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Characterization and Analysis of the Cotton Cyclopropane Fatty Acid Synthase Family and Their Contribution to Cyclopropane Fatty Acid Synthesis

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Characterization and Analysis of the Cotton Cyclopropane Fatty Acid Synthase Family and Their Contribution to Cyclopropane Fatty Acid Synthesis Yu et al. BMC Plant Biology 2011, 11:97 http://www.biomedcentral.com/1471-2229/11/97 RESEARCHARTICLE Open Access Characterization and analysis of the cotton cyclopropane fatty acid synthase family and their contribution to cyclopropane fatty acid synthesis Xiao-Hong Yu1, Richa Rawat1 and John Shanklin1,2* Abstract Background: Cyclopropane fatty acids (CPA) have been found in certain gymnosperms, Malvales, Litchi and other Sapindales. The presence of their unique strained ring structures confers physical and chemical properties characteristic of unsaturated fatty acids with the oxidative stability displayed by saturated fatty acids making them of considerable industrial interest. While cyclopropenoid fatty acids (CPE) are well-known inhibitors of fatty acid desaturation in animals, CPE can also inhibit the stearoyl-CoA desaturase and interfere with the maturation and reproduction of some insect species suggesting that in addition to their traditional role as storage lipids, CPE can contribute to the protection of plants from herbivory. Results: Three genes encoding cyclopropane synthase homologues GhCPS1, GhCPS2 and GhCPS3 were identified in cotton. Determination of gene transcript abundance revealed differences among the expression of GhCPS1, 2 and 3 showing high, intermediate and low levels, respectively, of transcripts in roots and stems; whereas GhCPS1 and 2 are both expressed at low levels in seeds. Analyses of fatty acid composition in different tissues indicate that the expression patterns of GhCPS1 and 2 correlate with cyclic fatty acid (CFA) distribution. Deletion of the N- terminal oxidase domain lowered GhCPS’s ability to produce cyclopropane fatty acid by approximately 70%. GhCPS1 and 2, but not 3 resulted in the production of cyclopropane fatty acids upon heterologous expression in yeast, tobacco BY2 cell and Arabidopsis seed. Conclusions: In cotton GhCPS1 and 2 gene expression correlates with the total CFA content in roots, stems and seeds. That GhCPS1 and 2 are expressed at a similar level in seed suggests both of them can be considered potential targets for gene silencing to reduce undesirable seed CPE accumulation. Because GhCPS1 is more active in yeast than the published Sterculia CPS and shows similar activity when expressed in model plant systems, it represents a strong candidate gene for CFA accumulation via heterologous expression in production plants. Background [8,9] and parasites [10]. There are two principle classes Fatty acids containing three-carbon carbocyclic rings, of bacterial cyclopropane synthases: the Escherichia coli especially cyclopropane fatty acids, occur infrequently in cyclopropane synthase (ECPS) type that uses unsatu- plants and their major plant producers include Malva- ratedphospholipidsassubstratesandMycobacterium ceae, Sterculiaceae, Bombaceae, Tilaceae, Gnetaceae and tuberculosis cyclopropane mycolic acid synthases Sapindaceae [1-4]. They can represent a significant com- (CMAs) that perform the introduction of cis-cyclopro- ponent of seed oils and accumulate to as much as 40% pane rings at proximal and distal positions of unsatu- in Litchi chinensis [1,5]. rated mycolic acids [11-14]. Despite their different Cyclopropane synthases (CPSs) catalyze the cyclopro- substrates the two classes of enzymes share up to 33% panation of unsaturated lipids in bacteria [6,7], plants sequence identity suggesting a common fold and reac- tion mechanism. Moreover, a shared reaction mechan- * Correspondence: [email protected] ism is suggested by the fact that both E. coli CPS and 1Department of Biochemistry and Cell Biology, Stony Brook University, NY, M. tuberculosis CMA active site residues are almost USA Full list of author information is available at the end of the article © 2011 Yu et al; licensee BioMed Central Ltd. This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Yu et al. BMC Plant Biology 2011, 11:97 Page 2 of 10 http://www.biomedcentral.com/1471-2229/11/97 completely conserved and harbor a bicarbonate ion in because the cyclopropene ring is highly strained and their active site [15,16]. readily opens in an exothermic reaction. This property Although CPA had been identified in a few plant makes CPE particularly suitable for the productions of seeds as early as 1960s [17], the key gene responsible for coatings and polymers. Sterculic acid (18-carbon cyclo- their biochemical synthesis was not identified for more propene) also has potential applications as a biocide in than three decades when Bao et al. [8] identified a fatty acid soap formulation (US2008/0155714A1). cyclopropane synthase from S. foetida.TheSfCPS is a In this study, we identify three CPS isoforms from microsomal-localized membrane enzyme, which cata- cotton and analyze their expression in different tissues lyzes the addition of a methylene group derived from S- to help define their physiological roles. We also present adenosyl-L-methionine across the double bond of oleic an analysis of the consequences of over-expressing cot- acid esterified to the sn-1 position of PC [9]. The S. foe- ton GhCPS1, 2 and 3 in yeast, tobacco suspension cells tida enzyme is the first plant CPS that has been charac- and Arabidopsis. terized, the other plant CPS has been reported to date is from Litchi sinensis (WO/2006087364). Methods E. coli CPS is thought to be involved in the long-term Plant growth conditions and transgenic analyses survival of non-growing cells and its expression can be Arabidopsis and camelina plants were grown in walk-in- associated with environmental stresses [6]. Plant CPEs growth chambers at 22°C for 16 h photoperiod, and cotton inhibit some insect stearoyl-CoA desaturases thereby plants were grown in the greenhouse at 28°C for 16 h interfering with their maturation and reproduction, sug- photoperiod. The full length cDNA corresponding to gesting that in addition to their role as storage lipids, GhCPS1[GenBank:574036.1],GhCPS2[GenBank:574037.1] CPE can also serve as protective agents. CPE are also and GhCPS3[GenBank:574038.1] genes were PCR ampli- strong inhibitors of a variety of fatty acid desaturases in fied using gene specific primers with restriction site- animals [18-21], and feeding animals with CPE -contain- encoding linkers and subsequently digested and cloned ing oilseeds, such as cotton seed meal, leads to accumu- into pYES2 (Invitrogen) via corresponding SacI and lation of hard fats and other physiological disorders EcoRI restriction sites. For Arabidopsis and camelina [20,22,23]. For the same reasons vegetable oils that con- transformation, the genes were cloned downstream of the tain CPE must be treated with high temperature hydro- phaseolin seed-specific promoter in binary vector pDsRed genation before human consumption. These treatments [25]. These binary vectors were introduced into Agrobac- add to processing costs and also result in the accumula- terium tumefaciens strain GV3101 by electroporation and tion of undesirable trans-fatty acids. Therefore, reducing were used to transform Arabidopsis via the floral dip the levels of CPE in cotton seed oil by gene-silencing or method [26], and camelina through vacuum infiltration other techniques could reduce processing costs and the [27]. Seeds of transformed plants were screened under associated production of undesirable trans fatty acids as fluorescence, emitted upon illumination with green light well as increasing the value of processed seed meal for from a X5 LED flashlight (Inova) in conjunction with a food consumption (US2010/0115669). 25A red camera filter [25]. For tobacco Bright Yellow 2 Cyclic fatty acids, especially CPA such as dihydroster- (BY2) transformation, GhCPS1 was cloned into pBI121 culic acid, are desirable for numerous industrial applica- using BamHI and SacI sites, and GhCPS2 and 3 were tions and therefore it would be useful to identify cloned into pBI121 using the XbaI and SacI restriction candidate enzymes for heterologous expression in pro- sites and transformed into BY2 cells. After 4-5 months duction plants with the goal of optimizing the accumu- kanamycin selection, stable transformed cell lines were lation of CPAs. CPAs have physical characteristics collected 7 days after subculture and analyzed for fatty somewhere in between saturated and mono unsaturated acid composition. The composition of pBI121-containing fatty acids. The strained bond angles of the carbocyclic negative control lines were compared with lines trans- ring are responsible for their unique chemistry and phy- formed with SfCPS in pBI121. sical properties. Hydrogenation results in ring opening Primers used in this study for: to produce methyl-branched fatty acids. These branched Yeast expression fatty acids have the low temperature properties of unsa- GCPS1-Y2F: ACCGGAGCTCAcca t g g a a g t g g c c turated fatty acids, but unlike unsaturated fatty acids, gtgatcg their esters are not susceptible to oxidation and are GCPS2-Y2F: ACCGGAGCTCAccatggaagtggc therefore ideally suited for use in lubricant formulations ggtgatcg [24] (WO 99/18217). Moreover, the methyl branched GCPS1+2-R: CCGGAATTC t c a a t c a t ccatgaa fatty acids are an alternative to isostearic acids that are ggaatatgc used as cosmetics. Oils with high levels of cyclopropene GCPS3-Y2F: ACCGGAGCTC AccATGGGTa t g a a a fatty acids self-polymerize at elevated temperatures atagcagtgataggaggag Yu et al. BMC Plant Biology 2011, 11:97 Page 3 of 10 http://www.biomedcentral.com/1471-2229/11/97 GCPS3-R: CCGGAATTC t t a a g a a g c t g a gggg RNA extraction, Reverse transcription and quantitative aagtcttt PCR analyses Arabidopsis transformation RNA from cotton leaf, flower, stem and seeds at differ- GCPS1-5’PacI: tcccTTAATTAA a t g g a a g t g g c c ent development stages were extracted according to Wu gtgatcg et al. [32] and RNA from cotton root was isolated using GCPS2-5’PacI: tcccTTAATTAAatggaagtggcg Qiagen’s plant Mini RNA kit. RNA quality and concen- gtgatcg tration were determined by gel electrophoresis and GCPS1+2-3’XmaI: tcccCCCGGGtcaatcatccat Nanodrop spectroscopy.
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