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Planta Med 2023; 89(05): 508-515
DOI: 10.1055/a-1841-0745
Biological and Pharmacological Activity
Original Papers

Cytotoxic Polyprenylated Benzoylphloroglucinol Derivatives from the Branches of Garcinia schomburgkiana

Sutin Kaennakam
1   Department of Agro-Industrial, Food, and Environmental Technology, Faculty of Applied Science, King Mongkutʼs University of Technology North Bangkok (KMUTNB), Bangkok, Thailand
,
Edwin Risky Sukandar
2   Center of Excellence in Natural Products Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand
,
Kitiya Rassamee
3   Natural Products Research Section, Research Division, National Cancer Institute, Bangkok, Thailand
,
Pongpun Siripong
3   Natural Products Research Section, Research Division, National Cancer Institute, Bangkok, Thailand
,
Santi Tip-pyang › Author Affiliations
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Abstract

Five undescribed polyprenylated benzoylphloroglucinol derivatives (1 – 5), named garschomcinols A – E, and five known analogues (6 – 10) were isolated from the branches of Garcinia schomburgkiana. Their structures were determined on the basis of 1D and 2D NMR and HRESIMS analyses. The absolute configuration of the bicyclo [3.3.1]nonane core structure of the polyprenylated benzoylphloroglucinols was assigned by comparison of its experimental electronic circular dichroism data with that of related compounds. All isolated compounds were evaluated for their cytotoxicity in vitro against five cancer cell lines. Compound 6 showed potent cytotoxicity against five cancer cell lines including KB, HeLa S3, HT-29, MCF-7, and Hep G2 with IC50 values in the range of 5.05 – 7.03 µM.

Key words

Garcinia schomburgkiana - Clusiaceae - polyprenylated benzoylphloroglucinols - garschomcinols A – E - cytotoxicity

Supporting Information

    NMR, HRESIMS, and ECD spectra of compounds 1 – 5 and concentration-response curves of 1 – 3, 6 – 10, and doxorubicin are available as Supporting Information.

  • Supporting Information


Publication History

Received: 16 January 2022

Accepted after revision: 02 May 2022

Accepted Manuscript online:
02 May 2022

Article published online:
28 July 2022

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