Structure and Antioxidant Activity Relationships of Isoflavonoids from Dalbergia parviflora

Structure and Antioxidant Activity Relationships of Isoflavonoids from Dalbergia parviflora

Worrawat Promden, Orawan Monthakantirat, Kaoru Umehara, Hiroshi Noguchi, Wanchai De-Eknamkul

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.

2014

Antioxidant, Isoflavonoids, Dalbergia parviflora, DPPH, ORAC, xanthine/xanthine oxidase assay, structure-activity relationship

DOI: 10.3390/molecules19022226

Molecules

MDPI AG

Organic chemistry

EN