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Capsinoids
Capsinoids, which include capsiate, dihydrocapsiate, and nordihydrocapsiate, are substances naturally present in chili peppers. Although they are structurally similar to capsaicin, the substance that causes pungency in hot peppers, they largely lack that characteristic. Capsinoids have an estimated “hot taste threshold” which is about 1/1000 that of capsaicin. Capsinoids were not reported in the scientific literature until 1989,〔Yazawa S, et al., Content of capsiaicinoids and capsaicinoid-like substances in fruit of pepper (Capsicum annum L.) hybrids made with “CH-19 Sweet as a parent. J Jpn Soc Hortic Sci58:601-607, 1989.〕 when biologists first isolated them in a unique variety of chili peppers, CH-19 Sweet, which does not contain capsaicin. Capsinoids include capsiate, dihydrocapsiate and nordihydrocapsiate.〔Kobata, K., Todo, T., Yazawa, S., Iwi, K. and Watabe, T. (1998) Novel capsaicinoid-like substances, capsiate and dihydrocapsiate, from the fruits of a nonpungent cultivar, CH-19 sweet, of pepper (Capsicum annuum L.). Journal of Agriculture and Food Chemistry 46:1695-1697.〕〔Kobata, K., Sutoh, K., Todo, T., Yazawa, S., Iwai, K. and Watanabe, T. (1999) Nordihydrocapsiate , a new capsinoid from the fruits of a nonpungent pepper, Capsicum annuum. Journal of Natural Products. 62:335-336.〕〔Yazawa, S., Yoneda, H., Hosokawa, M., Fushiki, T. and Watanabe, T. (2004) Novel capsaicinoid like substances in the fruits of new non-pungent cultivar CH-19 sweet of pepper (Capsicum annuum). Capsicum and Eggplant Newsletter 23:17-20.〕
Many health effects have been ascribed to capsaicin and capsinoids, both anecdotally and through scientific study, including anticancer, anti-inflammatory, and analgesic activities, and weight management.〔Antonio Macho, Concepción Lucena, Rocio Sancho, Nives Daddario, Alberto Minassi, Eduardo Muñoz, Giovanni Appendino. "Non-pungent Capsaicinoids from Sweet Pepper Synthesis and Evaluation of the Chemopreventive and Anticancer Potential." Eur. J. Nutr. 42 (2003): 2-9.〕〔Rocío Sancho, Concepción Lucena, Antonio Macho, Marco A. Calzado, Magdalena Blanco-Molina, Alberto Minassi, Giovanni Appendino and Eduardo Muñoz. "Immunosuppressive Activity of Capsaicinoids: Capsiate Derived from Sweet Peppers Inhibits NF-kappaB Activation and is a Potent Anti-inflammatory Compound in Vivo." Eur. J. Immunol. 32 (2002): 1753-1763.〕〔He G.-J. et al., European Journal of Medicinal Chemistry 44: 3345-3349, 2009〕〔Kawabata F. et al., Biosci Biotechnol Biochem 70:2824-2835, 2006.〕〔Sheldon Handler Ph.D., M.D.; David Rorvik: PDR for Nutritional Supplements Second Edition. Thomas Reuters; 2008.〕
== Structure ==
Structural differences between capsaicin and members of the capsinoid family of compounds are illustrated below. Capsinoids have an ester bond in their structures as compared with the amide bond characteristic of capsaicin 〔〔
Structure of capsinoids, including capsiate, dihydrocapsiate, and nordihydrocapsiate.
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