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Structure and Antioxidant Activity Relationships of Isoflavonoids from Dalbergia parviflora

The antioxidant activities of 24 isoflavonoids that were previously isolated as pure compounds from Dalbergia parviflora were evaluated using three different in vitro antioxidant-based assay systems: xanthine/xanthine oxidase (X/XO), ORAC, and DPPH. The isolates consisted of three subgroups, namely...

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Autores principales: Promden, Worrawat, Monthakantirat, Orawan, Umehara, Kaoru, Noguchi, Hiroshi, De-Eknamkul, Wanchai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271601/
https://www.ncbi.nlm.nih.gov/pubmed/24561331
http://dx.doi.org/10.3390/molecules19022226
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author Promden, Worrawat
Monthakantirat, Orawan
Umehara, Kaoru
Noguchi, Hiroshi
De-Eknamkul, Wanchai
author_facet Promden, Worrawat
Monthakantirat, Orawan
Umehara, Kaoru
Noguchi, Hiroshi
De-Eknamkul, Wanchai
author_sort Promden, Worrawat
collection PubMed
description The antioxidant activities of 24 isoflavonoids that were previously isolated as pure compounds from Dalbergia parviflora were evaluated using three different in vitro antioxidant-based assay systems: xanthine/xanthine oxidase (X/XO), ORAC, and DPPH. The isolates consisted of three subgroups, namely isoflavones, isoflavanones, and isoflavans, each of which appeared to have diversified substituents, and were thus ideal for the study of their structure-activity relationships (SARs). The SAR analysis was performed using the results obtained from both the inter-subgroup isoflavonoids with the same substitution pattern and the intra-subgroup compounds with different substitution patterns. The inter-subgroup comparison showed that the isoflavones exhibited the highest antioxidant activities based on all three assays. The intra-subgroup analysis showed that the additional presence of an OH group in Ring B at either R3′ or R5′ from the basic common structure of the R7-OH of Ring A and the R4′-OH (or -OMe) of Ring B greatly increased the antioxidant activities of all of the isoflavonoid subgroups and that other positions of OH and OMe substitutions exerted different effects on the activities depending on the subgroup and assay type. Therefore, based on the structural diversity of the isoflavonoids in D. parviflora, the present study provides the first clarification of the detailed antioxidant SARs of isoflavonoids.
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spelling pubmed-62716012018-12-20 Structure and Antioxidant Activity Relationships of Isoflavonoids from Dalbergia parviflora Promden, Worrawat Monthakantirat, Orawan Umehara, Kaoru Noguchi, Hiroshi De-Eknamkul, Wanchai Molecules Article The antioxidant activities of 24 isoflavonoids that were previously isolated as pure compounds from Dalbergia parviflora were evaluated using three different in vitro antioxidant-based assay systems: xanthine/xanthine oxidase (X/XO), ORAC, and DPPH. The isolates consisted of three subgroups, namely isoflavones, isoflavanones, and isoflavans, each of which appeared to have diversified substituents, and were thus ideal for the study of their structure-activity relationships (SARs). The SAR analysis was performed using the results obtained from both the inter-subgroup isoflavonoids with the same substitution pattern and the intra-subgroup compounds with different substitution patterns. The inter-subgroup comparison showed that the isoflavones exhibited the highest antioxidant activities based on all three assays. The intra-subgroup analysis showed that the additional presence of an OH group in Ring B at either R3′ or R5′ from the basic common structure of the R7-OH of Ring A and the R4′-OH (or -OMe) of Ring B greatly increased the antioxidant activities of all of the isoflavonoid subgroups and that other positions of OH and OMe substitutions exerted different effects on the activities depending on the subgroup and assay type. Therefore, based on the structural diversity of the isoflavonoids in D. parviflora, the present study provides the first clarification of the detailed antioxidant SARs of isoflavonoids. MDPI 2014-02-20 /pmc/articles/PMC6271601/ /pubmed/24561331 http://dx.doi.org/10.3390/molecules19022226 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Promden, Worrawat
Monthakantirat, Orawan
Umehara, Kaoru
Noguchi, Hiroshi
De-Eknamkul, Wanchai
Structure and Antioxidant Activity Relationships of Isoflavonoids from Dalbergia parviflora
title Structure and Antioxidant Activity Relationships of Isoflavonoids from Dalbergia parviflora
title_full Structure and Antioxidant Activity Relationships of Isoflavonoids from Dalbergia parviflora
title_fullStr Structure and Antioxidant Activity Relationships of Isoflavonoids from Dalbergia parviflora
title_full_unstemmed Structure and Antioxidant Activity Relationships of Isoflavonoids from Dalbergia parviflora
title_short Structure and Antioxidant Activity Relationships of Isoflavonoids from Dalbergia parviflora
title_sort structure and antioxidant activity relationships of isoflavonoids from dalbergia parviflora
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271601/
https://www.ncbi.nlm.nih.gov/pubmed/24561331
http://dx.doi.org/10.3390/molecules19022226
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