RRC ID 32170
Author Ohyama K, Okawa A, Fujimoto Y.
Title Biosynthesis of steroidal alkaloids in Solanaceae plants: incorporation of 3β-hydroxycholest-5-en-26-al into tomatine with tomato seedlings.
Journal Bioorg. Med. Chem. Lett.
Abstract The C-26 amino group of tomatine, a representative Solanaceae steroidal alkaloid, is introduced in an early step of its biosynthesis from cholesterol. We recently proposed a transamination mechanism for the C-26 amination as opposed to the previously proposed mechanism involving a nitrogen nucleophilic displacement. In the present study, a deuterium labeled C-26 aldehyde, (24,24,27,27,27-(2)H5)-3β-hydroxycholest-5-en-26-al, was synthesized and fed to a tomato (Solanum lycopersicum) seedling. LC-MS analysis of the biosynthesized tomatine indicated that the labeled aldehyde was incorporated into tomatine. The finding strongly supports the intermediacy of the aldehyde and the transamination mechanism during C-26 amination.
Volume 24(15)
Pages 3556-8
Published 2014-8-1
DOI 10.1016/j.bmcl.2014.05.048
PII S0960-894X(14)00548-4
PMID 24909078
MeSH Alkaloids / biosynthesis* Alkaloids / chemistry Cholesterol / analogs & derivatives* Cholesterol / chemical synthesis Cholesterol / chemistry Cholesterol / metabolism Molecular Conformation Seedlings / chemistry Seedlings / metabolism* Solanaceae / chemistry Solanaceae / metabolism* Steroids / biosynthesis* Steroids / chemistry Tomatine / chemistry Tomatine / metabolism*
IF 2.442
Times Cited 3
WOS Category CHEMISTRY, MEDICINAL CHEMISTRY, ORGANIC
Resource
Tomato TOMJPF00001