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Chemical analysis of an M1 agar plate cultivation of a marine fish-gut-derived fungus, Chrysosporium sp. CMB-F214, revealed the known chrysosporazines A-D ( 11 - 14 ) in addition to a suite of very minor aza analogues 1 - 6 . A microbioreactor (MATRIX) cultivation profiling analysis failed to deliver cultivation conditions that significantly improved the yields of 1 - 6 ; however, it did reveal that M2 agar cultivation produced the new natural product 15 . A precursor-directed biosynthesis strategy adopting supplementation of a CMB-F214 M1 solid agar culture with sodium nicotinate enhanced production of otherwise inaccessible azachrysposorazines A1 ( 1 ), A2 ( 2 ), B1 ( 3 ), C1 ( 4 ), C2 ( 5 ) and D1 ( 6 ), in addition to four new chrysosporazines; chrysosporazines N-P ( 7 - 9 ) and spirochrysosporazine A ( 10 ). Structures inclusive of absolute configurations were assigned to 1 - 15 based on detailed spectroscopic and chemical analyses, and biosynthetic considerations. Non-cytotoxic to human carcinoma cells, azachrysosporazies 1 - 5 were capable of reversing doxorubicin resistance in P-glycoprotein (P-gp)-overexpressing human colon carcinoma cells (SW620 Ad300), with optimum activity exhibited by the C-2' substituted analogues 3 - 5 .

marine drugs

Precursor-Directed Biosynthesis Mediated Amplification of Minor Aza Phenylpropanoid Piperazines in an Australian Marine Fish-Gut-Derived Fungus, Chrysosporium sp. CMB-F214