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The Chemistry of Alliums

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (28 February 2017) | Viewed by 95370

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Prof. Dr. Alan J. Slusarenko

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Guest Editor

Head of the Plant Physiology Department at RWTH Aachen University, Aachen, Germany
Interests: resistance mechanisms of Arabidopsis to infection; natural products in plant protection
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Dr. Martin C. Gruhlke

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Society for Natural Product and Drug Research, 52070 Aachen, Germany
Interests: natural products; active ingredient; molecular biology; biochemistry; apoptosis
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Dear Colleagues,

The plant genus Allium has several wild and cultivated species that form an integral part of the human diet. Both raw in salads and cooked in the cuisines of many nations, Alliums are well known for their pungent odours and intensive flavours. The allyl group (CH₂=CH-CH₂-R) was named for the genus Allium and the chemistry of sulfur-containing molecules in these plants has long fascinated chemists, biochemists and biologists. Ranging from the lachrymatory factor of onions (propanethial S-oxide), through the intensely antimicrobial allicin from garlic, to the anticoagulant activity of ajoene and the anticancer effects of polysufanes; sulfur compounds from Alliums are often physiologically active and, therefore, of great medical and agricultural interest.

Furthermore, since the assimilation mechanisms plants use for SO₄⁻² may also be used for SeO₄⁻² or SeO₃⁻², the sulfur-rich Alliums are often good dietary sources of essential selenium, which is often deficient in the human diet and very important for antioxidative, protective enzymes such as glutathione peroxidase. This adds the dimension of the chemistry of selenium compounds to this Special Issue.

This Special Issue aims to attract contributions on all aspects of the chemistry and biochemistry of organic sulfur and selenium compounds in Alliums and their potential and actual applications in medicine and agriculture. Reviews and original research contributions are welcome.

Prof. Alan J. Slusarenko
Dr. Martin C.H. Gruhlke
Guest Editors

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Keywords

sulfur metabolism (anabolism and catabolism)
reactive sulfur species RSS
thiosulfinates, polysulfanes, polysulfides, sulfenic acids, allicin, allyl mercaptan, ajoene
cellular redox
cysteine
antioxidants
selenium, selenocysteine

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Editorial

Jump to: Research, Review

2 pages, 146 KiB

Open AccessEditorial

The Chemistry of Alliums

by Martin C. H. Gruhlke and Alan J. Slusarenko

Molecules 2018, 23(1), 143; https://doi.org/10.3390/molecules23010143 - 11 Jan 2018

Cited by 5 | Viewed by 4438

Abstract

Physiologically active sulfur-containing compounds produced by Allium spp. have long fascinated chemists, biochemists, and biologists.[...] Full article

(This article belongs to the Special Issue The Chemistry of Alliums)

Research

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4036 KiB

Open AccessArticle

Fluorinated Analogs of Organosulfur Compounds from Garlic (Allium sativum): Synthesis, Chemistry and Anti-Angiogenesis and Antithrombotic Studies

by Eric Block, Benjamin Bechand, Sivaji Gundala, Abith Vattekkatte, Kai Wang, Shaymaa S. Mousa, Kavitha Godugu, Murat Yalcin and Shaker A. Mousa

Molecules 2017, 22(12), 2081; https://doi.org/10.3390/molecules22122081 - 28 Nov 2017

Cited by 31 | Viewed by 10766 | Correction

Abstract

We describe the synthesis, reactivity, and antithrombotic and anti-angiogenesis activity of difluoroallicin (S-(2-fluoroallyl) 2-fluoroprop-2-ene-1-sulfinothioate) and S-2-fluoro-2-propenyl-l-cysteine, both easily prepared from commercially available 3-chloro-2-fluoroprop-1-ene, as well as the synthesis of 1,2-bis(2-fluoroallyl)disulfane, 5-fluoro-3-(1-fluorovinyl)-3,4-dihydro-1,2-dithiin, trifluoroajoene ((E,Z)-1-(2-fluoro-3-((2-fluoroallyl)sulfinyl)prop-1-en-1-yl)-2-(2-fluoroallyl)disulfane), and a bis(2-fluoroallyl)polysulfane mixture. All tested organosulfur compounds demonstrated effective inhibition of either FGF or VEG-mediated angiogenesis (anti-angiogenesis activity) in the chick chorioallantoic membrane (CAM) or the mouse Matrigel^® models. No embryo mortality was observed. Difluoroallicin demonstrated greater inhibition (p < 0.01) versus organosulfur compounds tested. Difluoroallicin demonstrated dose-dependent inhibition of angiogenesis in the mouse Matrigel^® model, with maximal inhibition at 0.01 mg/implant. Allicin and difluoroallicin showed an effective antiplatelet effect in suppressing platelet aggregation compared to other organosulfur compounds tested. In platelet/fibrin clotting (anti-coagulant activity), difluoroallicin showed concentration-dependent inhibition of clot strength compared to allicin and the other organosulfur compounds tested. Full article

(This article belongs to the Special Issue The Chemistry of Alliums)

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2743 KiB

Open AccessArticle

The Cytotoxicity of the Ajoene Analogue BisPMB in WHCO1 Oesophageal Cancer Cells Is Mediated by CHOP/GADD153

by Vuyolwethu Siyo, Georgia Schäfer, Roger Hunter, Andriy Grafov, Iryna Grafova, Martin Nieger, Arieh A. Katz, M. Iqbal Parker and Catherine H. Kaschula

Molecules 2017, 22(6), 892; https://doi.org/10.3390/molecules22060892 - 28 May 2017

Cited by 24 | Viewed by 5490

Abstract

Garlic is a food and medicinal plant that has been used in folk medicine since ancient times for its beneficial health effects, which include protection against cancer. Crushed garlic cloves contain an array of small sulfur-rich compounds such as ajoene. Ajoene is able to interfere with biological processes and is cytotoxic to cancer cells in the low micromolar range. BisPMB is a synthetic ajoene analogue that has been shown in our laboratory to have superior cytotoxicity to ajoene. In the current study we have performed a DNA microarray analysis of bisPMB-treated WHCO1 oesophageal cancer cells to identify pathways and processes that are affected by bisPMB. The most significantly enriched biological pathways as assessed by gene ontology, KEGG and ingenuity pathway analysis were those involving protein processing in the endoplasmic reticulum (ER) and the unfolded protein response. In support of these pathways, bisPMB was found to inhibit global protein synthesis and lead to increased levels of ubiquitinated proteins. BisPMB also induced alternate splicing of the transcription factor XBP-1; increased the expression of the ER stress sensor GRP78 and induced expression of the ER stress marker CHOP/GADD153. CHOP expression was found to be central to the cytotoxicity of bisPMB as its silencing with siRNA rendered the cells resistant to bisPMB. The MAPK proteins, JNK and ERK1/2 were activated following bisPMB treatment. However JNK activation was not critical in the cytotoxicity of bisPMB, and ERK1/2 activation was found to play a pro-survival role. Overall the ajoene analogue bisPMB appears to induce cytotoxicity in WHCO1 cells by activating the unfolded protein response through CHOP/GADD153. Full article

(This article belongs to the Special Issue The Chemistry of Alliums)

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2426 KiB

Open AccessArticle

An Optimized Facile Procedure to Synthesize and Purify Allicin

by Frank Albrecht, Roman Leontiev, Claus Jacob and Alan J. Slusarenko

Molecules 2017, 22(5), 770; https://doi.org/10.3390/molecules22050770 - 10 May 2017

Cited by 29 | Viewed by 8663

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. Full article

(This article belongs to the Special Issue The Chemistry of Alliums)

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2719 KiB

Open AccessArticle

Phytochemical Profiles and Antimicrobial Activities of Allium cepa Red cv. and A. sativum Subjected to Different Drying Methods: A Comparative MS-Based Metabolomics

by Mohamed A. Farag, Sara E. Ali, Rashad H. Hodaya, Hesham R. El-Seedi, Haider N. Sultani, Annegret Laub, Tarek F. Eissa, Fouad O. F. Abou-Zaid and Ludger A. Wessjohann

Molecules 2017, 22(5), 761; https://doi.org/10.3390/molecules22050761 - 8 May 2017

Cited by 97 | Viewed by 10782

Abstract

Plants of the Allium genus produce sulphur compounds that give them a characteristic (alliaceous) flavour and mediate for their medicinal use. In this study, the chemical composition and antimicrobial properties of Allium cepa red cv. and A. sativum in the context of three different drying processes were assessed using metabolomics. Bulbs were dried using either microwave, air drying, or freeze drying and further subjected to chemical analysis of their composition of volatile and non-volatile metabolites. Volatiles were collected using solid phase micro-extraction (SPME) coupled to gas chromatography–mass spectrometry (GC/MS) with 42 identified volatiles including 30 sulphur compounds, four nitriles, three aromatics, and three esters. Profiling of the polar non-volatile metabolites via ultra-performance liquid chromatography coupled to high resolution MS (UPLC/MS) annotated 51 metabolites including dipeptides, flavonoids, phenolic acids, and fatty acids. Major peaks in GC/MS or UPLC/MS contributing to the discrimination between A. sativum and A. cepa red cv. were assigned to sulphur compounds and flavonoids. Whereas sulphur conjugates amounted to the major forms in A. sativum, flavonoids predominated in the chemical composition of A. cepa red cv. With regard to drying impact on Allium metabolites, notable and clear separations among specimens were revealed using principal component analysis (PCA). The PCA scores plot of the UPLC/MS dataset showed closer metabolite composition of microwave dried specimens to freeze dried ones, and distant from air dried bulbs, observed in both A. cepa and A. sativum. Compared to GC/MS, the UPLC/MS derived PCA model was more consistent and better in assessing the impact of drying on Allium metabolism. A phthalate derivative was found exclusively in a commercial garlic preparation via GC/MS, of yet unknown origin. The freeze dried samples of both Allium species exhibited stronger antimicrobial activities compared to dried specimens with A. sativum being in general more active than A. cepa red cv. Full article

(This article belongs to the Special Issue The Chemistry of Alliums)

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2861 KiB

Open AccessArticle

Attenuation of Bleomycin-Induced Pulmonary Fibrosis in Rats with S-Allyl Cysteine

by Takuma Tsukioka, Shigekazu Takemura, Yukiko Minamiyama, Shinjiro Mizuguchi, Michihito Toda and Shigeru Okada

Molecules 2017, 22(4), 543; https://doi.org/10.3390/molecules22040543 - 29 Mar 2017

Cited by 13 | Viewed by 6452

Abstract

Pulmonary fibrosis is a complex disease with high mortality and morbidity. As there are currently no effective treatments, development of new strategies is essential for improving therapeutic outcomes. S-allyl cysteine (SAC) is a constituent of aged garlic extract that has demonstrated efficacy as an antioxidant and anti-inflammatory agent. The current study examines the effects of SAC on pulmonary fibrosis induced by a single intratracheal instillation of bleomycin (2.5 mg/kg). SAC was administered to rats as 0.15% SAC-containing diet from seven days prior to instillation up until the conclusion of the experiment (14 days post-instillation). SAC significantly reduced collagen mRNA expression and protein deposition (33.3 ± 2.7 μg/mg and 28.2 ± 2.1 μg/mg tissue in vehicle- and SAC-treated rats, respectively), and decreased fibrotic area, as assessed histologically. In the rats’ lungs, SAC also attenuated the increased expression of transforming growth factor-β1 (TGF-β1), a central regulator of myofibroblast recruitment, activation, and differentiation. While bleomycin instillation increased the number of myofibroblasts within the lung mesenchymal area, this change was significantly reduced by SAC treatment. SAC may exert efficacy as an anti-fibrotic by attenuating myofibroblast differentiation through TGF-β1-mediated fibroproliferative processes. Thus, our results indicate SAC may be useful for the prevention or treatment of pulmonary fibrosis. Full article

(This article belongs to the Special Issue The Chemistry of Alliums)

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885 KiB

Open AccessArticle

Effect of the Aged Garlic Extract on Cardiovascular Function in Metabolic Syndrome Rats

by Israel Pérez-Torres, Juan Carlos Torres-Narváez, José Pedraza-Chaverri, María Esther Rubio-Ruiz, Eulises Díaz-Díaz, Leonardo Del Valle-Mondragón, Raúl Martínez-Memije, Elvira Varela López and Verónica Guarner-Lans

Molecules 2016, 21(11), 1425; https://doi.org/10.3390/molecules21111425 - 26 Oct 2016

Cited by 35 | Viewed by 8923

Abstract

The antioxidant properties of aged garlic extract (AGE) on cardiovascular functioning (CF) in metabolic syndrome (MS) remains poorly studied. Here we study the AGE effects on CF in a rat model of MS. Control rats plus saline solution (C + SS), MS rats (30% sucrose in drinking water from weaning) plus saline solution (MS + SS), control rats receiving AGE (C + AGE 125 mg/Kg/12 h) and MS rats with AGE (MS + AGE) were studied. MS + SS had increased triglycerides, systolic blood pressure, insulin, leptin, HOMA index, and advanced glycation end products. AGE returned their levels to control values (p < 0.01). Cholesterol was decreased by AGE (p = 0.05). Glutathion and GPx activity were reduced in MS + SS rats and increased with AGE (p = 0.05). Lipid peroxidation was increased in MS + SS and AGE reduced it (p = 0.001). Vascular functioning was deteriorated by MS (increased vasocontraction and reduced vasodilation) and AGE improved it (p = 0.001). Coronary vascular resistance was increased in MS rats and AGE decreased it (p = 0.001). Cardiac performance was not modified by MS but AGE increased it. NO measured in the perfusate liquid from the heart and serum citrulline, nitrites/nitrates were decreased in MS and AGE increased them (p < 0.01). In conclusion, AGE reduces MS-induced cardiovascular risk, through its anti-oxidant properties. Full article

(This article belongs to the Special Issue The Chemistry of Alliums)

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Review

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684 KiB

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Physicochemical Properties, Biological Activity, Health Benefits, and General Limitations of Aged Black Garlic: A Review

by Ji Hyeon Ryu and Dawon Kang

Molecules 2017, 22(6), 919; https://doi.org/10.3390/molecules22060919 - 1 Jun 2017

Cited by 117 | Viewed by 20681

Abstract

Garlic (Allium sativum) has been used as a medicinal food since ancient times. However, some people are reluctant to ingest raw garlic due to its unpleasant odor and taste. Therefore, many types of garlic preparations have been developed to reduce these attributes without losing biological functions. Aged black garlic (ABG) is a garlic preparation with a sweet and sour taste and no strong odor. It has recently been introduced to Asian markets as a functional food. Extensive in vitro and in vivo studies have demonstrated that ABG has a variety of biological functions such as antioxidant, anti-inflammatory, anti-cancer, anti-obesity, anti-diabetic, anti-allergic, cardioprotective, and hepatoprotective effects. Recent studies have compared the biological activity and function of ABG to those of raw garlic. ABG shows lower anti-inflammatory, anti-coagulation, immunomodulatory, and anti-allergic effects compared to raw garlic. This paper reviews the physicochemical properties, biological activity, health benefits, adverse effects, and general limitations of ABG. Full article

(This article belongs to the Special Issue The Chemistry of Alliums)

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1778 KiB

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Chemical and Biological Properties of S-1-Propenyl-ʟ-Cysteine in Aged Garlic Extract

by Yukihioro Kodera, Mitsuyasu Ushijima, Hirotaka Amano, Jun-ichiro Suzuki and Toshiaki Matsutomo

Molecules 2017, 22(4), 570; https://doi.org/10.3390/molecules22040570 - 31 Mar 2017

Cited by 59 | Viewed by 9663

Abstract

S-1-Propenyl-ʟ-cysteine (S1PC) is a stereoisomer of S-1-Propenyl-ʟ-cysteine (SAC), an important sulfur-containing amino acid that plays a role for the beneficial pharmacological effects of aged garlic extract (AGE). The existence of S1PC in garlic preparations has been known since the 1960’s. However, there was no report regarding the biological and/or pharmacological activity of S1PC until 2016. Recently, we performed a series of studies to examine the chemical, biological, pharmacological and pharmacokinetic properties of S1PC, and obtained some interesting results. S1PC existed only in trace amounts in raw garlic, but its concentration increased almost up to the level similar of SAC through aging process of AGE. S1PC showed immunomodulatory effects in vitro and in vivo, and reduced blood pressure in a hypertensive animal model. A pharmacokinetic study revealed that S1PC was readily absorbed after oral administration in rats and dogs with bioavailability of 88–100%. Additionally, S1PC had little inhibitory influence on human cytochrome P450 activities, even at a concentration of 1 mM. Based on these findings, S1PC was suggested to be another important, pharmacologically active and safe component of AGE similar to SAC. In this review, we highlight some results from recent studies on S1PC and discuss the potential medicinal value of S1PC. Full article

(This article belongs to the Special Issue The Chemistry of Alliums)

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1461 KiB

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Selenium and Sulfur to Produce Allium Functional Crops

by Susana González-Morales, Fabián Pérez-Labrada, Ema Laura García-Enciso, Paola Leija-Martínez, Julia Medrano-Macías, Irma Esther Dávila-Rangel, Antonio Juárez-Maldonado, Erika Nohemí Rivas-Martínez and Adalberto Benavides-Mendoza

Molecules 2017, 22(4), 558; https://doi.org/10.3390/molecules22040558 - 30 Mar 2017

Cited by 59 | Viewed by 8543

Abstract

Selenium is an element that must be considered in the nutrition of certain crops since its use allows the obtaining of biofortified crops with a positive impact on human health. The objective of this review is to present the information on the use of Se and S in the cultivation of plants of the genus Allium. The main proposal is to use Allium as specialist plants for biofortification with Se and S, considering the natural ability to accumulate both elements in different phytochemicals, which promotes the functional value of Allium. In spite of this, in the agricultural production of these species, the addition of sulfur is not realized to obtain functional foods and plants more resistant; it is only sought to cover the necessary requirements for growth. On the other hand, selenium does not appear in the agronomic management plans of most of the producers. Including S and Se fertilization as part of agronomic management can substantially improve Allium crop production. Allium species may be suitable to carry out biofortification with Se; this practice can be combined with the intensive use of S to obtain crops with higher production and sensory, nutritional, and functional quality. Full article

(This article belongs to the Special Issue The Chemistry of Alliums)

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