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Гифомицеты - продуценты циклодепсипептидных соединений
Аннотация
В обзоре рассматриваются циклодепсипептидные соединения, продуцируемые гифомицетами, которые являются перспективным источником новых лекарственных средств для лечения заболеваний как инфекционной, так и патофизиологической природы.
Об авторах
М. В. Бибикова
ОАО «ГНЦА» Государственный Научный Центр по Антибиотикам, Москва; ММА им. И. М. Сеченова
Россия
Россия
Т. О. Пужевская
ОАО «ГНЦА» Государственный Научный Центр по Антибиотикам, Москва; ММА им. И. М. Сеченова
Россия
Россия
А. В. Катлинский
ОАО «ГНЦА» Государственный Научный Центр по Антибиотикам, Москва; ММА им. И. М. Сеченова
Россия
Россия
Список литературы
1. Ballard C. E., Yu H. Wang B. Recent development in depsipeptide research. Curr Med Chem 2002; 9: 471-498.
2. Шемякин М. М., Хохлов А. С., Антонов В. К. Антибиотики-депсипептиды. Химия антибиотиковю М.: 2: 1161-1172.
3. Шредер Э, Любке К. Пептиды, из-во «Мир». 1969.
4. Jestoi M., Rokka M., Rizzo A. et al. Determination of Fusarium-mycotoxins beauvericin and enniatins with liquid chromatography - tandem mass spec-trometry(LC-MS/MS). J Liq Chromatogr Technol 2005; 28: 369-381.
5. Potterat O., Wagner K., Haag H. Liquid chromatography-electrospray time-of-flight mass spectrometry for on-line accurate mass determination and identification of cyclodepsipeptides in a crude extract of the fungus Metarrhizium anisopliae. J Chromatography 2000; 872: 85-90.
6. Fotie J., Morgan R. E. Depsipeptides from microorganisms: a new class of antimalarials. Mini Rev Med Chem 2008; 11: 1088-1094.
7. Sarabia F., Chammaa S., Ruiz A. S. et al. Chemistry and biology of cyclic depsipeptides of medicinal and biological interest. Current Medicinal Chemistry, 2004; 11: 1309-1332.
8. Овчинников Ю. А., Иванов В. Т., Шкроб A. M. Мембраноактивные комплексоны, М.: 1974.
9. Dongwoo Shin, Yosup Rew, Dale L. Boger. Total synthesis and structure of the ramoplanin A1 and A3 aglycones: two minor components of the ramoplanin complex. Proceed Nat Acad Sci 2004; 101: 11977-11979.
10. Fulco P., Wenzel R. P. Ramoplanin: a topical lipoglycodepsipeptide antibacterial agent. Expert Rev Anti Infect Ther 2006; 4: 939-945.
11. Heike Brötz-Oesterhelt, Dieter Beyer, Hein-Peter Kroll et al. Disregulation of bacterial proteolytic machinery by a new class of antibiotics. Nat Med 2005; 11: 1082-1087.
12. Breukink E., de Kruijff B. Lipid II as a target for antibiotics. Nat Rev. Drug Discov 2006; 5: 321-330.
13. Xiao Fang, Kittichoat Tiyanont, Yi Zhang, et al. The mechanism of action of ramoplanin and enduracidin. Mol BioSyst 2006; 2: 69-76.
14. Pohanka A. Antifungal antibiotics from potential biocontrol microorganisms// Doctoral diss. Dept Chem SLU. Acta Univers Agricul Sueciae 2006; 47.
15. Schulz B., Boyle C., Siegfried D. S. et al. Endophytic fungi: a source of novel biologically active secondary metabolites. Mycol Res 2002; 106: 996-1004.
16. Pedras M. S., Irina Zaharia L., Ward D. E. The destruxins: synthesis, biosynthesis, biotransformation, and biological activity. Phytochemistry. 2002; 59: 579-596.
17. Gupta S., Roberts D. W., Renwick J. A. Insecticidal cyclodepsipeptides from Metarrhizium anisopliae. J Chem Soc Perkin Trans I. 1989; 2347-2357.
18. Che Y., Swenson D. C., Gloer J. B. et al. Pseudodestruxins A and B: new cyclic depsipeptides from the coprophilous fungus Nigrosabulum globo-sum. J Nat Prod 2001; 64: 555-558.
19. Lira S. P., Vita-Marques A. M., Seleghim M. H. et al. New destruxins from the marine-derived fungus Beauveria felina. J Antibiot 2006; 59: 553-563.
20. Бибикова М. В., Пужевская Т. О., Даниленко А. H. и др. Образование деструксинов копротрофным штаммом Beauveria feline №7. Антибиотики и химиотер. В печати.
21. Baute R., Deffieux G., Merlet D. et al. New insecticidal cyclodepsipeptides from the fungus Isaria felina. I. Production, isolation and insecticidal properties of isariins B, C and D. J Antibiotics 1981; 34: 1261-1265.
22. Sabareesh V., Ranganayaki R. S., Raghothama S. et al. Identification and сharacterization ofa library of microheterogeneous cyclohexadep-sipeptides from the fungus Isaria. Amer Chem Soc 2007; 70: 5.
23. Boros C., Smith C. J., Vasina Y.et al. Isolation and identification of the icosalides - cyclic peptolides with selective antibiotic and cytotoxic activities. J.Antibiotics 2006; 59: 486-489.
24. Oh D. C., Kauffman C. A., Jensen P. R., Fenical W. Induced production of emericellamides A and B from the marine-derived fungus Emericella sp. in competing co-culture. J Nat Prod 2007; 70: 515-520.
25. Tabudravu J. N., Morris L. A., Milne B. F., Jaspars M. Conformational studies of free and Li+ complexed jasplakinolide, a cyclic depsipeptide from the Fijian marine sponge Jaspis splendens. Organic Biomol Chem 2005; 3: 745-749.
26. Kaida K., Fudou R., Kameyama T. et al. New cyclic depsipeptide antibiotics clavariopsins A and B, produced by an aquatic hyphomycete Claviriopsis aquatica. J. Antibiotics 2001; 54: 22-28.
27. Lee K. K. et al. Petriellin A, a fungicidal 13-depsipeptide. J Org Chem 1995; 60: 5384-5387.
28. Sato T., Ishiyama D., Honda R. et al. Glomosporin, a novel antifungal cyclic depsipeptide from Glomospora sp. 1. Production, isolation, physico-chemical and biological activities. J Antibiotics 2000; 53: 597-602.
29. Yano T., Aoyagi A., Kozuma S. et al. Pleofungins, novel inositol phosphoryl-ceramide synthase inhibitors, from Phoma sp. SANK 13899. I. Taxonomy, fermentation, isolation, and biological activities. Ibid 2007; 60: 43-51.
30. Aoyagi A., Yano T., Kozuma S., Takatsu T. Pleofungins, novel inositol phosphorylceramide synthase inhibitors, from Phoma sp. SANK 13899. II. Structural elucidation. Ibid 2007; 60: 136-142.
31. Cerantola V., Guillas I., Roubaty C. et al. Aureobasidin A arrests growth of yeast cells through both ceramide intoxication and deprivation of essential inositolphosphorylceramides. Mol Microbiol 2009; 71: 1523-1537.
32. Yan K., Zhang Y., Huang R. et al. High-throughput synergy screening identifies microbial metabolites as combination agents for the treatment off. Natural products and antifungal drug discovery. Methods Mol Med 2007; 2.
33. Chen H. C., Chou C. K., Sun C. M., Yeh S. F. Suppressive effects of destruxin B on hepatitis B virus surface antigene gene expression in human hepatoma cells. Antiviral Res 1997; 34: 137-144.
34. Yeh S. F., Pan W., Ong G. T. Study of structure-activity correlation in destruxins, a class of cyclodepsipeptides possessing suppressive effect on the generation of hepatitis B virus surface antigen in human hepatoma cells. Biochem Biophys Res Commun 1996; 229: 65-72.
35. Hamel E., Covell D. G. Antimitotic Peptides and depsipeptide. Cur Med Chem - Anti-Cancer Agents 2002; 2: 19-53.
36. Mitsiades C. S., Ocio E. M., Pandiella A. et al. Aplidin, a marine organism - derived compound with potent antimyeloma activity in vitro and in vivo. Cancer Res 2008; 68: 5216-5225.
37. Calo L.Cytotoxic effects of the mycotoxin beauvericin on human cell lines of myeloid origin. Pharmacol Res 2004; 49: 73-77.
38. Pocsfalvi G., Di Landa G., Ferranti P. et al. Observation of non-covalent interactions between beauvericin and oligonucleotides using electrospray ionization mass spectrometry. Rapid Commun Mass Spectrom. 1997; 11: 265-272.
39. Zhan J, Burns A. M., Liu M. X. et al. Search for cell motility and angiogenesis inhibitors with potential anticancer activity: beauvericin and other constituents of two endophytic strains of Fusarium oxysporum. J Nat Prod 2007; 70: 227-232.
40. Klaric M. S., Pepeljinjak S. Beauvericin chemical and biological aspects and occurrence.Arh. Hig Rada Toxikol 2005; 5: 343-350.
41. Isaka M., Palasarn S., Lapanun S., Sriklung K. Paecilodepsipeptide A, an antimalarial and antitumor cyclohexadepsipeptide from the insect pathogenic fungus Paecilomyces cinnamomeus BCC 9616. J Nat Prod 2007; 70: 675-678.
42. Ueda H., Nakajima H., Hor Y., et al. FR901228, a novel antitumor bicyclic depsipeptide produced by Chromobacterium violaceum No. 968. I. Taxonomy, fermentation, isolation, physico-chemical and biological properties, and antitumor activity. J Antibiotics 1994; 47: 301-310.
43. Shigematsu N., Ueda H., Takase S. et al. FR901228, a novel antitumor bicyclic depsipeptide produced by Chromobacterium violaceum No. 968. II. Structure determination. Ibid 1994; 47: 311-314.
44. Dangond Fernando. (W0/2003/083067) Histone deacetylase inhibitors for the treatment of multiple sclerosis, amyotrophic sclerosis and Alzheimers disease. (Netherlands).
45. Tomoda H., Huang X. H., Cao J. et al. Inhibition of acyl-CoA: cholesterol acyltransferase activity by cyclodepsipeptide antibiotics. J Antibiotics 1992; 45: 1626-1632.
46. Ohshiro T., Rudel L. L., Omura S., Tomoda H. Selectivity of microbial acyl-CoA - cholesterol acyltransferase inhibitors toward isozymes. J Antib 2007; 69: 43-51.
47. Ohshiro T., Rudel L. L., Omura S., Tomoda H. Compared with acyl-CoA:cholesterol O-acyltransferase (ACAT) 1 and lecithin: cholesterol acyltransferase (ACAT2) displays the greatest capacity to differentiate cholesterol from sitosterol. J Biol Chem 2003.
48. Namatame I. H. Tomoda, Satoshi Omura. Antiatherogenic activity of fungal beauveriolides, inhibitors of lipid droplet accumulation in macrophages. J Antibiotics 1996; 49: 73-77.
49. Jegorov A., Sedmera P., Matha V. Beauverolides L and La from Beauveria tenella and Paecilomyces fumosoroseus. Phytochemystry 1994; 37: 1300-1303.
50. Matsuda D., Namatame I., Tomoda H. et al. New beauveriolides produced by amino acid-supplemented fermentation of Beauveria sp. FO-6979. J Antibiotics 2004; 57: 1-9.
51. Naganuma S., Kuzuya N., Sakai K. et al. Inhibition of the accumulation of lipid droplets in macrophage J774 by bafilomycin B1 and destruxin E. Biochim Biophys Acta 1992; 1126: 41-48.
52. Nagai К., Woo J.T. Destruxins, cyclodepsipeptides block the formation of actin rings and prominent clear zones and ruffled borders in osteoclasts. Bone 2003; 33: 443-455.
53. Muroi M., Shiragami N., Takatsuki A. Destruxin B, a specific and readily reversible inhibitor of vacular-type H+ translocation ATPase. Biochem Biophys. Res Com 1994; 205: 1555-1563.
54. Hih-Yung Tang, Yi-Wen Chen et al. Beauvericin activated Ca2+- activated CI- current and deaths in Xenopus oocytes via influx of extracellular Ca2+. Chem Res Toxicol 2002; 15: 854-860.
55. Tsunoo A., Kamijo M. Non-cyclic AMP-dependent, positive inotropic cyclodepsipeptides with negative chronotropy1. J Pharm Exper Ther 1999; 290: 1006-1012.
56. Akinobu Tsunoo, Masayuki Kamijo, Naoki Taketomo et al. Roseocardin, a novel cardiotonic cyclodepsipeptide from Trichothecium roseum TT103. J Antibiiotics 1997; 50: 1007-1013.
57. Cai Р., Smith D., Katz B. et al. Destruxin-A4 chlorohydrin, a novel destruxin from fugus OS-F68576: isolation, structure determination, and biological activity as an inducer of erythropoietin. J Nat Prod 1998; 61: 290-293.
58. Hamano K., Kinoshita M., Furuya K. et al. Leualacin, a novel calcium blocker from Hapsidospora irregularis I. Taxonomy, fermentation, isolation. physico-chemical and biological properties. J Antibiotics 1992; 45: 899.
59. Pal S., St Leger R. J., Wu L. P. Fungal peptide destruxin A plays a specific role in suppressing the innate immune response in Drosophila melanogaster. J Biol Chem 2007; 282: 8969-8977.
Для цитирования:
Бибикова М.В., Пужевская Т.О., Катлинский А.В. Гифомицеты - продуценты циклодепсипептидных соединений. Антибиотики и Химиотерапия. 2010;55(3-4):35-44.
For citation:
Bibikova M.V., Puzhevskaya T.O., Katlinsky A.V. Hyphomycetes, as Organisms Producing Cyclodepsipeptides. Antibiotics and Chemotherapy. 2010;55(3-4):35-44. (In Russ.)
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