Synthesis of α-cichoriin Using <i>Deinococcus geothermalis</i> Amylosucrase and Its Antiproliferative Effect

Moon, Keumok; Park, Hyun Su; Lee, Areum; Min, Jugyeong; Park, Yunjung; Cha, Jaeho

doi:10.48022/mbl.2203.03002

Cited by 3 publications

(4 citation statements)

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“…Application of HPLC–PDA–ESI–tQ–MS and micro-sized column (1 × 50 mm) successfully separated 25 metabolites in 5 min in fresh lovage root extract. Identification was achieved after comparison of retention times and ultraviolet (UV) and mass spectra with reference standards and the literature data [ 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 ] ( Figure 1 a and Table 2 ). The most abundant group of metabolites was coumarins, including nineteen compounds ( 1 – 3 , 5 , 6 , 9 , 10 , 14 – 25 ), and a lesser group of hydroxycinnamates consisted of six acids ( 4 , 7 , 8 , and 11 – 13 ).…”

Section: Resultsmentioning

confidence: 99%

“…Simple coumarins with a bicyclic structure included esculetin (6,7-dihydroxycoumarin, 5 ) and two of its glycosides, i.e., of esculin (esculetin 6- O -glucoside, 1 ) [ 51 ] and cichoriin (esculetin 7- O -glucoside, 2 ) [ 52 ]; umbelliferone (7-hydroxycoumarin, 10 ) and two of its glycosides, i.e., skimmin (umbelliferone O -glucoside, 6 ) [ 55 ] and apiosylskimmin ( 3 ) [ 39 ]; and osthole (7-methoxy-8-isopentenylcoumarin, 23 ) [ 61 ] ( Figure 2 ). None of the simple coumarins were previously found in the lovage roots.…”

Section: Resultsmentioning

confidence: 99%

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Coumarins of Lovage Roots (Levisticum officinale W.D.J.Koch): LC-MS Profile, Quantification, and Stability during Postharvest Storage

Оленников

2022

Metabolites

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Lovage (Levisticum officinale W.D.J. Koch) is a known aromatic apiaceous species that is widely used as a culinary and medicinal plant. Traditionally, more scientific attention has been paid to lovage volatiles, while other groups of compounds have been underutilized. In this study, metabolites of fresh lovage roots were investigated by liquid chromatography–mass spectrometry, and 25 compounds were identified, including coumarins as basic components and minor hydroxycinnamates; most were detected for the first time in the plant. Four major coumarins (including apterin, xanthotoxin, isopimpinellin, and pimpinellin) were successfully separated by a validated HPLC–PDA method, and the fresh roots of seven lovage cultivars as well as the dry roots of commercial lovage were quantified. The coumarin content deviation was 1.7–2.9 mg/g in the fresh roots and 15–24 mg/g in the dry roots. A variation in the coumarin level was found during storage of the fresh lovage roots at chill and room temperatures, while storage of the dried roots at room temperature showed the lowest loss of target compounds. This new information about the metabolites of lovage indicates the prospects of the plant roots as a source of dietary coumarins.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Coumarins of Lovage Roots (Levisticum officinale W.D.J.Koch): LC-MS Profile, Quantification, and Stability during Postharvest Storage

Оленников

2022

Metabolites

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“…However, at present, there are very few studies on the solubility of esculetin, and only some studies have mentioned information about the solubility of esculetin. Moon pointed out that due to the low solubility of fishskin in water and ethanol, coupled with extensive phase II metabolism, esculetin is rapidly eliminated from the human body, thus affecting the medicinal value of esculetin; Zuo mentioned that esculetin’s poor water solubility may limit its therapeutic effect; Liu found that the low esculetin solubility, which resulted in low oral absorption and bioavailability, prevents the antioxidant activity of esculetin from fully releasing in vivo, thereby hampering its clinical application.…”

Section: Introductionmentioning

confidence: 99%

Solubility Determination and Thermodynamic Model Analysis of Esculetin in Different Solvents from 273.15 to 318.15 K

Yang,

Yan,

Huang

et al. 2024

J. Chem. Eng. Data

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Esculetin is derived from the leaves of lemons of Rutaceae and the bark of bittersweet ash, belladonna, mandala, and Rehmannia plants. In this research, the solubility of esculetin in ten solvents such as ethyl acetate, isobutyl alcohol, water, methanol, acetonitrile, n-propyl alcohol, isopropyl alcohol, n-butanol, ethanol, and acetone was determined by utilizing static equilibrium-high performance liquid chromatography (HPLC) under standard atmospheric pressure conditions and temperatures in the range of 273.15 to 318.15 K. Among the above ten pure solvents, water displayed the least solubility, while methanol exhibited the highest solubility. At the same temperature (T = 273.15 ∼ 318.15 K), the solubility of esculetin increased with the increase of the molar ratio of soluble solvents. Similarly, when the temperature increases (T = 273.15 ∼ 318.15 K), the solubility of the three binary solvents increases under the condition of a constant molar ratio. The above results suggest that the main factor affecting the solubility of esculetin in the solvent may be the polarization/bipolarity of the solvent. The experimental data was fitted by five thermodynamic models (the Buchowski−Ksiazaczak λh model, the Modified Apelblat model, the Jouyban−Acree model, the SUN model, and the CNIBS/R-K model), and the relative average deviation and root-mean-square deviation of the data were calculated, which proved that the correlation of the solubility data and the five models was relatively good. XRD and DSC were used to detect the crystal form and stability of esculetin during the experiment.

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“…Some coumarins activate phosphatidylinositol-3-kinase (PI3K) and/or 5′-AMP-activated kinase (AMPK) as the main signaling pathways that promote glucose transporter type 4 (GLUT4) expression, which mediates glucose transport in fat and muscle and improves insulin sensitivity [ 21 , 22 ]. Cichoriin (6-hydroxy-7-O-glucosylcoumarin or aesculetin 7-glucoside) is a member of the coumarins with an attached sugar moiety that enhances its water solubility, bioavailability and oxidative stability with reduced toxicity [ 23 ]. Cichoriin has been shown to display interesting bioactivities, namely antibacterial [ 24 ], antifungal [ 25 ], antiviral [ 26 ] antioxidant [ 27 ], anti-inflammatory [ 28 ] and photoprotective activities [ 29 ].…”

Section: Introductionmentioning

confidence: 99%

Mechanistic Insights into the Ameliorative Effect of Cichoriin on Diabetic Rats—Assisted with an In Silico Approach

et al. 2022

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Type 2 diabetes mellitus is considered to be a substantial socioeconomic burden worldwide on both patients and governments. Coumarins are biomolecules with a diversity of biological activities. The current investigation aimed to explore the ameliorative effects of cichoriin, which is a type of coumarin, on high-fat diet/streptozotocin (HFD/STZ)-induced diabetic rats. Methods: Rats were allocated into five groups. Group I was considered as the control group, while the other groups were HFD/STZ-induced diabetic rats. Group II was assigned as the diabetic control. Groups III and IV were treated with cichoriin (50 or 100 mg/kg, respectively). Group V received glibenclamide (5 mg/kg) (as a positive control). The blood glucose (BG), serum insulin, triglycerides (TG), total cholesterol (TC), total antioxidant capacity (TAC), catalase, hepatic superoxide dismutase (SOD) and content of malondialdehyde (MDA) were assessed. Histopathological and immunohistochemistry analysis of pancreatic tissue were performed. mRNA and protein expressions of GLUT4, AMPK, and PI3K were estimated. Results: Cichoriin treatment ameliorated HFD/STZ-induced diabetic conditions and mitigated the histopathological characteristics of the pancreas, as well as increasing pancreatic insulin expression. This decreased the levels of BG, TG, TC, and MDA and improved the TAC, catalase and SOD contents. Cichoriin demonstrated upregulation of mRNA and protein expressions of GLUT4, AMPK, and PI3K. The in silico binding of cichoriin with GLUT4, AMPK, and PI3K supported the possible current activities. Conclusion: Collectively, this work highlighted the potential role of cichoriin in mitigating HFD/STZ-induced diabetic conditions and showed it to be a valuable product.

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Synthesis of α-cichoriin Using Deinococcus geothermalis Amylosucrase and Its Antiproliferative Effect

Cited by 3 publications

References 43 publications

Coumarins of Lovage Roots (Levisticum officinale W.D.J.Koch): LC-MS Profile, Quantification, and Stability during Postharvest Storage

Coumarins of Lovage Roots (Levisticum officinale W.D.J.Koch): LC-MS Profile, Quantification, and Stability during Postharvest Storage

Solubility Determination and Thermodynamic Model Analysis of Esculetin in Different Solvents from 273.15 to 318.15 K

Mechanistic Insights into the Ameliorative Effect of Cichoriin on Diabetic Rats—Assisted with an In Silico Approach

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