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Benzodiazepine Alkaloids from Marine‐Derived Endophytic Fungus Aspergillus ochraceus
Author(s) -
Cui ChuanMing,
Li XiaoMing,
Li ChunShun,
Sun HaoFen,
Gao ShuShan,
Wang BinGui
Publication year - 2009
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200900084
Subject(s) - chemistry , aspergillus ochraceus , fungus , butylated hydroxytoluene , stereochemistry , dpph , aspergillus , alkaloid , botany , organic chemistry , antioxidant , food science , mycotoxin , ochratoxin a , biology
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 (11a S )‐2,3‐dihydro‐7‐methoxy‐1 H ‐pyrrolo[2,1‐ c ][1,4]benzodiazepine‐5,11(10 H ,11a H )‐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 IC 50 value of 9.9 μ M , which is 8.9‐fold more potent than that of butylated hydroxytoluene (BHT), a well‐known synthetic positive control.