Biosynthesis of the acetylenic compounds in cultured cells of Asparagus officinalis from D- and 13C-labelled phenylalanines.
Studies on the biosynthetic pathway of acetylenic compounds, 4-[5-(4-methoxyphenoxy)-3-penten-1-ynyl]phenol and its related compounds, in cultured cells of Asparagus officinalis L. (Liliaceae) revealed that all of the 17 carbon atoms in their skeletons are supplied by phenylalanine. It is also concluded that p-substituted phenylacetylenic moieties (the C6-C2 unit) in these compounds are derived from C6-C3 shikimate pathway metabolites via phenylalanine. As a working hypothesis concerning the C6-O-C3 unit formation, a spirotetrahydrofuran type intermediate is predicted.
Terada
K
K
School of Pharmaceutical Sciences, Mukogawa Women's University, Hyogo, Japan.
Suwa
K
K
Takeyama
S
S
Honda
C
C
Kamisako
W
W
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D002247:Carbon Isotopes; D002478:Cells, Cultured; D003903:Deuterium; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010649:Phenylalanine / Q000378:metabolism*; D012765:Shikimic Acid / Q000378:metabolism; D014675:Vegetables / Q000378:metabolism*
D002247:Carbon Isotopes; D012765:Shikimic Acid; D010649:Phenylalanine; D003903:Deuterium; D000114:Acetylene