Ratiometric Fluorescent Probes Based on Isosteviol with Identification of Maleic Acid in Starchy Foods

The rigid saddle-shaped framework of isosteviol provides a unique host–guest recognition cavity. For the first time, we have utilized isosteviol to construct fluorescent probes 4 and 5, achieving highly selective recognition of maleic acid and fumaric acid. The experimental results indicated that ne...

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Main Authors: Xinye Qian, Chunling Zheng, Fang Zhang
Format: Article
Language:English
Published: MDPI AG 2025-04-01
Series:Foods
Subjects:
Online Access:https://www.mdpi.com/2304-8158/14/9/1541
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author Xinye Qian
Chunling Zheng
Fang Zhang
author_facet Xinye Qian
Chunling Zheng
Fang Zhang
author_sort Xinye Qian
collection DOAJ
description The rigid saddle-shaped framework of isosteviol provides a unique host–guest recognition cavity. For the first time, we have utilized isosteviol to construct fluorescent probes 4 and 5, achieving highly selective recognition of maleic acid and fumaric acid. The experimental results indicated that neither probe 4 nor probe 5 exhibited significant fluorescence changes when exposed to fumaric acid. However, both probes demonstrated distinct ratiometric fluorescence responses upon interaction with maleic acid. For maleic acid, probes 4 and 5 showed detection limits of 4.14 × 10<sup>−6</sup> M and 1.88 × 10<sup>−6</sup> M, respectively. Density functional theory (DFT) calculations and <sup>1</sup>H NMR spectroscopy revealed that probes 4 and 5 formed stable intermolecular hydrogen bonds with maleic acid, contributing to the observed changes in fluorescence signals. Furthermore, maleic acid was successfully detected in starch-rich dietary samples, including potatoes, sweet potatoes, and corn, utilizing the sensing capabilities of probes 4 and 5. In conclusion, probes 4 and 5 hold significant potential for the development of fluorescence-based recognition systems for fumaric acid and maleic acid.
format Article
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institution OA Journals
issn 2304-8158
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publishDate 2025-04-01
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spelling doaj-art-4c9518438bef45599fa65dd2b31556972025-08-20T01:49:18ZengMDPI AGFoods2304-81582025-04-01149154110.3390/foods14091541Ratiometric Fluorescent Probes Based on Isosteviol with Identification of Maleic Acid in Starchy FoodsXinye Qian0Chunling Zheng1Fang Zhang2College of Food Science and Light Industry, Nanjing Tech University, Nanjing 211800, ChinaCollege of Food Science and Light Industry, Nanjing Tech University, Nanjing 211800, ChinaCollege of Food Science and Light Industry, Nanjing Tech University, Nanjing 211800, ChinaThe rigid saddle-shaped framework of isosteviol provides a unique host–guest recognition cavity. For the first time, we have utilized isosteviol to construct fluorescent probes 4 and 5, achieving highly selective recognition of maleic acid and fumaric acid. The experimental results indicated that neither probe 4 nor probe 5 exhibited significant fluorescence changes when exposed to fumaric acid. However, both probes demonstrated distinct ratiometric fluorescence responses upon interaction with maleic acid. For maleic acid, probes 4 and 5 showed detection limits of 4.14 × 10<sup>−6</sup> M and 1.88 × 10<sup>−6</sup> M, respectively. Density functional theory (DFT) calculations and <sup>1</sup>H NMR spectroscopy revealed that probes 4 and 5 formed stable intermolecular hydrogen bonds with maleic acid, contributing to the observed changes in fluorescence signals. Furthermore, maleic acid was successfully detected in starch-rich dietary samples, including potatoes, sweet potatoes, and corn, utilizing the sensing capabilities of probes 4 and 5. In conclusion, probes 4 and 5 hold significant potential for the development of fluorescence-based recognition systems for fumaric acid and maleic acid.https://www.mdpi.com/2304-8158/14/9/1541fluorescencemaleic acidfumaric acidisosteviol
spellingShingle Xinye Qian
Chunling Zheng
Fang Zhang
Ratiometric Fluorescent Probes Based on Isosteviol with Identification of Maleic Acid in Starchy Foods
Foods
fluorescence
maleic acid
fumaric acid
isosteviol
title Ratiometric Fluorescent Probes Based on Isosteviol with Identification of Maleic Acid in Starchy Foods
title_full Ratiometric Fluorescent Probes Based on Isosteviol with Identification of Maleic Acid in Starchy Foods
title_fullStr Ratiometric Fluorescent Probes Based on Isosteviol with Identification of Maleic Acid in Starchy Foods
title_full_unstemmed Ratiometric Fluorescent Probes Based on Isosteviol with Identification of Maleic Acid in Starchy Foods
title_short Ratiometric Fluorescent Probes Based on Isosteviol with Identification of Maleic Acid in Starchy Foods
title_sort ratiometric fluorescent probes based on isosteviol with identification of maleic acid in starchy foods
topic fluorescence
maleic acid
fumaric acid
isosteviol
url https://www.mdpi.com/2304-8158/14/9/1541
work_keys_str_mv AT xinyeqian ratiometricfluorescentprobesbasedonisosteviolwithidentificationofmaleicacidinstarchyfoods
AT chunlingzheng ratiometricfluorescentprobesbasedonisosteviolwithidentificationofmaleicacidinstarchyfoods
AT fangzhang ratiometricfluorescentprobesbasedonisosteviolwithidentificationofmaleicacidinstarchyfoods