Volume 21, Issue 12 e202401450
Research Article

Three New Polyprenylated Benzophenone Derivatives Isolated from Clusia burle-marxii

Maria do Carmo C. Silva

Maria do Carmo C. Silva

Metabolomics Research Group, UFBA, Salvador, Brazil

Laboratório de Ressonância Magnética Nuclear, UFSCar, São Carlos, Brazil

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Fernanda V. Carvalho

Fernanda V. Carvalho

Metabolomics Research Group, UFBA, Salvador, Brazil

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Antonio G. Ferreira

Antonio G. Ferreira

Laboratório de Ressonância Magnética Nuclear, UFSCar, São Carlos, Brazil

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Tiago Venâncio

Tiago Venâncio

Laboratório de Ressonância Magnética Nuclear, UFSCar, São Carlos, Brazil

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Maria Fátima G. F. da Silva

Maria Fátima G. F. da Silva

Laboratório de Produtos Naturais, UFSCar, São Carlos, Brazil

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Victor Diogenes A. Silva

Victor Diogenes A. Silva

Department of Biochemistry and Biophysics, UFBA, Salvador, Brazil

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Silvia L. Costa

Silvia L. Costa

Department of Biochemistry and Biophysics, UFBA, Salvador, Brazil

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Caline G. Ferraz

Corresponding Author

Caline G. Ferraz

Metabolomics Research Group, UFBA, Salvador, Brazil

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Paulo R. Ribeiro

Corresponding Author

Paulo R. Ribeiro

Metabolomics Research Group, UFBA, Salvador, Brazil

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First published: 21 July 2024
Citations: 1

Abstract

Three new polyprenylated benzophenone derivatives named burlemarxiones G−I (1-3) were isolated from C. burle-marxii trunks (compound 1) and leaves (compounds 2 and 3), along with the known compound burlemarxione F. Burlemarxione G (1) was isolated after methylation with diazomethane and it is the keto-enol tautomeric pair of burlemarxione F. Burlemarxione H (2) derives from burlemarxiones F and G, but it has additional rings due to cyclization of the prenyl group attached to C-5 that establishes new single bonds between C-1 and C-23, as well as, between C-24 and C-29. Burlemarxione I (3) has two additional cyclizations: the first encompasses the cyclization of the former isopentenyl group into an 11,11-dimethyl-six-membered ring, whereas the second produces additional rings due to the cyclization of the prenyl group attached to C-5 that establishes new single bonds between C-1 and C-23, as well as, between C-24 and C-29. All three compounds showed moderate anti-glioma activity. These results show that C. burle-marxii is an important source of sophisticated polyprenylated benzophenone derivatives.

Graphical Abstract

Conflict of Interests

The authors declare no conflict of interest.

Data Availability Statement

The data that support the findings of this study are available from the corresponding author upon reasonable request.

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