Seven undescribed alkaloids, namely fischeramides A and B, 5,6-dimethoxycircumdatin C, 6-hydroxyacetylaszonalenin, 3-methoxyglyantrypine, 9-methoxyfumitremorgin C, and spirotryprostatin M, one undescribed natural product, namely 11-deacetyl pyripyropene A, together with nine known congeners, were isolated from the solid cultures of fungus Neosartorya fischeri, which was separated from a medicinal insect Cryptotympana atrata. Their structures were elucidated by extensive spectroscopic data, electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analyses. Structurally, fischeramides A and B represented a pair of rare geometric isomers of the benzodiazepinedione derivatives with a highly conjugated feature. Fischeramide A showed potential immunosuppressive activity in LPS and anti-CD3/anti-CD28 mAbs activated murine splenocytes proliferation with IC50 values of 7.08 and 6.31 μM, respectively, and also showed anti-inflammatory activity against the lipopolysaccharide-induced nitric oxide production with an IC50 value of 25 ± 1 μM. In addition, 5,6-dimethoxycircumdatin C showed remarkable antibacterial activity against ESBL-producing E. coli with an MIC value of 2.0 μg/mL.