Highly efficient and regioselective synthesis of dihydromyricetin esters by immobilized lipase

Li, Wei; Wu, Huan; Liu, Benguo; Hou, Xue-Dan; Wan, Daqing; Lou, Wen‐Yong; Zhao, Jian

doi:10.1016/j.jbiotec.2015.02.012

Cited by 31 publications

(43 citation statements)

References 19 publications

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“…The main determining factors on solvent influence are the log P and dielectric constant. It was noted that there was a negative correlation of solvent polarity with conversion yields which is consistent with the results obtained by Li et al (2015) when dihydromyricetin was esterified with vinyl acetate using immobilised lipase from Penicillium sp. Furthermore, it has been indicated that high dielectric constant is favoured for higher conversion (Chebil et al, 2007a).…”

Section: Effect Of Solventsupporting

confidence: 87%

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Lipase mediated synthesis of rutin fatty ester: Study of its process parameters and solvent polarity

2017

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Section: Effect Of Solventsupporting

confidence: 87%

“…5C). This could be due to the thermal inactivation of enzyme at higher temperature as suggested by Li et al (2015). However, tert-butanol system showed the maximum conversion at 60°C, indicating the thermal stability of the immobilised Candida antartica lipase.…”

Section: Effect Of Reaction Temperaturementioning

confidence: 99%

Lipase mediated synthesis of rutin fatty ester: Study of its process parameters and solvent polarity

2017

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“…Shen and colleagues incorrectly reported the stereo configuration of DHM [15]. Several other reports mentioned no stereo configuration for DHM [16][17][18]. These structural inconsistencies and errors may lead to misunderstandings about some of the chemical moieties in the DHM molecule.…”

Section: Resultsmentioning

confidence: 99%

Protective Effects of Dihydromyricetin against •OH-Induced Mesenchymal Stem Cells Damage and Mechanistic Chemistry

Liu

Lin

et al. 2016

Molecules

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Abstract:As a natural flavonoid in Ampelopsis grossedentata, dihydromyricetin (DHM, 2R,3R-3,5,7,3 1 ,4 1 ,5 1 -hexahydroxy-2,3-dihydroflavonol) was observed to increase the viability of ‚OH-treated mesenchymal stem cells using a MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl] assay and flow cytometry analysis. This protective effect indicates DHM may be a beneficial agent for cell transplantation therapy. Mechanistic chemistry studies indicated that compared with myricetin, DHM was less effective at ABTS + ‚ (2,2 1 -azino-bis(3-ethylbenzothiazoline-6-sulfonic acid radical) scavenging and reducing Cu 2+ , and had higher ‚O 2´a nd DPPH‚ (1,1-diphenyl-2-picrylhydrazyl radical) scavenging activities. Additionally, DHM could also chelate Fe 2+ to give an absorption maximum at 589 nm. Hence, such protective effect of DHM may arise from its antioxidant activities which are thought to occur via direct radical-scavenging and Fe 2+ -chelation. Direct radical-scavenging involves an electron transfer (ET) pathway. The hydrogenation of the 2,3-double bond is hypothesized to reduce the ET process by blocking the formation of a larger π-π conjugative system. The glycosidation of the 3-OH in myricitrin is assumed to sterically hinder atom transfer in the ‚O 2´a nd DPPH‚ radical-scavenging processes. In DHM, the Fe 2+ -chelating effect can actually be attributed to the 5,3 1 ,4 1 ,5 1 -OH and 4-C=O groups, and the 3-OH group itself can neither scavenge radicals nor chelate metal.

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“…However, low stability at acidic pH and high cost of raw materials limit its applications. Enzymatic acylation ✓ Improved lipid solubility, excellent regioselectivities, wide substrate specificity, green process, and mild reaction conditions Problem with stability, reusability, and catalytic performances of enzyme Li et al, 2015;Cao et al, 2017D. Liu, et al Trends in Food Science & Technology 91 (2019 6.2.2.…”

Section: Phospholipid Complexesmentioning

confidence: 99%

“…This is a determinant factor that limited the pharmacological effects and clinical application of DMY. To improve the bioavailability of DMY, researchers have tried to use DMY in new drug delivery systems such as inclusion complexes (Liu, Ma, et al, 2012;Ruan, Yu, Fu, & Zhu, 2005;Yang, Liu, Liu, & Zhang, 2011), nano-encapsule (Dalcin et al, 2017) or microemulsion (Solanki, Sarkar, & Dhanwani, 2012), co-crystals (Wang, Tong, et al, 2016), phospholipid complexes (Liu, Du, Jie, Chen, & Niu., 2009), and acylation (Cao et al, 2017;Guo, Zeng, Lu, & Shu, 2013;Li et al, 2015;Li, Zheng, & Ning., 2005) to provide higher solubility and bioavailability. In addition, the pharmacokinetic characteristics of DMY in animal models and human body are also vital to the evaluation of their in vivo bioavailability efficacy.…”

Section: Introductionmentioning

confidence: 99%

Dihydromyricetin: A review on identification and quantification methods, biological activities, chemical stability, metabolism and approaches to enhance its bioavailability

Liú

Mao

Ding

et al. 2019

Trends in Food Science & Technology

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Background: Dihydromyricetin (DMY) is an important plant flavonoid, which has received great attention due to its health-benefiting activities, including antioxidant, antimicrobial, anti-inflammatory, anticancer, antidiabetic and neuroprotective activities. DMY capsules have been sold in US as a nutraceutical supplement to prevent alcoholic hangovers. The major disadvantage associated with DMY is its chemical instability and poor bioavailability caused by the combined effects of its low solubility and poor membrane permeability. This limits its practical use in the food and pharmaceutical fields. Scope and approach: The present paper gives an overview of the current methods for the identification and quantification of DMY. Furthermore, recent findings regarding the main biological properties and chemical stability of DMY, the metabolism of DMY as well as different approaches to increase DMY bioavailability in both aqueous and lipid phases are discussed. Key findings and conclusions: Current trends on identification and quantification of DMY have been focused on spectral and chromatographic techniques. Many factors such as heat, pH, metal ions, could affect the chemical stability of DMY. Despite the diverse biological effects of DMY, DMY faces with the problem of poor bioavailability. Utilization of different delivery systems including solid dispersion, nanocapsule, microemuslion, cyclodextrin inclusion complexes, co-crystallization, phospholipid complexes, and chemical or enzymatic acylation has the potential to improve both the solubility and bioavailability. DMY digested in laboratory animals undergoes reduction, dehydroxylation, methylation, glucuronidation, and sulfation. Novel DMY delivery systems and basic pharmacokinetic studies of encapsulated DMY on higher animals and humans might be required in the future.

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Highly efficient and regioselective synthesis of dihydromyricetin esters by immobilized lipase

Cited by 31 publications

References 19 publications

Lipase mediated synthesis of rutin fatty ester: Study of its process parameters and solvent polarity

Lipase mediated synthesis of rutin fatty ester: Study of its process parameters and solvent polarity

Protective Effects of Dihydromyricetin against •OH-Induced Mesenchymal Stem Cells Damage and Mechanistic Chemistry

Dihydromyricetin: A review on identification and quantification methods, biological activities, chemical stability, metabolism and approaches to enhance its bioavailability

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