台灣產黑潮花裙海葵化學成分及生物活性研究

本論文為台灣原生花群海葵屬之黑潮花裙海葵(Zoanthus kuroshio)的天然物化學與生物活性研究。將樣品萃取後經過一系列管柱層析純化，得到九個新生物鹼並命名為kuroshines A-I（1-9）和一個已知化合物（10）。所得到的化合物具有類似zoanthamine骨架的雜環結構，值得注意的是kuroshine A (1)為首次發現在C-10和C-28具有氧橋連接的化合物，kuroshine B（2）為首度出現在C-24與C-26酯化合環的化合物，其它新化合物kuroshines C-G（3-7）為化合物1的氧化代謝產物，這些生物鹼表現出台灣產菟葵的結構多樣性。化合物的結構鑑定主要利用光譜數據的分析，特別是2D-NMR(COSY, HMQC, HMBC, ROESY)和比對文獻上已知化合物的光譜資料而確定。化合物1的絕對立體構形是經由X-ray單晶繞射加以證明。同時黑潮花裙海葵是由外觀形態的辨別加上mt16s rDNA序列分析方法來完成鑑定。此為台灣首篇完成一系列花裙海葵鑑種之天然物化學研究論文。

關鍵字

海葵

並列摘要

The research topic of this thesis focuses on new natural product investigation from Taiwanese indigenous sea anemone. A zoanthid identified as Zoanthus kuroshio was extracted and subjected to a series of column chromatograph. As a result, nine new alkaloids named kuroshines A-I (1-9) and one know compound (10) were purified and identified. The isolates possess a densely functionalized ring system on the basis of the zoanthamine frames. It is noted that kuroshine A (1) is the first zoanthamine-type alkaloid with an ether bridge between C-10 and C-28 and kuroshine B (2) is the first zoanthamine-type alkaloid with an ester bridge between C-24 and C-26. They demonstrate a great structural diversity of Taiwanese zoanthid and new compounds (3-7) are recognized as a series of oxidation products of 1. The structures of all compounds were elucidated through interpretation of spectroscopic methods, especially 2D NMR techniques (COSY, HMQC, HMBC, and ROESY). The absolute stereochemistry of 1 was further confirmed by an X-ray single crystallographic analysis using a mirror Cu-Kα radiation. By the way , the species of research materials was identified by the mt16s rDNA sequencing method and morphology. This is the first studying combined natural product investigation and species identification for Taiwanese indigenous zoanthids.