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

doi:10.1016/j.phytochem.2007.11.017

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 journal › Article › peer-review

19 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 language	English
Pages (from-to)	1179-1184
Number of pages	6
Journal	Phytochemistry
Volume	69
Issue number	5
DOIs	https://doi.org/10.1016/j.phytochem.2007.11.017
Publication status	Published - Mar 2008

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

Biochemistry
Molecular Biology
Plant Science
Horticulture

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10.1016/j.phytochem.2007.11.017

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

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.",

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

author = "Kenji Kobata and Hitomi Tate and Yusaku Iwasaki and Yoshiyuki Tanaka and Keigo Ohtsu and Susumu Yazawa and Tatsuo Watanabe",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research No. 18380023 by the Japan Society for the Promotion of Science.",

year = "2008",

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doi = "10.1016/j.phytochem.2007.11.017",

language = "English",

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AU - Kobata, Kenji

AU - Tate, Hitomi

AU - Iwasaki, Yusaku

AU - Tanaka, Yoshiyuki

AU - Ohtsu, Keigo

AU - Yazawa, Susumu

AU - Watanabe, Tatsuo

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research No. 18380023 by the Japan Society for the Promotion of Science.

PY - 2008/3

Y1 - 2008/3

N2 - 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.

AB - 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.

KW - Calcium influx

KW - Capsiconiate

KW - Capsicum baccatum L. var. praetermissum

KW - Coniferyl ester

KW - Dihydrocapsiconiate

KW - Lipase-catalyzed preparation

KW - Solanaceae

KW - Spectroscopic analysis

KW - Transient receptor potential vanilloid 1 (TRPV1)

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

Abstract

Keywords

ASJC Scopus subject areas

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