Synthesis of (±)-cassumunins A and B, new curcuminoid antioxidants having protective activity of the living cell against oxidative damage

被引:33
作者
Masuda, T [1 ]
Matsumura, H
Oyama, Y
Takeda, Y
Jitoe, A
Kida, A
Hidaka, K
机构
[1] Univ Tokushima, Fac Integrated Arts & Sci, Tokushima 770, Japan
[2] Osaka City Univ, Fac Human Life Sci, Osaka 558, Japan
来源
JOURNAL OF NATURAL PRODUCTS | 1998年 / 61卷 / 05期
关键词
D O I
10.1021/np970555g
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
A chemical synthesis of cassumunins A (1) and B (2), natural curcuminoid antioxidants, was developed. The synthesis was started from o-vanillin and after nine reaction steps resulted in 20% and 26% overall yields of 1 and 2, respectively. The synthetic cassumunins showed stronger protective activity than curcumin against oxidative cell death induced by hydrogen peroxide in a rat thymocyte system.
引用
收藏
页码:609 / 613
页数:5
相关论文
共 17 条
[1]   PHARMACOLOGY OF CURCUMA-LONGA [J].
AMMON, HPT ;
WAHL, MA .
PLANTA MEDICA, 1991, 57 (01) :1-7
[2]   EVIDENCE OF AN OXIDATIVE CHALLENGE IN THE ALZHEIMERS BRAIN [J].
BALAZS, L ;
LEON, M .
NEUROCHEMICAL RESEARCH, 1994, 19 (09) :1131-1137
[3]   Fluorescent estimation of H2O2-induced changes in cell viability and cellular nonprotein thiol level of dissociated rat thymocytes [J].
Chikahisa, L ;
Oyama, Y ;
Okazaki, E ;
Noda, K .
JAPANESE JOURNAL OF PHARMACOLOGY, 1996, 71 (04) :299-305
[4]   Dietary antioxidants in disease prevention [J].
Gordon, MH .
NATURAL PRODUCT REPORTS, 1996, 13 (04) :265-273
[5]   TURMERIC - CHEMISTRY, TECHNOLOGY, AND QUALITY [J].
GOVINDARAJAN, VS .
CRC CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION, 1980, 12 (03) :199-301
[6]   NOVEL ANTIOXIDANTS, CASSUMUNARIN-A, CASSUMUNARIN-B, AND CASSUMUNARIN-C, FROM ZINGIBER CASSUMUNAR [J].
JITOE, A ;
MASUDA, T ;
MABRY, TJ .
TETRAHEDRON LETTERS, 1994, 35 (07) :981-984
[7]   ANTIOXIDANT ACTIVITY OF TROPICAL GINGER EXTRACTS AND ANALYSIS OF THE CONTAINED CURCUMINOIDS [J].
JITOE, A ;
MASUDA, T ;
TENGAH, IGP ;
SUPRAPTA, DN ;
GARA, IW ;
NAKATANI, N .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1992, 40 (08) :1337-1340
[8]  
KELLOFF GJ, 1994, CANCER EPIDEM BIOMAR, V3, P85
[9]   STRUCTURES OF CASSUMUNIN A, B, AND C, NEW POTENT ANTIOXIDANTS FROM ZINGIBER-CASSUMUNAR [J].
MASUDA, T ;
JITOE, A ;
NAKATANI, N .
CHEMISTRY LETTERS, 1993, (01) :189-192
[10]   ANTIOXIDATIVE AND ANTIINFLAMMATORY COMPOUNDS FROM TROPICAL GINGERS - ISOLATION, STRUCTURE DETERMINATION, AND ACTIVITIES OF CASSUMUNIN-A, CASSUMUNIN-B, AND CASSUMUNIN-C, NEW COMPLEX CURCUMINOIDS FROM ZINGIBER-CASSUMUNAR [J].
MASUDA, T ;
JITOE, A .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1994, 42 (09) :1850-1856