Sulforaphane ( Eng. Sulforaphane ) - an organic compound of plant origin with anti-cancer and antibacterial effects [1] [2] [3] . Sulforaphane is formed by hydrolysis from glucoraphanin, which is found in cabbage vegetables, such as broccoli , cabbage , cauliflower , kohlrabi , watercress , etc. [4] The broccoli and cauliflower sprouts are richest in glucoraphanin.
| Sulforaphane | |
|---|---|
 | |
 | |
| Are common | |
| Systematic name | 1-isothiocyanate-4-methylsulfinyl butane, 4-methylsulfinyl butyl isothiocyanate |
| Chem. formula | C 6 H 11 NOS 2 |
| Physical properties | |
| Molar mass | 177.29 g / mol |
| Classification | |
| Reg. CAS number | 4478-93-7 |
| PubChem | |
| Smiles | |
| Inchi | |
| Chebi | |
| ChemSpider | |
Education
Cabbage contains glucoraphanin, a sulforaphane precursor. When a plant is damaged (which happens, for example, when chewing), the plant enzyme myrosinase transforms glucoraphanin to sulforaphane, which is an antibacterial agent and participates in the plant defense system against infection.
| Glucoraphanin | → | (-) - ( R ) -Sulforaphane |
Bibliography
- Fimognari C., Lenzi M., Hrelia P. Interaction of the isothiocyanate sulforaphane with drug disposition and metabolism: pharmacological and toxicological implications (English) // Curr. Drug Metab. : journal. - 2008 .-- September ( vol. 9 , no. 7 ). - P. 668—678 . - PMID 18781917 .
- Zhang Y., Talalay P., Cho CG, Posner GH A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure (English) // Proceedings of the National Academy of Sciences of the United States of America : journal. - 1992 .-- March ( vol. 89 , no. 6 ). - P. 2399-2403 . - PMID 1549603 .
Notes
- ↑ Kensler, TW, Egner, PA, Agyeman, AS, Visvanathan, K., Groopman, JD, Chen, JG, ... & Talalay, P. (2012). Keap1 – nrf2 signaling: a target for cancer prevention by sulforaphane . In Natural Products in Cancer Prevention and Therapy (pp. 163-177). Springer, Berlin, Heidelberg.
- ↑ Juge, N., Mithen, RF, & Traka, M. (2007). Molecular basis for chemoprevention by sulforaphane: a comprehensive review . Cellular and Molecular Life Sciences, 64 (9), 1105.
- ↑ Moon JK, Kim JR, Ahn YJ, Shibamoto T (2010). Analysis and anti-Helicobacter activity of sulforaphane and related compounds present in broccoli (Brassica oleracea L.) sprouts. J. Agric. Food Chem. 58 (11): 6672–7. DOI : 10.1021 / jf1003573 . PMID 20459098 .
- ↑ Sivapalan, T., Melchini, A., Saha, S., Needs, PW, Traka, MH, Tapp, H., ... & Mithen, RF (2017). Bioavailability of Glucoraphanin and Sulforaphane From High ‐ Glucoraphanin Broccoli . Molecular nutrition & food research. https://doi.org/10.1002/mnfr.201700911