Sulforaphane: Difference between revisions
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{{Image|Sulforaphane.png|right|350px|Sulforaphane.}} | {{Image|Sulforaphane.png|right|350px|Sulforaphane.}} | ||
'''Sulforaphane''' is a biochemical, present in many | '''Sulforaphane''' is a biochemical, present in many [[cruciferous]] vegetables in the mustard family, that has been shown to have numerous healthful benefits. It has been shown to reduce cardio-vascular disease | ||
<ref name=Malaguti>{{cite journal | journal = Journal of Molecular and Cellular Cardiology | title = Sulforaphane in the protection of cardiomyocytes from oxidative stress | authors = M. Malaguti, C. Angeloni, E. Leoncini, E. Pagnotta, P. Biaga and S. Hrelia | volume = 42 | pages = S188 | year = 2007 | doi= 10.1016/j.yjmcc.2007.03.575 }}</ref>, cancers and ulcers. | |||
<ref name=Yanaka>{{cite journal | journal = Cancer Prevention Research | title = Dietary Sulforaphane-Rich Broccoli Sprouts Reduce Colonization and Attenuate Gastritis in Helicobacter pylori–Infected Mice and Humans | authors = A. Yanaka, J. W. Fahey, A. Fukumoto1, M. Nakayama1, S. Inoue1, S. Zhang, M. Tauchi, H. Suzuki, I. Hyodo and M. Yamamoto | volume = 2 | pages = 353-360 | year = 2009 | doi= 10.1158/1940-6207.CAPR-08-0192 }}</ref> [[Broccoli]] sprouts are the richest natural source of [[sulforaphane glucosinate]] (actually a precursor [[glucoraphanin]] form), which can also be found in broccoli, [[cauliflower]], [[cabbage]], [[kale]] and [[radish|radishes]]. Sulforaphane has been shown to reduce the formation of DNA adducts caused by ingestion of cancinogens such as [[benzo(a)pyrene]], a known cancer-causing agent. | |||
Sulforaphane is a [[bacteriocide|bactericidal]] agent against [[Helicobacter pylori]], infections of which are associated with both ulcers and cancers of the [[gastric system]]. The protective effects of sulforaphane towards both stomach cancers and cardiovascular disease appear to be associated with the ''nrf2'' gene, because animal knockout species lacking this gene fail to benefit from the administration of sulforaphane.<ref name=Yanaka>{{cite journal | journal = Cancer Prevention Research | title = Dietary Sulforaphane-Rich Broccoli Sprouts Reduce Colonization and Attenuate Gastritis in Helicobacter pylori–Infected Mice and Humans | authors = A. Yanaka, J. W. Fahey, A. Fukumoto1, M. Nakayama1, S. Inoue1, S. Zhang, M. Tauchi, H. Suzuki, I. Hyodo and M. Yamamoto | volume = 2 | pages = 353-360 | year = 2009 | doi= 10.1158/1940-6207.CAPR-08-0192 }}</ref> | |||
== Chemistry == | |||
The [[IUPAC]] name for sulforaphane is 1-isothiocyanato-4(R)-methylsulfinylbutane. Because it is produced biochemically, the [[sulfoxide]] group of sulforaphane possesses [[stereochemistry]] and occurs as only the [[stereoisomer]] depicted in the structure above as elucidate by Vergara et al.<ref name=Vergara>{{cite journal | journal = Phytochemistry | title = Determination of the absolute configuration of the glucosinolate methyl sulfoxide group reveals a stereospecific biosynthesis of the side chain| authors = F. Vergaraa, M. Wenzlera, B. G. Hansenb, D. J. Kliebensteinc, B. A. Halkierb, J. Gershenzona and B. Schneider | volume = 69 | pages = 2737-2742 | year = 2008 | doi= 10.1016/j.phytochem.2008.09.008 }}</ref> | |||
== References == | == References == | ||
<references/> | <references/> | ||
Latest revision as of 08:24, 28 October 2009
Sulforaphane is a biochemical, present in many cruciferous vegetables in the mustard family, that has been shown to have numerous healthful benefits. It has been shown to reduce cardio-vascular disease [1], cancers and ulcers. [2] Broccoli sprouts are the richest natural source of sulforaphane glucosinate (actually a precursor glucoraphanin form), which can also be found in broccoli, cauliflower, cabbage, kale and radishes. Sulforaphane has been shown to reduce the formation of DNA adducts caused by ingestion of cancinogens such as benzo(a)pyrene, a known cancer-causing agent.
Sulforaphane is a bactericidal agent against Helicobacter pylori, infections of which are associated with both ulcers and cancers of the gastric system. The protective effects of sulforaphane towards both stomach cancers and cardiovascular disease appear to be associated with the nrf2 gene, because animal knockout species lacking this gene fail to benefit from the administration of sulforaphane.[2]
Chemistry
The IUPAC name for sulforaphane is 1-isothiocyanato-4(R)-methylsulfinylbutane. Because it is produced biochemically, the sulfoxide group of sulforaphane possesses stereochemistry and occurs as only the stereoisomer depicted in the structure above as elucidate by Vergara et al.[3]
References
- ↑ (2007) "Sulforaphane in the protection of cardiomyocytes from oxidative stress". Journal of Molecular and Cellular Cardiology 42: S188. DOI:10.1016/j.yjmcc.2007.03.575. Research Blogging.
- ↑ 2.0 2.1 (2009) "Dietary Sulforaphane-Rich Broccoli Sprouts Reduce Colonization and Attenuate Gastritis in Helicobacter pylori–Infected Mice and Humans". Cancer Prevention Research 2: 353-360. DOI:10.1158/1940-6207.CAPR-08-0192. Research Blogging.
- ↑ (2008) "Determination of the absolute configuration of the glucosinolate methyl sulfoxide group reveals a stereospecific biosynthesis of the side chain". Phytochemistry 69: 2737-2742. DOI:10.1016/j.phytochem.2008.09.008. Research Blogging.