Prumycin

Discovery (1,2), producing organism (2) and structure (3,4)

Prumycin was isolated from a culture broth of the actinomycete strain F-1028 and found to be an antifungal antibiotic. The total synthesis of prumycin has been reported by many groups. The first total synthesis of prumycin was reported by Kuzuhara et al (5).

Physical data (1)

Colorless needles in powder form. C₈H₁₇N₃O₄; mol wt 219.12. Sol. in H₂O. Slightly sol. in EtOH. Insol. in most organic solvents.

Biological activity (1, 6-10)

1) Antimicrobial spectrum of prumycin hydrochloride (1)

2) Antifungal activity
A. Preventive effect, 100% inhibition at 50 ppm; Curative effect, 76% inhibition at 50 ppm (Botrytis cinerea on kidney bean leaves)
B. Mode of action (6)
Prumycin inhibited a cell-free protein synthesis of growing cells of Botrytis cinerea.

3) Antitumor activity (7–10)
A. Administration of 50 mg/kg (i.p.) of prumycin on days 9, 12 and 15 resulted in regression of mouse mammary adenocarcinoma KSP-1 in C3H/He mice.
B. Mode of action: Both protein and DNA synthesis were inhibited by 30% at 10 µg/ml in HeLa S3 cells.

4) Toxicity (7)
LD₅₀: 155 mg/kg (mice i.p.), 144 mg/kg (mice i.v.), 70 mg/kg (rats i.p.)

5) No suppression of hemolytic plaque forming cells was observed against sheep red blood
cells at 75 mg/kg.

References

1. [45] T. Hata et al., J. Antibiot., 24, 900–901 (1971)
2. [66] S. Omura et al., Agricult. Biol. Chem., 37, 2805–2812 (1973)
3. [52] S. Omura et al., J. Chem. Soc., Chem. Commun., 1972, 633–634 (1972)
4. [83] S. Omura et al., J. Chem. Soc., Chem. Commun., 1974, 1627–1631(1974)
5. H. Kuzuhara et al., Tetrahedron Lett., 1853-1856 (1975)
6. [78] J. L. Schwartz et al., J. Antibiot., 27, 379–385 (1974)
7. [154] S. Okubo et al., J. Antibiot., 32, 347–354 (1979)
8. [177] S. Okubo et al., J. Antibiot., 33, 221–225 (1980)
9. [178] S. Okubo et al., J. Antibiot., 33, 226–230 (1980)
10. [179] S. Okubo et al., J. Antibiot., 33, 231–235 (1980)