One pair of new cyclopentaisochromenone enantiomer from Alternaria sp. TNXY-P-1 and their cytotoxic activity
| Autor: | Dan Zhao, Hai-Feng Wang, Hui-Ming Hua, Yue-Hu Pei, Jiao Bai, Gang Chen, Shao-Fei Chen, Xiao-Jie Lu, Xiang-Wei Xu |
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| Rok vydání: | 2017 |
| Předmět: |
Stereochemistry
Pharmaceutical Science Antineoplastic Agents HL-60 Cells Biology 01 natural sciences Analytical Chemistry Lactones Alternaria sp Drug Discovery Cytotoxic T cell Humans Benzopyrans Nuclear Magnetic Resonance Biomolecular Pharmacology Quantum chemical Molecular Structure 010405 organic chemistry Organic Chemistry Alternaria Stereoisomerism General Medicine Endophytic fungus Arisaema 0104 chemical sciences Chiral column chromatography 010404 medicinal & biomolecular chemistry Complementary and alternative medicine Cell culture Molecular Medicine Enantiomer Drug Screening Assays Antitumor Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Journal of Asian natural products research. 20(4) |
| ISSN: | 1477-2213 |
| Popis: | One pair of new cyclopentaisochromenone derivatives, (+)-(S)-6-hydroxy-1,8-dimethoxy-3a-methyl-3,3a-dihydrocyclopenta[c]isochromene-2,5-dione (1a) and (-)-(R)-6-hydroxy-1,8-dimethoxy-3a-methyl-3,3a-dihydrocyclopenta[c]isochromene-2,5-dione (1b), together with seven known analog 2‒8, were isolated from a rice solid culture of the endophytic fungus Alternaria sp. TNXY-P-1, obtained from fresh leaf of Arisaema heterophyllum. Their structures were elucidated on the basis of detailed 1D, 2D NMR, and HRESIMS analysis. Among them, compounds 1a and 1b were enantiomers separated from 1 by chiral HPLC. The absolute configurations of 1a and 1b were assigned by quantum chemical calculations of the electronic circular dichroic spectra. All isolated compounds were evaluated for cytotoxic activities. Interestingly, enantiomers (+)-1a and (−)-1b showed distinct selective antitumor activities against HL-60 cell lines with IC50 values of >200, 75.3 μM, respectively. |
| Databáze: | OpenAIRE |
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