Three pairs of variecolortide enantiomers from Eurotium sp. with caspase-3 inhibitory activity

Fitoterapia

Volumn 92, Issue , 2014, Pages 252-259

  Chen, Guo Dong ^a,d   Bao, Yan Ru ^a   Huang, Yuan Fan ^a   Hu, Dan ^a   Li, Xiao Xia ^a   Guo, Liang Dong ^b   Li, Jia ^c   Yao, Xin Sheng ^a   Gao, Hao ^a  

^a JINAN UNIVERSITY   (China)

^b INSTITUTE OF MICROBIOLOGY   (China)

^c SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^d SOUTH CHINA AGRICULTURAL UNIVERSITY   (China)

Author keywords

Caspase 3 inhibitor; Eurotium sp.; Variecolortides

Indexed keywords

7 O METHYLVARIECOLORTIDE A; ANTHRAQUINONE DERIVATIVE; CASPASE 3; CASPASE 3 INHIBITOR; PIPERAZINEDIONE; UNCLASSIFIED DRUG; VARIECOLORTIDE B; VARIECOLORTIDE C;

ARTICLE; BIOSYNTHESIS; CHEMICAL STRUCTURE; CHIRAL CHROMATOGRAPHY; CIRCULAR DICHROISM; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; DRUG ISOLATION; ENANTIOMER; ENZYME ASSAY; ENZYME INHIBITION; EUROTIUM; FUNGAL STRAIN; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IC 50; NONHUMAN; PRIORITY JOURNAL;

CASPASE-3 INHIBITOR; EUROTIUM SP.; VARIECOLORTIDES;

ANTHRACENES; BIOLOGICAL PRODUCTS; CASPASE 3; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIKETOPIPERAZINES; ENZYME INHIBITORS; EUROTIUM; INDOLE ALKALOIDS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; PIPERAZINES; STEREOISOMERISM;

EID: 84890963721     PISSN: 0367326X     EISSN: 18736971     Source Type: Journal    
DOI: 10.1016/j.fitote.2013.11.012     Document Type: Article

References (20)

1. W.L. Wang, T.J. Zhu, H.W. Tao, Z.Y. Lu, Y.C. Fang, and Q.Q. Gu et al. Three novel, structurally unique spirocyclic alkaloids from the halotolerant B-17 fungal strain of Aspergillus variecolor Chem Biodivers 4 2007 2913 2919
2. D.L. Li, X.M. Li, P. Proksch, and B.G. Wang 7-O-methylvariecolortide A, a new spirocyclic diketopiperazine alkaloid from a marine mangrove derived endophytic fungus, Eurotium rubrum Nat Prod Commun 5 2010 1583 1586
3. C.A. Kuttruff, H. Zipse, and D. Trauner Concise total syntheses of variecolortides A and B through an unusual hetero-Diels-Alder reaction Angew Chem Int Ed 50 2011 1402 1405
4. C.A. Kuttruff, P. Mayer, and D. Trauner Evolution of a synthetic strategy for the variecolortides Eur J Org Chem 2012 5151 5161
5. G.D. Chen, H. Gao, J.S. Tang, Y.F. Huang, Y. Chen, and Y. Wang et al. Benzamides and quinazolines isolated from a mangrove actinomycetes Streptomyces sp. (No. 061316) with inhibiting caspase-3 catalytic activity in vitro Chem Pharm Bull 59 2011 447 451
6. G.D. Chen, Y.J. Li, H. Gao, Y. Chen, X.X. Li, and J. Li et al. New azaphilones and chlorinated phenolic glycosides from Chaetomium elatum with caspase-3 inhibitory activity Planta Med 78 2012 1683 1689
7. G.D. Chen, Y. Chen, H. Gao, L.Q. Shen, Y. Wu, and X.X. Li et al. Xanthoquinodins from the endolichenic fungal strain Chaetomium elatum J Nat Prod 76 2013 702 709
8. J.Q. Du, J. Wu, H.J. Zhang, Y.H. Zhang, B.Y. Qiu, and F. Wu et al. Isoquinoline-1,3,4-trione derivatives inactivate caspase-3 by generation of reactive oxygen species J Biol Chem 283 2008 30205 30215
9. I. Okun, S. Malarchuk, E. Dubrovskaya, A. Khvat, S. Tkachenko, and V. Kysil et al. Screening for caspase-3 inhibitors: effect of a reducing agent on identified hit chemotypes J Biomol Screen 11 2006 694 703 (Pubitemid 44315967)
10. Y.H. Zhang, H.J. Zhang, F.W. Wu, Y.H. Chen, X.Q. Ma, and J.Q. Du et al. Isoquinoline-1,3,4-trione and its derivatives attenuate β-amyloid-induced apoptosis of neuronal cells FEBS J 273 2006 4842 4852
11. N. Morooka, S. Nakano, N. Itoi, and Y. Ueno The chemical structure and the mutagenicity of emodin metabolites Agric Biol Chem 54 1999 1247 1252
12. H. Fujimoto, T. Fujimaki, E. Okuyama, and M. Yamazaki Immunomodulatory constituents from an ascomycete, Microascus tardifaciens Chem Pharm Bull 47 1999 1426 1432 (Pubitemid 29510311)
13. Y. Li, X. Li, S.K. Kim, J.S. Kang, H.D. Choi, and J.R. Rho et al. Golmaenone, a new diketopiperazine alkaloid from the marine-derived fungus Aspergillus sp. Chem Pharm Bull 52 2004 375 376 (Pubitemid 41685543)
14. 13C NMR spectra and stereochemistry of isoechinulins A, B and C Agric Biol Chem 43 1979 1759 1763 (Pubitemid 11254365)
15. D.L. Li, X.M. Li, T.G. Li, H.Y. Dang, and B.G. Wang Dioxopiperazine alkaloids produced by the marine mangrove derived endophytic fungus Eurotium rubrum Helv Chim Acta 91 2008 1888 1893
16. H.J. Zhu Modern organic stereochemistry 2009 Science Presses Beijing
17. J. Ren, J.X. Jiang, L.B. Li, T.G. Liao, R.R. Tian, and X.L. Chen et al. Assignment of the absolute configuration of concentricolide - absolute configuration determination of its bioactive analogs using DFT methods Eur J Org Chem 23 2009 3987 3991
18. X.N. Li, Y. Zhang, X.H. Cai, T. Feng, Y.P. Liu, and Y. Li et al. Psychotripine: a new trimeric pyrroloindoline derivative from Psychotria pilifera Org Lett 13 2011 5896 5899
19. S.D. Zhao, L. Shen, D.Q. Luo, and H.J. Zhu Progression of absolute configuration determination in natural product chemistry using optical rotation (dispersion), matrix determinant and electronic circular dichroism methods Curr Org Chem 15 2011 1843 1862
20. F. Fülöp, K. Pihlaja, K. Pihlaja, and G. Bernath Ring-chain tautomerism in 1,3-oxazines J Org Chem 52 1987 3821 3825