10004. Virginiamycin

Nomenclature

CAS number: 11006-76-1
Staphylomycin; virgimycin; SKF-7988; Eskalin (SKB); Stafac (SKB); Staphylomycine (SKB).

Description and references

One of the streptogramins, q.v., produced by a Streptomyces virginiae: P. De Somer, P. Van Dijck, Antibiot. Chemother. 5, 632 (1955). Two principal components S1 and M1. Separation of factors M and S: H. Vanderhaeghe et al., ibid. 7, 606 (1957); of the complex into six components: Gosselinckx, Parmentier, Chromatogr. Symp., 2nd 1962, 1817. Nomenclature and identification with other streptogramins: P. Crooy, R. De Neys, J. Antibiot. 25, 371 (1972). HPLC determn in animal feeds: F. Gossele et al., Analyst 116, 1373 (1991). Quantitative determn of components from fermentation broth: B. V. Tyaglov et al., J. Planar Chromatogr. Mod. TLC 8, 374 (1995). Mode of action: B. T. Porse, R. A. Garrett, J. Mol. Biol. 286, 375 (1999). Review: A. M. Biot, Drugs Pharm. Sci. 22, 695-720 (1984). Review of use in feed: W. Witte et al., Acta Vet. Scand. Suppl. 93, 37-45 (2000).

Chemical structure

Properties

Amorphous, reddish-yellow powder, mp 115-120°. Sol in methanol, ethanol, chloroform. Poorly sol in water. Practically insol in hexane and petroleum ether.

Derivative

Virginiamycin S1.

Nomenclature

CAS number: 23152-29-6
Staphylomycin S.
C43H49N7O10; mol wt 823.89.
C 62.69%, H 5.99%, N 11.90%, O 19.42%.

Description and references

Hexacyclicdepsipeptide antibiotic. Structure: H. Vanderhaeghe, G. Parmentier, J. Am. Chem. Soc. 82, 4414 (1960).

Properties

Crystals from methanol, mp 240-242°. [α]D20 28° (c = 1 in ethanol). uv max (ethanol): 305 nm (log ε 3.85).

Derivative

Virginiamycin M1.

Nomenclature

CAS number: 21411-53-0
Mikamycin A; ostreogrycin A; pristinamycin IIA; staphylomycin M1; streptogramin A; vernamycin A.
C28H35N3O7; mol wt 525.59.
C 63.99%, H 6.71%, N 7.99%, O 21.31%.

Description and references

Macrolactone antibiotic, see also Pristinamycin. Structure: G. R. Delpierre et al., Tetrahedron Lett. 1966, 369; eidem, J. Chem. Soc. C 1966, 1653; D. G. I. Kingston et al., ibid. 1669. Biosynthesis: idem et al., Rev. Latinoam. Quim. 20, 128 (1989). Molecular dynamics: E. Surcouf et al., Stud. Phys. Theor. Chem. 71, 719 (1990).

Properties

Colorless laths from ethyl acetate, mp 203-205°. [α]D20 218° ( c = 0.34 in ethanol). uv max (ethanol): 228 nm (log ε 4.51).

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial; growth promotant.

Keywords

Antibacterial (Antibiotics)