Extractives from six species of Lamiaceae

Abstract

In continuation of the phytochemical studies of plants belonging to the Lamiaceae (formerly Labiatae) the acetone extractives of six Southern African species from this family have been examined. The genus Syncolostemon has not been investigated before and a new 6- substituted-5 ,6-dihydro-a-pyrone , synrotolide was isolated from S. rotundifolius. The structure of synrotolide was fully elucidated as 6fixii [3'R, 61S-(diacetyloxy)-4 1R, 5 1 8-(dihydroxy)-1~-hepteny~ -5,6-dihydro-2H-pyran- 2-one. Oleanolic acid is the major component of both~ rotundifolius and S. densifloris. The flavonol quercetin was isolated from S. densifloris as its 3, 3', 4' , 7 tetramethyl ether. A further 6-substituted-5,6-dihydro-a-pyrone, boronolide, was obtained from Tetradenia barberae. The structure of boronolide was known but the absolute stereochemistry was unassigned. Chemical degradation established the total structure of this compound as 6R- [1 'R, 2'R, 3's -(trisacetyloxy)heptyl] -5,6-dihydro-2H-pyran-2-one. The chemistry of naturally occuring 6-substituted-5,6-dihydro-apyrones has not as such been previously reviewed and a comprehensive review covering the literature up to June 1987 is presented here. Three known labdane diterpenoids nepetaefuran, hispanalone and dubiin were iso lated from Leonotis nepetaefolia, Ballota africana and L. ocymifolia var. ocymifolia (formerly~ dubia). Both~ nepetaefolia and L. dubia have been examined before. An X-ray analysis of saponified dubiin and a circular dichroism study of 6-deacetyldehydrodubiin and related compounds corroborated the structure of dubiin as 48, 5R, 6R, 8R, 9R, 10R-[6-acetoxy-15,16-epoxy-9-hydroxylabda-13 (16), 14-dien-19, 20- olactoneJ. The chemotaxonomic relationships of the genera Ballota and Leonotis are discussed.