2. Academic Validation
  3. Picrorhizones A-H, Polyprenylated Benzoylphloroglucinols from the Stem Bark of Garcinia picrorhiza

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

  • J Nat Prod. 2020 Jul 24;83(7):2102-2111. doi: 10.1021/acs.jnatprod.9b01106.
Edwin R Sukandar 1,  Sutin Kaennakam 1 2,  Thammarat Aree 1,  Xuehong Nöst 3,  Kitiya Rassamee 4,  Rudolf Bauer 3,  Pongpun Siripong 4,  Taslim Ersam 5,  Santi Tip-Pyang 1
Affiliations

Affiliations

  • 1 Center of Excellence in Natural Products Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.
  • 2 Department of Agro-Industrial, Food, and Environmental Technology, Faculty of Applied Science, King Mongkut's University of Technology North Bangkok (KMUTNB), Bangkok 10800, Thailand.
  • 3 Institute of Pharmaceutical Sciences, Department of Pharmacognosy, University of Graz, Universitätsplatz 4/1, 8010 Graz, Austria.
  • 4 Natural Products Research Section, Research Division, National Cancer Institute, Bangkok 10400, Thailand.
  • 5 Natural Products and Synthesis Chemistry Research Laboratory, Department of Chemistry, Faculty of Science, Institut Teknologi Sepuluh Nopember, Kampus ITS-Sukolilo, Surabaya 60111, Indonesia.
PMID: 32627543 DOI: 10.1021/acs.jnatprod.9b01106
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).

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