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, Kenichiro

Ueda, Shinichi

Shiobara, Yoshinori

Kimura, Inami

Inouye, 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.

Full text of DOI:10.1039/P19810001246

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online

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

R&D Labs maybe for 77939-87-8

Shantou Baokang Pharmaceutical Co., Ltd.

Contact:+86-754-88873487

Address:5/F B Block Huangshan Bldg Huangshan Rd Shantou
Shandong Wanda Organosilicon New Material Co., Ltd

Contact:+86-21-54177116;54302881

Address:R1318 Greenland No. 3 Lane 58 Xinjian East Rd., Minhang
Tianjin Anda North Industrial & Business Co.Ltd.

Contact:86-22-24999306

Address:No.11 Erwei Road,Dongli Development Area,Tianjin,China
NIGNXIA XINDACHANG TECHNOLOGY CO.,LTD

Contact:86-0951-7815345

Address:North side of Qiyuan Road, west side of Yuanfeng Highway, New Material Park, Ningdong Energy and Chemical Industry Base, Ningxia,China
WUHAN WELLSONG INT'L CO.,LTD

Contact:+86-27-85733560

Address:NO.308,QINGNIAN RD.,WUHAN,CHINA

Relevant to this article

Doi:10.1007/BF00777983
()
Asymmetric allylic C-H oxidation for the synthesis of chromans

Doi:10.1021/jacs.5b08477
(2015)
Rhodium-catalyzed asymmetric 1,4-addition of alkenylsilanes generated by hydrosilylation of alkynes: A one-pot procedure where a rhodium/(S)-binap complex catalyzes the two successive reactions

Doi:10.1016/j.tetasy.2004.07.003
(2004)
New Dimeric Indole Alkaloids from Stenosolen heterophyllus: Structure Determinations and Synthetic Approach

Doi:10.1021/jo00344a011
(1982)
Doi:10.1021/ja00405a035
(1981)
REACTIONS OF N-SULFINYL-p-TOLUENESULFONAMIDE WITH ALCOHOLS

Doi:10.1016/S0040-4020(01)92026-5
(1981)

Article Doi