H-1-NMR and mass spectral study of a D-enriched acetylenic norlignan, asparenyol, from cultured cells of Asparagus officinalis

A suspension of cultured cells of Asparagus officinalis fed L-phenyl-D-5-al anine-2,3,3-D-3 (D-8-phe) and DL-phenylalanine-3,3-D-2 (D-2-phe) yielded D- enriched asparenyol, 4-[5-(4-methoxyphenoxy)-3-penten-1-ynyl]phenol (1), A H-1-NMR spectral study indicated that incorporation of deuterium atoms into the chains of the products was restricted to the C-9 position. The molecul ar ion regions of the MS of D-enriched metabolites, 1(D-8-200), 1(D-8-100) and 1(D-8-50), obtained from feeding experiments using 200 mg, 100 mg and 5 0 mg of D-8-phe, respectively, coincided with the theoretical spectra, This confirmed that a single phenylalanine molecule supplies the nine carbon at oms in the -CH=CH-CH2-O-C6H4-O- moiety of 1. The biosynthetic sequence form ing 1 as a norlignan class of metabolite is considered.