ChemInform Abstract: SIMPLE PRENYLATED HYDROQUINONE DERIVATIVES FROM THE MARINE UROCHORDATE APLIDIUM CALIFORNICUM. NATURAL ANTICANCER AND ANTIMUTAGENIC AGENTS

Howard, Bruce; CLARKSON, K.; Bernstein, R. L.

doi:10.1002/chin.198008179

Cited by 12 publications

(19 citation statements)

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“…The presence of one prenyl chain and its position on the aromatic ring was established by 2D NMR and MS spectra. All spectra data were in agreement with previously published data for both natural (Howard et al, 1979) and synthetic 2-(3-methylbut-2-enyl)benzene-1,4-diol (mono-prenyl hydroquinone) (Connon & Blechert, 2003;Yang et al, 2007).…”

Section: Isolation Purification and Structural Characterisation Of Tsupporting

confidence: 71%

“…The organic extract (*4 mg) was initially fractionated by flash chromatography by using an acetonitrile/water gradient elution. The fraction containing UV absorbing compounds (by thin layer chromatography analysis), or the toxic compound obtained by semi-preparative HPLC, was then subjected to analytical HPLC by using an acetonitrile/ water isocratic elution to afford a pure compound which was later analysed by a combination of spectroscopic methods (1D and 2D NMR, MS) and comparison with the literature data (Howard et al, 1979;Yang et al, 2007).…”

Section: Isolation Purification and Structural Characterisation Of Tmentioning

confidence: 99%

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Chemical defence by mono-prenyl hydroquinone in a freshwater ciliate, Spirostomum ambiguum

et al. 2011

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Several species of ciliates produce and accumulate low molecular weight toxic compounds in specialised membrane-bound ejectable organelles: extrusomes. These compounds can be used in predator–prey interaction for killing prey as well as for chemical defence. Here, we describe the isolation and characterisation of 2-(3-methylbut-2-enyl)benzene-1,4-diol(mono-prenyl hydroquinone), the extrusomal defensive toxin of the freshwater heterotrich ciliate Spirostomum ambiguum. The toxin was purified at homogeneity by RP-HPLC, and its structural characterisation was carried out through NMR and MS measurements. In vivo experiments involving S. ambiguum and Climacostomum virens in predator–prey interaction, and the analysis of cytotoxic activity of mono-prenyl hydroquinone on a panel of free-living freshwater ciliates, indicated that the toxin is very effective in S. ambiguum’s chemical defence

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Section: Isolation Purification and Structural Characterisation Of Tsupporting

confidence: 71%

Section: Isolation Purification and Structural Characterisation Of Tmentioning

confidence: 99%

Chemical defence by mono-prenyl hydroquinone in a freshwater ciliate, Spirostomum ambiguum

et al. 2011

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“…In spite of the fact that polyprenylated 1,4-benzoquinones and hydroquinones are very common in nature, to the best of our knowledge, only one related marine metabolite, 2-(3-methylbuten-2-yl)- [1,4] hydroquinone (20), was earlier studied for its cancer protective properties. To establish the cancer preventive activity of this metabolite, the modified Ames assay for mutagenicity of benzo(a)-pyrene, aflatoxin B1, or UV against Salmonella typhimurium was used (40).…”

Section: Discussionmentioning

confidence: 99%

“…Sponges contain prenylated 1,4-benzoquinones and hydroquinones with linear and longer (up to nine prenyl units) terpenoid side chains (14)(15)(16)(17). Ascidians of the genus Aplidium have previously yielded about a dozen prenylated quinones and related compounds (20)(21)(22)(23)(24)(25).…”

Section: Introductionmentioning

confidence: 99%

“…The previously described marine polyprenylbenzoquinones and hydroquinones contain a terpenoid portion ranging from one to nine prenyl units. These quinones have been isolated from brown algae of the order Fucales (10-13), sponges (14)(15)(16)(17), alcyonaceans (18), gorgonaceans (19), and ascidians belonging to the genus Aplidium (20)(21)(22)(23)(24)(25). Brown algae contain diprenyl-, triprenyl-, and tetraprenylquinones and hydroquinones (10)(11)(12)(13).…”

Section: Introductionmentioning

confidence: 99%

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Evaluation of Cancer-Preventive Activity and Structure–Activity Relationships of 3-Demethylubiquinone Q2, Isolated from the Ascidian Aplidium glabrum, and its Synthetic Analogs

et al. 2006

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Purpose-3-Demethylubiquinone Q 2 (1) was isolated from the ascidian Aplidium glabrum. The cancer preventive properties and the structure-activity relationship for 3-demethylubiquinone Q2 (1) and 12 of its synthetic analogues (3-14) are reported.Methods-Compounds 3-14, having one or several di-or triprenyl substitutions and quinone moieties with methoxyls in different positions, were synthesized. The cancer preventive properties of compounds 1 and 3-14 were tested in JB6 Cl41 mouse skin cells, using a variety of assessments, including the MTS assay, flow cytometry, and soft agar assay. Statistical nonparametric methods were used to confirm statistical significance.Results-All quinones tested were shown to inhibit JB6 Cl41 cell transformation, to induce apoptosis, AP-1 and NF-κB activity, and to inhibit p53 activity. The most promising effects were indicated for compounds containing two isoprene units in a side chain and a methoxyl group at the para-position to a polyprenyl substitution.Conclusions-Quinones 1 and 3-14 demonstrated cancer preventive activity in JB6 Cl41 cells, which may be attributed to the induction of p53-independent apoptosis. These activities depended on the length of side chains and on the positions of the methoxyl groups in the quinone part of the molecule.Keywords marine prenylated quinones; cancer prevention; apoptosis; nuclear factor; structure-activity relationship ABBREVIATIONS 3-demethylubiquinone Q2. 2,3-dimethoxy-5-(3′,7′-dimethyl-octa-2′(E),6′-dienyl)- [1,4] benzoquinone (1); EGF, epidermal growth factor; TPA, 12-O-tetradecanoyl-phorbol-13-acetate; FBS, fetal bovine serum; MEM, minimum essential medium

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Inhibition of rat liver microsomal lipid peroxidation elicited by simple 2,2-dimethylchromenes and chromans structurally related to precocenes

Casas¹,

Gorchs²,

Sánchez‐Baeza³

et al. 1992

J. Agric. Food Chem.

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ChemInform Abstract: SIMPLE PRENYLATED HYDROQUINONE DERIVATIVES FROM THE MARINE UROCHORDATE APLIDIUM CALIFORNICUM. NATURAL ANTICANCER AND ANTIMUTAGENIC AGENTS

Abstract: Im Zusammenhang mit der Aufklärung von Naturstoffen wird die Reaktion von Hydrochinon (I) mit (II) zu den Substitutionsprodukten (III) und (IV) sowie deren weitere Cyclisierung bzw. Oxidation zu z.B. (V) oder (VI) untersucht.

Cited by 12 publications

References 1 publication

Chemical defence by mono-prenyl hydroquinone in a freshwater ciliate, Spirostomum ambiguum

Chemical defence by mono-prenyl hydroquinone in a freshwater ciliate, Spirostomum ambiguum

Evaluation of Cancer-Preventive Activity and Structure–Activity Relationships of 3-Demethylubiquinone Q2, Isolated from the Ascidian Aplidium glabrum, and its Synthetic Analogs

Inhibition of rat liver microsomal lipid peroxidation elicited by simple 2,2-dimethylchromenes and chromans structurally related to precocenes

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