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2,3-diarylxanthones as strong scavengers of reactive oxygen and nitrogen species: a structure-activity relationship study.
Bioorg Med Chem. 2010 Sep 15; 18(18):6776-84.BM

Abstract

Xanthones are a class of oxygen-containing heterocyclic compounds widely distributed in nature. The natural derivatives can present different substitutions in the xanthone core that include hydroxyl, methoxyl, prenyl and glycosyl groups. The inclusion of aryl groups has only been reported for a few synthetic derivatives, the 2,3-diaryl moiety being recently introduced by our group. Xanthones are endowed with a broad spectrum of biological activities, many of them related to their antioxidant ability, including the scavenging of reactive oxygen species (ROS) and reactive nitrogen species (RNS), as well as metal chelating effects. Considering the interesting and promising antioxidant activities present in compounds derived from the xanthone core, the main goal of this work was to evaluate the scavenging activity of the new 2,3-diarylxanthones for ROS, including superoxide radical (O2-), hydrogen peroxide (H2O2), singlet oxygen (1O2), peroxyl radical (ROO.) and hypochlorous acid (HOCl), and RNS, including nitric oxide (.NO) and peroxynitrite anion (ONOO-). The obtained results revealed that the tested 2,3-diarylxanthones are endowed with outstanding ROS and RNS scavenging properties, considering the nanomolar to micromolar range of the IC50 values found. The xanthones with two catechol rings were the most potent scavengers of all tested ROS and RNS. In conclusion, the new 2,3-diarylxanthones are promising molecules to be used for their potential antioxidant properties.

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Authors+Show Affiliations

Santos CM
Departamento de Produção e Tecnologia Vegetal, Escola Superior Agrária de Bragança, 5301-855 Bragança, Portugal. clems@ipb.pt
Freitas M
No affiliation info available
Ribeiro D
No affiliation info available
Gomes A
No affiliation info available
Silva AM
No affiliation info available
Cavaleiro JA
No affiliation info available
Fernandes E
No affiliation info available

MeSH

Free Radical ScavengersHydrogen PeroxideHypochlorous AcidNitric OxidePeroxidesPeroxynitrous AcidReactive Nitrogen SpeciesReactive Oxygen SpeciesSinglet OxygenStructure-Activity RelationshipSuperoxidesXanthones

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20709556

Citation

Santos, Clementina M M., et al. "2,3-diarylxanthones as Strong Scavengers of Reactive Oxygen and Nitrogen Species: a Structure-activity Relationship Study." Bioorganic & Medicinal Chemistry, vol. 18, no. 18, 2010, pp. 6776-84.
Santos CM, Freitas M, Ribeiro D, et al. 2,3-diarylxanthones as strong scavengers of reactive oxygen and nitrogen species: a structure-activity relationship study. Bioorg Med Chem. 2010;18(18):6776-84.
Santos, C. M., Freitas, M., Ribeiro, D., Gomes, A., Silva, A. M., Cavaleiro, J. A., & Fernandes, E. (2010). 2,3-diarylxanthones as strong scavengers of reactive oxygen and nitrogen species: a structure-activity relationship study. Bioorganic & Medicinal Chemistry, 18(18), 6776-84. https://doi.org/10.1016/j.bmc.2010.07.044
Santos CM, et al. 2,3-diarylxanthones as Strong Scavengers of Reactive Oxygen and Nitrogen Species: a Structure-activity Relationship Study. Bioorg Med Chem. 2010 Sep 15;18(18):6776-84. PubMed PMID: 20709556.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 2,3-diarylxanthones as strong scavengers of reactive oxygen and nitrogen species: a structure-activity relationship study. AU - Santos,Clementina M M, AU - Freitas,Marisa, AU - Ribeiro,Daniela, AU - Gomes,Ana, AU - Silva,Artur M S, AU - Cavaleiro,José A S, AU - Fernandes,Eduarda, Y1 - 2010/07/25/ PY - 2010/06/02/received PY - 2010/07/15/revised PY - 2010/07/20/accepted PY - 2010/8/17/entrez PY - 2010/8/17/pubmed PY - 2010/12/31/medline SP - 6776 EP - 84 JF - Bioorganic & medicinal chemistry JO - Bioorg Med Chem VL - 18 IS - 18 N2 - Xanthones are a class of oxygen-containing heterocyclic compounds widely distributed in nature. The natural derivatives can present different substitutions in the xanthone core that include hydroxyl, methoxyl, prenyl and glycosyl groups. The inclusion of aryl groups has only been reported for a few synthetic derivatives, the 2,3-diaryl moiety being recently introduced by our group. Xanthones are endowed with a broad spectrum of biological activities, many of them related to their antioxidant ability, including the scavenging of reactive oxygen species (ROS) and reactive nitrogen species (RNS), as well as metal chelating effects. Considering the interesting and promising antioxidant activities present in compounds derived from the xanthone core, the main goal of this work was to evaluate the scavenging activity of the new 2,3-diarylxanthones for ROS, including superoxide radical (O2-), hydrogen peroxide (H2O2), singlet oxygen (1O2), peroxyl radical (ROO.) and hypochlorous acid (HOCl), and RNS, including nitric oxide (.NO) and peroxynitrite anion (ONOO-). The obtained results revealed that the tested 2,3-diarylxanthones are endowed with outstanding ROS and RNS scavenging properties, considering the nanomolar to micromolar range of the IC50 values found. The xanthones with two catechol rings were the most potent scavengers of all tested ROS and RNS. In conclusion, the new 2,3-diarylxanthones are promising molecules to be used for their potential antioxidant properties. SN - 1464-3391 UR - https://www.unboundmedicine.com/medline/citation/20709556/23_diarylxanthones_as_strong_scavengers_of_reactive_oxygen_and_nitrogen_species:_a_structure_activity_relationship_study_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0968-0896(10)00697-8 DB - PRIME DP - Unbound Medicine ER -