Stability and Antiproliferative Activity of Malvidin-Based Non-Oxonium Derivative (Oxovitisin A) Compared with Precursor Anthocyanins and Pyranoanthocyanins
Oxovitisins are a unique group of anthocyanin derivatives with a non-oxonium nature and α-pyranone (lactone) D ring on the structure. In this study, oxovitisin A was synthesized through the micro-oxidative reaction of carboxypyranomalvidin-3-O-glucoside (vitisin A) with water, and its thermostabilit...
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MDPI AG
2022-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/15/5030 |
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| author | Muci Wu Yan Ma Ao Li Jingyi Wang Jingren He Rui Zhang |
| author_facet | Muci Wu Yan Ma Ao Li Jingyi Wang Jingren He Rui Zhang |
| author_sort | Muci Wu |
| collection | DOAJ |
| description | Oxovitisins are a unique group of anthocyanin derivatives with a non-oxonium nature and α-pyranone (lactone) D ring on the structure. In this study, oxovitisin A was synthesized through the micro-oxidative reaction of carboxypyranomalvidin-3-O-glucoside (vitisin A) with water, and its thermostability, pH, and SO<sub>2</sub> color stability were studied compared with its two precursors, malvidin-3-O-glucoside (Mv3glc) and vitisin A, as well as methylpyrano-malvidin-3-O-glucoside (Me-py). Results showed that oxovitisin A exhibited the highest stabilities, which were inseparably related to its noncharged structure and the additional carbonyl group on the D ring. Moreover, the antiproliferative capacity of oxovitisin A was comparatively evaluated against two human gastrointestinal cancer cell lines. Interestingly, oxovitisin A presented the strongest antiproliferative ability on MKN-28 (IC<sub>50</sub> = 538.42 ± 50.06 μM) and Caco-2 cells (IC<sub>50</sub> = 434.85 ± 11.87 μM) compared with two other pyranoanthocyanins. Therefore, we conclude that oxovitisin A as a highly stable anthocyanin derivative still exhibits a satisfactory antiproliferative ability. |
| first_indexed | 2024-03-09T10:06:15Z |
| format | Article |
| id | doaj.art-207f339cdde64178b775e3b975087c04 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T10:06:15Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-207f339cdde64178b775e3b975087c042023-12-01T23:03:58ZengMDPI AGMolecules1420-30492022-08-012715503010.3390/molecules27155030Stability and Antiproliferative Activity of Malvidin-Based Non-Oxonium Derivative (Oxovitisin A) Compared with Precursor Anthocyanins and PyranoanthocyaninsMuci Wu0Yan Ma1Ao Li2Jingyi Wang3Jingren He4Rui Zhang5National R&D Center for Se-Rich Agricultural Products Processing, School of Modern Industry for Selenium Science and Engineering, Wuhan Polytechnic University, Wuhan 430048, ChinaNational R&D Center for Se-Rich Agricultural Products Processing, School of Modern Industry for Selenium Science and Engineering, Wuhan Polytechnic University, Wuhan 430048, ChinaHubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, ChinaSchool of Food and Biological Engineering, Hubei University of Technology, Wuhan 430068, ChinaNational R&D Center for Se-Rich Agricultural Products Processing, School of Modern Industry for Selenium Science and Engineering, Wuhan Polytechnic University, Wuhan 430048, ChinaNational R&D Center for Se-Rich Agricultural Products Processing, School of Modern Industry for Selenium Science and Engineering, Wuhan Polytechnic University, Wuhan 430048, ChinaOxovitisins are a unique group of anthocyanin derivatives with a non-oxonium nature and α-pyranone (lactone) D ring on the structure. In this study, oxovitisin A was synthesized through the micro-oxidative reaction of carboxypyranomalvidin-3-O-glucoside (vitisin A) with water, and its thermostability, pH, and SO<sub>2</sub> color stability were studied compared with its two precursors, malvidin-3-O-glucoside (Mv3glc) and vitisin A, as well as methylpyrano-malvidin-3-O-glucoside (Me-py). Results showed that oxovitisin A exhibited the highest stabilities, which were inseparably related to its noncharged structure and the additional carbonyl group on the D ring. Moreover, the antiproliferative capacity of oxovitisin A was comparatively evaluated against two human gastrointestinal cancer cell lines. Interestingly, oxovitisin A presented the strongest antiproliferative ability on MKN-28 (IC<sub>50</sub> = 538.42 ± 50.06 μM) and Caco-2 cells (IC<sub>50</sub> = 434.85 ± 11.87 μM) compared with two other pyranoanthocyanins. Therefore, we conclude that oxovitisin A as a highly stable anthocyanin derivative still exhibits a satisfactory antiproliferative ability.https://www.mdpi.com/1420-3049/27/15/5030oxovitisin Apyranoanthocyaninstabilityantiproliferative |
| spellingShingle | Muci Wu Yan Ma Ao Li Jingyi Wang Jingren He Rui Zhang Stability and Antiproliferative Activity of Malvidin-Based Non-Oxonium Derivative (Oxovitisin A) Compared with Precursor Anthocyanins and Pyranoanthocyanins Molecules oxovitisin A pyranoanthocyanin stability antiproliferative |
| title | Stability and Antiproliferative Activity of Malvidin-Based Non-Oxonium Derivative (Oxovitisin A) Compared with Precursor Anthocyanins and Pyranoanthocyanins |
| title_full | Stability and Antiproliferative Activity of Malvidin-Based Non-Oxonium Derivative (Oxovitisin A) Compared with Precursor Anthocyanins and Pyranoanthocyanins |
| title_fullStr | Stability and Antiproliferative Activity of Malvidin-Based Non-Oxonium Derivative (Oxovitisin A) Compared with Precursor Anthocyanins and Pyranoanthocyanins |
| title_full_unstemmed | Stability and Antiproliferative Activity of Malvidin-Based Non-Oxonium Derivative (Oxovitisin A) Compared with Precursor Anthocyanins and Pyranoanthocyanins |
| title_short | Stability and Antiproliferative Activity of Malvidin-Based Non-Oxonium Derivative (Oxovitisin A) Compared with Precursor Anthocyanins and Pyranoanthocyanins |
| title_sort | stability and antiproliferative activity of malvidin based non oxonium derivative oxovitisin a compared with precursor anthocyanins and pyranoanthocyanins |
| topic | oxovitisin A pyranoanthocyanin stability antiproliferative |
| url | https://www.mdpi.com/1420-3049/27/15/5030 |
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