- Preparation of (5R)-5-Vinyloxazolidine-2-thione from Natural Epi-Progoitrin Using Immobilized Myrosinase
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Starting from (2S)-2-hydroxybut-3-enyl glucosinolate, i.e. epi-progoitrin 3, isolated from Crambe abyssinica ripe seeds, (5R)-5-vinyloxazolidine-2-thione (VOT) 8 was produced in enantiomerically pure form and high yield using a small bioreactor containing myrosinase - purified from Sinapis alba - immobilized on 18-36 mesh granular Nylon 6.6.
- Leoni, Onofrio,Marot, Christophe,Rollin, Patrick,Palmieri, Sandro
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- Modular Construction of Protected 1,2/1,3-Diols, -Amino Alcohols, and -Diamines via Catalytic Asymmetric Dehydrative Allylation: An Application to Synthesis of Sphingosine
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A new enantioselective catalysis has been developed for the one-step construction of methylene-bridged chiral modules of 1,2- and 1,3-OH and/or NH function(s) from δ- or λ-OH/NHBoc-substituted allylic alcohols and H2C=O / H2C=NBoc . A protonic nucleophile, either in situ-generated CH2OH or CH2NHBoc, is intramolecularly allylated to furnish eight possible 1,2- or 1,3-O,O, -O,N, -N,O, and -N,N chiral modules equipped with an ethenyl group in high yields and enantioselectivities. The utility of this method has been demonstrated in the five-step synthesis of sphingosine.
- Tanaka, Shinji,Gunasekar, Ramachandran,Tanaka, Tatsuya,Iyoda, Yoko,Suzuki, Yusuke,Kitamura, Masato
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- Antiviral activity of Isatidis Radix derived glucosinolate isomers and their breakdown products against influenza A in vitro/ovo and mechanism of action
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Ethnopharmacological relevance: Isatidis Radix, the sun-dried roots of Isatis indigotica Fortune ex Lindl., is one of the most usually used traditional Chinese medicines. For centuries, the herb has been employed in clinical practice for treatment of virus infection and inflammation. However, its active ingredients remain unclear. Aim of the study: In the present study, the anti-influenza virus activity of epiprogoitrin, progoitrin, epigoitrin and goitrin, the Isatidis Radix derived glucosinolate isomers and their breakdown products, was firstly evaluated in vitro and in ovo and their mechanism of action was investigated. Materials and methods: Epiprogoitrin, progoitrin, epigoitrin and goitrin were isolated from Isatidis Radix by chiral separation. In vitro and in ovo evaluations were performed on Madin-Darby canine kidney (MDCK) cells and embryonated eggs respectively, both using protocols including prevention, treatment and virus neutralization. Hemagglutination (HA) and neuraminidase (NA) inhibition assays were performed for further understanding of the antiviral mechanism. Results: Isatidis Radix derived glucosinolate isomers and their breakdown products all exhibited dose-dependent inhibition effect against influenza A virus (H1N1) without toxicity. The antiviral potency of the components was in the order of progoitrin > goitrin > epigoitrin > epiprogoitrin. The attachment of the constituents to the viral envelope conduced to the mechanism of their antiviral action without disturbing viral adsorption or budding. Conclusion: Taken together, these results are promising for further development of Isatidis Radix and may contribute an adjunct to pharmacotherapy for influenza virus infection.
- Dai, Zhong,Ma, Shuang-cheng,Nie, Li-xing,Wu, Yan-lin
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- Degradation of 2-Hydroxybut-3-enylglucosinolate (Progoitrin)
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Using a model system consisting of synthesized 2-hydroxybut-3-enylglucosinolate and a purified thioglucoside glucohydrolase preparation from Brassica napus, the effects of ascorbate, of Fe2+ and of Cu2+ were examined on the extent and course of glucosinolate degradation.Ascorbate was found to promote thioglucosidase activity to a considerable extent over the whole of the wide range of concentrations studied (0.024-400 mM), with a maximum (activation factor ca 110) at 1.57 mM ascorbate.Fe2+ slightly suppressed reaction, but caused a significant effect by directing degradation to 1-cyano-2-hydroxybut-3-ene rather than to 5-vinyloxazolidine-2-thione, and at low, catalytic, concentrations.Cu2+ had similar effect, but was a strong inhibitor of the reaction.Key Word Index - Glucosinolates; 2-hydroxybut-3-enylglucosinolate; progoitrin; thioglucoside glucohydrolase.
- MacLeod, Alexander J.,Rossiter, John T.
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- Synthesis of epigoitrin from (R)-(+)-4-hydroxy-γ-butyrolactone
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Epigoitrin is one of the major components of several natural species, including Isatis indigotica Fort, turnip, and cabbage. It presents antithyroid and antivirus activities. Here, we report an efficient and practical method for the chemical synthesis of epigoitrin from commercially available (R)-(+)-4-hydroxy-γ-butyrolactone.
- Yin, Wei,Qiao, Chunhua
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- BIOSYNTHESIS OF 2-HYDROXY-3-BUTENYLGLUCOSINOLATE AND 3-BUTENYLGLUCOSINOLATE IN BRASSICA NAPUS
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Desulpho-3-butenylglucosinolate is considered to be a potential late stage precursor in the biosynthesis of (R)-2-hydroxy-3-butenylglucosinolate (progoitrin) and 3-butenylglucosinolate (gluconapin) in Brassica.Chemically synthesized (β-D-glucopyranosyl)-4-pentenethiohydroxamic acid when administered to developing seedlings of Brassica napus cv Bienvenu was found to be well incorporated into both 2-hydroxy-3-butenylglucosinolate and 3-butenylglucosinolate, while feeding experiments with methionine have shown that de novo biosynthesis is slow.Analysis of seeds and developing seedlings has shown that levels of 2-hydroxy-3-butenylglucosinolate are maintained while 3-butenylglucosinolate levels are considerably reduced.
- Rossiter, J. T.,James, D. C.,Atkins, N.
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- The formation of 2-hydroxybut-3-enyl cyanide from (2s)-2-hydroxybut-3-enyl glucosinolate using immobilized myrosinase
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Starting from (2S)-2-hydroxybut-3-enylglucosinolate (epiprogoitrin) isolated from Crambe abyssinica seeds the chiralic 2-hydroxy-3-butenyl cyanide was produced in pure form and acceptable yield, using immobilized myrosinase purified from Sinapis alba on a Nylon 6.6 membrane.
- Leoni,Felluga,Palmieri
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- Synthetic method of antiviral drug (R,S)-goitrine
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The invention discloses a synthetic method of an antiviral drug (R,S)-goitrine. The synthesis method comprise the following steps: dissolving nitromethane in a proper solvent, adding acrolein, carrying out stirring at a set temperature for a period of time to obtain a solution A, dissolving triethylamine into residual nitromethane to obtain a solution B, dropwise adding the solution B into the solution A for a reaction, carrying out rotary evaporation to remove the solvent and unreacted nitromethane after the reaction is completed, and carrying out column chromatography separation on the obtained mixture to obtain 1-nitro-3-butenyl-2-ol; reducing nitro of the 1-nitro-3-butenyl-2-ol by an iron powder reduction method to obtain 1-amino-3-butenyl-2-ol; and further carrying out a cyclization reaction on the 1-amino-3-butenyl-2-ol with carbon disulfide to generate the (R,S)-goitrine. The synthetic method disclosed by the invention had the advantages of low cost, simple operation, safety andenvironmentally friendliness.
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Paragraph 0016; 0030; 0034; 0039; 0044; 0049
(2019/04/26)
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- Preparation method of 5-vinyl-2-sulfo-oxazolidine
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The invention discloses a preparation method of 5-vinyl-2-sulfo-oxazolidine. The preparation method comprises the following steps: (1) using acrolein and trimethylsilyl cyanide as raw materials for reaction under the catalysis of zinc iodide to obtain 2-[(trimethyorganosilyl)oxy]-3-butenenitrile; (2) in a toluene solution, using a red aluminum solution as a reducing agent and potassium carbonate and methanol as a desiliconizing agent, performing reduction and desiliconization on the 2-[(trimethyorganosilyl)oxy]-3-butenenitrile to obtain 1-amino-3-butene-2-alcohol; (3) enabling the 1-amino-3-butene-2-alcohol to react with carbon disulfide, and using hydrogen peroxide as a desulfurizing agent to obtain the 5-vinyl-2-sulfo-oxazolidine. The fatty chain cyanogroup used in the preparation methodis the red aluminum solution; compared with conventional lithium aluminum hydride, the red aluminum solution has simple operation conditions and is low in cost. In the reduction, methylbenzene, instead of traditional combustible liquid such as diethyl ether and the like, is used as a solvent, so that the reaction conditions are safer. In the annulations in the step (3), the hydrogen peroxide replaces original lead nitrate and serves as the desulfurizing agent, so that the pollution to the environment can be reduced, and the method is safe and environmentally-friendly.
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Paragraph 0023; 0026; 0027; 0030; 0031; 0034
(2019/05/08)
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- A high-purity 5 - vinyl oxazolidine -2 - thione preparation method
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The invention discloses a preparation method of high-purity 5-vinyl oxazolidine-2-thioketone. The preparation method comprises the following steps: carrying out coordination on 1-amino-3-butene-2-alcohol taken as a starting material by using lead nitrate water solution, carrying out annulation on the raw material and CS2 in alkaline environment of potassium hydroxide solution, filtering the reaction liquid, extracting the reaction liquid by using ethyl acetate, carrying out liquid separation, drying and rotary evaporation to obtain a crude product, purifying the water solution containing the crude product through a preparative liquid chromatograph, receiving a mobile phase in the retention time period of a target product, and carrying out rotary evaporation and drying to obtain the product. According to the method, the steps are simple, the operation is convenient, the cost is low and the output is relatively high; and according to the method, the single-pass preparation amount can be up to 0.2-0.3g and the purity is 99.0-99.5%.
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Paragraph 0033-0048
(2017/08/24)
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- Expedient synthesis of epigoitrin from L-ascorbic acid
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Epigoitrin is the main bioactive constituent of an important traditional Chinese herbal medicine, Radix isatidis. Reported pharmacological effects of epigoitrin include antiviral, anticancer, and antithyroid activities. Extensive biological exploration of
- Yang, Jing-Jing,Wu, Jian-Zhong,Qiao, Chunhua
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supporting information
p. 1240 - 1244
(2014/04/17)
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- Chemo-enzymatic preparation from renewable resources of enantiopure 1,3- oxazolidine-2-thiones
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Chiral 1,3-oxazolidine-2-thiones were prepared in enantiopure form from renewable resources through an enzymatic process involving immobilized myrosinase (thioglucoside glucohydrolase E.C. 3.2.3.1). (C) 2000 Elsevier Science Ltd.
- Leoni, Onofrio,Bernardi, Roberta,Gueyrard, David,Rollin, Patrick,Palmieri, Sandro
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p. 4775 - 4780
(2007/10/03)
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