Transmembrane behaviors and quantitative structure–activity relationship of dietary flavonoids in the presence of intestinal digestive products from different carbohydrate sources based on in vitro and in silico analysis
Bioavailability plays a key role for flavonoids to exert their bioactivities. This study investigated the transmembrane transport behavior and structure–activity of dietary flavonoids. Results showed that the apparent permeability coefficients of some flavonoids could be significantly increased when...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2023-12-01
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| Series: | Food Chemistry: X |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2590157523004376 |
| _version_ | 1797383665175494656 |
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| author | Xiaojing Liu Shuang Ma Yuanyue Zhang Yishan Fu Shengbao Cai |
| author_facet | Xiaojing Liu Shuang Ma Yuanyue Zhang Yishan Fu Shengbao Cai |
| author_sort | Xiaojing Liu |
| collection | DOAJ |
| description | Bioavailability plays a key role for flavonoids to exert their bioactivities. This study investigated the transmembrane transport behavior and structure–activity of dietary flavonoids. Results showed that the apparent permeability coefficients of some flavonoids could be significantly increased when digestion products from rice flour (RD) or wheat flour (WD) are present (p < 0.05), especially in the WD, potentially due to higher reducing sugar (p < 0.05). 3D-QSAR revealed that the hydrogen bond acceptor groups at positions 5 and 6 of ring A, small-volume groups at position 3′, hydrophobic groups at position 4′, and large-volume groups at position 5′ of ring B increased the transmembrane transport of flavonoids in the WD. A hydrogen bond donor group at position 4′ of ring B enhanced the transmembrane transport of flavonoid compounds in the RD. These findings contribute to our comprehensive understanding of flavonoid absorption within the context of intestinal carbohydrate digestion. |
| first_indexed | 2024-03-08T21:25:15Z |
| format | Article |
| id | doaj.art-7c29f01d460c4f20a7e3020a5ee6cb00 |
| institution | Directory Open Access Journal |
| issn | 2590-1575 |
| language | English |
| last_indexed | 2024-03-08T21:25:15Z |
| publishDate | 2023-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Food Chemistry: X |
| spelling | doaj.art-7c29f01d460c4f20a7e3020a5ee6cb002023-12-21T07:36:53ZengElsevierFood Chemistry: X2590-15752023-12-0120100994Transmembrane behaviors and quantitative structure–activity relationship of dietary flavonoids in the presence of intestinal digestive products from different carbohydrate sources based on in vitro and in silico analysisXiaojing Liu0Shuang Ma1Yuanyue Zhang2Yishan Fu3Shengbao Cai4Faculty of Food Science and Engineering, Kunming University of Science and Technology, Kunming, Yunnan Province 650500, People’s Republic of China; School of Food Science and Technology, Jiangnan University, Wuxi, Jiangsu Province 214122, People’s Republic of ChinaFaculty of Food Science and Engineering, Kunming University of Science and Technology, Kunming, Yunnan Province 650500, People’s Republic of ChinaFaculty of Food Science and Engineering, Kunming University of Science and Technology, Kunming, Yunnan Province 650500, People’s Republic of ChinaFaculty of Food Science and Engineering, Kunming University of Science and Technology, Kunming, Yunnan Province 650500, People’s Republic of China; Science Center for Future Foods, Jiangnan University, Wuxi, Jiangsu Province 214122, People’s Republic of China; Corresponding authors at: Faculty of Food Science and Engineering, Kunming University of Science and Technology, Kunming, Yunnan Province 650500, People’s Republic of China (Y. Fu, and S. Cai).Faculty of Food Science and Engineering, Kunming University of Science and Technology, Kunming, Yunnan Province 650500, People’s Republic of China; Corresponding authors at: Faculty of Food Science and Engineering, Kunming University of Science and Technology, Kunming, Yunnan Province 650500, People’s Republic of China (Y. Fu, and S. Cai).Bioavailability plays a key role for flavonoids to exert their bioactivities. This study investigated the transmembrane transport behavior and structure–activity of dietary flavonoids. Results showed that the apparent permeability coefficients of some flavonoids could be significantly increased when digestion products from rice flour (RD) or wheat flour (WD) are present (p < 0.05), especially in the WD, potentially due to higher reducing sugar (p < 0.05). 3D-QSAR revealed that the hydrogen bond acceptor groups at positions 5 and 6 of ring A, small-volume groups at position 3′, hydrophobic groups at position 4′, and large-volume groups at position 5′ of ring B increased the transmembrane transport of flavonoids in the WD. A hydrogen bond donor group at position 4′ of ring B enhanced the transmembrane transport of flavonoid compounds in the RD. These findings contribute to our comprehensive understanding of flavonoid absorption within the context of intestinal carbohydrate digestion.http://www.sciencedirect.com/science/article/pii/S2590157523004376BioavailabilityDietary flavonoidsWheat flourRice flourIn vitro simulated digestion3D-QSAR |
| spellingShingle | Xiaojing Liu Shuang Ma Yuanyue Zhang Yishan Fu Shengbao Cai Transmembrane behaviors and quantitative structure–activity relationship of dietary flavonoids in the presence of intestinal digestive products from different carbohydrate sources based on in vitro and in silico analysis Food Chemistry: X Bioavailability Dietary flavonoids Wheat flour Rice flour In vitro simulated digestion 3D-QSAR |
| title | Transmembrane behaviors and quantitative structure–activity relationship of dietary flavonoids in the presence of intestinal digestive products from different carbohydrate sources based on in vitro and in silico analysis |
| title_full | Transmembrane behaviors and quantitative structure–activity relationship of dietary flavonoids in the presence of intestinal digestive products from different carbohydrate sources based on in vitro and in silico analysis |
| title_fullStr | Transmembrane behaviors and quantitative structure–activity relationship of dietary flavonoids in the presence of intestinal digestive products from different carbohydrate sources based on in vitro and in silico analysis |
| title_full_unstemmed | Transmembrane behaviors and quantitative structure–activity relationship of dietary flavonoids in the presence of intestinal digestive products from different carbohydrate sources based on in vitro and in silico analysis |
| title_short | Transmembrane behaviors and quantitative structure–activity relationship of dietary flavonoids in the presence of intestinal digestive products from different carbohydrate sources based on in vitro and in silico analysis |
| title_sort | transmembrane behaviors and quantitative structure activity relationship of dietary flavonoids in the presence of intestinal digestive products from different carbohydrate sources based on in vitro and in silico analysis |
| topic | Bioavailability Dietary flavonoids Wheat flour Rice flour In vitro simulated digestion 3D-QSAR |
| url | http://www.sciencedirect.com/science/article/pii/S2590157523004376 |
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