青箭化學成分及免疫調節活性之研究

Immune-modulating Activity and Chemical Constituents of Clinacanthus nutans

涂淑芬(Shu-Fen Tu)

指導教授 ： 張芳榮

共同指導教授 ： 吳永昌(Yang-Chang Wu)

高雄醫學大學/藥學院/天然藥物研究所碩士班/碩士(2012年)

摘要

青箭，為爵床科(Acanthaceae)、鱷嘴花屬(Clinacanthus)植物
Clinacanthus nutans，係一種小灌木，原產於熱帶亞洲地區。該植物在泰國很早即被當作傳統藥物，用於治療皮疹、昆蟲和蛇咬傷、單純皰疹病毒和水痘帶狀皰疹病毒。本研究於台中收集該植物的地上部(2.3 公斤)利用 95%乙醇抽提，再進行分配萃取，得到 n-hexane、80% EtOH aq.、n-BuOH、H2O 四層，80% EtOH aq.層具有顯著的免疫調節活性。
此研究利用層析法進行成分分離與純化，由青箭地上部分離純化得到27個純化合物，分別為7個含硫化合物： entadamide A (1)、2-cis-entadamide A (2)、trans-N-(2-(3-(2-hydroxyethylamino)-1-(methylthio)-3-oxopropoxy)ethyl)-3-methylthiopropenamide (3)、trans-N-(2-hydroxyethyl)-3-methylsulfonylpropenamide (4)、trans-2-(3-(methylsulfinyl)acrylamido)ethyl acetate (5)、entadamide C (6)、trans-3-methylsulfinyl-2-propenol (7)；3個 megastigmanes ： 3β-hydroxy-5α,6α-epoxy-7-megastimen-9-one (8)、loliolide (9)、3α-hydroxy-4,7-megastigmadien-9-one (10)；5個 benzenoids ： ethyl-trans-3-(4-hydroxyphenyl)prop-2-enoate (11)、ethyl-cis-3-(4-hydroxyphenyl)prop-2-enoate (12)、4-hydroxyacetophenone (13)、4-hydroxybenzaldehyde (14)、4-hydroxybenzoic acid (15)；1個 alkaloid： indole-3-aldehyde (16)；其餘11個未知化合物尚待解析。在這些化合物中2-5為新化合物；此外，2-5、7-16均為首次由鱷嘴花屬分離而得之化合物。以上化合物之結構式皆以質譜及光譜分析方法確認。
在生物活性方面，其萃取物具有顯著免疫調節活性，而純化合物之生物活性試驗正在進行中。

關鍵字

青箭 ； 鱷嘴花屬 ； 爵床科 ； 含硫化合物

並列摘要

Clinacanthus nutans (Acanthaceae) is a small shrub native to tropical Asia. The species has long been used in Thailand as a traditional medicine for the treatment of skin rashes, insect and snake bite, herpes simplex virus (HSV), and varicella-zoster virus (VZV) lesions. In this study, the cultivated materials were collected in Taichung, Taiwan. The aerial parts of C. nutans (2.3 kg) were extracted by 95% EtOH aq.. The extract was partitioned to yield four layers (n-hexane, 80% EtOH aq., n-BuOH, and H2O layers). Among the four layers, only the 80% EtOH aq. layer showed immune-modulating activity.
Chromatographic separation of the active layer yielded twenty-seven compounds. Among them, sixteen compounds were identified, including seven sulfur-containing compounds: entadamide A (1)、2-cis-entadamide A (2)、trans-N-(2-(3-(2-hydroxyethylamino)-1-(methylthio)-3-oxopropoxy)ethyl)-3-methylthiopropenamide (3)、trans-N-(2-hydroxyethyl)-3-methylsulfonylpropenamide (4)、trans-2-(3-(methylsulfinyl)acrylamido)ethyl acetate (5)、entadamide C (6)、trans-3-methylsulfinyl-2-propenol (7), three megastigmanes: 3β-hydroxy-5α,6α-epoxy-7-megastimen-9-one (8)、loliolide (9)、3α-hydroxy-4,7-megastigmadien-9-one (10), five benzenoids: ethyl-trans-3-(4-hydroxyphenyl)prop-2-enoate (11)、ethyl-cis-3-(4-hydroxyphenyl)prop-2-enoate (12)、4-hydroxyacetophenone (13)、4-hydroxybenzaldehyde (14)、4-hydroxybenzoic acid (15), one alkaloid: indole-3-aldehyde (16). The structures of the isolates were identified by spectral analysis. In addition, eleven unknown compounds are still under elucidating.
Compounds 2-5 and 7-16 were isolated for the first time from Clinacanthus genus. Among these ingredients, 2-5 are new compounds. The biological activities of isolates are currently under investigation.

並列關鍵字

Clinacanthus nutans ； Acanthaceae ； entadamide ； sulfur-containing compound

參考文獻

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4. Dampawan, P.; Huntrakul, C.; Reutrakul, V., Constituents of Clinacanthus nutans and the crystal structure of lup-20(29)-ene-3-one. J. Sci. Soc. Thailand 1977, 3, 14-26.