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Mesophotic coral ecosystems (MCEs) have complex but understudied biodiversity, especially for natural products discovery. Untargeted metabolomics research on 80 extracts prepared from marine sponge-associated fungi, half from shallow reefs (<30 m) and half from MCEs (30–150 m), facilitated prioritization for further study a  Cymostachys  fungus from a 103 m deep  Aaptos  sponge. LC-MS target-directed isolation yielded a series of new compounds, cymopolyphenols A−F ( 1 – 6 ), and two known phenylspirodrimanes, F1839-I ( 7 ) and stachybotrylactone ( 8 ). This is the first report of natural products from the recently described genus,  Cymostachys . Compounds  1 – 6  and  8  contain a dihydroisobenzofuran moiety, and  4 – 6  are low-order polymers of  1  with novel scaffolds. The structures of the compounds were established by spectroscopic and spectrometric data interpretation, with further support from X-ray crystallography studies of  3  and  4 . Compound  3  undergoes facile racemization in solution and was found to crystalize as a racemic mixture. Compound  5  was also obtained in racemic form, and after chiral chromatography, both separated enantiomers racemized in solution by a presumed keto-enol tautomerization. Compounds  1  and  3 – 6  were found to be weakly antimicrobial (MIC 16–64 μg/ml)  in vitro  against several Gram-positive and Gram-negative human or aquatic pathogens, compound  5  was shown to chelate iron  in vitro  at 10 μM, and  8  activated plant disease resistance  in vivo  in a transgenic model organism.

Discovery of Cymopolyphenols A–F From a Marine Mesophotic Zone Aaptos Sponge-Associated Fungus Cymostachys sp. NBUF082