Nitrocapsanthin and nitrofucoxanthin, respective products of capsanthin and fucoxanthin reaction with peroxynitrite.

Abstract

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).

• Authors: Makoto Tsuboi, Hideo Etoh, Kyuki Kato, Hiroki Nakatugawa, Hideki Kato, Yasunori Maejima, Gaku Matsumoto, Hironobu Mori, Masashi Hosokawa, Kazuo Miyashita, Harukuni Tokuda, Nobukuni Suzuki, Takashi Maoka
• Journal: Journal of agricultural and food chemistry (J Agric Food Chem) Vol. 59 Issue 19 Pg. 10572-8 (Oct 12 2011) ISSN: 1520-5118 [Electronic] United States
• PMID: 21899264 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Anticarcinogenic Agents
• Free Radical Scavengers
• Xanthophylls
• nitrocapsanthin
• nitrofucoxanthin
• fucoxanthin
• Peroxynitrous Acid
• 3-nitrotyrosine
• capsanthin
• Tyrosine

Topics

• Animals
• Anticarcinogenic Agents (pharmacology)
• Burkitt Lymphoma
• Cell Line, Tumor
• Female
• Free Radical Scavengers (chemistry)
• Humans
• Mice
• Mice, Inbred ICR
• Pancreatic Neoplasms
• Papilloma (prevention & control)
• Peroxynitrous Acid (chemistry)
• Skin Neoplasms (chemically induced, prevention & control)
• Tyrosine (analogs & derivatives, antagonists & inhibitors, chemistry)
• Xanthophylls (chemistry)