Thiodiketopiperazines with two spirocyclic centers extracted from Botryosphaeria mamane, an endophytic fungus isolated from Bixa orellana L - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Phytochemistry Année : 2019

Thiodiketopiperazines with two spirocyclic centers extracted from Botryosphaeria mamane, an endophytic fungus isolated from Bixa orellana L

Résumé

Three thiodiketopiperazines, botryosulfuranols A-C (1–3) were isolated from the endophytic fungus Botryosphaeria mamane. The three compounds present sulfur atoms on α- and β-positions of phenylalanine derived residues and unprecedented two spirocyclic centers at C-4 and C-2′. Their planar structures were determined by spectroscopic analysis and absolute configurations were achieved by X-ray diffraction analysis and ECD and NMR chemical shifts calculations. Botryosulfuranol A (1) was the most cytotoxic compound against four cancer cell lines (HT-29, HepG2, Caco-2, HeLa) and two healthy cell lines (IEC6, Vero) highlighting the importance of an electrophilic center for cell growth inhibition.
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hal-02132387 , version 1 (17-05-2019)

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Fatima Barakat, Marieke Vansteelandt, Asih Triastuti, Patricia Jargeat, Denis Jacquemin, et al.. Thiodiketopiperazines with two spirocyclic centers extracted from Botryosphaeria mamane, an endophytic fungus isolated from Bixa orellana L. Phytochemistry, 2019, 158, pp.142-148. ⟨10.1016/j.phytochem.2018.11.007⟩. ⟨hal-02132387⟩
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