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. 2021 Nov 1;26(21):6626.
doi: 10.3390/molecules26216626.

Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from Garcinia picrorhiza

Edwin R Sukandar  1 , Sutin Kaennakam  2 , Pia Raab  3 , Xuehong Nöst  3 , Kitiya Rassamee  4 , Rudolf Bauer  3 , Pongpun Siripong  4 , Taslim Ersam  5 , Santi Tip-Pyang  1 , Warinthorn Chavasiri  1
Affiliations

Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from Garcinia picrorhiza

Edwin R Sukandar et al. Molecules. .

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.

Keywords: Clusiaceae; Garcinia picrorhiza; anti-inflammatory; cytotoxic; isocoumarin; xanthone.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Isolated compounds (1‒15) from the stem bark of Garcinia picrorhiza.
Figure 2
Figure 2
Key COSY (blue line) and HMBC (red arrow) correlation of compounds 3‒5.
Figure 3
Figure 3
(a) NO production inhibitory effects and (b) cytotoxic properties of compounds 1‒8 at a final concentration of 50 µM in LPS-IFN-γ-induced RAW 264.7 macrophages and BV-2 microglial cells. L-NMMA was used as the positive control at 100 µM. The NO inhibition of control group (LPS-IFN-γ-induced cells with 1% DMSO) was set as 100% (n = 6).
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