AbstractThe importance of microbial natural products has been widely demonstrated in the search for new antibiotics. However, the functional role of microbial metabolites in nature remains to be deciphered. Several natural products are known to mediate microbial interactions through metabolic exchange. One approach to investigate metabolic exchange in the laboratory is through microbial interactions. Here, we describe the chemical study of selected endophytes isolated from the Brazilian medicinal plant Lychnophora ericoides by pairwise inter-kingdom interactions in order to correlate the impact of co-cultivation to their metabolic profiles. Combining mass spectrometry tools and NMR analyses, a total of 29 compounds were identified. These compounds are members of polyene macrocycles, pyrroloindole alkaloids, angucyclines, and leupeptins chemical families. Two of the identified compounds correspond to a new fungal metabolite (29) and a new actinobacterial angucycline-derivative (23). Our results revealed a substantial arsenal of small molecules induced by microbial interactions, as we begin to unravel the complexity of microbial interactions associated with endophytic systems.