The cryptic metabolites and anti-phytopathogenic activities from Nigrospora lacticolonia and Penicillium rubens uncovered by the synergism with host Paris polyphylla, monoculture, and co-culture.

[Display omitted] • Host Paris polyphylla medium, and coculture led to seventeen novel metabolites. • Nine cryptic compounds were produced by the inductions of host medium and coculture. • The antiphytopathogenic activities of all compounds were investigated. • Antifungal metabolites showed the chemical interaction of the endophytes, and host. The synergism of host Paris polyphylla medium, the monoculture, and the coculture led to seventeen new metabolites, including eight sesquiterpenes, 1 – 7 having uncommon structural motifs compared to similar caryophyllene derivatives, 8 with an unprecedented bicyclic framework, and three xyloketals (13 – 15) with unprecedented frameworks from Nigrospora lacticolonia ; one polyketide, 17 with novel bicyclo [2.2.2] undecane skeleton, and five polyketide-terpenoid hybrids, 20 (one novel sulfated), 21 – 24 from Penicillium rubens. The structures were determined mainly by the NMR, HRESIMS, ECD calculation, and single-crystal X-ray diffraction. Nine cryptic compounds (2 – 4 , 5 , 12 – 15, 17) were produced by the inductions of host medium and the coculture. The compounds 13 from N. lacticolonia , 24 – 26 , 28 , 29 , and 31 from P. rubens indicated significant antiphytopathogenic activities against N. lacticolonia with MICs at 2–4 μg/mL. Moreover, compounds 22 – 26 , 28 , 29 , and 31 from P. rubens showed antifungal activities against P. rubens with MICs at 2–4 μg/mL. The synergistic effects of host medium and the coculture can induce the structural diversity of metabolites. [ABSTRACT FROM AUTHOR]