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Bioactive Alkaloids from Indole‐3‐carbinol Exposed Culture of Daldiniaeschscholzii
Author(s) -
Lin Li Ping,
Tan Ren Xiang
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201800160
Subject(s) - chemistry , oxindole , indole test , circular dichroism , stereochemistry , antimicrobial , quantum chemical , lactam , combinatorial chemistry , organic chemistry , molecule , catalysis
Two new and rare bioactive indoles named dalesindoloids A ( 1 ) and B ( 3 ), along with 3‐(1 H ‐indole‐3ylmethyl)‐2‐oxindole ( 2 ), were characterized from the indole‐3‐carbinol (I3C)‐exposed culture of Daldinia eschscholzii . The absolute configuration of 2 was determined by quantum chemical calculations of the electronic circular dichroism (ECD) spectrum. Dalesindoloids A and B were cytotoxic against the leukemia HL‐60 cell line with the IC 50 values of 1.0 and 7.4 μmol/L, respectively, with the former being inhibitory on Staphylococcus aureus (MIC: 9.1 μmol/L). The simultaneous characterization of the alkaloids from the I3C‐exposed fungal culture highlighted that the 2,3‐epoxyindoline motif can be transformed into both lactam and indolin‐3‐one moieties. This is the first‐time description of the 2,3‐epoxyindoline chemical versatility and Wagner‐Meerwein rearrangement (WMR) reaction in the microbial culture.