Glucobrassicin
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Names | |
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IUPAC name
1-S-[(1Z)-2-(1H-Indol-3-yl)-N-(sulfooxy)ethanimidoyl]-1-thio-β-D-glucopyranose
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Other names
Indol-3-ylmethylglucosinolate
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChemSpider | |
ECHA InfoCard
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100.231.968 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C16H20N2O9S2 | |
Molar mass | 448.46 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Glucobrassicin is a type of
Glucobrassicin is also known to be a highly active egg-laying stimulant of cabbage white butterflies such as the small white (Pieris rapae) and the large white (Pieris brassicae).
Several derivatives of glucobrassicin are known. The compound itself was first isolated from Brassica plants, hence the ending of the name. When a second, similar natural product was discovered, it was named neoglucobrassicin. When further derivatives were discovered, a more systematic nomenclature was used. Currently, the following six derivatives are known from plants:
- 1-Methoxyglucobrassicin (neoglucobrassicin)
- 4-Hydroxyglucobrassicin
- 4-Methoxyglucobrassicin
- 1,4-Dimethoxyglucobrassicin
- 1-Sulfoglucobrassicin
- 6′-Isoferuloylglucobrassicin
The three first mentioned derivatives are as frequent in crucifers as glucobrassicin itself. The additional three derivatives appear to be rare in nature. 4-methoxyglucobrassicin was recently reported to be a signal molecule involved in plant defence against bacteria and fungi.[2][3]
Biosynthesis from tryptophan
The biosynthesis of glucobrassicin begins with tryptophan produced through several steps from the
![](http://upload.wikimedia.org/wikipedia/commons/thumb/4/48/Biosynthesis_of_Glucobrassicin.png/220px-Biosynthesis_of_Glucobrassicin.png)
See also
References
Further reading
- Galletti, Stefania; Barillari, Jessica; Iori, Renato; Venturi, Gianpietro (2006). "Glucobrassicin enhancement in woad (Isatis tinctoria) leaves by chemical and physical treatments". Journal of the Science of Food and Agriculture. 86 (12): 1833. .