Abstract
Several streptothricin antibiotics have been studied by tandem mass spectrometry. The dominant product ions were derived from the C7-N bond cleavage which lead to lose streptolidine from the [M+H]+. The fragmentation pathways of key ions were described and certained by parent scan. According to the generalized principles, streptothricin isomers could be distinguished easily by the difference of CID spectra. A facile method based on ion-pair RP-HPLC coupled with electrospray ionization tandem mass spectrometry has been established for the analysis of streptothricins in the fermentation broth of Streptomyces qinlingensis. A total of 19 streptothricinlike compounds were identified or tentatively characterized based on their mass spectral data, and in which 11 were the first reported compounds. This could be used as an important de-replication method in the programs of screening novel antibiotics.
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Waksman SA, Woodruff HB . Streptothricin, a new selective bacteriostatic and bactericidal agent particularly against Gram-negative bacteria. Proc Soc Exptl Biol Med 49: 207–209 ( 1942)
Van Tamelen EE, Dyer JR, Whaley HA, Carter HE . Constitution of the streptolin-streptothricin group of Streptomyces antibiotics. J Am Chem Soc 83: 4295–4296 ( 1961)
Haupt I, Jonak J, Rychlik I, Thrum H . Action of streptothricin F on ribosomal functions. J Antibiot 33: 636–641 ( 1980)
Zhu CX . Zhongshengmycin, a new agro-antibiotics. Fine and Specialty Chemicals (In Chinese) 16: 14–17 ( 2002)
Richard HB . Antimicrobials from actinomycetes: Back to the future. Microbe 2: 125–131 ( 2007)
Terekhova LP, Novozhenov Miu, Tolstykh IV, Brazhnikova MG . Early identification of streptothricin group antibiotics. Antibiot Khimioter 36: 15–17 ( 1991)
Stapley EO . Cross-resistance studies and antibiotic identification. Appl Microbio 6: 392–398 ( 1958)
Mehta RJ, Oh YK, Sitrin RD, Shultis EA . Nash CH 3rd . Microbial resistances: a predictive test for streptothricin antibiotics. J Antibiot 34: 1501–1503 ( 1981)
Khokhlov AS, Shutova KJ . Chemical structure of streptothricins. J Antibiot 25: 501–508 ( 1972)
Kusumoto S, Kambayashi S, Imaoka S, Shima K, Shiba T . Total chemical structure of streptothricin. J Antibiot 35: 925–927 ( 1982)
Kim BT, Lee JY, Lee YY, Kim OY, Chu JH, Goo YM . N-methylstreptothricin D—a new streptothricin-group antibiotic from a Streptomyces spp. J Antibiot 47: 1333–1336 ( 1994)
Hisamoto M, Inaoka Y, Sakaida Y, Kagazaki T, Enokida R, Okazaki T, Haruyama H, Kinoshita T, Matsuda K . A-53930A and B, novel N-type Ca2+ channel Blockers [J]. J Antibiot 51: 607–617 ( 1998)
Ji ZQ, Wang MA, Zhang JW, Wei SP, Wu WJ . Two new members of streptothricin class antibiotics from Streptomyces qinlingensis sp. nov. J Antibiot 60: 739–744 ( 2008)
Ando T, Miyashiro S, Hirayama K, Kida T, Shibai H, Murai A, Udaka S . New streptothricin-group antibiotics, AN-201 I, II and III. J Antibiot 40: 1140–1145 ( 1987)
Inamori Y, Tominaga H, Okuno M, Sato H, Tsujibo H . Antimicrobial activity on plant-pathogenic microorganisms and phytogrowth-inhibitory activity of streptothricin antibiotics, racemomycin-A and -C. Chem Pharm Bull 36: 1577–1580 ( 1988)
Taniyama H, Sawada Y, Kitagawa T . Studies on the inactivation and regeneration of streptothricin. J Antibiot 24: 662–666 ( 1971)
Yoshimitsu H, Nobuyasu M, Miwa K . A novel enzyme conferring streptothricin resistance alters the toxicity of streptothricin D from broad-spectrum to bacteria-specific. J Biol Chem 281: 16842–16848 ( 2006)
Hu PF, Edward KC, Sean B, George J, James M, Richard BH . Collisionally activated dissociations of aminocyclitolaminoglycoside antibiotics and their application in the identification of a new compound in Tobramycin samples. J Am Soc Mass Spectrom 11: 200–209 ( 2000)
Sawada Y, Sakamoto H, Taniyama H . Studies on chemical modification of streptothricin-group antibiotics. III. Pritial N-acetylation of racemomycins and their biological activity. Yakugaku Zasshi 94: 176–180 ( 1974)
Sawada Y, Taniyama H . Studies on chemical modification fo streptothricin-group antibiotics. IV. Preparation of β-N-acetyl-racemomycin-A and its antimicrobial activity. Yakugaku Zasshi 94: 264–266 ( 1974)
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Ji, Z., Wei, S., Zhang, J. et al. Identification of Streptothricin Class Antibiotics in the Earlystage of Antibiotics Screening by Electrospray Ionization Mass Spectrometry. J Antibiot 61, 660–667 (2008). https://doi.org/10.1038/ja.2008.93
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DOI: https://doi.org/10.1038/ja.2008.93
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