-16)及两个幽体(28,29),其中1,3,5,7为新化合物,化合物2,4,6,8一17为首次从该种植物中分离得到。在化合物1-5和1卜17中,黄芭贰n(12)和异哇琳生物碱(17)具有抗HIV-1RT的活性。据文献报道,8的相似化合物能抑制HIV一1在淋巴细胞系细胞Hg细胞中的生长复制。第二章为滇黄精化学成分及生物活性研究。从脂溶性部份共分离得到12个化合物,包括两个叫噪里嗦酮(18-19),五个黄酮类化合物(20-24),一个糠醛(25),一个水杨酸(26)及三个幽体(27,28,29),从其正丁醇部份分离得到三个分离得到。研究了部份化合物的抗HIV-1 RT活性,未发现活性化合物。用纸片扩散法对化合物18-23、30进行抗菌活性研究,发现叫噪里嗦酮类化合物(18-19)具有抗真菌和细菌的活性,化合物22具有一定的抗肺炎链球菌的活性,而化合物20和21具有抗金黄色葡萄球菌和结核分枝杆菌的活性。同时,我们还发现化合物18在200μg/ml时对HI琴IRT的抑制率为51.6%。第三章为水青树化学成分及生物活性研究。从其茎干部份共分离鉴定了33个化合物,包括10个苯丙素及其试类化合物(33-42),10个酚性化合物(43-52),两个香豆素(53-54),两个生物碱(55-56),一个黄烷类化合物(57),两个乙酞鼠李糖贰(58-59),6个三萜(60-65),其中化合物33、34、39、40、49、55为六个新化合物,而化合物35-38、41-48、50-55、58-59、61、63为首次从该植物中分离得到。我们发现水青树的脂溶性部份具有抗HIV活性,而从乙酷部份分离得到的化合物62、64、65据文献报道具有抗HIV-1活性。可能这是它的活性成分。第四章为多花钩儿茶的化学成分及生物活性研究。从其茎叶中分离得到20个化合物,包括15个黄酮及其贰类化合物(66-80),两个四氢蔡酮贰(81-82),两个单菇(83一84)及一个果糖贰(85)。其中化合物75、81、82为新化合物,而化合物66-74,76-80,83-85为首次从该植物中分离得到。另据文献报道,化合物68,70,71,73,76-78具有抗HIV活性。最后综述了鱼藤酮类化合物的研究概况。总结了从1961年2002年有关鱼藤酮类化合物的研究结果。参考文献92篇,列出了在此期间发表的180个鱼藤酮化合物。
英文摘要: This thesis elaborated the studies on the Anti-HIV chemical constituents of four medicinal plants, Mirabilis jalapa L, Polygonatum kingianum Coll. et Hemsl., Tetracentron sinense Oliv. and Berchemia floribunda Brongn. Totally 85 compounds were isolated and identified by various chromatographies over silica gel column, Sephadex LH-20, MCI CHP-20P, RP-8 and RP-18 si gel. Those compounds covered monoterenoids, triterpenoids, steroids, flavanones, flavones, coumarins, lignans, alkaloids and aromatic compounds. Among them, 14 were new ones, including three rotenoids, two flavone glycosides, two tetralones, two lignans, one alkaloid, one indolizione and three simple aromatic compounds. On the other hand, we investigated the activities of anti-HIV and antibacteria and antifungi of some compounds. M. jalapa is a plant belonging to the family Nyctaginaceae and widely used as a traditional folk herb to treat acute arthritis, anesthesia, inflammation, and so on. In the course of our preliminary screening on the Chinese folk herbs as anti-HIV agents, it was found that the extract of the roots of Mirabilis jalapa L. showed potent inhibitory activity against HIV in vitro (EC_(50) =1.9μg/mL, IC_(50)>250μg/mL, TI> 211). In order to find out its active constituents, M. jalapa collected at Kunming in Yunnan Province was investigated phytochemically. From its roots, 19 compounds were isolated and identified to be mirabijalone A (6a,12a-dihydro-4,ll,12a-trihydroxy-9-methoxy-8,10-dimethyl [1] benzopyrano [3,4-b] [1]' benzopyran~12(6H)-one, 1), boeravinone C (2), mirabijalone B (3), 9-O-methyl-4-hydroxyboeravinone B (4), mirabijalone D (5), boeravinone F (6), mirabijalone C (7), flazin (l-[5-(hydroxymethyl)-2-furanyl]-9H-pyrido [3.4-b] indole-3-carboxylic acid, 8), 4'-hydroxy-2,3-dihydroflavone 7-p-D-glucopyranoside (9), gingerglycolipid A (10), astragaloside IV (11), astragaloside II (12), astragaloside III (13), astragaloside Ml (14), 3,4-dihydroxybenzaldehyde (15), p-hydroxybenzaldehyde (16), 1,2,3,4- tetrahydro -l-methylisoquinoline-7,8-diol (17), p-sitosterol (28) and daucosterol (29), which the compounds 1, 3, 5, 7 were the new ones and compounds 2, 4, 6, 8-17 were obtained from this plant for the first time. The structures were illustrated in Figure 1. Among them, compounds 12 and 17 showed potential inhibitory activities against HIV-1 reverse transcriptase at 200 ug/mL and it was reported that the derivates of 8 had the activity against HTV. Polygonatum Mngianum Coll. et Hemsl. (Liliaceae) is distributed in southwestern China. Its rhizome, called "Huangjing" and widely used in traditional Chinese medicine, is used as a tonic and a remedy to treat lung diseases, upset stomachs and diabetes. Previous studies on this plant have revealed the presence of saponins, but no bioactive constituents have been found yet and investigation on polar fraction has not been reported. The ethyl acetate portion of the ethanol extract from its rhizomes showed a potent inhibitory activity against HIV in vitro (EC5o=2.22p.g/mL, IC50 > 250ng/mL, TI >775), antibacterial and antifungal activities. From this partition, 12 compounds were isolated and identified to be 3-butyloxymethyl-5,6,7,8-tetrahydro-8-indolizione (18), 3-ethoxymethyl-5,6,7,8-tetrahydro-8-indolizione (19), liquiritigenin (20), isoliquiritigenin (21), 4', 7-dihydroxy-3'-methoxyisoflavone (22), (6aR, llaR)-3, 9-dimethoxy-10-hydroxypterocarpan (23), isomucronulatol (24), 5-hydroxymethyl 2-furancarboxaldehyde (25), 3J5-sitosteroI palmitate (26), salicylic acid (27), P-sitosterol (28) and daucosterol (29). And three compounds were isolated rom the n-butyl alcohol, which were identified to be n-butyl-p-D-fructofuranoside (30), n-butyl-a-D-fructofuranoside (31), n-butyl-p-D-fructopyranoside (32). Among them, compound 18 was a new indolizione and compounds 19-27 were obtained from this plant for the first time. The structures were illustrated in Figure 2. Inhibitory activities of compounds 18-22 against Penicillium avellanewn UC-4376, Staphylococcus aureus, Mycobacterium tuberculosis and Streptococcus pneumonia were determined by paper disk diffusion assay on agar plates. Compounds 18 and 19 showed activities against bacteria and fungi. Their minimal inhibition amount (MIA) were 100, 300, 200, 200 jig/disk and 250, 400, 300, 300 ug/disk, respectively. Compound 22 showed activity against Streptococcus pneumonia and compounds 20 and 21 showed activities against Staphylococcus aureus, Mycobacterium tuberculosis at 500 ug/disk. And compound 18 showed 51.6% inhibition percentage against HIV-1 reverse transcriptase at 200μglxaL. etracentron sinense Oliv. is the only species of the genus Tetracentron (Tetraceneae), Chemical studies on this plant have been rarely reported. Thirty three compounds were isolated from the alcohol extract of the stems. Based on spectroscopic and physic-chemical data, their structures were identified to be 4',5'-methylenedioxyphenylpropanoic acid 2'-P-D-glucopyranoside (tetracentron-sinside A, 33), 4',5'-methylenedioxyphenylpropionic acid methyl ester 2-P-D-glucopyranoside (tetracentronsinside B, 34), trans-syxingm. (35), cw-syringin (36), r/zreo-guaiacylglycerol 8-0-P-D-glucopyranoside (37), erytfiro-l-(4-hydroxy-phenyl)-l,2-propanediol 2-O-p-D-glucopyranoside (38), 4,7,9,5',9'-pentahydroxy-3-methoxy-8-0-4'-neolignan -3'-0-p-D-glucopyranoside (tetracentronsinside C, 39), tetracentronsine A (40), 2,3-trans-3,4~cis-A,5-trans-2,5-b\s. (4-hydroxyphenyl) -3,4-dimethyltetrahydrofuran (41), 2,3-/m"5-3,4-cw-4,5-cw-2,5-bis (4-hydroxy-phenyl)-3,4-dimethyltetrahydrofuran (42), 2-hydroxy-5-(2-hydroxyethyl)phenyl 3-D-glucopyranoside (43), 2,6-dimethoxy-^4-hydroxyphenol 1-0-p-D- lucopyranoside (44), 3,5-dimethoxy-4-hydroxyphenol 1-0-p-D-glucopyranoside 45), 3,4,5-trimethoxyphenol 1-0-p-D-ghicopyranoside (46), syringic acid -D-glucopyranosyl ester (or erigeside, 47), syringic acid 4 - p-D-glucopyranoside 48), 4-(3',4'-methylenedioxy- phenyl)-3-methyl-2-butanone (tetracentronsine B, 49), methoxy hydroquinone-4-P-D-glucopyranoside, or tachioside (50), methoxyhydroquinone -1-P-D-glucoside, isotachioside (51), p-hydroxycinnamic acid (52), 7-p-D-glucopyranosyloxy-6-methoxycoumarin (53), 7-p-D-glucopyranosyloxy-5-hydroxy-6-methoxycoumarin (54), 3-hydroxyethylindole 5-p-D-glucopyranoside (tetracentronsinsides D, 55), N-p-coumaroyltyramine [or N (p-hydroxyphenethyl) p-coumaramide, 56], a-actylrhamnoside (57), p -actylrhamnoside (58), (+)-catechin (59), lupeol (60), betulin (61), betulinic acid (62), monogynol (63), oleanolic acid (64), 2a,3p-dihydroxy-12-oleanen-28-oic acid (or maslinic acid, 65). Compounds 33, 34, 39,40,49,55 were new ones. Their structures were illustrated in Figure 3. We found compounds 33, 46, 54 had no anti-HIV activity, but it was reported that compounds 61, 62, 64, 65 showed the activities against HFV. So they may be the anti-HIV active constituents of this species. Berchemia floribunda Brongn. (Rhamnaceaae) which is widely distributed in China was used as treatment rheumatic arthritis, jaundice and comtusions and strains and dysmenorrhoea. Since no work has been previously done on the chemical constituents of Berchemia floribunda, we have, therefore, examined the stem and leaves of this plant in order to found its active compounds against HIV. So 20 compounds were obtained and elucidated to be eriodictyol (66), aromadendrin (67), trara-dihydroquercetin (68), cw-dihydroquercetin (69), kaempferol (70), quercetin (71), juglanin (=kaempferol-3-CMx-L-arabinofuranoside, 72), quercetin-3-O-a-L- arabinofuranoside or avicularin (73), quercetin 3 '-methyl ether, 3-O-a-L-arabinofuranoside (74), quercetin-3-0-(2-actyl-a-L-arabinofuranoside (75), quercetin-3-O-β-D-glucopyranoside (76), quercetin 3-0-a-rhamnopyranoside (77), quercetin-3-O-P-D-galactopyranoside (78), marsupsin (79), maesopsin 6-O-glucoside (80), 8-hydroxy-a-tetralone 4α-O-(3-D-glucopyranoside (berchemiaside A, 81), 5,8-dihydroxy-a-tetralone 4α-O-
语种: 中文
内容类型: 学位论文
URI标识: http://ir.kib.ac.cn/handle/151853/662
Appears in Collections:昆明植物所硕博研究生毕业学位论文_学位论文

Files in This Item:
File Name/ File Size Content Type Version Access License
LW011537.pdf(1920KB)----限制开放-- 联系获取全文

Recommended Citation:
四种药用植物抗HIV活性成分研究.王易芬[d].中国科学院昆明植物研究所,2003.20-25
Service
Recommend this item
Sava as my favorate item
Show this item's statistics
Export Endnote File
Google Scholar
Similar articles in Google Scholar
[王易芬]'s Articles
CSDL cross search
Similar articles in CSDL Cross Search
[王易芬]‘s Articles
Related Copyright Policies
Null
Social Bookmarking
Add to CiteULike Add to Connotea Add to Del.icio.us Add to Digg Add to Reddit
所有评论 (0)
暂无评论
 
评注功能仅针对注册用户开放,请您登录
您对该条目有什么异议,请填写以下表单,管理员会尽快联系您。
内 容:
Email:  *
单位:
验证码:   刷新
您在IR的使用过程中有什么好的想法或者建议可以反馈给我们。
标 题:
 *
内 容:
Email:  *
验证码:   刷新

Items in IR are protected by copyright, with all rights reserved, unless otherwise indicated.

 

 

Valid XHTML 1.0!
Copyright © 2007-2017  中国科学院昆明植物研究所 - Feedback
Powered by CSpace