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A systematic chemical exploration of the marine-derived fungus  Penicillium janthinellum  led to the isolation of four indole-diterpenoid derivatives ( 1 – 4 ), including new penijanthines C and D ( 1  and  2 ), and a pair of new steroidal epimers, penijanthoids A and B ( 5  and  6 ). The calculated ECD spectra and Snatzke's method for the new compound  1  were carried out to determine its absolute configuration. The absolute configuration of  3  was established by X-ray diffraction and calculated ECD methods for the first time. DP4plus approach was used to elucidate the absolute configurations of the C-25 epimeric steroids  5  and  6 . 25-Epimeric  5  and  6  represent the first examples of steroids forming a five-membered lactone between C-23 and C-27 from marine fungi. Compounds  1 ,  2 ,  5 , and  6  displayed significant anti- Vibrio  activity (Minimum inhibitory concentration, MIC values ranging from 3.1 to 50.0 μM) against three pathogenic  Vibrio  spp.

Anti-Vibrio Indole-Diterpenoids and C-25 Epimeric Steroids From the Marine-Derived Fungus Penicillium janthinellum