Welcome to LookChem.com Sign In|Join Free

Article Doi

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

Topics:

Authors:

Inoue, KenichiroInoue, Kenichiro

Ueda, ShinichiUeda, Shinichi

Shiobara, YoshinoriShiobara, Yoshinori

Kimura, InamiKimura, Inami

Inouye, HiroyukiInouye, Hiroyuki

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

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.

View More

Products guided by the article

Product name:1,4-Bis-benzoyloxy-3,4-dihydro-naphthalene-2-carboxylic acid methyl ester

Cas No:77939-87-8

77939-87-8

R&D Labs maybe for 77939-87-8

Relevant to this article

Hot Product