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Structural and Biosynthetic Studies of Natural Products of the Asteraceae and Lamiaceae.

As part of the investigation of the allelopathic interactions of members of the Florida scrub community, the chemical constituents of Solidago pauciflosculosa (Asteraceae) and Calamintha ashei (Lamiaceae) were studied. Aqueous and organic extracts of fresh leaves of S. pauciflosculosa provided large amounts of diterpene acids. The two major diterpenes isolated, 17-oxygrindelic acid and 17-oxogrindelic acid, showed significant inhibitory effects on germination and radicle growth of two Florida sandhill grasses, Schizachyrium scoparium and Leptochloa dubia. The organic extracts of S. pauciflosculosa were very rich in sesquiterpenes, the three major sesquiterpenes being (+)-epicurlone, (+)-episesquiphellandrene and (-)-a-trans-bergamotene. These three compounds did not show any significant effects on the germination and radicle growth of test species. Fresh leaves of C. ashei were very rich in menthofuran monoterpenes and flavonoids. The two major monoterpenes, epievodone and desacetylcalaminthone exhibited strong inhibitory effects on the germination and root growth of test species at concentrations of 106 and 92 ppm, respectively, whereas the flavonoids showed no effects. Investigation of the chemical constituents of the roots of S. pauciflosculosa, S. canadensis and S. sempervirens provided acetylenic compounds and diterpene acids. cis,cisand cis,trans-Matricaria esters from S. pauciflosculosa as well as cis-dehydromatricaria ester from S. canadensis showed strong inhibitory effects on the germination of test species. cis,cis-Matricaria ester completely inhibited germination of Florida sandhill grasses at 106 and 53 ppm.