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A chemical study of the EtOAc extract of  Nemania bipapillata  (AT-05), an endophytic fungus isolated from the marine red alga  Asparagopsis taxiformis  -  Falkenbergia  stage, led to the isolation of five new botryane sesquiterpenes, including the diastereomeric pair (+)-(2 R ,4 S ,5 R ,8 S )-( 1 ) and (+)-(2 R ,4 R ,5 R ,8 S )-4-deacetyl-5-hydroxy-botryenalol ( 2 ), (+)-(2 R ,4 S ,5 R ,8 R )-4-deacetyl-botryenalol ( 3 ), one pair of diastereomeric botryane  nor sesquiterpenes bearing an unprecedented degraded carbon skeleton, (+)-(2 R ,4 R ,8 R )-( 4 ) and (+)-(2 R ,4 S ,8 S )-( 5 ), which were named nemenonediol A and nemenonediol B, respectively, in addition to the known 4β-acetoxy-9β,10β,15α-trihydroxyprobotrydial ( 6 ). Their structures were elucidated using 1D and 2D NMR, HRESIMS and comparison with literature data of similar known compounds. The absolute configurations of  2 ,  3  and  4  were deduced by comparison of experimental and calculated electronic circular dichroism (ECD) spectra, while those of  1  and  5  were assigned from vibrational circular dichroism (VCD) data. Compound  4  weakly inhibited acetylcholinesterase, whereas compound  1  inhibited both acetylcholinesterase and butyrylcholinesterase. Compounds  1 ,  3 ,  5  and  6  were tested against two carcinoma cell lines (MCF-7 and HCT-116), but showed no significant citotoxicity at tested concentrations (IC 50  > 50 µM).

Botryane terpenoids produced by Nemania bipapillata, an endophytic fungus isolated from red alga Asparagopsis taxiformis - Falkenbergia stage