Antioxidant and Antimutagenic Polyisoprenylated Benzophenones and Xanthones from Rheedia acuminata

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Abstract

Dichloromethane extract of the stem bark of Rheedia acuminata yielded three benzophenones with antioxidant activity, the new one named acuminophenone A (1), guttiferone K (2) and isoxanthochymol (3), along with the known xanthones formoxanthone C (4) and macluraxanthone (5). The structures were established through interpretation of their spectroscopic data, the stereochemistry of compounds (1) and (2) were resolved by experimental and computational experiments and their antioxidant activities were measured using the DPPH, ABTS and TEAC assays. The antioxidant results showed that metabolites 1, 4 and 5 had a better antioxidant activity than the reference compound quercetin. In addition, we evaluate the mutagenicity and antimutagenicity of the CH2Cl2 extract as well as of the free radical scavenger compounds 1, 4 and 5 by the AMES Salmonella/microsomal test. No mutagenicity was found in the CH2Cl2 extract using Salmonella typhimurium strains TA98, TA100, TA102, TA1537 and TA1538, with or without S9 metabolic activation. The pure compounds neither showed mutagenicity in TA 102 strain and the most important result was the strong reduction of mutagenic effect induced by hydrogen peroxide in S. typhimurium TA 102, with or without S9, showed by the compounds 1 (more than 93%) and 4 (more than 88%) at 0.02 mu g/plate.

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Subject classification (UKÄ) – MANDATORY

  • Biochemistry and Molecular Biology
  • Organic Chemistry

Keywords

  • Rheedia acuminata, polyisoprenylated benzophenones, prenylated, xanthones, acuminophenone A, guttiferone K, isoxanthochymol, formoxanthone C, macluraxanthone, antioxidant capacity, mutagenicity, antimutagenicity
Original languageEnglish
Pages (from-to)1269-1274
JournalNatural Product Communications
Volume6
Issue number9
Publication statusPublished - 2011
Publication categoryResearch
Peer-reviewedYes

Bibliographic note

The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240), Pure and Applied Biochemistry (LTH) (011001005)