Novel and Highly Efficient Regioselective Route to Helicid Esters by Lipozyme TLL

Yang, Rongling; Zhao, Xiangjie; Liu, Xueming

doi:10.1371/journal.pone.0080715

Cited by 10 publications

(8 citation statements)

References 23 publications

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“…The same phenomenon has already been observed by Zhang et al [35] when carrying out an investigation on esterification of sorbitol and a series of fatty acids (C10—C18) in tert -butanol, catalyzed by Candida sp. 99–125 lipase; Adelhorst et al [11] also observed a faster reaction with the longer fatty acids (C12—C18) compared to the shorter ones (C8—C10) in the solvent-free system, by using a set of lipases from different sources as the catalysts, whereas Yang et al [36] carried out regioselective acylation of helicid with fatty acid vinyl esters in tetrahydrofuran and observed a bell-shaped relationship between the initial reaction rate and the chain length of the vinyl ester.…”

Section: Resultsmentioning

confidence: 99%

Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic Solvents

et al. 2016

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Sugar fatty acid esters (SFAEs) are biocompatible nonionic surfactants with broad applications in food, cosmetic, and pharmaceutical industries. They can be synthesized enzymatically with many advantages over their chemical synthesis. In this study, SFAE synthesis was investigated by using two reactions: (1) transesterification of glucose with fatty acid vinyl esters and (2) esterification of methyl glucoside with fatty acids, catalyzed by Lipozyme TLIM and Novozym 435 respectively. Fourteen ionic liquids (ILs) and 14 deep eutectic solvents (DESs) were screened as solvents, and the bisolvent system composed of 1-hexyl-3-methylimidazolium trifluoromethylsulfonate ([HMIm][TfO]) and 2-methyl-2-butanol (2M2B) was the best for both reactions, yielding optimal productivities (769.6 and 397.5 µmol/h/g, respectively) which are superior to those reported in the literature. Impacts of different reaction conditions were studied for both reactions. Response surface methodology (RSM) was employed to optimize the transesterification reaction. Results also demonstrated that as co-substrate, methyl glucoside yielded higher conversions than glucose, and that conversions increased with an increase in the chain length of the fatty acid moieties. DESs were poor solvents for the above reactions presumably due to their high viscosity and high polarity.

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Section: Resultsmentioning

confidence: 99%

Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic Solvents

et al. 2016

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“…Nevertheless, the initial reaction rate decreased with further extending chain length from C12 to C16, owing to the higher steric hindrance of the longer-chain acyl donors. Previous studies have found that the biocatalysts from different sources showed different catalytic properties for the different acyl donors due to the specific structure of the lipase active site and the acyl ( Wang and Zong, 2009 ; Yang et al, 2013 ; Li X. F. et al, 2018 ; Yang W. et al, 2019 ). For example, the Pseudomonas aeruginosa cells were more specific toward the medium-chain acyl donors, as well as Candida antarctica lipase B (Novozyme 435) and Thermomyces lanuginosus lipase (Lipozyme TLL) ( Wang and Zong, 2009 ; Yang et al, 2013 ; Yang R. L. et al, 2019 ), while the whole cells of Candida parapsilosis was most efficient for the short chain acyl donor, vinyl propionate.…”

Section: Resultsmentioning

confidence: 99%

A facile and efficient synthesis approach of salidroside esters by whole-cell biocatalysts in organic solvents

Yang

Wang

Zhao

et al. 2022

Front. Bioeng. Biotechnol.

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Salidroside, the main bioactive compound isolated from the plant source of Rhodiola rosea L, possesses broad-spectrum pharmacological activities, but suffers from the low cell membranes permeability and alimentary absorption due to its high polarity. Therefore, a whole-cell catalytic strategy for the synthesis of salidroside esters was explored to improve its lipophilicity. The results showed that Aspergillus oryzae demonstrated the highest biocatalytic activity among the microbial strains tested. For the synthesis of salidroside caprylate, the optimum conditions of reaction medium, Aspergillus oryzae amount, molar ratio of vinyl caprylate to salidroside and reaction temperature were acetone, 30 mg/ml, 10°C and 40°C, respectively. Under these conditions, the initial reaction rate was 15.36 mM/h, and substrate conversion and regioselectivity all reached 99%. Moreover, the results indicated that although various 6′-monoesters derivatives of salidroside were exclusively obtained with excellent conversions (96%–99%), the reaction rate varied greatly with different chain-length acyl donors. This study details an efficient and cost-effective biocatalytic approach for the synthesis of salidroside esters by using Aspergillus oryzae as a catalyst for the first time. Considering the whole cell catalytic efficiency and operational stability, this strategy may provide a new opportunity to develop green industrial processes production for ester derivatives of salidroside and its analogues.

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“…Besides, Yang et al . also reported a novel and highly efficient regioselective route to helicid esters (Yang et al ., ). This research suggested more possibilities to explore efficient agents ameliorated from helicid.…”

Section: Discussionmentioning

confidence: 99%

Helicid alleviates pain and sleep disturbances in a neuropathic pain‐like model in mice

Zhang

Wang

et al. 2017

Journal of Sleep Research

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Natural helicid (4-formylphenyl-O-β-d-allopyranoside), a main active constituent from seeds of the Chinese herb Helicia nilagirica, has been reported to exert a sedative, analgesic and hypnotic effect, and is used clinically to treat neurasthenic syndrome, vascular headaches and trigeminal neuralgia. In the current study, mechanical allodynia tests, electroencephalograms, electromyogram recordings and c-Fos expression in neuropathic pain-like model mice of partial sciatic nerve ligation were used to investigate the effect of helicid on neuropathic pain and co-morbid insomnia. Our results showed that helicid at a dose of 100, 200 or 400 mg kg could increase the mechanical threshold by 2.5-, 2.8- and 3.1-fold for 3 h after administration, respectively. Helicid at 200 and 400 mg kg given at 07:00 hours increased the amount of non-rapid eye movement sleep in a 3-h period by 1.27- and 1.35-fold in partial sciatic nerve ligated mice. However, helicid (400 mg kg ) given at 21:00 hours did not change the sleep pattern in normal mice. Immunohistochemical study showed that helicid (400 mg kg ) administration could reverse the increase of c-Fos expression in the neurons of the rostral anterior cingulate cortex and tuberomammillary nucleus, and the decrease of c-Fos expression in the ventrolateral preoptic area caused by partial sciatic nerve ligation. These results indicate that helicid is an effective agent for both neuropathic pain and sleep disturbances in partial sciatic nerve ligated mice.

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Novel and Highly Efficient Regioselective Route to Helicid Esters by Lipozyme TLL

Cited by 10 publications

References 23 publications

Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic Solvents

Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic Solvents

A facile and efficient synthesis approach of salidroside esters by whole-cell biocatalysts in organic solvents

Helicid alleviates pain and sleep disturbances in a neuropathic pain‐like model in mice

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