Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from <i>Garcinia picrorhiza</i>

<i>Garcinia picrorhiza</i>, a woody plant native to Sulawesi and Maluku Islands, Indonesia, has been traditionally used as a wound healing ointment. In our continuous search for bioactive compounds from this plant, 15 phenolic compounds were isolated from its stem bark, including a previ...

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Autores principales:	Edwin R. Sukandar, Sutin Kaennakam, Pia Raab, Xuehong Nöst, Kitiya Rassamee, Rudolf Bauer, Pongpun Siripong, Taslim Ersam, Santi Tip-pyang, Warinthorn Chavasiri
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	xanthone isocoumarin Clusiaceae <i>Garcinia picrorhiza</i> cytotoxic anti-inflammatory Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/d6a60223e8ac4f4088c1be311c3b3744
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spelling	oai:doaj.org-article:d6a60223e8ac4f4088c1be311c3b37442021-11-11T18:35:52ZCytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from <i>Garcinia picrorhiza</i>10.3390/molecules262166261420-3049https://doaj.org/article/d6a60223e8ac4f4088c1be311c3b37442021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6626https://doaj.org/toc/1420-3049<i>Garcinia picrorhiza</i>, a woody plant native to Sulawesi and Maluku Islands, Indonesia, has been traditionally used as a wound healing ointment. In our continuous search for bioactive compounds from this plant, 15 phenolic compounds were isolated from its stem bark, including a previously undescribed dihydroisocoumarin, 2′-hydroxyannulatomarin, and two undescribed furanoxanthones, gerontoxanthone C hydrate and 3′-hydroxycalothorexanthone. The structures of the new metabolites were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR and HRESIMS. Gerontoxanthone C hydrate possessed cytotoxicity against four cancer cells (KB, HeLa S3, MCF-7, and Hep G2) with IC<sub>50</sub> values ranging from 5.6 to 7.5 µM. Investigation on the anti-inflammatory activities showed that 3′-hydroxycalothorexanthone inhibited NO production in RAW 264.7 and BV-2 cell lines with IC<sub>50</sub> values of 16.4 and 13.8 µM, respectively, whereas only (−)-annulatomarin possessed inhibition activity on COX-2 enzyme over 10% at 20 µM. This work describes the presence of 3,4-dihydroisocoumarin structures with a phenyl ring substituent at C-3, which are reported the first time in genus <i>Garcinia</i>. These findings also suggest the potential of furanxanthone derivatives as cytotoxic and anti-inflammatory agents for further pharmacological studies.Edwin R. SukandarSutin KaennakamPia RaabXuehong NöstKitiya RassameeRudolf BauerPongpun SiripongTaslim ErsamSanti Tip-pyangWarinthorn ChavasiriMDPI AGarticlexanthoneisocoumarinClusiaceae<i>Garcinia picrorhiza</i>cytotoxicanti-inflammatoryOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6626, p 6626 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	xanthone isocoumarin Clusiaceae <i>Garcinia picrorhiza</i> cytotoxic anti-inflammatory Organic chemistry QD241-441
spellingShingle	xanthone isocoumarin Clusiaceae <i>Garcinia picrorhiza</i> cytotoxic anti-inflammatory Organic chemistry QD241-441 Edwin R. Sukandar Sutin Kaennakam Pia Raab Xuehong Nöst Kitiya Rassamee Rudolf Bauer Pongpun Siripong Taslim Ersam Santi Tip-pyang Warinthorn Chavasiri Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from <i>Garcinia picrorhiza</i>
description	<i>Garcinia picrorhiza</i>, a woody plant native to Sulawesi and Maluku Islands, Indonesia, has been traditionally used as a wound healing ointment. In our continuous search for bioactive compounds from this plant, 15 phenolic compounds were isolated from its stem bark, including a previously undescribed dihydroisocoumarin, 2′-hydroxyannulatomarin, and two undescribed furanoxanthones, gerontoxanthone C hydrate and 3′-hydroxycalothorexanthone. The structures of the new metabolites were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR and HRESIMS. Gerontoxanthone C hydrate possessed cytotoxicity against four cancer cells (KB, HeLa S3, MCF-7, and Hep G2) with IC<sub>50</sub> values ranging from 5.6 to 7.5 µM. Investigation on the anti-inflammatory activities showed that 3′-hydroxycalothorexanthone inhibited NO production in RAW 264.7 and BV-2 cell lines with IC<sub>50</sub> values of 16.4 and 13.8 µM, respectively, whereas only (−)-annulatomarin possessed inhibition activity on COX-2 enzyme over 10% at 20 µM. This work describes the presence of 3,4-dihydroisocoumarin structures with a phenyl ring substituent at C-3, which are reported the first time in genus <i>Garcinia</i>. These findings also suggest the potential of furanxanthone derivatives as cytotoxic and anti-inflammatory agents for further pharmacological studies.
format	article
author	Edwin R. Sukandar Sutin Kaennakam Pia Raab Xuehong Nöst Kitiya Rassamee Rudolf Bauer Pongpun Siripong Taslim Ersam Santi Tip-pyang Warinthorn Chavasiri
author_facet	Edwin R. Sukandar Sutin Kaennakam Pia Raab Xuehong Nöst Kitiya Rassamee Rudolf Bauer Pongpun Siripong Taslim Ersam Santi Tip-pyang Warinthorn Chavasiri
author_sort	Edwin R. Sukandar
title	Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from <i>Garcinia picrorhiza</i>
title_short	Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from <i>Garcinia picrorhiza</i>
title_full	Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from <i>Garcinia picrorhiza</i>
title_fullStr	Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from <i>Garcinia picrorhiza</i>
title_full_unstemmed	Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from <i>Garcinia picrorhiza</i>
title_sort	cytotoxic and anti-inflammatory activities of dihydroisocoumarin and xanthone derivatives from <i>garcinia picrorhiza</i>
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/d6a60223e8ac4f4088c1be311c3b3744
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Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from <i>Garcinia picrorhiza</i>

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