Isoflavones and Isoflavone Glycosides: Structural-Electronic Properties and Antioxidant Relations—A Case of DFT Study
Isoflavonoids and isoflavonoid glycosides have drawn much attention because of their antioxidant radical-scavenging capacity. Based on computational methods, we now present the antioxidant potential results of genistein (1), biochanin A (2), ambocin (3), and tectorigenin 7-O-[β-D-apiofuranosyl-(1-6)...
Saved in:
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Wiley
2019-01-01
|
| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2019/4360175 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1832550614996877312 |
|---|---|
| author | Son Ninh The Thanh Do Minh Trang Nguyen Van |
| author_facet | Son Ninh The Thanh Do Minh Trang Nguyen Van |
| author_sort | Son Ninh The |
| collection | DOAJ |
| description | Isoflavonoids and isoflavonoid glycosides have drawn much attention because of their antioxidant radical-scavenging capacity. Based on computational methods, we now present the antioxidant potential results of genistein (1), biochanin A (2), ambocin (3), and tectorigenin 7-O-[β-D-apiofuranosyl-(1-6)-β-D-glucopyranoside] (4). The optimized structures of the neutral and radical forms have been determined by the DFT-B3LYP method with the 6-311G(d) basis set. From the findings and thermodynamic point of view, the ring B system of isoflavones is considered as an active center in facilitating antioxidant reactions. Antioxidant activities are mostly driven by O-H bond dissociation enthalpy (BDE) following hydrogen atom transfer (HAT) mechanism. Antioxidant ability can be arranged in the following order: compounds (4) > (3) > (2) > (1). Of comprehensive structural analysis, flavonoids with 4′-methylation and 6-methoxylation, especially 7-glycosylation would claim responsibility for antioxidant enhancement. |
| format | Article |
| id | doaj-art-42aa7d503ba242749f01e436c92458f7 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2019-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-42aa7d503ba242749f01e436c92458f72025-02-03T06:06:21ZengWileyJournal of Chemistry2090-90632090-90712019-01-01201910.1155/2019/43601754360175Isoflavones and Isoflavone Glycosides: Structural-Electronic Properties and Antioxidant Relations—A Case of DFT StudySon Ninh The0Thanh Do Minh1Trang Nguyen Van2Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Caugiay, Hanoi, VietnamInstitute for Tropical Technology, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Caugiay, Hanoi, VietnamInstitute for Tropical Technology, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Caugiay, Hanoi, VietnamIsoflavonoids and isoflavonoid glycosides have drawn much attention because of their antioxidant radical-scavenging capacity. Based on computational methods, we now present the antioxidant potential results of genistein (1), biochanin A (2), ambocin (3), and tectorigenin 7-O-[β-D-apiofuranosyl-(1-6)-β-D-glucopyranoside] (4). The optimized structures of the neutral and radical forms have been determined by the DFT-B3LYP method with the 6-311G(d) basis set. From the findings and thermodynamic point of view, the ring B system of isoflavones is considered as an active center in facilitating antioxidant reactions. Antioxidant activities are mostly driven by O-H bond dissociation enthalpy (BDE) following hydrogen atom transfer (HAT) mechanism. Antioxidant ability can be arranged in the following order: compounds (4) > (3) > (2) > (1). Of comprehensive structural analysis, flavonoids with 4′-methylation and 6-methoxylation, especially 7-glycosylation would claim responsibility for antioxidant enhancement.http://dx.doi.org/10.1155/2019/4360175 |
| spellingShingle | Son Ninh The Thanh Do Minh Trang Nguyen Van Isoflavones and Isoflavone Glycosides: Structural-Electronic Properties and Antioxidant Relations—A Case of DFT Study Journal of Chemistry |
| title | Isoflavones and Isoflavone Glycosides: Structural-Electronic Properties and Antioxidant Relations—A Case of DFT Study |
| title_full | Isoflavones and Isoflavone Glycosides: Structural-Electronic Properties and Antioxidant Relations—A Case of DFT Study |
| title_fullStr | Isoflavones and Isoflavone Glycosides: Structural-Electronic Properties and Antioxidant Relations—A Case of DFT Study |
| title_full_unstemmed | Isoflavones and Isoflavone Glycosides: Structural-Electronic Properties and Antioxidant Relations—A Case of DFT Study |
| title_short | Isoflavones and Isoflavone Glycosides: Structural-Electronic Properties and Antioxidant Relations—A Case of DFT Study |
| title_sort | isoflavones and isoflavone glycosides structural electronic properties and antioxidant relations a case of dft study |
| url | http://dx.doi.org/10.1155/2019/4360175 |
| work_keys_str_mv | AT sonninhthe isoflavonesandisoflavoneglycosidesstructuralelectronicpropertiesandantioxidantrelationsacaseofdftstudy AT thanhdominh isoflavonesandisoflavoneglycosidesstructuralelectronicpropertiesandantioxidantrelationsacaseofdftstudy AT trangnguyenvan isoflavonesandisoflavoneglycosidesstructuralelectronicpropertiesandantioxidantrelationsacaseofdftstudy |