Tsavoenones A–C: unprecedented polyketides with a 1,7-dioxadispiro[4.0.4.4]tetradecane core from the lichen Parmotrema tsavoense

Thuc-Huy Duong; Mehdi A. Beniddir; Grégory Genta-Jouve; Thammarat Aree; Marylène Chollet-Krugler; Joël Boustie; Solenn Ferron; Aurélie Sauvager; Huu-Hung Nguyen; Kim-Phi-Phung Nguyen; Warinthorn Chavasiri; Pierre Le Pogam

doi:10.1039/C8OB01280F

Tsavoenones A–C: unprecedented polyketides with a 1,7-dioxadispiro[4.0.4.4]tetradecane core from the lichen Parmotrema tsavoense†

Thuc-Huy Duong,^ab Mehdi A. Beniddir,

^c Grégory Genta-Jouve,

^d Thammarat Aree,

^e Marylène Chollet-Krugler,^f Joël Boustie,^f Solenn Ferron,^f Aurélie Sauvager,^f Huu-Hung Nguyen,^g Kim-Phi-Phung Nguyen,^h Warinthorn Chavasiri*^e and Pierre Le Pogam

*^c

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* Corresponding authors

^a Department for Management of Science and Technology Development, Ton Duc Thang University, Ho Chi Minh City, Vietnam

^b Faculty of Applied Sciences, Ton Duc Thang University, Ho Chi Minh City, Vietnam

^c Équipe “Pharmacognosie-Chimie des Substances Naturelles”, BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, France
E-mail: pierre.le-pogam-alluard@u-psud.fr
Tel: +33 1 46 83 55 97

^d Équipe C-TAC, UMR CNRS 8638 COMETE – Université Paris Descartes, 4 Avenue de l'Observatoire, 75006 Paris, France

^e Natural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Phayathai Rd., Patumwan, Bangkok 10330, Thailand
E-mail: warinthorn.c@chula.ac.th

^f Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) – UMR 6226, F-35000 Rennes, France

^g Faculty of Biotechnology and environment, Nguyen Tat Thanh University, 300A Nguyen Tat Thanh, District 4, Ho Chi Minh City 748355, Vietnam

^h Department of Organic Chemistry, University of Science, National University – Ho Chi Minh City, 227 Nguyen Van Cu Str., Dist. 5, Ho Chi Minh City 748355, Vietnam

Abstract

New racemic dispiranic polyketides, tsavoenones A (1), B (2) and C (3), having a novel 1,7-dioxadispiro[4.0.4.4]tetradecane scaffold were isolated from the foliose lichen Parmotrema tsavoense. These compounds were structurally elucidated by extensive NMR analyses, comparison between experimental and theoretical ¹³C NMR data and X-ray crystallography. A putative biosynthetic scenario for the formation of 1–3 from parmosidone D, a meta-depsidone previously isolated from the same lichen material, was proposed. Tested for its cytotoxicity, 1 displayed a moderate activity against human myelogenous leukemia K562 cell line with an IC₅₀ value of 66 μg mL⁻¹.

This article is part of the themed collection: Chemical Biology in OBC

Organic & Biomolecular Chemistry

Tsavoenones A–C: unprecedented polyketides with a 1,7-dioxadispiro[4.0.4.4]tetradecane core from the lichen Parmotrema tsavoense†

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Tsavoenones A–C: unprecedented polyketides with a 1,7-dioxadispiro[4.0.4.4]tetradecane core from the lichen Parmotrema tsavoense

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