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References

  1. Bredholt H, Fjaervik E, Johnsen G, Zotchev SB. 2008. Actinomycetes from sediments in the Trondheim Fjord, Norway: diversity and biological activity. Mar. Drugs 6: 12-24.
    Pubmed PMC CrossRef
  2. Cappuccino JG. 2002. Microbiology, Laboratory Manual, pp. 282-283. Pearson Education Inc., New Delhi.
  3. Carr G , Derbyshire E R, C aldera E , Cu rrie C R, C lardy J. 2012. Antibiotic and antimalarial quinones from fungusgrowing ant-associated Pseudonocardia sp. J. Nat. Prod. 75:1806-1809.
    Pubmed PMC CrossRef
  4. Cimmino A, Puopolo G, Perazzolli M, Andolfi A, Melck D, Pertot I, et al. 2014. Cyclo (L-pro-L-tyr), the fungicide isolated from Lysobacter capsici az78: a structure–activity relationship study. Chem. Heterocycl. Compd. (NY) 50: 290295.
    CrossRef
  5. Comin J, Keller SW. 1959. Stoffwechselprodukte von Actinomyceten. N-Acetyl-tyramin. Helv. Chim. Acta 62: 17301732.
  6. Dekker KA, Inagaki T, Gootz TD, Huang LH, Kozima Y, Kohlbrenner WE, et al. 1998. New quinolone compounds from Pseudonocardia sp. with selective and potent anti Helicobacter pylori activity. Taxonomy of producing strain, fermentation, isolation, structural elucidation and biological activities. J. Antibiot. 51: 145-152.
    Pubmed CrossRef
  7. Donadio S, Monciardini P, Alduina R, Mazza P, Chiocchini C, Cavaletti L, et al. 2002. Microbial technologies for the discovery of novel bioactive metabolites. J. Biotechnol. 99:187-198.
    CrossRef
  8. Fenical W, Baden D, Burg M, de Goyet CV, Grimes JD, Michael K, et al. 1999. Marine derived pharmaceuticals and related bioactive compounds, pp. 71-86. In Fenical W (ed.). From Monsoons to Microbes: Understanding the Ocean’s Role in Human Health. National Academies Press.
  9. Fourati BFL, Fatso S, Ben Ameur MR, Mellouli L, Laatsch H. 2005. Purification and structure elucidation of antifungal and antibacterial activities of newly isolated Streptomyces sp. strains US80. Res. Microbiol. 156: 341-347.
    Pubmed CrossRef
  10. Guo Q, Guo D, Zhao B, Xu J, Li R. 2007. Two cyclic dipeptides from Pseudomonas fluorescens GcM5-1A carried by the pine wood nematode and their toxicities to Japanese black pine suspension cells and seedlings in vitro. J. Nematol. 39: 243-247.
    Pubmed PMC
  11. Hayakawa M. 2008. Studies on the isolation and distribution of rare actinomycetes in soil. Actinomycetologica 22: 12-19.
    CrossRef
  12. Henssen A. 1957. Beitrage zur morphologie und systematik der thermophilen actinomyceten. Arch. Mikrobiol. 26: 373-414.
    Pubmed CrossRef
  13. Hop DV, Sakiyama Y, Binh CT, Otoguro M, Hang DT, Miyadoh S, et al. 2011. Taxonomic and ecological studies of actinomycetes from Vietnam: isolation and genus-level diversity. J. Antibiot. 64: 599-606.
    Pubmed CrossRef
  14. http://www.ncbi.nlm.nih.gov/nuccore /341832466.
  15. Ismet A, Vikineswary S, Paramaswari S, Wong WH, Ward A, Seki T, et al. 2004. Production and chemical characterization of antifungal metabolites from Micromonospora sp. M39 isolated from mangrove rhizosphere soil. World J. Microbiol. Biotechnol. 20: 523-528.
    CrossRef
  16. Jensen PR, Fenical W. 1994. Strategies for the discovery of secondary metabolites from marine bacteria: ecological perspectives. Annu. Rev. Microbiol. 48: 559-584.
    Pubmed CrossRef
  17. Jimenez JT, Sturdikova M, Sturdika E. 2009. Natural products of marine origin and their perspectives in the discovery of new anticancer drugs. Acta Chim. Slov. 2: 63-74.
  18. Kumar PS, Preetam Raj JP, Duraipandiyan V, Ignacimuthu S. 2012. Antibacterial activity of some actinomycetes from Tamilnadu, India. Asian Pac. J. Trop. Biomed. 2: 936-943.
    CrossRef
  19. 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
  20. Lee MJ, Kong D, Han K, Sherman DH, Bai L, Deng LZ, et al. 2012. Structural analysis and biosynthetic engineering of a solubility improved and less hemolytic nystatin-like polyene in Pseudonocardia autotrophica. Appl. Microbiol. Biotechnol. 95:157-168.
    Pubmed CrossRef
  21. Li B, Gordon GM, Du CH, Xu J, Du W. 2010. Specific killing of Rb mutant cancer cells by inactivating TSC2. Cancer Cell 17: 469-480.
    Pubmed PMC CrossRef
  22. Li S, Tian X, Niu S, Zhang W, Chen Y, Zhang X, et al. 2011. Pseudonocardians A-C, new diazaanthraquinone derivatives from a deep sea actinomycetes Pseudonocardia sp. SCSIO 01299. Mar. Drugs 9: 1428-1439.
    Pubmed PMC CrossRef
  23. Maskey RP, Kock I, Helmke E, Laatsch H. 2003. Isolation and structure determination of phenazostatin D, a new phenazine from marine actinomycetes isolate Pseudonocardia sp. B6273. Z. Naturforsch. 58: 692-694.
  24. Mosmann T. 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65: 55-63.
    CrossRef
  25. Nolan R, Cross T. 1988. Isolation and screening of actinomycetes, pp. 1-32. In Goodfellow M, Williams ST, Mordarski M (eds.). Actinomycetes in Biotechnology. Academic Press, London.
    CrossRef
  26. Oh DC, Scott J J, C u rrie CR, C lardy J. 2 009. Mycangimycin, polyene peroxide from a mutualist Streptomyces sp. J. Org. Lett. 11: 633-636.
  27. Omura S, Tanaka H, Tanaka Y, Spiri-nakagawa P, Oiwa RY, Takahashi K, et al. 1979. Studies on bacterial cell wall inhibitors. VII. Azureomycins A and B, new antibiotics produced by Pseudonocardia azureanov sp. Taxonomy of the producing organism, isolation, characterization and biological properties. J. Antibiot. 32: 985-994.
    Pubmed CrossRef
  28. Smaoui S, Mathieu F, Elleuch L, Coppel Y, Merlina G, Karra-Rebai I, et al. 2012. Taxonomy, purification and chemical characterization of four bioactive compounds from new Streptomyces sp. TN256 strain. World J. Microbiol. Biotechnol. 28: 793-804.
    Pubmed CrossRef
  29. Thawai C, Tanasupawat S, Kudo T. 2008. Micromonospora pattaloongensis sp. nov. isolated from a Thai mangrove forest. Int. J. Syst. Evol. Microbiol. 58: 1516-1521.
    Pubmed CrossRef
  30. Ushakiranmayi M, Vijayalakshmi M, Sudhakar P, Sreenivasulu K. 2012. Isolation, identification and molecular characterization of rare actinomycetes from mangrove ecosystem of Nizampatnam. Malay. J. Microbiol. 8: 83-91.
  31. Wang B, Liang S, Zhang W, Zan Q. 2003. Mangrove flora of the world. Acta Bot. Sin. 45: 644-653.
  32. Yonezawa K, Yamada K, Kouno I. 2011. New diketopiperazine derivatives isolated from sea urchin-derived Bacillus sp. Chem. Pharm. Bull. 59: 106-108.
    CrossRef

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Article

Research article

J. Microbiol. Biotechnol. 2015; 25(5): 629-636

Published online May 28, 2015 https://doi.org/10.4014/jmb.1407.07041

Copyright © The Korean Society for Microbiology and Biotechnology.

Bioactive Metabolites Produced by Pseudonocardia endophytica VUK-10 from Mangrove Sediments: Isolation, Chemical Structure Determination and Bioactivity

Usha Kiranmayi Mangamuri 1, Muvva Vijayalakshmi 1*, Sudhakar Poda 2, Bramanandam Manavathi 3, Ch. Bhujangarao 4 and Y. Venkateswarlu 4

1Department of Botany and Microbiology, Acharya Nagarjuna University, Guntur-522510, Andhra Pradesh, India, 2Department of Biotechnology, Acharya Nagarjuna University, Guntur-522510, Andhra Pradesh, India, 3Molecular and Cellular Oncology Laboratory, Department of Biochemistry, School of Life Sciences, University of Hyderabad, Hyderabad-500046, India, 4Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500007, India

Received: July 15, 2014; Accepted: November 20, 2014

Abstract

Chemical investigation of the actinobacterial isolate Pseudonocardia endophytica VUK-10 has led
to the segregation of two known bioactive compounds, namely 4-(2-acetamidoethyl) phenyl
acetate and 4-((1, 4-dioxooctahydropyrrolo [1, 2-a] pyrazin-3-yl) methyl) phenyl acetate. The
strain was isolated from a sediment sample of the Nizampatnam mangrove ecosystem, south
coastal Andhra Pradesh, India. The chemical structure of the active compounds was
established on the basis of spectroscopic analysis, including 1H NMR and 13C NMR
spectroscopies, FTIR, and EIMS. The antimicrobial and cytotoxic activities of the bioactive
compounds produced by the strain were tested against opportunistic and pathogenic bacteria
and fungi and on MDA-MB-231, OAW, HeLa, and MCF-7 cell lines. The compounds exhibited
antimicrobial activities against gram-positive and gram-negative bacteria and fungi and also
showed potent cytotoxic activity against MDA-MB-231, OAW, HeLa, and MCF-7 cell lines.
This is the first example for this class of bioactive compounds isolated from Pseudonocardia of
mangrove origin.

Keywords: Mangrove Ecosystem, Pseudonocardia endophytica, Bioactive Compounds, 4-(2-acetamidoethyl) phenyl acetate, 4-((1, 4-dioxooctahydropyrrolo [1, 2-a] pyrazin-3-

References

  1. Bredholt H, Fjaervik E, Johnsen G, Zotchev SB. 2008. Actinomycetes from sediments in the Trondheim Fjord, Norway: diversity and biological activity. Mar. Drugs 6: 12-24.
    Pubmed KoreaMed CrossRef
  2. Cappuccino JG. 2002. Microbiology, Laboratory Manual, pp. 282-283. Pearson Education Inc., New Delhi.
  3. Carr G , Derbyshire E R, C aldera E , Cu rrie C R, C lardy J. 2012. Antibiotic and antimalarial quinones from fungusgrowing ant-associated Pseudonocardia sp. J. Nat. Prod. 75:1806-1809.
    Pubmed KoreaMed CrossRef
  4. Cimmino A, Puopolo G, Perazzolli M, Andolfi A, Melck D, Pertot I, et al. 2014. Cyclo (L-pro-L-tyr), the fungicide isolated from Lysobacter capsici az78: a structure–activity relationship study. Chem. Heterocycl. Compd. (NY) 50: 290295.
    CrossRef
  5. Comin J, Keller SW. 1959. Stoffwechselprodukte von Actinomyceten. N-Acetyl-tyramin. Helv. Chim. Acta 62: 17301732.
  6. Dekker KA, Inagaki T, Gootz TD, Huang LH, Kozima Y, Kohlbrenner WE, et al. 1998. New quinolone compounds from Pseudonocardia sp. with selective and potent anti Helicobacter pylori activity. Taxonomy of producing strain, fermentation, isolation, structural elucidation and biological activities. J. Antibiot. 51: 145-152.
    Pubmed CrossRef
  7. Donadio S, Monciardini P, Alduina R, Mazza P, Chiocchini C, Cavaletti L, et al. 2002. Microbial technologies for the discovery of novel bioactive metabolites. J. Biotechnol. 99:187-198.
    CrossRef
  8. Fenical W, Baden D, Burg M, de Goyet CV, Grimes JD, Michael K, et al. 1999. Marine derived pharmaceuticals and related bioactive compounds, pp. 71-86. In Fenical W (ed.). From Monsoons to Microbes: Understanding the Ocean’s Role in Human Health. National Academies Press.
  9. Fourati BFL, Fatso S, Ben Ameur MR, Mellouli L, Laatsch H. 2005. Purification and structure elucidation of antifungal and antibacterial activities of newly isolated Streptomyces sp. strains US80. Res. Microbiol. 156: 341-347.
    Pubmed CrossRef
  10. Guo Q, Guo D, Zhao B, Xu J, Li R. 2007. Two cyclic dipeptides from Pseudomonas fluorescens GcM5-1A carried by the pine wood nematode and their toxicities to Japanese black pine suspension cells and seedlings in vitro. J. Nematol. 39: 243-247.
    Pubmed KoreaMed
  11. Hayakawa M. 2008. Studies on the isolation and distribution of rare actinomycetes in soil. Actinomycetologica 22: 12-19.
    CrossRef
  12. Henssen A. 1957. Beitrage zur morphologie und systematik der thermophilen actinomyceten. Arch. Mikrobiol. 26: 373-414.
    Pubmed CrossRef
  13. Hop DV, Sakiyama Y, Binh CT, Otoguro M, Hang DT, Miyadoh S, et al. 2011. Taxonomic and ecological studies of actinomycetes from Vietnam: isolation and genus-level diversity. J. Antibiot. 64: 599-606.
    Pubmed CrossRef
  14. http://www.ncbi.nlm.nih.gov/nuccore /341832466.
  15. Ismet A, Vikineswary S, Paramaswari S, Wong WH, Ward A, Seki T, et al. 2004. Production and chemical characterization of antifungal metabolites from Micromonospora sp. M39 isolated from mangrove rhizosphere soil. World J. Microbiol. Biotechnol. 20: 523-528.
    CrossRef
  16. Jensen PR, Fenical W. 1994. Strategies for the discovery of secondary metabolites from marine bacteria: ecological perspectives. Annu. Rev. Microbiol. 48: 559-584.
    Pubmed CrossRef
  17. Jimenez JT, Sturdikova M, Sturdika E. 2009. Natural products of marine origin and their perspectives in the discovery of new anticancer drugs. Acta Chim. Slov. 2: 63-74.
  18. Kumar PS, Preetam Raj JP, Duraipandiyan V, Ignacimuthu S. 2012. Antibacterial activity of some actinomycetes from Tamilnadu, India. Asian Pac. J. Trop. Biomed. 2: 936-943.
    CrossRef
  19. 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
  20. Lee MJ, Kong D, Han K, Sherman DH, Bai L, Deng LZ, et al. 2012. Structural analysis and biosynthetic engineering of a solubility improved and less hemolytic nystatin-like polyene in Pseudonocardia autotrophica. Appl. Microbiol. Biotechnol. 95:157-168.
    Pubmed CrossRef
  21. Li B, Gordon GM, Du CH, Xu J, Du W. 2010. Specific killing of Rb mutant cancer cells by inactivating TSC2. Cancer Cell 17: 469-480.
    Pubmed KoreaMed CrossRef
  22. Li S, Tian X, Niu S, Zhang W, Chen Y, Zhang X, et al. 2011. Pseudonocardians A-C, new diazaanthraquinone derivatives from a deep sea actinomycetes Pseudonocardia sp. SCSIO 01299. Mar. Drugs 9: 1428-1439.
    Pubmed KoreaMed CrossRef
  23. Maskey RP, Kock I, Helmke E, Laatsch H. 2003. Isolation and structure determination of phenazostatin D, a new phenazine from marine actinomycetes isolate Pseudonocardia sp. B6273. Z. Naturforsch. 58: 692-694.
  24. Mosmann T. 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65: 55-63.
    CrossRef
  25. Nolan R, Cross T. 1988. Isolation and screening of actinomycetes, pp. 1-32. In Goodfellow M, Williams ST, Mordarski M (eds.). Actinomycetes in Biotechnology. Academic Press, London.
    CrossRef
  26. Oh DC, Scott J J, C u rrie CR, C lardy J. 2 009. Mycangimycin, polyene peroxide from a mutualist Streptomyces sp. J. Org. Lett. 11: 633-636.
  27. Omura S, Tanaka H, Tanaka Y, Spiri-nakagawa P, Oiwa RY, Takahashi K, et al. 1979. Studies on bacterial cell wall inhibitors. VII. Azureomycins A and B, new antibiotics produced by Pseudonocardia azureanov sp. Taxonomy of the producing organism, isolation, characterization and biological properties. J. Antibiot. 32: 985-994.
    Pubmed CrossRef
  28. Smaoui S, Mathieu F, Elleuch L, Coppel Y, Merlina G, Karra-Rebai I, et al. 2012. Taxonomy, purification and chemical characterization of four bioactive compounds from new Streptomyces sp. TN256 strain. World J. Microbiol. Biotechnol. 28: 793-804.
    Pubmed CrossRef
  29. Thawai C, Tanasupawat S, Kudo T. 2008. Micromonospora pattaloongensis sp. nov. isolated from a Thai mangrove forest. Int. J. Syst. Evol. Microbiol. 58: 1516-1521.
    Pubmed CrossRef
  30. Ushakiranmayi M, Vijayalakshmi M, Sudhakar P, Sreenivasulu K. 2012. Isolation, identification and molecular characterization of rare actinomycetes from mangrove ecosystem of Nizampatnam. Malay. J. Microbiol. 8: 83-91.
  31. Wang B, Liang S, Zhang W, Zan Q. 2003. Mangrove flora of the world. Acta Bot. Sin. 45: 644-653.
  32. Yonezawa K, Yamada K, Kouno I. 2011. New diketopiperazine derivatives isolated from sea urchin-derived Bacillus sp. Chem. Pharm. Bull. 59: 106-108.
    CrossRef