Isolation of coniferyl esters from Capsicum baccatum L., and their enzymatic preparation and agonist activity for TRPV1

Kenji Kobata, Hitomi Tate, Yusaku Iwasaki, Yoshiyuki Tanaka, Keigo Ohtsu, Susumu Yazawa, Tatsuo Watanabe

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

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 μM, respectively.

Original languageEnglish
Pages (from-to)1179-1184
Number of pages6
JournalPhytochemistry
Volume69
Issue number5
DOIs
Publication statusPublished - Mar 2008
Externally publishedYes

Fingerprint

Capsicum baccatum
Capsicum
agonists
Esters
esters
coniferyl alcohol
receptors
pepper
fatty acids
calcium
fruits
HEK293 Cells
Fruits
Lipase
Condensation
Fruit
Fatty Acids
cells
Calcium
Derivatives

Keywords

  • Calcium influx
  • Capsiconiate
  • Capsicum baccatum L. var. praetermissum
  • Coniferyl ester
  • Dihydrocapsiconiate
  • Lipase-catalyzed preparation
  • Solanaceae
  • Spectroscopic analysis
  • Transient receptor potential vanilloid 1 (TRPV1)

ASJC Scopus subject areas

  • Plant Science
  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery

Cite this

Isolation of coniferyl esters from Capsicum baccatum L., and their enzymatic preparation and agonist activity for TRPV1. / Kobata, Kenji; Tate, Hitomi; Iwasaki, Yusaku; Tanaka, Yoshiyuki; Ohtsu, Keigo; Yazawa, Susumu; Watanabe, Tatsuo.

In: Phytochemistry, Vol. 69, No. 5, 03.2008, p. 1179-1184.

Research output: Contribution to journalArticle

Kobata, K, Tate, H, Iwasaki, Y, Tanaka, Y, Ohtsu, K, Yazawa, S & Watanabe, T 2008, 'Isolation of coniferyl esters from Capsicum baccatum L., and their enzymatic preparation and agonist activity for TRPV1', Phytochemistry, vol. 69, no. 5, pp. 1179-1184. https://doi.org/10.1016/j.phytochem.2007.11.017
Kobata, Kenji ; Tate, Hitomi ; Iwasaki, Yusaku ; Tanaka, Yoshiyuki ; Ohtsu, Keigo ; Yazawa, Susumu ; Watanabe, Tatsuo. / Isolation of coniferyl esters from Capsicum baccatum L., and their enzymatic preparation and agonist activity for TRPV1. In: Phytochemistry. 2008 ; Vol. 69, No. 5. pp. 1179-1184.
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