Novel 1,5,7-Trihydroxy-3-Hydroxy Methyl Anthraquinone Isolated from Terrestrial Streptomyces sp. (eri-26) with Antimicrobial and Molecular Docking Studies

Applied Biochemistry and Biotechnology

Volumn 174, Issue 5, 2014, Pages 1784-1794

  Duraipandiyan, V ^a   AL Dhabi, N A ^a   Balachandran, C ^b   Raj, M Karunai ^b   Arasu, M Valan ^a   Ignacimuthu, S ^b  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

^b LOYOLA COLLEGE   (India)

Author keywords

16s rRNA; Antimicrobial; HPLC; l,5,7 Trihydroxy 3 hydroxy methyl anthraquinone; Molecular docking; Streptomyces sp

Indexed keywords

AROMATIC COMPOUNDS; ASPERGILLUS; BACTERIA; BACTERIOLOGY; ENZYME INHIBITION; KETONES; MOLECULAR MODELING; RNA; SOILS; URANIUM METALLOGRAPHY;

16S RRNA; ANTIMICROBIAL; HPLC; L,5,7-TRIHYDROXY-3-HYDROXY METHYL ANTHRAQUINONE; MOLECULAR DOCKING; STREPTOMYCES SP;

ANTIMICROBIAL AGENTS;

1,5,7 TIHYDROXY 3 HYDROXY METHYL ANTHRAQUINONE; ANTHRAQUINONE; ANTIINFECTIVE AGENT; BETA LACTAMASE; DNA TOPOISOMERASE IV; UNCLASSIFIED DRUG; AMPC BETA-LACTAMASES; ANTHRAQUINONE DERIVATIVE; BACTERIAL PROTEIN; PROTEIN BINDING;

ANTIMICROBIAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; BACILLUS SUBTILIS; BACTERIUM ISOLATION; BOTRYTIS; DRUG ISOLATION; ENERGY; ENZYME INHIBITION; EPIDERMOPHYTON FLOCCOSUM; FUNGUS; MICROORGANISM; MOLECULAR DOCKING; NONHUMAN; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; STREPTOMYCES; TRICHOPHYTON RUBRUM; ANTAGONISTS AND INHIBITORS; BACTERIAL PHENOMENA AND FUNCTIONS; BINDING SITE; CELL SURVIVAL; CHEMISTRY; CLASSIFICATION; COMPUTER SIMULATION; DRUG EFFECTS; ISOLATION AND PURIFICATION; METABOLISM; MICROBIOLOGY; PHYSIOLOGY; SPECIES DIFFERENCE; ULTRASTRUCTURE;

ASPERGILLUS NIGER; BACILLUS SUBTILIS; BOTRYOTINIA FUCKELIANA; EPIDERMOPHYTON FLOCCOSUM; FUNGI; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; STREPTOMYCES; STREPTOMYCES SP.; TRICHOPHYTON RUBRUM;

ANTHRAQUINONES; ANTI-INFECTIVE AGENTS; BACTERIAL PHYSIOLOGICAL PHENOMENA; BACTERIAL PROTEINS; BETA-LACTAMASES; BINDING SITES; CELL SURVIVAL; COMPUTER SIMULATION; DNA TOPOISOMERASE IV; FUNGI; MOLECULAR DOCKING SIMULATION; PROTEIN BINDING; SOIL MICROBIOLOGY; SPECIES SPECIFICITY; STREPTOMYCES;

EID: 84919950281     PISSN: 02732289     EISSN: 15590291     Source Type: Journal    
DOI: 10.1007/s12010-014-1157-y     Document Type: Article

References (38)

1. Wu, X., Chen, W., Qian, C., Li, O., Li, P., & Wang, Y. (2007). Isolation and identification of newly isolated antagonistic Streptomyces sp. strain AP19–2 producing chromomycins. Journal of Microbiology, 45, 499–504.
2. Williams, S. T., Goodfellow, M., & Alderson, G. (1989). Genus Streptomyces Waksman and Henrici 1943, 339AL. In S. T. Williams, M. E. Sharpe, & J. G. Holt (Eds.), Bergey’s manual of systematic bacteriology (Vol. 4, pp. 2453–2492). Baltimore: Williams and Willkins.
3. Fenical, W., Baden, D., Burg, M., Goyet, C. V., Grimes, J. D., Katz, M., Marcus, N. H., Pomponi, S., Rhines, P., Tester, P., & Vena, J. (1999). Marine-derived pharmaceuticals and related bioactive compounds. In W. Fenical (Ed.), From monsoons to microbes: understanding the ocean’s role in human health (pp. 71–86). Washington: National Academies Press.
4. Fenical, W., & Jensen, P. R. (2006). Developing a new resource for drug discovery: marine actinomycete bacteria. Nature Chemical Biology, 2, 666–673.
5. Watve, M. G., Tickoo, R., Jog, M. M., & Bhole, B. D. (2001). How many antibiotics are produced by the genus streptomyces? Archives Microbiology, 176, 386–390.
6. Bibb, M. J. (2005). Regulation of secondary metabolism in Streptomycetes. Current Opinion Microbiology, 8, 208–215.
7. Schrempf, H. (2001). Recognition and degradation of chitin by Streptomycetes. Antonie Van Leeuwenhoek. International Journal Of General And Molecular Microbiology, 79, 285–289.
8. Mehdi, R. B. A., Sioud, S., Fguira, L. F. B., Bejar, S., & Mellouli, L. (2006). Purification and structure determination of four bioactive molecules from a newly isolated Streptomyces sp. TN97 strain. Process Biochemistry, 41, 1506–151.
9. Mellouli, L., Mehdi, R. B., Sioud, S., Salem, M., & Bejar, S. (2003). Isolation, purification and partial characterization of antibacterial activities produced by a newly isolated Streptomyces sp. US24 strain. Research Microbiology, 154, 345–52.
10. Lomovskaya, N., Fonstein, L., Ruan, X., Stassi, D., Katz, L., & Hutchinson, C. R. (1997). Gene disruption and replacement in the rapamycin producing Streptomyces hygroscopicus strain ATCC 29253. Microbiology, 143, 875–883.
11. Yamaquchi, H., Sato, S., Yoshida, S., Takada, K., Itoh, M., Seto, H., & Otake, N. (1986). Capuramycin, a new nucleoside antibiotic. Taxonomy, fermentation, isolation and characterization. Journal of Antibiotics Tokyo, 39, 1047–1053.
12. Miller, E. D., Kauffman, C. A., Jensen, P. R., & Fenical, W. (2007). Piperazimycins cytotoxic hexadepsipeptides from a marine derived bacterium of the genus Streptomyces. Journal of Organic Chemistry, 72, 323–330.
13. Yokomizo, K., Miyamoto, Y., Nagao, K., Kumagae, E., Habib, E. S. E., Suzuki, K., Harada, S., & Uyeda, M. (1998). Fattiviracin A1, a novel antiviral agent produced by Streptomyces microfl avus strain no. 2445. II. biological properties. Journal of Antibiotics Tokyo, 51, 1035–1039.
14. Adinaryan, G., Venkateshan, M. R., Bpiraju, V. V., Sujatha, P., Premkumar, J., Ellaiah, P., & Zeeck, A. (2006). Cytotoxic compounds from the marine actinobacterium. Bioorganisk Khimiya, 32, 328–334.
15. Agarwal, S. K., Singh, S. S., Verma, S., & Kumar, S. (2000). Antifungal activity of anthraquinone derivatives from Rheum emodi. Journal of Ethnopharmacology, 72, 43–46.
16. Ifesan, B. O., Hamtasin, C., Mahabusarakam, W., & Voravuthikunchai, S. P. (2009). Assessment of antistaphylococcal activity of partially purified fractions and pure compounds from Eleutherine americana. Journal of Food Protection, 72, 354–359.
17. Chen, S. H., Lin, K. Y., Chang, C. C., Fang, C. L., & Lin, C. P. (2007). Aloe-emodin-induced apoptosis in human gastric carcinoma cells. Food and Chemical Toxicology, 45, 2296–2303.
18. Iizuka, A., Iijima, O. T., Kondo, K., Itakura, H., Yoshie, F., Miyamoto, H., Kubo, M., Higuchi, M., Takeda, H., & Matsumiy, T. (2004). Evaluation of Rhubarb using antioxidative activity as an index of pharmacological usefulness. Journal of Ethnopharmacology, 91, 89–94.
19. Barnard, D. L., Fairbairn, D. W., O’Neill, K. L., Gage, T. L., & Sidwell, R. W. (1995). Antihuman cytomegalovirus activity and toxicity of sulfonated anthraquinones and anthraquinone derivatives. Antivirus Research, 28, 317–321.
20. Hsieh, D. P. H., Singh, R., Yao, R. C., & Bennett, J. W. (1978). Anthraquinones in the biosynthesis of sterigmatocystin by Aspergillus versicolor. Applied Environmental Microbiology, 35, 980–982.
21. Valan Arasu, M., Duraipandiyan, V., Agastian, P., & Ignacimuthu, S. (2008). Antimicrobial activity of Streptomyces sp. ERI-26 recovered from Western Ghats of Tamil Nadu. Journal de Mycologie Médicale, 18, 147–153.
22. Duraipandiyan, V., & Ignacimuthu, S. (2009). Antibacterial and Antifungal activity of Flintersine isolated from the traditional medicinal plant, Toddalia asiatica (L.) Lam. Journal of Ethnopharmacology, 123, 494.
23. Clinical and Laboratory Standards Institute (CLSI), Reference method for Broth dilution antifungal susceptibility testing of filamentous fungi; Approved standard - second edition. CLSI document M38-A2 (ISBN 1-56238-668-9). Clinical and Laboratory Standards Institute, 940, West valley Road, Suite 1400, Wayne, Pennsylvania, USA, 2008.
24. NCCLS, M27-A2, In National Committee for Clinical Laboratory Standards. Reference method for broth dilution antifungal susceptibility testing of yeasts: proposed standard, 2002.
25. Sanner, M. F. (1999). Python: a programming language for software integration and development. Journal of Molecular Graphics Modeling, 17, 57–61.
26. Morris, G. M., Goodsell, D. S., Halliday, R. S., Huey, R., Hart, W. E., Belew, R. K., & Olson, A. J. (1998). Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. Journal of Computational Chemistry, 19, 1639–1662.
27. Pettersen, E. F., Goddard, T. D., Huang, C. C., Couch, G. S., Greenblatt, D. M., Meng, E. C., & Ferrin, T. E. (2004). UCSF chimera—a visualization system for exploratory research and analysis. Journal of Computational Chemistry, 25, 1605–1612.
28. The PyMOL Molecular Graphics System (2010), Version 1.3, Schrödinger, LLC.
29. Thomason, R. H. (1977). Naturally occurring quinones (p. 67). London: Acadamic press.
30. Fujimoto, H., Nakamura, E., Okuyama, E., & Ishibashi, M. (2004). Six immunosuppressive features from Ascomycete Zopfiella longicaudata found in screening study monitored by immunomodulatory activity. Chemical & Pharmaceutical Bulletin, 52, 1065–1068.
31. Cui, H. X., Shaaban, A. K., Schiebel, M., Qin, S., & Laatsch, H. (2008). New antibiotic with typical plant anthraquinone structure obtained studying terrestrial and marine Streptomycetes. World Journal of Microbiology and Biotechnology, 24, 419–421.
32. Hossain, M. S., Hossain, M. A., Rahman, M. M., Mondol, M. A. M., Bhuiyan, M. S. A., Gray, A. I., Flores, M. E., & Rashid, M. A. (2004). Amides from the fungus Streptomyces hygroscopicus and their antimicrobial activity. Phytochemistry, 65, 2147–2151.
33. Wang, Y., Luo, Q., Zhang, X., & Wang, W. (2011). Isolation and purification of a modified phenazine, griseoluteic acid, produced by Streptomyces griseoluteus P510. Research Microbiology, 162, 311–319.
34. Maskey, R. P., Helmke, E., & Laatsch, H. (2003). Himalomycin A and B isolation and structure elucidation of new fridamycin type antibiotics from a marine Streptomyces isolate. Journal of Antibiotics Tokyo, 56, 942–949.
35. Kwon, H. C., Kauffman, C. A., Jensen, P. R., & Fenical, W. (2006). Marinomycins A-D antitumor antibiotics of a new structure class from a marine actinomycete of the recently discovered genus “Marinispora”. Journal of the American Chemical Society, 128, 1622–1632.
36. Singh, V., Tripathi, C. K. M., & Bihari, V. (2008). Production, optimization and purification of an antifungal compound from Streptomyces capoamus MTCC 8123. Medicinal Chemistry Research, 17, 94–102.
37. Balachandran, C., Arun, Y., Duraipandiyan, V., Ignacimuthu, S., Balakrishna, K., & Al-Dhabi, N. A. (2014). Antimicrobial and cytotoxicity properties of 2,3-dihydroxy-9,10-anthraquinone isolated from Streptomyces galbus (ERINLG-127). Applied Biochemistry and Biotechnology, 172(7), 3513–3528.
38. Narayana, K. J. P., Kumar, K. G., & Vijayalakshmi, M. (2008). L-asparaginase production by Streptomyces albidoflavus. Indian Journal of Microbiology, 48, 331–336.