New Naphthoquinone Terpenoids from Marine Actinobacterium, Streptomyces sp. CNQ-509.

A member of the marine streptomycete clade MAR4, sp. CNQ-509, has genetic potential for the biosynthesis of hybrid isoprenoids and produces several meroterpenoids such as naphterpin, nitropyrrolin and marinophenazine. Our research on the strain CNQ-509 led to the isolation of two new naphterpin derivatives ( and ) comprised of naphthoquinone and geranyl moieties along with the known terpenoid, debromomarinone. The two-dimensional structure of these compounds was determined through spectral data analysis using data from NMR, MS and UV spectroscopy. Furthermore, the full structures of and including absolute configurations were unequivocally established by a combination of NMR experiments and chemical modifications.