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题名: 五种植物化学成分的研究
作者: 周凌云
学位类别: 硕士
答辩日期: 2004
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: 陈昌祥
关键词: 化学研究 ; 来江藤 ; 薄片变豆菜 ; 红景天 ; 佛手根 ; 高原香蕾
学位专业: 植物学
中文摘要: 本文共有五章组成。第一章论述了来江藤的化学成分,并建立了新的质量标准。第二章论述了薄片变豆菜的化学成分,并对部分化合物进行了药理筛选。第三章研究了丽江产红景天的化学成分,并对其不同工艺粗提物中活性成分红景天苷进行了测定,为优化工艺提供了依据。第四章初步研究了藏药佛手根和高原香薷的化学结构。论文第五章列出了1998-2003年发表的175个木脂素新化合物的结构式,并对具有生物活性的化合物进行了说明。本论文对五种植物(来江藤、薄片变豆菜、丽江产红景天、佛手、高原香薷的化学成分进行了研究,共分离鉴定51个化合物,其中新化合物4个。已鉴定的化合物类型涉及苯丙素类、芳香族酸酚性化合物、黄酮及黄酮苷类、环烯醚萜苷、单菇苷、三萜皂苷及苷元、甾醇类、脂肪族化合物、碳水化合物九类。最后,我们对部分化合物进行了药理活性筛选。第一章、来江藤的化学成分研究来江藤(Brandisia hancei Hook.f.)位玄参科来江藤属植物,分布于长江以南地区。民间用于治疗风湿和肝炎等。其化学成分和生理活性己有文献报道。其有效成分为苯丙素配糖体成分。根据报道,这类成分具有昆虫拒食作用,抗病毒作用,抗菌作用,降脂作用等生理活性。黄家医圈制药厂以来江藤为原料制成密桶花颗粒新药。该药用于治疗肝炎。其质控标准为地方标准,需要重新建立质量标准。我们被委托分离其中四个主要的化合物actcoside(3),2-acetylactcoside(4),poliumoside(5),2-acetylpolinmoside(6)。同时,我们还分离得到另外七个化合物:3',4'-二羟基苯基-乙基-O-α-L-鼠李吡喃糖基(1→3)β-D-(2-O-乙酰基-4-O-咖啡酰基)半乳吡喃糖苷(2),3',4'-二羟基苯基-乙基-α-L鼠李吡喃糖基(l→3)-β-D-(4-O-咖啡酰基)-半乳吡喃糖苷(l),mussaenoside(7),芦丁(8),芦丁-7-O-β-D-葡萄糖苷(9)和甘露醇(10)。其中,化合物2为新化合物,化合物l为首次从该属植物中分离得到。接着,我们建立了用高效液相色谱法测定蜜桶花颗粒及原植物来江藤中的麦角甾苷含量的方法。该方法快速、简便、准确,所测结果稳定、重现性好,可作为蜜桶花颗粒质量控制的一个检测方法,该方法已被药检部门批准。第二章、薄片变豆菜的化学成分薄片变豆菜(Sanicula lamelligera Hanee)为伞形科变豆菜属植物,是四川省著名的民间药,收载于《四川省中草药标准》试行稿1979年版,具有散寒止咳、行血通经之功效。可用于治疗创伤,胃肠道疾病,粘膜炎,泌尿系统疾病,慢性胸痛。实验证明,该属植物中的皂甙具有抗微生物,溶血栓,抗氧化活性。其植物中具有的轻基肉桂酸衍生物,特别是迷迭香酸,有良好的抗HIV-1和抗氧化活性。国内外对该种植物化学成分未见报道,基于其良好的药用功能,本文对其化学成分进行了的研究,从中共分离得到12个化合物,它们分别是:迷迭香酸(1),迷迭香酸甲酯(2),迷迭香酸4-O-β-吡喃葡萄糖苷(3),咖啡酸(4),4-甲氧基咖啡酸(5),山柰酚-3-O-β-D-吡喃半乳糖苷(6),槲皮素-3-O-β-D-吡喃半乳糖苷(7),山柰酚(8),2,3,4-三甲基苯甲酸(9),3,4-二羟基苯甲酸(10),豆甾醇-3-O-葡萄糖苷(11),3-O-β-D-葡萄糖吡喃糖基(1-2)-[β-D-阿拉伯吡喃糖基(1→3)]-β-D-葡萄糖吡喃糖基-12-齐墩果烷-3β,16αa,21β, 22α,28β-五羟基-21-O-β-D-葡萄吡喃糖苷(12)。其中化合物3和12为新化合物。同时,我们对化合物1,12进行抗肿瘤、抗乙酞胆碱酯酶、抗菌药理筛选,发现化合物l,12并无抗肿瘤细胞K562,K549的活性。化合物l有弱的抗菌活性。第三章、红景天化学成分的研究红景天属的植物具有类似人参和刺五加“适应原样”作用。该属植物主要分布在云南高海拔地区,为中国传统的药用植物。我们研究的丽江产红景天(Rhodiola from Lijiang)由云南红河千山生物制药有限公司提供,该公司在外销生产的提取物时遇到红景天苷含量低的问题。为了了解原料的均一性,工业流程的稳定性,提高产品中红景天营的含量,我们对其提供的原料进行了化学成分的研究。从中共分离得化合物巧个,分别为二十六烷醇(1),乙酸二十六烷醇酯(2),β-谷甾醇(3),胡萝卜甙(4),酪醇(5),红景天甙(6),没食子酸(7),对羟基苯甲酸(s),山柰酚(9),草质素-7-O-(3″-β-D-葡萄糖基)-a-L-鼠李糖甙(10),德钦红景天甙(11),Geranyll-O-α-L-arabinopyranosyl(1→6)-β-D-glucopyranoside(12),2,7-anhydro-β-D-heptulopyranoses(the altroisomer,1s),1,2,3,4,6-五没食子酰基-β-D-吡喃葡萄糖(14),D-甘油糖-D-葡庚糖七醇(15)。利用分离得到的化合物,我们对不同工艺流程所得几批粗提物中主要成分红景天营的含量进行了测定,提出了优化工艺流程的方案。同时,对粗提物色谱图中的8个峰进行了指认,为确定工艺流程中质控标准提供技术资料。第四章、佛手根与高原香蕾化学成分的初探佛手根(Citrus medica var.sarcodactylis(Noot.)Swingle)与高原香薷(Elsholtzia densa var.ianthina(Maxim.ex Kanitz)C.Y.Wu etS.C.Huang)均为藏药配方中的主药。佛手的花、果实中主要含挥发油,主要用于理气、化痰之药用;而其根主要用来治疗男人下消,四肢酸软,即两者在药用上有很大区别。因此,我们对其根进行了化学成分的研究。七个化合物被分离得到,分别为:surcrose(1),α-葡萄糖(2),β-葡萄糖(3),4-羟基苯甲醛(4),4-羟基-3-甲氧基苯甲酸(5),β-谷甾醇苷(6),胡萝卜苷(7)。其水溶性部分经药理活性筛选,并无抗KBSZ-009细胞活性。高原香薷主要分布于青藏高原,用于治疗皮肤病、胃病、梅毒性鼻炎、喉炎及寄生虫病。高原香薷的化学成分尚未见报到。我们分离得到化合物7个,分别为:β-谷甾醇(1),β-谷甾醇棕榈酸酯(2),6-甲基三十三烷(3),山柰酚(4),齐墩果酸(5),二十六烷醇(6),8,R,85-saussurenoside(7)。其中化合物7为新化合物。对此两种植物成分的初探有助我们更好开发藏药。第五章、综述:1998-2003年的木脂素类新化合物本文参考了92篇文献,分类列出了1998-2003年发表的175个木脂素新化合物的结构式,并对具有生物活性的化合物进行了说明。
英文摘要: The dissertation is composed of five chapters. In the first chapter, the author made a chemical research of Brandisia hancei and established a HPLC analysis method. In chapter 2, the chemical constituents of Sanicula lamelligera and the bioactivities of some compounds were studied. In chapter 3, a study on the chemical constituents of Rhodiola from Lijiang was carried out. At the same time, the. content of salidroside was determined. Based on this study, an optimized technics was set up. In chapter 4, an elementary chemical study on two traditional medicines in Zhang nationality. Finally the new lignans from the natural resources of plants from 1998-2003 were reviewed. Fifty-one compounds, including four new compounds were isolated from the above five species. These compounds covered phenylpropanoid glycosides, aromatic compounds, flavanones, flavones, iridoid glycosides, sequerterpenoids glycosides, triterpenoids and their glycosides, steroids, aliphatic compounds, carbohydrate. Finally the bioactivities of some compounds or extract were examined. Chapter 1. Chemical constituents from Brandisia hancei Hook.f. Brandisia hancei Hook.f.(Scrophulariaceae), which is distributed in south china, is used for the treatment of hepatitis and rheumatism. The chemical constituents and bioactivities of this species have been reported. Caffeic acid sugar esters were the active constituents of Brandisia hancei. It was reported that these constituents have shown antibacterial, antifungal, antiviral activities and selective inhibition of 5-lipoxygenase (from the leucotriene biosynthesis). The extract of this plant has been developed Mitonghua Particle by Yunnan Huang Jia Yi Quan company, which can treat rheumatism. But there was no uniform standard on quality control. We were authorized to isolated four major compounds actcoside (3), 2'-acetylactcoside(4), poliumoside(5), 2'-aceylpoliumoside (6). At the same time, other seven compounds, which respectively were β-(3',4'-dihydroxyphenyl)-ethyl-O-α-L-rhamnopyranosyl-(l→3)-β-D-(2-O-acethyl-4-O-caffeoyl)-galactopyranoside (2), 6-(3',4'-dihydroxy-phenyl)-ethyl-O-α-L-rhamnopyranosyl-(l→3)-β-D-(4-O-caffeoyl)-gal actopyranoside (1), mussaenoside (7), luteolin (8), luteolin-7-O-fl-D-glucoside (9) and mannitol (10), also were isolated. Among them, compound 2 was new and compound 1 was isolated from this genus firstly. And then, we established a HPLC analysis method for the determination of acteoside in Mitonghua Particle and Brandisia hancei. This method is rapid, simple, accurate and reproducible, which was proposed to be used for quality control of Mitonghuan Particle and passed. Chapter 2. Chemical constituents from Sanicula lamelligera Hance Sanicula lamelligera belongs to the family Umbelliferae, and is widely used for the treatment of wounds, dermatological, gastrointestina, mild catarrhs of the respiratory system, and urinary system diseases, and chronic chest pains, recorded in the Traditional Chinese Medicine standard of Sichuan province in 1997. It was recently reported that saponins existing this genus are responsible for antimicrobial, hemolytic, and antioxidant activities, whereas hydroxycinnamic derivatives, especially rosmarinic acid ,were responsible for antioxidant activity and acted as active constituent against HIV-1. Up to now, the chemical constituents of this plant have not been reported. To find out the more active compounds, we have studied the chemical constituents of this plant. Twelve compounds were isolated from this plant. They were elucidated to be rosmanic acid (1), rosmanic acid methyl ester (2), rosmanic acid 4-0-β-D-gluctopyranoside (3), 3-(3,4-dihydroxy-phenyl) arylic acid (caffeic acid) (4), 3-(3-Hydroxy-4-methoxyphenyl)arylic acid (5),kaempferol 3-0-β-D-galactopyranoside (6), quercetin 3-0-β-D-gala-ctopyranoside (7), kaempferol (8), 2,3,4-Trimethyl-benzoic acid (9), 3,4-dihydroxy benzoic acid (10), stigmasterol 3-0-β-D-gluctopyranoside (11), 3-0-β-D-glucopyranosyl(l→2)-[β-D-arabinopy-ranosyl(l→3)]-β-D-glucopyranosyl-12-oleanene-3β, 16α, 21β,22α, 28β-pentol-21-O-β-D-glucopyranoside (12). Among them, compound 3 and compound 12 were new. The anti-tumors anti-acetylcholinesterase and anti-epiphyte activities of compound 1, 12 were examined. Compound 1 and 12 showed no anti-tumor activity against K562, K549. Compound 1 showed weak anti-epiphyte activity. Chapter 3. Chemical constituents from Rhodiola from Lijiang In China, plants of the Rhodiola genus have similar effects as Panax ginseng and Acanthopanax senilicosus. As a Chinese medicine plant, it is mainly distributed in the high cold region of Yunnan. The crude extract we have studied was supplied by HongHe QianShan bio-engineering CO. Ltd. Owing to ambiguous content of major constituents, they have difficulty in exporting. Therefore, we have studied the chemical constituents. Fifteen known compounds were isolated and elucidated as 1-hexacosanol (1), cerotyl acetate (2), β-sitosterol (3), daucosterol (4), tyrosol (5),salidroside (6), gallic acid (7), 4-hydroxybenoic acid (8), kae-mpferol (9), rhodiosin (10), rhodionin (11), geranyl 1-O-α-L-arabinopy-ranosyl(l→6)-β-D-glucopyranoside(12),2,7-anhy.dro-β-D-heptulopyran-oses (13), l,2,3,4,6-penta-galloyl-β-D-grucopyranose (14), D-glycero-D-gluco-Heptitol (15). With the isolated salidroside, the content of commercial crude extracts of Rhodiola from Lijiang were determined. At the same time, eight compounds were confirmed in the HPLC chromatrograph of commercial crude extracts of Rhodiola from Lijiang. Chapter 4. Chemical constituents from Citrus medica L. var. sarcodac tylis (Noot.) Swingle and Elsholtzia densa var. ianthina (Maxim ex Kanitz) C.Y. Wu et S.C.Huang Citrus medica is a major part of traditional medicines in Zhang nationality. Its root was used to alleviate aching and limp , while its fruit and flora rich in essential oil can stimulate the circulation of blood and be used as expectorant drug. Owing to great difference in medical value, we have studied its chemical constituents. Seven known constituents were isolated and identified as surcrose (1), oc-glucose (2), β-glucose (3), 4-Hydroxy-benzaldehyde (4), 4-Hydroxy-3-methoxy benzoic acid (5), β-sitosterol (6), daucosterol (7). After bio-activity assay, The water extract showed no effects on anti-KMBZ cell. Elsholtzia densa Var. ianthina is also a traditional medicine in common use in Zhang nationality. It is widely distributed in Qinghai-Tibet plateau, which is used as dermatological agent. Chemical constituents of this species have not been reported previously. Seven compounds in our study were isolated and identified as p-sitosterol (1), |3-sitosterol palmitate (2), 6-Methyl-tritriacontane (3), kaempferol (4), oleanolic acid (5), 1-hexaco sanol (6), 8'R,8S-saussurenoside (7). compound 7 was new. Chapter 6. Review on new lignans compounds in 1998-2003 175 Structure of new lignans compounds are listed according to structure classification. The ones possess bioactivity have been discussed.
语种: 中文
内容类型: 学位论文
URI标识: http://ir.kib.ac.cn/handle/151853/744
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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五种植物化学成分的研究.周凌云[d].中国科学院昆明植物研究所,2004.20-25
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