The synthesis of 16-androstene sulfoconjugates from primary porcine Leydig cell culture

The Uptake and Deconjugation of Androstenone Sulfate in the Adipose Tissue of the Boar

“…The STS-mediated hydrolysis of androstenone sulfate did not result in the production of a C 3 hydroxysteroid, but rather returned the parent compound (androstenone), which is a C 3 keto steroid. Consistent with our results, it has been previously reported that chemical hydrolysis of androstenone sulfate returns free androstenone and not a hydroxylated metabolite [9]. On the basis of the results of the present study, we predict that the STSmediated hydrolysis of androstenone sulfate results in the production of the same 3-enol intermediate that is suspected to facilitate sulfoconjugation, with stabilization resulting in the movement of a double bond between C 3 and C 4 to the 3-keto position to produce free androstenone (Figure 6).…”

“…chemical hydrolysis of androstenone sulfate returns free androstenone and not a h ylated metabolite [9]. On the basis of the results of the present study, we predict t STS-mediated hydrolysis of androstenone sulfate results in the production of the s enol intermediate that is suspected to facilitate sulfoconjugation, with stabilization ing in the movement of a double bond between C3 and C4 to the 3-keto position to p free androstenone (Figure 6).…”

“…The sulfoconjugation of androstenone is thought to require enolisation of the 3-keto group to produce a 3-enol intermediate, which can accept a sulfonate group from PAPS. Recently, a metabolite tentatively identified as androst-3-enol-3-sulfate was detected by liquid chromatography–mass spectrometry from Leydig cell culture and was found to return free androstenone, and not a hydroxylated metabolite, following chemical removal of the sulfate group [ 9 ]. Additionally, we have previously demonstrated that androstenone sulfate has a low binding capacity for porcine albumin, which is the carrier protein responsible for the transport of various steroids in the boar including free androstenone [ 10 , 11 ].…”

Pork Production with Entire Males: Directions for Control of Boar Taint

“…Approximately 70% of the 16-androstene steroids produced in the Leydig cells are present as sulfoconjugates in the peripheral circulation [30,31]; no glucuronidated forms of androstenone have been identified from Leydig cell culture. Leydig cells produce two forms of androstenone sulfate, tentatively identified as androst-3-enol-3-sulfate and androstenone-4-sulfate, which both regenerate the parent compound androstenone and not a hydroxylated metabolite following removal of the sulfate group [31] (Figure 3). This suggests that androstenone sulfate may function like many steroid sulfates, acting as a steroid reservoir that can be enzymatically deconjugated by steroid sulfatase (STS) to return free androstenone [31,32].…”

“…Leydig cells produce two forms of androstenone sulfate, tentatively identified as androst-3-enol-3-sulfate and androstenone-4-sulfate, which both regenerate the parent compound androstenone and not a hydroxylated metabolite following removal of the sulfate group [31] (Figure 3). This suggests that androstenone sulfate may function like many steroid sulfates, acting as a steroid reservoir that can be enzymatically deconjugated by steroid sulfatase (STS) to return free androstenone [31,32]. but subsequent cloning and expression of porcine SULT2B1 demonstrated that this was not the case [27].…”