Benzodiazepine Alkaloids from Marine‐Derived Endophytic Fungus Aspergillus ochraceus

Helvetica Chimica Acta
2009.0

Abstract

A new fungus-derived benzodiazepine analogue, 2-hydroxycircumdatin C (1), and a compound which has been isolated from a natural resource for the first time, but has been previously synthesized, namely (11aS)-2,3-dihydro-7-methoxy- 1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione (2), along with five structurally related known alkaloids (3-7), were isolated from Aspergillus ochraceus, an endophytic fungus derived from the marine brown alga Sargassum kjellmanianum. Their structures were established on the basis of spectroscopic methods. The absolute configuration of 1 was determined through CD evidence. Compound 1 displayed significant DPPH radical-scavenging activity with an IC50 value of 9.9 μM, which is 8.9-fold more potent than that of butylated hydroxytoluene (BHT), a well-known synthetic positive control. © 2009 Verlag Helvetica Chimica Acta AG.

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