Abibalsamins A and B, Two New Tetraterpenoids from Abies balsamea Oleoresin

S. Lavoie (1) , J. Legault (1) , C. Gauthier (2, 1) , V. Mshvildadze (1) , S. Mercier (1) , A. Pichette (1)

1 DSF - Département des Sciences Fondamentales [Chicoutimi]
2 IC2MP [Poitiers] - Institut de chimie des milieux et matériaux de Poitiers [UMR 7285]

Abibalsamins A (1) and B (2), two unprecedented tetraterpenoids featuring a 3,4-seco-rearranged Ianostane system fused with a beta-myrcene lateral chain via a [4 + 2] Diels-Alder cycloaddition, were isolated from the oleoresin of Abies balsamea. Their structures were elucidated by means of extensive 20 NMR, IR, and MS spectroscopy analyses. The absolute configuration of 1 was determined by single-crystal X-ray diffraction. Both compounds exhibited significant cytotoxic activity against cancer cell lines.

Domaines: Catalyse; Chimie organique; Autre

S. Lavoie, J. Legault, C. Gauthier, V. Mshvildadze, S. Mercier, et al.. Abibalsamins A and B, Two New Tetraterpenoids from Abies balsamea Oleoresin. Organic Letters, 2012, 14 (6), pp.1504-1507. ⟨10.1021/ol300237f⟩. ⟨hal-00819224⟩