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Bioactive metabolites from an endophytic Cryptosporiopsis sp. inhabiting Clidemia hirta

Zilla, Mahesh K., Qadri, Masroor, Pathania, Anup S., Strobel, Gary A., Nalli, Yedukondalu, Kumar, Sunil, Guru, Santosh K., Bhushan, Shashi, Singh, Sanjay K., Vishwakarma, Ram A., Riyaz-Ul-Hassan, Syed, Ali, Asif
Phytochemistry 2013 v.95 pp. 291-297
Bacillus cereus, Clidemia hirta, Cryptosporiopsis, Escherichia coli, Pseudomonas fluorescens, Staphylococcus aureus, cell cycle, culture media, cytotoxicity, endophytes, humans, inhibitory concentration 50, leukemia, pathogens, secondary metabolites, spectroscopy, stereochemistry
An endophytic Cryptosporiopsis sp. was isolated from Clidemia hirta and analyzed for its secondary metabolites that lead to the isolation of three bioactive molecules. The compounds were purified from the culture broth of the fungus and their structures were determined by spectroscopic methods as (R)-5-hydroxy-2-methylchroman-4-one (1), 1-(2,6-dihydroxyphenyl)pentan-1-one (2) and (Z)-1-(2-(2-butyryl-3-hydroxyphenoxy)-6-hydroxyphenyl)-3-hydroxybut-2-en-1-one (3). Compound 1 exhibited significant cytotoxic activity against the human leukemia cell line, HL-60 with an IC50 of 4μg/ml. This compound induced G2 arrest of the HL-60 cell cycle significantly. In addition, out of these compounds, 2 and 3 were active against several bacterial pathogens. Compound 2 was active against Bacillus cereus, Escherichia coli and Staphylococcus aureus with IC50 values varying from 18 to 30μg/ml, and compound 3 displayed activity against Pseudomonas fluorescens with an IC50 value of 6μg/ml. Compounds 2 and 3 are novel whereas compound 1 was reported earlier but the stereochemistry of its C-2 methyl is established for the first time.