Herbimycins D-F, Ansamycin Analogues from Streptomyces Sp. RM-7-15

Overview

Journal J Nat Prod

Date 2013 Aug 17

PMID 23947794

Citations 29

Authors

Khaled A Shaaban

Xiachang Wang

Sherif I Elshahawi

Larissa V Ponomareva

Manjula Sunkara

Gregory C Copley

James C Hower

Andrew J Morris

Madan K Kharel

Jon S Thorson

Affiliations

Soon will be listed here.

Abstract

Bacterial strains belonging to the class actinomycetes were isolated from the soil near a thermal vent of the Ruth Mullins coal fire (Appalachian Mountains of eastern Kentucky). High-resolution electrospray ionization mass spectrometry and ultraviolet absorption profiles of metabolites from one of the isolates (Streptomyces sp. RM-7-15) revealed the presence of a unique set of metabolites ultimately determined to be herbimycins D-F (1-3). In addition, herbimycin A (4), dihydroherbimycin A (TAN 420E) (7), and the structurally distinct antibiotic bicycylomycin were isolated from the crude extract of Streptomyces sp. RM-7-15. Herbimycins A and D-F (1-3) displayed comparable binding affinities to the Hsp90α. While the new analogues were found to be inactive in cancer cell cytotoxicity and antimicrobial assays, they may offer new insights in the context of nontoxic ansamycin-based Hsp90 inhibitors for the treatment of neurodegenerative disease.

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References

Funayama S, Anraku Y, Mita A, Yang Z, Shibata K, Komiyama K . Structure-activity relationship of a novel antitumor ansamycin antibiotic trienomycin A and related compounds. J Antibiot (Tokyo). 1988; 41(9):1223-30. DOI: 10.7164/antibiotics.41.1223. View

Ramos-E-Silva M, Rebello P . Leprosy. Recognition and treatment. Am J Clin Dermatol. 2001; 2(4):203-11. DOI: 10.2165/00128071-200102040-00001. View

Kim C, Yu T, Fryhle C, Handa S, Floss H . 3-Amino-5-hydroxybenzoic acid synthase, the terminal enzyme in the formation of the precursor of mC7N units in rifamycin and related antibiotics. J Biol Chem. 1998; 273(11):6030-40. DOI: 10.1074/jbc.273.11.6030. View

Wu C, Jang J, Woo M, Ahn J, Kim J, Hong Y . Enzymatic glycosylation of nonbenzoquinone geldanamycin analogs via Bacillus UDP-glycosyltransferase. Appl Environ Microbiol. 2012; 78(21):7680-6. PMC: 3485733. DOI: 10.1128/AEM.02004-12. View

Lundgren K, Zhang H, Brekken J, Huser N, Powell R, Timple N . BIIB021, an orally available, fully synthetic small-molecule inhibitor of the heat shock protein Hsp90. Mol Cancer Ther. 2009; 8(4):921-9. DOI: 10.1158/1535-7163.MCT-08-0758. View

Mochizuki J, Kobayashi E, Furihata K, Kawaguchi A, Seto H, Otake N . New ansamycin antibiotics, naphthoquinomycins A and B, inhibitors of fatty acid synthesis in Escherichia coli. J Antibiot (Tokyo). 1986; 39(1):157-61. DOI: 10.7164/antibiotics.39.157. View

OKeefe J, Henke K, Hower J, Engle M, Stracher G, Stucker J . CO(2), CO, and Hg emissions from the Truman Shepherd and Ruth Mullins coal fires, eastern Kentucky, USA. Sci Total Environ. 2010; 408(7):1628-33. DOI: 10.1016/j.scitotenv.2009.12.005. View

Bernardo J, Ossola R, Spotila J, Crandall K . Interspecies physiological variation as a tool for cross-species assessments of global warming-induced endangerment: validation of an intrinsic determinant of macroecological and phylogeographic structure. Biol Lett. 2007; 3(6):695-8. PMC: 2121324. DOI: 10.1098/rsbl.2007.0259. View

Sepkowitz K, Raffalli J, Riley L, Kiehn T, Armstrong D . Tuberculosis in the AIDS era. Clin Microbiol Rev. 1995; 8(2):180-99. PMC: 172855. DOI: 10.1128/CMR.8.2.180. View

10.

Zhao H, Michaelis M, Blagg B . Hsp90 modulation for the treatment of Alzheimer's disease. Adv Pharmacol. 2012; 64:1-25. DOI: 10.1016/B978-0-12-394816-8.00001-5. View

11.

Lalloo U, Ambaram A . New antituberculous drugs in development. Curr HIV/AIDS Rep. 2010; 7(3):143-51. DOI: 10.1007/s11904-010-0054-4. View

12.

Biamonte M, Van de Water R, Arndt J, Scannevin R, Perret D, Lee W . Heat shock protein 90: inhibitors in clinical trials. J Med Chem. 2010; 53(1):3-17. DOI: 10.1021/jm9004708. View

13.

Campbell E, Korzheva N, Mustaev A, Murakami K, Nair S, Goldfarb A . Structural mechanism for rifampicin inhibition of bacterial rna polymerase. Cell. 2001; 104(6):901-12. DOI: 10.1016/s0092-8674(01)00286-0. View

14.

Ni S, Wu L, Wang H, Gan M, Wang Y, He W . Thiazinogeldanamycin, a new geldanamycin derivative produced by Streptomyces hygroscopicus 17997. J Microbiol Biotechnol. 2011; 21(6):599-603. View

15.

Floss H, Yu T . Rifamycin-mode of action, resistance, and biosynthesis. Chem Rev. 2005; 105(2):621-32. DOI: 10.1021/cr030112j. View

16.

Kasik J, Monick M, Thompson J . Immunosuppressant activity of the ansamycins. Antimicrob Agents Chemother. 1976; 9(3):470-3. PMC: 429554. DOI: 10.1128/AAC.9.3.470. View

17.

Schlegel B, Hanel F, Gollmick F, Saluz H, Grafe U . New quinones and hydroquinones from Malbranchea cinnamomea HKI 286 and HKI 296 and interaction with Tax/CREB expression system in yeast. J Antibiot (Tokyo). 2004; 56(11):917-22. DOI: 10.7164/antibiotics.56.917. View

18.

Yang Y, Fu X, Li L, Zeng Y, Li C, He Y . Naphthomycins L-N, ansamycin antibiotics from Streptomyces sp. CS. J Nat Prod. 2012; 75(7):1409-13. DOI: 10.1021/np300109s. View

19.

Hosokawa N, Naganawa H, Hamada M, Iinuma H, Takeuchi T, Tsuchiya K . New triene-ansamycins, thiazinotrienomycins F and G and a diene-ansamycin, benzoxazomycin. J Antibiot (Tokyo). 2000; 53(9):886-94. DOI: 10.7164/antibiotics.53.886. View

20.

Cricchio R, Antonini P, Sartori G . Thiazorifamycins. III. Biosynthesis of rifamycins P, Q and verde, novel metabolites from a mutant of Nocardia mediterranea. J Antibiot (Tokyo). 1980; 33(8):842-6. DOI: 10.7164/antibiotics.33.842. View