Cell-free extracts were prepared by subjecting cells of freshly harvested E. Coli mutant 83-24 (B. D. Davis, J. Biol. Chem., 191, 315 (1951)) to ultrasonic vibration. The incubation mixtures contained 0.1 ml. of extract (2 mg. of protein), 5 µ of MgCl2, 50 µ of P04= buffer pH 7.4, 0.25 µ of E-4-P + 0.3 µ of PEP, or 0.25 µ of SDP, + additions (10 µ of KF, or 0.5 µ of iodoacetate) in a final volume of 1 ml. (When iodoacetate was added, the solution, 0.95 ml., was preincubated at 37°for 15 minutes prior to the addition of substrate.) Following incubation at 37°for the indicated length of time aliquots were removed for the bioassay of DHS with Aerobacter aerogenes mutant A170-143S1 (B. D. Davis and U. Weiss, Arch. Exp. Path, and Pharm., 220, 1 (1953)).
18d-Glycyrrhetic acid (lb) was converted in good yield to the 3-oxo-4,4-bis(nor-18J-olean-4-ene) derivative 11a in 25% overall yield. Derivatives of lb substituted in the A, B, C, and E ring were also prepared. Several 11-deoxoglycyrrhetic acid derivatives exhibited anti-DCA activity. In particular, when administered subcutaneously, 3-oxo-18/3-olean-12-en-30-oic acid (2d) had about 75% the activity of spironolactone administered subcutaneously. Several compounds also exhibited weak antiviral and antiinflammatory properties.
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