Preview

Антибиотики и Химиотерапия

Расширенный поиск
Доступ открыт Открытый доступ  Доступ закрыт Доступ платный или только для Подписчиков

Гифомицеты - продуценты циклодепсипептидных соединений

Полный текст:

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


Т. О. Пужевская
ОАО «ГНЦА» Государственный Научный Центр по Антибиотикам, Москва; ММА им. И. М. Сеченова
Россия


А. В. Катлинский
ОАО «ГНЦА» Государственный Научный Центр по Антибиотикам, Москва; ММА им. И. М. Сеченова
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.)

Просмотров: 41


ISSN 0235-2990 (Print)