Crystal structure and Hirshfeld surface analysis of the methanol solvate of sclareol, a labdane-type diterpenoid

Abstract

The title compound, C20H36O2·CH3OH [systematic name: (3S)-4-[(S)-3-hydroxy-3-methylpent-4-en-1-yl]-3,4a,8,8-tetramethyldecahydronaphthalen-3-ol methanol monosolvate], is a methanol solvate of sclareol, a diterpene oil isolated from the medicinally important medicinal herb Salvia sclarea, commonly known as clary sage. It crystallizes in space group P1 (No. 1) with Z′ = 2. The sclareol molecule comprises two trans-fused cyclohexane rings, each having an equatorially oriented hydroxyl group, and a 3-methylpent-1-en-3-ol side chain. In the crystal, Os—H...Os, Os—H...Om, Om—H...Os and Om—H...Om (s = sclareol, m = methanol) hydrogen bonds connect neighboring molecules into infinite [010] chains. The title compound exhibits weak anti-leishmanial activity (IC50 = 66.4 ± 1.0 µM ml−1) against standard miltefosine (IC50 = 25.8 ± 0.2 µM ml−1).

Keywords

• labdane diterpene
• salvia sclarea l
• clary sage
• solvate
• hirshfeld surface analysis
• leishmaniasis
• crystal structure