In vitro stability and in vivo anti-inflammatory efficacy of synthetic jasmonates

Hung The Dang; Yoon Mi Lee; Gyeoung Jin Kang; Eun Sook Yoo; Jongki Hong; Sun Mee Lee; Sang Kook Lee; Yuna Pyee; Hwa Jin Chung; Hyung Ryong Moon; Hyung Sik Kim; Jee H. Jung

doi:10.1016/j.bmc.2012.04.052

In vitro stability and in vivo anti-inflammatory efficacy of synthetic jasmonates

Hung The Dang, Yoon Mi Lee, Gyeoung Jin Kang, Eun Sook Yoo, Jongki Hong, Sun Mee Lee, Sang Kook Lee, Yuna Pyee, Hwa Jin Chung, Hyung Ryong Moon, Hyung Sik Kim, Jee H. Jung

Medicine - Cardiology Division

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

A chlorinated methyl jasmonate analog (J7) was elaborated as an in vitro anti-inflammatory lead. However, its in vitro efficacy profile was not reproduced in a subsequent in vivo evaluation, presumably due to its rapid enzymatic hydrolysis in a biological system. In an attempt to improve the metabolic stability of the lead J7 by replacement of its labile methyl ester with reasonable ester groups, several analogs resistant to enzymatic hydrolysis were synthesized. In vivo evaluation of the stability-improved analogs showed that these compounds displayed higher efficacy than the lead J7, suggesting that these new jasmonate analogs may serve as potential anti-inflammatory leads.

Original language	English (US)
Pages (from-to)	4109-4116
Number of pages	8
Journal	Bioorganic and Medicinal Chemistry
Volume	20
Issue number	13
DOIs	https://doi.org/10.1016/j.bmc.2012.04.052
State	Published - Jul 1 2012

Bibliographical note

Funding Information:
This study was financially supported by a Grant from the National Research Foundation of Korea (No. 20090083538 ) and a Grant from the Marine Biotechnology Program funded by Ministry of Land, Transport, and Maritime Affairs, Korea.

Keywords

Anti-inflammatory activity
Metabolic stability
Methyl jasmonate analogs

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title = "In vitro stability and in vivo anti-inflammatory efficacy of synthetic jasmonates",

abstract = "A chlorinated methyl jasmonate analog (J7) was elaborated as an in vitro anti-inflammatory lead. However, its in vitro efficacy profile was not reproduced in a subsequent in vivo evaluation, presumably due to its rapid enzymatic hydrolysis in a biological system. In an attempt to improve the metabolic stability of the lead J7 by replacement of its labile methyl ester with reasonable ester groups, several analogs resistant to enzymatic hydrolysis were synthesized. In vivo evaluation of the stability-improved analogs showed that these compounds displayed higher efficacy than the lead J7, suggesting that these new jasmonate analogs may serve as potential anti-inflammatory leads.",

keywords = "Anti-inflammatory activity, Metabolic stability, Methyl jasmonate analogs",

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AU - Yoo, Eun Sook

AU - Hong, Jongki

AU - Lee, Sun Mee

AU - Lee, Sang Kook

AU - Pyee, Yuna

AU - Chung, Hwa Jin

AU - Moon, Hyung Ryong

AU - Kim, Hyung Sik

AU - Jung, Jee H.

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N2 - A chlorinated methyl jasmonate analog (J7) was elaborated as an in vitro anti-inflammatory lead. However, its in vitro efficacy profile was not reproduced in a subsequent in vivo evaluation, presumably due to its rapid enzymatic hydrolysis in a biological system. In an attempt to improve the metabolic stability of the lead J7 by replacement of its labile methyl ester with reasonable ester groups, several analogs resistant to enzymatic hydrolysis were synthesized. In vivo evaluation of the stability-improved analogs showed that these compounds displayed higher efficacy than the lead J7, suggesting that these new jasmonate analogs may serve as potential anti-inflammatory leads.

AB - A chlorinated methyl jasmonate analog (J7) was elaborated as an in vitro anti-inflammatory lead. However, its in vitro efficacy profile was not reproduced in a subsequent in vivo evaluation, presumably due to its rapid enzymatic hydrolysis in a biological system. In an attempt to improve the metabolic stability of the lead J7 by replacement of its labile methyl ester with reasonable ester groups, several analogs resistant to enzymatic hydrolysis were synthesized. In vivo evaluation of the stability-improved analogs showed that these compounds displayed higher efficacy than the lead J7, suggesting that these new jasmonate analogs may serve as potential anti-inflammatory leads.

KW - Anti-inflammatory activity

KW - Metabolic stability

KW - Methyl jasmonate analogs

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In vitro stability and in vivo anti-inflammatory efficacy of synthetic jasmonates

Abstract

Bibliographical note

Keywords

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