Ligerin, an antiproliferative chlorinated sesquiterpenoid from a marine-derived Penicillium strain.

Marieke Vansteelandt (1) , Elodie Blanchet (1) , Maxim Egorov , Fabien Petit , Loïc Toupet (2) , Arnaud Bondon (3) , Fabrice Monteau (4) , Bruno Le Bizec (4) , Olivier P Thomas (5) , Yves François Pouchus (1) , Ronan Le Bot , Olivier Grovel (1)

1 MMS - Mer, molécules et santé EA 2160
2 IPR - Institut de Physique de Rennes
3 Structures et interactions moléculaires
4 LABERCA - Laboratoire d'étude des Résidus et Contaminants dans les Aliments
5 ICN - Institut de Chimie de Nice

A new chlorinated sesquiterpenoid analogue of fumagillin, ligerin (1), was isolated from a marine-derived strain of Penicillium, belonging to the subgenus Penicillium, along with the known compounds penicillic acid (2), orcinol, and orsellinic acid. Chemical structures were established by an interpretation of spectroscopic data including IR, UV, and HRESIMS, together with analyses of 1D and 2D NMR spectra and X-ray analysis for the determination of the absolute configuration. Ligerin (1) displayed strong inhibitory activity against an osteosarcoma cell line. This is the first report of the isolation of a fumagillin analogue from a marine-derived Penicillium strain.

Mots clés: SPOROTHRIX SP FO-4649; NATURAL-PRODUCTS; FUMAGILLIN; ELUCIDATION; DERIVATIVES; CHLOVALICIN; ANALOGS

Domaines: Biophysique

Marieke Vansteelandt, Elodie Blanchet, Maxim Egorov, Fabien Petit, Loïc Toupet, et al.. Ligerin, an antiproliferative chlorinated sesquiterpenoid from a marine-derived Penicillium strain.. Journal of Natural Products, 2013, 76 (2), pp.297-301. ⟨10.1021/np3007364⟩. ⟨hal-00815736⟩