Picrorhizones A-H, Polyprenylated Benzoylphloroglucinols from the Stem Bark of Garcinia picrorhiza

Edwin R. Sukandar, Sutin Kaennakam, Thammarat Aree, Xuehong Nöst, Kitiya Rassamee, Rudolf Bauer, Pongpun Siripong, Taslim Ersam, Santi Tip-Pyang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

Eight new polyprenylated benzoylphloroglucinol derivatives (1-8) and four known analogues (9-12) were isolated from the stem bark of Garcinia picrorhiza. Their structures were determined by spectroscopic data analysis (1D and 2D NMR and HRESIMS), and the absolute configurations were established by single-crystal X-ray diffraction combined with experimental and calculated ECD data. The new metabolites represent rare examples of benzoylphloroglucinols bearing a cyclobutyl-containing side chain. The isolated compounds were evaluated for their cytotoxic properties against five types of human cancer cells (KB, HeLa S3, MCF-7, Hep G2, and HT-29 cells) and their inhibitory activities against COX-1 and COX-2 enzymes. The cytotoxicity results showed that compound 6 was active against KB, HeLa S3, MCF-7, and Hep G2 cancer cells, with IC50 values ranging from 5.9 to 9.4 μM. Among the compounds tested for cyclooxygenase inhibition, compound 8 possessed the highest inhibitory effect toward COX-1 (35.2 ± 9.6% inhibition at 20 μM).

Original languageEnglish
Pages (from-to)2102-2111
Number of pages10
JournalJournal of Natural Products
Volume83
Issue number7
DOIs
Publication statusPublished - 24 Jul 2020

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