Literature DB >> 31414826

Discovery and Total Synthesis of Doscadenamide A: A Quorum Sensing Signaling Molecule from a Marine Cyanobacterium.

Xiao Liang1,2, Susan Matthew1, Qi-Yin Chen1,2, Jason C Kwan1, Valerie J Paul3, Hendrik Luesch1,2.   

Abstract

Quorum sensing (QS) plays a critical role in the regulation of bacterial pathogenesis. Doscadenamide A (1a) was isolated from a marine cyanobacterium, its structure elucidated by NMR, and its activity linked to QS induction. The total synthesis of 1a was developed, and the absolute configuration confirmed through comparison of the isolated natural product with synthetic diastereomers. Our preliminary investigation indicated that 1a could activate QS signaling in a LasR-dependent manner.

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Year:  2019        PMID： 31414826      PMCID： PMC7325281          DOI： 10.1021/acs.orglett.9b02525

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  24 in total

1.  Small molecule inhibitors of bacterial quorum sensing and biofilm formation.

Authors:  Grant D Geske; Rachel J Wezeman; Adam P Siegel; Helen E Blackwell
Journal:  J Am Chem Soc       Date:  2005-09-21       Impact factor: 15.419

Review 2.  Biological targets and mechanisms of action of natural products from marine cyanobacteria.

Authors:  Lilibeth A Salvador-Reyes; Hendrik Luesch
Journal:  Nat Prod Rep       Date:  2015-03       Impact factor: 13.423

3.  Apratyramide, a Marine-Derived Peptidic Stimulator of VEGF-A and Other Growth Factors with Potential Application in Wound Healing.

Authors:  Weijing Cai; Lilibeth A Salvador-Reyes; Wei Zhang; Qi-Yin Chen; Susan Matthew; Ranjala Ratnayake; Soo Jung Seo; Simon Dolles; Daniel J Gibson; Valerie J Paul; Hendrik Luesch
Journal:  ACS Chem Biol       Date:  2017-12-05       Impact factor: 5.100

4.  Sesterterpenoids and diterpenoids of the wax excreted by a scale insect, Ceroplastes pseudoceriferus.

Authors:  M Toki; T Ooi; T Kusumi
Journal:  J Nat Prod       Date:  1999-11       Impact factor: 4.050

5.  Lyngbyoic acid, a "tagged" fatty acid from a marine cyanobacterium, disrupts quorum sensing in Pseudomonas aeruginosa.

Authors:  Jason Christopher Kwan; Theresa Meickle; Dheran Ladwa; Max Teplitski; Valerie Paul; Hendrik Luesch
Journal:  Mol Biosyst       Date:  2011-01-24

6.  Dipeptide analogues containing 4-ethoxy-3-pyrrolin-2-ones.

Authors:  Masood Hosseini; Henriette Kringelum; Anthony Murray; Janne E Tønder
Journal:  Org Lett       Date:  2006-05-11       Impact factor: 6.005

7.  Total structure determination of apratoxin A, a potent novel cytotoxin from the marine cyanobacterium Lyngbya majuscula.

Authors:  H Luesch; W Y Yoshida; R E Moore; V J Paul; T H Corbett
Journal:  J Am Chem Soc       Date:  2001-06-13       Impact factor: 15.419

8.  Molecular basis for the recognition of structurally distinct autoinducer mimics by the Pseudomonas aeruginosa LasR quorum-sensing signaling receptor.

Authors:  Yaozhong Zou; Satish K Nair
Journal:  Chem Biol       Date:  2009-09-25

9.  Modular strategies for structure and function employed by marine cyanobacteria: characterization and synthesis of pitinoic acids.

Authors:  Rana Montaser; Valerie J Paul; Hendrik Luesch
Journal:  Org Lett       Date:  2013-08-05       Impact factor: 6.005

Review 10.  Quorum quenching agents: resources for antivirulence therapy.

Authors:  Kaihao Tang; Xiao-Hua Zhang
Journal:  Mar Drugs       Date:  2014-05-30       Impact factor: 5.118
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  3 in total

1.  Bifunctional Doscadenamides Activate Quorum Sensing in Gram-Negative Bacteria and Synergize with TRAIL to Induce Apoptosis in Cancer Cells.

Authors:  Xiao Liang; Qi-Yin Chen; Gustavo M Seabra; Susan Matthew; Jason C Kwan; Chenglong Li; Valerie J Paul; Hendrik Luesch
Journal:  J Nat Prod       Date:  2021-01-22       Impact factor: 4.050

2.  Applying a Chemogeographic Strategy for Natural Product Discovery from the Marine Cyanobacterium Moorena bouillonii.

Authors:  Christopher A Leber; C Benjamin Naman; Lena Keller; Jehad Almaliti; Eduardo J E Caro-Diaz; Evgenia Glukhov; Valsamma Joseph; T P Sajeevan; Andres Joshua Reyes; Jason S Biggs; Te Li; Ye Yuan; Shan He; Xiaojun Yan; William H Gerwick
Journal:  Mar Drugs       Date:  2020-10-14       Impact factor: 5.118

3.  Metabolomic Characterization of a cf. Neolyngbya Cyanobacterium from the South China Sea Reveals Wenchangamide A, a Lipopeptide with In Vitro Apoptotic Potential in Colon Cancer Cells.

Authors:  Lijian Ding; Rinat Bar-Shalom; Dikla Aharonovich; Naoaki Kurisawa; Gaurav Patial; Shuang Li; Shan He; Xiaojun Yan; Arihiro Iwasaki; Kiyotake Suenaga; Chengcong Zhu; Haixi Luo; Fuli Tian; Fuad Fares; C Benjamin Naman; Tal Luzzatto-Knaan
Journal:  Mar Drugs       Date:  2021-07-16       Impact factor: 5.118
  3 in total

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