Abstract
In sweet clover ( Melitolotus alba Desr.) coumarin and related compounds occur primarily as β- d-glucosides. Synthetic trans o-(β- d-6- 3H-glucosyloxy) cinnamic acid α- 14C was administered to sweet clover shoots. Analysis of subsequently isolated trans and cis o-(β- d-glucosyloxy)-cinnamic acid and o-(β- d-glucosyloxy)-hydrocinnamic acid showed that in the in vivo conversion of the former glucosides to the latter glucoside, significant retention of glucose had occurred. These results indicate that in the in vivo conversion free coumarin is not an important intermediate. Identical results obtained from genotypes containing β-glucosidase and genotypes lacking β-glucosidase confirm the latter statement. Results from comparisons of the dilutions of specific activity of the isolated glucosides indicated that the trans isomer rather than the cis isomer of o-(β- d-glucosyloxy)-cinnamic acid is reduced to the corresponding hydrocinnamic acid derivative. Methods involving ion-exchange column chromatography and TLC separation of the three mentioned glucosides also are described.
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