Mechanism of the second methylation in sitosterol side-chain biosynthesis in higher plants: metabolic fate of 28-hydrogens of 24-methylenecholesterol in Morus alba cell cultures

2000 ◽  
Vol 41 (19) ◽  
pp. 3623-3626 ◽  
Author(s):  
Tatsuya Okuzumi ◽  
Yuko Kaji ◽  
Hiroki Hamada ◽  
Yoshinori Fujimoto
Keyword(s):  
Cell Cultures ◽  
Higher Plants ◽  
Morus Alba ◽  
Side Chain ◽  
Metabolic Fate

Morusalisins A-F, six new Diels-Alder type adducts, as potential PTP1B inhibitors from cell cultures of Morus alba

Fitoterapia ◽  
2020 ◽  
Vol 146 ◽  
pp. 104682
Author(s):  
Cong Su ◽  
Yangyang Duan ◽  
Jinying Tian ◽  
Jimei Liu ◽  
Kebo Xie ◽  
...  
Keyword(s):  
Cell Cultures ◽  
Diels Alder ◽  
Morus Alba ◽  
Ptp1b Inhibitors

Biosynthese von p-Hydroxybenzoesäure und anderer Benzoesäuren in höheren Pflanzen

1964 ◽  
Vol 19 (5) ◽  
pp. 398-405 ◽  
Author(s):  
M. H. Zenk ◽  
G. Müller
Keyword(s):  
Benzoic Acid ◽  
Protocatechuic Acid ◽  
Higher Plants ◽  
Side Chain ◽  
Hydroxybenzoic Acid ◽  
Benzoic Acids ◽  
Coumaric Acid ◽  
Cinnamic Acids ◽  
Feeding Experiments ◽  
Catalpa Ovata

Feeding experiments with glucose- (2-14C), phenylalanine- (3-14C), tyrosine- (3-14C) and p-coumaric acid- (3-14C) showed that the latter three substances are incorporated in good yields into p-hydroxybenzoic acid in leaves of Catalpa ovata. Kinetic experiments showed that p-hydroxybenzoic acid is formed from phenylalanine via p-coumaric acid and the subsequent β-oxidation of the side chain. p-Hydroxybenzoic acid can also be synthetised by hydroxylation of benzoic acid, but this does not seem to be the biosynthetic route in Catalpa.Phenylalanine- (3-14C) is also incorporated into benzoic acid, protocatechuic acid, and vanillic acid by different plants; the radioactivity of the β-C atom of the amino acid was found in each case to be located in the carboxyl group of the C6 — C1 acid. This suggests that in higher plants the benzoic acids are formed from the corresponding cinnamic acids via β-oxidation.

Late Stage of Biosynthesis of Intermolecular Diels-Alder Type Adducts in Morus alba L. Cell Cultures

Heterocycles ◽  
1999 ◽  
Vol 51 (2) ◽  
pp. 231 ◽  
Author(s):  
Taro Nomura ◽  
Yoshio Hano ◽  
Shinichi Ueda
Keyword(s):  
Cell Cultures ◽  
Late Stage ◽  
Diels Alder ◽  
Morus Alba ◽  
L Cell

scholarly journals Biosynthesis of phytoquinones. Homogentisic acid: a precursor of plastoquinones, tocopherols and α-tocopherolquinone in higher plants, green algae and blue–green algae

1970 ◽  
Vol 117 (3) ◽  
pp. 593-600 ◽  
Author(s):  
G. R. Whistance ◽  
D. R. Threlfall
Keyword(s):  
Green Algae ◽  
Phenylacetic Acid ◽  
Higher Plants ◽  
Chlorella Pyrenoidosa ◽  
Homogentisic Acid ◽  
Side Chain ◽  
Methyl Groups ◽  
Blue Green Algae ◽  
Hydroxyphenylacetic Acid ◽  
Tracer Experiments

1. By means of 14C tracer experiments and isotope competition experiments the roles of d-tyrosine, p-hydroxyphenylpyruvic acid, p-hydroxyphenylacetic acid, phenylacetic acid, homogentisic acid and homoarbutin (2-methylquinol 4-β-d-glucoside) in the biosynthesis of plastoquinones, tocopherols and α-tocopherolquinone by maize shoots was investigated. It was established that d-tyrosine, p-hydroxyphenylpyruvic acid and homogentisic acid can all be utilized for this purpose, whereas p-hydroxyphenylacetic acid, phenylacetic acid and homoarbutin cannot. Studies on the mode of incorporation of d-tyrosine, p-hydroxyphenylpyruvic acid and homogentisic acid showed that their nuclear carbon atoms and the side-chain carbon atom adjacent to the nucleus give rise (as a C6-C1 unit) to the p-benzoquinone rings and nuclear methyl groups (one in each case) of plastoquinone-9 and α-tocopherolquinone and the aromatic nuclei and nuclear methyl groups (one in each case) of γ-tocopherol and α-tocopherol. 2. By using [14C]-homogentisic acid it has been shown that homogentisic acid is also a precursor of plastoquinone, tocopherols and α-tocopherolquinone in the higher plants Lactuca sativa and Rumex sanguineus, the green algae Chlorella pyrenoidosa and Euglena gracilis and the blue–green alga Anacystis nidulans.

Direct NMR evidence for the equivalent participation of L-phenylalanine and L-tyrosine in the biosynthesis of the intermolecular Diels–Alder type adducts of prenylchalcone and prenylated 2-arylbenzofuran in Morus alba cell cultures

1994 ◽  
Vol 72 (1) ◽  
pp. 12-14 ◽  
Author(s):  
Yoshio Hano ◽  
Taro Nomura ◽  
Shinichi Ueda
Keyword(s):  
Amino Acids ◽  
Cell Cultures ◽  
Nmr Spectra ◽  
Diels Alder ◽  
Morus Alba ◽  
High Yields ◽  
C Nmr

L-[3-13C]Phenylalanine and L-[3-13C]tyrosine were administered to Morus alba cell cultures, to produce intermolecular Diels–Alder type adducts of a prenylchalcone and a 2-arylbenzofuran such as chalcomoracin (1) as well as the adducts of two molecules of prenylchalcones such as kuwanon J (2) in high yields. The 13C NMR spectra of 1 and 2 isolated from the cultures revealed that both amino acids were incorporated intact into chalcomoracin (1) and kuwanon J (2). This is the first example of direct NMR evidence for the almost equivalent incorporation of phenylalanine and tyrosine into the shikimate metabolites. This finding suggests the participation of a biosynthetic route from phenylalanine via trans-cinnamate to p-coumarate and from tyrosine to p-coumarate in this plant.

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