Biosynthesis of 24-methylcholest-5-en-3β-ol and 24-ethylcholest-5-en-3β-ol InZea Mays

Overview

Journal Lipids

Specialty Biochemistry

Date 2016 Aug 14

PMID 27519243

Citations 3

Authors

N Rendeli

N L Misso

L J Goad

Affiliations

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Abstract

The relative rates of synthesis of 24-methylcholest-5-en-3β-ol and 24-ethylcholest-5-en-3β-ol inZea mays shoots were determined using [2-(14)C]mevalonic acid and [methyl-(14)C]methionine as substrates. The 24-ethylsterol had a higher specific activity and it apparently was synthesized at about 3-4 times the rate of the 24-methylsterol.(1)H NMR spectroscopy showed that the 24-ethylsterol was predominantly the 24α-epimer but the 24-methylsterol was a mixture of the 24α-epimer (30-40%) and the 24β-epimer (60-70%). The results are discussed in relation to the involvement of Δ(24(28))-, Δ(23), Δ(25)- and Δ(24(25))-sterol intermediates in 24-methyl- and 24-ethylsterol production.

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References

Rahier A, Genot J, Schuber F, Benveniste P, Narula A . Inhibition of S-adenosyl-L-methionine sterol-C-24-methyltransferase by analogues of a carbocationic ion high-energy intermediate. Structure activity relationships for C-25 heteroatoms (N, As, S) substituted triterpenoid derivatives. J Biol Chem. 1984; 259(24):15215-23. View

Rahier A, Bouvier P, Cattel L, Narula A, Benveniste P . Inhibition of 2,3-oxidosqualene: beta-amyrin-cyclase, S-adenosyl-L-methionine: cycloartenol C-24-methyltransferase and cycloeucalenol: obtusifoliol isomerase by rationally designed molecules containing a tertiary amine function. Biochem Soc Trans. 1983; 11(5):537-43. DOI: 10.1042/bst0110537. View

Goad L . How is sterol synthesis regulated in higher plants?. Biochem Soc Trans. 1983; 11(5):548-52. DOI: 10.1042/bst0110548. View

Floss H, Tsai M . Chiral methyl groups. Adv Enzymol Relat Areas Mol Biol. 1979; 50:243-302. DOI: 10.1002/9780470122952.ch5. View

Ryder N, Goad L . The effect of the 3-hydroxy-3-methylglutaryl CoA reductase inhibitor ML-236b on phytosterol synthesis in Acer pseudoplatanus tissue culture. Biochim Biophys Acta. 1980; 619(2):424-7. DOI: 10.1016/0005-2760(80)90092-2. View