Plant unusual fatty acids: learning from the less common

Cahoon, Edgar B.; Li-Beisson, Yonghua

doi:10.1016/j.pbi.2020.03.007

Plant unusual fatty acids: learning from the less common

Journal Article · Wed Apr 15 00:00:00 EDT 2020 · Current Opinion in Plant Biology

DOI:https://doi.org/10.1016/j.pbi.2020.03.007· OSTI ID:1735713

Cahoon, Edgar B. ^[1]; Li-Beisson, Yonghua ^[2]

Univ. of Nebraska, Lincoln, NE (United States). Center for Plant Science Innovation and Department of Biochemistry; University of Nebraska-Lincoln
Aix-Marseille Univ., Marseille (France). CEA, CNRS, BIAM, Institut de Biosciences et Biotechnologies Aix-Marseille; Alternative Energies and Atomic Energy Commission (CEA), Cadarache (France)

The plant kingdom contains an abundance of structurally diverse fatty acids referred to as unusual fatty acids. Unusual fatty acids on plant surfaces can form polyesters that contribute to the function of cutin as a barrier for water loss and pathogen protection. Unusual fatty acids are also found as abundant components of seed oils of selected species and often confer desirable properties for industrial and nutritional applications. Here in this paper, we review recent findings on the biosynthesis and metabolism of unusual fatty acids in cutin and seed oils and use of this information for enzyme structure-function studies and seed oil metabolic engineering. We also highlight the recent discovery of unusual fatty acids that are formed from a previously undescribed variation of fatty acid elongation.

View Accepted Manuscript (DOE)

Research Organization:: Center for Advanced Bioenergy and Bioproducts Innovation (CABBI), Urbana, IL (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC), Biological and Environmental Research (BER)

Grant/Contract Number:: SC0018420

OSTI ID:: 1735713

Alternate ID(s):: OSTI ID: 1780286

Journal Information:: Current Opinion in Plant Biology, Journal Name: Current Opinion in Plant Biology Vol. 55; ISSN 1369-5266

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (44)

Plant sn -Glycerol-3-Phosphate Acyltransferases: Biocatalysts Involved in the Biosynthesis of Intracellular and Extracellular Lipids Jayawardhane, Kethmi N.; Singer, Stacy D.; Weselake, Randall J. Lipids, Vol. 53, Issue 5 https://doi.org/10.1002/lipd.12049	journal	May 2018
Betaine lipids Sato, Naoki The Botanical Magazine Tokyo, Vol. 105, Issue 1 https://doi.org/10.1007/BF02489414	journal	March 1992
Specialized lysophosphatidic acid acyltransferases contribute to unusual fatty acid accumulation in exotic Euphorbiaceae seed oils Shockey, Jay; Lager, Ida; Stymne, Sten Planta, Vol. 249, Issue 5 https://doi.org/10.1007/s00425-018-03086-y	journal	January 2019
How did nature engineer the highest surface lipid accumulation among plants? Exceptional expression of acyl-lipid-associated genes for the assembly of extracellular triacylglycerol by Bayberry (Myrica pensylvanica) fruits Simpson, Jeffrey P.; Thrower, Nicholas; Ohlrogge, John B. Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids, Vol. 1861, Issue 9 https://doi.org/10.1016/j.bbalip.2016.01.022	journal	September 2016
The biosynthesis of cutin and suberin as an alternative source of enzymes for the production of bio-based chemicals and materials Li, Yonghua; Beisson, Fred Biochimie, Vol. 91, Issue 6 https://doi.org/10.1016/j.biochi.2009.03.016	journal	June 2009
Nutritional enhancement in plants – green and greener Napier, Johnathan A.; Sayanova, Olga Current Opinion in Biotechnology, Vol. 61 https://doi.org/10.1016/j.copbio.2019.12.010	journal	February 2020
Solving the puzzles of cutin and suberin polymer biosynthesis Beisson, Fred; Li-Beisson, Yonghua; Pollard, Mike Current Opinion in Plant Biology, Vol. 15, Issue 3 https://doi.org/10.1016/j.pbi.2012.03.003	journal	June 2012
Understanding and manipulating plant lipid composition: Metabolic engineering leads the way Napier, Johnathan A.; Haslam, Richard P.; Beaudoin, Frederic Current Opinion in Plant Biology, Vol. 19 https://doi.org/10.1016/j.pbi.2014.04.001	journal	June 2014
What have we learnt from studying the evolution of the arbuscular mycorrhizal symbiosis? Vigneron, Nicolas; Radhakrishnan, Guru V.; Delaux, Pierre-Marc Current Opinion in Plant Biology, Vol. 44 https://doi.org/10.1016/j.pbi.2018.02.004	journal	August 2018
Review: Metabolic engineering of unusual lipids in the synthetic biology era Aznar-Moreno, Jose A.; Durrett, Timothy P. Plant Science, Vol. 263 https://doi.org/10.1016/j.plantsci.2017.07.007	journal	October 2017
Building lipid barriers: biosynthesis of cutin and suberin Pollard, Mike; Beisson, Fred; Li, Yonghua Trends in Plant Science, Vol. 13, Issue 5 https://doi.org/10.1016/j.tplants.2008.03.003	journal	May 2008
Cuphea wrightii thioesterases have unexpected broad specificities on saturated fatty acids Leonard, Jeffrey M.; Slabaugh, Mary B.; Knapp, Steven J. Plant Molecular Biology, Vol. 34, Issue 4, p. 669-679 https://doi.org/10.1023/A:1005846830784	journal	June 1997
Two distinct domains contribute to the substrate acyl chain length selectivity of plant acyl-ACP thioesterase Jing, Fuyuan; Zhao, Le; Yandeau-Nelson, Marna D. Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-03310-z	journal	February 2018
Discontinuous fatty acid elongation yields hydroxylated seed oil with improved function Li, Xiangjun; Teitgen, Alicen M.; Shirani, Asghar Nature Plants, Vol. 4, Issue 9 https://doi.org/10.1038/s41477-018-0225-7	journal	August 2018
Nature-Guided Synthesis of Advanced Bio-Lubricants Romsdahl, Trevor; Shirani, Asghar; Minto, Robert E. Scientific Reports, Vol. 9, Issue 1 https://doi.org/10.1038/s41598-019-48165-6	journal	August 2019
Identification of active site residues implies a two-step catalytic mechanism for acyl-ACP thioesterase Jing, Fuyuan; Yandeau-Nelson, Marna D.; Nikolau, Basil J. Biochemical Journal, Vol. 475, Issue 23 https://doi.org/10.1042/BCJ20180470	journal	December 2018
Production of high levels of 8:0 and 10:0 fatty acids in transgenic canola by overexpression of Ch FatB2, a thioesterase cDNA from Cuphea hookeriana Dehesh, Katayoon; Jones, Aubrey; Knutzon, Deborah S. The Plant Journal, Vol. 9, Issue 2, p. 167-172 https://doi.org/10.1046/j.1365-313X.1996.09020167.x	journal	February 1996
Identification of acyltransferases required for cutin biosynthesis and production of cutin with suberin-like monomers Li, Y.; Beisson, F.; Koo, A. J. K. Proceedings of the National Academy of Sciences, Vol. 104, Issue 46 https://doi.org/10.1073/pnas.0706984104	journal	November 2007
Nanoridges that characterize the surface morphology of flowers require the synthesis of cutin polyester Li-Beisson, Y.; Pollard, M.; Sauveplane, V. Proceedings of the National Academy of Sciences, Vol. 106, Issue 51 https://doi.org/10.1073/pnas.0909090106	journal	December 2009
A distinct type of glycerol-3-phosphate acyltransferase with sn-2 preference and phosphatase activity producing 2-monoacylglycerol Yang, W.; Pollard, M.; Li-Beisson, Y. Proceedings of the National Academy of Sciences, Vol. 107, Issue 26 https://doi.org/10.1073/pnas.0914149107	journal	June 2010
Fatty acid synthesis is inhibited by inefficient utilization of unusual fatty acids for glycerolipid assembly Bates, P. D.; Johnson, S. R.; Cao, X. Proceedings of the National Academy of Sciences, Vol. 111, Issue 3 https://doi.org/10.1073/pnas.1318511111	journal	January 2014
Redesign of soluble fatty acid desaturases from plants for altered substrate specificity and double bond position Cahoon, E. B.; Lindqvist, Y.; Schneider, G. Proceedings of the National Academy of Sciences, Vol. 94, Issue 10 https://doi.org/10.1073/pnas.94.10.4872	journal	May 1997
The Cytochrome P450 CYP86A22 Is a Fatty Acyl-CoA ω-Hydroxylase Essential for Estolide Synthesis in the Stigma of Petunia hybrida Han, Jixiang; Clement, Joel M.; Li, Jia Journal of Biological Chemistry, Vol. 285, Issue 6 https://doi.org/10.1074/jbc.M109.050765	journal	February 2010
Desaturases: Emerging Models for Understanding Functional Diversification of Diiron-containing Enzymes Shanklin, John; Guy, Jodie E.; Mishra, Girish Journal of Biological Chemistry, Vol. 284, Issue 28 https://doi.org/10.1074/jbc.R900009200	journal	April 2009
Cuphea : A new plant source of medium‐chain fatty acids Graham, Shirley A.; Knapp, Steven J. Critical Reviews in Food Science and Nutrition, Vol. 28, Issue 2 https://doi.org/10.1080/10408398909527495	journal	January 1989
A Land-Plant-Specific Glycerol-3-Phosphate Acyltransferase Family in Arabidopsis: Substrate Specificity, sn -2 Preference, and Evolution Yang, Weili; Simpson, Jeffrey P.; Li-Beisson, Yonghua Plant Physiology, Vol. 160, Issue 2 https://doi.org/10.1104/pp.112.201996	journal	August 2012
A Specialized Diacylglycerol Acyltransferase Contributes to the Extreme Medium-Chain Fatty Acid Content of Cuphea Seed Oil Iskandarov, Umidjon; Silva, Jillian E.; Kim, Hae Jin Plant Physiology, Vol. 174, Issue 1 https://doi.org/10.1104/pp.16.01894	journal	March 2017
Development Defects of Hydroxy-Fatty Acid-Accumulating Seeds Are Reduced by Castor Acyltransferases Lunn, Daniel; Smith, Gracen A.; Wallis, James G. Plant Physiology, Vol. 177, Issue 2 https://doi.org/10.1104/pp.17.01805	journal	April 2018
Identification of Genes Encoding Enzymes Catalyzing the Early Steps of Carrot Polyacetylene Biosynthesis Busta, Lucas; Yim, Won Cheol; LaBrant, Evan William Plant Physiology, Vol. 178, Issue 4 https://doi.org/10.1104/pp.18.01195	journal	October 2018
Tri-Hydroxy-Triacylglycerol Is Efficiently Produced by Position-Specific Castor Acyltransferases Lunn, Daniel; Wallis, James G.; Browse, John Plant Physiology, Vol. 179, Issue 3 https://doi.org/10.1104/pp.18.01409	journal	January 2019
Castor Stearoyl-ACP Desaturase Can Synthesize a Vicinal Diol by Dioxygenase Chemistry Whittle, Edward J.; Cai, Yuanheng; Keereetaweep, Jantana Plant Physiology, Vol. 182, Issue 2 https://doi.org/10.1104/pp.19.01111	journal	December 2019
A Novel Pathway for Triacylglycerol Biosynthesis Is Responsible for the Accumulation of Massive Quantities of Glycerolipids in the Surface Wax of Bayberry ( Myrica pensylvanica ) Fruit Simpson, Jeffrey P.; Ohlrogge, John B. The Plant Cell, Vol. 28, Issue 1 https://doi.org/10.1105/tpc.15.00900	journal	January 2016
Analysis of the aliphatic monomer composition of polyesters associated with Arabidopsis epidermis: occurrence of octadeca-cis-6, cis-9-diene-1,18-dioate as the major component: Polyester composition of Arabidopsis epidermis Bonaventure, Gustavo; Beisson, Frédéric; Ohlrogge, John The Plant Journal, Vol. 40, Issue 6 https://doi.org/10.1111/j.1365-313X.2004.02258.x	journal	October 2004
The pathway of triacylglycerol synthesis through phosphatidylcholine in Arabidopsis produces a bottleneck for the accumulation of unusual fatty acids in transgenic seeds: PC is a bottleneck in HFA-TAG synthesis Bates, Philip D.; Browse, John The Plant Journal, Vol. 68, Issue 3 https://doi.org/10.1111/j.1365-313X.2011.04693.x	journal	August 2011
Arabidopsis thaliana EPOXIDE HYDROLASE1 (AtEH1) is a cytosolic epoxide hydrolase involved in the synthesis of poly-hydroxylated cutin monomers Pineau, Emmanuelle; Xu, Lin; Renault, Hugues New Phytologist, Vol. 215, Issue 1 https://doi.org/10.1111/nph.14590	journal	May 2017
Redirection of metabolic flux for high levels of omega-7 monounsaturated fatty acid accumulation in camelina seeds Nguyen, Huu Tam; Park, Hyunwoo; Koster, Karen L. Plant Biotechnology Journal, Vol. 13, Issue 1 https://doi.org/10.1111/pbi.12233	journal	July 2014
PlantFAdb: a resource for exploring hundreds of plant fatty acid structures synthesized by thousands of plants and their phylogenetic relationships Ohlrogge, John; Thrower, Nick; Mhaske, Vandana The Plant Journal, Vol. 96, Issue 6 https://doi.org/10.1111/tpj.14102	journal	November 2018
Catalytic Plasticity of Fatty Acid Modification Enzymes Underlying Chemical Diversity of Plant Lipids Broun, Pierre; Shanklin, John; Whittle, Ed Science, Vol. 282, Issue 5392, p. 1315-1317 https://doi.org/10.1126/science.282.5392.1315	journal	November 1998
The plant lipidome in human and environmental health Horn, P. J.; Benning, C. Science, Vol. 353, Issue 6305 https://doi.org/10.1126/science.aaf6206	journal	September 2016
Plants transfer lipids to sustain colonization by mutualistic mycorrhizal and parasitic fungi Jiang, Yina; Wang, Wanxiao; Xie, Qiujin Science, Vol. 356, Issue 6343 https://doi.org/10.1126/science.aam9970	journal	June 2017
Fatty acids in arbuscular mycorrhizal fungi are synthesized by the host plant Luginbuehl, Leonie H.; Menard, Guillaume N.; Kurup, Smita Science, Vol. 356, Issue 6343 https://doi.org/10.1126/science.aan0081	journal	June 2017
Chimeric Fatty Acyl-Acyl Carrier Protein Thioesterases Provide Mechanistic Insight into Enzyme Specificity and Expression Ziesack, Marika; Rollins, Nathan; Shah, Aashna Applied and Environmental Microbiology, Vol. 84, Issue 10 https://doi.org/10.1128/AEM.02868-17	journal	March 2018
The Production of Unusual Fatty Acids in Transgenic Plants Napier, Johnathan A. Annual Review of Plant Biology, Vol. 58, Issue 1 https://doi.org/10.1146/annurev.arplant.58.032806.103811	journal	June 2007
Acyl-Lipid Metabolism Li-Beisson, Yonghua; Shorrosh, Basil; Beisson, Fred The Arabidopsis Book, Vol. 11 https://doi.org/10.1199/tab.0161	journal	January 2013

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Plant unusual fatty acids: learning from the less common

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