Reference - Detail
| RRC ID | 32173 |
|---|---|
| Author | Ohyama K, Okawa A, Moriuchi Y, Fujimoto Y. |
| Title | Biosynthesis of steroidal alkaloids in Solanaceae plants: involvement of an aldehyde intermediate during C-26 amination. |
| Journal | 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. |
| Volume | 89 |
| Pages | 26-31 |
| Published | 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 |
| Times Cited | 22 |
| WOS Category | PLANT SCIENCES BIOCHEMISTRY & MOLECULAR BIOLOGY |
| Altmetric score |
オルトメトリクス指標項目
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| The most frequently cited source | Wikipedia |
| Total number of mentions | 4 |
| Altmetric score changes over past 6months | 0.0 |
| Resource | |
| Tomato | TOMJPF00001 |