7 alpha-Hydroxylation of 5 alpha-androstane-3 beta, 17 beta-diol in normal and hyperplastic human prostate]

Incubation of 4-14C-5 alpha-androstane-3 beta, 17 beta-diol with human normal and hyperplastic prostate minces led to the NADPH-dependent production of a major polar radiometabolite which was identified as 5 alpha-androstane-3 beta, 7 alpha, 17 beta-triol and proved the presence of a 3 beta-hydroxysteroid-7 alpha-hydroxylase in prostate. Such evidences may bring new leads for the study of the mechanisms of androgenic steroid action in the prostate gland.     

Evidence of 5 alpha-androstane-3 beta, 6 alpha, 17 beta-triol and of 5 alpha-androstane-3 beta, 7 alpha, 17 beta-triol in the anterior pituitary of the prepuberal male rate]

Incubation of 3H-5 alpha-androstane-3 beta, 17 beta-diol with anterior pituitaries from immature male Rats led to the major production of polar radio-metabolites. Of these, 53 and 27% were identified with 5 alpha-androstane-3 beta, 6 alpha, 17 beta-triol and 5 alpha-androstane-3 beta, 7 alpha, 17 beta-triol, respectively. The formation of these trihydroxysteroids may be involved in the intracellular regulation of 5 alpha-androstane-3 beta, 17 beta-diol levels.     

Synthese von 5α- und 5β-Androstan-17β-ol-3-on-17-acetat aus Hyodesoxycholsäure

Summary 5- and 5-androstane-17-ol-3-one-17-acetate have been prepared from 5-androstane-6, 17-diol-3-one-17-acetate by a synthesis involving directedHuang-Minlon-reduction.Separation of 5-androstane-17-ol-3-one from its 5-isomer could readily be achieved by crystallisation of their 3-ethylenketals from acetone.     

17β-Hydroxymethyl-Steroide: Darstellung von Derivaten des 17β-Hydroxymethyl-4-androsten-3-ons

Summary Starting from methyl 3-oxo-4-etienate, the authors prepared 17-hydroxymethyl-4-androsten-3-one and 11-hydroxy-17-hydroxymethyl-4-androsten-3-one. Chlorination of 17-acetoxymethyl-4-androsten-3-one yielded 4-chloro-17-acetoxymethyl-4-androsten-3-one. 17-Hydroxymethyl-1, 4-androstadien-3-one was obtained from 17-hydroxymethyl-4-androsten-3-one, both by chemical and biological methods.     

Adrenal corticosteroidogenesis after removal of ventral prostate gland

Summary Removal of the ventral prostate gland in adult male rats causes an increase in adrenal weight, and stimulation of adrenal ⁵-3-hydroxysteroid dehydrogenase activity along with elevation of serum levels of corticosterone and prolactin.     

The formation of androgens in human foetal liver in vitro

Zusammenfassung Nach Inkubation des homogenisierten Lebergewebes menschlicher, 7–20 Wochen alter, Foeten mit 3-Hydroxy-5-androsten-17-on wird die Bildung von Testosteron, 4-Androsten-3, 17-dion und 5-Androsten-3, 17-diol nachgewiesen.     

The distribution of some enzymes involved in the steroidogenesis of hen's ovary

Riassunto È stata studiata con metodi istochimici la distribuzione della ⁵-3-idrossisteroide deidrogenasi ( ⁵-3-HSDH) e delle 17-idrossisteroide deidrogenasi (17-HSDH), DPN- e TPN-dipendenti, nell'ovario di gallina ovulante. Mentre la ⁵-3-HSDH è presente in tutti i tessuti a secrezione steroide dell'ovario, la 17-HSDH è localizzata solo nelle cellule della granulosa.     

7a-Aza-B-homo[7a, 7-d]tetrazole analogues of progesterone and testosterone

Summary The tetrazole analogues of progesterone and testosterone, namely, 7a-aza-B-homo-4-pregneno[7a, 7-d]tetrazole-3,20-dione (5) and 3-oxo-7a-aza-B-homo-4-androsteno[7a, 7-d]tetrazol-17-yl acetate (8), have been prepared which are worthy of biological testing.Part XLIII in the series Steroids and Related Studies. For Part XLII see H. Singh and K.K. Bhutani, Indian J. Chem. in press.     

Darstellung von Derivaten des 6-Chlor-17β-acetoxy-Δ 5-androsten-7-on

Summary 6-Chloro-17-acetoxy-5-androsten-7-one and some of its derivatives have been prepared from ⁵-steroids by a synthesis involving elimination of the substituent from position 3, introduction of a 7-keto group by allyloxidation and chlorination of the resulting compound with sulphuryl chloride.     

Isolement dans le plasma veineux périphérique et surrénalien de l'ester-sulfate de 5-androstène 3β-ol 7,17-dione

Summary The isolation of the ester-sulfate of 5-androstene 3-ol 7, 17-dione is described. This sulfate has been found in the peripheral venous blood plasma of several virilized women. Moreover, it has been isolated in 3 adrenal tumors and in the adrenal venous plasma of one of them.     

Defensive steroids from a carrion beetle (Silpha americana)

The defensive anal effluent discharged by Silpha americana in response to disturbance contains a mixture of steroids stemming from a glandular annex of the rectum. The compounds have been characterized as 15 beta-hydroxyprogesterone (1, principal component), 5 beta-pregnan-15 beta-ol-3,20-dione (2), 5 beta-pregnan-3 alpha, 15 beta-diol-20-one (3), 5 beta-pregnan-7 beta, 15 beta-diol-3,20-dione (4), 5 beta-pregnan-3 alpha, 7 beta, 15 beta-triol-20-one (5), 5 beta-pregnan-16 alpha-ol-3,20-dione (6), and 5 beta-pregnan-3 alpha, 16 alpha-diol-20-one (7), none previously found in insects. Bioassays with jumping spiders showed compounds 1 and 6 to be feeding deterrents at the 1 microgram level.     

Demonstration of a receptor for 5 alpha-androstane-3 beta, 17 beta-diol in the cytosol of the anterior pituitary of prepubertal male rats]

The presence of a specific receptor for 5alpha-androstan-3beta, 17beta-diol (3beta-diol) in the pituitary cytosol from prepubertal male rats was demonstrated. Its characteristics were: Ka = 5.2.10(7) M-1 KD = 1.9 X 10(-8) M, number of specific binding = 8.7 10(-14) moles per mg of proteins. Its sedimentation constant was 3 S. Competition assays showed that only 3beta-diol itself and estrogens were able to compete for the binding sites for 3beta-diol. Androgens, including 3alpha-diol, were inefficient. This receptor was found only in pituitary cytosol, it was missing from hypothalamic or cortical cytosols. This special localization seemed to foreshadow a specific role for 3beta-diol in the anterior hypophysis.     

16-β-methylprednisone from hecogenin

Zusammenfassung Es wird über die Herstellung des 16-Methylprednisons berichtet, welche vom Hecogenin ausgehend über ca. 15 Stufen durchgeführt wird. Als wichtige Zwischenstufe treten 5-Pregn-16-en-3-ol-11, 20-dion-Acetat und 16-Methylen-5-pregnan-3, 17-diol-11, 20-dion auf: letzteres wird durch eine stereospezifische katalytische Reduktion in das entsprechende 16-Methyl-derivat umgewandelt.     

11β-methyl-19-norsteroids: Novel progestational hormones

Zusammenfassung Die Synthese von 3, 17-Diacetoxy-17-Äthinyl-11-Methylestr-4-en (XII) wird beschrieben. Die Substanz besitzt besonders starke Antifertilitätseigenschaften, wie sie sonst nur Mischungen von Hormonen eigen sind, welche für die Humanfertilität benutzt werden, jedoch ohne deren Nebenwirkungen.     

Plasma lipid-bound sialic acid alterations in neoplastic diseases

Plasma lipid-bound sialic acid (LSA) was assayed in normal volunteers, patients with non-malignant diseases, and a variety of cancer patients. Mean plasma LSA in 50 normal volunteers, 16 patients with non-malignant diseases, 54 breast cancer, 17 lung cancer, 15 colon cancer, 7 ovarian cancer, 5 prostate cancer, 4 leukemia, 4 gastrointestinal, 3 thyroid cancer, 3 pancreas cancer and 2 adrenal cancer patients were 17.7, 23.2, 58, 85, 56.7, 46.2, 56.7, 53.3, 31.1, 33.2 and 119.5 mg/dl, respectively. None of the normal volunteers had elevated plasma LSA values. Plasma LSA level was not significantly different in male and female volunteers. Two out of 114 different cancer patients had plasma LSA levels within normal range exhibiting 98.2% sensitivity of the assay. Plasma LSA, which is relatively simple to assay, may be used as a tumor marker in wide variety of neoplastic diseases.     

Isolement et identification du 5β-prégnane 11β, 17α, 21-triol 3, 20-dione (Dihydrocortisol) dans l'urine humaine

Summary 5-pregnane 11, 17, 21-triol 3, 20-dione (dihydrocortisol) has been isolated and identified in the urine of patients with feminizing adrenal cortical cancer. This steroid showed the same Rf as synthetic dihydrocortisol in six different chromatographic systems. After acetylation, its Rf was the same as that of 21 monoacetate of dihydrocortisol. After bismuthic or chromic oxydation, it had the same chromatographic Rf as 5-androstane 11-ol 3, 17-dione and 5-androstane 3, 11, 17-trione respectively. After chromic oxydation of its acetate, the Rf was the same as that of 21 monoacetate of cortisone.     

Plasma lipid-bound sialic acid alterations in neoplastic diseases

Summary Plasma lipid-bound sialic acid (LSA) was assayed in normal volunteers, patients with non-malignant diseases, and a variety of cancer patients. Mean plasma LSA in 50 normal volunteers, 16 patients with non-malignant diseases, 54 breast cancer, 17 lung cancer, 15 colon cancer, 7 ovarian cancer, 5 prostate cancer, 4 leukemia, 4 gastrointestinal, 3 thyroid cancer, 3 pancreas cancer and 2 adrenal cancer patients were 17.7, 23.2, 58, 85, 56.7, 46.2, 56.7, 53.3, 31.1, 33.2 and 119.5 mg/dl, respectively. None of the normal volunteers had elevated plasma LSA values. Plasma LSA level was not significantly different in male and female volunteers. Two patients with rheumatic arthritis had LSA values slightly elevated over the mean + 2 SD for the normal volunteers. Two out of 114 different cancer patients had plasma LSA levels within normal range exhibiting 98.2% sensitivity of the assay. Plasma LSA, which is relatively simple to assay, may be used as a tumor marker in wide variety of neoplastic diseases.     

Allene versus acetylene in progestational steroids

In an attempt to find a side chain biologically superior to the common acetylene (e.g., 17alpha-ethynyl as in ethisterone, mestranol and ethinyl estradiol) for an orally active protestogen, 17alpha allene derivatives of norethindrone and mestranol were prepared and tested in the rabbit CLAUBERG assay, and in the rat vaginal smear assay. The minimal effective dose for norethindrone in the rabbit test was .05 mg sc for 5 days; .0025 mg for 17alpha-norethindrone-CH=C=CH2; and .005 mg for 17 alpha-norethindrone-C(CH3)=C=CH2. Similar increases in progestational activity were obtained in the antiestrogenicity and ovulation inhibiton tests. When a saturated carbon was inserted, as in 17alpha-norethindrone-CH(CH3)-CH=C=CH2, the beta allenyl derivative was completely inactive. The ED50 for mestranol in the rat vaginal smear assay (estrogenicity) was .003mg; for 17alpha-mestranol-CH=C-CH2 .01 mg; for 17alpha-mestranol-C(CH3)=C=CH2 .015 mg.     

Estrogen and accessory sex gland lipids

Summary Administration of estradiol-17 elicited differential responses on accessory sex glands of rats. In caput epididymis, the estrogen treatment led to an accumulation of glycerides and phospholipids while in cauda epididymis, there was no significant change. However, in seminal vesicles, depletion of phospholipids was observed In prostate, the treatment, resulted in an accumulation of glycerides.Part of Ph.D. Thesis. Umapathy, E., Thesis. University of Madras, India, 1977.     

17β-Hydroxymethyl-steroide: Darstellung von 17α-Hydroxy-17β-hydroxymethyl-4-androsten-3-on aus Reichsteins Substanz S

Summary The synthesis of 17-hydroxy-17-hydroxymethyl-4-androsten-3-one fromReichsteins compound S is described. Transformation of 3,3-ethylenedioxy-17-hydroxy-17-hydroxymethyl-5-androsten into 17-methyl-isotestosterone demonstrates the configuration of the substituents at C-17.