臺灣產植物-食茱萸、岩山椒、翼柄花椒、香楠及紅莖椒草化學與生物活性成分之研究

對臺灣產植物─屬芸香科之食茱萸(Zanthoxylum ailanthoides)之根皮，岩山椒(Zanthoxylum beecheyanum)之莖部與翼柄花椒(Zanthoxylum schinifolium)之葉部; 屬樟科之香楠(Machilus zuihoensis)之莖材；屬胡椒科之紅莖椒草(Peperomia sui)之全草分別進行其化學成分及生物活性成分研究。在成分方面迄今從上述五種植物共分離得到301個化合物，除重覆分離物外，共分離到211個不同之化合物，有20個為新化合物。從食茱萸之根皮共分離到114個化合物，經光譜方法與文獻比對光譜資料後確認化合物之結構，其中有4個為天然界首次分離得到之新化合物，分別為: hydroxy lanyuamide I、hydroxy lanyuamide II、10β-methoxymuurolan-4-en-3-one及10α-methoxycadinan-4-en-3-one。所分離之化合物進行抗愛滋病之體外篩選生物活性研究，發現furoquinoline類化合物中之haplopine和γ-fagarine；benzo[c]phenanthridine類化合物中之decarine；coumarin中之O-methylcedrelopsin、isopimpinellin和5,7,8-trimethoxycoumarin；amide之(+)-tembamide和O-methyltambamide具有活性。從岩山椒之莖部獲得58個化合物，經光譜方法與文獻比對光譜資料後確認化合物之結構，其中有2個為天然界首次分離得到之新化合物，分別為: (+)-beechenol及beecheyamide。從翼柄花椒之葉部共得到51個化合物，經光譜方法與文獻比對光譜資料後確認化合物之結構，其中cis-fagaramide為天然界首次分離得到之新化合物。從岩山椒與翼柄花椒所分離之化合物進行抗血小板凝集之體外篩選生物活性研究。發現coumarin、benzo[c]phenanthridine、quinoline、aporphine類之化合物對AA、collagen與PAF所引起的血小板凝集有顯著的抑制作用。從香楠之莖材共分離出26個化合物，經光譜方法與文獻比對光譜資料後確認化合物之結構，其中有9個為天然界首次分離得到之新化合物，分別為: machilactone、machicolide A、machicolide B、secomahubanolide、3-(1-methoxy-octadecyl)-5-methylene-5H-furan-2-one、methyl (2E)-2-(1-hydroxy-2-oxopropyl)-eicos-2-enoate、mahubanolide, machillene及3,4-dihydroxy β-bisabolol。而從紅莖椒草之全草則得到52個化合物，經光譜方法、化學反應與文獻比對光譜資料後確認化合物之結構。其中有4個為天然界首次分離得到之新化合物，分別為: surinone A~C及suranone。從香楠與紅莖椒草所分離之化合物進行細胞毒殺之體外篩選生物活性研究。其中從香楠分離之methyl (2E)-2-(1-hydroxy-2-oxopropyl)-eicos-2-enoate、β-bisabolol和machillene; 紅莖椒草分離之proctorione C、surinone A、surinone C和peperomin E，分別對人類胃癌細胞(NUGC-3)與人類鼻咽癌細胞(HONE-1)均有抑制作用。

關鍵字

芸香科；樟科；胡椒科；食茱萸；岩山椒；翼柄花椒；香楠；紅莖椒草；成分；抗人類免疫缺乏病毒活性；抗血小板凝集活性；抗癌活性

並列摘要

As a series of studies on the chemical constituents and biological activities of Formosan plants, the root bark of Zanthoxylum ailanthoides (Rutaceae), the stem of Zanthoxylum beecheyanum (Rutaceae), the leaves of Zanthoxylum schinifolium (Rutaceae), the stem wood of Machilus zuihoensis (Lauraceae), the whole plants of Peperomia sui (Piperaceae) were investigated. Three hundred and one compounds have been isolated from the above plants and deduced the same constituents, 211 different compounds have been obtained. Among them, 20 compounds are new compounds. Four new compounds together with 110 known compounds were isolated and characterized from the root bark of Z. ailanthoides (Rutaceae). The structures were elucidated by spectral analyses and comparison of their physical and spectral data with literature. The new compounds included hydroxy lanyuamide I, hydroxy lanyuamide II, 10β-methoxymuurolan-4-en-3-one and 10α-methoxycadinan-4-en-3-one. Some of the isolated compounds were subjected to the evaluation of their anti-HIV activities. Furoquinolines [haplopine and γ-fagarine]；benzo[c]phenanthridine: [decarine]；coumarins: [O-methylcedrelopsin, isopimpinellin and 5,7,8-trimethoxycoumarin] and amides: [(+)-tembamide and O-methyltambamide] were found to possess significant anti-HIV activities. Two new compounds, (+)-beechenol and beecheyamide, together with 56 known compounds were separated and characterized from the stem of Z. beecheyanum (Rutaceae). The structures were elucidated by spectral analyses and comparison of their physical and spectral data with literature. One new compounds namely cis-fagaramide together with 50 known compounds were obtained and characterized from the leaves of Z. schinifolium (Rutaceae). Compounds isolated from Z. beecheyanum and Z. schinifolium were subjected to the evaluation of their anti-platelet aggregation activities. Some coumarins, benzo[c]phenanthridine, quinoline and aporphine showed significant inhibition of platelet aggregation induced by AA, collagen and PAF. Nine new compounds namely machilactone, machicolide A, machicolide B, secomahubanolide, 3-(1-methoxy-octadecyl)-5-methylene-5H-furan-2-one, methyl (2E)-2-(1-hydroxy-2-oxopropyl)-eicos-2-enoate, mahubanolide, machillene and 3,4-dihydroxy β-bisabolol together with 17 known compounds were obtained and characterized from the stem wood of M. zuihoensis (Lauraceae). The structures were elucidated by spectral analyses and comparison of their physical and spectral data with literature. Four new compounds, surinone A~C and suranone, together with 48 known compounds were obtained and characterized from the leaves of P. sui (Piperaceae). The structures were elucidated by means of spectral analyses and comparison of their physical and spectral data with literature. Some of the compounds isolated from M. zuihoensis and P. sui were subjected to the evaluation of cytotoxicity activities. Methyl (2E)-2-(1-hydroxy-2-oxopropyl)-eicos-2-enoate, β-bisabolol and machillene isolated from M. zuihoensis; proctorione C、surinone A、surinone C and peperomin E isolated from P. sui exhibited cytotoxic activity against NUGC-3 and HONE-1 tumor cell lines, respectively.

並列關鍵字

Rutaceae ； Lauraceae ； Piperaceae ； Zanthoxylum. ailanthoides ； Z. beecheyanum ； Z. schinifolium ； Machilus zuihoensis ； Peperomia sui ； constituent ； anti-HIV activity ； anti-platelet activity ； cytotoxicity

參考文獻

1. Chang, C. E.; Hartley, T. G. Rutaceae in Flora of Taiwan, Editorial Committee of the Flora of Taiwan, Taipei, Taiwan, 2nd. ed., Vol III, 1993, pp. 510-544.