Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from <i>Garcinia picrorhiza</i>
Edwin R. Sukandar,
Sutin Kaennakam,
Pia Raab,
Xuehong Nöst,
Kitiya Rassamee,
Rudolf Bauer,
Pongpun Siripong,
Taslim Ersam,
Santi Tip-pyang,
Warinthorn Chavasiri
Affiliations
Edwin R. Sukandar
Center of Excellence in Natural Products Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
Sutin Kaennakam
Department of Agro-Industrial, Food, and Environmental Technology, Faculty of Applied Science, King Mongkut’s University of Technology North Bangkok (KMUTNB), Bangkok 10800, Thailand
Pia Raab
Department of Pharmacognosy, Institute of Pharmaceutical Sciences, University of Graz, Beethovenstraβe 8, 8010 Graz, Austria
Xuehong Nöst
Department of Pharmacognosy, Institute of Pharmaceutical Sciences, University of Graz, Beethovenstraβe 8, 8010 Graz, Austria
Kitiya Rassamee
Natural Products Research Section, Research Division, National Cancer Institute, Bangkok 10400, Thailand
Rudolf Bauer
Department of Pharmacognosy, Institute of Pharmaceutical Sciences, University of Graz, Beethovenstraβe 8, 8010 Graz, Austria
Pongpun Siripong
Natural Products Research Section, Research Division, National Cancer Institute, Bangkok 10400, Thailand
Taslim Ersam
Natural Products and Synthesis Chemistry Research Laboratory, Department of Chemistry, Faculty of Science and Data Analytics, Institut Teknologi Sepuluh Nopember, Kampus ITS-Sukolilo, Surabaya 60111, Indonesia
Santi Tip-pyang
Center of Excellence in Natural Products Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
Warinthorn Chavasiri
Center of Excellence in Natural Products Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
Garcinia picrorhiza, 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 IC50 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 IC50 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 Garcinia. These findings also suggest the potential of furanxanthone derivatives as cytotoxic and anti-inflammatory agents for further pharmacological studies.
