Contact us
닫기
Article Search
닫기

Microbiology and Biotechnology Letters

보문(Article)

View PDF

Bioactive Compounds / Food Microbiology  |  Biomolecules

Microbiol. Biotechnol. Lett. 2017; 45(3): 200-208

https://doi.org/10.4014/mbl.1705.05001

Received: May 4, 2017; Accepted: June 26, 2017

Anti-proliferative and Antioxidant Activities of 1-methoxy-3-methyl-8-hydroxy-anthraquinone, a Hydroxyanthraquinoid Extrolite Produced by Amycolatopsis thermoflava strain SFMA-103

C. Ganesh Kumar 1*, Poornima Mongolla 1, 4, Cheemalamarri Chandrasekhar 1, 4, Yedla Poornachandra 1, Bandi Siva 2, K. Suresh Babu 2 and Kallaganti Venkata Siva Ramakrishna 3

1Medicinal Chemistry and Biotechnology Division,, 2Natural Products Chemistry Division,, 2Nuclear Magnetic Resonance Centre, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500007, India, 3Department of Biotechnology, Acharya Nagarjuna University, Nagarjunanagar, Guntur 522510, India

Abstract

Go to

Actinobacteria are prolific producers of a large number of natural products with diverse biological activities. In the present study, an actinobacterium isolated from sunflower rhizosphere soil sample collected from Medak, Andhra Pradesh, South India was identified as Amycolatopsis thermoflava strain SFMA-103. A pigmented secondary metabolite in culture broth was extracted by using methanol and it was further purified by silica gel column chromatography with methanol-chloroform solvent system. Structural elucidation studies based on UV-visible, 1D and 2D-NMR, FT-IR, and mass spectroscopic analyses confirmed the structure as 1-methoxy-3-methyl-8-hydroxy-anthraquinone. It showed significant in vitro anticancer activity against lung cancer and lymphoblastic leukemia cells with IC50 values of 10.3 and 16.98 μM, respectively. In addition, 1-methoxy-3-methyl-8-hydroxy-anthraquinone showed good free radical scavenging activity by DPPH method with an EC50 of 18.2 μg/ml. It also showed other promising superoxide radical scavenging, nitric oxide radical scavenging and inhibition of lipid peroxidation activities. This is a first report of antiproliferative and antioxidant activities of 1-methoxy-3-methyl-8-hydroxy-anthraquinone isolated from A. thermoflava strain SFMA-103 which may find potential application in biotechnological and pharmaceutical fields.

Keywords: Anthraquinone, Amycolatopsis thermoflava, extrolite, antitumor, antioxidant

References

Go to
  1. Lancini G, Lorenzetti R. 1993. Biotechnology of antibiotics and other bioactive microbial metabolites. pp. 49-57. Plenum Press, New York and London.
    CrossRef
  2. Lazzarini A, Cavaletti L, Toppo G, Marinelli F. 2000. Rare genera of actinomycetes as potential producers of new antibiotics. Antonie van Leeuwenhoek 78: 399-405.
    Pubmed CrossRef
  3. Jensen PR, Mincer TJ, Williams PG, Fenical W. 2005. Marine actinomycete diversity and natural product discovery. Antonie van Leeuwenhoek 87: 43-48.
    Pubmed CrossRef
  4. Caro Y, Anamale L, Fouillaud M, Laurent P, Petit T, Dufosse L. 2012. Natural hydroxyanthraquinoid pigments as potent food grade colorants: an overview. Nat. Prod. Bioprospect. 2: 174-193.
    KoreaMed CrossRef
  5. Byrstrykh LV, Fernández-Moreno MA, Herrema JK, Malpartida F, Hopwood DA, Dukhuizen L. 1996. Production of actinorhodinrelated “blue-pigments” by Streptomyces coelicolor A3(2). J. Bacteriol. 178: 2238-2244.
    CrossRef
  6. Clark B, Capon RJ, Stewart M, Lacey E, Tennant S, Gill JH. 2004. Blanchaquinone: A new anthraquinone from an Australian Streptomyces sp. J. Nat. Prod. 67: 1729-1731.
    Pubmed CrossRef
  7. Adinarayana G, Venkateshan MR, Bapiraju VVSNK, Sujatha P, Premkumar J, Ellaiah P, Zeeck A. 2006. Cytotoxic compounds from the marine actinobacterium Streptomyces corchorusii AUBN(1)/7. Russ. J. Bioorg. Chem. 32: 295-300.
    CrossRef
  8. Igarashi Y, Trujillo M E, Martinez-Molina E, Yanase S, Miyanaga S, Obata T, et al. 2007. Antitumor anthraquinones from an endophytic actinomycete Micromonospora lupini sp. nov. Bioorg. Med. Chem. Lett. 17: 3702-3705.
    Pubmed CrossRef
  9. Xue CM, Tian L, Lin WH, Deng ZW. 2009. Anthraquinone derivatives from Micromonospora rhodorangea. Nat. Prod. Res. 23: 533538.
    Pubmed CrossRef
  10. Balachandran C, Arun Y, Duraipandiyan V, Ignacimuthu S, Balakrishna K, Al-Dhabi NA. 2014. Antimicrobial and cytotoxicity properties of 2,3-dihydroxy-9,10-anthraquinone isolated from Streptomyces galbus (ERINLG-127). Appl. Biochem. Biotechnol. 172: 3513-3528.
    Pubmed CrossRef
  11. Balachandran C, Duraipandiyan V, Arun Y, Sangeetha B, Emi N, AlDhabi NA, et al. 2016. Isolation and characterization of 2hydroxy-9,10-anthraquinone from Streptomyces olivochromogenes (ERINLG-261) with antimicrobial and antiproliferative properties. Revista Brasileira de Farmacognosia 26: 285-295.
    CrossRef
  12. Shirling EB, Gottlieb D. 1996. Methods for characterization of Streptomyces species. Int. J. Syst. Bacteriol. 16: 313-340.
    CrossRef
  13. Chun J, Kim SB, Oh YK, Seong CN, Lee DH, Bae KS, et al. 1999. Amycolatopsis thermoflava sp. nov., a novel soil actinomycete from Hainan Island, China. Int. J. Syst. Bacteriol. 49: 1369-1373.
    Pubmed CrossRef
  14. Haque SK, Sen SK, Pal SC. 1992. Screening and identification of antibiotic producing strains of Streptomyces. Hindustan Antibiot. Bull. 4: 76-83.
  15. Rainey FA, Rainey NW, Kroppenstedt RM, Stackebrandt E. 1996. The genus Nocardiopsis represents a phylogenetically coherent taxon and a distinct actinomycete lineage: proposal of Nocardiopsiaceae fam. nov. Int. J. Syst. Bacteriol. 46: 1088-1092.
    Pubmed CrossRef
  16. Tamura K, Nei M. 1983. Estimation of the number of nucleotide substitutions in the control region of mitochondrial DNA in humans and chimpanzees. Mol. Biol. Evol. 10: 512-526.
  17. Tamura K, Stecher G, Peterson D, Filipski A, Kumar S. 2013. MEGA6: Molecular Evolutionary Genetic Analysis version 6.0. Mol. Biol. Evol. 30: 2725-2729.
    Pubmed KoreaMed CrossRef
  18. Moon JH, Terao J. 1998. Antioxidant activity of caffeic acid and dihydrocaffeic acid in lard and human low-density lipoprotein. J. Agric. Food Chem. 46: 5062-5065.
    CrossRef
  19. Bors W, Heller W, Michel C, Saran M. 1990. Flavonoids as antioxidants:determination of radical-scavenging efficiencies. Methods Enzymol. 186: 343-355.
    CrossRef
  20. Liu F, Ooi VE, Chang ST. 1997. Free radical scavenging activities of mushroom polysaccharide extracts. Life Sci. 60: 763-771.
    CrossRef
  21. Zhang EX, Yu LJ. 1997. Studies on polysaccharide from Sargassum thunberg II for its ability to scavenge active oxygen species. Chin. J. Mar. Drugs 3: 1-4.
  22. Marcocci L, Packer L, Droy-Lefaix MT, Sekaki A, Gardes-Albert M. 1994. Antioxidant action of Ginkgo biloba extract EGb 761. Methods Enzymol. 234: 462-475.
    CrossRef
  23. Mosmann T. 1983. Rapid colorimetric assay for cellular growth and survival; application to proliferation and cytotoxicity assays. J. Immunol. Methods 65: 55-63.
    CrossRef
  24. Kim B, Sahin N, Tan GYA, Zakrzewska-Czerwinska J, Goodfellow M. 2002. Amycolatopsis eurytherma sp. nov., a thermophilic actinomycete isolated from soil. Int. J. Syst. Evol. Microbiol. 52: 889894.
  25. Huang Q, Lu G, Shen HM, Chung MC, Ong CN. 2007. Anti-cancer properties of anthraquinones from rhubarb. Med. Res. Rev. 27:609-630.
    Pubmed CrossRef
  26. Mao H, Schnetz-Boutaud NC, Weisenseel JP, Marnett LJ, Stone MP. 1999. Duplex DNA catalyzes the chemical rearrangement of a malondialdehyde deoxyguanosine adduct. Proc. Nat. Acad. Sci. USA 96: 6615-6620.
    Pubmed KoreaMed CrossRef
  27. Marnett LJ. 1999. Lipid peroxidation - DNA damage by malondialdehyde. Mutat. Res. 424: 83-95.
    CrossRef
  28. Hu Y, Martinez ED, MacMillan JB. 2012. Anthraquinones from a marine-derived Streptomyces spinoverrucosus. J. Nat. Prod. 75:1759-1764.
    Pubmed KoreaMed CrossRef
  29. Raju R, Gromyko O, Fedorenko V, Herrmann J, Luzhetskyy A, Müller R. 2013. Rubimycinone A, a new anthraquinone from a terrestrial Streptomyces sp. Tetrahedron Lett. 54: 900-902.
    CrossRef
  30. Huang YF, Tian L, Fu HW, Hua HM Pei YH. 2006. One new anthraquinone from marine Streptomyces sp. FX-58. Nat. Prod. Res. 20:1207-1210.
    Pubmed CrossRef
  31. Murphy BT, Narender T, Kauffman CA, Woolery M, Jensen PR, Fenical W. 2010. Saliniquinones A-F, new members of the highly cytotoxic anthraquinone-γ-pyrones from the marine actinomycete Salinispora arenicola. Aust. J. Chem. 63: 929-934.
    Pubmed KoreaMed CrossRef

Article Tools

Starts of Metrics

Share this article on :

Related articles in MBL

Most Searched Keywords ?

What is Most Searched Keywords?

  • It is most registrated keyword in articles at this journal during for 2 years.