Abstract
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.
Highlights
The genus Garcinia, one of the largest genera to the family Clusiaceae, is widespread in tropical rain forests with the center points are in Southeast Asia and Madagascar
The CH2Cl2-soluble fraction from the stem bark of Garcinia picrorhiza was subjected to a combination of chromatographic methods using silica gel, Sephadex LH-20, and chromatotron to give 15 compounds, including a new dihydroisocoumarin derivative, 2 -hydroxyannulatomarin (3), and two new furanoxanthones, gerontoxanthone C hydrate (4) and 3 -hydroxycalothorexanthone (5)
The 1D NMR data of 3 were found to be similar to those of annulatomarin, a 3,4-dihydroisocoumarin derivative isolated from an herbaceous plant, Hypericum annulatum [14]
Summary
The genus Garcinia, one of the largest genera to the family Clusiaceae, is widespread in tropical rain forests with the center points are in Southeast Asia and Madagascar. This genus is pantropical and comprises a high level of species diversity with more than 250 species of evergreen, lactiferous, dioecious, and small shrubs to medium-sized trees [1,2]. Phytochemical analysis of genus Garcinia resulted in the isolation of structurally diverse secondary metabolites, especially phenolic compounds, such as xanthones, polyprenylated benzoylphloroglucinols, biphenyls, depsidones, and biflavonoids and many of which gained great attention because of their biological and pharmacological activities [3]. We report the isolation, structural elucidation, and cytotoxic and anti-inflammatory effects of the phenolic compounds from the stem bark of G. picrorhiza
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