The Isolation and Identification of Androstenediol Sulfate from Spermatic Vein Blood and Testes of the Boar

Abstract

RAESIDE, J. I., AND HOWELES, G . A. The isogation and identification of androstenedioi sulfate from spermatic vein blood and testes of the boar. Can. J. Biochern. 49, 80-84 (1971).A method is described for the extraction and purification of steroid sulfates from testicdar tissues and blood of the boar. Androsteraediol sulfate (3b91'9S-dihydroxy-5-andPo9tene 3-sulfate) was isolated from extracts of both spermatic vein blood and boar testis. Final identification was achieved by infrared spectroscopy, as the ammsnium salt of androstenediol 3-sulfate 17-acetate. Additional evidence of identity was obtained with the 3-monosulfate of androstenediol-7a-"H as an internal standard in several chromatographic systems for steroid sulfates, and for free steroids after hydrolysis. Androstenediol sulfate was not detected in peripheral or spermatic arterial blood, and it was concluded that andrsstenediol sulfate is a major secretory product of the boar testis. RAESIDE, J. I., ET MOWELIS, G. A. m e isolation and identification of androstenediol sulfate from spermatic vein blood and testes of the boar. Can. 3. Biochem. 49, 80-84 (19'71).Ce travail decrit une mdthode d'extraetion et de purification des sulfates de stkroldes B partir de tissus testiculaires et de sang de samglier. Ee sulfate d9androstenediol (3D,1918-dihydroxy-5-androst6ne 3-sulfate) a Ct C isole a partir d9extraits de sang de veine spermatique et de testicule de sanglier. E9identification finale a Ctk effectuke par spectroscopic infrarouge; il s'agit de l'androstdndiol 3-sulfate 17-acktate sous forme de sel d9arnmonium. Cette identit6 a 6tk vkrifike en outre par un standard de rkfkrence, B e 3-monosulfate d'androst&nediol-701-~H, utiIis6 dans plusieurs systemes chromatographiques pour les sulfates de st6rofdes et pour les stkoides Iibres apres hydrolyse, be sulfate d9androstenedioI n'ayant pas Ct C dkele au niveau du sang pCripherique ou de 19artkre spermatique il est conch que Ie sulfate d9androstenediol est un produit de s6crktion majeur du testicule de sanglier. Inbodnetionsulfate from the testes and spermatic vein blood Testosterone has been isolated from the boar testis (1) and spermatic vein blood (21, in which dehydroepiandrosterone s u l f a t e b a s detected also (31, Subsequently, dehydroepisandrosterone and dehydroepiandrosterone sulfate were isolated from the testes and the spermatic vein plasma of a boar receiving human chorica;nZc gonadotrophin $4). Testosterone and dehydroepiandrosterone sulfate appeared to be the most important steroids in both testes and spermatic vein plasma.A preliminary report from our laboratory suggested that androstenediol sulfate was quantitatively a more important csmpsund in the spermatic vein blood of the boar (5). Since androstenediol sulfate may serve as a precursor of testosterone (6) and androstenediol has androgenic activity of its own (' 71, we wish to report the isolation and identification of andrsstenedisl 'This research was supported by the Ontario Department of Agriculture and Food.following trivial names have...

Changes With Age in the Occurrence of C19 Steroids in the Testis and Submaxillary Gland of the Boar

“…Studies on the production of testicular androgens in the dog (Oh & Tamaoki, 1973) have shown that testosterone can be synthesized from 3/?-hydroxy-5-ene-C19 steroids without the intermediate formation of androstenedione. The significant amounts of dehydroepiandrosterone sulphate (Baulieu et al, 1967) and 5-androstenediol sulphate (Raeside & Howells, 1971) which were found in the testis and spermatic vein blood of the boar suggests that the 5-ene pathway to testosterone may be important in this species.…”

Synthesis of free and sulphoconjugated 16-androstene steroids by the Leydig cells of the mature domestic boar

“…Plasma concentrations of many steroid sulphates are substantially higher than that of their unconjugated forms [14,15]. In fact, dehydroepiandrosterone (DHEA) has been reported to be present primarily as a sulphoconjugate in porcine plasma, such that only 10-15% is in the nonconjugated form [16].…”

A study of some major testicular steroids in the pig in relation to their effect on the development of male characteristics in the prepubertally castrated boar

“…The testis of the male pig produces, in addition to testosterone, large quantities of other C,9 steroids (Baulieu, Fabre-Jung & Huis in't Veld, 1967;Raeside & Howells, 1971; Ruokonen & Vihko, 1974;Segal & Raeside, 1975;Booth, 1975). Some of these C19 steroids, notably dehydroepiandrosterone (DHA) and 5-androstenediol may be important precursors of testosterone in the pig testis, as they are in the testis of dogs (Yamaji, Motohashi, Tanioka & Ibayashi, 1968;Oh & Tamaoki, 1973) and man (Vihko & Ruokonen, 1975).…”