Characterization and Enhanced Antioxidant Activity of the Cysteinyl β-Cyclodextrin-Baicalein Inclusion Complex

Kim, Hwanhee; Yiluo, Hu; Park, Sung Yong; Lee, Jae Yung; Cho, Eunae; Jung, Seunho

doi:10.3390/molecules21060703

Cited by 23 publications

(17 citation statements)

References 29 publications

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“…Cysteinyl β‐CD was synthesized, and inclusion complexes of cysteinyl β‐CD and baicalein were formed. The chemical structure of cysteinyl β‐CD is shown in Figure A, which was defined using matrix‐assisted laser desorption ionization‐time of ﬂight mass spectrometry and NMR spectroscopy . The complexation mode of cysteinyl β‐CD and baicalein was determined from NOESY spectrum, and the proposed model, as well as the chemical structure of baicalein are shown in Figure B.…”

Section: Resultsmentioning

confidence: 99%

Inclusion complexes of cysteinyl β‐cyclodextrin with baicalein restore collagen synthesis in fibroblast cells following ultraviolet exposure

Lee

Ahn

Kim

et al. 2018

J of Cellular Biochemistry

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Baicalein, a bioactive flavonoid, has poor water solubility, thereby limiting its use in a wide range of biological applications. In the present study, we used inclusion complexes of cysteinyl β-cyclodextrin (β-CD) with baicalein to enhance the stability and solubility of baicalein in aqueous solution. We examined the effects of inclusion complexes of cysteinyl β-CD on collagen synthesis following ultraviolet (UV) irradiation, as well as the mechanisms underlying its effects. Our findings demonstrated that baicalein significantly restored collagen synthesis in the UVexposed human fibroblast Hs68 cells. In addition, synthetic cysteine functionalized β-CDs were found to promote baicalein-induced collagen synthesis. Inclusion complexes of cysteinyl β-CDs with baicalein significantly upregulated the protein expression of type I collagen and activated the transcription of type I, II, and III collagen. Inclusion complexes of cysteinyl β-CDs with baicalein also downregulated matrix metalloproteinase -1 and -3, and α-smooth muscle actin expression. In addition, inclusion complexes of cysteinyl β-CDs with baicalein attenuated the expression of caveolin-1, but this treatment enhanced the UV-induced phosphorylation of Smad in the transforming growth factor-β pathway. These results suggested that the newly synthesized derivative of CD can be used as a complexing agent to enhance the bioavailability of flavonoids such as baicalein, especially in restoring collagen synthesis.baicalein, collagen, cysteinyl β-cyclodextrin (β-CD), inclusion complex, ultraviolet-exposed fibroblast 1 | INTRODUCTION Collagen plays an important role in maintaining the skin and is largely responsible for its strength and resilience. Skin aging is inevitably associated with disturbances in collagen metabolism, such as decreased synthesis and increased degradation. 1 Skin aging is influenced by both intrinsic (genetics) and extrinsic factors (environmental exposure). Ultraviolet (UV) irradiation is particularly important extrinsic risk factor. 2 Skin aging involves the degradation of dermal collagen fibrils in the extracellular matrix by matrix metalloproteinases (MMPs). 3 UV irradiation of the connective tissue in the skin induces the production of MMP-1, MMP-3, and MMP-9 in the normal human skin in vivo. This leads to collagen degradation, especially of type I procollagen (COLI), the J Cell Biochem. 2019;120:4032-4043. wileyonlinelibrary.com/journal/jcb 4032 |

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Section: Resultsmentioning

confidence: 99%

Inclusion complexes of cysteinyl β‐cyclodextrin with baicalein restore collagen synthesis in fibroblast cells following ultraviolet exposure

Lee

Ahn

Kim

et al. 2018

J of Cellular Biochemistry

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“…Por otro lado, el complejo del extracto con la β-CD muestra poca actividad antioxidante, la cual pudo verse afectada por el modo de formación del complejo, al existir un enmascaramiento de los grupos funcionales específicos para el efecto antioxidante (13). La formación del complejo entre el extracto y la β-CD fue evidenciada por la completa desaparición de señales por IR del extracto en el complejo de inclusión realizado por FSC, lo cual pueden deberse a que la relación β-CD/extracto es muy grande y por ello es muy difícil verlas, ya que las señales de β-CD pueden enmascararlas.…”

Section: Discussionunclassified

Antioxidant activity of the inclusion complex of bixa orellana seeds extract in ß-cyclodextrin obtained by supercritical co2

Meñaca

Restrepo

Colmenares

2018

Vitae

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RESUMENAntecedentes: los extractos de Bixa orellana son utilizados como colorante de alimentos, y presentan una actividad antioxidante de importancia farmacéutica. Su uso puede limitarse por su inestabilidad, donde el proceso de inclusión en β-ciclodextrina (β-CD) por fluido supercrítico con CO 2 (FSC-CO 2 ) es una alternativa para mediar esta desventaja. Objetivos: comparar diferentes condiciones de temperatura y presión de extracción por FSC-CO 2 , para determinar cuál de estas permite obtener un extracto de Bixa orellana con mayor actividad antioxidante, y evaluar el efecto de la inclusión en β-CD, en dicha capacidad antioxidante. Métodos: se obtuvieron extractos por FSC-CO 2 variando condiciones de presión y temperatura: (I) 3583 psi, 35°C, (II) 1413 psi, 35°C, (III) 2184 psi, 45°C, (IV) 5076 psi, 45°C, y (V) 2300 psi, 40°C. Se evaluó la actividad antioxidante de los extractos obtenidos mediante el método DPPH, determinando su IC 50 . Se realizó el complejo de inclusión en β-CD del extracto que presentó la mayor actividad antioxidante, por el método FSC-CO 2 , y fue caracterizado por IR, DSC y RMN. Mediante análisis comparativo de los espectros de la β-CD, extracto libre y el complejo extracto/β-CD, se verificó el acomplejamiento, y se evaluó la capacidad antioxidante del complejo de inclusión. Resultados: el extracto con mayor actividad antioxidante se obtuvo bajo la condición de extracción IV, con un IC 50 de 23,55 μg/ mL, seguido del extracto II (28,76 μg/mL), del extracto III (37,23 μg/mL), del extracto V (81,09 μg/mL) y del extracto I (193,82 μg/mL), los cuales presentaron diferencias significativas (P<0,01). Los espectros obtenidos por IR, DSC y RMN presentaron desplazamientos propios del proceso de encapsulamiento. El valor IC 50 del complejo extracto/β-CD fue de 104,84 μg/mL, siendo significativamente mayor al valor obtenido para el extracto puro (23,55 μg/mL). Conclusión: el extracto de Bixa orellana con una actividad antioxidante mayor se obtuvo por fluido supercrítico a 5076 psi de presión y 45°C de temperatura. Las variaciones de los espectros IR, DSC y RMN demuestran la inclusión del extracto en la β-CD, y los valores de IC 50 indican el efecto protector de la β-CD ante la reacción con el radical DPPH. ABSTRACTBackground: Bixa orellana extracts are used to food coloring and it is important in pharmaceutical industry as a potential source of antioxidant activity. The application may be limited because it is unstable, but the process of inclusion in β-cyclodextrin (β-CD) by supercritical fluid CO 2 (FSC-CO 2 ) is an alternative to mediate this disadvantage. Objectives: we compared different conditions of temperature and pressure of FSC-CO 2 extraction, to obtain a Bixa orellana extract with excellent antioxidant activity, 84 Vitae s.m. Vásquez M. et al.and we evaluated the effect of inclusion in β-CD in the antioxidant capacity. Methods: extracts were obtained by FSC-CO 2 with different conditions of pressure and temperature: (I) 3583 psi, 35°C, (II) 1413 psi, 35°C, (III) 2184 psi, 45°C, (IV) 5076 ...

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“…1) CD Host-Guest 포접 복합체로 인한 화장품 안정성 효과 Caveolin-1 repression collagen I expression increased. None toxicity and side effect Lee et al, 2015 Isoliguiritigenin/ methyl-β-cyclodextrin Antimicrobial effect Kim et al, 2015 Baicalein/cys-β-cyclodextrin Antioxidant activity improvement Kim et al, 2016 Collagen I, Ⅱ, and Ⅲ expression increased.…”

Section: Cd의 화장품 원료로서의 유용성mentioning

confidence: 99%

Review of the Usability of Cyclodextrin as a Cosmetic Ingredient

Lee¹,

Park²

2019

Asian J Beauty Cosmetol

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Skin is the outermost barrier of the body, making it vulnerable to various external stimuli that can directly influence skin aging. To maximize the impact of cosmetics that delay skin aging, the stabilization of cosmetic ingredients is necessary. In addition to microencapsulation, liposome, and liquid crystal methods to increase the bioavailability of cyclodextrin, various studies have been conducted that utilize its structural characteristics to improve its properties of solubility, stability, and sustained release. In the present study, we reviewed previous investigations demonstrating that cyclodextrin enhanced the usefulness of various active ingredients as cosmetics materials based on its structural characteristics. Cyclodextrin inclusion complexes of esculin, hydrogel, coenzyme Q10, and genistein were compared with each non-inclusion material. The results showed that cyclodextrin increased solubility and improved skin permeability. Additionally, cysteinyl β-cyclodextrin, formed by combining a structural unit of the amino acid cysteine with β-cyclodextrin, showed a complexing function specific to the flavonoid baicalein. The strongly hydrophilic cysteine site of the complex improved the dissolution of baicalein in water. Therefore, further studies should investigate the various structure-specific host complexes with different cyclodextrin structure derivatives besides the cysteinyl group to enhance the already verified efficacy of the effective ingredients. Furthermore, it is expected that cyclodextrin will be commercialized as a stabilizing material for active ingredients in the cosmetic industry if clinical studies can prove the effectiveness of the β-cyclodextrin inclusion function in functional cosmetics.

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Characterization and Enhanced Antioxidant Activity of the Cysteinyl β-Cyclodextrin-Baicalein Inclusion Complex

Cited by 23 publications

References 29 publications

Inclusion complexes of cysteinyl β‐cyclodextrin with baicalein restore collagen synthesis in fibroblast cells following ultraviolet exposure

Inclusion complexes of cysteinyl β‐cyclodextrin with baicalein restore collagen synthesis in fibroblast cells following ultraviolet exposure

Antioxidant activity of the inclusion complex of bixa orellana seeds extract in ß-cyclodextrin obtained by supercritical co2

Review of the Usability of Cyclodextrin as a Cosmetic Ingredient

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