論文 - 詳細
RRC ID | 32170 |
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著者 | Ohyama K, Okawa A, Fujimoto Y. |
タイトル | Biosynthesis of steroidal alkaloids in Solanaceae plants: incorporation of 3β-hydroxycholest-5-en-26-al into tomatine with tomato seedlings. |
ジャーナル | 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. |
巻・号 | 24(15) |
ページ | 3556-8 |
公開日 | 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 | 2.572 |
引用数 | 4 |
WOS 分野 | CHEMISTRY, MEDICINAL CHEMISTRY, ORGANIC |
リソース情報 | |
トマト | TOMJPF00001 |