19-Hydroxy-prostaglandin e and infertility in human males

Lewy, Robert Ira; Bills, T K; Dalton, John R.; Smith, J B; Silver, Melvin J.

doi:10.1016/0161-4630(79)90109-5

Cited by 13 publications

(4 citation statements)

References 13 publications

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Section: Summary Of the Results Reported By Human Clinical Trialsmentioning

confidence: 78%

“…However, other evidence has shown that the semen of fertile men contains higher levels of PGs with respect to semen of infertile men [49,50]. 19-OH-PGE and PGE levels were significantly decreased in the semen of 10 infertile males [49]. In addition, it was found that PGs levels in the semen of hypogonadal men were correlated with testosterone concentration in the blood [51].…”

Section: Summary Of the Results Reported By Human Clinical Trialsmentioning

confidence: 89%

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Arachidonic Acid Pathways and Male Fertility: A Systematic Review

Hoxha

Barbonetti

Zappacosta

2023

IJMS

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Arachidonic acid (AA) is a polyunsaturated fatty acid that is involved in male fertility. Human seminal fluid contains different prostaglandins: PGE (PGE1 and PGE2), PGF2α, and their specific 19-hydroxy derivatives, 18,19-dehydro derivatives of PGE1 and PGE2. The objective of this study is to synthesize the available literature of in vivo animal studies and human clinical trials on the association between the AA pathway and male fertility. PGE is significantly decreased in the semen of infertile men, suggesting the potential for exploitation of PGE agonists to improve male fertility. Indeed, ibuprofen can affect male fertility by promoting alterations in sperm function and standard semen parameters. The results showed that targeting the AA pathways could be an attractive strategy for the treatment of male fertility.

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Section: Summary Of the Results Reported By Human Clinical Trialsmentioning

confidence: 78%

Section: Summary Of the Results Reported By Human Clinical Trialsmentioning

confidence: 89%

Arachidonic Acid Pathways and Male Fertility: A Systematic Review

Hoxha

Barbonetti

Zappacosta

2023

IJMS

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“…GnRH is implicated in reproductive health, as this hormone stimulates the production of luteinizing hormone (LH) and follicle‐stimulating hormone (FSH), which in turn stimulates production of testosterone in the Leydig cells and inhibin B in the Sertoli cells of the testis. The connection between the arachidonic acid pathway and reproductive health may be mediated through prostaglandins (one of the major downstream metabolites of arachidonic acid) as some studies have reported differences in prostaglandin levels in relation to fertility (Lewy et al. , 1979), including masculinization in animal models (Wright & McCarthy, 2009).…”

Section: Discussionmentioning

confidence: 99%

Association between chemical pattern in breast milk and congenital cryptorchidism: modelling of complex human exposures

et al. 2012

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During the past four decades, there has been an increase in the incidence rate of male reproductive disorders in some, but not all, Western countries. The observed increase in the prevalence of male reproductive disorders is suspected to be ascribable to environmental factors as the increase has been too rapid to be explained by genetics alone. To study the association between complex chemical exposures of humans and congenital cryptorchidism, the most common malformation of the male genitalia, we measured 121 environmental chemicals with suspected or known endocrine disrupting properties in 130 breast milk samples from Danish and Finnish mothers. Half the newborns were healthy controls, whereas the other half was boys with congenital cryptorchidism. The measured chemicals included polychlorinated biphenyls (PCBs), polybrominated diphenyl-ethers, dioxins (OCDD/PCDFs), phthalates, polybrominated biphenyls and organochlorine pesticides. Computational analysis of the data was performed using logistic regression and three multivariate machine learning classifiers. Furthermore, we performed systems biology analysis to explore the chemical influence on a molecular level. After correction for multiple testing, exposure to nine chemicals was significantly different between the cases and controls in the Danish cohort, but not in the Finnish cohort. The multivariate analysis indicated that Danish samples exhibited a stronger correlation between chemical exposure patterns in breast milk and cryptorchidism than Finnish samples. Moreover, PCBs were indicated as having a protective effect within the Danish cohort, which was supported by molecular data recovered through systems biology. Our results lend further support to the hypothesis that the mixture of environmental chemicals may contribute to observed adverse trends in male reproductive health.

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“…Furthermore, the absolute stereochemistry at C-19 in the human metabolite 19-hydroxy-PGB has been identified as (R) (44), identical to that observed in the present study. The 19-hydroxy-PG's, particularly in the PGE series ( 4 9 , have greater physiological effects on smooth muscle than do the parent PG's (46), and are used in treatment of male infertility attributable to lack of seminal fluid PGEl metabolites (47).…”

Section: Discussionmentioning

confidence: 99%

Hydroxylation of prostanoids by fungi. Synthesis of (−)-15-deoxy-19-(R)-hydroxy-PGE₁ and (−)-15-deoxy-18-(S)-hydroxy-PGE₁

Holland¹,

Brown²,

Chenchaiah³

et al. 1990

Can. J. Chem.

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A series of racemic substituted cyclopentanones, with alkyl groups corresponding to the upper prostanoid side chain and (or) the lower prostanoid side chain without the C-15 alcohol, has been synthesized. Using a steroid template for the prostanoid molecule as a basis for selection, fungi capable of hydroxylating steroids have been used to biotransform the prostanoid substrates. The predominant products were hydroxylated at the prostanoid C-18 and C-19 positions. The hydroxylations were enantioselective, with excesses in the range 10-60%, and in most cases the predominant configuration corresponded to that of the natural prostanoids. The stereochemistry of the C-19 hydroxyl group was found to be R by degradation of products to methyl 6-acetoxyheptanoate and comparison of that material with a resolved sample, obtained via crystallization of the brucine salt of ethyl 6-phthaloxyheptanoate. Hydroxylation at C-18 gave the S configuration of alcohol. Hydroxylation at prostanoid C-15 was observed, but in all cases this was accompanied by other reactions. Hydroxylation of Rhizopus arrhizus has been used in a preparation of ( Chem. 68, 282 (1990). On a synthttist une sCrie de cyclopentanones substitukes ractmiques portant des groupements alkyles correspondant a la chaine laterale prostano'ide supCrieure et (ou) a la chaine lathale prostanoide infkrieure ne portant pas la fonction alcool en C-15. Utilisant comme base de sClection un gabarit stCroi'dal pour representer la molCcule prostanoi'de, on a fait appel a un champignon capable d'hydroxyler les stkroides pour effectuer la biotransformation des substrats prostanoldes. Les produits principaux sont les prostano'ides hydroxylCs en positions C-18 et C-19. Les hydroxylations sont CnantiosClectives, avec des excks de l'ordre de 10-60%, et, dans la plupart des cas, la configuration prCdominante correspond a celle des prostanoYdes naturels. En se basant sur une dkgradation des produits en 6-acCtoxyheptanoate de mCthyle et sur une comparaison de ce produit avec un Cchantillon rtsolu, obtenu par cristallisation du sel de brucine du 6-phtaloxyheptanoate d'ithyle, on a dCmontrC que la stCrCochimie du groupement hydroxyle en C-19 est R. L'hydroxylation en C-18 foumit un alcool de configuration S. On a observt une hydroxylation en C-15 du prostano'ide; toutefois, cette reaction est toujours accompagnee par d'autres reactions. On a fait appel une hydroxylation par le Rhizopus arrhizus pour la prkparation des (-)-15-dCsoxy-19-(R)-hydroxy-PGWI et (-)-15-dCsoxy-18-(S)-hydroxy-PGW,.

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19-Hydroxy-prostaglandin e and infertility in human males

Cited by 13 publications

References 13 publications

Arachidonic Acid Pathways and Male Fertility: A Systematic Review

Arachidonic Acid Pathways and Male Fertility: A Systematic Review

Association between chemical pattern in breast milk and congenital cryptorchidism: modelling of complex human exposures

Hydroxylation of prostanoids by fungi. Synthesis of (−)-15-deoxy-19-(R)-hydroxy-PGE₁ and (−)-15-deoxy-18-(S)-hydroxy-PGE₁

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19-Hydroxy-prostaglandin e and infertility in human males

Cited by 13 publications

References 13 publications

Arachidonic Acid Pathways and Male Fertility: A Systematic Review

Arachidonic Acid Pathways and Male Fertility: A Systematic Review

Association between chemical pattern in breast milk and congenital cryptorchidism: modelling of complex human exposures

Hydroxylation of prostanoids by fungi. Synthesis of (−)-15-deoxy-19-(R)-hydroxy-PGE1 and (−)-15-deoxy-18-(S)-hydroxy-PGE1

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Hydroxylation of prostanoids by fungi. Synthesis of (−)-15-deoxy-19-(R)-hydroxy-PGE₁ and (−)-15-deoxy-18-(S)-hydroxy-PGE₁