Studies on Bioactive Sesquiterpene Lactones From Eupatorium hualienense, Ou, Chung & Peng

• Main Authors: Jiun-yang Jang, 張俊揚
• Other Authors: Ya-ching Shen
• Format: Others
• Language: zh-TW
• Published: 2004
• Online Access: http://ndltd.ncl.edu.tw/handle/53180332100265329885

碩士 === 國立中山大學 === 海洋資源學系研究所 === 92 === Sesquiterpene lactones contain α,β-unsaturated-γ-lactone as a major structural feature, which in recent studies have been shown to be associ- ated with anti-tumor, cytotoxic, anti-microbial and phytotoxic activities. Previous researchers isolated sesquiterpene lactones from Eupatorium formosanum Hay. Thus, we studied Eupatorium hualienense, a unique speces in Taiwan that grows near the eastern coast. Five new sesquiter- pene lactones of the germacranolide type, eupahualins A-E (1-5) along with the known lactone, eupasimplicin B (6). Their structures were determined by 1D-NMR(1H-NMR,13C-NMR) and 2D-NMR(COSY、NOESY、HMQC、HMBC). Eupahualin A (1) exhibits an aldehyde at C-10 and an a,b-unsatura ted acyl group at C-8. Eupahualin B (2) also has an aldehyde at C-10. The Z-form of C-4, C-5 double bond in eupahualin B (2) is the main difference from the trans-form C-4, C-5 double bond in eupahualin A (1). The difference of eupahualin C (3) and eupahualin A (1) lies in structure of a ester group at C-8. The methyl at C-4'' in eupahualin A (1) was changed into hydroxy methyl while the hydroxy methyl of eupahualin A (1) was changed to methyl in eupahualin C (3). Eupahualin D (4) shows exocyclic double bond at C-10, OH at C-1 and OAc at C-3. An carboxylic group (COOH) at C-10 in eupahualin E (5) is the only difference from which in eupahualin A (1).