Alyssin (Synonyms: 5-Methylsulfinylpentyl isothiocyanate, 5-Methylsulfinylpentyl ITC)

Alyssin is an isothiocyanate that has been found in W. japonica and has diverse biological activities, including antibacterial, fungicidal, CYP inhibitory, and antiproliferative properties.^1,2,3 It is active against the bacteria B. subtilis, methicillin-sensitive S. aureus, methicillin-resistant S. aureus (MRSA), and E. coli, and the plant pathogenic fungus A. niger.¹ Alyssin (0.5-2.5 µM) directly inhibits activity of the cytochrome P450 (CYP) isoforms CYP1A1 and CYP1A2 induced by the polycyclic aromatic hydrocarbons (PAHs) anthracene and dibenzo[a,h]anthracene in MCF-7 breast cancer cells.² It inhibits proliferation of HCT116 colon cancer cells (IC₅₀ = <4 µM).³ Alyssin also inhibits platelet aggregation induced by ADP or arachidonic acid (IC₅₀s = 168 and 20 µM, respectively).⁴

1.Masuda, H., Harada, Y., Kishimoto, N., et al.Antimicrobial Activities of IsothiocyanatesAroma Active Compounds in Foods229-250(2001) 2.Skupinska, K., Misiewicz-Krzeminska, I., Lubelska, K., et al.The effect of isothiocyanates on CYP1A1 and CYP1A2 activities induced by polycyclic aromatic hydrocarbons in Mcf7 cellsToxicol. In Vitro23(5)763-771(2009) 3.Kim, M.J., Kim, S.H., and Lim, S.-J.Comparison of the apoptosis-inducing capability of sulforaphane analogues in human colon cancer cellsAnticancer Res.30(9)3611-3619(2010) 4.Morimitsu, Y., Hayashi, K., Nakagawa, Y., et al.Antiplatelet and anticancer isothiocyanates in Japanese domestic horseradish, WasabiMech. Ageing Dev.116(2-3)125-134(2000)