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Seven pairs of new oxygenated aplysinopsin-type enantiomers, (+)- and (−)-oxoaplysinopsins A‒G ( 1 ‒ 7 ), two new bromotyrosine-derived alkaloids, subereamollines C and D ( 18  and  19 ), together with ten known compounds ( 8 ‒ 17 ) were isolated from the Xisha Islands sponge  Fascaplysinopsis reticulata . The planar structures were determined by extensive NMR and MS spectroscopic data. Each of the optically pure enantiomers was achieved by chiral HPLC separation. The absolute configurations were assigned by the quantum chemical calculation methods. Compound  19  showed cytotoxicity against Jurkat cell lines with IC 50  value of 0.88 μM. Compounds  2 ,  16  and  17  showed tyrosine phosphatase 1B (PTP1B) inhibition activity with IC 50  value ranging from 7.67 to 26.5 μM, stronger than the positive control of acarbose and 1-deoxynojirimycin. A structural activity relationship for the aplysinopsin-type enantiomers were observed in PTP1B inhibition activity of  2  and cytotoxicity of  3  that the dextrorotary (+) -2  and (+) -3  showed stronger activity than the levorotary (−) -2  and (−) -3 .

Aplysinopsin-type and Bromotyrosine-derived Alkaloids from the South China Sea Sponge Fascaplysinopsis reticulata