TYRAMINE DERIVATIVES FROM THE FRUIT OF LIMONIA-ACIDISSIMA

The isolation of two new tyramine derivatives, acidissiminol [1] and acidissiminin epoxide [2], and N-benzoyltyramine [3] from the fruits of Limonia acidissima is described. Structures were elucidated by uv, ir, nmr, eims, and/or cims measurements. The comparison of spectral data of 1 with those of an authentic sample prepared from acidissiminin [4], previously isolated from the same plant, conclusively established the structure of 1 as benzamide-N-{p-[(3,7-dimethyl-4-hydroxy-2,6-octadienyl)oxy]phenethyl}. Spin decoupling experiments on 2 and structure elucidation of degraded material 5 obtained through hydrolytic cleavage of 2, established the structure of acidissiminin epoxide [2] as benzamide-N-{p-[(3,7-dimethyl-6,7-epoxy-4-octadecanoyloxy--2-octenyl)oxy]phenethyl}.