山刈葉根材之化學成分及抗血小板凝集成分之研究

周學駿

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山刈葉根材之化學成分及抗血小板凝集成分之研究

Chemical Constituents and Antiplatelet Aggregation Principles from the Root Wood of Melicope semecarpifolia

周學駿 , Masters　　Advisor：陳益昇　　

繁體中文

山刈葉；抗血小板凝集；芸香科； Rutaceae ； Melicope semecarpifolia ； Antiplatelet Aggregation

Abstract │ Reference (128) │ Altmetrics

Abstract 〈TOP〉

山刈葉 [Melicope semecarpifolia (Merr.) Hartley] 為常綠的小喬木，分布於台灣和菲律賓的低海拔森林中，山刈葉之根材具有抗血小板凝集之活性，且根材之化學成分尚未有人研究，因而引起分離化學及抗血小板凝集成分之動機。在氯仿可溶部分，分離得到1個新化合物，為benzenoid: melicopone (13)，及29個已知的化合物，包含8個quinolines: dictamnine (2), kokusaginine(7), (R)-(+)-platydesmine(9), edulinine (26), (S)-(-)-7,8-dimethoxyplatydesmine (10), pteleine (28), 
(+)-7,8-dimethoxymyrtopsine (11) 和(S)-(+)-geibalansine (27) ; 10個coumarins: angelicin (1), jatamansinol (3), (±)-columbianetin (5), oroselol (6), umbelliferone (8), seselin (16), osthenol (22), 7-O-prenylum-
belliferone (23), brosiparin (24),及 (+)-7-hydroxy-8-(2’-hydroxy-3’-me-
thylbut-3’-enyl) coumarin (30) ; 1個benzo[c]phenanthridine: oxynitidine (4) ; 5個benzenoids: vanillin (12), syringaldehyde (14), 3-(4-hydroxy-3-
methoxyphenyl) propionic acid (15), 2,6-dimethoxy-p-benzoquinone (17), 及benzoic acid (25) ; 1個flavonoid: ayanin (21) ; 1個lignans:(+)-4-keto-
pinoresinol (29) ，以及3個steroids之混合物:β-sitosterol (18), stigmasterol (19) 及campesterol (20)，這些化合物的結構經光譜分析證實。在天然界中，benzo[c]phenanthridine alkaloid的分布非常侷限，
而本研究首次自Melicope屬分離到oxynitidine，為本類生物鹼在芸香科之分布增加了一員。
化合物 (2)、(7)、(9)、(12)、(17)、(21)、(22) 及 (25) 具有抗血小板凝集活性，在100 μg/ml之濃度下in vitro之抗血小板凝集的活性已被研究而證實，本研究所測試抗血小板凝集活性之六個化合物，僅有(15) 在50μg/ml之濃度下，對於ADP所誘導之抗血小板凝集有抑制作用。

Parallel Abstract 〈TOP〉

Melicope semecarpifolia (Merr.) T. Hartley  is a small to medium sized evergreen trifoliated tree, distributed at lower altitude forest in Taiwan and the Philippines. The root wood of this plant have been used as a carminative in folk medicine. The root wood of this species showed antiplatelet aggregation activity in vitro and its chemical constituents have not been studied. Investigation on CHCl3-soluble fraction of the root wood of this species led to the isolation and characterization of a new benzenoid: melicopone (13), along with twenty-nine known compounds, including eight quinolines: dictamnine (2), kokusaginine (7), (R)-(+)-platydesmine (9), (S)-(-)-7,8-dimethoxypla-
tydesmine (10), edulinine (26), pteleine (28), (S)-(+)-geibalansine (27), and (+)-7,8-dimethoxymyrtopsine (11) ; ten coumarins: angelicin (1), jatamansinol (3), columbianetin (5), oroselol (6), umbelliferone (8), seselin (16) , osthenol (22), 7-O-prenylumbelliferone (23),  brosiparin (24), and (+)-7-hydroxy-8-(2’-hydroxy-3’-methylbut-3’-enyl) coumarin (30); one benzo[c]phenanthridine: oxynitidine (4); five benzenoids: vanillin (12), syringaldehyde (14), 3-(4-hydroxy-3-methoxyphenyl)- propionic acid (15), 2,6-dimethoxy-p-benzoquinone (17), and benzoic acid (25) ; one flavonoid: ayanin (21) ; one lignan: (+)-4-ketopinoresinol (29) and a mixture of β-sitosterol (18), stigmasterol (19), and campesterol (20). The structures of these compounds were elucidated by spectroscopic analysis. Benzo[c]phenanthridine alkaloids have a limited distribution in nature, and oxynitidine (4) isolated in this study, adds the Melicope genus into the members owning this kind of alkaloid. 
Compounds 2, 7, 9, 12 ,17, 21, 22 and 25 with anti-platelet aggregation activities under 100 μg/ml in vitro were reported previously. Compounds 1, 3, 6, 14, 15 and 16 were tested in vitro using a turbidimetric method, only 15 at 50 μg/ml showed good inhibition of platelet aggregation induced by ADP and the other compounds all showed no obvious activity.

Reference ( 128 ) 〈TOP〉

參考文獻
1. Chang, C, E. and Hartley, T. G.; Rutaceae in Flora of Taiwan, 2nd ed., Vol III, Editorial Committee of the Flora of Taiwan. Taipei, 1993: p. 522.
2. 甘偉松著，台灣藥用植物誌，國立中國醫藥研究所，台北， 1970; 2: p. 374.
3. But, K. M.; But, P. P. H.; Gray, A. I.; Hartley, T. G.; Kong, Y. C. and Waterman, P. G.; A chemotaxonomic division of Murraya based on the distribution of the alkaloids yuehchukene and girinimbine. Biochem. Syst. Ecol. 1987; 15: 587.
4. Rondest, J.; Das, B. C. and Polonsky, J.; Madagascan plants III. Constituents of Evodia belahe. J. Bull. Soc. Chim. 1968; 6: 2411.

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