Cercosporin

Cercosporin is a pigmented phytotoxin isolated from the fungus C. kikuchii that produces reactive oxygen species in plant hosts leading to cellular damage.^1,2 It exhibits light-activated cytotoxic effects in vitro with cytotoxic concentration (CC₅₀) values of 241, 282, and 174 nM in HeLa, A432, and MCF-7 cells, respectively.³ It is a selective inhibitor of PKC (IC₅₀ = 600-1,300 nM) with no activity on PKA or PPK at concentrations over 180 µM.⁴

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1. Shimpei, K., and Tamura, T. Cercosporin. A pigment of Cevcosporina kikuchii mafsumofo et tomoyasu. I. Cultivation of fungus, isolation and purification of pigment. J. Am. Chem. Soc. 79(21), 5725-5726 (1957).

2. Williamson, J.D., and Scandalios, J.G. Plant antioxidant gene responses to fungal pathogens. Trends. Microbiol. 1(6), 239-245 (1993).

3. Vandenbogaerde, A.L., Delaey, E.M., Vantieghem, A.M., et al. Cytotoxicity and antiproliferative effect of hypericin and derivatives after photosensitization. Photochem. Photobiol. 67(1), 119-125 (1998).

4. Morgan, B.J., Dey, S., Johnson, S.W., et al. Design, synthesis, and investigation of protein kinase C inhibitors: Total syntheses of (+)-calphostin D, (+)-phleichrome, cercosporin, and new photoactive perylenequinones. J. Am. Chem. Soc. 131(26), 9413-9425 (2009).