Isolation and structure of a new sulphur-containing aminoacid from sea urchin eggs

Palumbo, Anna; d’Ischia, Marco; Misuraca, Giovanna; Prota, Giuseppe

doi:10.1016/s0040-4039(00)88597-4

Cited by 49 publications

(34 citation statements)

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“…Although no 13C-or 'H-NMR data for the bimane-ovothiol A derivative 2 were available in the literature, reasonable agreement with some related literature values were found [18,20,211. Selman-Reimer et al [17] emphasized the fact that the absolute positions of protons were a sensitive function of the sample pH.…”

Section: Tional Karlsruhe) Values For (S)-(4-methoxyphenyl)-methyl-~-supporting

confidence: 73%

Identification of a major low‐molecular‐mass thiol of the trypanosomatid Crithidia fasciculata as ovothiol A

Steenkamp

Spies

1994

European Journal of Biochemistry

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An unidentified low-molecular-mass thiol, U23, previously detected as the 7-diethylamino-3-(4'-maleimidylphenyl)-4-methylcoumarin derivative in extracts of the trypanosome Crithidiu fusciculutu, was purified as the bimane derivative. Resonances attributable to U23 were discerned from those of the bimane label by comparison of the 'H-and IT-NMR spectra of monobromobimane and U23-bimane. The complete 'H-and I3C-NMR spectra of U23-bimane were assigned by means of 'H-'H correlation spectroscopy, 'H-''C correlation spectroscopy and 13C multiplicity determinations. The results indicated identity of U23 with 1-N-methyl-4-mercaptohistidine (ovothiol A), previously isolated from marine sources. This assignment was confirmed by NOE difference experiments, fast-atom-bombardment mass spectrometry of U23-bimane and ultraviolet/visible spectrophotometry of U23, which was isolated as the disulfide. The isolation of ovothiol A from a parasitic protozoan suggest that the 4-mercaptohistidines may have a wider distribution and function as Several antioxidant thi& than was hitherto realized. mechanisms which enable trypanosomes to withstand oxidative killing by phagocytic macrophages seem to be operative. The microbicidal effects of reactive oxygen species released by the macrophages can be evaded by interference with signal transduction processes which trigger the respiratory burst. Such a mechanism probably accounted for the observed reduction in the magnitude of the respiratory burst when neutrophils were incubated with the surface membrane acid phosphatase of Leishmania donovuni [l]. In addition trypanosomes, like other organisms exposed to an aerobic environment, depend on both enzymic and non-enzymic mechanisms for the removal of reactive oxygen species (reviewed in [2] and [3]). However, while they possess superoxide dismutase, trypanosomes are deficient in catalase and various peroxidases, including glutathione peroxidase, which, in mammalian cells, are responsible for the removal of hydrogen peroxide, the product of the superoxide-dismutase-catalysed reaction [4]. Hydrogen peroxide is the immediate precursor of the reactive hydroxyl radical, which can be regarded as the most damaging of the reactive oxygen intermediates [5]. A peroxidase activity dependent on the unique trypanosomal metabolite, trypanothione [2, 51, has been detected [6, 71. The enzyme, however, has not yet been characterized and its activity was estimated to be quite low when compared with glutathione peroxidase in mammalian tissues [3]. The lack of adequate enzymatic mechanisms for the detoxification of hydrogen peroxide is thought to render trypanosomes susceptible to oxidative stress and to form the basis for the anti-trypanosomal activity of several drugs [3].On the other hand, evidence was presented that trypanosomes are able to metabolize exogenously added peroxide [7, 81 and that this process is inhibited by sulfhydryl reagents. Low-molecular-mass thiols, and particularly trypanothione [2, 31, are, therefore, thought to play an important role in ...

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Section: Tional Karlsruhe) Values For (S)-(4-methoxyphenyl)-methyl-~-supporting

confidence: 73%

Identification of a major low‐molecular‐mass thiol of the trypanosomatid Crithidia fasciculata as ovothiol A

Steenkamp

Spies

1994

European Journal of Biochemistry

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“…Dysideanin A (1) may be related to a family of thiol-containing amino acids, namely ovothiols A-C, 24 and L-ovithiol A disulfide. 20,25 Dysideanin B (2) is structurally related to dragmacidonamines A and B, 19 hyrtiomanzamine, 26 gesashidine A 22 and didemnolines A-D. 27,28 Owing to the known antibiotic activity of b-carboline alkaloids 28 and diketopiperazines, 29 compounds 1-4 were subjected to an antibacterial agar diffusion assay. Dysideanin B (2) exhibited antibacterial activity that showed zones of inhibition toward Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Vibrio alginolyticus (20 mg per 5-mm f disk, 8.0, 7.5, 8.0 and 8.5 mm, respectively), whereas compounds 1, 3 and 4 were not active.…”

Section: Resultsmentioning

confidence: 99%

Two novel alkaloids from the South China Sea marine sponge Dysidea sp.

Ren

Tian

et al. 2010

J Antibiot

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“…This 5-thiohistidine has been isolated for the first time from sea urchin eggs, which resulted in its naming ovothiol. 4,5,6 The unique antioxidant properties 7,8,9 and the broad distribution among marine invertebrates, microalgae and proteobacteria provide reason to believe that ovothiol A and its derivatives ovothiol B and C (2 & 3, Figure 1) play important roles in cellular biochemistry. 10,11 In the past, systematic investigations on the physiological function of thiohistidines were difficult, because the origin and distribution of these compounds was obscure.…”

Section: Background and Open Challengesmentioning

confidence: 99%

On ovothiol biosynthesis and biological roles: from life in the ocean to therapeutic potential

Castellano

Seebeck

2018

Nat. Prod. Rep.

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Covering: up to 2018Ovothiols are sulfur-containing natural products biosynthesized by marine invertebrates, microalgae, and bacteria. These compounds are characterized by unique chemical properties suggestive of numerous cellular functions. For example, ovothiols may be cytoprotectants against oxidative stress, serve as building blocks of more complex structures and may act as molecular messengers for inter- and intracellular signaling. Detailed understanding of ovothiol physiological role in marine organisms may unearth novel concepts in cellular redox biochemistry and highlight the therapeutic potential of this antioxidant. The recent discovery of ovothiol biosynthetic genes has paved the way for a systematic investigation of ovothiol-modulated cellular processes. In this highlight we review the early research on ovothiol and we discuss key questions that may now be addressed using genome-based approaches. This highlight article provides an overview of recent progress towards elucidating the biosynthesis, function and potential application of ovothiols.

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Isolation and structure of a new sulphur-containing aminoacid from sea urchin eggs

Cited by 49 publications

References 1 publication

Identification of a major low‐molecular‐mass thiol of the trypanosomatid Crithidia fasciculata as ovothiol A

Identification of a major low‐molecular‐mass thiol of the trypanosomatid Crithidia fasciculata as ovothiol A

Two novel alkaloids from the South China Sea marine sponge Dysidea sp.

On ovothiol biosynthesis and biological roles: from life in the ocean to therapeutic potential

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