Abietane Diterpenes from Hyptis crassifolia Mart. ex Benth. (Lamiaceae)

The phytochemical study of the ethanol extract from roots of Hyptis crassifolia Mart. ex Benth. (Lamiaceae) led to the isolation and structure elucidation of nine diterpenes identified as 11,12,15-trihydroxy-8,11,13-abietatrien-7-one, 6 alpha, 11,12,15-tetrahydroxy-8,11,13-abietatrien-7-one, 11,12,16-trihydroxy-17(15 -> 16)-abeo-abieta-8,11,13-trien-7-one, (16S)-12,16-epoxy-11,14-dihydroxy-17(15 -> 16)-abeo-abieta-8,11,13-trien-7-one, incanone, ferruginol, sugiol, 11-oxomanoyl oxide and 11 beta-hydroxymanoyl oxide. Compounds 11,12,16-trihydroxy-17(15 -> 16) -abeo-abieta-8,11,13-trien-7-one and 6 alpha, 11,12,15-tetrahydroxy-8,11,13-abietatrien-7-one are new, 11,12,15-trihydroxy-8,11,13-abietatrien-7-one is being reported for the first time as a new natural abietane diterpene, while for (16S)-12,16-epoxy-11,14-dihydroxy-17(15 -> 16)-abeo-abieta-8,11,13-trien-7-one, previously isolated from Teucrium divaricatum Subsp. villosum, a revision of the H-1 and C-13 nuclear magnetic resonance (NMR) data previously reported is proposed. Structure determination of all constituents was performed by mean of spectroscopic techniques such as high resolution mass spectrometry (HRMS), infrared (IR), H-1 and C-13 1D and 2D NMR and comparison with literature data.