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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MDPI AG
2021-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/21/6626 |
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| 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 |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-03-10T05:56:14Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T05:56:14Z |
| publishDate | 2021-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-d6a60223e8ac4f4088c1be311c3b37442023-11-22T21:24:07ZengMDPI AGMolecules1420-30492021-11-012621662610.3390/molecules26216626Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from <i>Garcinia picrorhiza</i>Edwin R. Sukandar0Sutin Kaennakam1Pia Raab2Xuehong Nöst3Kitiya Rassamee4Rudolf Bauer5Pongpun Siripong6Taslim Ersam7Santi Tip-pyang8Warinthorn Chavasiri9Center of Excellence in Natural Products Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, ThailandDepartment of Agro-Industrial, Food, and Environmental Technology, Faculty of Applied Science, King Mongkut’s University of Technology North Bangkok (KMUTNB), Bangkok 10800, ThailandDepartment of Pharmacognosy, Institute of Pharmaceutical Sciences, University of Graz, Beethovenstraβe 8, 8010 Graz, AustriaDepartment of Pharmacognosy, Institute of Pharmaceutical Sciences, University of Graz, Beethovenstraβe 8, 8010 Graz, AustriaNatural Products Research Section, Research Division, National Cancer Institute, Bangkok 10400, ThailandDepartment of Pharmacognosy, Institute of Pharmaceutical Sciences, University of Graz, Beethovenstraβe 8, 8010 Graz, AustriaNatural Products Research Section, Research Division, National Cancer Institute, Bangkok 10400, ThailandNatural Products and Synthesis Chemistry Research Laboratory, Department of Chemistry, Faculty of Science and Data Analytics, Institut Teknologi Sepuluh Nopember, Kampus ITS-Sukolilo, Surabaya 60111, IndonesiaCenter of Excellence in Natural Products Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, ThailandCenter of Excellence in Natural Products Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand<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.https://www.mdpi.com/1420-3049/26/21/6626xanthoneisocoumarinClusiaceae<i>Garcinia picrorhiza</i>cytotoxicanti-inflammatory |
| spellingShingle | 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> Molecules xanthone isocoumarin Clusiaceae <i>Garcinia picrorhiza</i> cytotoxic anti-inflammatory |
| title | 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_short | 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 |
| topic | xanthone isocoumarin Clusiaceae <i>Garcinia picrorhiza</i> cytotoxic anti-inflammatory |
| url | https://www.mdpi.com/1420-3049/26/21/6626 |
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