Bioactive Compounds from Nostoc Species
Abstract
Recently microalgae have become commercially important because of novel compounds of potential medicinal value. Nostocspecies are producers of structurally and functionally diverse natural biological activities such as antibacterial, antiviral, anticancer, antitumor, algicide, antifungal, enzyme inhibiting, immunostimulant, antiplatelet aggregation, cytotoxic and antiplasmodium activities. Most of the isolated substances from the alga belong to groups of hydrocarbons such as phytane; lipids such as sterol, esters, waxes and free sterols; fatty acids such as dioic acids; derivatives of amino acids such as indole-3-acetic acid and anatoxin A; terpenoids and aromatic compounds such as diterpenoid and anthraquinone; boron-containing macrocycles such as borophycin; arsenolipids such as dimethylarsenic acid; mycosporine-like amino acids such as shinorine and scytonemin; lipopeptides such as cryptophycin-1 and polyketides and several carotenoids; amides, alkaloids, peptides, monosaccharides and polysaccharides. Some extracellular metabolites secreted by cyanobacteria function as toxins or allelochemicals. Apart from these cytotoxic metabolites (e.g. nostocyclophanes, borophycin, elastase inhibitors, antitumor, antifungal agent, antiviral indolocarbazoiles) they produce antimitotic compounds. This article provides an overview of bioactive compounds produced by Nostocspecies.
Keywords:
Cyanobacteria, Nostoc, Bioactive Compounds, , Biological activities, Allelochemicals.
References
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26. Arai M, Koizumi Y, Sato H, Kawabe T, Suganuma M, Kobayashi H, Tomoda H, Omura S. Boromycin abrogates bleomycininduced G2 checkpoint. J. Antib. 2004; 57: 662–668.
27. Banker R, Carmeli S. Tenuecyclamides A–D, cyclic hexapeptides from the cyanobacterium Nostoc spongiaeforme var. Tenue. J. Nat. Prod. 1998; 61: 1248–1251.
28. Nagatsu A, Kajitani H, Sakakibara J. Muscoride A: A new oxazole peptide alkaloid from freshwater cyanobacterium Nostoc muscorum. Tetrahedron Letters 1995; 36(23): 4097-4100.
29. Hammerschmidt FJ, Clark AM, El-Kashoury EA, El-Kawy MMA, ElFishawy AM. Chemical composition and antimicrobial activity of essential oils of Jasonia candicans and J. montana. Planta Med. 1993; 59: 68–70.
30. Devlin JP, Edwards OE, Gorham PR, Hunter NR, Pike RK, Stavric B. Anatoxin A, a toxic alkaloid from Anabaena flosaquae NRC-44h. Can.J.Chem. 1977; 55: 1367–1371.
31. Carmichael WW. The cyanotoxins, pp. 211–256 in J.A. Callow (Ed.): Advances in Botanical Research. Academic Press, London 1997.
32. Knubel G, Larsen LK, Moore RE, Levine IA, Patterson GM. Cytotoxic, antiviral indolocarbazoles from a blue-green alga belonging to the Nostocaceae. The Journal of Antibiotics XLIII. 1990; 10: 1236-1239.
33. Lai VWM, Cullen WR, Harrington CF, Reimer KJ. The characterization of arsenosugars in commercially available algal products including a Nostoc species of terrestrial origin. Appl.Organometal.Chem. 1997; 11: 797–803.
34. Řezanka T, Dor I, Prella A, Dembitsky VM. Fatty acid composition of six freshwater wild cyanobacterial species. Folia Microbiol. 2003; 48: 71–75.
35. Hall IH, Izydore RA, Warren AE, Barnes CR. Cytotoxicity and mode of action of aliphatic dicarboxylic acids in L1210 lymphocytic leukemia cells. Anticancer Res. 1999; 19: 205–211.
36. Ma X, Baraona E, Goozner BG, Lieber CS. Gender differences in mediumchain dicarboxylic acid uria in alcoholic men and women. Am.J.Med. 1999; 106: 70–75.
37. Singh I. Biochemistry of peroxisomes in health and disease. Mol.Cell.Biochem. 1997; 167: 1–29.
38. Řezanka T, Temina M, Tolstikov AG, Dembitsky VM. Natural microbial UV radiation filters – mycosporine-like amino acids. Folia Microbiol. 2004; 49: 339–352.
39. Jaki B, Orjala J, Sticher O. A novel extracellular diterpenoid with antibacterial activity from the cyanobacterium Nostoc commune. J.Nat.Prod. 1999; 62: 502–503.
40. Jaki B, Orjala J, Heilmann J, Linden A, Vogler B, Sticher O. Novel extracellular diterpenoids with biological activity from the cyanobacterium Nostoc commune. J.Nat.Prod. 2000b; 63: 339–343.
2. Hrouzek P, Lukesova A, Šimek M. Comparison of light and dark nitrogenase activity in selected soil cyanobacteria. Folia Microbiol. 2004; 49: 435–440. .
3. Browitzka MA. Microalgae as sources of pharmaceuticals and other biologically active compounds. J. Appl. Phycol. 1995; 7: 3-15.
4. Jaki B, Helimann J, Sticher O. New antibacterial metabolites from the cyanobacterium Nostoc commune. (EAWAG 122b). J. Nat. Prod. 2000; 63: 1283-85.
5. Kajiyama SI, Kanzaki H, Kawazu K, Kobayashi A. Nostofungicidine, an antifungal lipopeptide from the field-grown terrestrial blue-green alga Nostoc commune. Tetrahedron Letters 39 (22); 1998: 3737-3740.
6. Patterson GML, Carmeli S. Biological effects of tolytoxin (6-hydroxy-7-omethylscytophycin b), a potent bioactive metabolite from cyanobacteria. Arch. Microbiol. 1992; 157: 406-410.
7. Patterson GML, Larsen LK, Moore RE. Bioactive natural products from bluegreen algae. J. Appl. Phycol. 1994; 6: 151-157.
8. Gerwick WH, Roberts MA, Proteau PJ, Chen JL. Screening cultured marine microalgae for anticancer-type activity. J. Appl. Phycol, 1994; 6: 143-149.
9. Luesch H, Yoshida WY, Moore RE, Paul VJ, Mooberry SL. Isolation, structure determination, and biological activity of Lyngbya majuscule. Ibid. 2000; 63: 611-615.
10. Papke U, Gross EM, Francke W. Isolation, identification and determination of the absolute configuration of fischerellin B. A new algicide from the freshwater cyanobacterium Fischerella muscicola (Thuret). Tetrahedron Lett. 1997; 38: 379-382.
11. Rho M, Matsunaga K, Yasuda K, Ohizumi Y. A Novel monogalactosylacylglycerol with inhibitory effect on platelet aggregation from the cyanophyceae Oscillatoria rosea. J. nat. Prod. 1996; 59: 308-309.
12. Koehn FE, Longley RE, Reed JK. Microcolins A and B, new immunosuppressive peptide from the blue-green alga Lyngbya majuscule. J. Nat. Prod. 1992; 55: 613-619.
13. Papendorf O, Konig GM, Wright AD. Hirridin B and 2,4-dimethoxy-6- heptadecylphenol, secondary metabolites from the cyanobacterium Phormidium ectocarpi with antiplasmodial activity. Phytochem. 1998; 49: 2383-86.
14. Pflungmacher S. Possible allelopathic effects of cyanotoxins, with reference to microcystin-LR, in aquatic ecosystems. Environ. Toxicol. 2002; 17: 407-413.
15. Noaman NH, Fattah A, Khaleafa AF, Zaky SH. Factors affecting antimicrobial activity of Synechococcus leopoliensis. Microbiological Research. 2004; 159: 395-402.
16. Liu XJ, Chen F. Cell differentiation and colony alteration of Nostoc flagelliforme, an edible terrestrial cyanobacterium, in different liquid suspension cultures. Folia Microbiol. 2003; 48: 619–626.
17. Prasanna R, Pabby A, Singh PK. Effect of glucose and light–dark environment on pigmentation profiles in the cyanobacterium Calothrix elenkenii. Folia Microbiol. 2004; 49: 26–30.
18. Jaki B, Heilmann J, Sticher O. New antibacterial metabolites from the cyanobacterium Nostoc commune (EAWAG 122b). J.Nat.Prod. 2000a; 63: 1283–1285.
19. Gao KS. Chinese studies on the edible blue-green alga, Nostoc flagelliforme: a review. J.Appl.Phycol. 1998; 10: 37–49.
20. Rao CSVR. Antimicrobial activity of cyanobacteria. Indian J.Mar.Sci. 1994; 23: 55–56.
21. Singh DP, Tyagi MB, Kumar A, Thakur JK, Kumar A. Antialgal activity of a hepatotoxin-producing cyanobacterium, Microcystis aeruginosa. World J.Microbiol.Biotechnol. 2001; 17: 15–22.
22. Takenaka H, Yamaguchi Y, Sakaki S, Watarai K, Tanaka N, Hori M, Seki H, Tsuchida M, Yamada A, Nishimori T, Morinaga T. Safety evaluation of Nostoc flagelliforme (Nostocales, Cyanophyceae) as a potential food. Food Chem. Toxicol. 1998; 36: 1073–1077.
23. Huang ZB, Liu YD, Paulsen BS, Klaveness D. Studies on polysaccharides from three edible species of Nostoc (cyanobacteria) with different colony morphologies: comparison of monosaccharide compositions and viscosities of polysaccharides from field colonies and suspension cultures. J.Phycol. 1998; 34: 962–968.
24. Dembitsky VM, Srebnik M. Variability of hydrocarbon and fatty acid components in cultures of the filamentous cyanobacterium Scytonema sp. isolated from microbial community ‘Black Cover’ of limestone walls in Jerusalem. Biochemistry (Moscow) 2002; 67: 1545–1552.
25. Hemscheidt T, Puglisi MP, Larsen LK, Patterson GML, Moore RE, Rios JL, Clardy J. Structure and biosynthesis of borophycin, a new boeseken complex of boric acid from a marine strain of the blue-green alga Nostoc linckia. J.Org.Chem. 1994; 59: 3467–3471.
26. Arai M, Koizumi Y, Sato H, Kawabe T, Suganuma M, Kobayashi H, Tomoda H, Omura S. Boromycin abrogates bleomycininduced G2 checkpoint. J. Antib. 2004; 57: 662–668.
27. Banker R, Carmeli S. Tenuecyclamides A–D, cyclic hexapeptides from the cyanobacterium Nostoc spongiaeforme var. Tenue. J. Nat. Prod. 1998; 61: 1248–1251.
28. Nagatsu A, Kajitani H, Sakakibara J. Muscoride A: A new oxazole peptide alkaloid from freshwater cyanobacterium Nostoc muscorum. Tetrahedron Letters 1995; 36(23): 4097-4100.
29. Hammerschmidt FJ, Clark AM, El-Kashoury EA, El-Kawy MMA, ElFishawy AM. Chemical composition and antimicrobial activity of essential oils of Jasonia candicans and J. montana. Planta Med. 1993; 59: 68–70.
30. Devlin JP, Edwards OE, Gorham PR, Hunter NR, Pike RK, Stavric B. Anatoxin A, a toxic alkaloid from Anabaena flosaquae NRC-44h. Can.J.Chem. 1977; 55: 1367–1371.
31. Carmichael WW. The cyanotoxins, pp. 211–256 in J.A. Callow (Ed.): Advances in Botanical Research. Academic Press, London 1997.
32. Knubel G, Larsen LK, Moore RE, Levine IA, Patterson GM. Cytotoxic, antiviral indolocarbazoles from a blue-green alga belonging to the Nostocaceae. The Journal of Antibiotics XLIII. 1990; 10: 1236-1239.
33. Lai VWM, Cullen WR, Harrington CF, Reimer KJ. The characterization of arsenosugars in commercially available algal products including a Nostoc species of terrestrial origin. Appl.Organometal.Chem. 1997; 11: 797–803.
34. Řezanka T, Dor I, Prella A, Dembitsky VM. Fatty acid composition of six freshwater wild cyanobacterial species. Folia Microbiol. 2003; 48: 71–75.
35. Hall IH, Izydore RA, Warren AE, Barnes CR. Cytotoxicity and mode of action of aliphatic dicarboxylic acids in L1210 lymphocytic leukemia cells. Anticancer Res. 1999; 19: 205–211.
36. Ma X, Baraona E, Goozner BG, Lieber CS. Gender differences in mediumchain dicarboxylic acid uria in alcoholic men and women. Am.J.Med. 1999; 106: 70–75.
37. Singh I. Biochemistry of peroxisomes in health and disease. Mol.Cell.Biochem. 1997; 167: 1–29.
38. Řezanka T, Temina M, Tolstikov AG, Dembitsky VM. Natural microbial UV radiation filters – mycosporine-like amino acids. Folia Microbiol. 2004; 49: 339–352.
39. Jaki B, Orjala J, Sticher O. A novel extracellular diterpenoid with antibacterial activity from the cyanobacterium Nostoc commune. J.Nat.Prod. 1999; 62: 502–503.
40. Jaki B, Orjala J, Heilmann J, Linden A, Vogler B, Sticher O. Novel extracellular diterpenoids with biological activity from the cyanobacterium Nostoc commune. J.Nat.Prod. 2000b; 63: 339–343.
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How to Cite
Rawat, D., and S. Bhargava. “Bioactive Compounds from Nostoc Species”. Current Research in Pharmaceutical Sciences, Vol. 1, no. 2, Dec. 2011, pp. 48-54, https://crpsonline.com/index.php/crps/article/view/35.
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