Radical Reaction Products from Curcumin
J. Agric. Food Chem., Vol. 47, No. 1, 1999 77
actions of nonnutritive substances in plant foods. In Anti-
oxidant Methodology in Vivo and in Vitro Concepts; Aruoma,
O. I., Cuppett, S. L., Eds.; AOCS Press: Champaign, IL,
1997; pp 173-204.
Brand-Williams, W.; Cuvelier, M. E.; Berset, C. Use of a free
radical method to evaluate antioxidant activity. Lebensm-
Wiss. -Technol. 1995, 28, 25-30.
Niki, E. Antioxidants in relation to lipid peroxidation. Chem.
Phys. Lipids 1987, 44, 227-253.
Pabon, H. J . J . A synthesis of curcumin and related com-
pounds. Recl. Trav. Chim. Pays-Bas 1964, 83, 379-385.
Ruby, A. J .; Kuttan, G.; Babu, K. D.; Rajasekharan, K. N.;
Kuttan R. Anti-tumour and antioxidant activity of natural
curcuminoids. Cancer Lett. 1995, 94, 79-83.
Govindarajan, V. S. Turmeric-chemistry, technology, and
quality. CRC Crit. Rev. Food Sci. Nutr. 1980, 12, 199-246.
Hall, III, C. A.; Cuppett, S. L. Structure-Activities of Natural
Antioxidants. In Antioxidant Methodology in Vivo and in
Vitro Concepts; Aruoma, O. I., Cuppett, S. L., Eds.; AOCS
Press: Champaign, IL, 1997; pp 141-172.
Sharma, O. P. Antioxidant activity of curcumin and related
compounds. Biochem. Pharmacol. 1976, 25, 1811-1812.
Toda, S.; Miyase, T.; Arichi, H.; Tanizawa, H.; Takino, Y.
Natural antioxidants III, antioxidative compornents isolated
from rhizomes of Curcuma longa. Chem. Pharm. Bull. 1985,
33, 1725-1728.
Huang, M. T.; Ferraro, T. Phenolic compounds in food and
cancer prevention. In Phenolic Compounds in Food and
Their Effects on Health II. Antioxidants and Cancer Preven-
tion; ACS Symposium Series 507; Houng, M. T., Ho, C. T.,
Lee, C. Y., Eds.; American Chemical Society: Washington,
DC, 1992; pp 8-34.
Kelloff, G. J .; Crowell, J . A.; Hawk, E. T.; Steele, V. E.; Lubet,
R. A.; Boone, C. W.; Covey, J . M.; Doody, L. A.; Omenn, G.
S.; Greenwald, P.; Hong, W. K.; Parkinson, D. R.; Bagheri,
D.; Baxter, G. T.; Blunden, M.; Doelts, M. K.; Eisenhauer,
K. M.; J ohnson, K.; Knapp, G. G.; Longfellow, D. G.; Malone,
W. F.; Nayfield, S. G.; Sefried, H. E.; Swall, L. M.; Sigman,
C. C. Strategy and planning for chemopreventive drug
development: clinical development plans II. J . Cell. Bio-
chem. 1996, 26S, 54-71.
Li, S.; Iliefski, T.; Lundquist, K.; Wallis, A. F. A. Reassignment
of relative stereochemistry at C-7 and C-8 in arylcoumarin
neolignan. Phytochemistry 1997, 46, 927-934.
Masuda, T.; J itoe, A. Antioxidative and antiinflammatory
compounds from tropical gingers: isolation, structure de-
termination, and activities of cassumunins A, B, and C, new
complex curcuminoids from Zingiber cassumunar. J . Agric.
Food Chem. 1994, 42, 1850-1856.
Masuda, T.; Isobe, J .; J itoe, A.; Nakatani, N. Antioxidative
curcuminoids from rhizomes of Curcuma xanthorrhiza.
Phytochemistry 1992, 31, 3645-3647.
Masuda, T.; J itoe, A.; Isobe, J .; Nakatani, N. Antioxidative and
antiinflammatory curcumin-related phenolics from rhizomes
of Curcuma domestica. Phytochemistry 1993, 32, 1557-
1560.
Masuda, T.; J itoe, A.; Mabry, T. J . Isolation and structure
determination of cassumunarins A, B, and C, new antiin-
flammatory antioxidants from a tropical ginger, Zingiber
cassumunar. J . Am. Oil Chem. Soc. 1995, 72, 1053-1057.
Tønnesen, H. H.; Karlsen, J . Studies on curcumin and cur-
cuminoids VI, kinetics of curcumin degradation in aqueous
solution. Z. Lebensm Unters. Forsch. 1985, 180, 402-404.
Tønnesen, H. H.; Karlsen, J .; van Henegouwen, G. B. Studies
on curcumin and curcuminoids VIII, photochemical stability
of curcumin. Z. Lebensm Unters. Forsch. 1986, 183, 116-
122.
Uehara, S.; Yasuda, I.; Akiyama, K.; Morita, H.; Takeya, K.;
Itokawa, H. Diarylheptanoids from the rhizomes of Cur-
cuma xanthorrhiza and Alpinia officinaraum. Chem. Pharm.
Bull. 1987, 35, 3298-3304.
Wang, Y.-J .; Pan M.-H.; Cheng, A.-L.; Lin L.-I.; Ho, Y.-S.;
Hsieh, C.-Y.; Lin, J .-K. Stability of curcumin in buffer
solutions and characterization of its degradation products.
J . Pharm. Biomed. Anal. 1997, 15, 1867-1876.
Winterle, J .; Dulin, D.; Mill, T. Products and Stoichiometry of
reaction of vitamin E with alkylperoxy radicals. J . Org.
Chem. 1984, 49, 491-495.
Yamauchi, R.; Matsui, T.; Kato, K.; Ueno, Y. Reaction of
R-tocopherol with 2,2′-azobis(2,4-dimethylvaleronitrile) in
benzene. Agric. Biol. Chem. 1989, 53, 3257-3262.
Zhang, N.; Kawakami, S.; Higaki, M.; Wee, V. T. New
oxidation pathway of 3,5,-di-tert-butyl-4-hydroxytoluene: an
ion spray tandem mass spectrometric and gass chromato-
graphic/mass spectrometric study. J . Am. Oil Chem. Soc.
1997, 74, 781-786.
Received for review May 20, 1998. Revised manuscript received
October 20, 1998. Accepted October 27, 1998. This work was
financially supported in part by a grant from Uragami
Foundation, Tokyo, J apan.
J F9805348