Streptomyces virginiae

A41030 complex Streptomyces virginiae NRRL 15156 1982 Lilly 41-43... 

The biosynthesis of virginiamycin Ml in Streptomyces virginiae has been studied using both radiolabeled precursors (63) and stable isotope techniques (45, 63-65). Incorporation of [2-l4C]acetate, L-[methyl-3H]methionine, dl-3-14C]serine, L-[3,4-3H2]proline, and [2-14C]glycine established these compounds as the main precursors (63). The assumption that carbons 2, 26, 27, and 28 arose from valine was supported by the observation that no incorporation of appropriately labeled mevalonolactone was observed (65). On the basis of the radio-... 

Lee CK, Minami M, Sakuda S, Nihira T, Yamada Y. Stere- 72. ospecilic reduction of virginiamycin Ml as the virginiamycin resistance pathway in Streptomyces virginiae. Antimicrob. Agents Chemother. 1996 40(3) 595-601. 

Pulsawat N, Kitani S, Nihira T. Characterization of biosynthetic gene cluster for the production of virginiamycin M, a streptogramin type A antibiotic, in Streptomyces virginiae. Gene 2007 393 31-42. 

Serine is the precursor of several antibiotics. The oxazole ring of the antibiotic virginiamycin Mj 100(Scheme 31)is derived from serine incubation of Streptomyces virginiae with samples of (2S, 3R)- and (2S, 3S)-[3- Hi]serine, derived as in Scheme 18, showed that the 3-pro-S hydrogen of serine is lost on formation of the double bond (107). This implies anti dehydrogenation, a process more commonly found to be syn. The -lactam antibiotic nocardicin 101 is biosynthesized from serine, and incubation of Nocardia uniformis with stereospecifically deuterated serines, prepared by the method outlined in Scheme 21, has yielded samples of norcardicin, the NMR spectra of which indicated that ) -lactam ring formation occurs with inversion of configuration (108, 109). 

The related nogarols, such as 301-A (43b), 301-B (43c) and decilorubicin (43d) [85,86], have been isolated from Streptomyces virginiae, var. nanpin-genesis 301. They are 1,6,11-trihydroxyanthracycline derivatives. 

Kiyo K, Sho S, Marunaka T, Miyake Y, Minami Y (1987) Antibiotic compounds 301 manufacture with Streptomyces virginiae. Jpn Kokai Tokkyo Koho JP Patent 62030793 (Chem Abstr 107 5739)... 

An antibiotic complex from Streptomyces virginiae cultures, e.g., V. M C28H35N3O7, Mr 525.60, mp. 165-167 °C (decomp.), [ajp-190° (CjHjOH), soluble in DMF. V. is used as a fodder additive in veterinary medicine. 

The biosynthesis of pristinamycin 11 by Streptomyces pristinaespiralis is currently being studied in the RHONE-POULENC laboratories. Previous studies [90, 91] on the biosynthesis of virginiamycin Mi( = pristinamycin Ilyv, see Table 7) by Streptomyces virginiae identified acetic acid, valine, glycine, proline and serine as the natural building blocks of virginiamycin Mj (see Fig. 10). The 32-methyl was shown to be derived from methionine and the 33-methyl from the methyl of a molecule of acetic acid. 

Formation of the dehydroproline residue in virginiamycin Mi( = pristinamycin IIa) involving a proline hydroxylase in Streptomyces virginiae was postulated by Kingston and co-workers [93]. 

Nihira T, Shimizu Y, Kim HS, Yamada Y. Structure-activity relationships of virginiae butano-lide C, an inducer of vlrginiamycin production in Streptomyces virginiae. J. Antibiot 1988 41 1828-1837. 

Kim HS, Tada H, Nihira T, Yamada Y. Purification and chatacterization of virginiae butaiHi-lide C-binding protein, a possible pleiotropic signal-transducer in Streptomyces virginiae. J Antibiot 1990 43 692-706. 

Okatnoto S, Nihiia T, Kataoka H, Suzuki A, Yamada Y. Purification and molecular cloning of a butyrolactone autoregulator receptor from Streptomyces virginiae. J Biol Chem 1992 267 1093-1098. 

C12H23NO10 341.314 From Streptomyces virginiae var. 4243 MT/Tl. Active against limited strains of gram-positive and -negative bacteria. Sol. H2O fairly sol. MeOH poorly sol. butanol, hexane. pK 6.98. 

He F, Yang Y, Yang G, Yu L. Studies on antibacterial activity and antibacterial mechanism of a novel polysaccharide from streptomyces Virginia H03. Food Control. 2010 21 1257-62. 

Fig. 88.11 New metabolic products from diosgenin by Streptomyces virginiae IBL-14...

Wang F-Q, Zhang C-G, Li B, Wei D-Z, Tong W-Y (2009) New microbiological transformations of steroids by Streptomyces virginiae IBL-14. Environ Sci Technol 43 5967-5974... 

Virginiamycin Streptomyces virginiae + Peptide Animal growth promotant... 

Rauuolfia vertiaillata Myrotheaium verruoaria Catharanthus roseus Vinca major Catharanthus roseus Streptomyces virginiae... 

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