77939-88-9Relevant articles and documents
Quinones and Related Compounds in Higher Plants. Part 11. Role of 2-Carboxy-2,3-dihydro-1,4-naphthoquinone and 2-Carboxy-2-(3-methylbut-2-enyl)-2,3-dihydro-1,4-naphthoquinone in the Biosynthesis of Naphthoquinone Congeners of Catalpa ovata Callus Tissues
Inoue, Kenichiro,Ueda, Shinichi,Shiobara, Yoshinori,Kimura, Inami,Inouye, Hiroyuki
, p. 1246 - 1258 (2007/10/02)
Dilution analyses after administration of 14C-labelled 4-(2-carboxyphenyl)-4-oxobutanoic acid (3) to the callus tissues of Catalpa ovata demonstrated the following results: (i) 2-Carboxy-4-oxo-1-tetralone (COT), 2-carboxy-4-hydroxy-1-tetralone (CHT), prenyl-COT (4), and prenyl-CHT (5) are on the biosynthetic pathway of naphthoquinones; (ii) the route passing through COT -> prenyl-COT (4) -> catalponone (6) is the main pathway of the biosynthesis of naphthoquinones, whereas there exists a subsidiary route passing through CHT -> prenyl-CHT (5) -> catalponol (2); (iii) regarding the key intermediates prenyl-COT (4) and catalponone (6), (2S)-prenyl-COT and (2R)-catalponone participate in the biosynthesis and both prenylation and decarboxylation proceed stereoselectively; and (iv) the acid (3) was incorporated into menaquinone-1 (7), 1-hydroxy-2-methylanthraquinone (8), 3-hydroxydehydro-iso-α-lapachone (9), etc., in the callus tissues.Furthermore, administration of 4-(-2-carboxyphenyl)-4-hydroxybutanoic acid (32) to the original Catalpa plant and the callus tissues revealed that (3) is cyclised to COT and then reduced to CHT.