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2013 | 35 | 07 |
Tytuł artykułu

Identification of dehydrocostus lactone and 4-hydroxy-b-thujone as auxin polar transport inhibitors

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The survey of naturally occurring of auxin polar transport regulators in Asteraceae was investigated using the radish (Raphanus sativus L.) hypocotyl bioassay established in this study. Significant auxin polar transport was observed when radiolabeled indole-3-acetic acid (IAA) was applied at the apical side of radish hypocotyl segments, but not when it was applied at the basal side of the segments. Almost no auxin polar transport was observed in radish hypocotyl segments treated with synthetic auxin polar transport inhibitors of N-(1- naphthyl)phthalamic acid (NPA) and 9-hydroxyfluorene-9- carboxylic acid (HFCA) at 0.5 lg/plant. 2,3,5-Triiodobenzoic acid (TIBA) at 0.5 μg/plant was less effective than NPA and HFCA, and p-chlorophenoxyisobutyric acid (PCIB) at 0.5 μg/ plant had almost no effect on auxin polar transport in the radish hypocotyl bioassay. These results strongly suggest that the radish hypocotyl bioassay is suitable for the detection of bioassay-derived auxin polar transport regulators. Using the radish hypocotyl bioassay and physicochemical analyses, dehydrocostus lactone (decahydro-3,6,9-tris-methylene-azulenol (4,5-b)furan-2(3H)-one) and 4-hydroxy-β-thujone (4-hydroxy- 4-methyl-1-(1-methylethyl)-bicyclo[3.1.0]hexan-3-one) were successfully identified as auxin polar transport inhibitors from Saussurea costus and Arctium lappa, and Artemisia absinthium, respectively. About 50 and 40 % inhibitions of auxin polar transport in radish hypocotyl segments were observed at 2.5 μg/plant pre-treatment (see ‘‘Materials and methods’’) of dehydrocostus lactone and 4-hydroxy-β-thujone, respectively. Although the mode of action of these compounds in inhibiting auxin polar transport has not been clear yet, their possible mechanisms are discussed.
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  • Graduate School of Science, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
  • Graduate School of Science, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
  • Graduate School of Science, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
  • Graduate School of Science, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
  • Graduate School of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan
  • Graduate School of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan
  • Graduate School of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan
  • Graduate School of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan
  • Koshiro Co. Ltd., 57 Wakamiya-suji, Namikawa, Oui-cho, Kameoka, Kyoto 621-0013, Japan
  • Faculty of Liberal Arts and Sciences, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
  • Graduate School of Science, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
  • Bernasconi P, Patel BC, Reagan JD, Subramanian MV (1996) The N-1-naphthylphthalamic acid-binding protein is an integral membrane protein. Plant Physiol 111:427–432
  • Brown DE, Rashotte AM, Murphy AS, Normanly J, Tague BW, Peer WA, Taiz L, Muday GK (2001) Flavonoids act as negative regulators of auxin transport in vivo in Arabidopsis. Plant Physiol 126:524–535
  • Burton JD, Pedersen MK, Coble HD (2008) Effect of cyclanilide on auxin activity. J Plant Growth Regul 27:342–352
  • Butturini E, Cavalieri E, Carcereri de Prati A, Darra E, Rigo A, Shoji K, Murayama N, Yamazaki H, Watanabe Y, Suzuki H, Mariotto S (2011) Two naturally occurring terpenes, dehydrocostuslactone and costunolide, decrease intracellular GSH content and inhibit STAT3 activation. PLoS ONE 6:e20174. doi:10.1371/journal.pone.0020174
  • Chen R, Masson PH (2005) Auxin transport and recycling of PIN proteins in plants. In: Šamaja J, Balška F, Menzel D (eds) Plant endocytosis. Springer, Berlin, pp 139–157
  • Gälweiler L, Guan C, Müller A, Wisman E, Mendgen K, Yephremov A, Palme K (1998) Regulation of polar auxin transport by AtPIN1 in Arabidopsis vascular tissue. Science 282:2226–2230
  • Geldner N, Friml J, Stierhof Y-D, Jürgens G, Palme K (2001) Auxin transport inhibitors block PIN1 cycling and vesicle trafficking. Nature 413:425–428
  • He X, Ortiz de Montellano PR (2004) Radical rebound mechanism in cytochrome P-450-catalyzed hydroxylation of the multifaceted radical clocks a- and b-thujone. J Biol Chem 279:39479–39484
  • Höld KM, Sirisoma NS, Ikeda T, Narahashi T, Casida JE (2000) a-Thujone (the active component of absinthe): c-aminobutyric acid type A receptor modulation and metabolic detoxification. PNAS 97:3826–3831
  • Höld KM, Sirisoma NS, Casida JE (2001) Detoxification of a- and β-thujones (the active ingredients of absinthe): site specificity and species differences in cytochrome P450 oxidation in vitro and in vivo. Chem Res Toxicol 14:589–595
  • Hoshino T, Miyamoto K, Ueda J (2006) Requirement of the gravitycontrolled transport of auxin for a negative gravitropic response in early growth stage of etiolated pea epicotyls. Plant Cell Physiol 47:1496–1508
  • Hoshino T, Miyamoto K, Ueda J (2007) Gravity-controlled asymmetrical transport of auxin regulates a gravitropic response in the early growth stage of etiolated pea (Pisum sativum) epicotyls: studies using simulated microgravity conditions on a threedimensional clinostat and using an agravitropic mutant, ageotropum. J Plant Res 120:619–628
  • Hussain S, Tripathi D, Sharma M (2011) Synthesis and biological study of some new derivatives of sesquiterpene lactones isolated from medicinal plants. J Phys Sci 22:57–75
  • Joel DM, Chaudhuri SK, Plakhine D, Ziadna H, Steffens JC (2011) Dehydrocostus lactone is exuded from sunflower roots and stimulates germination of the root parasite Orobanche cumana. Phytochemistry 72:624–634
  • Judþentienë A, Mockutë D (2004) Chemical composition of essential oils of Artemisia absinthium L. (wormwood) growing wild in Vilnius. Chemija 15:64–68
  • Kim J-Y, Henrichs S, Bailly A, Vincenzetti V, Sovero V, Mancuso S, Pollmann S, Kim D, Geisler M, Nam H-G (2010) Identification of an ABCB/P-glycoprotein-specific inhibitor of auxin transport by chemical genomics. J Biol Chem 285:23309–23317
  • Konaklieva MI, Plotkin BJ (2005) Lactones: generic inhibitors of enzymes? Mini Rev Med Chem 5:73–95
  • Krecek P, Skupa P, Libus J, Naramoto S, Tejos R, Friml J, Zazımalová E (2009) The PIN-FORMED (PIN) protein family of auxin transporters. Genome Biol 10:249. doi:10.1186/gb-2009-10-12-249
  • Lomax TL, Muday GK, Rubery H (1995) Auxin transport. In: Davis PJ (ed) Plant hormones. Kluwer Academic Publishers, Dordrecht, pp 509–530
  • Marchant A, Kargul J, May ST, Muller P, Delbarre A, Perrot-Rechenmann C, Bennett MJ (1999) AUX1 regulates root gravitropism in Arabidopsis by facilitating auxin uptake within root apical tissues. EMBO J 18:2066–2073
  • Matsuda H, Kagerura T, Toguchida I, Ueda H, Morikawa T, Yoshikawa M (2000) Inhibitory effects of sesquiterpenes from bay leaf on nitric oxide production in lipopolysaccharideactivated macrophages: structure requirement and role of heat shock protein induction. Life Sci 66:2151–2157
  • Maya DJ, Cassels BK, Iturriaga-Vásquez P, Ferreira J, Faúndez M, Galanti N, Ferreira A, Morello A (2007) Mode of action of natural and synthetic drugs against Trypanosoma cruzi and their interaction with the mammalian host. Comp Biochem Physiol Part A 146:601–620
  • Michalke W, Katekar GF, Geissler AE (1992) Phytotropin-binding sites and auxin transport in Cucurbita pepo: evidence for two recognition sites. Planta 181:254–260
  • Muday GK, Brunn SA, Haworth P, Subramanian M (1993) Evidence for a single naphthylphthalamic acid binding site on the zucchini plasma membrane. Plant Physiol 103:449–456
  • Nishimura T, Matano N, Morishima T, Kakinuma C, Hayashi K, Komano T, Kubo M, Hasebe M, Kasahara H, Kamiya Y, Koshiba T (2012) Identification of IAA transport inhibitors including compounds affecting cellular PIN trafficking by two chemical screening approaches using maize coleoptile systems. Plant Cell Physiol 53:1671–1682
  • Noh B, Murphy AS, Spalding EP (2001) Multidrugresistance-like genes of Arabidopsis required for auxin transport and auxinmediated development. Plant Cell 13:2441–2454
  • Noh B, Bandyopadhyay A, Peer WA, Spalding EP, Murphy AS (2003) Enhanced gravi- and phototropism in plant mdr mutants mislocalizing the auxin efflux protein PIN1. Nature 423: 999–1002
  • Oka M, Ueda J, Miyamoto K, Yamamoto R, Hoson T, Kamisaka S (1995) Effect of simulated microgravity on auxin polar transport in inflorescence axis of Arabidopsis thaliana. Biol Sci Space 9:331–336
  • Oka M, Miyamoto K, Okada K, Ueda J (1999) Auxin polar transport and flower formation in Arabidopsis thaliana transformed with indoleacetamide hydrolase (iaaH) gene. Plant Cell Physiol 40:231–237
  • Okada K, Ueda J, Komaki MK, Bell CJ, Shimura Y (1991) Requirement of auxin polar transport system in early stage of Arabidopsis floral bud formation. Plant Cell 3:677–684
  • Ruegger M, Dewey E, Hobbie L, Brown D, Bernasconi P, Turner J, Muday G, Estelle M (1997) Reduced naphthylphthalamic acid binding in the tir3 mutant of Arabidopsis is associated with a reduction in polar transport and diverse morphological defects. Plant Cell 9:745–757
  • Santelia D, Vincenzetti V, Azzarello E, Bovet L, Fukao Y, Duchtig P, Mancuso S, Martinoia E, Geisler M (2005) MDR-like ABC transporter AtPGP4 is involved in auxin-mediated lateral root and root hair development. FEBS Lett 579:5399–5406
  • Santelia D, Henrichs S, Vincenzetti V, Sauer M, Bigler L, Klein M, Bailly A, Lee Y, Friml J, Geisler M, Martinoia E (2008)
  • Flavonoids redirect PIN-mediated polar auxin fluxes during root gravitropic responses. J Biol Chem 283:31218–31226
  • Singh IP, Talwar KK, Arora JK, Chhabra BR, Kalsi PS (1992) A biologically active guaianolide from Saussurea lappa. Phytochemistry 31:2529–2531
  • Sun CM, Syu W Jr, Don MJ, Lu JJ, Lee GH (2003) Cytotoxic sesquiterpene lactones from the root of Saussurea lappa. J Nat Prod 66:1175–1180
  • Sussman MR, Goldsmith MHM (1981) The action of specific inhibitors of auxin transport on uptake of auxin and binding of N-naphthylphthalamic acid to a membrane site in maize coleoptiles. Planta 152:13–18
  • Swarup R, Friml J, Marchant A, Ljung K, Sandberg G, Palme K, Bennett M (2001) Localization of the auxin permease AUX1 suggests two functionally distinct hormone transport pathways operate in the Arabidopsis root apex. Genes Dev 15:2648–2653
  • Tetley RM, Thimann KV (1975) The metabolism of oat leaves during senescence. IV. The effects of a,a0-dipyridyl and other metal chelators on senescence. Plant Physiol 56:140–142
  • Thimann KV (1977) Polarity and the transport of auxin. In: Hormon action in the whole life of plants. The University of Massachusetts Press, Amherst, pp 71–92
  • Thomson KS, Leopold AC (1974) In vitro binding of morphactins and 1-N-naphthylphthalamic acid in corn coleoptiles and their effect on auxin transport. Planta 115:259–270
  • Thomson KS, Hertel R, Muller S, Tavares JE (1973) 1-N-Naphthylphthalamic acid and 2,3,5-triiodobenzoic acid. In-vitro binding to particulate cell fractions and action on auxin transport in corn coleoptiles. Planta 109:337–352
  • Ueda J, Miyamoto K, Uheda E, Oka M (2011) Auxin transport and a graviresponse in plants: relevance to ABC proteins. Biol Sci Space 25:69–75
  • Wendy AP, Murphy AS (2007) Flavonoids and auxin transport: modulators or regulators? Trends Plant Sci 12:556–563
  • Yokota T, Murofushi N, Takahashi N (1980) Extraction, purification, and identification. In: MacMillan J (ed) Hormonal regulation of development I. Encyclopedia of Plant Physiology, vol 9. Springer, Berlin, pp 113–201
  • Yoshikawa M, Shimoda H, Uemura T, Morikawa T, Kawahara Y, Matsuda H (2000) Alcohol absorption inhibitors from bay leaf (Laurus nobilis): structure-requirements of sesquiterpenes for the activity. Bioorg Med Chem 8:2071–2077
  • Yuuya S, Hagiwara H, Suzuki T, Ando M, Yamada A, Suda K, Kataoka T, Nagai K (1999) Guaianolides as immunomodulators. Synthesis and biological activities of dehydrocostus lactone, mokkolactone, eremanthin, and their derivatives. J Nat Prod 62:22–30
  • Zheng X, Miller ND, Lewis DR, Christians MJ, Lee K-H, Muday GK, Spalding EP, Vierstra RD (2011) AUXIN UP-REGULATED F-BOX PROTEIN1 regulates the cross Talk between auxin transport and cytokinin signaling during plant root growth. Plant Physiol 156:1878–1893
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