Journal of the Chemical Society. Perkin transactions I p. 1246 - 1258 (1981)
Update date:2022-08-04
Topics:
Inoue, Kenichiro
Ueda, Shinichi
Shiobara, Yoshinori
Kimura, Inami
Inouye, Hiroyuki
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 <(2S)-(4)> and (2R)-catalponone <(2R)-(6)> 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-(
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Doi:10.1007/BF00777983
()Doi:10.1021/jacs.5b08477
(2015)Doi:10.1016/j.tetasy.2004.07.003
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(1982)Doi:10.1021/ja00405a035
(1981)Doi:10.1016/S0040-4020(01)92026-5
(1981)
