Glucobrassicin
Encyclopedia
Glucobrassicin is a type of glucosinolate
that can be found in almost all cruciferous plants, such as cabbages (e.g.broccoli
), mustards
, cress
, and woad
. As for other glucosinolates, degradation by the enzyme myrosinase is expected to produce an isothiocyanate, indol-3-ylmethylisothiocyanate. However, this specific isothiocyanate is expected to be highly unstable, and has indeed never been detected. The observed hydrolysis products when isolated glucobrassicin is degraded by myrosinase are Indole-3-carbinol
and thiocyanate ion (plus glucose, sulphate, and hydrogen ion), which are envisioned to result from a rapid reaction of the unstable isothiocyanate with water. However, a large number of other reaction products are known, and indole-3-carbinol is not the dominant degradation product when glucosinolate degradation takes place in crushed plant tissue (Agerbirk et al., 2009) or in intact plants (Clay et al., 2009; Bednarek et al., 2009).
Indole-3-carbinol and/or products of additional reactions such as diindolylmethane may help prevent cancer
, but the effect is still not completely understood. Some adverse effects may in fact be expected, at least at high doses (probably higher than you would get by eating vegetable
s).
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 produt was discovered, it was named neoglucobrassicin. When further derivatives were discovered, a more systematic nomenclature was used.
Currently, the following five derivatives are known from plants:
The existence of a sixth derivative, 1-acetylglucobrassicin, has been suggested, but the data were insufficient so whether this compound exists or not in nature is not known (by 2008).
The three first mentioned derivatives are as frequent in crucifers as glucobrassicin itself. The additional two 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 (Clay et al., 2009; Bednarek et al., 2009).
Glucosinolate
The glucosinolates are a class of organic compounds that contain sulfur and nitrogen and are derived from glucose and an amino acid. They occur as secondary metabolites of almost all plants of the order Brassicales , but also in the genus Drypetes .-Chemistry:Glucosinolates are water-soluble...
that can be found in almost all cruciferous plants, such as cabbages (e.g.broccoli
Broccoli
Broccoli is a plant in the cabbage family, whose large flower head is used as a vegetable.-General:The word broccoli, from the Italian plural of , refers to "the flowering top of a cabbage"....
), mustards
Mustard plant
Mustards are several plant species in the genera Brassica and Sinapis whose small mustard seeds are used as a spice and, by grinding and mixing them with water, vinegar or other liquids, are turned into the condiment known as mustard or prepared mustard...
, cress
Cress
-Plants:* Alpine Rock Cress* Bulbous Cress* Cedar Glade Cress* Garden cress, a leafy vegetable* Hoary Bitter Cress* Hoary Cress* Indian Cress* Land cress, a biennial herb* Marsh Cress* Peppercress, a mustard* Rockcress, several brassicales...
, and woad
Woad
Isatis tinctoria, with Woad as the common name, is a flowering plant in the family Brassicaceae. It is commonly called dyer's woad, and sometimes incorrectly listed as Isatis indigotica . It is occasionally known as Asp of Jerusalem...
. As for other glucosinolates, degradation by the enzyme myrosinase is expected to produce an isothiocyanate, indol-3-ylmethylisothiocyanate. However, this specific isothiocyanate is expected to be highly unstable, and has indeed never been detected. The observed hydrolysis products when isolated glucobrassicin is degraded by myrosinase are Indole-3-carbinol
Indole-3-carbinol
Indole-3-carbinol is produced by the breakdown of the glucosinolate glucobrassicin, which can be found at relatively high levels in cruciferous vegetables. Indole-3-carbinol is the subject of on-going Biomedical research into its possible anticarcinogenic, antioxidant, and anti-atherogenic effects...
and thiocyanate ion (plus glucose, sulphate, and hydrogen ion), which are envisioned to result from a rapid reaction of the unstable isothiocyanate with water. However, a large number of other reaction products are known, and indole-3-carbinol is not the dominant degradation product when glucosinolate degradation takes place in crushed plant tissue (Agerbirk et al., 2009) or in intact plants (Clay et al., 2009; Bednarek et al., 2009).
Indole-3-carbinol and/or products of additional reactions such as diindolylmethane may help prevent cancer
Cancer
Cancer , known medically as a malignant neoplasm, is a large group of different diseases, all involving unregulated cell growth. In cancer, cells divide and grow uncontrollably, forming malignant tumors, and invade nearby parts of the body. The cancer may also spread to more distant parts of the...
, but the effect is still not completely understood. Some adverse effects may in fact be expected, at least at high doses (probably higher than you would get by eating vegetable
Vegetable
The noun vegetable usually means an edible plant or part of a plant other than a sweet fruit or seed. This typically means the leaf, stem, or root of a plant....
s).
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 produt was discovered, it was named neoglucobrassicin. When further derivatives were discovered, a more systematic nomenclature was used.
Currently, the following five derivatives are known from plants:
- 1-methoxyglucobrassicin (=neoglucobrassicin),
- 4-hydroxyglucobrassicin,
- 4-methoxyglucobrassicin,
- 1,4-dimethoxyglucobrassicin, and
- 1-sulphoglucobrassicin.
The existence of a sixth derivative, 1-acetylglucobrassicin, has been suggested, but the data were insufficient so whether this compound exists or not in nature is not known (by 2008).
The three first mentioned derivatives are as frequent in crucifers as glucobrassicin itself. The additional two 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 (Clay et al., 2009; Bednarek et al., 2009).