Raphanin

Raphanin
Names
IUPAC name
4-Isothiocyanato-1-(methylsulfinyl)but-1-ene
Other names
Sulforaphen; Sulforaphene; Sativin
Identifiers
592-95-0 YesY
3D model (Jmol) Interactive image
ChemSpider 16736047
PubChem 6433206
Properties
C6H9NOS2
Molar mass 175.26 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Raphanin is the main sulfur component found in radish seeds of Raphanus sativus and is also found in broccoli and red cabbage.[1][2] It was first described by G. Ivanovics and S. Horvath in 1947.[3][4] Raphanin inhibits activity of viruses, some fungi and various bacteria including Staphylococus, Streptococus, Pneumococcus and Escherichia coli (see table). The effect is stronger against Gram-positive than Gram-negative bacteria and against DNA than RNA viruses; it is suppressed by serum and by sulfur compounds such as hydrogen sulfide, mercaptoacetic acid, cystine and glutathione.[3][5][6][7][8] The antibacterial, antifungal and antiviral effects from consuming radishes were recognized in traditional Chinese medicine.[9] Given that Raphanin can be chiefly responsible for keeping the production of thyroxine and calcitonin in normal balance, in Russia, radishes have long been used for treating both types of thyroid problems.[10] However, in the abstract to his 1947 paper, Ivanovics noted that because raphanin is highly toxic, it did not "hold the promise of a useful therapeutic agent".[11]

Minimum inhibitory concentration of raphanin[6]
Bacteria MIC (mg/mL)
Staphylococus0.04
Shigella dysenteriae0.125
Salmonella typhi0.125
Escherichia coli0.2

See also

References

  1. ↑ Sinha, Nirmal K.; Hui, Y. H.; Muhammad Siddiq; Jasim Ahmed (2010). Handbook of Vegetables and Vegetable Processing. John Wiley and Sons. p. 156. ISBN 978-0-8138-1541-1.
  2. ↑ Michael Meyer & Sieghard T. Adam. "Comparison of glucosinolate levels in commercial broccoli and red cabbage from conventional and ecological farming". European Food Research and Technology. 226 (6): 1429–1437. doi:10.1007/s00217-007-0674-0.
  3. 1 2 Baron, Abraham Louis (1950). Handbook of antibiotics. Reinhold. p. 215.
  4. ↑ Ivãnovics, G. & S. Horvãth (1947). "Raphanin, an Antibacterial Principle of the Radish (Raphanus sativus)". Nature. 160 (4061): 297–298. doi:10.1038/160297a0. PMID 20261763.
  5. ↑ Florey, Howard (1949). Antibiotics: a survey of penicillin, streptomycin, and other antimicrobial substances from fungi, actinomycetes, bacteria, and plants. Oxford University Press. pp. 625–6.
  6. 1 2 Chang, Hson-Mou; Pui-Hay, Paul; Yao, Sih-Cheng (2001). Pharmacology and Applications of Chinese Material Medical. World Scientific. p. 969. ISBN 978-981-02-3694-6.
  7. ↑ Acta microbiologica Academiae Scientiarum Hungaricae. Magyar Tudományos Akadémia. 1968. pp. 311–3.
  8. ↑ Summers, Sean (2007). World History on Satan's Diet. Wheatmark, Inc. p. 4. ISBN 978-1-58736-806-6.
  9. ↑ Hu, Shiu-ying (2005). Food plants of China. Chinese University Press. p. 132. ISBN 978-962-996-229-6.
  10. ↑ "Radishes". Natural Pedia. Retrieved 4 September 2011.
  11. ↑ Ivànovics, G. & Horvath, S. (1947). "Isolation and Properties of Raphanin, an Antibacterial Substance from Radish Seed". Experimental Biology and Medicine. 66 (3): 625–630. doi:10.3181/00379727-66-16177. PMID 18900045.
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