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Special Issue "The Chemistry of Alliums"

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

Deadline for manuscript submissions: closed (28 February 2017)

Special Issue Editors

Guest Editor
Prof. Alan J. Slusarenko

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

Plant Physiology Department at RWTH Aachen University, Aachen, Germany
Website | E-Mail
Interests: molecular mechanisms of redox-active compounds in fungi; plants and animal cell lines with a certain focus on allicin; sulfur-containing natural product from garlic

Special Issue Information

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

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

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

Published Papers (8 papers)

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Research

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Open AccessArticle The Cytotoxicity of the Ajoene Analogue BisPMB in WHCO1 Oesophageal Cancer Cells Is Mediated by CHOP/GADD153
Molecules 2017, 22(6), 892; doi:10.3390/molecules22060892
Received: 21 March 2017 / Revised: 23 May 2017 / Accepted: 24 May 2017 / Published: 28 May 2017
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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
[...] Read more.
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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Open AccessArticle An Optimized Facile Procedure to Synthesize and Purify Allicin
Molecules 2017, 22(5), 770; doi:10.3390/molecules22050770
Received: 1 March 2017 / Revised: 28 April 2017 / Accepted: 5 May 2017 / Published: 10 May 2017
Cited by 1 | PDF Full-text (2426 KB) | HTML Full-text | XML Full-text
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
[...] Read more.
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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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
Molecules 2017, 22(5), 761; doi:10.3390/molecules22050761
Received: 28 February 2017 / Revised: 17 April 2017 / Accepted: 5 May 2017 / Published: 8 May 2017
PDF Full-text (2719 KB) | HTML Full-text | XML Full-text | Supplementary Files
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
[...] Read more.
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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Open AccessArticle Attenuation of Bleomycin-Induced Pulmonary Fibrosis in Rats with S-Allyl Cysteine
Molecules 2017, 22(4), 543; doi:10.3390/molecules22040543
Received: 14 February 2017 / Revised: 20 March 2017 / Accepted: 24 March 2017 / Published: 29 March 2017
Cited by 1 | PDF Full-text (2861 KB) | HTML Full-text | XML Full-text
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
[...] Read more.
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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Open AccessArticle Effect of the Aged Garlic Extract on Cardiovascular Function in Metabolic Syndrome Rats
Molecules 2016, 21(11), 1425; doi:10.3390/molecules21111425
Received: 29 September 2016 / Revised: 16 October 2016 / Accepted: 21 October 2016 / Published: 26 October 2016
Cited by 2 | PDF Full-text (885 KB) | HTML Full-text | XML Full-text
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
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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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Open AccessReview Physicochemical Properties, Biological Activity, Health Benefits, and General Limitations of Aged Black Garlic: A Review
Molecules 2017, 22(6), 919; doi:10.3390/molecules22060919
Received: 30 March 2017 / Revised: 25 May 2017 / Accepted: 29 May 2017 / Published: 1 June 2017
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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
[...] Read more.
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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Open AccessReview Chemical and Biological Properties of S-1-Propenyl-ʟ-Cysteine in Aged Garlic Extract
Molecules 2017, 22(4), 570; doi:10.3390/molecules22040570
Received: 7 February 2017 / Revised: 27 March 2017 / Accepted: 27 March 2017 / Published: 31 March 2017
Cited by 1 | PDF Full-text (1778 KB) | HTML Full-text | XML Full-text | Supplementary Files
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
[...] Read more.
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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Open AccessReview Selenium and Sulfur to Produce Allium Functional Crops
Molecules 2017, 22(4), 558; doi:10.3390/molecules22040558
Received: 26 February 2017 / Revised: 27 March 2017 / Accepted: 27 March 2017 / Published: 30 March 2017
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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
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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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