野生食用蔬菜甜菜树和黄连木化学成分及抗氧化活性
其他题名Chemical and Antioxidant Constituents from Wild Vegetable Yunnanopilia longistaminea and Pistacia chinensis
柳建军
学位类型硕士
导师刘锡葵
2008-01-28
学位授予单位中国科学院昆明植物研究所
学位授予地点昆明植物研究所
学位专业药物化学
关键词甜菜树 黄连木 化学成分 抗氧化活性
摘要本论文由两章组成。第一章介绍了甜菜树 ([Yunnanopilia longistaminea (W. Z. Li) C. Y. Wu & D. Z. Li]) 的乙醇提取物化学成分的分离和结构鉴定,以及各成分清除DPPH自由基的抗氧化活性;第二章介绍了黄连木 (Pistacia chinensis Bunge.) 乙醇提取物乙酸乙酯萃取物的化学成分的分离和结构鉴定,同时也对分离得到的各化合物的清除DPPH自由基的抗氧化活性进行了报导。 利用各种色谱分离技术 (硅胶 (200-300目)、硅胶H、Sephadex LH-20、RP-18、D101大孔树脂),从上述两种植物中共分离得到了39个化合物,经波谱数据分析 (UV, IR, MS, 1D, 2D-NMR和HRMS) 等手段,鉴定了它们的结构,其中新化合物1个。抗氧化实验结果表明其中7个化合物具有较好的清除DPPH自由基的抗氧化活性。 第一章 甜菜树化学成分及抗氧化活性 甜菜树 ([Yunnanopilia longistaminea (W. Z. Li) C. Y. Wu & D. Z. Li]) 系山柚子科 (Opiliaceae) 多年生木本植物,是我国特有的单种属植物,其幼嫩芽叶是一种鲜美可口的野生蔬菜。至今没有发现关于甜菜树化学成分研究的报导。我们对2004年4月采自云南省石屏县的甜菜树的食用部位的化学成分进行了系统的研究,应用各种色谱分离技术从中分离得到了21个化合物,经波谱数据分析分别鉴定为:13b (S)-hydroxy-17c-ethoxypheaophorbide a (1),邻苯二甲酸二异丁酯 (diisobutyl phthalate, 2),十八酸单甘油酯 (glyceryl monostearate, 3),二十四酸 (tetracosanoic acid, 4),三十烷醇 (1-triacontanol, 5),油酸甲酯 (methyl oleate, 6),亚麻酸甲酯 (methyl linolenate, 7),二十八烷 (octacosane, 8),三十二烷 (dotriacontane, 9),-谷甾醇 (-sitosterol, 10),油酸 (oleic acid, 11),D-甘露醇 (D-mannitol, 12),岩白菜素 (bergenin, 13),邻苯二甲酸二 (2-乙基) 己酯 (bis-(2-ethylhexyl) phthalate, 14),云南红豆杉酯乙 (taxayunnansin B, 15), taxumairol E (16),胡萝卜苷 (daucosterol, 17),2, 5-二氧-4-咪唑烷基-氨基甲酸 ((2, 5-dioxo-4-imidazolidinyl)-carbamic acid, 18), 芦丁 (rutin, 19),酪氨酸 (tyrosine, 20),半乳糖醇 (galactitol, 21)。所有化合物均为首次从该植物中分离得到,化合物15和16的发现拓展了紫衫烷类化合物在植物中的分布,具有潜在的资源应用价值。对所有分得的化合物的抗DPPH自由基氧化活性进行了测定,结果表明除化合物19 (芦丁) 外,其它化合物的抗DPPH自由基氧化活性都较弱。 第二章 黄连木化学成分及抗氧化活性 黄连木 (Pistacia chinensis Bunge.),别名中国黄连木,又称黄楝、楷木、鸡冠木、烂心木、崖楝等,为漆树科 (Anacardiaceae) 黄连木属 (Pistacia) 落叶乔木,是一种极其重要的木本油料植物。其嫩叶、嫩芽和雄花序是上等野生绿色蔬菜,清香、嫩脆,鲜美可口,是一道深受人们喜爱的菜肴。为更好的开发这一野生蔬菜资源,我们对采自云南省元江县的黄连木嫩叶芽及花序等可食用部位的化学成分进行了研究。利用各种色谱分离技术从中分离得到了18个化合物,结合光谱数据和理化常数对照鉴定化合物的结构分别为:亚麻酸乙酯 (ethyl linolenate, 1),-谷甾醇 (-sitosterol, 2),对羟基苯乙酸 (4-hydroxyphenylacetic acid, 3),没食子酸乙酯 (3, 4, 5-trihydroxybenzoic acid ethyl ester, 4),赤杨二醇 (alnusdiol, 5),穗花杉双黄酮 (amentoflavone, 6),对羟基苯甲酸 (4-hydroxybenzoic acid, 7),原儿茶素 (3, 4-dihydroxybenzoic acid, 8),没食子酸 (3, 4, 5-trihydroxybenzoic acid, 9),黄连木酰胺 (pistaciamide, 10*),槲皮素-3-O-β-D-木糖苷 (quercetin-3-O-β-D-xylopyranoside, 11),芦丁 (rutin, 12),胡萝卜苷 (daucosterol, 13),槲皮素-3-O-β-D-葡萄糖苷 (quercetin-3-O-β-D-glucopyranoside, 14),槲皮素 (quercetin, 15),山柰酚-3,7-O-α-L-二鼠李糖苷 (kaempferol-3,7-O-α-L-dirhamnoside, 16),柚皮素 (naringenin, 17),4-羟基肉桂酸 (4-hydroxycinnamic acid, 18),其中化合物10为新化合物,除化合物2, 4, 9, 14和15外,其它化合物均为首次从该植物中分离得到。对所有分离得到的化合物的抗DPPH自由基氧化活性进行了测定,结果表明其中化合物4,8,9,11,12,14和15 具有较好的活性,其活性都强于相同浓度下BHA对照的活性。 关键词:甜菜树,黄连木,化学成分,抗氧化活性
其他摘要This thesis is composed of two chapters. Chapter 1 and 2 focused on the chemical constituents and its scavenging effect on DPPH free radicals of [Yunnanopilia longistaminea (W. Z. Li) C. Y. Wu & D. Z. Li] and Pistacia chinensis Bunge. respectively. 39 compounds, including 1 new compound, were isolated from the above two species, their structures were elucidated based on spectroscopic analyses (UV, IR, MS, 1D, 2D-NMR and HRMS). Antioxidant activities test on the isolated compounds showed that seven compounds presented good scavenging effect on DPPH free radicals. Chapter 1 Chemical and Antioxidant Constituents from Yunnanopilia longistaminea Yunnanopilia longistaminea (W. Z. Li) C. Y. Wu & D. Z. Li, belonging to family Opiliaceae, is a single-species woody perennial plant endemic to China, its tender leaves and shoots can be developed as a tasty and delicious vegetable. We studied chemical constituents of its ethanol extracts systematically for the first time. Plant materials were collected from Shiping County Yunnan Province in April 2004. 21 known compounds were isolated from the edible part of Yunnanopilia longistaminea (W. Z. Li) C. Y. Wu & D. Z. Li. Based on spectral analyses (UV, IR, 1D, 2D NMR and MS) and comparison with reported literatures, the isolated compounds were deduced as follows: 13b (S)-hydroxy-17c-ethoxypheaophorbide a (1), diisobutyl phthalate (2), glyceryl monostearate (3), tetracosanoic acid (4), 1-triacontanol (5), methyl oleate (6), methyl linolenate (7), octacosane (8), dotriacontane (9), -sitosterol (10), oleic acid (11), D-mannitol (12), bergenin (13), bis-(2-ethylhexyl) phthalate (14), taxayunnansin B (15), taxumairol E (16), daucosterol (17), (2, 5-dioxo-4-imidazolidinyl)-carbamic acid (18), rutin (19), tyrosine (20), galactitol (21). All these compounds were isolated from this plant for the first time, furthermore, the isolation of compounds 15 and 16 expanded the distribution of taxanes in plants and had potential resources value. Antioxidant activities of all the isolated compounds were tested. Results indicated that Compoud 19 (rutin) presented good activity on scavenging DPPH free radicals but the other compounds showed week activity. Chapter 2 Chemical and Antioxidant Constituents from Pistacia chinensis Pistacia chinensis Bunge., commonly named Chinese pistache, also known as Yellow Chinaberry, Kai-wood, Crest wood, Black Heart wood, Cliff Chinaberry and so on, is a deciduous tree belonging to genus Pistacia and family Anacardiaceae. It is a very important woody oil plant and its tender leaves, shoots and anthotaxy were favorite and delicious wild vegetable in Chinese folk. To further develop this wild vegetable resource, we studied on the chemical constituent of edible part of Pistacia chinensis Bunge., which was collected from Yuangjiang County Yunnan Province. 18 compounds were isolated from edible part of Pistacia chinensis Bunge. through using of various column chromatography methods. Based on spectral analyses (UV, IR, 1D, 2D NMR and MS) and comparison with reported literatures, their structures were elucidated as follows: ethyl linolenate (1), -sitosterol (2), 4-hydroxyphenylacetic acid (3), 3, 4, 5-trihydroxybenzoic acid ethyl ester (4), alnusdiol (5), amentoflavone (6), 4-hydroxybenzoic acid (7), 3, 4-dihydroxybenzoic acid (8), 3, 4, 5-trihydroxybenzoic acid (9), pistaciamide (10*), quercetin-3-O-β-D-xylopyranoside (11), rutin (12), daucosterol (13), quercetin-3-O-β-D-glucopyranoside (14), quercetin (15), kaempferol-3, 7-O-α-L-dirhamnoside (16), naringenin (17), 4-hydroxycinnamic acid (18), among which 10 is a new compound, compounds except 2, 4, 9, 14 and 15 were isolated from this plant for the first time. Their bioassay for scavenging DPPH free radicals test showed that compounds 4, 8, 9, 11, 12, 14 and 15 presented good activities and they were more effective than BHA at the same concentration. Key words: Yunnanopilia longistaminea (W. Z. Li) C. Y. Wu & D. Z. Li, Pistacia chinensis Bunge., Chemical constituents, Antioxidant activity
页数77
语种中文
文献类型学位论文
条目标识符http://ir.kib.ac.cn/handle/151853/232
专题昆明植物所硕博研究生毕业学位论文
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柳建军. 野生食用蔬菜甜菜树和黄连木化学成分及抗氧化活性[D]. 昆明植物研究所. 中国科学院昆明植物研究所,2008.
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