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

DOI: 10.1039/P19810001246

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1246 - 1258 (1981)

Update date:2022-08-04

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Authors:

Inoue, Kenichiro

Ueda, Shinichi

Shiobara, Yoshinori

Kimura, Inami

Inouye, Hiroyuki

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Article abstract of DOI:10.1039/P19810001246

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-(-2-carboxyphenyl)-4-hydroxy<4-3H>butanoic acid (32) to the original Catalpa plant and the callus tissues revealed that (3) is cyclised to COT and then reduced to CHT.

Full text of DOI:10.1039/P19810001246

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