The relationship between a novel NAD(P)H oxidase activity of ovoperoxidase and the CN- -resistant respiratory burst that follows fertilization of sea urchin eggs.

Turner, Eric E.; Somers, Cynthia E.; Shapiro, Bennett M.

doi:10.1016/s0021-9258(17)38852-x

Cited by 33 publications

(7 citation statements)

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“…The previously demonstrated ability of ovothiol C to confer cyanideinsensitive NAD(P)H-Oz oxidoreductase activity on the ovoperoxidase has been confirmed in this study for ovothiol A as well but is not a property of other known biological thiols (Turner et al, 1986). Initially, this suggested a role for ovothiol in this burst of oxygen consumption, with ovoperoxidase participating in production as well as consumption of hydrogen peroxide (Turner et al, 1985(Turner et al, , 1986). Data presented here, however, make a role for ovothiol and the ovothiol-dependent oxidoreductase activity of ovoperoxidase in the respiratory burst much less likely.…”

Section: Discussionsupporting

confidence: 77%

“…"Control value was 1.56 X 105 cpm bound to minutes figure 7: Respiration after fertilization in eggs of 5. purpuratus. Respiration was measured in a Clark 02 electrode as previously described (Turner et al, 1985). Rates represent 1.4 X 10s eggs in a final volume of 5 mL of Millipore-filtered seawater, with ( ) and without (•) 10 mM aminotriazole.…”

Section: Resultsmentioning

confidence: 99%

“…0006-2960/87/0426-4028S01.50/0 such as ergothioneine (Jocelyn, 1972) that contain sulfur at the C-2 position, ovothiol readily undergoes oxidation by atmospheric oxygen or H2G2 to form a disulfide. Ovothiol has been shown to confer NAD(P)H-02 oxidoreductase activity on ovoperoxidase (Turner et al, 1985(Turner et al, , 1986), a heme peroxidase exocytosed at fertilization that cross-links the extraembryonic protein coat (fertilization membrane) with dityrosyl cross-links (Deits et al, 1984;Foerder & Shapiro, 1977).…”

mentioning

confidence: 99%

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Ovothiols, a family of redox-active mercaptohistidine compounds from marine invertebrate eggs

Turner¹,

Klevit²,

Hager³

et al. 1987

Biochemistry

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We have previously reported a novel thiol compound, 1-methyl-N alpha,N alpha-dimethyl-4-mercaptohistidine, or ovothiol, present at high concentration in the eggs of the sea urchin Strongylocentrotus purpuratus [Turner, E., Klevit, R., Hopkins, P. B., & Shapiro, B. M. (1986) J. Biol. Chem. 261, 13056-13063]. Here we report two related compounds, 1-methyl-N alpha-methyl-4-mercaptohistidine, or ovothiol B, from the scallop Chlamys hastata, and 1-methyl-4-mercaptohistidine, or ovothiol A, from the starfish Evasterias troschelii. These two compounds, as well as the S. purpuratus compound now designated ovothiol C, were isolated from eggs or ovarian tissue by S-carboxymethylation with [3H]iodoacetic acid, ion-exchange chromatography and ion-pairing high-pressure liquid chromatography. The structures of S-(carboxymethyl)ovothiols A and B were determined by 1H NMR, and that of ovothiol A was confirmed by comparison with authentic methylhistidine samples after desulfuration with Raney nickel. In the ovary of each species, the predominant methylation form of ovothiol accounts for at least 80% of the total 4-mercaptohistidine. The ovothiol concentration of the ovary far exceeds that of the testis or somatic tissues. The ovothiol C content of unfertilized S. purpuratus eggs is 1.14 mumol/10(6) eggs, equivalent to approximately 4.3 mM average concentration; the glutathione (GSH + GSSG) content is 0.9 mumol/10(6) eggs. In this species, high ovothiol levels persisted for the first 2 weeks of embryonic development. Ovothiol and glutathione account for virtually all of the trichloroacetic acid soluble-SH groups in the egg; these results are compared to several previous studies.(ABSTRACT TRUNCATED AT 250 WORDS)

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Section: Discussionsupporting

confidence: 77%

Section: Resultsmentioning

confidence: 99%

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confidence: 99%

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Ovothiols, a family of redox-active mercaptohistidine compounds from marine invertebrate eggs

Turner¹,

Klevit²,

Hager³

et al. 1987

Biochemistry

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“…Diallyltetrasulfide, if reductively cleaved to form a disulfide and hydrotrisulfide, might release S 2 . The same applies to dimethyltetrasulfide (22) from Scorodophleus zenkeri Harms, whose biological activity is as yet unknown, but which may in theory release S 2 ; and to 1,2,3,4,5,6-hexathiephane (24) from Shiitake mushroom extracts, which might generate a whole cocktail of sulfur agents, including S 2 , S 3 , S 4 and S 5 .…”

Section: Reactive Sulfur Species: Between Knowledge and Speculationmentioning

confidence: 98%

A scent of therapy: pharmacological implications of natural products containing redox-active sulfur atoms

2006

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A range of sulfur-containing natural products from plants, fungi, bacteria and animals have recently been investigated to determine their therapeutic potential. Preliminary in vitro and in vivo studies of compounds such as ergothioneine, ovothiols, allicin, leinamycin, varacin, lenthionine and diallyltetrasulfide have provided evidence for antioxidant, antibacterial, antimicrobial, antifungal and anticancer properties. The biological activity of these compounds is the result of specific chemical properties which converge in chemotypes such as thiols, disulfides, sulfenic and sulfinic acids,thiosulfinates, sulfoxides, sulfones and polysulfides. Redox-activity, catalysis, metal binding, enzyme inhibition and radical generation allow reactive sulfur species to interact with oxidative stressors, to affect the function of redox-sensitive cysteine proteins and to disrupt the integrity of DNA and cellular membranes. In some cases, the biological activity of sulfur-containing plant products depends on initial enzymatic activation, which allows thiosulfinates and isothiocyanates to be generated with high target selectivity. Not surprisingly, research into the biochemical and pharmacological properties of the lesser known sulfur chemotypes is rapidly gathering momentum.

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“…The first suggestion of a biochemical role for the ovothiols arose from investigations into the source of hydrogen peroxide required for the postfertilization hardening of sea urchin eggs' fertilization envelope (Turner et al, 1985). Hardening results from the oxidative cross-linking of tyrosine residues in envelope proteins and protects the embryo from, among other things, fatal polyspermy.…”

mentioning

confidence: 99%

Ovothiols as free-radical scavengers and the mechanism of ovothiol-promoted NAD(P)H-O2 oxidoreductase activity

Holler

Hopkins²

1990

Biochemistry

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Racemic ovothiol A [(+/-)-1a] and the ovothiol model compound 1,5-dimethyl-4-mercaptoimidazole (DMI, 2) were found to scavange the free radicals Fremy's salt (4) and Banfield' radical (5) much more rapidly than did the thiol antioxidant glutathione. Ovothiol A also scavenges the tyrosyl radical, with efficiency comparable to that of ascorbic acid and the tocopherol analogue trolox (3). The ovothiol model compound DMI was found to scavenge superoxide with a rate constant comparable to that of the reaction between superoxide and glutathione. These results suggest both a free-radical scavenging role for the ovothiols and a mechanism by which the ovothiols confer NAD(P)H-O2 oxidoreductase activity upon the enzyme ovoperoxidase. Investigation of this mechanism implicates the ovothiol thiyl radical and the NAD radical as key intermediates. The ovothiyl radical appears to be unreactive toward oxygen but highly reactive toward NADH. An estimate of the one-electron oxidation potential of the ovothiol anion is presented. The physical basis for the stability of the ovothiol free radical is discussed.

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The relationship between a novel NAD(P)H oxidase activity of ovoperoxidase and the CN- -resistant respiratory burst that follows fertilization of sea urchin eggs.

Cited by 33 publications

References 31 publications

Ovothiols, a family of redox-active mercaptohistidine compounds from marine invertebrate eggs

Ovothiols, a family of redox-active mercaptohistidine compounds from marine invertebrate eggs

A scent of therapy: pharmacological implications of natural products containing redox-active sulfur atoms

Ovothiols as free-radical scavengers and the mechanism of ovothiol-promoted NAD(P)H-O2 oxidoreductase activity

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