Stoffwechselprodukte von Mikroorganismen

Abstract

Streptomyces flaveolus, strain Tü 1240 produces besides Tirandamycin A, a hitherto unknown antibiotic, which is closely related to Tirandamycin A. The new antibiotic Tirandamycin B contains one additional hydroxylgroup. Both antibiotics exhibit a similar antimicrobial spectrum and they seem to have the same mechanism of action. According to the data obtained from mass spectrometry, 13C-and 1H-NMR spectra formula II could be deduced for Tirandamycin B.

13C NMR spectra of streptolydigin, tirandamycin, and related degradation products.

“…The identical chemical shift is observed for C-18 in tirandamycal (6). Of the remaining four methyl carbons in 3 and 4, C-14 should be at lowest field due to the double ji-deshielding effect3b) of the oxygen atoms in the 2,9-dioxabicyclo[3.3.1]nonane ring.…”

“…These assignments were repeated for streptal (5) and tirandamycal (6) in which all the carbons noted (where present) appeared within 0.3 ppm of the corresponding carbons of 3 and 4, except C-4 of 5 which was downfield of C-4 in streptolic acid but as the only quaternary olefin carbon was unmistakable.…”

“…In the present paper we report the 13C NMR assignments of streptolydigin (1) and tirandamycin (2), as well as those of streptolic acid (3) and tirandamycic acid (4), degradation products obtained via periodate oxidation of the respective sodium salts of 1 and 2, and of streptal (5) and tirandamycal (6), compounds obtained by ozonolysis of 1 and 2.…”

Medium optimization of Streptomyces sp. 17944 for tirandamycin B production and isolation and structural elucidation of tirandamycins H, I and J

“…Five TAM producers are known, including three Streptomyces species of terrestrial origin, Streptomyces tirandis , 8 Streptomyces flaveolus , 9 and S. sp. 17944, 6 and two of marine origin, Streptomyces sp.…”

“…First isolated in the 1970s from S. tirandis 8 and S. flaveolus , 9 1 and 2 were originally discovered as bacterial RNA polymerase inhibitors. 23 It was not until very recently, 1 and 2 were re-discovered from the marine S .…”