Four new okaramine congeners, okaramines J. K. L and M. were isolated from okara fermented with Penicillium simplicissimum ATCC 90288, together with five biogenetically related compounds, cyclo (8a-(α,α ext{-dimethylally}))-L-Trp-8a-(α, α -dimethylallyl)-L-Trp), (N^8-(α,α cvelo dimethylallyl)-L-Trp-6a'-(α, α -dimethylallyl)-L-Trp), cyclo (L-Trp-L-Trp), cyclo (6a'-(α,α ext{-dimethylallyl})-L-Trp-L-Trp), and cyclo (N^8-(α,α -dimethylallyl)-L-Trp-L-Trp). Their structures were elucidated on the basis of spectroscopic methods. The new okaramines exhibited no insecticidal activity against silkworms.