Isolation and characterization of 2-hydroxy-9,10-anthraquinone from Streptomyces olivochromogenes (ERINLG-261) with antimicrobial and antiproliferative properties

Revista Brasileira de Farmacognosia

Volumn 26, Issue 3, 2016, Pages 285-295

  Balachandran, Chandrasekar ^a,b   Duraipandiyan, Veeramuthu ^a,c   Arun, Yuvaraj ^d   Sangeetha, Balachandran ^e   Emi, Nobuhiko ^b   Al Dhabi, Naif Abdullah ^c   Ignacimuthu, Savarimuthu ^a,c   Inaguma, Yoko ^b   Okamoto, Akinao ^b   Perumal, Paramasivan T ^d  

^a LOYOLA COLLEGE   (India)

^b FUJITA HEALTH UNIVERSITY   (Japan)

^c KING SAUD UNIVERSITY   (Saudi Arabia)

^d CENTRAL LEATHER RESEARCH INSTITUTE   (India)

^e Advinus Therapeutics Private Limited Bangalore   (India)

Author keywords

10 anthraquinone; 2 Hydroxy 9; Antimicrobial; Cytotoxic; Molecular docking; Streptomyces olivochromogenes

Indexed keywords

2 HYDROXY 9,10 ANTHRAQUINONE; ANTHRAQUINONE; RNA 16S; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; CYTOTOXICITY; GENE AMPLIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MINIMUM BACTERICIDAL CONCENTRATION; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; PHYLOGENETIC TREE; SEQUENCE ALIGNMENT; SEQUENCE ANALYSIS; SEQUENCE HOMOLOGY; STREPTOMYCES; STREPTOMYCES OLIVOCHROMOGENES;

EID: 84975064357     PISSN: None     EISSN: 1981528X     Source Type: Journal    
DOI: 10.1016/j.bjp.2015.12.003     Document Type: Article

References (49)

1. Agarwal, S.K., Singh, S.S., Verma, S., Kumar, S., 2000. Antifungal activity of anthraquinone derivatives from Rheum emodi. J. Ethnopharmacol. 72, 43–46.
2. Alguel, Y., Meng, C., Terán, W., Krell, T., Ramos, J.L., Gallegos, M.T., Zhang, X., 2007. Crystal structures of multidrug binding protein TtgR in complex with antibiotics and plant antimicrobials. J. Mol. Biol. 369, 829.
3. Anke, H., Kolthoum, I., Zihner, H., Laatsch, H., 1980. Metabolic products of microorganisms 185. The anthraquinones of the Aspergillus glaucus group. I. Occurrence, isolation, identification and antimicrobial activity. Arch. Microbiol. 126, 223–230.
4. Aouiche, A., Bijani, C., Zitouni, A., Mathieu, F., Sabaou, N., 2014. Antimicrobial activity of saquayamycins produced by Streptomyces spp. PAL114 isolated from a Saharan soil. J. Med. Mycol. 24, 17–23.
5. Arvind, S., Reg, F.C., Enzo, A.P., 2004. Identification of antimicrobial components of an ethanolic extract of the Australian medicinal plant, Eremophila duttonii. Phytother. Res. 18, 615–618.
6. Bacq-Calberg, C.M., Coyotte, J., Hoet, P., Nguyem-Disteeche, M., 1999. Microbiologie. De Boeck and Larcier, Bruxelles, pp. 338.
7. Balachandran, C., Duraipandiyan, V., Emi, N., Ignacimuthu, S., 2015. Antimicrobial and cytotoxic properties of Streptomyces sp (ERINLG-51) isolated from Southern Western Ghats. South Indian J. Biol. Sci. 1, 7–14.
8. Balachandran, C., Sangeetha, B., Duraipandiyan, V., KarunaiRaj, M., Ignacimuthu, S., Al-Dhabi, N.A., Balakrishna, K., Parthasarathy, K., Arulmozhi, N.M., Valan Arasu, M., 2014a. A flavonoid isolated from Streptomyces sp (ERINLG-4) induces apo-ptosis in human lung cancer A549 cells through p53 and cytochrome c release caspase-dependant pathway. Chem. Biol. Interact. 224, 24–35.
9. Balachandran, C., Arun, Y., Duraipandiyan, V., Ignacimuthu, S., Balakrishna, K., Al-Dhabi, N.A., 2014b. Antimicrobial and cytotoxicity properties of 2,3-dihydroxy-9,10-anthraquinone isolated from Streptomyces galbus (ERINLG-127). Appl. Biochem. Biotechnol. 172, 3513–3528.
10. Balachandran, C., Duraipandiyan, V., Balakrishna, K., Sundaram, L.R., Vijayakumar, A., Ignacimuthu, S., Al-Dhabi, N.A., 2013. Synthesis and medicinal properties of plant derived vilangin. Environ. Chem. Lett. 11, 303–308.
11. Balachandran, C., Duraipandiyan, V., Balakrishna, K., Ignacimuthu, S., 2012. Petroleum and polycyclic aromatic hydrocarbons (PAHs) degradation and naphthalene metabolism in Streptomyces sp (ERI-CPDA-1) isolated from oil contaminated soil. Bioresour. Technol. 112, 83–90.
12. Barasch, D., Zipori, O., Ringel, I., Ginsburg, I., Samuni, A., Katzhendler, J., 1990. Novel anthraquinone derivatives with redoxactive functional groups capable of producing free radicals by metabolism: are free radicals essential for cytotoxicity? Eur. J. Med. Chem. 34, 597–615.
13. 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. Antiviral Res. 28, 317–321.
14. Bernan, V.S., Montenegro, D.A., Korshalla, J.D., Maiese, W.M., Steinberg, D.A., Greenstein, M., 1994. Bioxalomycins new antibiotics produced by the marine Streptomyces sp. LL-31F508: taxonomy and fermentation. J. Antibiot. 47, 1417–1424.
15. Bringmann, G., Lang, G., Hamm, M.A., Gulder, T.A.M., Dieter, A., Bull, A.T., Stach, J.E.M., Kocher, N., Muller, W.E.G., Hans-Peter, F., 2005. Gephyromycin, the first bridged angucyclinone, from Streptomyces griseus strain NTK 14. Phytochemistry 66, 1366–1373.
16. Chen, S.H., Lin, K.Y., Chang, C.C., Fang, C.L., Lin, C.P., 2007. Aloeemodin induced apo-ptosis in human gastric carcinoma cells. Food. Chem. Toxicol. 45, 2296–2303.
17. Chennakesava Rao, K., Arun, Y., Easwaramoorthi, K., Balachandran, C., Prakasam, T., EswaraYuvaraj, T., Perumal, P.T., 2014. Synthesis, antimicrobial and molecular docking studies of enantiomerically pure N-alkylated b-amino alcohols from phenylpropanolamines. Bioorg. Med. Chem. Lett. 24, 3057–3063.
18. Clinical and Laboratory Standards Institute (CLSI), 2008. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Filamentous Fungi; Approved Standard Second–Edition CLSI Document M38-A2. Clinical and Laboratory Standards Institute, 940, West valley Road, Suite 1400, Wayne, Pennsylvania, 19087-1898 USA, ISBN 1-56238-668-9.
19. Cowan, M.M., 1999. Plant products as antimicrobial agents. Clin. Microbiol. Rev. 12, 564–582.
20. Cruz, R., Arias, M.E., Soliveri, J., 1999. Nutritional requirement for the production of Pyrazoloisoquinolinone antibiotics by Streptomyces griseocirneus NCIMB 40447. Appl. Microbiol. Biotechnol. 53, 115–119.
21. Demain, A.L., 1999. Pharmaceutically active secondary metabolites of microorganisms. Appl. Microbiol. Biotechnol. 52, 455–463.
22. Duraipandiyan, V., Sasi, A.H., Islam, V.I.H., Valanarasu, M., Ignacimuthu, S., 2010. Antimicrobial properties of actinomycetes from the soil of Himalaya. J. Mycol. Med. 20, 15–20.
23. Duraipandiyan, V., AL-Dhabi, N.A., Balachandran, C., Karunai Raj, M., Valan Arasu, M., Ignacimuthu, S., 2014. Novel 1,5,7-trihydroxy-3-hydroxy methyl anthraquinone isolated from terrestrial Streptomyces sp (ERI-26) with antimicrobial and molecular docking studies. Appl. Biochem. Biotechnol. 174, 1784–1794.
24. Fisher, G.R., Brown, J.R., Patterson, L.H., 1990. Involvement of hydroxyl radical formation and DNA strand breakage in the cytotoxicity of anthraquinone antitumor agents. Free. Radic. Res. Commun. 11, 117–125.
25. Hacene, H., Daoudi, H., Bhatnagar, T., Baratti, J.C., Lefebvre, G., 2000. H107, a new aminoglycosidase anti Pseudomonas antibiotic produced by a new strain of Spir-illosora. Microbios 102, 69.
26. Huang, H., Lan, X., Wang, Y., Tian, L., Fang, Y., Zhang, L., Zhang, K., Zheng, X., 2015. New bioactive derivatives of nonactic acid from the marine Streptomyces griseus derived from the plant Salicornia sp. Phytochem. Lett. 12, 190–195.
27. 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. J. Food Prot. 72, 354–359.
28. 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 antiox-idative activity as an index of pharmacological usefulness. J. Ethnopharmacol. 91, 89–94.
29. Lee, H.Z., Hsu, S.L., Liu, M.C., Wu, C.H., 2001. Effects and mechanisms of aloeemodin on cell death in human lung squamous cell carcinoma. Eur. J. Pharmacol. 431, 287–295.
30. Lee, H.Z., 2001. Protein kinase C involvement in aloeemodin and emodin induced apoptosis in lung carcinoma cell. Br. J. Pharmacol. 134, 1093–1103.
31. Manchester, J.I., Dussault, D.D., Rose, J.A., Boriack-Sjodin, P.A., Uria-Nickelsen, M., Ioannidis, G., Bist, S., Fleming, P., Hull, K.G., 2012. Discovery of a novel azaindole class of antibacterial agents targeting the ATPase domains of DNA gyrase and Topoisomerase IV. Bioorg. Med. Chem. Lett. 22, 5150–5156.
32. Mueller, S.O., Stopper, H., 1999. Characterization of the genotoxicity of anthraquinones in mammalian cells. Biochim. Biophys. Acta 1428, 406–414.
33. Narayana, K.J.P., Kumar, K.G., Vijayalakshmi, M., 2008. l-Asparaginase production by Streptomyces albidoflavus. Indian J. Microbiol. 48, 331–336.
34. National Committee for Clinical Laboratory Standards (NCCLS), 1999. Document M31-A Performance Standards for Antimicrobial Disk and Dilution Susceptibility Tests for Bacteria Isolated from Animals. National Committee for Clinical Laboratory Standards, Villanova, pp. 57 (approved standard NCCLS).
35. National Committee for Clinical Laboratory Standards (NCCLS), 2002. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts: Proposed Standard. National Committee for Clinical Laboratory Standards (NCCLS), Villanova.
36. Oskay, M., Tamer, A.U., Azeri, C., 2004. Antibacterial activity of some actinomycetes isolated from farming soils of Turkey. Afr. J. Biotechnol. 3, 441–446.
37. Patterson, L.H., Gandecha, B.M., Brown, J.R., 1983. 1,4-Bis{2-[(2-hydroxyethyl) amino] ethylamino}-9,10-anthracenedione, an anthraquinone antitumor agent that does not cause lipid peroxidation in vivo; comparison with daunorubicin. Biochem. Biophys. Res. Commun. 110, 399–405.
38. Raja, A., Prabakaran, P., 2011. Actinomycetes and drug—an overview. Am. J. Drug Dis. Dev. 1, 75–84.
39. Rambabu, V., Suba, S., Vijayakumar, S., 2014. Antimicrobial and antiproliferative prospective of kosinostatin–a secondary metabolite isolated from Streptomyces sp. J. Pharm. Anal. 5, 378–382.
40. Saha, K., Lam, K.W., Abas, F., Hamzah, A.S., Stanslas, J., Hui, L.S., Lajis, N.H., 2013. Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines. Med. Chem. Res. 22, 2093–2104.
41. Sanghvi, G.V., Ghevariya, D., Gosai, S., Langa, R., Dhaduk, N., Kunjadia, P.D., Vaishnav, D.J., Dave, G.S., 2014. Isolation and partial purification of erythromycin from alkaliphilic Streptomyces werraensis isolated from Rajkot, India. Biotechnol. Rep., 1–2, 2-7.
42. Sanner, M.F., 1999. Python: a programming language for software integration and development. J. Mol. Graph. Model. 17, 57–61.
43. Saravana Kumar, P., Al-Dhabi, N.A., Duraipandiyan, V., Balachandran, C., Praveen Kumar, P., Ignacimuthu, S., 2014. In vitro antimicrobial, antioxidant and cytotoxic properties of Streptomyces lavendulae strain SCA5. BMC Microbiol., http://dx.doi.org/10.1186/s12866-014-0291-6.
44. Savafi, L., Duran, N., Savafi, N., Onlem, Y., Ocak, S., 2005. The prevalence and resistance patterns of Pseudomans aeruginosa in intensive care units in a university Hospital. J. Med. Sci. 35, 317.
45. Shirling, J.L., Gottlieb, D., 1966. Methods for characterization of Streptomyces species. Int. J. Syst. Bacteriol. 16, 313–340.
46. Sosio, M., Bossi, E., Bianchi, A., Donadio, S., 2000. Multiple peptide synthetase gene clusters in actinomycetes. Mol. Genet. Genomics 264, 213–221.
47. Tamura, K., Dudley, J., Nei, M., Kumar, S., 2007. MEGA4: Molecular Evolutionary Genetics Analysis (MEGA) software version 4.0. Mol. Biol. Evol. 24, 1596–1599.
48. Urakawa, H., Kita-Tsukamoto, K., Ohwada, K., 1999. Microbial diversity in marine sediments from Sagami Bay and Tokyo Bay Japan, as determined by 16S rRNA gene analysis. Microbiology 145, 3305–3315.
49. Williams, S.T., Goodfellow, M., Alderson, G., Wllington, E.M., Sneath, P.H., Sacki, M.J., 1983. Numerical classification of Streptomyces and related genera. J. Gen. Microbiol. 129, 1747–1813.