Concise synthesis of catechin metabolites 5-(30,40-dihydroxyphenyl)-γ-valerolactones (dhpv) in optically pure form and their stereochemical effects on skin wrinkle-reducing activities

Joonseong Hur; A. Ram Kim; Hyun Su Kim; Changjin Lim; Taewoo Kim; Tae Aug Kim; Jaehoon Sim; Young Ger Suh

doi:10.3390/molecules25081970

Concise synthesis of catechin metabolites 5-(30,40-dihydroxyphenyl)-γ-valerolactones (dhpv) in optically pure form and their stereochemical effects on skin wrinkle-reducing activities

Joonseong Hur
, A. Ram Kim
, Hyun Su Kim
, Changjin Lim
, Taewoo Kim
, Tae Aug Kim
, Jaehoon Sim^*
, Young Ger Suh

^*Corresponding author for this work

Department of Pharmacy

Korea Institute of Science and Technology
CHA University
Chungnam National University

Research output: Contribution to journal › Journal article › peer-review

9 Scopus citations

Abstract

A concise and scalable synthetic route for optically pure (4S) and (4R)-5-(3⁰,4⁰-dihydroxyphenyl)-γ-valerolactones (DHPVs), catechin metabolites, has been developed via the efficient construction of a γ-valerolactone moiety from hexenol. Noticeably, the different skin wrinkle-reducing activities of each metabolite were revealed via our unique syntheses of DHPVs in an enantiomerically pure form.

Original language	English
Article number	1970
Journal	Molecules
Volume	25
Issue number	8
DOIs	https://doi.org/10.3390/molecules25081970
State	Published - 2020.04

Keywords

Catechin metabolite
Concise synthesis
Skin wrinkle-reducing activity
γ-valerolactone

Quacquarelli Symonds(QS) Subject Topics

Medicine
Engineering - Petroleum
Pharmacy & Pharmacology
Chemistry

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10.3390/molecules25081970

Cite this

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title = "Concise synthesis of catechin metabolites 5-(30,40-dihydroxyphenyl)-γ-valerolactones (dhpv) in optically pure form and their stereochemical effects on skin wrinkle-reducing activities",

abstract = "A concise and scalable synthetic route for optically pure (4S) and (4R)-5-(30,40-dihydroxyphenyl)-γ-valerolactones (DHPVs), catechin metabolites, has been developed via the efficient construction of a γ-valerolactone moiety from hexenol. Noticeably, the different skin wrinkle-reducing activities of each metabolite were revealed via our unique syntheses of DHPVs in an enantiomerically pure form.",

keywords = "Catechin metabolite, Concise synthesis, Skin wrinkle-reducing activity, γ-valerolactone",

author = "Joonseong Hur and Kim, \{A. Ram\} and Kim, \{Hyun Su\} and Changjin Lim and Taewoo Kim and Kim, \{Tae Aug\} and Jaehoon Sim and Suh, \{Young Ger\}",

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AU - Hur, Joonseong

AU - Kim, A. Ram

AU - Kim, Hyun Su

AU - Lim, Changjin

AU - Kim, Taewoo

AU - Kim, Tae Aug

AU - Sim, Jaehoon

AU - Suh, Young Ger

N1 - Publisher Copyright: © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

PY - 2020/4

Y1 - 2020/4

N2 - A concise and scalable synthetic route for optically pure (4S) and (4R)-5-(30,40-dihydroxyphenyl)-γ-valerolactones (DHPVs), catechin metabolites, has been developed via the efficient construction of a γ-valerolactone moiety from hexenol. Noticeably, the different skin wrinkle-reducing activities of each metabolite were revealed via our unique syntheses of DHPVs in an enantiomerically pure form.

AB - A concise and scalable synthetic route for optically pure (4S) and (4R)-5-(30,40-dihydroxyphenyl)-γ-valerolactones (DHPVs), catechin metabolites, has been developed via the efficient construction of a γ-valerolactone moiety from hexenol. Noticeably, the different skin wrinkle-reducing activities of each metabolite were revealed via our unique syntheses of DHPVs in an enantiomerically pure form.

KW - Catechin metabolite

KW - Concise synthesis

KW - Skin wrinkle-reducing activity

KW - γ-valerolactone

UR - https://www.scopus.com/pages/publications/85083775504

U2 - 10.3390/molecules25081970

DO - 10.3390/molecules25081970

M3 - Journal article

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AN - SCOPUS:85083775504

SN - 1420-3049

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JO - Molecules

JF - Molecules

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ER -

Concise synthesis of catechin metabolites 5-(30,40-dihydroxyphenyl)-γ-valerolactones (dhpv) in optically pure form and their stereochemical effects on skin wrinkle-reducing activities

Abstract

Keywords

Quacquarelli Symonds(QS) Subject Topics

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