Thiodiketopiperazines with two spirocyclic centers extracted from Botryosphaeria mamane, an endophytic fungus isolated from Bixa orellana L. (February 2019)

• Record Type: Journal Article
• Authors: Barakat, Fatima; Vansteelandt, Marieke; Triastuti, Asih; Jargeat, Patricia; Jacquemin, Denis; Graton, Jérôme; Mejia, Kember; Cabanillas, Billy; Vendier, Laure; Stigliani, Jean-Luc; Haddad, Mohamed; Fabre, Nicolas
• Is Part Of: Phytochemistry. Volume 158(2019)
• Page Start: 142
• Page End: 148
• Publication Date: 2019-02
• Subjects: Botryosphaeria mamane D.E. Gardner (Botryosphaeriaceae) -- Bixa orellana L. (Bixaceae) -- Thiodiketopiperazine -- Cytotoxic activity; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2018.11.007
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: 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. Graphical abstract: Three undescribed thiodiketopiperazines exhibiting two spirocyclic centers were extracted from the culture of the endophytic fungus Botryosphaeria mamane isolated from Bixa orellana leaves. Highlights: Three thiodiketopiperazines were isolated from Botryosphaeria mamane. These alkaloids possess unprecedent spiro[isoxazolidino-cyclohexenone] scaffold. Botryosulfuranol A inhibited the growth of both cancer and healthy cell lines.