JOURNAL OF THE CZECH PHARMACEUTICAL SOCIETY AND THE SLOVAK PHARMACEUTICAL SOCIETY

Čes. slov. farm. 2012, 61(3):107-114

Microbial secondary metabolites as inhibitors of pharmaceutically important transferases and oxidoreductases

Eva Buchtová*, Mária Šturdíková
Slovenská technická univerzita, Ústav biotechnológie a potravinárstva, Fakulta chemickej a potravinárskej technológie

Microorganisms are known for their production of an enormous variety of biologically active secondary metabolites including antibiotics, immunosuppressants and anticancer agents. These compounds have many important biological activities used in the clinical practice in drug treatment of cancer, inflammatory, autoimmune diseases and metabolic disorders. The science and medicine research have been yielded hundreds items of useful knowledge in the therapy of many serious human diseases caused by pathophysiological mechanisms of enzymes. Many substances were discovered already in the last century, but the research of their potential and various modifications improving their prospects of therapeutic use still continues. The new knowledge about mechanisms of the action and enzyme inhibitors in the field of enzymology gives space in drug discovery and development of safer and more effective pharmacotherapy.

Keywords: secondary metabolites; microbial producers; enzyme inhibitors; pathophysiology of enzyme reactions

Received: April 13, 2012; Accepted: May 9, 2012; Published: March 1, 2012  Show citation

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Buchtová E, Šturdíková M. Microbial secondary metabolites as inhibitors of pharmaceutically important transferases and oxidoreductases. Čes. slov. farm. 2012;61(3):107-114.
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References

  1. Holková I., Bezáková L., Vanko M., Bilka F., Obložinský M.: Lipoxygenázy a ich význam v biochemických procesoch v rastlinných organizmoch. Chem. Listy 2009; 103, 475-495.
  2. Chen X., Yang Y., Ma B., Zhang S., He M., Gui D., Hussain S., Jing Ch., Zhu Ch., Yu Q., Liu Y.: Design and synthesis of potent and selective aldose reductase inhibitors based on pyridylthiadiazine scaffold. Eur. J. Med. Chem. 2011; 46, 1536-1544. Go to original source... Go to PubMed...
  3. Alexiou P., Pegklidou K., Chatzopoulou M., Nicolaou I., Demopoulos V. J.: Aldose reductase enzyme and its implication to major health problems of the 21(st. century. Curr. Med. Chem. 2009; 16, 734-752. Go to original source... Go to PubMed...
  4. Oyama T., Miyasita Y., Watanabe H., Shirai K.: The role of polyol pathway in high glucose-induced endothelial cell damages. Diabetes Res. Clin. Pract. 2006; 73, 227-234. Go to original source... Go to PubMed...
  5. Fujita T., Funako T., Hayashi H.: 8-Hydroxydaidzein, an Aldose Reductase Inhibitor form Okara Fermented with Aspergillus sp. HK-388. Biosci. Biotechnol. Biochem. 2004; 68, 1588-1590. Go to original source... Go to PubMed...
  6. Tai S. S.-K., Lin Ch.-G., Wu M.-H., Chang T.-S.: Evaluation of Depigmenting Activity by 8-Hydroxydaidzein in Mouse B16 Melanoma Cells and Human Volunteers. Int. J. Mol. Sci. 2009; 10, 4257-4266. Go to original source... Go to PubMed...
  7. Xu B.-J., Jia X.-Q., Gu L.-J., Sung Ch.-K.: Review on the qualitative and quantitative analysis of the mycotoxin citrinin. Food Contr. 2006; 17, 271-285. Go to original source...
  8. Sankawa, U., Ebizuka, Y., Noguchi, H., Isikawa, Y., Kitaghawa, S., Yamamoto, Y., Kobayashi, T., Iitak, Y.: Biosynthesis of citrinin in Aspergillus terreus. Tetrahedron 1983; 39, 3583-3591. Go to original source...
  9. Hajjaj H., Klaebe A., Loret M., Goma G., Blanc, P. J., Francois J.: Biosynthetic Pathway of Citrinin in the Filamentous Fungus Monascus ruber as Revealed by 13C Nuclear Magnetic Resonance. Appl. Environ. Microbiol. 1999; 65, 311-314. Go to original source... Go to PubMed...
  10. Devi P., D'Souza, L., Kamat, T., Rodrigues, C., Naik, Ch. G.: Batch culture fermentation of Penicillium chrysogenum and a report on the isolation, purification and antibiotic activity of citrinin. Indian J. Mar. Sci. 2009; 38, 38-44.
  11. Dong Y., Yang J., Ren X., Zhang H., He J.: New aldose reductase inhibitors N99-596 A and B from Streptomyces. J. Antibiot. 2005; 58, 737-739. Go to original source... Go to PubMed...
  12. Deruiter J., Jacyno J. M., Cutler H. G., Davis R. A.: Studies on aldose reductase inhibitors from fungi. 2. Moniliformin and small ring analogs. J. Enzym. Inhib. 1993; 7, 249-256. Go to original source...
  13. Chidananda C., Rao L. J. M., Sattur A. P.: Sclerotiorin, from Penicillium frequentans, a potent inhibitor of aldose reductase. Biotechnol. Lett. 2006; 28, 1633-1636. Go to original source... Go to PubMed...
  14. Rao S. K. C., Divakar S., Naveen Babu K., Appu Rao A. G., Karanth N. G., Sattur A. P.: Nigerloxin, a novel inhibitor of aldose reductase and lipoxygenase with free radical scavenging activity from Aspergillus niger CFR-W-105. J. Antibiot. 2003; 56, 789-793. Go to original source... Go to PubMed...
  15. Rao K. C. S., Divakar S., Srinivas M., Babu K. N., Karanth N. G., Sattur A. P.: Asperaldin, a new aldose reductase inhibitor from Aspergillus niger CFR-1046. I. Fermentation, isolation and characterization. J. Antibiot. 2003; 56, 173-176. Go to original source... Go to PubMed...
  16. Nishikawa M., Tsurumi Y., Murai H., Yoshida K., Okamoto M., Takase S., Tanaka H., Hirota H., Hashimoto M., Kohsaka M.: WF-2421, a new aldose reductase inhibitor produced from a fungus, Humicola grisea. J. Antibiot. 1991; 44, 130-135. Go to original source... Go to PubMed...
  17. Sun W. S., Lee H. S., Park J. M., Kim S. H., Yu J. H., Kim J. H.: YUA001, a novel aldose reductase inhibitor isolated from alkalophilic Corynebacterium sp. YUA25 II. Chemical modification and biological activity. J. Antibiot. 2001; 54, 827-830. Go to original source... Go to PubMed...
  18. McTaggert S. J.: Isoprenylated proteins. Cell. Mol. Life Sci. 2006, 63, 255-267. Go to original source... Go to PubMed...
  19. Wang C. Y., Liu P. Y., Liao J. K.: Pleiotropic effects of statin therapy: molecular mechanisms and clinical results. Trends. Mol. Med. 2008; 14, 37-44. Go to original source... Go to PubMed...
  20. Dudakovic A., Wiemer A. J., Lamb K. M., Vonnahme L. A., Dietz S. E., Hohl R. J.: Inhibition of geranylgeranyl diphosphate synthase induces apoptosis through multiple mechanisms and displays synergy with inhibition of other isoprenoid biosynthetic enzymes. J. Pharmacol. Exp. Therapeut. 2008; 324, 1028-1036. Go to original source... Go to PubMed...
  21. Konya A., Jekkel A., Sutö J., Salat J.: Optimization of compactin fermentation. J. Ind. Microbiol. Biotechnol. 1998; 20, 150-152. Go to original source...
  22. Shaligram N. S., Singh S. K., Singhal R. S., Szakacs G., Pandey A.: Effect of precultural and nutritional parameters on compactin production by solid-state fermentation. J. Microbiol. Biotechnol. 2009; 19, 690-697. Go to original source... Go to PubMed...
  23. Garrett I. R., Gutierrez G. E., Rossini G., Nyman J., McCluskey B., Flores A., Mundy, G. R.: Locally delivered lovastatin nanoparticles enhance fracture healing in rats. J. Orthop. Res. 2007; 25, 1351-1357. Go to original source... Go to PubMed...
  24. Crick D. C., Andres D. A., Danesi R., Macchia M., Waechter C. J.: Geranylgeraniol overcomes the block of cell proliferation by lovastatin in C6 glioma cells. J. Neurochem. 1998; 70, 2397-2404. Go to original source... Go to PubMed...
  25. Xia Z., Tan M. M., Wong W. W. L., Dimitroulakos J., Minden M. D., Penn L. Z.: Blocking protein geranylgeranylation is essential for lovastatin-induced apoptosis of human acute myeloid leukemia cells. Leukemia 2001; 15, 1398-1407. Go to original source... Go to PubMed...
  26. Seenivasan A., Subhagar S., Aravindan R., Viruthagiri T.: Microbial production and biomedical applications of lovastatin. Indian J. Pharmaceut. Sci. 2008, 70, 701-709. Go to original source... Go to PubMed...
  27. Manzoni M., Rollini M.: Biosynthesis and biotechnological production of statins by filamentous fungi. Appl. Microbiol. Biotechnol. 2002; 58, 555-564. Go to original source... Go to PubMed...
  28. Alberts A. W., Chen J., Kuron G., Hunt V., Huff J., Hoffman C., Rothrock J., Lopez M., Joshua H., Harris E., Patchett A., Monaghan R., Currie S., Stapley E., Albers-Schonberg G, Hensens O., Hirshfield J., Hoogsteen K., Liesch J., Springer J.: Mevinolin: A Highly Competitive Inhibitor of Hydroxymethylglutaryl-Coenzyme A Reductase and a Cholesterol Lowering Agent. Proc. Natl. Acad. Sci. USA 1980; 77, 3957-3961. Go to original source... Go to PubMed...
  29. Yan J., Xu Y., Zhu C., Zhang L., Wu A., Yang Y., Xiong Z., Deng C., Huang X. F., Yenari M. A., Yang Y. G., Ying W., Wang Q.: Simvastatin Prevents Dopaminergic Neurodegeneration in Experimental Parkinsonian Models: The Association with Anti-Inflammatory Responses. PLoS ONE 2011, 6, e20945. http://www.plosone.org. Go to original source... Go to PubMed...
  30. Kűhn H., Belkner J., Zaiss S., Fährenklemper T., Wohlfeil S.: Involvement of 15-lipoxygenase in early stages of atherogenesis. J. Exp. Med. 1994; 179, 1903-1911.
  31. Kelavkar U. P., Nixon J. B., Cohen C., Dillehay D., Eling T. E., Badr K. F.: Overexpression of 15-lipoxygenase-1 in PC-3 human prostate cancer cells increases tumorigenesis. Carcinogenesis 2002; 22, 1765-1773. Go to original source... Go to PubMed...
  32. Jefferson Jr. W. E.: The isolation and characterization of asperenone, a new phenylpolyene from Aspergillus niger. Biochemistry 1967; 6, 3479-3484. Go to original source... Go to PubMed...
  33. Yu J., Tamura G., Takahashi N., Arima K.: Asperyellone, a new yellow pigment of Aspergillus awamori and Aspergillus niger. Agr. Biol. Chem. 1967; 31, 831-836. Go to original source...
  34. Ayer W. A., Muir D. J., Chakravarty P.: Phenolic and other metabolites of Phellinus pini, a fungus pathogenic to pine. Phytochemistry 1996; 42, 1321-1324. Go to original source...
  35. Rao K. C., Divakar S., Appu Rao A. G., Karanth N. G., Suneetha W. J., Krishnakantha T. P., Sattur A. P.: Asperenone: an inhibitor of 15-lipoxygenase and of human platelet aggregation from Aspergillus niger. Biotechnol. Lett. 2002; 24, 1967-1970. Go to original source...
  36. Chidananda C., Kumar C. M., Sattur A. P.: Strain improvement of Aspergillus niger for the enhanced production of asperenone. Indian. J. Microbiol. 2008; 48, 274-278. Go to original source... Go to PubMed...
  37. Chidananda C., Sattur A. P.: Sclerotiorin, a novel inhibitor of lipoxygenase from Penicillium frequentans. J. Agr. Food Chem. 2007; 55, 2879-2883. Go to original source... Go to PubMed...
  38. Lucas E. M. F., Machado Y., Ferreira A. A., Dolabella L. M. P., Takahashi J. A.: Improved production of pharmacologically-active sclerotiorin by Penicillium sclerotiorum. Trop. J. Pharmaceut. Res. 2010; 9, 365-371. Go to original source...
  39. Rao S. K. C., Divakar S., Naveen Babu K., Appu Rao A. G., Karanth N. G., Sattur A. P.: Nigerloxin, a novel inhibitor of aldose reductase and lipoxygenase with free radical scavenging activity from Aspergillus niger CFR-W-105. J. Antibiot. 2003; 56, 789-793. Go to original source... Go to PubMed...
  40. Hasan H. A. H.: Production and Determination of Nigerloxin by Aspergillus niger. Int. J. Agr. Biol. 2007; 9, 315-318.
  41. Chakradhar D., Javeed S., Sattur P. A.: Studies on the production of nigerloxin using agro-industrial residues by solid-state fermentation. J. Ind. Microbiol. Biotechnol. 2009; 36, 1179-1187. Go to original source... Go to PubMed...
  42. Esposito F., Kharlamova T., Distinto S., Zinzula L., Cheng Y. C., Dutschman G., Floris G., Markt P., Corona A., Tramontano E.: Alizarine derivatives as new dual inhibitors of the HIV-1 reverse transcriptase-associated DNA polymerase and RNase H activities effective also on the RNase H activity of non-nucleoside resistant reverse transcriptases. FEBS J. 2011; 278, 1444-1457. Go to original source... Go to PubMed...
  43. Kaul A., Maltese W. A.: Killing of Cancer Cells by the Photoactivatable Protein Kinase C Inhibitor, Calphostin C, Involves Induction of Endoplasmic Reticulum Stress. Neoplasia 2009; 11, 823-834. Go to original source... Go to PubMed...
  44. Isel C., Ehresmann Ch., Marquet R.: Initiation of HIV Reverse Transcription. Viruses 2010; 2, 213-243. Go to original source... Go to PubMed...
  45. Lai M. T., Munshi V., Touch S., Tynebor R. M., Tucker T. J., McKenna P. M., Williams T. M., DiStefano D. J.: Antiviral Activity of MK-4965, a Novel Nonnucleoside Reverse Transcriptase Inhibitor. Antimicrob. Agents Chemother. 2009; 53, 2424-2431. Go to original source... Go to PubMed...
  46. Demain A. L., Somkuti G. A., Hunter-Cavera J. C., Rossmoore H. W.: Novel microbial products for medicine and agriculture. Netherlands: Elsevier, 1989.
  47. Davidson R. N., Boerb M., Ritmeijerb K.: Paromomycin. Trans. Roy. Soc. Trop. Med. Hyg. 2009; 103, 653-660. Go to original source... Go to PubMed...
  48. Kitahara N., Haruyama H., Hata T., Takahashi S.: The structures of thielavins A, B and C. Prostaglandin synthetase inhibitors from fungi. J. Antibiot. 1983; 36, 599-600. Go to original source... Go to PubMed...
  49. Sakemi S., Hirai H., Ichiba T., Inagaki T., Kato Y., Kojima N., Nishida H., Parker J. C., Saito T., Tonai-Kachi H., Volkenburg M. A., Yoshikawa N., Kojima Y.: Thielavins as glucose-6-phosphatase (G6Pase. inhibitors: producing strain, fermentation, isolation, structural elucidation and biological activities. J. Antibiot. 2002; 55, 941-951. Go to original source... Go to PubMed...
  50. Mani N., Sanchet P., Jiang Z. D., McNaney C., DeCenzo M., Knighti B., Stankis M., Kuranda M., Rothenstein D. M.: Screening systems for detecting inhibitors of cell wall transglycosylation in Enterococcus. J. Antibiot. 1998; 51, 471-479. Go to original source... Go to PubMed...
  51. Chen J. L.-Y., Sperry J., Ip, N. Y., Brimble M. A.: Natural products targeting telomere maintenance. Med. Chem. Commun. 2011; 2, 229-245. Go to original source...
  52. Rao K. V., Cullen W. P.: Streptonigrin, an antitumour substance. I. Isolation and characterization. Antibiot. Annu. 1959; 7, 950-953.
  53. Société des usines chimiques de Rhône-Poulenc, GB Patent 872261, 1961, Chem. Abstr. 1961; 55, 25158a.
  54. Kudrina E. S., Ol'khovatova O. L., Murav'eva L. I., Gauze G. F.: Systematic position and variability of the producent of antitumor antibiotic bruneomycin. Antibiotiki 1966; 11, 400-405.
  55. Brazhnikova M. G., Ponomarenko I. N., Kovsharova E. B., Kruglyak E. B., Proshlyakova V. V.: Study of bruneomycin formed by Actinomyces albus var. bruneomycini and its identification with streptonigrin. Antibiotiki 1968; 13, 99-102.
  56. Bolzán A. D., Bianchi M. S.: Genotoxicity of streptonigrin: a review. Mutat. Res. Rev. Mutat. Res. 2001; 488, 25-37. Go to original source... Go to PubMed...
  57. Mesak L. R., Qi S., Villanueva I., Miao V., Davies J.: Staphylococcus aureus promoter-lux reporters for drug discovery. J. Antibiot. (Tokyo) 2010; 63, 492-498. Go to original source... Go to PubMed...
  58. Serova M., Ghoul A., Benhadji K. A., Cvitkovic E., Faivre S., Calvo F., Lokiec F., Raymond E.: Preclinical and clinical development of novel agents that target the protein kinase C family. Semin. Oncol. 2006; 33, 466-478. Go to original source... Go to PubMed...
  59. Martiny-Baron G., Fabbro D.: Classical PKC isoforms in cancer. Pharmacol. Res. 2007; 55, 477-486. Go to original source... Go to PubMed...
  60. Mackay H. J., Twelves C. J.: Targeting the protein kinase C family: are we there yet? Nat. Rev. Canc. 2007; 7, 554-562. Go to original source... Go to PubMed...
  61. Kaul A., Maltese W. A.: Killing of Cancer Cells by the Photoactivatable Protein Kinase C Inhibitor, Calphostin C, Involves Induction of Endoplasmic Reticulum Stress. Neoplasia 2009; 11, 823-834. Go to original source... Go to PubMed...
  62. Kobayashi E., Ando K., Nakano H., Iida T., Ohno H., Morimotot M., Tamaoki T.: Calphostins (UCN - 1028., novel and specific inhibitors of protein kinase C. I. Fermentation, isolation, physico-chemical properties and biological activities. J. Antibiot. 1989; 42, 1470-1474. Go to original source... Go to PubMed...
  63. Olivo M., Ali-Seyed M.: Apoptosis signalling mechanisms in human cancer cells induced by calphostin-PDT. Int. J. Oncol. 2007; 30, 537-548. Go to original source...
  64. Chiarini A., Whitfield J. F., Pacchiana R., Armato U., Dal Pra I.: Photoexcited calphostin C selectively destroys nuclear lamin B1 in neoplastic human and rat cells - a novel mechanism of action of a photodynamic tumor therapy agent. Biochim. Biophys. Acta 2008; 1783, 1642-1653. Go to original source... Go to PubMed...
  65. Guo B., Hembruff S. L., Villeneuve D. J., Kirwan A. F, Parissenti A. M.: Potent killing of paclitaxel- and doxorubicin-resistant breast cancer cells by calphostin C accompanied by cytoplasmic vacuolization. Breast Canc. Res. Treat. 2003; 82, 125-141. Go to original source... Go to PubMed...
  66. Trindade-Silva A. E., Lim-Fong G. E., Sharp K. H., Haygood M. G.: Bryostatins: biological context and biotechnological prospects. Curr. Opin. Biotechnol. 2010; 21, 834-842. Go to original source... Go to PubMed...
  67. Wender P. A., Baryza J. L., Brenner S. E., DeChristopher B. A., Loy B. A., Schrier A. J., Verma V. A.: Design, synthesis, and evaluation of potent bryostatin analogs that modulate PKC translocation selectivity. Proc. Natl. Acad. Sci. 2011; 108, 6721-6726 (http://www.pnas.org). Go to original source... Go to PubMed...
  68. Gully Ch. P., Zhang F., Chen J., Yeung J. A., Velazquez-Torres G., Wang E., Yeung S.-Ch. J., Lee M.-H.: Antineoplastic effects of an Aurora B kinase inhibitor in breast cancer. Mol. Canc. 2010; 9(42). http://www.molecular-cancer.com) Go to original source... Go to PubMed...
  69. Ayer S. W., McInnes A. G., Thibault P., Walter J. A., J. L. Doull Parnell, T., Vining L. C.: Jadomycin, a novel 8i/-benz[6]oxazolo[3,2-]phenanthridine antibiotic from Streptomyces venezuelaeISP5230. Tetrahedron Lett. 1991; 32, 6301-6304. Go to original source...
  70. Fu D.-H., Jiang W., Zheng J.-T., Zhao G.-Y., Li Y., Yi H., Li Z.-R., Jiang J.-D., Yang K.-Q., Wang Y., Si S.-Y.: Jadomycin B, an Aurora-B kinase inhibitor discovered through virtual screening. Mol. Canc. Therapeut. 2008; 7, 2386-2393. Go to original source... Go to PubMed...
  71. Jakeman D. L., Bandi S., Graham C. L., Reid T. R., Wentzell J. R., Douglas S. E.: Antimicrobial Activities of Jadomycin B and Structurally Related Analogues. Antimicrob. Agents Chemother. 2009; 53, 1245-1247. Go to original source... Go to PubMed...
  72. Aly A. H., Debbab A., Edrada-Ebel R. A., Müller W. E. G., Kubbutat M. H. G., Wray V., Ebel R., Proksch P.: Protein kinase inhibitors and other cytotoxic metabolites from the fungal endophyte Stemphylium botryosum isolated from Chenopodium album. Mycosphere 2010; 1, 153-162.




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