Synthesis of Caffeoyl-Prolyl-Histidyl-Xaa Derivatives and Evaluation of Their Activities and Stability upon Long-Term Storage
Antioxidants play a critical role in the treatment of degenerative diseases and delaying the aging of dermal tissue. Caffeic acid (CA) is a representative example of the antioxidants found in plants. However, CA is unsuitable for long-term storage because of its poor stability under ambient conditio...
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MDPI AG
2021-06-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/22/12/6301 |
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doaj-ac5538c869064c4c98eaf1e95ece1e9f2021-06-30T23:59:31ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-06-01226301630110.3390/ijms22126301Synthesis of Caffeoyl-Prolyl-Histidyl-Xaa Derivatives and Evaluation of Their Activities and Stability upon Long-Term StorageHyeri Jeong0Young-Eun Jeon1Jin-Kyoung Yang2Jaehi Kim3Woo-Jae Chung4Yoon-Sik Lee5Dong-Sik Shin6Department of Chemical and Biological Engineering, Sookmyung Women’s University, Seoul 04310, KoreaDepartment of Chemical and Biological Engineering, Sookmyung Women’s University, Seoul 04310, KoreaSchool of Chemical and Biological Engineering, Seoul National University, Seoul 08826, KoreaSchool of Chemical and Biological Engineering, Seoul National University, Seoul 08826, KoreaDepartment of Integrative Biotechnology, Sungkyunkwan University, Suwon 16419, KoreaSchool of Chemical and Biological Engineering, Seoul National University, Seoul 08826, KoreaDepartment of Chemical and Biological Engineering, Sookmyung Women’s University, Seoul 04310, KoreaAntioxidants play a critical role in the treatment of degenerative diseases and delaying the aging of dermal tissue. Caffeic acid (CA) is a representative example of the antioxidants found in plants. However, CA is unsuitable for long-term storage because of its poor stability under ambient conditions. Caffeoyl-Pro-His-NH<sub>2</sub> (CA-Pro-His-NH<sub>2</sub>, CA-PH) exhibits the highest antioxidant activity, free radical scavenging and lipid peroxidation inhibition activity among the histidine-containing CA-conjugated dipeptides reported to date. The addition of short peptides to CA, such as Pro-His, is assumed to synergistically enhance its antioxidative activity. In this study, several caffeoyl-prolyl-histidyl-Xaa-NH<sub>2</sub> derivatives were synthesized and their antioxidative activities evaluated. CA-Pro-His-Asn-NH<sub>2</sub> showed enhanced antioxidative activity and higher structural stability than CA-PH, even after long-term storage. CA-Pro-His-Asn-NH<sub>2</sub> was stable for 3 months, its stability being evaluated by observing the changes in its NMR spectra. Moreover, the solid-phase synthetic strategy used to prepare these CA-Pro-His-Xaa-NH<sub>2</sub> derivatives was optimized for large-scale production. We envision that CA-Pro-His-Xaa-NH<sub>2</sub> derivatives can be used as potent dermal therapeutic agents and useful cosmetic ingredients.https://www.mdpi.com/1422-0067/22/12/6301solid-phase synthesiscaffeic acidcaffeoyl peptide derivativesantioxidantstability |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Hyeri Jeong Young-Eun Jeon Jin-Kyoung Yang Jaehi Kim Woo-Jae Chung Yoon-Sik Lee Dong-Sik Shin |
| spellingShingle |
Hyeri Jeong Young-Eun Jeon Jin-Kyoung Yang Jaehi Kim Woo-Jae Chung Yoon-Sik Lee Dong-Sik Shin Synthesis of Caffeoyl-Prolyl-Histidyl-Xaa Derivatives and Evaluation of Their Activities and Stability upon Long-Term Storage International Journal of Molecular Sciences solid-phase synthesis caffeic acid caffeoyl peptide derivatives antioxidant stability |
| author_facet |
Hyeri Jeong Young-Eun Jeon Jin-Kyoung Yang Jaehi Kim Woo-Jae Chung Yoon-Sik Lee Dong-Sik Shin |
| author_sort |
Hyeri Jeong |
| title |
Synthesis of Caffeoyl-Prolyl-Histidyl-Xaa Derivatives and Evaluation of Their Activities and Stability upon Long-Term Storage |
| title_short |
Synthesis of Caffeoyl-Prolyl-Histidyl-Xaa Derivatives and Evaluation of Their Activities and Stability upon Long-Term Storage |
| title_full |
Synthesis of Caffeoyl-Prolyl-Histidyl-Xaa Derivatives and Evaluation of Their Activities and Stability upon Long-Term Storage |
| title_fullStr |
Synthesis of Caffeoyl-Prolyl-Histidyl-Xaa Derivatives and Evaluation of Their Activities and Stability upon Long-Term Storage |
| title_full_unstemmed |
Synthesis of Caffeoyl-Prolyl-Histidyl-Xaa Derivatives and Evaluation of Their Activities and Stability upon Long-Term Storage |
| title_sort |
synthesis of caffeoyl-prolyl-histidyl-xaa derivatives and evaluation of their activities and stability upon long-term storage |
| publisher |
MDPI AG |
| series |
International Journal of Molecular Sciences |
| issn |
1661-6596 1422-0067 |
| publishDate |
2021-06-01 |
| description |
Antioxidants play a critical role in the treatment of degenerative diseases and delaying the aging of dermal tissue. Caffeic acid (CA) is a representative example of the antioxidants found in plants. However, CA is unsuitable for long-term storage because of its poor stability under ambient conditions. Caffeoyl-Pro-His-NH<sub>2</sub> (CA-Pro-His-NH<sub>2</sub>, CA-PH) exhibits the highest antioxidant activity, free radical scavenging and lipid peroxidation inhibition activity among the histidine-containing CA-conjugated dipeptides reported to date. The addition of short peptides to CA, such as Pro-His, is assumed to synergistically enhance its antioxidative activity. In this study, several caffeoyl-prolyl-histidyl-Xaa-NH<sub>2</sub> derivatives were synthesized and their antioxidative activities evaluated. CA-Pro-His-Asn-NH<sub>2</sub> showed enhanced antioxidative activity and higher structural stability than CA-PH, even after long-term storage. CA-Pro-His-Asn-NH<sub>2</sub> was stable for 3 months, its stability being evaluated by observing the changes in its NMR spectra. Moreover, the solid-phase synthetic strategy used to prepare these CA-Pro-His-Xaa-NH<sub>2</sub> derivatives was optimized for large-scale production. We envision that CA-Pro-His-Xaa-NH<sub>2</sub> derivatives can be used as potent dermal therapeutic agents and useful cosmetic ingredients. |
| topic |
solid-phase synthesis caffeic acid caffeoyl peptide derivatives antioxidant stability |
| url |
https://www.mdpi.com/1422-0067/22/12/6301 |
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