婆婆针有效部位化学成分的研究
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摘要
婆婆针(Bidens bipinnata)是菊科鬼针草属植物，民间药用历史悠久，治疗作用广泛，疗效确切，药材资源丰富。在鬼针草属二百三十余种植物中，婆婆针是国内研究最多的种之一，而国外研究却较少。药理作用研究表明，婆婆针具有抗炎作用、抑菌作用、对心血管系统的作用及抗肿瘤作用。聚炔类成分和黄酮类成分是其主要的有效成分。
国内外文献检索表明，对婆婆针中聚炔类成分研究较少，黄酮类成分研究也有待于进一步开展。为此，我们对婆婆针中的有效成分进行了系统分离，采用硅胶柱、聚酰胺柱、高效液相制备色谱等方法，从婆婆针中得到单体化合物10个，鉴定了其中6个，分别为：鬼针聚炔苷(1)，2-β-D-吡喃葡萄糖基-1，13-二羟基-11(反)-十三烯-3，5，7，9-四炔(2)，金丝桃苷(3)，7，3’，4’-三羟基-6-(3”，6”-二乙酰氧基-β-D-吡喃葡萄糖基)-橙酮(4)，7，3’，4’-三羟基-6-(6”-乙酰氧基-β-D-吡喃葡萄糖基)-橙酮(5)，7，3’，4’-三羟基-6-(4”，6”-二乙酰氧基-β-D-吡喃葡萄糖基)-橙酮(6)。
化合物2经国际联机检索，为首次发现的新成分，命名为鬼针聚炔苷B(bipinnatapolyacetyloside B)。化合物4未经国际联机检索，但经查询CA分子式索引也为首次发现的新成分。化合物5为首次从该种植物中得到。上述研究为婆婆针的新药开发提供了依据。
Bidens bipinnata,a weed of the compositae family,is widely distributed in China,and has been used as a traditional Chinese folk medicine for a long time.Studies of the biological activities show that Bidens bipinnata has anti-inflammatory activity ,antimicrobial activity,cardiovascular activity and antileukemia activity.Polyacetylenes and flavones are the main active chemical constituents of Bidens bipinnata.
Little work has been done to study the polyacetylenes constituents of Bidens bipinnata,and its flavones constituents also need studying.In this chemical study on Bidens bipinnata,after repeating silica gel,reversed phase silica gel column chromatography and polyamide column chromatography,we obtained ten compounds,and identified six compounds'structures.The six compounds are: trideca-2-p-D-glucopyranosyl-1,13-dihydroxy-3(E),11(E)-di en-5,7,9-triyne(l), trideca-2-p-D-glucopyranosyl-l,13-dihydroxy-11(E)-dien -3,5,7,9-tetrayne(2),Hyperoside(3),6-O-(3",6"-diacetyl-p-D-glucopyranosyl)-6,7,3',4'-tetrahydroxyaurone(4),6-O-(6"-acetyl-p-D-glucopyranosyl)6,7,3',4' -tetrahydroxyaurone(S), 6-O-(4",6"-diacetyI-p-D-glucopyranosyl)6,7,3',4'-te tr'ahydroxyaurone(6) .
Compound2 and compound4 are two new compounds,compound5 is first isolated from this plant.
国内外文献检索表明，对婆婆针中聚炔类成分研究较少，黄酮类成分研究也有待于进一步开展。为此，我们对婆婆针中的有效成分进行了系统分离，采用硅胶柱、聚酰胺柱、高效液相制备色谱等方法，从婆婆针中得到单体化合物10个，鉴定了其中6个，分别为：鬼针聚炔苷(1)，2-β-D-吡喃葡萄糖基-1，13-二羟基-11(反)-十三烯-3，5，7，9-四炔(2)，金丝桃苷(3)，7，3’，4’-三羟基-6-(3”，6”-二乙酰氧基-β-D-吡喃葡萄糖基)-橙酮(4)，7，3’，4’-三羟基-6-(6”-乙酰氧基-β-D-吡喃葡萄糖基)-橙酮(5)，7，3’，4’-三羟基-6-(4”，6”-二乙酰氧基-β-D-吡喃葡萄糖基)-橙酮(6)。
化合物2经国际联机检索，为首次发现的新成分，命名为鬼针聚炔苷B(bipinnatapolyacetyloside B)。化合物4未经国际联机检索，但经查询CA分子式索引也为首次发现的新成分。化合物5为首次从该种植物中得到。上述研究为婆婆针的新药开发提供了依据。
Bidens bipinnata,a weed of the compositae family,is widely distributed in China,and has been used as a traditional Chinese folk medicine for a long time.Studies of the biological activities show that Bidens bipinnata has anti-inflammatory activity ,antimicrobial activity,cardiovascular activity and antileukemia activity.Polyacetylenes and flavones are the main active chemical constituents of Bidens bipinnata.
Little work has been done to study the polyacetylenes constituents of Bidens bipinnata,and its flavones constituents also need studying.In this chemical study on Bidens bipinnata,after repeating silica gel,reversed phase silica gel column chromatography and polyamide column chromatography,we obtained ten compounds,and identified six compounds'structures.The six compounds are: trideca-2-p-D-glucopyranosyl-1,13-dihydroxy-3(E),11(E)-di en-5,7,9-triyne(l), trideca-2-p-D-glucopyranosyl-l,13-dihydroxy-11(E)-dien -3,5,7,9-tetrayne(2),Hyperoside(3),6-O-(3",6"-diacetyl-p-D-glucopyranosyl)-6,7,3',4'-tetrahydroxyaurone(4),6-O-(6"-acetyl-p-D-glucopyranosyl)6,7,3',4' -tetrahydroxyaurone(S), 6-O-(4",6"-diacetyI-p-D-glucopyranosyl)6,7,3',4'-te tr'ahydroxyaurone(6) .
Compound2 and compound4 are two new compounds,compound5 is first isolated from this plant.
引文
[1] 江苏新医学院．中药大辞典．上海：上海科技出版社，1986：1694．
[2] 王建平，秦红岩，张惠云等．鬼针草提取成分对白血病细胞的体外抑制作用．《中药材》，1997，20(5)：247～248．
[3] Jian Ping WANG, Hisashi ISHII,Takashi HARAYAMA.Study on the chemical constituents of Bidens bipinnata:a new polyacetylene glucoside.Chinene Chemical Letter, 1992, 3(4): 287～288.
[4] 龚运淮．天然有机化合物的~(13)C核磁共振化学位移．昆明：云南科技出版社，1986年3月，第一版．
[5] 马天波，李军林，袁久荣．小花鬼针草叶中黄酮苷的分离与鉴定．中草药，1991，22(12)：531～533．
[6] Jia WANG, Hui YANG, Zhong Wen LIN.Five new flavonoids from Bidens pilosa L.Var. Vadiata. SCH-BIP. Chinese Chemical Letters, 1997, 8(7):59 9～602.
[7] Bernhard Hoffmann,Josef Holzl. Chalcone glucosides from Bidens pilosa. Phytochemistry, 1989, 28(1):247～249.
[8] Nunziatina De Tommasi,Cosimo Pizza. Flavonol and chalcone ester glycosides from Bidens leucantha. J.Nat. Prod, 1997, 60:270～273.
[9] G. Rucker, S.Kehrbaum,H.Sakulas. Acetylated aurone glucosides from Microglossa pyrifolia. Planta Med, 1994, 60:288～289.
[10] Yutaka Sashida,Kazunori Ogawa,Makoto Kitada. New aurone glucosides and new phenylpropanoid glucosides from Bidens pilosa. Chem. Pharm. Bull, 1991, 39(3): 709～711.
[11] 黄量，于德泉．紫外光谱在有机化学中的应用(下册)．北京：科学出版社，1988年9月，第一版：252．
[12] 王建平，张惠云，秦红岩等．鬼针草抗炎新成分的药理作用．中草药，1997，28(11)：665～667．
[13] 王建平，高玉敏，秦红岩等．鬼针草抗炎有效成分及抗氧化作用研究．实用中医药杂志，1996，12(5)：57．
[2] 王建平，秦红岩，张惠云等．鬼针草提取成分对白血病细胞的体外抑制作用．《中药材》，1997，20(5)：247～248．
[3] Jian Ping WANG, Hisashi ISHII,Takashi HARAYAMA.Study on the chemical constituents of Bidens bipinnata:a new polyacetylene glucoside.Chinene Chemical Letter, 1992, 3(4): 287～288.
[4] 龚运淮．天然有机化合物的~(13)C核磁共振化学位移．昆明：云南科技出版社，1986年3月，第一版．
[5] 马天波，李军林，袁久荣．小花鬼针草叶中黄酮苷的分离与鉴定．中草药，1991，22(12)：531～533．
[6] Jia WANG, Hui YANG, Zhong Wen LIN.Five new flavonoids from Bidens pilosa L.Var. Vadiata. SCH-BIP. Chinese Chemical Letters, 1997, 8(7):59 9～602.
[7] Bernhard Hoffmann,Josef Holzl. Chalcone glucosides from Bidens pilosa. Phytochemistry, 1989, 28(1):247～249.
[8] Nunziatina De Tommasi,Cosimo Pizza. Flavonol and chalcone ester glycosides from Bidens leucantha. J.Nat. Prod, 1997, 60:270～273.
[9] G. Rucker, S.Kehrbaum,H.Sakulas. Acetylated aurone glucosides from Microglossa pyrifolia. Planta Med, 1994, 60:288～289.
[10] Yutaka Sashida,Kazunori Ogawa,Makoto Kitada. New aurone glucosides and new phenylpropanoid glucosides from Bidens pilosa. Chem. Pharm. Bull, 1991, 39(3): 709～711.
[11] 黄量，于德泉．紫外光谱在有机化学中的应用(下册)．北京：科学出版社，1988年9月，第一版：252．
[12] 王建平，张惠云，秦红岩等．鬼针草抗炎新成分的药理作用．中草药，1997，28(11)：665～667．
[13] 王建平，高玉敏，秦红岩等．鬼针草抗炎有效成分及抗氧化作用研究．实用中医药杂志，1996，12(5)：57．