Synthesis of (±)-cassumunin A, a potent antiinflammatory antioxidant from a medicinal ginger

Natural Product Letters

Volumn 10, Issue 1, 1997, Pages 13-16

  Masuda, Toshiya ^a   Jitoe, Akiko ^b   Kida, Atsuko ^b   Takeda, Yoshio ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

Antiinflammation; Antioxidant; Cassumunin A; Curcumin; Curcuminoid; Synthesis

Indexed keywords

ANTIINFLAMMATORY AGENT; ANTIOXIDANT; CASSUMUNIN A; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; MEDICINAL PLANT;

EID: 0030936887     PISSN: 10575634     EISSN: None     Source Type: Journal    
DOI: 10.1080/10575639708043689     Document Type: Article

References (9)

1. A. Ramirezbosca, A. Soler, M. A. C. Guitierrez, J. L. Alvarez, E. Q. Almagro (1995). Antioxidant Curcuma Extracts decrease the Blood Lipid Peroxide Levels of human Subjects. Age, 18, 167-169.
2. B. Halliwell, J. M. C. Gutteridge, (1985) Free Radicals in Biology and Medicine, Oxford Univ. Press: Oxford.
3. A. Jitoe, T. Masuda, I. G. P. Tengah, D. N. Suprapta, I. W. Gara, N. Nakatani (1992). Antioxidant Activity of Tropical Ginger Extracts and Analysis of the Contained Curcuminoids. J. Agric. Food Chem., 40, 1337-1340.
4. T. Masuda, A. Jitoe (1994). Antioxidative and Antiinflammatory Compounds from Tropical Gingers: Isolation, Structure Determination, and Activities of Cassumunins A, B, and C, New Complex Curcuminoids from Zingiber cassumunar. J. Agric. Food Chem., 42, 1850-1856.
5. A. Jitoe, T. Masuda, T. J. Mabry (1994). Novel Antioxidants, Cassumunarin A, B, and C, from Zingiber cassumunar. Tetrahedron Lett., 35, 981-984.
6. H. H. Tønnesen, J. Karlsen, A. Mostad (1982). Structural Studies of Curcuminids. I. Acta Chem. Scand., 36, 475-479.
7. M. -T. Huang, R. C. Smart, C. -Q. Wong, A. H. Conney (1988). Inhibitory Effect of Curcumin, Chlorogenic Acid, Caffeic Acid, and Ferulic Acid on Tumor Promotion in Mouse Skin by 12-O-Tetradecanoylphorbol-13-acetate. Cancer Research, 48, 5941-5946
8. H. J. J. Pabon (1964). Synthesis of Curcumin and Related Compounds.Recl. Trav. Chim. Pays-Bas., 83, 379-385.
9. 3) δ 7.58 (2H, brd, J=15.6 Hz), 7.12 (1H, brd, J=8 Hz), 7.07 (1H, brs), 7.05 (1H, brs), 6.96 (1H, brs), 6.93 (1H, d, J=8 Hz), 6.91 (1H, brs), 6.89 (1H, brd, J=8 Hz), 6.80 (1H, d, J=7.6 Hz), 6.46 (2H, d, J=15.6 Hz), 6.40 (1H, d, J=16 Hz), 6.29 (1H, dd, J=16 and 7 Hz), 6.03 (1H, s), 5.84 (1H, s), 5.81 (1H, s), 4.05 (1H, m), 3.95 (3H, s), 3.94 (3H, s), 3.89 (3H, s), 3.87 (3H, s), 1.46 (3H, d, J=7 Hz); EIMS m/z 558 (M+).