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Isolation and Identification of Four New Carboxylie Acid Metabolites of Cortisol in Man

1973; Oxford University Press; Volume: 37; Issue: 5 Linguagem: Inglês

10.1210/jcem-37-5-811

1945-7197

H. Leon Bradlow, Barnett Zumoff, Carl Monder, Hee Jung Lee, LEON HELLMAN,

Steroid Chemistry and Biochemistry

The present study describes the isolation from human urine and definitive chemical identification of 4 members of a new class of acidic metabolites of corticol, characterized by a 21-oic acid group: 3α, 17, 20α-trihydroxy-11-oxopregnan-21-oic acid; 3α,17,20β-trihydroxy-11-oxopregnan-21-oic acid; 3α,11β,17,20α-tetrahydroxypregnan-21-oic acid; 3α,11β,17,20β-tetrahydroxypregnan-21-oic acid; The trivial name “cortoic acids” is suggested for this group of metabolites; the individual compounds, named after the corresponding 21-hydroxy metabolites, would be: “cortolonic acid,” “β-cortolonic acid,” “cortolic acid” and “β-cortolic acid,” respectively. Together these metabolites constitute 5–25% (mean 12%) of the administered cortisol. The most abundant by far is “cortolonic acid” which is one of the 4 most abundant metabolites of cortisol. Transformation of cortisol to these metabolites involves an intramolecular shift of a hydrogen atom from C-21 to C-20 as well as oxidative removal of the other hydrogen atom from C-21. The order in which these 2 processes take place has not been established.