Isolation of coniferyl esters from Capsicum baccatum L., and their enzymatic preparation and agonist activity for TRPV1.
Coniferyl esters--capsiconiate and dihydrocapsiconiate--were isolated from the fruits of the pepper, Capsicum baccatum L. var. praetermissum. Their structures were determined by spectroscopic methods to be coniferyl (E)-8-methyl-6-nonenoate (capsiconiate) and coniferyl 8-methylnonanoate (dihydrocapsiconiate). This finding was further confirmed by the lipase-catalyzed condensation of coniferyl alcohol with its corresponding fatty acid derivative. The agonist activity of the esters for transient receptor potential vanilloid 1 (TRPV1) was evaluated by conducting an analysis of the intracellular calcium concentrations in TRPV1-expressing HEK293 cells. The EC50 values of capsiconiate and dihydrocapsiconiate were 3.2 and 4.2 microM, respectively.
Kobata
Kenji
K
School of Food and Nutritional Sciences and COE program in the 21st century, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
Tate
Hitomi
H
Iwasaki
Yusaku
Y
Tanaka
Yoshiyuki
Y
Ohtsu
Keigo
K
Yazawa
Susumu
S
Watanabe
Tatsuo
T
D002118:Calcium / Q000032:analysis; D002211:Capsaicin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002212:Capsicum / Q000737:chemistry* / Q000254:growth & development; D002384:Catalysis; D002460:Cell Line; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical; D006801:Humans; D008049:Lipase / Q000737:chemistry*; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry; D050916:TRPV Cation Channels / Q000819:agonists* / Q000096:biosynthesis
D010636:Phenols; D050916:TRPV Cation Channels; C494482:TRPV1 protein, human; C530524:coniferyl (E)-8-methyl-6-nonenoate; C530525:coniferyl 8-methylnonanoate; C010559:coniferyl alcohol; D008049:Lipase; D002211:Capsaicin; D002118:Calcium