Epiandrosteron

Kullak-Ublick, G. A., et al. Dehydro-epiandrosterone sulfate (DHEAS) identification of a carrier protein in human liver and brain. FEBS Lett. 1998, 424, 173-176. 

Chloro-17-nitroso-3/i-hydroxy-5a-androstane 213, generated from the oxime 212 of epiandrosterone and t-butyl hypochlorite, reacts with cyclohexadiene in chloroform/metha-nol at — 20 °C to yield, after two weeks, epiandrosterone and the bridged dihydrooxazine 214 in an enantiomeric excess of better than 95%108. 

The biologically inactive estrone sulfate (EIS) and dehydro-epiandrosterone-sulfate (DHEAS) are the most abundant circulating estrogenic precursors in the plasma of post-menopausal women [103]. Desulfation of inactive steroid-3-0-sulfates by estrone-sulfatase (STS) plays a key role in the regulation of levels of receptor-active estrogenic steroids (estradiol and androstenediol) in breast cancer cells (Fig. 9). There is strong evidence suggesting that estrone sulfatase (STS) and DHEA-sulfatase are the same enzyme [103]. 

Alkenes reacted with RuCyaq. CH3CO3H/CH3CN-CH2CI2 giving a-ketols thus cix-5-(methoxycarbonyl)-2-cyclohexenyl acetate (1) gave (2R, 35, 5R )-3-acetoxy-2-hydroxy-5-(methoxycarbonyl)-l-cyclohexanone (2) (Fig. 3.9, Table 3.2). Cortisone acetate was isolated in this way from epiandrosterone after a number of steps [179]. 

Serum sex hormones effect. DION (300 mg androstenedione, 150 mg dehydro-epiandrosterone, 540 mg saw palmetto, 300 mg indole-3-carbinol, 625 mg chrysin, 750 mg Tribulus terrestris), administered daily to healthy 30- to 59-year-old men for 28 days, produced no change in serum concentrations of total T and PSA. DION increased the concentrations of serum androstenedione (342%), free T (38%), DHT (71%), and estradiol (103%). Serum high-density lipoprotein (HDL) cholesterol concentrations were reduced by 5 mg/dL in DION (p < 0.05). Increases in serum free T (r = 0.01), androstenedione (r = 0.01), DHT (r = 0.03), or estradiol (r = 0.07) concentrations in DION were not related to age. The ingestion of androstenedione combined with herbal products increased serum-free T concentrations in older men, but herbal products did not prevent the conversion of... 

On the way to prepare metabolites of equine norethandrolone, a Reformatsky reaction has been applied to epiandrosterone acetate 44 in refluxing benzene the authors succeeded... 

Diketone formed epiandrosterone was obtained in 17% yield. p Secondary alcohol is oxidized to the ketone. 

Fig.4.13. Separation of DNPH-steroids on a 1-m column of 1.3% BOP on Zipax eluted with isooctane (0.5 ml/min) at ambient temperature. Peaks 1 = epietiocholanolone 2 = androsterone 3 = epiandrosterone 4 = etiocholanolone S = dehydroepiandrosterone. (From ref. 32 with permission of the American Chemical Society, Washington.)...

The solution was dried over sodium sulfate and exaporated. 13.6 g of crude dehydro-epiandrosterone-3-oenanthate were obtained, melting point 70°-72°C (recrystallisation from methanol). 

The synthesis of derivatives of steroids dihydrotestosterone 160 and epiandrosterone 161, containing indole and phosphoryl fragments, is described in the patent [156],... 

Abadie JM, Wright B, Correa G et at. (1993) Effect of dihydro-epiandrosterone on neurotransmit-ter levels and appetite regulation of the obese Zucker rat. Diabetes 42 662-669... 

Lead(IV) azide yields 1,4-diazides from 1,3-dienes. Whilst cycloadditions are beyond the scope of this review, the sequence of Scheme 93 is potentially important 1,3-dienes undergo asymmetric Diels-Alder reactions with an a-chloronitroso derivative of epiandrosterone with high ee, and Ae N—O... 

SYNS (3-p,5-a)-3-(ACETYLOXY)ANDROSTAN-17-ONE ANDROSTAN-17-ONE, 3-(ACETYLOXY)-, (3-P,5-a)- DEHYDROEPIANDROSTERONE ACETATE EPIANDROSTERONE, DEHYDRO-, ACETATE ANDROSTEN-17-ONE, 3-p-HYDROXY-, ACETATE... 

Johnson and co-workers found potassium f-butoxide the best base for the Dieckmann cyclization of the diester (3) to epiandrosterone (4). In this case both sodium methoxide and sodium hydride were ineffective. 

The prefix alio- is a term used to describe tlie stereoisomerism of the hydrogen atom at C-5. When the configuration differs at any other carbon atom, the prefix epi- is used (e.g., androsterone possesses a 3a-hydroxyl group, and epiandrosterone a 3P-hydroxyl group testosterone possesses a 17P-hydroxyl group, and epitestosterone a 17a-hydroxyl group).. 

Orentreich N, Brind JL, Rizer RL, Vogelman JH. Age changes and sex differences in serum dehydro epiandrosterone sulfate levels throughout adulthood. J Clin Endocrinol Metab 1984 59 551-5. 

The bulk of the urinary 17-KSs consists of andro-sterone, epiandrosterone, etiocholanolone, DHEA, 11-keto-and lip-hydroxyandrosterone, and 11-keto- and 11(3-hydroxyetiocholanolone. DHEA and 11-oxygenated 17-KSs are produced only by the adrenal glands, whereas the others also arise from precursors (androstenedione and testosterone) elaborated by the gonads. Thus the main purpose of measuring these steroid metabolites is to assess adrenal androgen production. 

Figure 54-1 Schematic representation of steroid and protein hormone production by the placenta. DHEA-S, Dehydro-epiandrosterone sulfate CG, chorionic gonadotropin PL, placental lactogen ACTH, adrenocorticotropic hormone TRH, thyroid-stimulating hormone CT, chorionic thyrotropin GnRH, gonadotropin-releasing hormone CRH, corticotropin-releasing hormone PAPP-A, pregnancy associated plasma protein-A.

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