Bioactive Metabolites from Mangrove Endophytic Fungus Aspergillus sp. 16-5B.

作者: Yayue Liu , Senhua Chen , Zhaoming Liu , Yongjun Lu , Guoping Xia

DOI: 10.3390/MD13053091

关键词: IsocoumarinIC50StereochemistryAspergillusAlpha-glucosidaseCircular dichroismNon-competitive inhibitionBiologyAbsolute configurationTwo-dimensional nuclear magnetic resonance spectroscopy

摘要: Chemical investigation of the endophytic fungus Aspergillus sp. 16-5B cultured on Czapek’s medium led to isolation four new metabolites, aspergifuranone (1), isocoumarin derivatives (±) 2 and 3, (R)-3-demethylpurpurester A (4), together with known purpurester B (5) pestaphthalides (6). Their structures were determined by analysis 1D 2D NMR spectroscopic data. The absolute configuration Compound 1 was comparison experimental calculated electronic circular dichroism (ECD) spectra, that 4 revealed comparing its optical rotation data CD those literature. structure 6 further confirmed single-crystal X-ray diffraction experiment using CuKα radiation. All isolated compounds evaluated for their α-glucosidase inhibitory activities, showed significant activity IC50 value 9.05 ± 0.60 μM. Kinetic a noncompetitive inhibitor α-glucosidase. Compounds exhibited moderate activities.

参考文章(22)
Zhaoming Liu, Guoping Xia, Senhua Chen, Yayue Liu, Hanxiang Li, Zhigang She, Eurothiocin A and B, Sulfur-Containing Benzofurans from a Soft Coral-Derived Fungus Eurotium rubrum SH-823 Marine Drugs. ,vol. 12, pp. 3669- 3680 ,(2014) , 10.3390/MD12063669
Zhi-yun Du, Rong-rong Liu, Wei-yan Shao, Xue-pu Mao, Lin Ma, Lian-quan Gu, Zhi-shu Huang, Albert S.C. Chan, α-Glucosidase inhibition of natural curcuminoids and curcumin analogs European Journal of Medicinal Chemistry. ,vol. 41, pp. 213- 218 ,(2006) , 10.1016/J.EJMECH.2005.10.012
Jie Ren, Ju-Xing Jiang, Liang-Bo Li, Tou-Geng Liao, Ren-Rong Tian, Xu-lin Chen, Si-Ping Jiang, Charles U. Pittman, Hua-Jie Zhu, Assignment of the Absolute Configuration of Concentricolide – Absolute Configuration Determination of Its Bioactive Analogs Using DFT Methods European Journal of Organic Chemistry. ,vol. 2009, pp. 3987- 3991 ,(2009) , 10.1002/EJOC.200900422
Fernando Brindis, Rogelio Rodríguez, Robert Bye, Martín González-Andrade, Rachel Mata, (Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor. Journal of Natural Products. ,vol. 74, pp. 314- 320 ,(2011) , 10.1021/NP100447A
Hanxiang Li, Hongbo Huang, Changlun Shao, Huarong Huang, Jieyi Jiang, Xun Zhu, Yayue Liu, Lan Liu, Yongjun Lu, Mengfeng Li, Yongcheng Lin, Zhigang She, Cytotoxic norsesquiterpene peroxides from the endophytic fungus Talaromyces flavus isolated from the mangrove plant Sonneratia apetala. Journal of Natural Products. ,vol. 74, pp. 1230- 1235 ,(2011) , 10.1021/NP200164K
Ze’en Xiao, Huarong Huang, Changlun Shao, Xuekui Xia, Lin Ma, Xishan Huang, Yongjun Lu, Yongcheng Lin, Yuhua Long, Zhigang She, Asperterpenols A and B, new sesterterpenoids isolated from a mangrove endophytic fungus Aspergillus sp. 085242. Organic Letters. ,vol. 15, pp. 2522- 2525 ,(2013) , 10.1021/OL401005J
David J. Newman, Gordon M. Cragg, Natural Products As Sources of New Drugs over the 30 Years from 1981 to 2010 Journal of Natural Products. ,vol. 75, pp. 311- 335 ,(2012) , 10.1021/NP200906S
Hui Wang, Yi Wang, Wei Wang, Peng Fu, Peipei Liu, Weiming Zhu, Anti-influenza virus polyketides from the acid-tolerant fungus Penicillium purpurogenum JS03-21. Journal of Natural Products. ,vol. 74, pp. 2014- 2018 ,(2011) , 10.1021/NP2004769
H. D. Flack, G. Bernardinelli, The use of X-ray crystallography to determine absolute configuration. Chirality. ,vol. 20, pp. 681- 690 ,(2008) , 10.1002/CHIR.20473
Xuekui Xia, Jun Qi, Yayue Liu, Airong Jia, Yonggang Zhang, Changheng Liu, Cuiling Gao, Zhigang She, Bioactive Isopimarane Diterpenes from the Fungus, Epicoccum sp. HS-1, Associated with Apostichopus japonicus Marine Drugs. ,vol. 13, pp. 1124- 1132 ,(2015) , 10.3390/MD13031124