皮孫木莖部化學與抗結核活性成分之研究

紫茉莉科(Nyctaginaceae) 植物皮孫木(Pisonia umbellifera Seem.)，為常綠喬木，分布於澳洲、爪哇、馬來西亞、夏威夷、馬達加斯加、密克羅西尼亞以及台灣。其莖部甲醇抽出物對Mycobacterium tuberculosis M37RV 具有抗結核菌活性，經進行分配萃取後，得到正己烷、乙酸乙酯、正丁醇及水四個可溶部的抽出物。其中乙酸乙酯層抽出物顯示具有完全抑制結核菌的活性。本研究由正己烷層及乙酸乙酯抽出物進行化學成分研究，共獲得34 個化合物，其中有1 個isoflavone： 6,8-dimethylisogenistein (1)；1 個isoquinolinone： 3,4-dihydro-6-hydroxy-7-methoxyisoquinolin-1(2H)-one (2)；2 個quinones： 3,4,4,5-tetramethoxycyclohexa-2,5-dienone (3) 和2,6-dimethoxy-1,4-benzoquinone (4) ；1 個quinol：4-acetonyl-3,5-dimethoxy-p-quinol (5)；14 個benzenoids：(+)-ent-ficusol (6), goldfiussinol (7), pisoninol I (8), pisoninol II (9), pavonisol (10), β-hydroxypropiovanillone (11), β-hydroxypropisosyringone (12), α-hydroxypropiovanillone (13), α-hydroxypropisosyringone (14), C-veratroylglycol (15), trans-methyl ferulate (16), vanillin (17), syringaldehyde (18)與methyl syringate (19) ；5 個triterpenoids： 24-methylene-3,4-seco-cycloart-4(28)-en-3-oic acid (20), secopisonic acid (21), oleanolic acid (22), oleanonic acid (23) 和29-hydroxy-3-oxo-olean-12-en-28-oic acid (24)；2 個amides：N-transferuloyl- 4'-O-methyldopamine (25)和N-trans-feruloyltyramine (26)； 2 個lignans：(+)-syringaresinol (27)和(+)-glaberide I (28) ；4 個steroids：ergosterol peroxide (29)、α-spinasterol (30)以及混合物β-sitosterol (31)和stigmasterol (32)；1 個葉綠素類：132-hydroxy-(132S)-pheophytin-a (33)以及1 個β-tocopherol (34)。以上化合物皆以光譜分析來決定其結構。所有分離得到的化合物中，化合物 1, 6 和21 為新化合物，而2, 3, 8 及9 為天然首次分離得到之化合物，而化合物9, 17, 25 和26 顯示具抗結核菌之活性。

關鍵字

皮孫木；紫茉莉科；莖部；抗結核活性

並列摘要

Pisonia umbellifera Seem. (Nyctaginaceae) is an evergreen tree, which distributed in Australia, Java, Malaysia, Hawaii, Madagascar, Micronesia, and Taiwan. The MeOH extract of the stem showed antitubercular activity against Mycobacterium tuberculosis H37RV, that was partitioned into n-hexane, EtOAc, n-BuOH and H2O-soluble parts. The EtOAc-soluble part showed significant antitubercular activity. Investigation of the n-hexane-soluble extract and EtOAc-soluble extract led to the isolation of thirty-four compounds, including one isoflavone: 6,8- dimethylisogenistein (1); one isoquinolinone: 3,4-dihydro-6-hydroxy-7-methoxyisoquinolin-1(2H)-one (2); two quinones: 3,4,4,5-tetramethoxy-cyclohexa-2,5-dienone (3) and 2,6-dimethoxy-1,4-benzoquinone (4); one quinol: 4-acetonyl-3,5-dimethoxy-p-quinol (5); fourteen benzenoids: (+)-ent-ficusol (6), goldfiussinol (7), pisoninol (8), pisoninol II (9), pavonisol (10), β-hydroxypropiovanillone (11), β-hydroxypropisosyringone (12), α-hydroxypropiovanillone (13), α-hydroxypropisosyringone (14), C-veratroylglycol (15), trans-methyl ferulate (16), vanillin (17), syringaldehyde (18) and methyl syringate (19); five triterpenoids: 24-methylene-3,4-seco-cycloart-4(28)-en-3-oic acid (20), secopisonic acid (21), oleanolic acid (22), oleanonic acid (23) and 29-hydroxy-3-oxoolean- 12-en-28-oic acid (24); two amides: N-trans-feruloyl-4’-Omethyldopamine (25), N-trans-feruloyltyramine (26); two lignans:(+)-syringaresinol (27) and (+)-glaberide I (28); four steroids: ergosterol peroxide (29), α-spinasterol (30), mixture of β-sitosterol (31) and stigmasterol (32); one chlorophyll: 132-hydroxy-(132S)-pheophytin-a (33), and β-tocopherol (34). The structures of these compounds were elucidated by the spectral analysis. Among these isolates, 1, 6 and 21 are new compounds, and compound 2, 3, 8 and 9 were first isolated from natural source. Compounds 9, 17, 25 and 26 showed antitubercular activity in vitro.