Identification of bottlenecks in the accumulation of cyclic fatty acids in camelina seed oil

Yu, Xiao-Hong; Cahoon, Rebecca E.; Horn, Patrick J.; Shi, Hai; Prakash, Richa Rawat; Cai, Yuanheng; Hearney, Maegan; Chapman, Kent D.; Cahoon, Edgar B.; Schwender, Jorg; Shanklin, John

doi:10.1111/pbi.12839

Title: Identification of bottlenecks in the accumulation of cyclic fatty acids in camelina seed oil

Journal Article · 20 September 2017 · Plant Biotechnology Journal

DOI: https://doi.org/10.1111/pbi.12839 · OSTI ID:1412647

Yu, Xiao-Hong ^[1]; Cahoon, Rebecca E. ^[2]; Horn, Patrick J. ^[3]; Shi, Hai ^[4]; Prakash, Richa Rawat ^[1]; Cai, Yuanheng ^[5]; Hearney, Maegan ^[4]; Chapman, Kent D. ^[3]; Cahoon, Edgar B. ^[2]; Schwender, Jorg ^[6]; Shanklin, John ^[6]

Stony Brook Univ., NY (United States). Dept. of Chemistry. Biochemistry and Cell Biology Dept.
Univ. of Nebrask. Center for Plant Science Innovation and Dept. of Biochemistry
Univ. of North Texas, Denton, TX (United States). Center for Advanced Scientific Computing and Modeling (CASCaM). Dept. of Biological Sciences
Brookhaven National Lab. (BNL), Upton, NY (United States). Biology Dept.
Stony Brook Univ., NY (United States). Biochemistry and Cell Biology Dept.
Stony Brook Univ., NY (United States). Dept. of Chemistry. Biochemistry and Cell Biology Dept.; Brookhaven National Lab. (BNL), Upton, NY (United States). Biology Dept.

Modified fatty acids (mFA) have diverse uses, e.g., cyclopropane fatty acids (CPA) are feedstocks for producing coatings, lubricants, plastics, and cosmetics. The expression of mFA-producing enzymes in crop and model plants generally results in lower levels of mFA accumulation than in their natural-occurring source plants. In order to further our understanding of metabolic bottlenecks that limit mFA accumulation, we generated transgenic Camelina sativa lines co-expressing Escherichia coli cyclopropane synthase (EcCPS) and Sterculia foetida lysophosphatidic acid acyltransferase (SfLPAT). In contrast to transgenic CPA-accumulating Arabidopsis, CPA accumulation in camelina caused only minor changes in seed weight, germination rate, oil accumulation, and seedling development. CPA accumulated to much higher levels in membrane than storage lipids, comprising more than 60% of total fatty acid in both phosphatidylcholine (PC) and phosphatidylethanolamine (PE) versus 26% in diacylglycerol (DAG) and 12% in triacylglycerol (TAG) indicating bottlenecks in the transfer of CPA from PC to DAG and from DAG to TAG. Upon coexpression of SfLPAT with EcCPS, di-CPA-PC increased by ~50% relative to lines expressing EcCPS alone with the di-CPA-PC primarily observed in the embryonic axis and mono-CPA-PC primarily in cotyledon tissue. EcCPS-SfLPAT lines revealed a redistribution of CPA from the sn-1 to sn-2 positions within PC and PE that was associated with a doubling of CPA accumulation in both DAG and TAG. Finally, the identification of metabolic bottlenecks in acyl transfer between site of synthesis (phospholipids) and deposition in storage oils (TAGs) lays the foundation for the optimizing CPA accumulation through directed engineering of oil synthesis in target crops.

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Research Organization:: Brookhaven National Laboratory (BNL), Upton, NY (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Biological and Environmental Research (BER); National Science Foundation (NSF)

Grant/Contract Number:: SC0012704; FG02-09ER64812; KC0304000; DBI 1117680

OSTI ID:: 1412647

Report Number(s):: BNL-114333-2017-JA

Journal Information:: Plant Biotechnology Journal, Vol. 16, Issue 4; ISSN 1467-7644

Publisher:: Society for Experimental Biology; Association of Applied BiologyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 27 works

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Fatty Acid Distribution in Bacterial Phospholipids. The Specificity of the Cyclopropane Synthetase Reaction ^* Hildebrand, John G.; Law, John H. Biochemistry, Vol. 3, Issue 9 https://doi.org/10.1021/bi00897a020	journal	September 1964
The emerging biofuel crop Camelina sativa retains a highly undifferentiated hexaploid genome structure Kagale, Sateesh; Koh, Chushin; Nixon, John Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms4706	journal	April 2014
Evidence for the reversibility of the acyl-CoA:lysophosphatidylcholine acyltransferase in microsomal preparations from developing safflower (Carthamus tinctorius L.) cotyledons and rat liver Stymne, S.; Stobart, A. K. Biochemical Journal, Vol. 223, Issue 2 https://doi.org/10.1042/bj2230305	journal	October 1984
Modulating seed β-ketoacyl-acyl carrier protein synthase II level converts the composition of a temperate seed oil to that of a palm-like tropical oil Pidkowich, M. S.; Nguyen, H. T.; Heilmann, I. Proceedings of the National Academy of Sciences, Vol. 104, Issue 11, p. 4742-4747 https://doi.org/10.1073/pnas.0611141104	journal	March 2007
An enzyme regulating triacylglycerol composition is encoded by the ROD1 gene of Arabidopsis Lu, C.; Xin, Z.; Ren, Z. Proceedings of the National Academy of Sciences, Vol. 106, Issue 44 https://doi.org/10.1073/pnas.0908848106	journal	October 2009
Carbocyclic fatty acids in plants: Biochemical and molecular genetic characterization of cyclopropane fatty acid synthesis of Sterculia foetida Bao, X.; Katz, S.; Pollard, M. Proceedings of the National Academy of Sciences, Vol. 99, Issue 10 https://doi.org/10.1073/pnas.092152999	journal	May 2002
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
Endoplasmic Reticulum-Located PDAT1-2 from Castor Bean Enhances Hydroxy Fatty Acid Accumulation in Transgenic Plants Kim, Hyun Uk; Lee, Kyeong-Ryeol; Go, Young Sam Plant and Cell Physiology, Vol. 52, Issue 6 https://doi.org/10.1093/pcp/pcr051	journal	June 2011
The Phosphatidylcholine Diacylglycerol Cholinephosphotransferase Is Required for Efficient Hydroxy Fatty Acid Accumulation in Transgenic Arabidopsis Hu, Zhaohui; Ren, Zhonghai; Lu, Chaofu Plant Physiology, Vol. 158, Issue 4 https://doi.org/10.1104/pp.111.192153	journal	February 2012
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Two Acyltransferases Contribute Differently to Linolenic Acid Levels in Seed Oil Marmon, Sofia; Sturtevant, Drew; Herrfurth, Cornelia Plant Physiology, Vol. 173, Issue 4 https://doi.org/10.1104/pp.16.01865	journal	February 2017
Phospholipase Dζ Enhances Diacylglycerol Flux into Triacylglycerol Yang, Wenyu; Wang, Geliang; Li, Jia Plant Physiology, Vol. 174, Issue 1 https://doi.org/10.1104/pp.17.00026	journal	March 2017
Metabolic Interactions between the Lands Cycle and the Kennedy Pathway of Glycerolipid Synthesis in Arabidopsis Developing Seeds Wang, Liping; Shen, Wenyun; Kazachkov, Michael The Plant Cell, Vol. 24, Issue 11 https://doi.org/10.1105/tpc.112.104604	journal	November 2012
Metabolic engineering of hydroxy fatty acid production in plants: RcDGAT2 drives dramatic increases in ricinoleate levels in seed oil Burgal, Julie; Shockey, Jay; Lu, Chaofu Plant Biotechnology Journal, Vol. 6, Issue 8 https://doi.org/10.1111/j.1467-7652.2008.00361.x	journal	October 2008
Camelina seed transcriptome: a tool for meal and oil improvement and translational research Nguyen, Huu T.; Silva, Jillian E.; Podicheti, Ram Plant Biotechnology Journal, Vol. 11, Issue 6 https://doi.org/10.1111/pbi.12068	journal	April 2013
Identification of multiple lipid genes with modifications in expression and sequence associated with the evolution of hydroxy fatty acid accumulation in Physaria fendleri Horn, Patrick J.; Liu, Jinjie; Cocuron, Jean-Christophe The Plant Journal, Vol. 86, Issue 4 https://doi.org/10.1111/tpj.13163	journal	May 2016
Synthetic redesign of plant lipid metabolism Haslam, Richard P.; Sayanova, Olga; Kim, Hae Jin The Plant Journal, Vol. 87, Issue 1 https://doi.org/10.1111/tpj.13172	journal	June 2016
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
Cyclopropane ring formation in membrane lipids of bacteria Grogan, D. W.; Cronan, J. E. Microbiology and Molecular Biology Reviews, Vol. 61, Issue 4 https://doi.org/10.1128/mmbr.61.4.429-441.1997	journal	December 1997
Characterization and analysis of the cotton cyclopropane fatty acid synthase family and their contribution to cyclopropane fatty acid synthesis Yu, Xiao-Hong; Rawat, Richa; Shanklin, John BMC Plant Biology, Vol. 11, Issue 1 https://doi.org/10.1186/1471-2229-11-97	journal	January 2011
Expression of Castor LPAT2 Enhances Ricinoleic Acid Content at the sn-2 Position of Triacylglycerols in Lesquerella Seed Chen, Grace; van Erp, Harrie; Martin-Moreno, Jose International Journal of Molecular Sciences, Vol. 17, Issue 4 https://doi.org/10.3390/ijms17040507	journal	April 2016
Characterization of Oilseed Lipids from “DHA-Producing Camelina sativa”: A New Transformed Land Plant Containing Long-Chain Omega-3 Oils Mansour, Maged; Shrestha, Pushkar; Belide, Srinivas Nutrients, Vol. 6, Issue 2 https://doi.org/10.3390/nu6020776	journal	February 2014

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Tissue-specific differences in metabolites and transcripts contribute to the heterogeneity of ricinoleic acid accumulation in Ricinus communis L. (castor) seeds Sturtevant, Drew; Romsdahl, Trevor B.; Yu, Xiao-Hong Metabolomics, Vol. 15, Issue 1 https://doi.org/10.1007/s11306-018-1464-3	journal	January 2019
Cyclopropane fatty acid biosynthesis in plants: phylogenetic and biochemical analysis of Litchi Kennedy pathway and acyl editing cycle genes Shockey, Jay; Kuhn, David; Chen, Tao Plant Cell Reports, Vol. 37, Issue 11 https://doi.org/10.1007/s00299-018-2329-y	journal	August 2018
Enhanced Production of High‐Value Cyclopropane Fatty Acid in Yeast Engineered for Increased Lipid Synthesis and Accumulation Peng, Huadong; He, Lizhong; Haritos, Victoria S. Biotechnology Journal, Vol. 14, Issue 4 https://doi.org/10.1002/biot.201800487	journal	October 2018
Producing Cyclopropane Fatty Acid in Plant Leafy Biomass via Expression of Bacterial and Plant Cyclopropane Fatty Acid Synthases Okada, Shoko; Taylor, Matthew; Zhou, Xue-Rong Frontiers in Plant Science, Vol. 11 https://doi.org/10.3389/fpls.2020.00030	journal	February 2020

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59 BASIC BIOLOGICAL SCIENCES
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cyclopropane fatty acid
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unusual fatty acid
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triacylglycerol
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Title: Identification of bottlenecks in the accumulation of cyclic fatty acids in camelina seed oil

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