Vineomycin

Discovery, producing organism and structure (1-3)

While screening for new antibiotics in actinomycetes, vineomycins A₁, A₂, B₁ and B₂ were isolated from a culture broth of the actinomycete strain OS-4742T. These compounds are active against Gram-positive bacteria and the Sarcoma 180 solid tumor in mice. Vineomycin A1 (P-1894B) also possesses potent inhibitory activity against collagen prolyl hydroxylase. The total synthesis of vineomycin B2 has been reported by several groups. The first total synthesis was reported by Danishefsky et al (4).

Physical data (Vineomycin B2) (1–3)

Yellow powder. C₄₉H₅₈O₁₈; mol wt 934.36. Sol. in MeOH.

Biological activity (2,4,5)

1) Antimicrobial activity

2) Anti-tumor activity
When vineomycin A1 (50 mg/kg) was administered i.p. once a day after transplantation of sarcoma 180 cells, the tumor size (T/C) on the 7th day was 0.13.

Biosynthesis (5)

The labeling experiments with both [1-¹³C]- and [1,2-¹³C2] sodium acetate followed by ¹³CNMR spectroscopy revealed that the benz[a]anthraquinone chromophore of A₁ originated from a decaketide metabolite by decarboxylation of the carboxyl end and that of B₂ was formed via C-C bond cleavage of A₁.

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Vineomycin A₁ is commercially available as a biochemical reagent.

References

1. [138] S. Ōmura et al., J. Antibiot., 30, 908–916 (1977)
2. [210] N. Imamura et al., Chem. Pharm. Bull., 29, 1788–1790 (1981)
3. [220] N. Imamura et al., J. Antibiot., 34, 1517–1518 (1981)
4. S. Danishefsky et al., J. Am. Chem. Soc., 107, 1285–1293 (1985)
5. [239] N. Imamura et al., J. Antibiot., 35, 602–608 (1982)