Phytotoxic activity in Flourensia campestris and isolation of (--)-hamanasic acid A as its active principle compound

An aqueous extract from Flourensia campestris (Asteraceae) dry aerial parts showed strong inhibition on the germination and growth of Lactuca sativa. Based on bio-guided chromatographic fractionation of aq. extracts from dry and fresh leaves and spectroscopic means, (-)-hamanasic acid A (7-carboxy-8-hydroxy-1(2), 12(13)-dien-bisabolene (1)) was isolated as the most inhibitory active principle on germination (ECg(50)=2.9 mM) and on root (ECr(50)=1.5 mM)/shoot (ECs(50)=2.0 mM) growth. As measured by GC, and correlated with a simple designed 2D-TLC, compound 1 was distributed throughout the plant, with a remarkably high concentration (1.6%) in the leaves and the inflorescences. At least a quarter of the amount of 1 was found in aqueous extracts suggesting that leaching would be a key route for its release into the environment. By contrast, leaf essential oils (HD) between 0.5 and 1.5 μl ml(-1) did not show herbicidal effects and 1 was not found in them (TLC) nor among volatiles (HS-SPME). Volatile compositions were assessed by GC-FID and GC-MS and led to the identification of 23 compounds (4 monoterpenes and 19 sesquiterpenes) with a wide seasonal (spring-summer%) variation, represented principally by bicyclo-germacrene (37-6%), spathulenol (4-32%), globulol (20-0%), beta-caryophyllene (15-6%), caryophyllene oxide (1-13%) and bicycloelemene (10-1%), respectively. The high amount of 1 in F. campestris together with its feasibility of being extracted with water suggest that (-)-hamanasic acid A is an allelochemical in this species. Species-specific studies must be carried out to evaluate the potential of 1 as a natural herbicidal compound.