H-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-D5-alanine-2,3,3-D3 (D5-phe) and DL-phenylalanine-3,3-D2 (D2-phe) yielded D-enriched asparenyol, 4-[5-(4-methoxyphenoxy)-3-penten-1-ynyllphenol (1). A H-NMR spectral study indicated that incorporation of deuterium atoms into the chains of the products was restricted to the C-9 position. The molecular ion regions of the MS of D-enriched metabolites, 1(D8-200), 1(D8-100) and 1(D8-50), obtained from feeding experiments using 200 mg, 100 mg and 50 mg of Ds-phe, respectively, coincided with the theoretical spectra. This confirmed that a single phenylalanine molecule supplies the nine carbon atoms in the -CH=CH-CH2-O-C6H4-O- moiety of 1. The biosynthetic sequence forming 1 as a norlignan class of metabolite is considered.
Terada
K
K
Gene Bank, The Institute of Physical and Chemical Research (RIKEN), Tsukuba Life Science Center, Ibaraki, Japan.
Kamisako
W
W
D002478:Cells, Cultured; D017705:Lignans / Q000096:biosynthesis / Q000737:chemistry*; D019668:Liliaceae / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
D017705:Lignans