Issue 73, 2020, Issue in Progress
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RSC Advances

Desmoschinensisflavones A and B, two rare flavones having a hybrid benzyl benzoate ester-flavone structural framework from Desmos chinensis Lour†

Isaraporn Polbuppha, ORCID logo ab   Virayu Suthiphasilp, ORCID logo a   Tharakorn Maneerat,ac   Rawiwan Charoensup,cd   Thunwadee Limtharakul, ORCID logo e   Sarot Cheenpracha, ORCID logo f   Stephen G. Pyne ORCID logo *b  and  Surat Laphookhieo ORCID logo *ac  

* Corresponding authors

a Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai 57100, Thailand
E-mail: surat.lap@mfu.ac.th

b School of Chemistry and Molecular Bioscience, University of Wollongong, Wollongong, New South Wales 2522, Australia
E-mail: spyne@uow.edu.au

c Medicinal Plant Innovation Center of Mae Fah Luang University, Chiang Rai 57100, Thailand

d School of Integrative Medicine, Mae Fah Luang University, Chiang Rai 57100, Thailand

e Department of Chemistry, Faculty of Science, Research Center on Chemistry for Development of Health Promoting Products from Northern Resources, Chiang Mai University, Chiang Mai 50200, Thailand

f School of Science, University of Phayao, Phayao 56000, Thailand

Abstract

Two rare flavones having a hybrid benzyl benzoate ester-flavone structural framework, desmoschinensisflavones A and B (1 and 2), together with 12 known compounds (3–14) were isolated from the fruit, leaf, and twig extracts of Desmos chinensis (red flower). The new structures were characterized by UV, IR, NMR, and HRESITOFMS data. Desmoschinensisflavones A and B have a distinctive skeleton of benzoate ester-flavones with a C-4′′ and C-6 and C-8 connection via a methylene group, respectively. Plausible biosynthesis pathways to compounds 1 and 2 are proposed based on an intermolecular nucleophilic 1,4-addition to ortho-quinone intermediates. Compounds 6–8 and 12 showed weakly antioxidant inhibition with IC50 values in the range of 65.4–74.6 μM.

Graphical abstract: Desmoschinensisflavones A and B, two rare flavones having a hybrid benzyl benzoate ester-flavone structural framework from Desmos chinensis Lour

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Article information

DOI
https://doi.org/10.1039/D0RA09985F
Article type
Paper
Submitted
25 Nov 2020
Accepted
09 Dec 2020
First published
21 Dec 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 45076-45080

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Desmoschinensisflavones A and B, two rare flavones having a hybrid benzyl benzoate ester-flavone structural framework from Desmos chinensis Lour

I. Polbuppha, V. Suthiphasilp, T. Maneerat, R. Charoensup, T. Limtharakul, S. Cheenpracha, S. G. Pyne and S. Laphookhieo, RSC Adv., 2020, 10, 45076 DOI: 10.1039/D0RA09985F

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