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Activation of Isoflavone Biosynthesis in Excised Cotyledons of Lupinus Seedlings by Jasmonoids and Excess Light Yasufumi Katagiri3, Yasuyuki Hashidokob*, Ragai K

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Activation of Isoflavone Biosynthesis in Excised Cotyledons of Lupinus Seedlings by Jasmonoids and Excess Light Yasufumi Katagiri3, Yasuyuki Hashidokob*, Ragai K Activation of Isoflavone Biosynthesis in Excised Cotyledons of Lupinus Seedlings by Jasmonoids and Excess Light Yasufumi Katagiri3, Yasuyuki Hashidokob*, Ragai K. Ibrahim0 and Satoshi Tahara3’b a CREST, Japan Science and Technology Corporation, Kawaguchi 332-0012, Japan b Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita-ku, Sapporo 060-8589, Japan. Fax: +81-11-706-4182. E-mail: [email protected] c Biology Department, Concordia University, Montreal, Quebec, Canada H3G 1M8 * Author for correspondence and reprint requests Z. Naturforsch. 56c, 1038-1046 (2001); received May 7/August 1, 2001 Isoflavone Accumulation, Jasmonoids, Lupinus spp. (Leguminosae) Exogenous jasmonic acid (JA) and methyl jasmonate (MJ) induced accumulation of isofla­ vone constituents in cotyledons prepared from imbibed seeds of white lupin (Lupinus albus L.). Exogenous 0.2 mM MJ enhanced the levels of 7-0-(6"-0-malonyl)glucosylgenistein and 7-O-glucosylgenistein in the cotyledons of etiolated seedlings that had been incubated in the dark for 48 h. Regarding isoflavone induced by excision and slicing in the cotyledons as background level, the effect of light was 2- to 3-fold higher than that of 0.2 mM MJ. Cotyle­ dons exposed to MJ along with a 24-h light period displayed a higher level of isoflavone accumulation than that of light alone. Total molar amounts of isoflavone accumulated in the cotyledons treated with MJ under continuous light were approximately the sum of those induced by MJ alone and light alone, respectively. The additive-like effect of MJ and light on isoflavone accumulation in lupin tissues suggested the presence of two different signaling systems independently responsible for those two stimuli. Excised cotyledons from etiolated yellow lupin (L. luteus L. cv. Topaz) seedlings also supported this hypothesis. The cotyledons could accumulate both an isoflavone and a flavone, and MJ selectively increased some of the isoflavone constituents, whereas light enhanced the levels of both. The selective accumulation mechanism of isoflavonoids in cotyledons, in which jasmonoids are involved, clearly differed from that activated by light. Introduction contrary, show a remarkably simple isoflavonoid Isoflavonoids (with a skeleton of 1,2-diphenyl- compositions, in which large amounts of 7-O-glu- propane, distinguished from other flavonoids hav­ cosylgenistein (2) and its 6"-0-malonyl derivatives ing a 1,3-diphenylpropane skeleton) are localized (1) are accumulated in green cotyledons (Katagiri in leguminous and some other plants. Lupins ( Lupi­ et al., 2000). We have recently found that seedlings nus : Leguminosae) produce prenylated isoflavones of yellow lupin contain substantial amounts of 8- (5, 6, 7 and so on, see Figs. 1 and 2) as defensive C-glucosylgenistein (3, an isoflavone) and 1-O-ß- (Harborne et al., 1976; Ingham et al., 1983) and (2-0-a-rhamnosyl)-glucosylapigenin (4, a flavone) other functional (Gagnon et al., 1995a) secondary in the green cotyledons (Zapesochnaya and La- metabolites. Both white (L. albus L.) and yellow (L. man, 1977; Franski et a l, 1999). luteus L.) lupins produce a prenylated isoflavone When white lupin is exposed to a biotic and/or an luteone (5) constitutively (Fukui etal., 1973) and in- abiotic stress, compound 5 and other antifungal ducibly (Ingham and Dewick, 1980; Shibuya et al., isoflavones are biosynthesized (Gagnon and 1992) as the most predominant antifungal com­ Ibrahim, 1997; Wojtaszek and Stobiecki, 1997) pounds. Healthy seedlings of white lupin, on the along with activation of phenylalanine ammonia-ly- ase (PAL) which is a key enzyme of flavonoid path­ way. It is also known that light irradiation increases flavonoid contents along with PAL activation Abbreviations: JA, jasmonic acid; MeCN, acetonitrile; MJ, methyl jasmonate; PAL, phenylalanine ammonia-ly- (Ward and Buzzel, 1983 and cited therein). This ase; SD, standard deviation. light-induced flavonoid accumulation is thought to 0939-5075/2001/1100-1038 $ 06.00 © 2001 Verlag der Zeitschrift für Naturforschung, Tübingen • www.znaturforsch.com • D Y. Katagiri et al. • Activation of Isoflavone Biosynthesis in Lupin Cotyledons 1039 Jasmonoids & Light — y C00H ^ 7 COOH CO-CoA OHSn h 2 CT' L-phenylal anine cinnamic acid cinnamoyl CoA 3 x Malonyl-CoA Pooled form HCV v 0 ' o o 7-0-ß-(6“-0-malonyl)glucosylgenistein (1) OH OH O 7-O-ß-glucosylgenistein (2) OH 2-hydroxygenistein (9) Fig. 1. Metabolic pathway of isoflavonoids in white and yellow lupin cotyledons. The flavonoids induced in cotyle­ dons of white and yellow lupins with MJ-treatment/light and other stresses, including excision, mechanical slicing, treatment with CuCl2 and fungal infection, are shown. These simple flavonone/isoflavones and their glucosides accumulated by MJ or light had no antifungal activity, but further stimulation with heavy metal and/or fungal infection led to conversion of the pooled isoflavones into major antifungal isoflavone (5) hydroxylated and preny­ lated at C-2' and C-6 positions, respectively. be involved in photoprotection systems of higher Materials and Methods plants. It has also been reported that jasmonic acid General (JA), an endogenous signal transducer, enhances the transcription level of PAL gene and induces fla­ A Waters HPLC system consisting of a 600E vonoids in some plants (Gundlach et al., 1992; G ra­ multisolvent delivery system, a 996 photodiode-ar- ham and Graham, 1996; Rakwal etal., 1996). ray detector, and a U6K injector were used for In order to know the phytochemical response of qualitative and quantitative analyses of the lupin lupin seedlings in association with signal transduc­ isoflavonoids. The plants were grown in growth tion, we investigated the effects of exogenous (±)- chambers, Biotron NC 220 (NK system, Osaka) jasmonic acid (JA) and methyl jasmonate (MJ) at 23 °C. and light radiation on isoflavonoid metabolism, particularly the quantitative responses. In this pa­ Chemicals per, we describe jasmonoid-mediated isoflavone Synthetic (±)-JA used in the preliminarily ex­ accumulation in excised lupin cotyledons which periments was donated from Dr. S. Tamogami and are epigeal and autotrophic, and discuss a signifi­ Prof. O. Kodama, Faculty of Agriculture, Ibaraki cance of the activation system in biosynthesis me­ University. MJ was purchased from Wako Pure diated by jasmonoids and light. Chemical Industries Co. These compounds were 1040 Y. Katagiri et al. ■ Activation of Isoflavone Biosynthesis in Lupin Cotyledons previously dissolved in acetone to be 200 m M , and nematica) followed by centrifugation at 3,000 x g the acetone solution was 1 x 103 times diluted with to give crude methanol extracts of lupin isoflavo- water. A chloroaniline Schiff base-type PAL inhib­ noids as the supernatant. Each extract portion itor, S-84702 was provided by Dr. T. Kato and Dr. (100 |il) was diluted with 4 ml of water to be K. Kamoshita, Sumitomo Chemical Industries Co. loaded on a Bond Elut C18 (reversed-phase silica Flavone (2-phenylchromone) used for an internal gel) cartridge column (Varian) previously washed standard in quantitative HPLC was from Tokyo with acetone, MeCN and subsequently with water. Chemical Industry Co. Ltd. As the standard solu­ The cartridge adsorbed the samples was first tion, 10 m M 2-phenylchromone in MeOH was used. washed with 5 ml of 5% MeCN-buffer (50 mM 8-C-Glucosylgenistein(3) and 7-0-/?-(2-0-a-rham- H3PO4-KOH, pH 3.0) and successively 5 ml of nosyl)-glucosylapigenin (4) from yellow lupin were water. Flavonoid constituents were then eluted identified by comparing the XH- and 13C-NMR from the cartridge with 3 ml of 86% MeCN-water. spectra with those reported previously (van Heer- The eluates were concentrated in vacuo up to dry­ den etal., 1980; Rao and Rao, 1982). Other isoflavo- ness, and the resulting residues were re-dissolved noids mentioned in the present paper were pre­ in 200 (il of 50% MeCN to give a sample solution viously isolated and identified in our laboratory for HPLC analyses. (Hashidoko et al., 1986; Tahara et al., 1984; 1989). Hydrolyses of isoflavone glycosides and cleanup Plant material To quantify malonylated glucosylisoflavone, Seeds of white lupin (L. albus L. cv. Kievskij 100 (il of a crude methanolic extract was dissolved Mutant) and yellow lupin (L. luteus L. cv. Topaz) in an excess volume of 0.4 m NH4OH and then were harvested at the experimental farm in Hok­ kept at 37 °C for 90 min. The resulting solution kaido University. When the cotyledons of the im­ was diluted and then subjected to the cleanup pro­ bibed seeds were used, they were prepared from cess described above. An estimated value of an soaking mature seeds in air-bubbled water at 37 °C isoflavone glucoside increasing after the mild alka­ for 6 hours. When the cotyledons from seedlings line hydrolysis was regarded those from the hy­ were used, the seedlings were grown as follows. drolysed malonylated derivative 1. For quantifica­ The mature seeds soaked in running tap water tion of total isoflavone in the cotyledons, only overnight were allowed to germinate in a bed of simple isoflavone aglycons obtained by complete clean and moistened vermiculite in growth cham­ acid hydrolysis were analyzed. Each extract por­ bers under 0- and 16-h photoperiods under condi­ tion was taken to a 10 ml capped glass tube, and tion at 10,000 lux at 23 °C. Cotyledons from the then removed the solvent in vacuo. The residues imbibed seeds or the seedlings grown for set re-dissolved in 200 |_d of EtOH were mixed with periods, were excised with a razor blade. To ex­ equal volume of 2 m aq. HC1, and then kept in clude the effect of light, the excision and following boiling water for 1 h (Markham, 1989). The hy­ treatments of the cotyledons were performed in a drolyzed mixture diluted with 4 ml of water was darkroom under intensive green light (from a Toki then charged on a conditioned Bond Elut C18 car­ green light bulb, 7 W).
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