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Rashadul Hossain, Rajia Sultana, Aychout Adhikari, Muhammad Iqbal Choudhary, Yusuff Ali, Shahed Zaman
A new ursane triterpene, torment (2 alpha,3 beta,19 alpha-trihydroxyurs-12-en) (1), was isolated from the fruits of Terminalia arjuna along with four known ursane and oleane triterpenes. The structures were established on the basis of extensive NMR (1D & 2D) and MS (EI & ESI) studies. Tormentic acid (2), 19 alpha-hydroxy asiatic acid (3) and olean-12-en-2 alpha,3 beta-diol (4) were isolated for the first time from this species. Compounds 1 and 2 lacked significant enzyme inhibition, cytotoxicity, immunomodulatory and antiglycation activities...
March 2014: Natural Product Communications
Patrícia Picciarelli-Lima, André G Oliveira, Adelina M Reis, Evanguedes Kalapothakis, Germán A B Mahecha, Rex A Hess, Cleida A Oliveira
BACKGROUND: Fluid homeostasis is critical for normal function of the male reproductive tract and aquaporins (AQP) play an important role in maintenance of this water and ion balance. Several AQPs have been identified in the male, but their regulation is not fully comprehended. Hormonal regulation of AQPs appears to be dependent on the steroid in the reproductive tract region. AQP9 displays unique hormonal regulation in the efferent ductules and epididymis, as it is regulated by both estrogen and dihydrotestosterone (DHT) in the efferent ductules, but only by DHT in the initial segment epididymis...
October 6, 2006: Reproductive Biology and Endocrinology: RB&E
Y Jiang, N Wang, X Yao, K Susumu
Six compounds were isolated from the anticoagulation and anticancer fractions of the bulbs of Allium chinense G. Don. On the basis of chemical evidence and spectral analysis (IR, EI-MS, 1HNMR, 13CNMR, 1H-1H COSY, HMBC, HMQC and NOESY), their structures were established as (25R, S)-5 alpha-spirostane-3 beta-ol 3-O-(beta-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->3)]-beta-D- glucopyranosyl-(1-->4)-beta-D-galactopyranoside) (1), (25R, S)-5 alpha-spirostane-3 beta-ol 3-O-(beta-D-glucopyranosyl (1-->2)-[beta-D-glucopyranosyl-(1-->3)](6-acetyl-beta-D-glucopyranosyl)- (1-->4)-beta-D-galactopyranoside) (2), (25R, S)-5 alpha-spirostane-2 alpha, 3 beta-diol 3-O-(beta-D-glucopyranosyl-(1-->2)-O-beta-D-glucopyranosyl-(1-->4)-beta-D- galactopyranoside) (3), (25S)-24-O-beta-D-glucopyranosyl-3 beta, 24 beta-dihydroxy-5 alpha-spirost-3-O-alpha-arabinopyranosyl-(1-->6)-beta-D-glucopyranoside (4), chinenoside II (5) and 2,3,4,9-tetrahydro-1-methyl-1H-pyrido [3,4-b] indole-3-carboxylic acid (6)...
May 1998: Yao Xue Xue Bao, Acta Pharmaceutica Sinica
L B Litvinova, V M Vakula
The female rats at a prepubertal period were introduced to the restored 5 alpha-androgens, namely: 5 alpha-dihydrotestosterone (DHT), 5 alpha-androstane-3 alpha, 17 beta-diol (3 alpha-diol) or 5 alpha-androstane-3 beta, 17 beta-diol (3 beta-diol) in the dose of 5 mg/100 g. Both DHT and 3 alpha-diol have been determined to induce the vaginal opening as the initial stage of puberty. Stimulation of the puberty in those rats was followed with an activation of both endocrine and generative functions of the ovaries...
2002: Fiziolohichnyĭ Zhurnal
N E Kushlinskiĭ, V G Degtiar', T V Babkina, Iu N Solov'ev, M D Aliev, N N Trapeznikov
The paper provides data of comparative assessment of activity of the key enzymes in metabolism of androgens in various morphological variants of sarcomas and benign bone tumors in 46 patients within the age range from 15 to 61, which were under treatment in the ORC named after N. N. Blokhin, RAMS, from 1996 to 1997. On the basis on publications and our own research results we can suggest that malignant human bone tumors of various histogenesis are subject to metabolic processes of testosterone (T), the principal androgen regulator in the bone tissue, as well as formation in bones of 5 alpha-dihydrotestosterone (DHT)...
July 1999: Uspekhi Fiziologicheskikh Nauk
V G Degtiar', N E Kushlinskiĭ
Based on analysis of the published experimental data, we propose a hypothetical mechanism of action of two androgens, 5 alpha-androstane-3 alpha,17 beta-diol (3 alpha-diol) and 5 alpha-androstane-3 beta,17 beta-diol (3 beta-diol), which are produced when 5 alpha-dihydrotestosterone (DHT) is reduced in sex steroids target cells. The mode of action of these diols as regulatory factors assumes that the androgens possess autocrine, paracrine, and endocrine action that differs from the action of DHT in animals and man and do not merely represent catabolites or metabolites capable of controlling the level of true androgenic hormone DHT...
November 1998: Izvestiia Akademii Nauk. Seriia Biologicheskaia
W Yan, K Ohtani, R Kasai, K Yamasaki
Further studies on the constituents of the fruits of Tribulus terrestris led to the isolation of five new steroidal saponins (terrestrosin A-E), (25R,S)-5 alpha-spirostan-3 beta-ol-3 -O-beta-D-galactopyranosyl(1-2)-beta-D- glucopyranosyl(1-4)-beta-D-galactopyranoside, (25R,S)-5 alpha-spirostan-3 beta-ol-3-O-beta-D-glucopyranosyl(1-4)-[alpha-L- rhamnopyranosyl(1-2)]-beta-D-galactopyranoside, (25R,S)-5 alpha-spirostan-12-on-3 beta-ol-3-O-beta-D-galactopyranosyl (1-2)-beta-D-glucopyranosyl(1-4)-beta-D-galactopyranoside, hecogenin 3-O-beta-D-galactopyranosyl)1-2)-[beta-D- xylopyranosyl(1-3)]-beta-D-glucopyranosyl(1-4)-beta-D-galactopyranoside and (25R,S)-5 alpha-spirostane-2 alpha, 3 beta-diol-3- O-beta-D-galactopyranosyl(1-2)-beta-D-glucopyranosyl(1-4)-beta-D- galactopyranoside, together with five known steroidal saponins, desgalactotigonin, F-gitonin, desglucolanatigonin, gitonin and tigogenin 3-O-beta-D- xylopyranosyl)1-2)-[beta-D-xylopyranosyl)1-3)]-beta-D-glucopyranosyl)1-4 )- [alpha-L-rhamnopyranosyl(1-2)]-beta-D-galactopyranoside...
July 1996: Phytochemistry
F Labrie, A Bélanger, L Cusan, J L Gomez, B Candas
The present data show a dramatic decline in the circulating levels of dehydroepiandrosterone (DHEA), DHEA-sulfate (DHEA-S), androst-5-ene-3 beta,17 beta-diol (5-diol), 5-diol-sulfate, 5-diol-fatty acid esters, and androstenedione in both men and women between the ages of 20-80 yr. In the 50- to 60-yr-old group, serum DHEA decreased by 74% and 70% from its peak values in 20- to 30-yr-old men and women, respectively. the serum concentrations of the conjugated metabolites of dihydrotestosterone (DHT), namely androsterone (ADT)-G, androstane-3 alpha,17 beta-diol (3 alpha-diol-G), androstane-3 beta,17 beta-diol (3 beta-diol-G), and ADT-sulfate are the most reliable parameters of the total androgen pool in both men and women, whereas serum testosterone and DHT can be used as markers of testicular secretion in men and interstitial ovarian secretion in women...
August 1997: Journal of Clinical Endocrinology and Metabolism
S A Shvets, P K Kintia, M A Naibi
A new plant source containing steroidal glycosides of the furostane and spirostane series has been shown. Ten individual steroidal glycosides (petuniosides) of the spirostane and furostane series have been isolated from Petunia hybrida L. seeds. They differ in the structures of aglycone and oligosaccharide chain, four of them are novel compounds, and their chemical structures have been established. Petuniosides A, C, and E are 3-O-beta-D-galactopyranoside spirostane; 3-O-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside spirostane; and 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside of (25R)-5 alpha-spirostan-3 beta-ol, respectively...
1996: Advances in Experimental Medicine and Biology
Y Mimaki, Y Takaashi, M Kuroda, Y Sashida, T Nikaido
Seven steroidal saponins were isolated from the stems of Nolina recurvata, five of which appeared to be new compounds and were assigned as spirosta-5,25(27)-diene-1 beta,3 beta-diol (neoruscogenin) 1-O--O-alpha-L-rhamnopyranosyl-(1--> 2)-O-[beta-D-xylopyranosyl-(1-->3)]-alpha-L-arabinopyranoside-, (25S)-spirost-5-ene-1 beta,3 beta-diol [(25S)-ruscogenin] 1-O-{O-alpha-L-rhamnopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1--> 3)]-alpha-L-arabinopyranoside}, neoruscogenin 1-O-{O-alpha-L-rhamnopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1--> 3)]-beta-D-fucopyranoside}, 26-O-beta-D-glucopyranosyl-22-O-methylfurosta-5,25(27)-diene-1 beta,3 beta,22 xi,26-tetrol 1-O--O-alpha-L-rhamnopyranosyl-(1--> 2)-O-[beta-D-xylopyranosyl-(1-->3)]-alpha-L-arabinopyranoside- and 26-O-beta-D-glucopyranosylfurosta-5,20(22),25(27)-triene-1 beta,3 beta,26-triol 1-O-{O-alpha-L-rhamnopyranosyl-(1--> 2)-alpha-L-arabinopyranoside}...
August 1996: Phytochemistry
Y Mimaki, T Kanmoto, Y Sashida, A Nishino, Y Satomi, H Nishino
Three new spirostanol pentaglycosides embracing beta-D-apiofuranose were isolated from the fresh underground parts of Chlorophytum comosum together with four known saponins. The structures of new compounds were determined by spectroscopic data, including two-dimensional NMR, and partial acid-catalysed hydrolysis to be (25R)-5 alpha-spirostane-2 alpha,3 beta-diol 3-O-[O-beta-D-glucopyranosyl- (1-->2)-O-[O-beta-D-apiofuranosyl-(1-->4)-beta-D-glucopyranosyl-(1 -->3)]-O- beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside], (25R)-3 beta-hydroxy-5 alpha-spirostan-12-one (hecogenin) 3-O-[O-beta-D-glucopyranosyl-(1-->2)-O-[O-beta-D-apiofuranosyl-(1- ->4)- beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D- galactopyranoside] and hecogenin 3-O-[O-beta-D-glucopyranosyl-(1-->2)-O-[O-beta-D- apiofuranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)]-O-beta-D-gluc opyranosyl- (1-->4)-beta-D-galactopyranoside], respectively...
March 1996: Phytochemistry
Y Mimaki, T Kanmoto, M Kuroda, Y Sashida, Y Satomi, A Nishino, H Nishino
Three new spirostanol saponins and two new furostanol saponins were isolated from the underground parts of Hosta longipes. Their structures were determined to be (25R)-5 alpha-spirostane-2 alpha, 3 beta-diol (gitogenin) 3-O-{O-alpha-L -rhamnopyranosyl-(1-->2)-beta-D-galactopyranoside}, gitogenin 3-O-{O-alpha-L-rhamnopyranosyl-(1-->2) -O-[beta-D-glucopyranosyl-(1-->4)]-beta-D-galactopyranoside-, (25R)-5 alpha-spirostan-3 beta-ol (tigogenin) 3-O-{O-alpha-L-rhamnopyranosyl-(1-->2) -O-[beta-D-glucopyranosyl-(1-->4)]-beta-D-galactopyranoside-, 26-O-beta-D-glucopyranosyl-22-O-methyl-(25R)-5 alpha-furostane-2 alpha,3 beta, 22 xi,26-tetrol 3-O-{O-alpha-L-rhamnopyranosyl -(1-->2)-beta-D-galactopyranoside} and 26-O-beta -D-glucopyranosyl-22-O-methyl-(25R)-5 alpha-furostane-2 alpha,3 beta,22 xi,26-tetrol 3-O-{O-alpha-L -rhamnopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl -(1-->4)]-beta-D-galactopyranoside}, respectively...
July 1996: Phytochemistry
C Guillemette, D W Hum, A Bélanger
Recent findings obtained by our group showed that incubation of LNCaP cells with labeled steroids leads to the formation of 3- and 17-hydroxysteroid glucuronides. In this study, the specificity and the kinetic properties of 3-hydroxy-C19steroid uridine diphospho-glucuronosyltransferase (3-OH-UGT) and 17-hydroxy-C19steroid UGT (17-OH-UGT) activities in LNCaP cells were investigated. Results indicate that the UGT has a high affinity for testosterone, dihydrotestosterone (DHT), androsterone (ADT) and androstane-3 alpha, 17 beta-diol (3 alpha-DIOL), with Km values ranging from 0...
December 1995: Journal of Steroid Biochemistry and Molecular Biology
P Sourdaine, D H Garnier
Seminiferous lobules of dogfish (Scyliorhinus canicula) testis comprise cysts formed by steroid-producing Sertoli cells associated with germ cells at an identical stage of spermatogenesis. These lobules were isolated in four populations corresponding to lobules with spermatogonia (A), spermatocytes (B), early spermatids (C) and late spermatids (D). They were used for steroid radioimmunoassay or incubated with 22 alpha-hydroxycholesterol or with dibutyryl cyclic AMP (dibutyryl cAMP) to measure steroid production...
January 1993: Journal of Reproduction and Fertility
A D Patil, P W Baures, D S Eggleston, L Faucette, M E Hemling, J W Westley, R K Johnson
Two new glycosides have been isolated from the MeOH extract of the stem wood and stem bark of an Ecuadorian plant Chamaedorea linearis, and their structures have been determined by spectroscopic means and X-ray analysis of the aglycone to be 1-O-[beta-L-fucopyranosyl-(4'-sulfate)]-25R,5 alpha-spirostane-1 beta, 3 beta-diol [1]) and 1-O-[beta-L-fucopyranosyl-(4'-sulfate)]-25R,5 alpha-spirostane-1 alpha, 3 beta-diol [2]. These compounds were identified in a screen for inhibitors of recombinational DNA repair...
September 1993: Journal of Natural Products
M Strömstedt, M Warner, C D Banner, P C MacDonald, J A Gustafsson
The role of brain cytochrome P450 (P450) in regulating the levels of the potent anesthetic steroid 3 alpha-hydroxy-5 alpha-pregnan-20-one (3 alpha-OH-DHP) has been investigated. By analogy with the elimination of androgen from its target tissues, we present evidence that it is 3 beta-hydroxy-5 alpha-pregnan-20-one (3 beta-OH-DHP) and not 3 alpha-OH-DHP that represents the major pathway for the formation of more polar metabolites and thus the elimination of the 5 alpha-reduced metabolites of progesterone from target tissues...
November 1993: Molecular Pharmacology
M J Caballero
In androgen target tissues, testosterone undergoes extensive biotransformation to 5 alpha-dihydrotestosterone which in turn is metabolized into 5 alpha-androstane-3 alpha,17 beta-diol and 5 alpha-androstane-3 beta,17 beta-diol. From studies mainly in the prostate, it has been shown that 5 alpha-androstane-3 beta, 17 beta-diol can be further converted to 5 alpha-androstane-3 beta,6 alpha(beta)/7 alpha(beta),17 beta-triols. The present studies show that among the metabolites of 5 alpha-androstane-3 beta,17 beta-diol in scalp homogenates, three were isolated by thin-layer chromatography and identified against standard steroids: 5 alpha-dihydrotestosterone, epiandrosterone, and 5 alpha-androstanedione...
1994: Hormone Research
C Brosa, S Nusimovich, R Peracaula
The synthesis of four new brassinosteroids with 2 beta,3 beta-diol functionality and A/B cis and A/B trans ring junction is reported. These brassinosteroids could present activity as antiecdysteroids.
August 1994: Steroids
R Sanchez, Y de Launoit, F Durocher, A Bélanger, F Labrie, J Simard
The structures of cDNA clones encoding four members of the rat 3 beta-hydroxysteroid dehydrogenase/delta 5-delta 4 isomerase (3 beta-HSD) family were characterized. The rat type I, type II and the novel type IV are genuine NAD+/H-dependent 3 beta-HSD isoenzymes. On the other hand, the liver-specific type III protein is a specific 3-keto-reductase (3-KSR) that catalyzes the conversion of 5 alpha-androstane-3-one-17 beta-ol (DHT) and 5 alpha-androstane 3,17-dione (A-dione) into their 3 beta-hydroxy metabolites...
July 1994: Molecular and Cellular Endocrinology
G Morali, M V Oropeza, A E Lemus, G Perez-Palacios
To assess whether naturally occurring 5 alpha-androstanediols (5 alpha-androstane-3 alpha, 17 beta-diol and 5 alpha-androstane-3 beta, 17 beta-diol) play a role in the regulation of male sexual behavior in the rat, their capability to restore copulatory behavior in castrated animals was evaluated. Androstanediols were chronically administered either alone or in combination with 5 alpha-dihydrotestosterone (DHT) or with estradiol-17 beta (E2). Animals treated with testosterone (T), DHT, E2, and vehicle, either alone or in different combinations, served as controls...
September 1994: Biology of Reproduction
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