Enzymatic Acylation of Flavonoids from Bamboo Leaves: Improved Lipophilicity and Antioxidant Activity for Oil-Based Foods

Li, Haimei; Tan, Xinjia; Huang, Wenjing; Zhu, Xucheng; Yang, Xinquan; Shen, Yingbin; Yan, Rian

doi:10.1021/acs.jafc.2c07673

Cited by 2 publications

(1 citation statement)

References 30 publications

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“…On the other hand, the solubility of the C12 and C16 derivatives was 3 times lower than that of aglycone. A similar increase in lipophilicity and the partition coefficient (log P ) upon acylation has also been reported for other flavonoids. , …”

Section: Resultssupporting

confidence: 78%

Strategy for the Enzymatic Acylation of the Apple Flavonoid Phloretin Based on Prior α-Glucosylation

Gonzalez-Alfonso,

Alonso,

Poveda

et al. 2024

J. Agric. Food Chem.

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The acylation of flavonoids serves as a means to alter their physicochemical properties, enhance their stability, and improve their bioactivity. Compared with natural flavonoid glycosides, the acylation of nonglycosylated flavonoids presents greater challenges since they contain fewer reactive sites. In this work, we propose an efficient strategy to solve this problem based on a first α-glucosylation step catalyzed by a sucrose phosphorylase, followed by acylation using a lipase. The method was applied to phloretin, a bioactive dihydrochalcone mainly present in apples. Phloretin underwent initial glucosylation at the 4′-OH position, followed by subsequent (and quantitative) acylation with C8, C12, and C16 acyl chains employing an immobilized lipase from Thermomyces lanuginosus. Electrospray ionization-mass spectrometry (ESI-MS) and two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) confirmed that the acylation took place at 6-OH of glucose. The water solubility of C8 acyl glucoside closely resembled that of aglycone, but for C12 and C16 derivatives, it was approximately 3 times lower. Compared with phloretin, the radical scavenging capacity of the new derivatives slightly decreased with 2,2-diphenyl-1-picrylhydrazyl (DPPH) and was similar to 2,2azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS •+ ). Interestingly, C12 acyl-α-glucoside displayed an enhanced (3-fold) transdermal absorption (using pig skin biopsies) compared to phloretin and its α-glucoside.

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Section: Resultssupporting

confidence: 78%

Strategy for the Enzymatic Acylation of the Apple Flavonoid Phloretin Based on Prior α-Glucosylation

Gonzalez-Alfonso,

Alonso,

Poveda

et al. 2024

J. Agric. Food Chem.

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Five Significant Phenols from Phyllostachys glauca McClure Leaves Extracted Using Ultrasound-Assisted Deep Eutectic Solvent Extraction

Hei,

Wang,

Wang

et al. 2024

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Phyllostachys glauca McClure leaves (PML), as economical natural product material, contain abundant phenols, particularly flavonoids, with significant biological activities that contribute to their widespread applications in food, pharmaceutical, and cosmetic industries. To study the significant phenols in PML, an ultrasound-assisted deep eutectic solvent extraction method with high efficiency and low toxicity was established for extracting the phenols from PML and the bamboo leaves of 17 other bamboo species. Using the Ultra Performance Liquid Chromatography (UPLC) method, the content of phenols in the leaves of the 18 bamboo species was determined. PML were found to contain neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid, isoorientin, and orientin at contents of 0.793 ± 00.17 mg/g, 0.491 ± 0.0081 mg/g, 0.485 ± 0.0043 mg/g, 0.465 ± 0.0021 mg/g, and 0.044 ± 0.0005 mg/g, respectively, with a total content of 2.278 mg/g. These contents were significantly higher than those found in the leaves of 17 other bamboo species. Additionally, the significant phenols, neochlorogenic acid, chlorogenic acid, and cryptochlorogenic acid were found simultaneously in the leaves of 15 bamboo species, especially in PML. Therefore, PML can be viewed as the natural product material with considerable application values, owing to its abundant phenols, and can exhibit its importance in utilizing neochlorogenic acid, chlorogenic acid, and cryptochlorogenic acid as resources.

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Enzymatic Acylation of Flavonoids from Bamboo Leaves: Improved Lipophilicity and Antioxidant Activity for Oil-Based Foods

Cited by 2 publications

References 30 publications

Strategy for the Enzymatic Acylation of the Apple Flavonoid Phloretin Based on Prior α-Glucosylation

Strategy for the Enzymatic Acylation of the Apple Flavonoid Phloretin Based on Prior α-Glucosylation

Five Significant Phenols from Phyllostachys glauca McClure Leaves Extracted Using Ultrasound-Assisted Deep Eutectic Solvent Extraction

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