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An Appraisal of Developments in Allium Sulfur Chemistry: Expanding the Pharmacopeia of Garlic

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An Appraisal of Developments in Allium Sulfur Chemistry: Expanding the Pharmacopeia of Garlic molecules Review An Appraisal of Developments in Allium Sulfur Chemistry: Expanding the Pharmacopeia of Garlic Peter Rose 1,2,*, Philip Keith Moore 3, Matthew Whiteman 4 and Yi-Zhun Zhu 2 1 School of Biosciences, University of Nottingham, Loughborough, Leicestershire LE12 5RD, UK 2 School of Pharmacy and State key Lab. of Quality Research in Chinese Medicine, Macau University of Science and Technology, Macau, China; [email protected] 3 Department of Pharmacology, Yong Loo Lin School of Medicine, National University of Singapore, Singapore 117597, Singapore; [email protected] 4 Medical School Building, St Luke’s Campus, Magdalen Road, Exeter EX1 2LU, UK; [email protected] * Correspondence: [email protected] Academic Editor: Claus Jacob Received: 23 August 2019; Accepted: 30 October 2019; Published: 5 November 2019 Abstract: Alliums and allied plant species are rich sources of sulfur compounds that have effects on vascular homeostasis and the control of metabolic systems linked to nutrient metabolism in mammals. In view of the multiple biological effects ascribed to these sulfur molecules, researchers are now using these compounds as inspiration for the synthesis and development of novel sulfur-based therapeutics. This research has led to the chemical synthesis and biological assessment of a diverse array of sulfur compounds representative of derivatives of S-alkenyl-l-cysteine sulfoxides, thiosulfinates, ajoene molecules, sulfides, and S-allylcysteine. Many of these synthetic derivatives have potent antimicrobial and anticancer properties when tested in preclinical models of disease. Therefore, the current review provides an overview of advances in the development and biological assessment of synthetic analogs of allium-derived sulfur compounds. Keywords: allium; anticancer; sulfur compounds; gaseous mediators; hydrogen sulfide; garlic 1. Introduction Approximately 700 plant species are known to contain S-alk(en)yl-l-cysteine sulfoxides (ACSOs), including many edibles like allium and brassica vegetables (Table1). Popularity stems from their distinctive flavors, produced during the breakdown of each respective ACSOs [1,2]. As such, changes to the composition and quantities of each ACSO determines the odor, flavor variation, and biological activities ascribed to many plants containing these sulfur storage compounds [3]. At present, four major and two minor ACSOs exist, and these act as progenitor molecules in the production of other sulfur compounds like the lachrymatory factor, propanethial S-oxide and the antimicrobial compound allicin [3]. An additional 50+ sulfur compounds, including thiosulfinates, cysteine, and sulfides derivatives can also occur in allium tissue following preparation, and many of these compounds possess some level of biological activity in mammalian cells and tissue [4]. Indeed, researchers have shown crude allium-derived plant extracts as well as isolated sulfur compounds such as S-allylcysteine, diallyl disulfide, allicin, 1,2-vinyldithiin, 3-vinyldithiin, and ajoene can induce a range of physiological and biochemical changes in mammalian systems [5]. For example, several cellular targets are reported to be susceptible to sulfur compound treatment, including proinflammatory transcription factor nuclear factor-kappa beta (NF-κB) [6,7], various kinases, including p38 mitogen-activated protein kinase (p38 MAPK) [8], c-JunNH2-terminal kinase (JNK) [9], extracellular signal-regulated kinase (ERK) [10], and phosphoinositide 3-kinase-protein kinase B (PI-3K-Akt) [11]. Other cellular proteins, like nuclear Molecules 2019, 24, 4006; doi:10.3390/molecules24214006 www.mdpi.com/journal/molecules Molecules 2019, 24, x FOR PEER REVIEW 2 of 17 Molecules3K-Akt) 2019 [11]., 24 Other, x FOR cellularPEER REVIEW protei ns, like nuclear factor erythroid 2-related factor 2 (Nrf-2) [12–14],2 of 17 p53 [15,16], AMP-activated protein kinase [17,18], proliferator-activated receptor γ [19], and NAD- 3K-Akt)dependent [11]. deacetylase Other cellular sirtuin-1 protei ns,(SIRT1) like nuclear[20] are factor also erythroidtargets of 2-related allium-derived factor 2 (Nrf-2)sulfur [12–14],species. p53Consequently,Molecules [15,16], 2019 , AMP-activated24, manyx FOR PEER sulfur REVIEW moleculesprotein kinase have [17,18], been repo proliferator-activatedrted to have anticancer receptor properties γ [19], [21–24], and NAD-2 of are 17 dependentanti-inflammatory deacetylase [7,25–27], sirtuin-1 act as (SIRT1) cytoprotective [20] are agen alsots [28,29],targets functionof allium-derived as inhibitors sulfur of metastasis species. Consequently,[30,31],3K-Akt) and[11]. alter Other many lipid cellular sulfur metabolism moleculesproteins, [32,33]. like have nuclear beenAdditionally, repo factorrted erythroid tomolecules have anticancer2-related like diallyl factor properties trisulfide2 (Nrf-2) [21–24], [12–14],(DATS) are Molecules 2019, 24, x FOR PEER REVIEW 2 of 17 anti-inflammatoryreleasep53 [15,16], hydrogen AMP-activated sulfide [7,25–27], gas protein (Hact2 S)as incytoprotective kinase the presence [17,18], agenof proliferator-activated glutathionets [28,29], andfunction cysteine receptor as inhibitors [34]. γThe [19], liberatedof andmetastasis NAD- H2S [30,31],actsdependent as aand gaseous deacetylasealter signalinglipid metabolismsirtuin-1 molecule (SIRT1) [32,33]. in mammalian [20] Additionally, are al cellsso targets withmolecules potential of allium-derived like pharmacological diallyl trisulfide sulfur effects species.(DATS) in Molecules3K-Akt) 2019 [11]., 24 Other, x FOR cellularPEER REVIEW protei ns, like nuclear factor erythroid 2-related factor 2 (Nrf-2) [12–14],2 of 17 releasehumansConsequently, hydrogen [35,36]. many This sulfide propsulfur gaserty molecules (H may2S) in contribute the have presence been to therepo of glutathionebiologicalrted to have effects and anticancer cysteine attributed [34].properties to The DATS liberated [21–24], and, more H are2S p53 [15,16], AMP-activated protein kinase [17,18], proliferator-activated receptor γ [19], and NAD- actswidely,anti-inflammatory as a other gaseous allium-derived signaling [7,25–27], molecule act sulfur as cytoprotective species in mammalian [37]. 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