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Isolation and identification of a new antibacterial entity from the Antarctic cyanobacterium Nostoc CCC 537

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Abstract

The present study was aimed at the isolation, purification and structural elucidation of an antibacterial entity/lead molecule from the Antarctic cyanobacterium Nostoc CCC 537. A methanolic extract of the cyanobacterium was bioassayed with Enterobacter aerogenes as a target. The extract was purified by TLC, and the most active band was subjected to HPLC. The fraction (retention time 15.7 min) designated as the active principle was antibacterial towards Gram positive Mycobacterium tuberculosis H37Rv, Staphylococcus aureus ATCC 25923, Gram negative Salmonella typhi MTCC 3216, Pseudomonas aeruginosa ATCC 27853, Escherichia coli ATCC 25992, Enterobacter aerogenes MTCC 2822 and multi-drug resistant strains of Escherichia coli GS 2003/01, 02, 03. Based on UV, IR, 1H NMR, EIMS, and ESIMS data, the structure of the active principle is proposed as 4-[(5-carboxy-2-hydroxy)-benzyl]-1,10-dihydroxy-3,4,7,11,11-pentamethyloctahydrocyclopenta<a>naphthalene (Mr 428, Mp 243–249°C). This intracellular biomolecule is similar to anthraquinone and indane derivatives of a diterpenoid. The rate of production of the active principle currently corresponds to 1.70 mg g−1 biomass dry weight. The inherent property of Nostoc sp. to synthesise niche-specific biomolecules/lead molecules may be exploited for future drug development.

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References

  • Asthana RK, Srivastava A, Singh AP, Deepali, Singh SP, Nath G, Srivastava R, Srivastava BS (2006) Identification of an antimicrobial entity from the cyanobacterium Fischerella sp. isolated from bark of Azadirachta indica (Neem) tree. J Appl Phycol 18:33–39

    Article  CAS  Google Scholar 

  • Banker R, Carmeli S (1998) Tenuecyclamides A–D, cyclic hexapeptides from the cyanobacterium Nostoc spongiaeforme var. tenue. J Nat Prod 61:1248–1251

    Article  PubMed  CAS  Google Scholar 

  • Bauer AW, Kirby WM, Sherris JC, Turck M (1966) Antibiotic susceptibilitiy testing by a standardized single disk method. Am J Clin Pathol 45:493–496

    PubMed  CAS  Google Scholar 

  • Becher PG, Beuchat J, Gademann K, Jüttner F (2005) Nostocarboline: isolation and synthesis of a new cholinesterase inhibitor from Nostoc 78-12A. J Nat Prod 68:1793–1795

    Article  PubMed  CAS  Google Scholar 

  • Biondi N, Piccardi R, Margheri MC, Rodolfi L, Smith GD, Tredici MR (2004) Evaluation of Nostoc strain ATCC 53789 as a potential source of natural pesticides. Appl Environ Microbiol 70(6):3313–3320

    Article  PubMed  CAS  Google Scholar 

  • Blom JF, Brütsch T, Barbaras D, Bethuel Y, Locher HH, Hubschwerlen C, Gademann K (2006) Potent algicides based on the cyanobacterial alkaloid nostocarboline. Org Lett 8(4):737–740

    Article  PubMed  CAS  Google Scholar 

  • Boyd MR, Gustafson KR, McMohan JB, Shoemaker RH, O’Keefe BR, Mori T, Gulakowski RJ, Wu L, Rivera MI, Laurencot CM, Currens MJ, Cardellina IJH, Buckheit JRW, Nara PL, Pannell LK, Sowder IRC, Henderson LE (1997) Discovery of cyanovirin-N, a novel human immunodeficiency virus-inactivating protein that binds viral surface envelope glycoprotein gp120: potential application to microbicide development. Antimicrob Agents Chemother 41:1521–1530

    PubMed  CAS  Google Scholar 

  • Burja AM, Banaigs B, Abou-Mansour E, Burgess JG, Wright PC (2001) Marine cyanobacteria—a prolific source of natural products. Tetrahedron 57:9347–9377

    Article  CAS  Google Scholar 

  • Burns BP, Seifert A, Goh F, Francesco P, Jungblut A-D, Serhat A, Neilan BA (2005) Genetic potential for secondary metabolite production in stromatolite communities. FEMS Microbiol Lett 243(1):293–301

    Article  PubMed  CAS  Google Scholar 

  • Clardy J, Walsh C (2004) Lessons from natural molecules. Nature 432:829–837

    Article  PubMed  CAS  Google Scholar 

  • Dey B, Lerner DL, Lusso P, Boyd MR, Elder JH, Berger EA (2000) Multiple antiviral activities of cyanovirin-N: blocking of human immunodeficiency virus type 1 gp120 interaction with CD4 and coreceptor and inhibition of diverse enveloped viruses. J Virol 74:4562–4569

    Article  PubMed  CAS  Google Scholar 

  • Doan NT, Rickards RW, Rothschild JM, Smith GD (2000) Allelopathic actions of the alkaloid 12-epi-hapalindole E isonitrile and calothrixin A from cyanobacteria of the genera Fischerella and Calothrix. J Appl Phycol 12:409–416

    Article  CAS  Google Scholar 

  • Dodds WK, Gudder DA, Mollenhauer D (1995) The ecology of Nostoc. J Phycol 31:2–18

    Article  CAS  Google Scholar 

  • Erhard M, Döhren HV, Junblut P (1997) Rapid typing and elucidation of new secondary metabolites of intact cyanobacteria using MALDI-TOF mass spectrometry. Nat Biotechnol 15:906–909

    Article  PubMed  CAS  Google Scholar 

  • Fenical W, Jensen PR (2006) Developing a new resource for drug discovery: marine actinomycete bacteria. Nat Chem Biol 2:666–673

    Article  PubMed  CAS  Google Scholar 

  • Gerloff GC, Fitzgerald GP, Skoog F (1950) The isolation, purification and culture of blue-green algae. Am J Bot 27:216–218

    Article  Google Scholar 

  • Ghasemi Y, Yazdi MT, Shafiee A, Amini M, Shokravi S, Zarrini G (2004) Parsiguine, a novel antimicrobial substance from Fischerella ambigua. Pharm Biol 42:318–322

    Article  CAS  Google Scholar 

  • Hemscheidt T, Puglisi MP, Larsen LK, Petterson GML, Moore RE, Rios JL, Clardy J (1994) Structure and biosynthesis of borophycin, a new boeseken complex of boric acid from marine strain of the blue green alga Nostoc linckia. J Org Chem 59:3467–3471

    Article  CAS  Google Scholar 

  • Hirata K, Takashina J, Nakagami H, Ueyama S, Murakami K, Kanamori T, Miyamoto K (1996) Growth inhibition of various organisms by a violet pigment, nostocine A, produced by Nostoc spongiaeforme. Biosci Biotechnol Biochem 66:1905–1906

    Article  Google Scholar 

  • Jaki B, Orjala J, Sticher O (1999a) A novel extracellular diterpenoid with antibacterial activity from the cyanobacterium Nostoc commune. J Nat Prod 62:502–503

    Article  PubMed  CAS  Google Scholar 

  • Jaki B, Orjala J, Burgi H-R, Sticher O (1999b) Biological screening of cyanobacteria for antimicrobial and molluscicidal activity, brine shrimp lethality, and cytotoxicity. Pharm Biol 37:138–143

    Article  Google Scholar 

  • Jaki B, Orjala J, Heilmann J, Lindne A, Vogler B, Sticher O (2000a) Novel extracellular diterpenoids with biological activity from the cyanobacterium Nostoc commune. J Nat Prod 63:339–343

    Article  PubMed  CAS  Google Scholar 

  • Jaki B, Heilmann J, Sticher O (2000b) New antibacterial metabolites from the cyanobacterium Nostoc commune (EAWAG 122b). J Nat Prod 63:1283–1285

    Article  PubMed  CAS  Google Scholar 

  • Kaneko T, Nakamura Y, Wolk CP, Kuritz T, Sasamoto S, Watanave A, Iriguchi M, Ishikawa A, Kawashima K, Kimura T, Kishida Y, Kohara M, Matsumoto M, Matsuno A, Muraki A, Nakazaki N, Shimpo S, Sugimoto M, Takazawa M, Yamada M, Yasuda M, Tabata S (2001) Complete genomic sequence of the filamentous nitrogen-fixing cyanobacterium Anabaena sp. strain PCC 7120. DNA Res 8:205–213

    Article  PubMed  CAS  Google Scholar 

  • Kartz WA, Myers J (1955) Nutrition and growth of several blue-green algae. Am J Bot 42:282–287

    Article  Google Scholar 

  • Klein D, Daloze D, Braekman JC, Hoffmann L, Demoulin V (1995) New hapalindoles from the cyanophyte Hapalosiphon laingii. J Nat Prod 58:1781–1785

    Article  CAS  Google Scholar 

  • Los D, Horvath I, Vigh L, Murata N (1993) The temperature-dependent expression of the desaturase gene desA in Synechocystis PCC 6803. FEBS Lett 318:57–60

    Article  PubMed  CAS  Google Scholar 

  • Moore RE (1996) Cyclic peptides and depsipeptides from cyanobacteria: a review. J Ind Microbiol 16:134–143

    Article  PubMed  CAS  Google Scholar 

  • Mundt S, Kreitlow S, Nowotny A, Effmert U (2001) Biochemical and pharmacological investigations of selected cyanobacteria. Int J Hyg Environ Health 203:327–334

    Article  PubMed  CAS  Google Scholar 

  • Nagatsu A, Kajitani H, Sakakibara J (1995) Muscoride A: a new oxazole peptide alkaloid from freshwater cyanobacterium Nostoc muscorum. Tet Lett 36:4097–4100

    Article  CAS  Google Scholar 

  • Namikoshi M, Rinehart KL (1996) Bioactive compounds produced by cyanobacteria. J Ind Microbiol 17:373–384

    Article  CAS  Google Scholar 

  • National Committee for Clinical Laboratory Standards (1997) Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard M7-A4. Wayne, PA, USA

  • Neilan BA, Dittmann E, Rouhiainen L, Bass RA, Schaub V, Sivonen K, Börner T (1999) Nonribosomal peptide synthesis and toxigenicity of cyanobacteria. J Bacteriol 181(13):4089–4097

    PubMed  CAS  Google Scholar 

  • Poliquin K, Ershov YV, Cunningham FX Jr, Woreta TT, Gantt RR, Gantt E (2004) Inactivation of sll1556 in Synechocystis strain PCC 6803 impairs isoprenoid biosynthesis from pentose phosphate cycle substrate in vitro. J Bacteriol 186:4685–4693

    Article  PubMed  CAS  Google Scholar 

  • Raveh A, Carmeli S (2007) Antimicrobial ambiguines from the cyanobacterium Fischerella sp. collected in Israel. J Nat Prod 70:196–201

    Article  PubMed  CAS  Google Scholar 

  • Skulberg OM (2000) Microalgae as a source of bioactive molecules-experience from cyanophytes research. J Appl Phycol 12:341–348

    Article  CAS  Google Scholar 

  • Taton A, Grubisic S, Ertz D, Hodgson DA, Piccardi R, Biondi N, Tredici MR, Mainini M, Losi D, Marinelli F, Wilmotte A (2006) Polyphasic study of antarctic cyanobacterial strains. J Phycol 42:1257–1270

    Article  CAS  Google Scholar 

  • Vigh L, Los DA, Horvath I, Murata N (1993) The primary signal in the biological perception of temperature: Pd- catalyzed hydrogenation of membrane lipids stimulated the expression of the desA gene in Synechocystis PCC 6803. Proc Natl Acad Sci USA 90:9090–9094

    Article  PubMed  CAS  Google Scholar 

  • Vincent WF (2000) Cyanobacterial dominance in the polar regions. In: Whitton BA, Pott M (eds) The ecology of cyanobacteria. Kluwer, Dordrecht, pp 321–340

    Google Scholar 

  • Wada H, Gombos Z, Murata N (1990) Enhancement of chilling tolerance of a cyanobacterium by genetic manipulation of fatty acid desaturation. Nature 347:200–203

    Article  PubMed  CAS  Google Scholar 

  • Wada H, Gombos Z, Murata N (1994) Contribution of membrane lipids to the ability of the photosynthetic machinery to tolerate temperature stress. Proc Natl Acad Sci USA 91:4273–4277

    Article  PubMed  CAS  Google Scholar 

  • Walsh C (2003) Where will new antibiotics come from? Nat Rev Microbiol 1:65–70

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgements

We are grateful to the Head and Programme Coordinator, CAS in Botany, for laboratory facilities, the Departments of Chemistry (NMR) and Chemical Engineering, IT (HPLC), Banaras Hindu University, Head, RSIC, CDRI, and Lucknow (EIMS and ESIMS), for financial support to Deepali (UGC), Arunima Srivastava (CSIR). We are also grateful to Dr. A.P. Singh (DST, India) and Dr. M. S. Singh, Department of Chemistry, for help with nomenclature of the active principle.

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Authors and Affiliations

  1. Centre of Advanced Study in Botany, Banaras Hindu University, Varanasi, 221005, India

    Ravi K. Asthana,  Deepali, Manoj K. Tripathi, Arunima Srivastava, Akhilesh P. Singh & Sureshwar P. Singh

  2. Department of Microbiology, Institute of Medical Sciences, Banaras Hindu University, Varanasi, 221005, India

    Gopal Nath

  3. Microbiology Division, Central Drug Research Institute, Lucknow, 226001, India

    Ranjana Srivastava & Brahm S. Srivastava

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  1. Ravi K. Asthana
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  2. Deepali
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  3. Manoj K. Tripathi
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  4. Arunima Srivastava
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Correspondence to Ravi K. Asthana.

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Asthana, R.K., Deepali, Tripathi, M.K. et al. Isolation and identification of a new antibacterial entity from the Antarctic cyanobacterium Nostoc CCC 537. J Appl Phycol 21, 81–88 (2009). https://doi.org/10.1007/s10811-008-9328-2

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