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Updated: Nov 14, 2025
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Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade
Published on: August 14, 2019
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Competitive cocrystallization and its application in the separation of flavonoids
Yanming Xia1, Yuanfeng Wei1, Hui Chen2
1School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 211198, People's Republic of China.
Iucrj
|March 12, 2021
Summary
Cocrystallization using caffeine effectively separates similar natural flavonoids like myricetin, quercetin, and baicalein. This green chemistry approach achieves high purity and offers a promising method for natural product separation.
Area of Science:
- Pharmaceutical Chemistry
- Green Chemistry
- Materials Science
Background:
- Cocrystallization is a key technique for modifying drug properties.
- Separating structurally similar natural compounds presents significant challenges.
- Flavonoids are a class of natural products with diverse biological activities.
Purpose of the Study:
- To investigate the use of cocrystallization for separating structurally similar flavonoids.
- To explore competitive cocrystallization as a method for natural product purification.
- To evaluate the efficiency and purity of flavonoid separation using cocrystals.
Main Methods:
- Model flavonoids (baicalein, quercetin, myricetin) were used.
- Caffeine was employed as a coformer to create cocrystals.
- Competitive cocrystallization was induced in methanol solutions.
- Centrifugation was used to isolate the formed cocrystals.
- Physicochemical properties of cocrystals were analyzed (e.g., formation constant, Gibbs free energy, Hirshfeld surface, density of states).
Main Results:
- Caffeine formed cocrystals with all three flavonoids: BAI-CAF, QUE-CAF, and MYR-CAF.
- Preferential formation of MYR-CAF and QUE-CAF cocrystals demonstrated selective separation.
- Resolution ratios of 70-80% with purity >90% were achieved.
- Cocrystal 3 (MYR-CAF) exhibited the lowest formation constant and highest energy gap, indicating stronger interactions.
- Analysis confirmed MYR's higher propensity to form cocrystals with caffeine compared to QUE and BAI.
Conclusions:
- Competitive cocrystallization with caffeine is a viable and effective method for separating similar flavonoids.
- This approach offers a green and efficient strategy for purifying natural products.
- The study highlights the potential of cocrystallization in pharmaceutical and natural product chemistry.
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