Bioactive Dimeric Abietanoid Peroxides from the Bark of Cryptomeria japonica

Three new dimeric abietane-type diterpenoids, abieta-6,8,11,13-tetraen-12-yl 12-hydroxyabieta-8,11,13-trien-7α-yl peroxide (1), abieta-6,8,11,13-tetraen-12-yl 12-hydroxyabieta-8,11,13-trien-7β-yl peroxide (2), and 12-hydroxyabieta-8,11,13-trien...

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Main Authors:	Chi-I Chang, Cheng-Chi Chen, Chiy-Rong Chen, Ming-Der Wu, Ming-Jen Cheng, Ping-Jyun Sung, Yueh-Hsiung Kuo
Format:	Article
Language:	English
Published:	MDPI AG 2019-06-01
Series:	Molecules
Subjects:	Cupressaceae <i>Cryptomeria japonica</i> dimeric abietane diterpenoid
Online Access:	https://www.mdpi.com/1420-3049/24/11/2178

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spelling	doaj-5d2bdb0aac684455b97805f300b238b82020-11-25T00:12:29ZengMDPI AGMolecules1420-30492019-06-012411217810.3390/molecules24112178molecules24112178Bioactive Dimeric Abietanoid Peroxides from the Bark of <i>Cryptomeria japonica</i>Chi-I Chang0Cheng-Chi Chen1Chiy-Rong Chen2Ming-Der Wu3Ming-Jen Cheng4Ping-Jyun Sung5Yueh-Hsiung Kuo6Department of Biological Science and Technology, National Pingtung University of Science and Technology, Pingtung 912, TaiwanDepartment of Chemistry, National Taiwan University, Taipei 106, TaiwanDepartment of Life Science, National Taitung University, Taitung 950, TaiwanBioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, TaiwanBioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, TaiwanNational Museum of Marine Biology and Aquarium, Pingtung 944, TaiwanDepartment of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, College of Pharmacy, China Medical University, Taichung 404, TaiwanThree new dimeric abietane-type diterpenoids, abieta-6,8,11,13-tetraen-12-yl 12-hydroxyabieta-8,11,13-trien-7α-yl peroxide (<b>1</b>), abieta-6,8,11,13-tetraen-12-yl 12-hydroxyabieta-8,11,13-trien-7β-yl peroxide (<b>2</b>), and 12-hydroxyabieta-8,11,13-trien-7β-yl 7-oxoabieta-5,8,11,13-tetraen-12-yl peroxide (<b>3</b>), together with four known abietane-type diterpenoids (<b>4</b>−<b>7</b>) were isolated from the methanol extract of the bark of <i>Cryptomeria japonica</i>. Their structures were elucidated on the basis of spectroscopic analysis and comparison of NMR data with those of known analogues. At a concentration of 50 μM, compounds <b>1</b>, <b>2</b>, and <b>3</b> showed 26.2%, 23.6%, and 35.7% inhibition towards xanthine oxidase enzyme, respectively. In addition, compound <b>3</b> also showed 24.9% inhibition toward angiotensin-converting enzyme (ACE).https://www.mdpi.com/1420-3049/24/11/2178Cupressaceae<i>Cryptomeria japonica</i>dimeric abietanediterpenoid
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Chi-I Chang Cheng-Chi Chen Chiy-Rong Chen Ming-Der Wu Ming-Jen Cheng Ping-Jyun Sung Yueh-Hsiung Kuo
spellingShingle	Chi-I Chang Cheng-Chi Chen Chiy-Rong Chen Ming-Der Wu Ming-Jen Cheng Ping-Jyun Sung Yueh-Hsiung Kuo Bioactive Dimeric Abietanoid Peroxides from the Bark of <i>Cryptomeria japonica</i> Molecules Cupressaceae <i>Cryptomeria japonica</i> dimeric abietane diterpenoid
author_facet	Chi-I Chang Cheng-Chi Chen Chiy-Rong Chen Ming-Der Wu Ming-Jen Cheng Ping-Jyun Sung Yueh-Hsiung Kuo
author_sort	Chi-I Chang
title	Bioactive Dimeric Abietanoid Peroxides from the Bark of <i>Cryptomeria japonica</i>
title_short	Bioactive Dimeric Abietanoid Peroxides from the Bark of <i>Cryptomeria japonica</i>
title_full	Bioactive Dimeric Abietanoid Peroxides from the Bark of <i>Cryptomeria japonica</i>
title_fullStr	Bioactive Dimeric Abietanoid Peroxides from the Bark of <i>Cryptomeria japonica</i>
title_full_unstemmed	Bioactive Dimeric Abietanoid Peroxides from the Bark of <i>Cryptomeria japonica</i>
title_sort	bioactive dimeric abietanoid peroxides from the bark of <i>cryptomeria japonica</i>
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2019-06-01
description	Three new dimeric abietane-type diterpenoids, abieta-6,8,11,13-tetraen-12-yl 12-hydroxyabieta-8,11,13-trien-7α-yl peroxide (<b>1</b>), abieta-6,8,11,13-tetraen-12-yl 12-hydroxyabieta-8,11,13-trien-7β-yl peroxide (<b>2</b>), and 12-hydroxyabieta-8,11,13-trien-7β-yl 7-oxoabieta-5,8,11,13-tetraen-12-yl peroxide (<b>3</b>), together with four known abietane-type diterpenoids (<b>4</b>−<b>7</b>) were isolated from the methanol extract of the bark of <i>Cryptomeria japonica</i>. Their structures were elucidated on the basis of spectroscopic analysis and comparison of NMR data with those of known analogues. At a concentration of 50 μM, compounds <b>1</b>, <b>2</b>, and <b>3</b> showed 26.2%, 23.6%, and 35.7% inhibition towards xanthine oxidase enzyme, respectively. In addition, compound <b>3</b> also showed 24.9% inhibition toward angiotensin-converting enzyme (ACE).
topic	Cupressaceae <i>Cryptomeria japonica</i> dimeric abietane diterpenoid
url	https://www.mdpi.com/1420-3049/24/11/2178
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Bioactive Dimeric Abietanoid Peroxides from the Bark of <i>Cryptomeria japonica</i>

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