For Publishers
DiscoveryMetadataPeer reviewHostingPublishing
For Researchers
JoinPublishReviewCollect
Register
Blog
About
Search
Advanced search
My ScienceOpen
Search
For Publishers
For Researchers
Blog
About
Inviting an author to review:
Transforming consumers' intention to purchase green products: Role of social media
Find an author and click ‘Invite to review selected article’ near their name.
Search for authorsSearch for similar articles
7
views
16
references
 Top references
cited by
8
    
0 reviews
 Review
0
comments
 Comment
0
recommends
+1 Recommend
0 collections
    0
    shares
      261
      similar
       All similar
      • Record: found
      • Abstract: found
      • Article: found
      Is Open Access

      Short Total Synthesis of Ajoene

      brief-report

      Read this article at

      ScienceOpenPublisherPMC
      Bookmark
          There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

          Abstract

          We describe a short total synthesis of ajoene, a major biologically active constituent of garlic. The instability of allicin as the only other known alternative starting material has led to the development of a reliable procedure for the synthesis of ajoene from simple building blocks that is also suitable for upscale operations.

          Related collections

          Most cited references16

          • Record: found
          • Abstract: found
          • Article: not found

          Ajoene, a sulfur-rich molecule from garlic, inhibits genes controlled by quorum sensing.

          Tim Holm Jakobsen, Maria van Gennip, Richard Kerry Phipps … (2012)
          In relation to emerging multiresistant bacteria, development of antimicrobials and new treatment strategies of infections should be expected to become a high-priority research area. Quorum sensing (QS), a communication system used by pathogenic bacteria like Pseudomonas aeruginosa to synchronize the expression of specific genes involved in pathogenicity, is a possible drug target. Previous in vitro and in vivo studies revealed a significant inhibition of P. aeruginosa QS by crude garlic extract. By bioassay-guided fractionation of garlic extracts, we determined the primary QS inhibitor present in garlic to be ajoene, a sulfur-containing compound with potential as an antipathogenic drug. By comprehensive in vitro and in vivo studies, the effect of synthetic ajoene toward P. aeruginosa was elucidated. DNA microarray studies of ajoene-treated P. aeruginosa cultures revealed a concentration-dependent attenuation of a few but central QS-controlled virulence factors, including rhamnolipid. Furthermore, ajoene treatment of in vitro biofilms demonstrated a clear synergistic, antimicrobial effect with tobramycin on biofilm killing and a cease in lytic necrosis of polymorphonuclear leukocytes. Furthermore, in a mouse model of pulmonary infection, a significant clearing of infecting P. aeruginosa was detected in ajoene-treated mice compared to a nontreated control group. This study adds to the list of examples demonstrating the potential of QS-interfering compounds in the treatment of bacterial infections.
          Article 0 comments Cited 126 times – based on 0 reviews     Review now
            Bookmark
            • Record: found
            • Abstract: found
            • Article: found
            Is Open Access

            A broad range quorum sensing inhibitor working through sRNA inhibition

            Tim H Jakobsen, Anders N. Warming, Rebecca Vejborg … (2017)
            For the last decade, chemical control of bacterial virulence has received considerable attention. Ajoene, a sulfur-rich molecule from garlic has been shown to reduce expression of key quorum sensing regulated virulence factors in the opportunistic pathogen Pseudomonas aeruginosa. Here we show that the repressing effect of ajoene on quorum sensing occurs by inhibition of small regulatory RNAs (sRNA) in P. aeruginosa as well as in Staphylococcus aureus, another important human pathogen that employs quorum sensing to control virulence gene expression. Using various reporter constructs, we found that ajoene lowered expression of the sRNAs RsmY and RsmZ in P. aeruginosa and the small dual-function regulatory RNA, RNAIII in S. aureus, that controls expression of key virulence factors. We confirmed the modulation of RNAIII by RNA sequencing and found that the expression of many QS regulated genes encoding virulence factors such as hemolysins and proteases were lowered in the presence of ajoene in S. aureus. Importantly, our findings show that sRNAs across bacterial species potentially may qualify as targets of anti-virulence therapy and that ajoene could be a lead structure in search of broad-spectrum compounds transcending the Gram negative-positive borderline.
            Article 0 comments Cited 31 times – based on 0 reviews     Review now
              Bookmark
              • Record: found
              • Abstract: not found
              • Article: not found

              The chemistry of alkyl thiosulfinate esters. 9. Antithrombotic organosulfur compounds from garlic: structural, mechanistic, and synthetic studies

              James L. Catalfamo, Mahendra Jain, Rafael Apitz-Castro … (1986)
              Article 0 comments Cited 23 times – based on 0 reviews     Review now
                Bookmark
                All references

                Author and article information

                Contributors
                Prof. Dr. Thomas Wirth:
                ORCID: http://orcid.org/0000-0002-8990-0667
                wirth@cf.ac.uk
                Journal
                Journal ID (nlm-ta): Angew Chem Int Ed Engl
                Journal ID (iso-abbrev): Angew. Chem. Int. Ed. Engl
                Journal ID (doi): 10.1002/(ISSN)1521-3773
                Journal ID (publisher-id): ANIE
                Title: Angewandte Chemie (International Ed. in English)
                Publisher: John Wiley and Sons Inc. (Hoboken )
                ISSN (Print): 1433-7851
                ISSN (Electronic): 1521-3773
                Publication date (Electronic): 19 August 2018
                Publication date (Print): 17 September 2018
                Volume: 57
                Issue: 38 ( doiID: 10.1002/anie.v57.38 )
                Pages: 12290-12293
                Affiliations
                [ 1 ] School of Chemistry Cardiff University Park Place, Main Building Cardiff CF10 3AT UK
                [ 2 ] Neem Biotech Roseheyworth Business Park North Abertillery NP13 1SX UK
                Author information
                http://orcid.org/0000-0002-8990-0667
                Article
                Publisher ID: ANIE201808605
                DOI: 10.1002/anie.201808605
                PMC ID: 6221122
                PubMed ID: 30079981
                SO-VID: deaa732a-5c13-4e3d-990d-8461a0f8b7f5
                Copyright © © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
                License:

                This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

                History
                Date received : 26 July 2018
                Page count
                Figures: 7, Tables: 1, References: 26, Pages: 4, Words: 0
                Funding
                Funded by: Engineering and Physical Sciences Research Council
                Categories
                Subject: Communication
                Subject: Communications
                Subject: Natural Product Synthesis | Hot Paper
                Custom metadata
                source-schema-version-number 2.0
                component-id anie201808605
                cover-date September 17, 2018
                details-of-publishers-convertor Converter:WILEY_ML3GV2_TO_NLMPMC version:version=5.5.1 mode:remove_FC converted:07.11.2018

                ScienceOpen disciplines: Chemistry
                Keywords: ajoene,allicin,garlic,organosulfur compounds,selenoxide elimination
                Data availability:
                ScienceOpen disciplines: Chemistry
                Keywords: ajoene, allicin, garlic, organosulfur compounds, selenoxide elimination

                Comments

                Comment on this article

                scite_

                Similar content261

                See all similar

                Cited by8

                See all cited by