Amide-esters from Aglaia tenuicaulis--first representatives of a class of compounds structurally related to bisamides and flavaglines.
Six amide-esters and two sulphur-containing bisamides were isolated from the leaves, stem and root bark of Aglaia tenuicaulis together with two bisamides from the leaves of A. spectabilis. Their structures were elucidated by spectroscopic methods. The co-occurrence of amide-esters and bisamides suggests close biosynthetic connections replacing only one nitrogen atom of putrescine with oxygen. Putrescine appears to be the common building block linked to various acids from which the cinnamoyl moiety represents the prerequisite for an incorporation of bisamides into flavaglines. Corresponding amide-esters are apparently not incorporated, but closely related amide-alcohol derivatives were found as part of benzopyran and benzofuran flavaglines. The structure of a amide-alcohol is described, representing an artifact due to hydrolysis of an amide-ester during TLC purification. A hypothetical amide-amine building block is suggested to form the characteristic pyrimidinone structures only found in benzofuran flavaglines. Structural and biosynthetic connections between amide-esters, bisamides and flavaglines are discussed and the chemotaxonomic significance of accumulating specific derivatives within the genus Aglaia is highlighted.
D031602:Aglaia / Q000737:chemistry*; D000577:Amides / Q000737:chemistry / Q000302:isolation & purification*; D001572:Benzofurans / Q000737:chemistry / Q000302:isolation & purification*; D001578:Benzopyrans / Q000737:chemistry / Q000302:isolation & purification*; D004952:Esters; D015394:Molecular Structure
D000577:Amides; D001572:Benzofurans; D001578:Benzopyrans; D004952:Esters