9947. Venturicidins

Description and references

Antifungal antibiotics isolated from Streptomyces aureofaciens strains. Preliminary isolation work: Rhodes et al., Nature 192, 952 (1962). Isoln of venturicidins A and B and activity studies: Brufani et al., Helv. Chim. Acta 51, 1293 (1968); see also Langcake et al., Biochem. Soc. Trans. 2, 202 (1974). Final structures: Brufani et al., Experientia 27, 604 (1971); eidem, Helv. Chim. Acta 55, 2329 (1972).

Chemical structure

Derivative

Venturicidin A.

Nomenclature

CAS number: 33538-71-5
Venturicidin B 3′-carbamate.
C41H67NO11; mol wt 749.97.
C 65.66%, H 9.00%, N 1.87%, O 23.47%.

Properties

Needles from chloroform-petr ether, mp 145-147°. Also reported as mp 140-142°. [α]D +119° (c = 0.5 in chloroform). uv max (alcohol): 206, 247 (shoulder), ≈300 nm (shoulder) (log ε 3.80, 2.23, 2.08).

Derivative

Venturicidin B.

Nomenclature

CAS number: 33538-72-6
(3-Decarbamoyloxy)-3-hydroxyventuricidin A.
C40H66O10; mol wt 706.95.
C 67.96%, H 9.41%, O 22.63%.

Properties

Amorphous white powder from chloroform-ether, mp 168-170°. Also reported as mp 145-149° (ethyl acetate-petr ether). [α]D +100° (c = 0.847 in chloroform).