4.7 Article

Polycyclic Polyprenylated Xanthones from Symphonia globulifera: Isolation and Biomimetic Electrosynthesis

Journal

JOURNAL OF NATURAL PRODUCTS
Volume 78, Issue 8, Pages 2136-2140

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.5b00239

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Funding

  1. Universite Paris Descartes, Sorbonne Paris Cite

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Two regioisomeric polycydic xanthones, 3,16-oxyguttiferone A (2) and 1,16-oxyguttiferone A (3), which are polyprenylated acylphloroglucinol-derived analogues, were isolated from the seeds of Symphonia globulifera, together with their presumed o-dihydroxybenzoyl precursor, guttiferone A (1). Anodic oxidation of 1 into the corresponding o-quinone species proved to be an efficient biomimetic method to generate xanthones 2 and 3 in high overall yield and to confirm their structures. Both compounds displayed cytotoxicity against the HCT 116 colon carcinoma cell line with IC50 values of 8 and 3 mu M, respectively.

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