接骨木（Sambucus williamsii Hance）中抗骨质疏松生物活性成分的研究
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摘要
接骨木(Sambucus williamsii Hance)为忍冬科植物,主要功用有祛风、活血、治风湿筋骨疼痛,具有抗病毒、抗菌、抗炎、抗氧化作用、抗骨质疏松及免疫活性等药理作用。
本论文研究接骨木茎枝的抗骨质疏松活性成分。采用60%乙醇提取,经D101大孔树脂乙醇-水(0、30%、50%和95%)梯度洗脱,并利用UMR106细胞实验和去卵巢大鼠实验确定其有效部位为SW50(50%的流分)。SW50再经硅胶、Sephadex LH-20、ODS、制备型HPLC等各种现代分离手段进行分离纯化,并综合运用MS和NMR(1H、13C、DEPT135、HHCOSY、HMQC、HMBC)等波谱学方法进行结构鉴定,共得到16个化合物,其中13个木脂素类化合物,苯丙酸类、甾体类和环烯醚萜类各1个,分别为：阿魏酸(1),异落叶松树脂醇(2),胡萝卜苷(3),(2S,3R)-dihydrodehydodiconiferyl alcohol (4),erythro-guaiacylglycerol-β-O-4'-sinapyl ether (5),
1-(4'-hydroxy-3'-methoxyphenyl)-2-[4"-(3-hydroxypropyl)-2",6"-dimethoxyphenoxy]propane-1,3-diol (6),lyoniresinol (7),burselignan (8),5-甲氧基-异落叶松树脂醇(9),环橄榄树脂素(10),dehydrodiconiferyl alcohol-4-O-β-D-glucopyranoside (11),dihydrodehydrodiconiferyl alcohol-4-O-β-D-glucopyranoside (12),
(7S,8R)-dihydro-3'-hydroxy-8-hydroxy-methyl-7-(4-hydroxy-3-methoxy-phenyl)-1'-benzofuranpropanol(13),erythro-1-(4-hydroxy-3-methoxyphenyl)-2-[2-hydroxy-4-(3-hydroxypropyl)phenoxy]-1,3-propanediol (14),threo-1-(4-hydroxy-3-methoxyphenyl)-2-[2-hydroxy-4-(3-hydroxypropyl)phenoxy]-1,3-propanediol (15),莫诺苷(16)(其中α-莫诺苷大约占70%,β-莫诺苷占30%)。其中化合物2、5-11、14和15均为首次从该属植物中分离得到,化合物12和13为首次从该植物中分离得到。
建立有效部位SW50的液相指纹图谱,并占总峰面积70%以上的主要峰进行化合物指认。
这些单体化合物的抗骨质疏松活性正在测试中。
This thesis focuses on isolation and structure elucidation of bioactive constituents from the stems of Sambucus williamsii Hance.
The 60% ethanol extract of the stems of Sambucus williamsii Hance was eluted by Diaion D101 with a gradient of ethanol/water(0,30%,50% and 95%), and SW50(the fraction of 50%) was considered as the effective fraction by UMR106 cell's and ovariectomized rats'test. Then 16 compounds (including thirteen lignans, one phenylpropionic acid, one iridoid and one steroid) were isolated and purified from SW50 by silica gel, Sephadex LH-20, ODS chromatograph and Preparative HPLC. And their structures were identified by MS and NMR (1H,13C, DEPT135. HHCOSY, HMQC, HMBC)as:ferulic acid(1), isolariciresinol(2), daucosterol (3), (2S,3R)-dihydrodehydrodiconiferyl alcohol (4), erythro-guaiacylglycerol-β-O-4'-sinapyl ether (5), 1-(4'-hydroxy-3'-methoxyphenyl)-2-[4"-(3-hydroxypropyl)-2",6"-dimethoxyphenoxy]propane-1, 3-diol (6), lyoniresinol (7), burselignan (8),5-methoxy-isolariciresinol (9), cycloolivil (10), dehydrodiconiferyl alcohol-4-O-β-D-glucopyranoside (11),dihydrodehydrodiconiferyl alcohol-4-O-β-D-glucopyranoside (12), (7S,8R)-dihydro-3'-hydroxy-8-hydroxy-methyl-7-(4-hydroxy-3-methoxy-phenyl)-1'-benzofuranpropanol (13), erythro-1-(4-hydroxy-3-methoxyphenyl)-2-[2-hydroxy-4-(3-hydroxypropyl)phenoxy]-1,3-propanediol (14), threo-1-(4-hydroxy-3-methoxyphenyl)-2-[2-hydroxy-4-(3-hydroxypropyl)phenoxy]-1,3-propanediol (15), morroniside (16) with about 70%α-morroniside and 30%β-morroniside. Amongst these compounds,2,5-11,14 and 15 were isolated from this genus for the first time, and 12 and 13 were obtained from the plant for the first time.
The effective fraction SW50's HPLC fingerprint was established, and 8 mian peaks were identified.
These compounds' activities of the osteoblastic UMR106 cell are doing.
本论文研究接骨木茎枝的抗骨质疏松活性成分。采用60%乙醇提取,经D101大孔树脂乙醇-水(0、30%、50%和95%)梯度洗脱,并利用UMR106细胞实验和去卵巢大鼠实验确定其有效部位为SW50(50%的流分)。SW50再经硅胶、Sephadex LH-20、ODS、制备型HPLC等各种现代分离手段进行分离纯化,并综合运用MS和NMR(1H、13C、DEPT135、HHCOSY、HMQC、HMBC)等波谱学方法进行结构鉴定,共得到16个化合物,其中13个木脂素类化合物,苯丙酸类、甾体类和环烯醚萜类各1个,分别为：阿魏酸(1),异落叶松树脂醇(2),胡萝卜苷(3),(2S,3R)-dihydrodehydodiconiferyl alcohol (4),erythro-guaiacylglycerol-β-O-4'-sinapyl ether (5),
1-(4'-hydroxy-3'-methoxyphenyl)-2-[4"-(3-hydroxypropyl)-2",6"-dimethoxyphenoxy]propane-1,3-diol (6),lyoniresinol (7),burselignan (8),5-甲氧基-异落叶松树脂醇(9),环橄榄树脂素(10),dehydrodiconiferyl alcohol-4-O-β-D-glucopyranoside (11),dihydrodehydrodiconiferyl alcohol-4-O-β-D-glucopyranoside (12),
(7S,8R)-dihydro-3'-hydroxy-8-hydroxy-methyl-7-(4-hydroxy-3-methoxy-phenyl)-1'-benzofuranpropanol(13),erythro-1-(4-hydroxy-3-methoxyphenyl)-2-[2-hydroxy-4-(3-hydroxypropyl)phenoxy]-1,3-propanediol (14),threo-1-(4-hydroxy-3-methoxyphenyl)-2-[2-hydroxy-4-(3-hydroxypropyl)phenoxy]-1,3-propanediol (15),莫诺苷(16)(其中α-莫诺苷大约占70%,β-莫诺苷占30%)。其中化合物2、5-11、14和15均为首次从该属植物中分离得到,化合物12和13为首次从该植物中分离得到。
建立有效部位SW50的液相指纹图谱,并占总峰面积70%以上的主要峰进行化合物指认。
这些单体化合物的抗骨质疏松活性正在测试中。
This thesis focuses on isolation and structure elucidation of bioactive constituents from the stems of Sambucus williamsii Hance.
The 60% ethanol extract of the stems of Sambucus williamsii Hance was eluted by Diaion D101 with a gradient of ethanol/water(0,30%,50% and 95%), and SW50(the fraction of 50%) was considered as the effective fraction by UMR106 cell's and ovariectomized rats'test. Then 16 compounds (including thirteen lignans, one phenylpropionic acid, one iridoid and one steroid) were isolated and purified from SW50 by silica gel, Sephadex LH-20, ODS chromatograph and Preparative HPLC. And their structures were identified by MS and NMR (1H,13C, DEPT135. HHCOSY, HMQC, HMBC)as:ferulic acid(1), isolariciresinol(2), daucosterol (3), (2S,3R)-dihydrodehydrodiconiferyl alcohol (4), erythro-guaiacylglycerol-β-O-4'-sinapyl ether (5), 1-(4'-hydroxy-3'-methoxyphenyl)-2-[4"-(3-hydroxypropyl)-2",6"-dimethoxyphenoxy]propane-1, 3-diol (6), lyoniresinol (7), burselignan (8),5-methoxy-isolariciresinol (9), cycloolivil (10), dehydrodiconiferyl alcohol-4-O-β-D-glucopyranoside (11),dihydrodehydrodiconiferyl alcohol-4-O-β-D-glucopyranoside (12), (7S,8R)-dihydro-3'-hydroxy-8-hydroxy-methyl-7-(4-hydroxy-3-methoxy-phenyl)-1'-benzofuranpropanol (13), erythro-1-(4-hydroxy-3-methoxyphenyl)-2-[2-hydroxy-4-(3-hydroxypropyl)phenoxy]-1,3-propanediol (14), threo-1-(4-hydroxy-3-methoxyphenyl)-2-[2-hydroxy-4-(3-hydroxypropyl)phenoxy]-1,3-propanediol (15), morroniside (16) with about 70%α-morroniside and 30%β-morroniside. Amongst these compounds,2,5-11,14 and 15 were isolated from this genus for the first time, and 12 and 13 were obtained from the plant for the first time.
The effective fraction SW50's HPLC fingerprint was established, and 8 mian peaks were identified.
These compounds' activities of the osteoblastic UMR106 cell are doing.
引文
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