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Six new epipolythiodioxopiperazine (ETP) alkaloids, penicisulfuranols A-F (1-6), were isolated from the mangrove endophytic fungus Penicillium janthinellum HDN13-309. All structures including absolute configurations were elucidated on the basis of comprehensive spectroscopic data and ECD calculations. They belong to the unusual family of ETPs containing sulfur atoms on both α- and β-positions of amino acid residues and a rare 1,2-oxazadecaline core moiety. In addition, compounds 1-6 also possess a rare spiro-furan ring and 1-3 showed cytotoxicity with IC values ranging from 0.1 to 3.9 μM.

Neosartoryadins A (1) and B (2), both with a unique 6/6/6/5 quinazoline ring system connected directly to a 6/5/5 imidazoindolone ring, together with three biogenetically related compounds 3-5, were isolated from the endophytic fungus Neosartorya udagawae HDN13-313. The absolute configurations of new compounds 1-4 were established. Compounds 1 and 2 displayed anti-influenza virus A (H1N1) activities with IC50 values of 66 and 58 μM, respectively (ribavirin as positive control, IC50 = 94 μM).

Four new alkyl aromatics, penixylarins A–D (1–4), along with the known biogenetically related 1,3-dihydroxy-5-(12-hydroxyheptadecyl)­benzene (5) and 1,3-dihydroxy-5-(12-sulfoxyheptadecyl)­benzene (6), were isolated from a mixed culture of the Antarctic deep-sea-derived fungus Penicillium crustosum PRB-2 and the mangrove-derived fungus Xylaria sp. HDN13-249. UPLC-MS data and an analysis of structural features showed that compounds 1 and 2 were produced by collaboration of the two fungi, while compounds 3–6 could be produced by Xylaria sp. HDN13-249 alone, but in noticeably increased quantities by cocultivation. Compounds 2, 3, 5, and 6 showed antibacterial activity against a panel of strains, and compound 3 possessed potential antituberculosis effects (MIC = 6.25 μM against Mycobacterium phlei).

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