53-06-5Relevant articles and documents
Grapefruit juice and its flavonoids inhibit 11β-hydroxysteroid dehydrogenase
Lee, Yil Seob,Lorenzo, Beverly J.,Koufis, Theo,Reidenberg, Marcus M.
, p. 62 - 71 (1996)
Introduction: The enzyme 11β-hydroxysteroid dehydrogenase (11β-OHSD) oxidizes cortisol to inactive cortisone. Its congenital absence or inhibition by licorice increases cortisol levels at the mineralocorticoid receptor, causing mineralocorticoid effects. We tested the hypothesis that flavonoids found in grapefruit juice inhibit this enzyme in vitro and that grapefruit juice itself inhibits it in vivo. Methods: Microsomes from guinea pig kidney cortex were incubated with cortisol and nicotinamide adenine diraucleotide (NAD) or nicotinamide adenine dinucleotide phosphate (NADP) and different flavonoids and the oxidation to cortisone measured with use of HPLC analysis. In addition, healthy human volunteers drank grapefruit juice, and the ratio of cortisone to cortisol in their urine was measured by HPLC and used as an index of endogenous enzyme activity. Results: Both forms of 11β-OHSD requiring either NAD or NADP were inhibited in a concentration-dependent manner by the flavonoids in grapefruit juice. Normal men who drank grapefruit juice had a fall in their urinary cortisone/cortisol ratio, suggesting in vivo inhibition of the enzyme. Conclusion: Dietary flavonoids can inhibit this enzyme and, at high doses, may cause an apparent mineralocorticoid effect.
Selective reduction of 4,6- conjugate diene -3-one steroid compound method
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Paragraph 0098-0105, (2019/11/21)
Belonging to the field of chemical pharmacy, the invention relates to a method for selective reduction of 4, 6-conjugated diene-3-one steroid, and solves the problem of low yield in hydrogen reduction. The method mainly includes the steps of: 1) adding the 4, 6-conjugated diene-3-one steroid, a liquid solvent, a catalyst, and a reducing agent hydrogen donor into a reaction kettle, performing nitrogen protection, and carrying out stirring heating till reflux; 2) carry out reflux reaction for 3-10h; 3) at the end of reaction, filtering out the catalyst; 4) distilling the solvent; 5) adding purified water after distillation; and 6) conducting cooling, pumping filtering, washing and drying to obtain a 4-ene-3-steroid crystal.
Nitrate esters of corticoid compounds and pharmaceutical applications thereof
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, (2008/06/13)
Compounds of the formula and use of the compounds as medicaments.
Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor
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, (2008/06/13)
Methods for reducing or preventing transplant rejection in the eye of an individual are described, comprising: a) performing an ocular transplant procedure; and b) implanting in the eye a bioerodible drug delivery system comprising an immunosuppressive agent and a bioerodible polymer.
Photochemical Studies, 64. - Photostability of Glucocorticoids in the Solid State
Reisch, Johannes,Iranshahi, Lotfollah,Ekiz-Guecer, Nurten
, p. 1199 - 1200 (2007/10/02)
Most of the pharmacopoeia require that the glucocorticoids hydrocortisone (1), cortisone (2), hydrocortisone 21-acetate (3) and cortisone 21-acetate (4) must be protected from light during storage.The present study shows that irradiation of these compounds in the solid state leads to the loss of the side chain at C-17.Two-17-ketosteroids, 11β-hydroxy-4-androstene-3,17-dione (6) and 4-androstene-3,11,17-trione (7), were obtained as photoproducts (yields 3percent and 4percent, respectively).Key Words: Hydrocortisone / Cortisone / Steroids / Photochemistry
Evidence for a new biologic pathway of androstenedione synthesis from 11-deoxycortisol
Auzeby, Andre,Bogdan, Andre,Touitou, Yvan
, p. 33 - 36 (2007/10/02)
17-Hydroxyprogesterone is a well-known precursor of androstenedione in adrenal biosynthesis.This study using sheep adrenal incubations demonstrates that 11-deoxycortisol, the precursor of cortisol synthesis, also can be a precursor of androstenedione.Indeed, our data shown that androstenedione synthesis is negatively correlated to the synthesis of cortisol and cortisone.This fact allowed us to infer that this new pathway is closely related to the activity of the 11β-hydroxylase that is responsible for the synthesis of cortisol.Indeed, when the activity of this enzyme is impaired, 11-deoxycortisol follows the pathway that leads to androstenedione synthesis in the adrenals.This pathway could explain, at least in part, the marked increase of androstenedione observed in congenital adrenal hyperplasia due to 11β-hydroxylase deficiency.
First Enantioselective Total Synthesis of (+)-Cortisone
Nemoto, Hideo,Matsuhashi, Norikazu,Imaizumi, Mari,Nagai, Mitsuo,Fukumoto, Keiichiro
, p. 5625 - 5631 (2007/10/02)
The intramolecular cycloaddition of an olefinic o-quinodimethane, having an optically active oxathiane system as a stereodirecting group, leads enantioselectively to A-nor B-aromatic steroids.This reaction is the key in an enantioselective total synthesis of (+)-cortisone (1).
Total Synthesis of ( +/-)-Cortisone. Double-Hydroxylation Reaction for Corticoid Synthesis
Horiguchi, Yoshiaki,Nakamura, Eiichi,Kuwajima, Isao
, p. 6257 - 6265 (2007/10/02)
Total syntheses of (+/-)-cortisone and (+/-)-adrenosterone have been achieved in 18 steps with the aid of metal-assisted new synthetic sequences in particular, ene reaction and homoenolate chemistry.A novel double-hydroxylation reaction of enol silyl ethers leading to a single step construction of the dihydroxyacetone side chain in corticoids has been developed and applied to the synthesis of cortisone, cortexolone, and 16α-methylcortexolone.
