Identification and biological evaluation of secondary metabolites from the endolichenic fungus aspergillus versicolor

Chemistry and Biodiversity

Volumn 12, Issue 4, 2015, Pages 575-592

  Li, Xiao Bin ^a   Zhou, Yan Hui ^a   Zhu, Rong Xiu ^a   Chang, Wen Qiang ^a   Yuan, Hui Qing ^a   Gao, Wei ^b   Zhang, Lu Lu ^b   Zhao, Zun Tian ^b   Lou, Hong Xiang ^a  

^a SHANDONG UNIVERSITY   (China)

^b SHANDONG NORMAL UNIVERSITY   (China)

Author keywords

Antifungal activity; Aspergillus versicolor; Bisabolane sesquiterpenoid; Cytotoxic activity; Endolichenic fungus; Fungi; Sesquiterpenoids

Indexed keywords

(7,10) 10 HYDROXYSYDOWIC ACID; (7,10) ISO 10 HYDROXYSYDOWIC ACID; (7,8) 8 HYDROXYSYDOWIC ACID; 11 DEHYDROSYDONIC ACID; 12 ACETOXY 1 DEOXYSYDONIC ACID; 12 ACETOXYSYDONIC ACID; 12 HYDROXYSYDONIC ACID; 3 METHOXYVIOLACEOL II; ANTIFUNGAL AGENT; CISPLATIN; CYCLO HYDROXYSYDONIC ACID; DIORCINOL F; DIORCINOL G; DIORCINOL H; DIPHENYL ETHER DERIVATIVE; FLUCONAZOLE; SESQUITERPENOID; SYDOWIOLS D; SYDOWIOLS E; UNCLASSIFIED DRUG; 11-DEHYDROSYDONIC ACID; 12-ACETOXYSYDONIC ACID; ANTINEOPLASTIC AGENT; SESQUITERPENE;

ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS VERSICOLOR; BIOASSAY; CANCER CELL LINE; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; CIRCULAR DICHROISM; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG IDENTIFICATION; DRUG SCREENING; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION; ASPERGILLUS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; ISOLATION AND PURIFICATION; LICHEN (ORGANISM); METABOLISM; MICROBIOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRECLINICAL STUDY; PROCEDURES; SECONDARY METABOLISM; TUMOR CELL LINE;

ASPERGILLUS VERSICOLOR; CANDIDA ALBICANS; FUNGI; LOBARIA QUERCIZANS;

ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; ASPERGILLUS; CANDIDA ALBICANS; CELL LINE, TUMOR; CIRCULAR DICHROISM; DRUG EVALUATION, PRECLINICAL; HUMANS; LICHENS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHENYL ETHERS; SECONDARY METABOLISM; SESQUITERPENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84927777949     PISSN: 16121872     EISSN: 16121880     Source Type: Journal    
DOI: 10.1002/cbdv.201400146     Document Type: Article

References (54)

1. M. M. Wagenaar, D. M. Gibson, J. Clardy, Org. Lett. 2002, 4, 671.
2. Y.-C. Wang, S.-B. Niu, S.-C. Liu, L.-D. Guo, Y.-S. Che, Org. Lett. 2010, 12, 5081.
3. W. Wu, H.-Q. Dai, L. Bao, B. Ren, J.-C. Lu, Y.-M. Luo, L.-D. Guo, L.-X. Zhang, H.-W. Liu, J. Nat. Prod. 2011, 74, 1303.
4. F. Zhang, L. Li, S.-B. Niu, Y.-K. Si, L.-D. Guo, X.-J. Jiang, Y.-S. Che, J. Nat. Prod. 2012, 75, 230.
5. G. Li, H.-Y. Wang, R.-X. Zhu, L.-M. Sun, L.-N. Wang, M. Li, Y.-Y. Li, Y.-Q. Liu, Z.-T. Zhao, H.-X. Lou, J. Nat. Prod. 2012, 75, 142.
6. Q.-X. Wang, L. Bao, X.-L. Yang, D.-L. Liu, H. Guo, H.-Q. Dai, F.-H. Song, L.-X. Zhang, L.-D. Guo, S.-J. Li, H.-W. Liu, Fitoterapia 2013, 90, 220.
7. E. M. K. Wijeratne, B. P. Bashyal, M. X. Liu, D. D. Rocha, G. M. K. B. Gunaherath, J. M. U'Ren, M. K. Gunatilaka, A. E. Arnold, L. Whitesell, A. A. L. Gunatilaka, J. Nat. Prod. 2012, 75, 361.
8. Q.-C. Zheng, G.-D. Chen, M.-Z. Kong, G.-Q. Li, J.-Y. Cui, X.-X. Li, Z.-Y. Wu, L.-D. Guo, Y.-Z. Cen, Y.-Z. Zheng, H. Gao, Steroids 2013, 78, 896.
9. J.-W. He, G.-D. Chen, H. Gao, F. Yang, X.-X. Li, T. Peng, L.-D. Guo, X.-S. Yao, Fitoterapia 2012, 83, 1087.
10. Y. Takenaka, T. Tanahashi, N. Nagakura, N. Hamada, Chem. Pharm. Bull. 2003, 51, 794.
11. H.-Q. Gao, L.-N. Zhou, S.-X. Cai, G.-J. Zhang, T.-J. Zhu, Q.-Q. Gu, D.-H. Li, J. Antibiot. 2013, 66, 539.
12. J. A. Ballantine, C. H. Hassall, B. D. Jones, Phytochemistry 1968, 7, 1529.
13. A. N. Yurchenko, O. F. Smetanina, A. I. Kalinovsky, M. V. Pivkin, P. S. Dmitrenok, T. A. Kuznetsova, Russ. Chem. Bull., Int. Ed. 2010, 59, 852.
14. T. Tanahashi, Y. Takenaka, N. Nagakura, N. Hamada, Phytochemistry 2001, 58, 1129.
15. T. Hamasaki, K. Nagayama, Y. Hatsuda, Agric. Biol. Chem. 1978, 42, 37.
16. H. Kropf, H. Von Wallis, J. Chem. Res., Synop. 1983, 11, 282.
17. T. Hamasaki, Y. Sato, Y. Hatsuda, Agric. Biol. Chem. 1975, 39, 2337.
18. A. R. Howell, G. Pattenden, J. Chem. Soc., Perkin Trans. 1 1990, 10, 2715.
19. G. Vidari, A. Di Rosa, G. Zanoni, C. Bicchi, Tetrahedron: Asymmetry 1999, 10, 3547.
20. Z.-Y. Lu, H.-J. Zhu, P. Fu, Y. Wang, Z.-H. Zhang, H.-P. Lin, P.-P. Liu, Y.-B. Zhuang, K. Hong, W.-M. Zhu, J. Nat. Prod. 2010, 73, 911.
21. Y. M. Chung, C. K. Wei, D. W. Chuang, M. El-Shazly, C. T. Hsieh, T. Asai, Y. Oshima, T. J. Hsieh, T. L. Hwang, Y. C. Wu, F. R. Chang, Bioorg. Med. Chem. 2013, 21, 3866.
22. X.-R. Liu, F.-H. Song, L. Ma, C.-X. Chen, X. Xiao, B. Ren, X.-T. Liu, H.-Q. Dai, A. M. Piggott, Y. Av-Gay, L.-X. Zhang, R. J. Capon, Tetrahedron Lett. 2013, 54, 6081.
23. L. J. Fremlin, A. M. Piggott, E. Lacey, R. J. Capon, J. Nat. Prod. 2009, 72, 666.
24. T. Bunyapaiboonsri, S. Yoiprommarat, K. Intereya, K. Kocharin, Chem. Pharm. Bull. 2007, 55, 304.
25. D. Li, Y. Xu, C.-L. Shao, R.-Y. Yang, C.-J. Zheng, Y.-Y. Chen, X.-M. Fu, P.-Y. Qian, Z.-G. She, N. J. de Voogd, Mar. Drugs 2012, 10, 234.
26. C.-L. Shao, Z.-G. She, Z.-Y. Guo, H. Peng, X.-L. Cai, S.-N. Zhou, Y.-C. Gu, Y.-C. Lin, Magn. Reson. Chem. 2007, 45, 434.
27. D. G. I. Kingston, P. N. Chen, J. R. Vercellotti, Phytochemistry 1976, 15, 1037.
28. J. Magano, M. H. Chen, J. D. Clark, T. Nussbaumer, J. Org. Chem. 2006, 71, 7103.
29. M. S. Morales-Ríos, J. Espiñeira, P. Joseph-Nathan, Magn. Reson. Chem. 1987, 25, 377.
30. Y. Takenaka, N. Hamada, T. Tanahashi, Phytochemistry 2005, 66, 665.
31. J. A. Elix, A. J. Jones, L. Lajide, B. J. Coppins, P. W. James, Aust. J. Chem. 1984, 37, 2349.
32. G. T. Yogui, J. L. Sericano, R. C. Montone, Sci. Total Environ. 2011, 409, 3902.
33. X. Fu, F. J. Schmitz, M. Govindan, S. A. Abbas, K. M. Hanson, P. A. Horton, P. Crews, M. Laney, R. C. Schatzman, J. Nat. Prod. 1995, 58, 1384.
34. X. Fu, F. J. Schmitz, J. Nat. Prod. 1996, 59, 1102.
35. W. A. König, K. P. Pfaff, W. Loeffler, D. Schanz, H. Zähner, Liebigs Ann. Chem. 1978, 8, 1289.
36. K. Shibata, T. Kamikawa, N. Kaneda, M. Taniguchi, Chem. Lett. 1978, 7, 797.
37. J. Hargreaves, J. Park, E. L. Ghisalberti, K. Sivasithamparam, B. W. Skelton, A. H. White, J. Nat. Prod. 2002, 65, 7.
38. K. Scherlach, H. W. Nützmann, V. Schroeckh, H. M. Dahse, A. A. Brakhage, C. Hertweck, Angew. Chem., Int. Ed. 2011, 50, 9843.
39. M. Chen, C.-L. Shao, X.-M. Fu, R.-F. Xu, J.-J. Zheng, D.-L. Zhao, Z.-G. She, C.-Y. Wang, J. Nat. Prod. 2013, 76, 1229.
40. Y.-F. Huang, X.-X. Li, G.-D. Chen, H. Gao, L.-D. Guo, X.-S. Yao, Junwu Xuebao 2012, 31, 769.
41. G. H. Yang, K. Yun, V. N. Nenkep, H. D. Choi, J. S. Kang, B. W. Son, Chem. Biodiversity 2010, 7, 2766.
42. M. S. R. Nair, S. T. Carey, Mycologia 1979, 71, 1089.
43. T. Itabashi, K. Nozawa, S. Nakajima, K. Kawai, Chem. Pharm. Bull. 1993, 41, 2040.
44. M. Yamazaki, Y. Maebayashi, Chem. Pharm. Bull. 1982, 30, 514.
45. J. B. Spencer, P. M. Jordan, J. Chem. Soc., Chem. Commun. 1992, 8, 646.
46. R. A. Werner, A. Rossmann, C. Schwarz, A. Bacher, H.-L. Schmidt, W. Eisenreich, Phytochemistry 2004, 65, 2809.
47. T. Mosmann, J. Immunol. Methods 1983, 6 5, 55.
48. L.-M. Sun, S.-J. Sun, A.-X. Cheng, X.-Z. Wu, Y. Zhang, H.-X. Lou, Antimicrob. Agents Chemother. 2009, 53, 1586.
49. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09 (Revision B.01), Gaussian, Inc., Wallingford, CT, 2010.
50. H. Sun, J. Phys. Chem. B 1998, 102, 7338.
51. C. Diedrich, S. Grimme, J. Phys. Chem. A 2003, 107, 2524.
52. A. Klamt, V. Jonas, J. Chem. Phys. 1996, 105, 9972.
53. A. Klamt, J. Phys. Chem. 1995, 99, 2224.
54. P. J. Stephens, N. Harada, Chirality 2010, 22, 229.