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Raphanin

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Raphanin
Names
IUPAC name
4-Isothiocyanato-1-(methylsulfinyl)but-1-ene
Other names
Sulforaphen; Sulforaphene; Sativin
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C6H9NOS2/c1-10(8)5-3-2-4-7-6-9/h3,5H,2,4H2,1H3
    Key: QKGJFQMGPDVOQE-UHFFFAOYSA-N
  • InChI=1/C6H9NOS2/c1-10(8)5-3-2-4-7-6-9/h3,5H,2,4H2,1H3
    Key: QKGJFQMGPDVOQE-UHFFFAOYAU
  • S=C=N/CC\C=C\S(=O)C
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).

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 (most likely Epstein–Barr_virus), some fungi and various bacteria including Staphylococcus, Streptococcus, 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] 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".[10]

Minimum inhibitory concentration of raphanin[6]
Bacteria MIC (mg/mL)
Staphylococcus 0.04
Shigella dysenteriae 0.125
Salmonella typhi 0.125
Escherichia coli 0.2

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. {{cite journal}}: Unknown parameter |lastauthoramp= ignored (|name-list-style= suggested) (help)
  3. ^ a b 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. {{cite journal}}: Unknown parameter |lastauthoramp= ignored (|name-list-style= suggested) (help)
  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. ^ a b 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. ^ 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. {{cite journal}}: Unknown parameter |lastauthoramp= ignored (|name-list-style= suggested) (help)

External links

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