Isolation and identification of polar auxin transport inhibitors from Saussurea costus and Atractylodes japonica
Abstract
Keywords
Full Text:
PDFReferences
Muday GK, Murphy AS. An emerging model of auxin transport regulation. Plant Cell. 2002;14:293–299. https://doi.org/10.1105/tpc.140230
Scarpella E, Marcos D, Friml J, Berleth T. Control of leaf vascular patterning by polar auxin transport. Genes Dev. 2006;20:1015–1027. https://doi.org/10.1101/gad.1402406
Dhonukshe P, Tanaka H, Goh T, Ebine K, Mähönen AP, Prasad K, et al. Generation of cell polarity in plants links endocytosis, auxin distribution and cell fate decisions. Nature. 2008;456:962–967. https://doi.org/10.1038/nature07409
Ueda J, Miyamoto K, Uheda E, Oka M. Auxin transport and graviresponse in plants: relevance to ABC proteins, Biol Sci Space. 2011;25:69–75. https://doi.org/10.2187/bss.25.69
Ueda J, Miyamoto K, Uheda E, Oka M, Yano S, Higashibata A, et al. Close relationships between polar auxin transport and graviresponse in plants. Plant Biol. 2014;16(1 suppl): 43–49. https://doi.org/10.1111/plb.12101
Ueda J, Saniewski M, Miyamoto K. Auxins, one major plant hormone, in soil. In: Szajdak LW, editor. Bioactive compounds in agricultural soils. Cham: Springer; 2016. p. 175–206. https://doi.org/10.1007/978-3-319-43107-9_8
Adamowski M, Friml J. PIN-dependent auxin transport: action, regulation, and evolution. Plant Cell. 2015;27:20–32. https://doi.org/10.1105/tpc.114.134874
Okada K, Ueda J, Komaki MK, Bell CJ, Shimura Y. Requirement of auxin polar transport system in early stage of Arabidopsis floral bud formation. Plant Cell. 1991;3:677–684. https://doi.org/10.1105/tpc.3.7.677
Friml J, Vieten A, Sauer M, Weijers D, Schwarz H, Hamann T, et al. Efflux-dependent auxin gradients establish the apical-basal axis of Arabidopsis. Nature. 2003;426:147–153. https://doi.org/10.1038/nature02085
Brown DE, Rashotte AM, Murphy AS, Normanly J, Tague BW, Peer WA, et al. Flavonoids act as negative regulators of auxin transport in vivo in Arabidopsis. Plant Physiol. 2001;126:524–535. https://doi.org/10.1104/pp.126.2.524
Peer WA, Murphy AS. Flavonoids and auxin transport: modulators or regulators? Trends Plant Sci. 2007;12:556–563. https://doi.org/10.1016/j.tplants.2007.10.003
Arai T, Toda Y, Kato K, Miyamoto K, Hasegawa T, Yamada K, et al. Artabolide, a novel polar auxin transport inhibitor isolated from Artemisia absinthium. Tetrahedron. 2013;69:7001–7005. https://doi.org/10.1016/j.tet.2013.06.052
Ueda J, Toda Y, Kato K, Kuroda Y, Arai T, Hasegawa T, et al. Identification of dehydrocostus lactone and 4-hydroxy-β-thujone as auxin polar transport inhibitors. Acta Physiol Plant. 2013;35:2251–2258. https://doi.org/10.1007/s11738/013-1261-6
Yokota T, Murofushi N, Takahashi N. Extraction, purification, and identification. In: MacMillan J, editor. Hormonal regulation of development I. Berlin: Springer; 1980. p. 113–201. (Encyclopedia of Plant Physiology; vol 9).
Fang F, Sang S, Chen KY, Gosslau A, Ho CT, Rosen RT. Isolation and identification of cytotoxic compounds from bay leaf (Laurus nobilis). Food Chem. 2005;93:497–501. https://doi.org/10.1016/j.foodchem.2004.10.029
Chen LG, Jan YS, Tsai PW, Noimoto H, Michihara S, Myrayama C, et al. Anti-inflammatory and antinociceptive constituents of Atractyloides japonica Koizumi. J Agric Food Chem. 2016;64:2254–2262. https://doi.org/10.1021/acs.jafc.5b05841
Endo K, Hikino H. Sesquiterpenoids. LIV. Absolute configuration of eudesma-4(14),7(11)-dien-8-one. Bull Chem Soc Jpn. 1979;52:2439–3440. https://doi.org/10.1246/bcsj.52.2439
Paul A, Bawdekar AS, Joshi RS, Somasekar Rao A, Kelkar GR, Bhattacharyya SC. Terpenoids XX: examination of costus root oil. Perfumery and Essential Oil Record. 1960;15:115–120.
Somasekar Rao A, Kelkar GR, Bhattacharyya SC. Terpenoids: XXI. The structure of costunolide, a new sesquiterpene lactone from costus root oil. Tetrahedron. 1960;9:275–283.
Romo de Vivar A, Jimenez H. Structure of santamarine, a new sesquiterpene lactone. Tetrahedron. 1965;21:1741–1745. https://doi.org/10.1016/S0040-4020(01)98644-2
Joel DM, Chaudhuri SK, Plakhine D, Ziadna H, Steffens JC. Dehydrocostus lactone is exuded from sunflower roots and stimulates germination of the root parasite Orobanche cumana. Phytochemistry. 2011;72:624–634. https://doi.org/10.1016/j.phytochem.2011.01.037
Taniguchi M, Kataoka T, Suzuki H, Uramoto M, Ando M, Arao K, et al. Costunolide and dehydrocostus lactone as inhibitors of killing function of cytotoxic T lymphocytes. Biosci Biotechnol Biochem. 1995;59:2064–2067. https://doi.org/10.1271/bbb.59.2064
Yuuya S, Hagiwara H, Suzuki T, Ando M, Yamada A, Suda K, et al. Guaianolides as immunomodulators. Synthesis and biological activities of dehydrocostus lactone, mokkolactone, eremanthin, and their derivatives. J Nat Prod. 1999;62:22–30. https://doi.org/10.1021/np980092u
Matsuda H, Kagerura T, Toguchida I, Ueda H, Morikawa T, Yoshikawa M. Inhibitory effects of sesquiterpenes from bay leaf on nitric oxide production in lipopolysaccharide activated macrophages: structure requirement and role of heat shock protein induction. Life Sci. 2000;66:2151–2157. https://doi.org/10.1016/S0024-3205(00)00542-7
Yoshikawa M, Shimoda H, Uemura T, Morikawa T, Kawahara Y, Matsuda H. Alcohol absorption inhibitors from bay leaf (Laurus nobilis): structure-requirements of sesquiterpenes for the activity. Bioorg Med Chem. 2000;8:2071–2077. https://doi.org/10.1016/S0968-0896(00)00127-9
Sun CM, Syu W Jr, Don MJ, Lu JJ, Lee GH. Cytotoxic sesquiterpene lactones from the root of Saussurea lappa. J Nat Prod. 2003;66:1175–1180. https://doi.org/10.1021/np030147e
Butturini E, Cavalieri E, Carcereri de Prati A, Darra E, Rigo A, Shoji K, et al. Two naturally occurring terpenes, dehydrocostuslactone and costunolide, decrease intracellular GSH content and inhibit STAT3 activation. PLoS One. 2011;6:e20174. https://doi.org/10.1371/journal.pone.0020174
Endo J, Ogino T, Nagasawa M. Studies on the volatile oil of Asarum caulescens. Yakugaku Zasshi. 1972;92:874–878. https://doi.org/10.1248/yakushi1947.92.7_874
Nishikawa Y, Yasuda I, Watanabe Y, Seto T. Studies on the evolution of crude drugs. II. Identification of the ingredients of Atractylodes by thin-layer chromatography, gas chromatography and gas chromatography–mass spectrometry, and the physical and chemical evaluation. Syoyakugaku Zasshi. 1976;30:132–137.
Ye Y, Wang H, Chu JH, Chou GX, Chen SB, Mo H, et al. Atractylenolide II induces G1 cell-cycle arrest and apoptosis in B16 melanoma cells. J Ethnopharmacol. 2011;136:279–282. https://doi.org/10.1016/j.jep.2011.04.020
Chen R, Masson PH. Auxin transport and recycling of PIN proteins in plants. In: Šamaja J, Balška F, Menzel D, editors. Plant endocytosis. Berlin: Springer; 2005. p. 139–157. https://doi.org/10.1007/7089_009
Santelia D, Henrichs S, Vincenzetti V, Sauer M, Bigler L, Klein M, et al. Flavonoids redirect PIN-mediated polar auxin fluxes during root gravitropic responses. J Biol Chem. 2008;283:31218–31226. https://doi.org/10.1074/jbc.M710122200
DOI: https://doi.org/10.5586/aa.1700
|
|
|