The antityrosinase and antioxidant activities of flavonoids dominated by the number and location of phenolic hydroxyl groups
Abstract Background Compounds with the ability to scavenge reactive oxygen species (ROS) and inhibit tyrosinase may be useful for the treatment and prevention from ROS-related diseases. The number and location of phenolic hydroxyl of the flavonoids will significantly influence the inhibition of tyro...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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BMC
2018-10-01
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| Series: | Chinese Medicine |
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| Online Access: | http://link.springer.com/article/10.1186/s13020-018-0206-9 |
| _version_ | 1828496016944398336 |
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| author | Ai-Ren Zuo Huan-Huan Dong Yan-Ying Yu Qing-Long Shu Li-Xiang Zheng Xiong-Ying Yu Shu-Wen Cao |
| author_facet | Ai-Ren Zuo Huan-Huan Dong Yan-Ying Yu Qing-Long Shu Li-Xiang Zheng Xiong-Ying Yu Shu-Wen Cao |
| author_sort | Ai-Ren Zuo |
| collection | DOAJ |
| description | Abstract Background Compounds with the ability to scavenge reactive oxygen species (ROS) and inhibit tyrosinase may be useful for the treatment and prevention from ROS-related diseases. The number and location of phenolic hydroxyl of the flavonoids will significantly influence the inhibition of tyrosinase activity. Phenolic hydroxyl is indispensable to the antioxidant activity of flavonoids. Isoeugenol, shikonin, baicalein, rosmarinic acid, and dihydromyricetin have respectively one, two, three, four, or five phenolic hydroxyls. The different molecular structures with the similar structure to l-3,4-dihydroxyphenylalanine (l-DOPA) were expected to the different antityrosinase and antioxidant activities. Methods This investigation tested the antityrosinase activity, the inhibition constant, and inhibition type of isoeugenol, shikonin, baicalein, rosmarinic acid, and dihydromyricetin. Molecular docking was examined by the Discovery Studio 2.5 (CDOCKER Dock, Dassault Systemes BIOVIA, USA). This experiment also examined the antioxidant effects of the five compounds on supercoiled pBR322 plasmid DNA, lipid peroxidation in rat liver mitochondria in vitro, and DPPH, ABTS, hydroxyl, or superoxide free radical scavenging activity in vitro. Results The compounds exhibited good antityrosinase activities. Molecular docking results implied that the compounds could interact with the amino acid residues in the active site center of antityrosinase. These compounds also exhibited antioxidant effects on DPPH, ABTS, hydroxyl, or superoxide free radical scavenging activity in vitro, lipid peroxidation in rat liver mitochondria induced by Fe2+/vitamin C system in vitro, and supercoiled pBR322 plasmid DNA. The activity order is isoeugenol < shikonin < baicalein < rosmarinic acid < dihydromyricetin. The results showed the compounds with more phenolic hydroxyls have more antioxidant and antityrosinase activities. Conclusion This was the first study of molecular docking for modeling the antityrosinase activity of compounds. This was also the first study of the protective effects of compounds on supercoiled pBR322 plasmid DNA, the lipid peroxidation inhibition activity in liver mitochondria. These results suggest that the compounds exhibited antityrosinase and antioxidant activities may be useful in skin pigmentation and food additives. |
| first_indexed | 2024-12-11T12:22:31Z |
| format | Article |
| id | doaj.art-8086efcdcf154aac815f80c6b1000144 |
| institution | Directory Open Access Journal |
| issn | 1749-8546 |
| language | English |
| last_indexed | 2024-12-11T12:22:31Z |
| publishDate | 2018-10-01 |
| publisher | BMC |
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| series | Chinese Medicine |
| spelling | doaj.art-8086efcdcf154aac815f80c6b10001442022-12-22T01:07:30ZengBMCChinese Medicine1749-85462018-10-0113111210.1186/s13020-018-0206-9The antityrosinase and antioxidant activities of flavonoids dominated by the number and location of phenolic hydroxyl groupsAi-Ren Zuo0Huan-Huan Dong1Yan-Ying Yu2Qing-Long Shu3Li-Xiang Zheng4Xiong-Ying Yu5Shu-Wen Cao6State Key Laboratory of Food Science and Technology, Nanchang UniversityJiangxi University of Traditional Chinese MedicineDepartment of Chemistry, Nanchang UniversityJiangxi University of Traditional Chinese MedicineJiangxi University of Traditional Chinese MedicineJiangxi University of Traditional Chinese MedicineState Key Laboratory of Food Science and Technology, Nanchang UniversityAbstract Background Compounds with the ability to scavenge reactive oxygen species (ROS) and inhibit tyrosinase may be useful for the treatment and prevention from ROS-related diseases. The number and location of phenolic hydroxyl of the flavonoids will significantly influence the inhibition of tyrosinase activity. Phenolic hydroxyl is indispensable to the antioxidant activity of flavonoids. Isoeugenol, shikonin, baicalein, rosmarinic acid, and dihydromyricetin have respectively one, two, three, four, or five phenolic hydroxyls. The different molecular structures with the similar structure to l-3,4-dihydroxyphenylalanine (l-DOPA) were expected to the different antityrosinase and antioxidant activities. Methods This investigation tested the antityrosinase activity, the inhibition constant, and inhibition type of isoeugenol, shikonin, baicalein, rosmarinic acid, and dihydromyricetin. Molecular docking was examined by the Discovery Studio 2.5 (CDOCKER Dock, Dassault Systemes BIOVIA, USA). This experiment also examined the antioxidant effects of the five compounds on supercoiled pBR322 plasmid DNA, lipid peroxidation in rat liver mitochondria in vitro, and DPPH, ABTS, hydroxyl, or superoxide free radical scavenging activity in vitro. Results The compounds exhibited good antityrosinase activities. Molecular docking results implied that the compounds could interact with the amino acid residues in the active site center of antityrosinase. These compounds also exhibited antioxidant effects on DPPH, ABTS, hydroxyl, or superoxide free radical scavenging activity in vitro, lipid peroxidation in rat liver mitochondria induced by Fe2+/vitamin C system in vitro, and supercoiled pBR322 plasmid DNA. The activity order is isoeugenol < shikonin < baicalein < rosmarinic acid < dihydromyricetin. The results showed the compounds with more phenolic hydroxyls have more antioxidant and antityrosinase activities. Conclusion This was the first study of molecular docking for modeling the antityrosinase activity of compounds. This was also the first study of the protective effects of compounds on supercoiled pBR322 plasmid DNA, the lipid peroxidation inhibition activity in liver mitochondria. These results suggest that the compounds exhibited antityrosinase and antioxidant activities may be useful in skin pigmentation and food additives.http://link.springer.com/article/10.1186/s13020-018-0206-9Antityrosinase activityMolecular dockingAntioxidant activityPhenolic hydroxylIsoeugenolShikonin |
| spellingShingle | Ai-Ren Zuo Huan-Huan Dong Yan-Ying Yu Qing-Long Shu Li-Xiang Zheng Xiong-Ying Yu Shu-Wen Cao The antityrosinase and antioxidant activities of flavonoids dominated by the number and location of phenolic hydroxyl groups Chinese Medicine Antityrosinase activity Molecular docking Antioxidant activity Phenolic hydroxyl Isoeugenol Shikonin |
| title | The antityrosinase and antioxidant activities of flavonoids dominated by the number and location of phenolic hydroxyl groups |
| title_full | The antityrosinase and antioxidant activities of flavonoids dominated by the number and location of phenolic hydroxyl groups |
| title_fullStr | The antityrosinase and antioxidant activities of flavonoids dominated by the number and location of phenolic hydroxyl groups |
| title_full_unstemmed | The antityrosinase and antioxidant activities of flavonoids dominated by the number and location of phenolic hydroxyl groups |
| title_short | The antityrosinase and antioxidant activities of flavonoids dominated by the number and location of phenolic hydroxyl groups |
| title_sort | antityrosinase and antioxidant activities of flavonoids dominated by the number and location of phenolic hydroxyl groups |
| topic | Antityrosinase activity Molecular docking Antioxidant activity Phenolic hydroxyl Isoeugenol Shikonin |
| url | http://link.springer.com/article/10.1186/s13020-018-0206-9 |
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