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The Synergistic Effect of Co-Treatment of Methyl Jasmonate

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The Synergistic Effect of Co-Treatment of Methyl Jasmonate International Journal of Molecular Sciences Article The Synergistic Effect of Co-Treatment of Methyl Jasmonate and Cyclodextrins on Pterocarpan Production in Sophora flavescens Cell Cultures 1,2, 1, 1 1 1 Soyoung Kim y, Yu Jeong Jeong y, Su Hyun Park , Sung-Chul Park , Saet Buyl Lee , Jiyoung Lee 1, Suk Weon Kim 1, Bo-Keun Ha 2, Hyun-Soon Kim 3, HyeRan Kim 3, Young Bae Ryu 4, Jae Cheol Jeong 1,* and Cha Young Kim 1,* 1 Biological Resource Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB), Jeongeup 56212, Korea; [email protected] (S.K.); [email protected] (Y.J.J.); [email protected] (S.H.P.); [email protected] (S.-C.P.); [email protected] (S.B.L.); [email protected] (J.L.); [email protected] (S.W.K.) 2 Department of Plant Biotechnology, College of Agriculture and Life Science, Chonnam National University, Gwangju 61186, Korea; [email protected] 3 Plant Systems Engineering Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB), Daejeon 34141, Korea; [email protected] (H.-S.K.); [email protected] (H.K.) 4 Functional Biomaterials Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB), Jeongeup 56212, Korea; [email protected] * Correspondence: [email protected] (J.C.J.); [email protected] (C.Y.K.); Tel.: +82-63-570-5001 (C.Y.K.); Fax: +82-63-570-5009 (C.Y.K.) These authors contributed equally to this work. y Received: 9 April 2020; Accepted: 29 May 2020; Published: 30 May 2020 Abstract: Pterocarpans are derivatives of isoflavonoids, found in many species of the family Fabaceae. Sophora flavescens Aiton is a promising traditional Asian medicinal plant. Plant cell suspension cultures represent an excellent source for the production of valuable secondary metabolites. Herein, we found that methyl jasmonate (MJ) elicited the activation of pterocarpan biosynthetic genes in cell suspension cultures of S. flavescens and enhanced the accumulation of pterocarpans, producing mainly trifolirhizin, trifolirhizin malonate, and maackiain. MJ application stimulated the expression of structural genes (PAL, C4H, 4CL, CHS, CHR, CHI, IFS, I3’H, and IFR) of the pterocarpan biosynthetic pathway. In addition, the co-treatment of MJ and methyl-β-cyclodextrin (MeβCD) as a solubilizer exhibited a synergistic effect on the activation of the pterocarpan biosynthetic genes. The maximum level of total pterocarpan production (37.2 mg/g dry weight (DW)) was obtained on day 17 after the application of 50 µM MJ on cells. We also found that the combined treatment of cells for seven days with MJ and MeβCD synergistically induced the pterocarpan production (trifolirhizin, trifolirhizin malonate, and maackiain) in the cells (58 mg/g DW) and culture medium (222.7 mg/L). Noteworthy, the co-treatment only stimulated the elevated extracellular production of maackiain in the culture medium, indicating its extracellular secretion; however, its glycosides (trifolirhizin and trifolirhizin malonate) were not detected in any significant amounts in the culture medium. This work provides new strategies for the pterocarpan production in plant cell suspension cultures, and shows MeβCD to be an effective solubilizer for the extracellular production of maackiain in the cell cultures of S. flavescens. Keywords: Sophora flavescens; cell cultures; pterocarpan; maackiain; trifolirhizin; elicitation Int. J. Mol. Sci. 2020, 21, 3944; doi:10.3390/ijms21113944 www.mdpi.com/journal/ijms Int. J. Mol. Sci. 2020, 21, 3944 2 of 14 Int. J. Mol. Sci. 2020, 21, x FOR PEER REVIEW 2 of 14 1. Introduction 1. Introduction Plants produce a wide variety of secondary metabolites that are economically important as pharmaceuticals,Plants produce agrochemicals, a wide variety bio-pesticides, of secondary flavors, metabolites fragrances, that colors,are economically and food additivesimportant [ 1as,2]. pharmaceuticals, agrochemicals, bio-pesticides, flavors, fragrances, colors, and food additives [1,2]. Sophora flavescens Aiton, the shrubby sophora, belongs to the family Fabaceae (Leguminosae) and is Sophora flavescens Aiton, the shrubby sophora, belongs to the family Fabaceae (Leguminosae) and is an important legume in Asia [3]. The root of S. flavescens, also known as Kosam in Korean (Kushen an important legume in Asia [3]. The root of S. flavescens, also known as Kosam in Korean (Kushen in Chinese), is commonly used as a traditional herbal medicine because of its various biological in Chinese), is commonly used as a traditional herbal medicine because of its various biological activities, including anti-cancer, anti-arrhythmic, anti-allergic, anti-inflammatory, and anti-asthmatic activities, including anti-cancer, anti-arrhythmic, anti-allergic, anti-inflammatory, and anti-asthmatic effects [3–6]. It has been officially listed in the Korean Pharmacopoeia and Chinese Pharmacopoeia. S. effects [3–6]. It has been officially listed in the Korean Pharmacopoeia and Chinese Pharmacopoeia. flavescens is known to produce a wide range of secondary metabolites, including flavonoids, alkaloids, S. flavescens is known to produce a wide range of secondary metabolites, including flavonoids, triterpenoids, and pterocarpans [3]. Among them, pterocarpans—including maackiain, trifolirhizin, alkaloids, triterpenoids, and pterocarpans [3]. Among them, pterocarpans—including maackiain, andtrifolirhizin, trifolirhizin and malonate—are trifolirhizin malonate—are isoflavonoids isofla foundvonoids in many found species in many of Fabaceae. species of TheyFabaceae. have They been reportedhave been to have reported various to have biological various activities, biological such activities, as anti-microbial, such as anti-microbial, anti-cancerous, anti-cancerous, anti-inflammatory, anti- andinflammatory, anti-malarial and activities anti-malarial [7,8]. Pterocarpansactivities [7,8]. comprise Pterocarpans the secondcomprise largest the second group largest of isoflavonoids group of afterisoflavonoids isoflavones. after They isoflavones. primarily They act asprimarily phytoalexins act as phytoalexins in leguminous in leguminous plants, and plants, also function and also as signalfunction molecules as signal in plant–microorganism molecules in plant–microorganism interactions [7,9 ].interactions Leguminous [7,9]. plants Leguminous are known plants to produce are pterocarpanknown to produce phytoalexins pterocarpan [10]. Pterocarpans phytoalexins of [10]. pisatin, Pterocarpans medicarpin, of pisatin, and maackiain medicarpin, are produced and maackiain in pea (Pisumare produced sativum), in peanut pea (Pisum (Arachis sativum hypogaea), peanut), and (ArachisSophora hypogaea japonica),, respectivelyand Sophora japonica [10–13]., respectively Pterocarpans [10– are formed13]. Pterocarpans at the last stages are formed of the flavonoidat the last biosyntheticstages of the pathwayflavonoid as biosynthetic a part of the pathway isoflavonoid as a part branch of the [7]. Isoflavonoidsisoflavonoid arebranch synthesized [7]. Isoflavo by anoids legume-specific are synthesized branch by of a thelegume general-specific phenylpropanoid branch of the pathway.general Thephenylpropanoid first product in pathway. the biosynthesis The first of product flavonoids in the and biosynthesis isoflavonoids of flavonoids is chalcone, and which isoflavonoids requires anis enzymaticchalcone, reactionwhich requires catalyzed an by enzymatic chalcone synthasereaction (CHS)catalyzed [14]. by Isoliquiritigenin chalcone synthase and liquiritigenin(CHS) [14]. areIsoliquiritigenin produced from and chalcones liquiritigenin by additional are produced legume-specific from chalcones enzymes, by additional chalcone reductaselegume-specific (CHR) andenzymes, chalcone chalcone isomerase reductase (CHI) (CHR) [15,16 ].and Isoflavonoid chalcone isomerase biosynthesis (CHI) is [15,16]. further Isoflavonoid catalyzed bybiosynthesis isoflavone synthaseis further (IFS) catalyzed to biosynthesize by isoflavone isoflavanone synthase (daidzein),(IFS) to biosynthesize which is then isoflavanone modified by(daidzein), methyltransferase which is (I4’OMT),then modified hydroxylase by (I3’H),methyltransferase reductase (IFR), (I4'OMT), glucosyltransferase hydroxylase (IF7GT), (I3'H), and malonyltransferasereductase (IFR), (IF7MaT)glucosyltransferase to form isoflavonoids (IF7GT), and (pterocarpans) malonyltransferase (Figure (IF7MaT)1)[ 17]. Theto form flavonoid isoflavonoids biosynthetic (pterocarpans) pathway has(Figure been elucidated,1) [17]. The andflavonoid many biosynthetic of the related pathwa genesy havehas been been elucidated, characterized and inmany other of speciesthe related [18]. Recently,genes have putative been genes characterized involved in in other the flavonoid species [18]. biosynthesis Recently, in putativeS. flavescens geneswere involved discovered in the by transcriptomeflavonoid biosynthesis (RNA-Seq) in analysis S. flavescens [5,19 were]. Lee discovered et al. [5] analyzed by transcript the contentsome (RNA-Seq) of phenolic analysis compounds [5,19]. inLee the et leaves, al. [5] stems,analyzed and the roots contents of S. of flavescens phenolic, and compounds have identified in the leaves, candidate stems, genes and involvedroots of S. in theflavescens biosynthesis, and ofhave phenolic identified acids candidate and flavonoids. genes involved They have in alsothe biosynthesis reported the of expression phenolic patternsacids and of theflavonoids. biosynthesis-related They have genesalso reported in different the organs expressi andon developmentalpatterns of the stages.biosynthesis-related genes in different organs
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