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An Optimized Facile Procedure to Synthesize and Purify Allicin

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An Optimized Facile Procedure to Synthesize and Purify Allicin molecules Article An Optimized Facile Procedure to Synthesize and Purify Allicin Frank Albrecht 1,†, Roman Leontiev 1,2,†, Claus Jacob 2 and Alan J. Slusarenko 1,* 1 Department of Plant Physiology, RWTH Aachen University, D-52056 Aachen, Germany; [email protected] (F.A.); [email protected] (R.L.) 2 Division of Bioorganic Chemistry, School of Pharmacy, Campus B2 1, University of Saarland, D-66123 Saarbruecken, Saarland, Germany; [email protected] * Correspondence: [email protected] † These authors contributed equally to this work. Academic Editors: Thomas J. Schmidt and Derek J. McPhee Received: 1 March 2017; Accepted: 5 May 2017; Published: 10 May 2017 Abstract: Allicin is a reactive sulfur species (RSS) and defence substance from garlic (Allium sativum L.). The compound is a broad-spectrum antibiotic that is also effective against multiple drug resistant (MDR) strains. A detailed protocol for allicin synthesis based on diallyl-disulfide (DADS) oxidation by H2O2 using acetic acid as a catalyst was published in 2001 by Lawson and Wang. Here we report on improvements to this basic method, clarify the mechanism of the reaction and show that it is zero-order with respect to DADS and first-order with respect to the concentration of H2O2. The progress of allicin synthesis and the reaction mechanism were analyzsd by high-performance liquid chromatography (HPLC) and the identity and purity of the products was verified with LC-MS and 1H-NMR. We were able to obtain allicin of high purity (>98%) and >91% yield, with standard equipment available in any reasonable biological laboratory. This protocol will enable researchers to prepare and work with easily and cheaply prepared allicin of high quality. Keywords: allicin; Allium sativum; diallyl-disulfide; catalytic oxidation; reactive sulfur species; dipropyl-disulfide; thiosulfinate 1. Introduction The sulfur-containing compound allicin (2-Propene-1-sulfinothioic acid S-2-propenyl ester, or diallyl-thiosulfinate, DATS) is produced in damaged tissue of garlic (Allium sativum), ramsons (Allium ursinum), and hooker chives (Allium hookeri) and gives these plants their typical odours [1]. Garlic is highly valued in the cuisines of many nations because of its excellent flavour and its pungent smell. Additionally, it has long been believed that allicin, or at least garlic consumption, is beneficial to health [2]. In 1944 Cavallito and Bailey demonstrated that allicin inhibited the growth of Staphylococcus aureus and other bacteria in liquid culture [3]. Furthermore, allicin was shown to induce apoptosis, often selectively, in mammalian cancer cells cultured in vitro [4,5], in intact tissues in vivo [6], and in cells of yeast (Saccharomyces cerevisiae), a model fungal eucaryote [7]. These properties turn allicin into a highly interesting compound for clinical investigations. Stoll and Seebeck first reported the synthesis of allicin in 1947, but without specifying experimental details [8]. Their chemical synthesis of allicin was based on the oxidation of diallyl-disulfide (DADS) by peracetic acid as a mild oxidizing agent. A more detailed protocol of this basic method was published by Lawson and Koch in 1994 and Lawson and Wang in 2001 [9,10]. Other methods to synthesize allicin utilizing magnesium monoperoxyphthalate [11] or chloroperbenzoic acid have also been reported [12,13]. Nevertheless, it is still challenging to obtain pure allicin in acceptable yields. Molecules 2017, 22, 770; doi:10.3390/molecules22050770 www.mdpi.com/journal/molecules Molecules 2017, 22, 770 2 of 13 In the original protocol, DADS was stirred into a mixture of acetic acid and H O and incubated Molecules 2017, 22, 770 2 2 2 of 14 at room temperature (RT) for 4 h with constant stirring. The reaction was stopped by adding five volumesIn the oforiginal water protocol, and extracted DADS was with stirre dichloromethaned into a mixture of (DCM) acetic acid to retrieveand H2O allicin2 and incubated along with unreactedat room DADS, temperature some acetic (RT) acid,for 4 andh with DCM-soluble constant stirring. reaction The byproducts. reaction was The stopped lipophilic by adding undissociated five acidvolumes catalyst of in water the DCMand extracted phase with was dichloromethan neutralized withe (DCM) aqueous to retrieve sodium allicin carbonate along with solution unreacted which facilitatedDADS, partitioning some acetic ofacid, the and hydrophilic DCM-soluble sodium reaction acetate byproducts. generated The into lipophilic the aqueous undissociated phase. DCM acid was removedcatalyst by in rotary the DCM evaporation phase was at neutralized RT at reduced with aq pressureueous sodium to yield carbonate an oily residuesolution ofwhich allicin, facilitated unreacted DADS,partitioning and byproducts. of the hydrophilic Further sodium purification acetate generated of allicin into was the based aqueous on thephase. differential DCM was partitioningremoved by rotary evaporation at RT at reduced pressure to yield an oily residue of allicin, unreacted DADS, of the constituents of the oily residue between n-hexane and an aqueous phase (two washes). and byproducts. Further purification of allicin was based on the differential partitioning of the Unreacted DADS and some allicin accumulated in the n-hexane phase, but allicin, which is more polar constituents of the oily residue between n-hexane and an aqueous phase (two washes). Unreacted thanDADS DADS, and concentrated some allicin to accumulated some extent in in the the n aqueous-hexane phase, phase. but The allicin, separation which method is more waspolar inefficient, than however,DADS, and concentrated allicin losses to some occurred extent at in this the stage.aqueou Finally,s phase. the The allicin-containing separation method aqueous was inefficient, phasewas partitionedhowever, against and allicin DCM losses to isolate occurred allicin at this and stage. dried Finally, over anhydrousthe allicin-containing CaSO4. Allicin aqueous was phase obtained was as an oilypartitioned residue against after evaporation DCM to isolate of the allicin DCM and under dried reducedover anhydrous pressure CaSO at RT.4. Allicin was obtained as anThis oily synthesis residue after consists evaporation of at least of the two DCM reaction under reduced steps. Firstly, pressure the at organicRT. peracid is formed by oxidationThis of thesynthesis organic consists acid by of Hat2 Oleast2. Secondly, two reaction DADS steps. is oxidizedFirstly, the by organic the peracid, peracid thus is formed regenerating by the parentoxidation organic of the organic acid. It acid has by been H2O reported2. Secondly, that DADS peracids, is oxidized such by as the performic peracid, thus and regenerating peracetic acids, the parent organic acid. It has been reported that peracids, such as performic and peracetic acids, are are adequately soluble in the organic phase [14], but DADS is immiscible with the aqueous H2O2 solutionadequately and the soluble reactions in the therefore organic phase take place[14], but in DADS a two phaseis immiscible system. with the aqueous H2O2 solution and the reactions therefore take place in a two phase system. In the optimized method described in this paper we used a formic acid catalyst instead of acetic In the optimized method described in this paper we used a formic acid catalyst instead of acetic acid, which enabled us to carry out the reaction at 0 ◦C under more controlled conditions and we acid, which enabled us to carry out the reaction at 0 °C under more controlled conditions and we systematicallysystematically varied varied the the concentrations concentrations of of the the reactants,reactants, while while following following the the progress progress of the of thereaction reaction usingusing HPLC. HPLC. Furthermore, Furthermore, we we developed developed aa silicasilica gel column chromatography chromatography protocol protocol for forallicin allicin purificationpurification which which avoided avoided the the losses losses associated associated withwith the original solvent solvent partitioning partitioning procedure. procedure. A reactionA reaction mechanism mechanism for for Stoll Stoll and and Seebeck’sSeebeck’s synt synthesishesis was was postulated postulated by byNikolic Nikolic et al. et [15] al. [15] proposingproposing oxidative oxidative cleavage cleavage of theof the S–S S–S bond bond in DADS in DADS by hydroxyl-radicalsby hydroxyl-radicals generated generated from from the the acidic H2Oacidic2 to give H2O allyl-sulfenic2 to give allyl-sulfenic acid which acid condenses which condenses to yield to allicin yield (Schemeallicin (Scheme1). In contrast, 1). In contrast, an alternate an mechanism,alternate namelymechanism, direct namely oxidation direct ofoxidation one of theof one S-atoms of the in S-atoms DADS withoutin DADS oxidativewithout oxidative cleavage of the S–Scleavage bond, of isthe also S–S plausible bond, is also (Scheme plausible1). (Scheme Here we 1). provide Here we data provide supporting data supporting an oxidative an oxidative cleavage mechanismcleavage andmechanism condensation and condensation of two sulfenic of two sulfenic acid molecules acid molecules to yield to yield allicin, allicin, but but without without a needa need for hydroxyl-radicals. for hydroxyl-radicals. SchemeScheme 1. Allicin 1. Allicin synthesis synthesis from from diallyl-disulfide diallyl-disulfide (DADS) through through oxidation oxidation by by a peracid a peracid generated generated withwith H2O H22inO2 thein the reaction reaction mixture.
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