One pair of new cyclopentaisochromenone enantiomer from Alternaria sp. TNXY-P-1 and their cytotoxic activity. Issue 4 (3rd April 2018)

• Record Type: Journal Article
• Authors: Lu, Xiao-Jie; Chen, Shao-Fei; Xu, Xiang-Wei; Zhao, Dan; Wang, Hai-Feng; Bai, Jiao; Hua, Hui-Ming; Chen, Gang; Pei, Yue-Hu
• Is Part Of: Journal of Asian natural products research. Volume 20:Issue 4(2018)
• Page Start: 328
• Page End: 336
• Publication Date: 2018-04-03
• Subjects: Cyclopentaisochromenone -- endophytic fungus -- Alternaria sp. -- cytotoxic activity; Materia medica -- Asia -- Periodicals; Pharmacognosy -- Asia -- Periodicals; Medicinal plants -- Asia -- Periodicals; Medicine, Oriental -- Asia -- Periodicals; 615.321095
• DOI: 10.1080/10286020.2017.1336164
• Languages: English
• ISSNs: 1028-6020

Abstract

Abstract: 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 analog2‒8, 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, compounds1a and1b were enantiomers separated from1 by chiral HPLC. The absolute configurations of1a and1b 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 μ M, respectively. Abstract :