RRC ID 32173
著者 Ohyama K, Okawa A, Moriuchi Y, Fujimoto Y.
タイトル Biosynthesis of steroidal alkaloids in Solanaceae plants: involvement of an aldehyde intermediate during C-26 amination.
ジャーナル Phytochemistry
Abstract The C-26 amino group of steroidal alkaloids, such as tomatine, is introduced during an early step of their biosynthesis from cholesterol. In the present study, the mechanism of C-26 amination was reinvestigated by administering stable isotope labeled compounds, such as (26,26,26,27,27,27-(2)H6)cholesterol during biosynthesis of tomatine, solanine and solasonine. The chemical compositions of tomatine and solanine so obtained were analyzed by LC-MS after administering the d6-cholesterol to a tomato seedling and a potato shoot, respectively. The resulting spectra indicated that two deuterium atoms were eliminated from C-26 of cholesterol during biosynthesis. Furthermore, administration of (6-(13)C(2)H3)mevalonate in combination with lovastatin to an eggplant seedling, followed by GC-MS analysis of solasodine after TMS derivatization established that two deuterium atoms were eliminated from C-26 of cholesterol during solasonine biosynthesis. These findings are in contrast to an earlier observation that one hydrogen atom was lost from C-26 during tomatidine biosynthesis, and suggest that C-26 nitrogen atom addition involves an aldehyde intermediate. Thus, it is proposed that the C-26 amination reaction that occurs during steroidal alkaloid biosynthesis proceeds by way of a transamination mechanism.
巻・号 89
ページ 26-31
公開日 2013-5-1
DOI 10.1016/j.phytochem.2013.01.010
PII S0031-9422(13)00032-0
PMID 23473422
MeSH Aldehydes / metabolism* Alkaloids / biosynthesis* Alkaloids / chemistry* Amination Solanaceae / metabolism* Steroids / chemistry*
IF 3.044
引用数 22
WOS 分野 PLANT SCIENCES BIOCHEMISTRY & MOLECULAR BIOLOGY
リソース情報
トマト TOMJPF00001