Nitrocapsanthin and Nitrofucoxanthin, Respective Products of Capsanthin and Fucoxanthin Reaction with Peroxynitrite

The in vitro reactivity of capsanthin (1) and fucoxanthin (2) with peroxynitrite was investigated, and the reaction products produced by scavenging with peroxynitrite were analyzed. (14′Z)-Nitrocapsanthin (3) and 12-nitrocapsanthin (4) were isolated from the products of the reaction of capsanthin wi...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2011-10, Vol.59 (19), p.10572-10578
Main Authors: Tsuboi, Makoto, Etoh, Hideo, Kato, Kyuki, Nakatugawa, Hiroki, Kato, Hideki, Maejima, Yasunori, Matsumoto, Gaku, Mori, Hironobu, Hosokawa, Masashi, Miyashita, Kazuo, Tokuda, Harukuni, Suzuki, Nobukuni, Maoka, Takashi
Format: Article
Language:English
Subjects:
Animals
anthracenes
Anticarcinogenic Agents - pharmacology
antigens
Biological and medical sciences
Burkitt Lymphoma
capsanthin
carcinoma
Cell Line, Tumor
Chemical Composition of Foods/Feeds
Female
Food industries
Free Radical Scavengers - chemistry
Fundamental and applied biological sciences. Psychology
Humans
Mice
Mice, Inbred ICR
Pancreatic Neoplasms
Papilloma - prevention & control
Peroxynitrous Acid - chemistry
Skin Neoplasms - chemically induced
Skin Neoplasms - prevention & control
tyrosine
Tyrosine - analogs & derivatives
Tyrosine - antagonists & inhibitors
Tyrosine - chemistry
viruses
Xanthophylls - chemistry
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Summary:The in vitro reactivity of capsanthin (1) and fucoxanthin (2) with peroxynitrite was investigated, and the reaction products produced by scavenging with peroxynitrite were analyzed. (14′Z)-Nitrocapsanthin (3) and 12-nitrocapsanthin (4) were isolated from the products of the reaction of capsanthin with peroxynitrite. Similarly, (14Z)-15-nitrofucoxanthin (5), (11Z)-11-nitrofucoxanthin (6), and (14Z,9′Z)-15-nitrofucoxanthin (7) were obtained from the reaction of peroxynitrite reaction with fucoxanthin. Capsanthin and fucoxanthin inhibited the nitration of tyrosine by peroxynitrite. Furthermore, nitrocapsanthins (3 and 4) and nitrofucoxanthins (5 and 6) exhibited an inhibitory effect on Epstein–Barr virus early antigen activation in Raji cells and an antiproliferative effect on human pancreatic carcinoma. Moreover, nitrocapsanthins (3 and 4) inhibited carcinogensis of mouse skin tumors initiated by 7,12-dimethylbenz[a]anthracene (DMBN).
ISSN:0021-8561
1520-5118
DOI:10.1021/jf203493k