8H,10H-7a,12a-(Iminomethano)indolizino[6,7-h]pyrano[3,2-a]carbazole-8,16-dione, 3,11,12,13,13a,14-hexahydro-3,3,14,14-tetramethyl-, 15-oxide, (7aS,12aS,13aS)-

Avrainvillamide is a fungal metabolite and monomeric form of stephacidin B that has been found in A. ochraceus.1,2 It is active against S. aureus, S. pyogenes, and E. faecalis (MICs = 12.5, 12.5, and 25 μg/ml, respectively).2 Avrainvillamide inhibits the growth of LNCaP, BT-549, T47D, and MALME-3M cancer cells with GI50 values of 0.24, 0.62, 0.21, and 0.41 μM, respectively.1

1.Wulff, J.E., Herzon, S.B., Siegrist, R., et al.Evidence for the rapid conversion of stephacidin B into the electrophilic monomer avrainvillamide in cell cultureJ. Am. Chem. Soc.129(16)4898-4899(2007) 2.Sugie, Y., Hirai, H., Inagaki, T., et al.A new antibiotic CJ-17,665 from Aspergillus ochraceusJ. Antibiot.54(11)911-916(2001)