栌菊木地上部分化学成分的研究
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摘要
栌菊木是菊科(Compositae)栌菊木属(Nouelia)植物，为我国特有的单种属植物，是菊科中稀有的木本残遗种。活性筛选中发现栌菊木(Nouelia insignis Franch)地上部分95％乙醇提取物具有α-淀粉酶抑制活性，为全面了解它们的成分及相关活性成分，本文首次对栌菊木地上部分的化学成分进行了深入系统的研究，从中分离得到了28个化合物，其中有2个新化合物和1个新的人工产物。综述了蒲公英赛烷型五环三萜的分离、纯化、结构鉴定、波谱特征以及生物活性方面的研究进展。
本文采用95％乙醇室温浸提，将所得浸膏悬浮于50℃热水中，依次用石油醚、乙酸乙酯和正丁醇萃取，粗分为四个部分；各部分再反复采用硅胶柱层析分离、Sephadex LH-20葡聚糖凝胶柱纯化，最终分离得到28个化合物。通过波谱分析、化学反应转化、X—射线单晶衍射实验或与已知品对照的方法对其进行了鉴定。
其中2个新化合物鉴定为：ent-14β，15α-dihydroxykaur-16-en-19-oic acid(1)和ent-14β-hydroxy-15-oxokaur-16-en-19-oic acid(2)；新的人工产物鉴定为：ent-15α-hydroxykaur-16-en-19-oic acid 11，12-acetonide(3)；已知化合物分别为：ent-11α,16α-epoxy-15α-hydroxy-16S-kaur-19-oic acid(4)，ent-15α-hydroxykaur-16-en-19-oic acid (5)，ent-11α,12α,15α-trihydroxykaur-16-en-19-oic acid (6)，ent-12α,15α-dihydroxykaur-16-en-19-oic acid(7)，8β，9-dihydro-onoseriolide(8)，蒲公英赛酮(9)，β-蒲公英赛醇(10)，α-蒲公英赛醇(11)，蒲公英赛醇乙酸酯(12)，2，6-二甲氧基对苯醌(13)，豆甾醇(14)，豆甾醇-3-氧-β-D-吡喃葡萄糖甙(15)，β-谷甾醇(16)，β-胡萝卜甙(17)，十六烷酸-1-甘油酯(18)，软脂酸(19)，二十四烷酸(20)，二十五烷醇(21)，蒲公英甾醇乙酸酯(22)，伪蒲公英甾醇乙酸酯(23)，咖啡酸(24)，蔗糖(25)，芦丁(26)，glutinol(27)和onoseriolid(28)。
Nouelia insignis Franch belongs to the family of Compositae; it is an endemic and rare plant as well as a monotype species of the genus Nouelia Franch in china. The in vitro activity-test indicated that the 95% ethanolic extract of the aerial parts of Nouelia insignis Franch showed a-amylase inhibitory activity. In order to further investigate chemical constituents and active compounds, the aerial parts of Nouelia insignis Franch was phytochemically studied for the first time. Twenty-eight compounds were isolated, two of which were new compounds and one was a new artifact.
The extract of 95% ethanol at room temperature was suspended in hot water and extracted successively with petroleum ether, EtOAc and n-BuOH to give corresponding four fractions, respectively. Twenty-eight compounds were isolated predominantly by silica gel and Sephedex LH-20 column chromatography and identified by spectral methods, chemical reaction, X-ray crystallographic analysis or comparing them with authentic samples.
Two new ent-kaurene-type diterpenes were identified as ent-14β, 15α-dihydroxykaur-16-en-19-oic acid (1) and ent-14β-hydroxy-15-oxokaur-16-en-19-oic acid (2); the new artifact was identified as ent-15α-hydroxykaur-16-en-19-oic acid 11,12-acetonide (3); twenty-five known compounds were ent-11α,16α-epoxy-15α-hydroxy-16S-kaur-19-oic acid (4), ent-15α-hydroxykaur-16-en-19-oic acid (5), ent-11α, 12α, 15α-trihydroxykaur-16-en-19-oic acid (6), ent-12α,15α-dihydroxykaur-16-en-19-oic acid (7), 8β,9-dihydro-onoseriolide (8), taraxerone (9),β-taraxerol (10),α-taraxerol (11), taraxeryl acetate (12), 2,6-dimethoxy-l,4-benzoquinone (13), stigmasterol (14), 3-O-β-D-glucopyranosyl stigmasterol (15),β-sitosterol (16),β-daucosterol (17), 2,3-dihydroxypropyl hexadecoate (18), palmitic acid (19), tetracosanoic acid (20), pentacosan-1-ol (21), taraxasteryl acetate (22), pseudo taraxasteryl acetate (23), caffeic acid (24), sucrose (25), rutin (26), glutinol (27), and onoseriolid (28).
本文采用95％乙醇室温浸提，将所得浸膏悬浮于50℃热水中，依次用石油醚、乙酸乙酯和正丁醇萃取，粗分为四个部分；各部分再反复采用硅胶柱层析分离、Sephadex LH-20葡聚糖凝胶柱纯化，最终分离得到28个化合物。通过波谱分析、化学反应转化、X—射线单晶衍射实验或与已知品对照的方法对其进行了鉴定。
其中2个新化合物鉴定为：ent-14β，15α-dihydroxykaur-16-en-19-oic acid(1)和ent-14β-hydroxy-15-oxokaur-16-en-19-oic acid(2)；新的人工产物鉴定为：ent-15α-hydroxykaur-16-en-19-oic acid 11，12-acetonide(3)；已知化合物分别为：ent-11α,16α-epoxy-15α-hydroxy-16S-kaur-19-oic acid(4)，ent-15α-hydroxykaur-16-en-19-oic acid (5)，ent-11α,12α,15α-trihydroxykaur-16-en-19-oic acid (6)，ent-12α,15α-dihydroxykaur-16-en-19-oic acid(7)，8β，9-dihydro-onoseriolide(8)，蒲公英赛酮(9)，β-蒲公英赛醇(10)，α-蒲公英赛醇(11)，蒲公英赛醇乙酸酯(12)，2，6-二甲氧基对苯醌(13)，豆甾醇(14)，豆甾醇-3-氧-β-D-吡喃葡萄糖甙(15)，β-谷甾醇(16)，β-胡萝卜甙(17)，十六烷酸-1-甘油酯(18)，软脂酸(19)，二十四烷酸(20)，二十五烷醇(21)，蒲公英甾醇乙酸酯(22)，伪蒲公英甾醇乙酸酯(23)，咖啡酸(24)，蔗糖(25)，芦丁(26)，glutinol(27)和onoseriolid(28)。
Nouelia insignis Franch belongs to the family of Compositae; it is an endemic and rare plant as well as a monotype species of the genus Nouelia Franch in china. The in vitro activity-test indicated that the 95% ethanolic extract of the aerial parts of Nouelia insignis Franch showed a-amylase inhibitory activity. In order to further investigate chemical constituents and active compounds, the aerial parts of Nouelia insignis Franch was phytochemically studied for the first time. Twenty-eight compounds were isolated, two of which were new compounds and one was a new artifact.
The extract of 95% ethanol at room temperature was suspended in hot water and extracted successively with petroleum ether, EtOAc and n-BuOH to give corresponding four fractions, respectively. Twenty-eight compounds were isolated predominantly by silica gel and Sephedex LH-20 column chromatography and identified by spectral methods, chemical reaction, X-ray crystallographic analysis or comparing them with authentic samples.
Two new ent-kaurene-type diterpenes were identified as ent-14β, 15α-dihydroxykaur-16-en-19-oic acid (1) and ent-14β-hydroxy-15-oxokaur-16-en-19-oic acid (2); the new artifact was identified as ent-15α-hydroxykaur-16-en-19-oic acid 11,12-acetonide (3); twenty-five known compounds were ent-11α,16α-epoxy-15α-hydroxy-16S-kaur-19-oic acid (4), ent-15α-hydroxykaur-16-en-19-oic acid (5), ent-11α, 12α, 15α-trihydroxykaur-16-en-19-oic acid (6), ent-12α,15α-dihydroxykaur-16-en-19-oic acid (7), 8β,9-dihydro-onoseriolide (8), taraxerone (9),β-taraxerol (10),α-taraxerol (11), taraxeryl acetate (12), 2,6-dimethoxy-l,4-benzoquinone (13), stigmasterol (14), 3-O-β-D-glucopyranosyl stigmasterol (15),β-sitosterol (16),β-daucosterol (17), 2,3-dihydroxypropyl hexadecoate (18), palmitic acid (19), tetracosanoic acid (20), pentacosan-1-ol (21), taraxasteryl acetate (22), pseudo taraxasteryl acetate (23), caffeic acid (24), sucrose (25), rutin (26), glutinol (27), and onoseriolid (28).
引文
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[2] 唐宇，刘建林．攀西珍稀濒危植物栌菊木的现状及保护措施[J]．西昌农业高等专科学校学报．2002，16(3)：1-2．
[3] 徐任生，叶阳，赵维民等．天然产物化学[M]．北京：科学出版社，2004，421-427．
[4] Dunstan WJ, Hughes GK, Smrrhson NL. A new source of taraxerol [J] . Nature. 1947, 160, 577.
[5] Brooks CJW. Observations on taraxerol (skimmiol) [J] . Chem. and Ind. 1955, 35, 1675.
[6] Wu TS (吴天赏), Zhang FZ (张凤珠), Wu PL (吴培琳), et al. Constituents of leaves of Tetradium glabrifollum [J] . J. chin. Chem.soc. 1995, 42 (6): 929-934.
[7] Williams LAD. Rhizophora mangle (Rhizophoraceae) Triterpenoids with insecticidal activity [J] . Naturwissenschaften. 1999, 86, 450-452.
[8] Sakurai N, Yaguchi Y, Inoue T. Treterpenoids from Myrica rubra [J] . Phytochemistry, 1987, 26, 217-219.
[9] 张仲平，战旗，王兴传．石沙参中三萜化合物的分离与结构鉴定[J]．中药材．1998，21(5)：238-239．
[10] Summon K, Razdan TK, Andotra CS. Acinospesigenin-A, -B, and -C: Three New Triterpenoids from Phytolacca acinosa [J] . J. Nat. Prod 2003, 66, 1121-1123.
[11] Prakash Chaturvedula VS, Jennifer KS, Stan M, et al. New cytotoxic triterpene acids from aboveground parts of Manihot esculenta from the suriname rainforest [J] . Plant Med. 2003, 69, 271-274.
[12] Buddha DP, Bose PK. Chemical examination of the bark of Luvunga scandens, Ham. Jour. lndian Chem. Soc. 1967, 44 (8): 659-662.
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