title: Long-chain N-vanillyl-acylamides from Capsicum oleoresin.
abstract: N-Vanillyl-acylamides (NVAs) naturally occur as capsaicinoids in Capsicum plants. NVAs with a longer chain acyl moiety (LCNVAs) have been developed as attractive tools for medicinal usage because of their capsaicin-like bioactive and physiological properties, without harmful irritancy. In this study, we isolated four LCNVAs from Capsicum oleoresin. Their structures were determined to be N-vanillyl-hexadecanamide (palvanil, 2), N-vanillyl-octadecanamide (stevanil, 3), N-vanillyl-9E-octadecenamide (olvanil, 4), and N-vanillyl-9E,12E-octadecadienamide (livanil, 5) by spectroscopic analysis and gas chromatography-mass spectrometry analysis of their methanolysis products. Furthermore, the existence of two LCNVAs in oleoresin, N-vanillyl-tetradecanamide (myrvanil, 1) and N-vanillyl-9E,12E,15E-octadecatrienamide (linvanil, 6), was suggested. The contents of these LCNVAs and the major capsaicinoids-capsaicin and dihydrocapsaicin-in three Capsicum oleoresins and the fresh fruits of two hot peppers were measured by a liquid chromatography-tandem mass spectrometry system. The content ratios of the total LCNVAs, except for myrvanil, versus the capsaicin in the oleoresins (0.1-41%) was significantly larger than that in fresh fruits (<0.01%). The composition of these LCNVAs in each oleoresin was similar to that of fatty acids in the oil fraction of each oleoresin. We observed no relationship between the composition of these LCNVAs in the fresh fruits.
authors.affiliation: School of Food and Nutritional Sciences and Global COE Program, University of Shizuoka, Suruga-ku, Shizuoka, Japan.
authors.forename: Kenji
authors.initials: K
authors.lastname: Kobata
authors.forename: Kazumi
authors.initials: K
authors.lastname: Saito
authors.forename: Hitomi
authors.initials: H
authors.lastname: Tate
authors.forename: Aki
authors.initials: A
authors.lastname: Nashimoto
authors.forename: Hiromi
authors.initials: H
authors.lastname: Okuda
authors.forename: Ikue
authors.initials: I
authors.lastname: Takemura
authors.forename: Ken
authors.initials: K
authors.lastname: Miyakawa
authors.forename: Masayoshi
authors.initials: M
authors.lastname: Takahashi
authors.forename: Kazuo
authors.initials: K
authors.lastname: Iwai
authors.forename: Tatsuo
authors.initials: T
authors.lastname: Watanabe
mesh_terms: D000178:Acrylamides / Q000737:chemistry* / Q000302:isolation & purification; D001547:Benzaldehydes / Q000737:chemistry* / Q000302:isolation & purification; D002212:Capsicum / Q000737:chemistry*; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D000178:Acrylamides; D001547:Benzaldehydes; D010936:Plant Extracts; C100058:vanillin