19-Hydroxyprostaglandin E1 as a major component of the semen of primates

Kelly, Rodney W.; Taylor, Philip L.; Hearn, Jack; Short, R. V.; Martin, David E.; Marston, J. H.

doi:10.1038/260544a0

Cited by 71 publications

(15 citation statements)

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“…In most species, the 20:3 n-6 content of tissue phospholipids is far lower than the content of AA, and prostaglandins of the 2-series predominate. However, human and monkey seminal vesicles contain high levels of the 1-series prostaglandins, especially 19-hydroxy-prostaglandin E 1 (PGE 1 ), derived from 20:3 n-6 (36,37). In rhesus monkey semen, 19-hydroxy-PGE 1 is present at five times the level of 19-hydroxy-PGE 2 .…”

Section: Downloaded Frommentioning

confidence: 99%

Selective changes of docosahexaenoic acid-containing phospholipid molecular species in monkey testis during puberty

Lin

Neuringer

Connor

2004

Journal of Lipid Research

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Puberty has a profound effect upon the biochemical composition of the testis. We previously demonstrated that puberty was accompanied by great increases in the content of docosahexaenoic acid (DHA; 22:6 n-3) and dihomogamma-linoleic acid (20:3 n-6) and decreases in arachidonic acid (AA; 20:4 n-6) in the phospholipids of testis. In this report, we analyze the composition of the phospholipid molecular species of the ethanolamine and choline glycerophospholipids in the testis of prepubertal (2 years old) and young adult (7-8 years old) monkeys, There was an increase in the DHA species and a decrease in arachidonic species. Interestingly, with few exceptions, among the three molecules with DHA or AA at the sn-2 position, only 16:0-22:6 and 18:0-20:4 changed selectively in opposite directions for both ethanolamine and choline glycerophospholipids. In contrast, there was no such selectivity seen in molecular species containing dihomogamma-linoleic acid or linoleic acid at the sn-2 position. All three dihomogamma-linoleic acid species increased and all three linoleic acid species decreased during puberty. In summary, at puberty, i.e., the onset of spermatogenesis, there are selective changes in the phospholipid molecular species, particularly those containing DHA and AA. These changes suggest a specific functional role of DHA-containing molecular species in the lipid bilayer membranes of sperm cells. A possible link between the composition of DHA-phospholipid molecular species and cellular function is discussed. -Lin, D. S., M. Neuringer, and W. E. Connor. Selective changes of docosahexaenoic acid-containing phospholipid molecular species in monkey testis during puberty. J. Lipid Res. 2004. 45: 529-535.

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Section: Downloaded Frommentioning

confidence: 99%

Selective changes of docosahexaenoic acid-containing phospholipid molecular species in monkey testis during puberty

Lin

Neuringer

Connor

2004

Journal of Lipid Research

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“…PGD compounds, have not been detected in human seminal fluid. The rapid biosynthesis of 19-hydroxy-PGE 1 and 19-hydroxy-PGE 2 in vivo suggests that PGH synthase, PGH 19-hydroxylase, and PGE synthase are closely linked (1,2,4). A proposed mechanism for biosynthesis of (19R)-hydroxy-PGE 2 in human seminal vesicles is shown in Fig.…”

Section: Fig 3 Lc-ms Analysis Of Pg Compounds Formed During Incubatmentioning

confidence: 99%

“…Recombinant CYP4A11 and microsomes from human kidneys hydroxylate U-44069 at the -side chain. 2 The NADPHdependent metabolism of PGH 2 in the kidney and other tissues merits further investigation.…”

Section: Fig 3 Lc-ms Analysis Of Pg Compounds Formed During Incubatmentioning

confidence: 99%

Identification of CYP4F8 in Human Seminal Vesicles as a Prominent 19-Hydroxylase of Prostaglandin Endoperoxides

Bylund

Hidestrand

Ingelman‐Sundberg

et al. 2000

Journal of Biological Chemistry

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“…The absolute stereochernistry of the newly introduced hydroxyl group at C-7' in 6 has been determined to be (R) by conversion of 6 to the acetate 7 and oxidation of the latter to give, following methylation of the corresponding acid, (R)-(-)-methyl 6-acetoxyheptanoate (39). An authentic sample of this compound was prepared, as its (S)-(+) enantiomer, following resolution of ethyl 6-phthaloxyheptanoate (37) as the brucine salt.…”

Section: Resultsmentioning

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-Hydroxyprostaglandin E1 as a major component of the semen of primates

Cited by 71 publications

References 10 publications

Selective changes of docosahexaenoic acid-containing phospholipid molecular species in monkey testis during puberty

Selective changes of docosahexaenoic acid-containing phospholipid molecular species in monkey testis during puberty

Identification of CYP4F8 in Human Seminal Vesicles as a Prominent 19-Hydroxylase of Prostaglandin Endoperoxides

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-Hydroxyprostaglandin E1 as a major component of the semen of primates

Cited by 71 publications

References 10 publications

Selective changes of docosahexaenoic acid-containing phospholipid molecular species in monkey testis during puberty

Selective changes of docosahexaenoic acid-containing phospholipid molecular species in monkey testis during puberty

Identification of CYP4F8 in Human Seminal Vesicles as a Prominent 19-Hydroxylase of Prostaglandin Endoperoxides

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