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Title: Precursor-Directed Combinatorial Biosynthesis of Cinnamoyl, Dihydrocinnamoyl, and Benzoyl Anthranilates in Saccharomyces cerevisiae

Abstract

© 2015 Eudes et al. This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Biological synthesis of pharmaceuticals and biochemicals offers an environmentally friendly alternative to conventional chemical synthesis. These alternative methods require the design of metabolic pathways and the identification of enzymes exhibiting adequate activities. Cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates are natural metabolites which possess beneficial activities for human health, and the search is expanding for novel derivatives that might have enhanced biological activity. For example, biosynthesis in Dianthus caryophyllus is catalyzed by hydroxycinnamoyl/benzoyl-CoA:anthranilate N-hydroxycinnamoyl/ benzoyltransferase (HCBT), which couples hydroxycinnamoyl-CoAs and benzoyl-CoAs to anthranilate. We recently demonstrated the potential of using yeast (Saccharomyces cerevisiae) for the biological production of a few cinnamoyl anthranilates by heterologous co-expression of 4-coumaroyl:CoA ligase from Arabidopsis thaliana (4CL5) and HCBT. Here we report that, by exploiting the substrate flexibility of both 4CL5 and HCBT, we achieved rapid biosynthesis of more than 160 cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates in yeast upon feeding with both natural and non-natural cinnamates, dihydrocinnamates, benzoates, and anthranilates. Our results demonstrate the use of enzyme promiscuitymore » in biological synthesis to achieve high chemical diversity within a defined class of molecules. This work also points to the potential for the combinatorial biosynthesis of diverse and valuable cinnamoylated, dihydrocinnamoylated, and benzoylated products by using the versatile biological enzyme 4CL5 along with characterized cinnamoyl- CoA- and benzoyl-CoA-utilizing transferases.« less

Authors:
 [1];  [2];  [1];  [1];  [1];  [3];  [1]
+ Show Author Affiliations
  1. Joint BioEnergy Inst., Emeryville, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
  2. Joint BioEnergy Inst., Emeryville, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); San Francisco State Univ., CA (United States)
  3. Joint BioEnergy Inst., Emeryville, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Univ. of California, Berkeley, CA (United States)
Publication Date:
Research Org.:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER)
OSTI Identifier:
1256953
Alternate Identifier(s):
OSTI ID: 1378578
Grant/Contract Number:  
AC02- 05CH11231; AC02-05CH11231
Resource Type:
Accepted Manuscript
Journal Name:
PLoS ONE
Additional Journal Information:
Journal Volume: 10; Journal Issue: 10; Journal ID: ISSN 1932-6203
Publisher:
Public Library of Science
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES

Citation Formats

Eudes, Aymerick, Teixeira Benites, Veronica, Wang, George, Baidoo, Edward E. K., Lee, Taek Soon, Keasling, Jay D., and Loqué, Dominique. Precursor-Directed Combinatorial Biosynthesis of Cinnamoyl, Dihydrocinnamoyl, and Benzoyl Anthranilates in Saccharomyces cerevisiae. United States: N. p., 2015. Web. doi:10.1371/journal.pone.0138972.
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Eudes, Aymerick, Teixeira Benites, Veronica, Wang, George, Baidoo, Edward E. K., Lee, Taek Soon, Keasling, Jay D., & Loqué, Dominique. Precursor-Directed Combinatorial Biosynthesis of Cinnamoyl, Dihydrocinnamoyl, and Benzoyl Anthranilates in Saccharomyces cerevisiae. United States. https://doi.org/10.1371/journal.pone.0138972
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Eudes, Aymerick, Teixeira Benites, Veronica, Wang, George, Baidoo, Edward E. K., Lee, Taek Soon, Keasling, Jay D., and Loqué, Dominique. Fri . "Precursor-Directed Combinatorial Biosynthesis of Cinnamoyl, Dihydrocinnamoyl, and Benzoyl Anthranilates in Saccharomyces cerevisiae". United States. https://doi.org/10.1371/journal.pone.0138972. https://www.osti.gov/servlets/purl/1256953.
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@article{osti_1256953,
title = {Precursor-Directed Combinatorial Biosynthesis of Cinnamoyl, Dihydrocinnamoyl, and Benzoyl Anthranilates in Saccharomyces cerevisiae},
author = {Eudes, Aymerick and Teixeira Benites, Veronica and Wang, George and Baidoo, Edward E. K. and Lee, Taek Soon and Keasling, Jay D. and Loqué, Dominique},
abstractNote = {© 2015 Eudes et al. This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Biological synthesis of pharmaceuticals and biochemicals offers an environmentally friendly alternative to conventional chemical synthesis. These alternative methods require the design of metabolic pathways and the identification of enzymes exhibiting adequate activities. Cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates are natural metabolites which possess beneficial activities for human health, and the search is expanding for novel derivatives that might have enhanced biological activity. For example, biosynthesis in Dianthus caryophyllus is catalyzed by hydroxycinnamoyl/benzoyl-CoA:anthranilate N-hydroxycinnamoyl/ benzoyltransferase (HCBT), which couples hydroxycinnamoyl-CoAs and benzoyl-CoAs to anthranilate. We recently demonstrated the potential of using yeast (Saccharomyces cerevisiae) for the biological production of a few cinnamoyl anthranilates by heterologous co-expression of 4-coumaroyl:CoA ligase from Arabidopsis thaliana (4CL5) and HCBT. Here we report that, by exploiting the substrate flexibility of both 4CL5 and HCBT, we achieved rapid biosynthesis of more than 160 cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates in yeast upon feeding with both natural and non-natural cinnamates, dihydrocinnamates, benzoates, and anthranilates. Our results demonstrate the use of enzyme promiscuity in biological synthesis to achieve high chemical diversity within a defined class of molecules. This work also points to the potential for the combinatorial biosynthesis of diverse and valuable cinnamoylated, dihydrocinnamoylated, and benzoylated products by using the versatile biological enzyme 4CL5 along with characterized cinnamoyl- CoA- and benzoyl-CoA-utilizing transferases.},
doi = {10.1371/journal.pone.0138972},
journal = {PLoS ONE},
number = 10,
volume = 10,
place = {United States},
year = {Fri Oct 02 00:00:00 EDT 2015},
month = {Fri Oct 02 00:00:00 EDT 2015}
}
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Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1371/journal.pone.0138972
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Cited by: 13 works
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Figures / Tables:

Fig 1 Fig 1: Structure of cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates. (A) Cinnamoyl anthranilates. Tranilast: R1 = R2 = R3 = R6 = H, R4 = R5 = OMe. (B) Dihydrocinnamoyl anthranilates. DHavnD: R1 = R2 = R3 = R4 = R6 = H, R5 = OH. (C) Benzoyl anthranilates. Dianthramide Bmore » from D. caryophyllus: R1-6 = H.« less
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Dihydroavenanthramide D protects pancreatic β-cells from cytokine and streptozotocin toxicity
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Evaluation and optimization of antifibrotic activity of cinnamoyl anthranilates
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N-Benzoyl anthranilic acid derivatives as selective inhibitors of aldo–keto reductase AKR1C3
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journal, September 2013

Acyltransferases in plants: a good time to be BAHD
journal, June 2006

Balsacones D-I, dihydrocinnamoyl flavans from Populus balsamifera buds
journal, April 2014

Dianthramides A and B, two N-benzoylanthranilic acid derivatives from elicited tissues of Dianthus caryophyllus
journal, August 1984

NMR-Driven Discovery of Benzoylanthranilic Acid Inhibitors of Far Upstream Element Binding Protein Binding to the Human Oncogene c-myc Promoter
journal, September 2004

  • Huth, Jeffrey R.; Yu, Liping; Collins, Irene
  • Journal of Medicinal Chemistry, Vol. 47, Issue 20
  • DOI: 10.1021/jm0497803

Synthesis, Biological Evaluation, and Structure–Activity Relationships of 2-[2-(Benzoylamino)benzoylamino]benzoic Acid Analogues as Inhibitors of Adenovirus Replication
journal, March 2012

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  • DOI: 10.1021/jm201636v

Structure Optimization of 2-Benzamidobenzoic Acids as PqsD Inhibitors for Pseudomonas aeruginosa Infections and Elucidation of Binding Mode by SPR, STD NMR, and Molecular Docking
journal, July 2013

  • Weidel, Elisabeth; de Jong, Johannes C.; Brengel, Christian
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  • DOI: 10.1021/jm4006302

New Cytotoxic Cyclic Peptides and Dianthramide from Dianthus superbus
journal, September 2004

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  • Journal of Natural Products, Vol. 67, Issue 9
  • DOI: 10.1021/np040036v

Tranilast attenuates connective tissue growth factor-induced extracellular matrix accumulation in renal cells
journal, March 2006

The 4-coumarate:CoA ligase gene family in Arabidopsis thaliana comprises one rare, sinapate-activating and three commonly occurring isoenzymes
journal, February 2004

  • Hamberger, Björn; Hahlbrock, Klaus
  • Proceedings of the National Academy of Sciences, Vol. 101, Issue 7
  • DOI: 10.1073/pnas.0307307101

Avena sativa (Oat), A Potential Neutraceutical and Therapeutic Agent: An Overview
journal, January 2013

  • Singh, Rajinder; De, Subrata; Belkheir, Asma
  • Critical Reviews in Food Science and Nutrition, Vol. 53, Issue 2
  • DOI: 10.1080/10408398.2010.526725

FT011, a new anti-fibrotic drug, attenuates fibrosis and chronic heart failure in experimental diabetic cardiomyopathy
journal, May 2012

  • Zhang, Yuan; Edgley, Amanda J.; Cox, Alison J.
  • European Journal of Heart Failure, Vol. 14, Issue 5
  • DOI: 10.1093/eurjhf/hfs011

A Familiar Ring to It: Biosynthesis of Plant Benzoic Acids
journal, October 2014

Treatment of Cutaneous Sarcoidosis with Tranilast
journal, February 1995

FT23, an orally active antifibrotic compound, attenuates structural and functional abnormalities in an experimental model of diabetic cardiomyopathy
journal, July 2012

Potential health benefits of avenanthramides of oats
journal, December 2009

Manufacturing Molecules Through Metabolic Engineering
journal, December 2010

Metabolic Engineering of the Phenylpropanoid Pathway in Saccharomyces cerevisiae
journal, June 2005

4-Hydroxybenzoate-coenzyme A ligase from Rhodopseudomonas palustris: purification, gene sequence, and role in anaerobic degradation.
journal, February 1994

Production of hydroxycinnamoyl anthranilates from glucose in Escherichia coli
journal, January 2013

  • Eudes, Aymerick; Juminaga, Darmawi; Baidoo, Edward E. K.
  • Microbial Cell Factories, Vol. 12, Issue 1
  • DOI: 10.1186/1475-2859-12-62

A Target-Based High Throughput Screen Yields Trypanosoma brucei Hexokinase Small Molecule Inhibitors with Antiparasitic Activity
journal, April 2010

  • Sharlow, Elizabeth R.; Lyda, Todd A.; Dodson, Heidi C.
  • PLoS Neglected Tropical Diseases, Vol. 4, Issue 4
  • DOI: 10.1371/journal.pntd.0000659

A Purpose-Synthesised Anti-Fibrotic Agent Attenuates Experimental Kidney Diseases in the Rat
journal, October 2012

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  • Ang, Ee Lui; Sun, Huihua; Liu, Zihe
  • Drug Design, Development and Therapy
  • DOI: 10.2147/dddt.s63023
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