Acta Physiologiae Plantarum

, Volume 35, Issue 7, pp 2251–2258 | Cite as

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

  • Junichi UedaEmail author
  • Yuta Toda
  • Kiyotaka Kato
  • Yuichi Kuroda
  • Tsukasa Arai
  • Tsuyoshi Hasegawa
  • Hideyuki Shigemori
  • Koji Hasegawa
  • Jinichiro Kitagawa
  • Kensuke Miyamoto
  • Eiji Uheda
Original Paper


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 μg/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.


Auxin polar transport Dehydrocostus lactone 4-Hydroxy-β-thujone Inhibitor Asteraceae 



Combined gas–liquid chromatography–mass spectrometry


9-Hydroxyfluorene-9-carboxylic acid


Proton nuclear magnetic resonance


Indole-3-acetic acid


N-(1-Naphthyl)phthalamic acid


p-Chlorophynoxyisobutyric acid


2,3,5-Triiodobenzoic acid


Thin-layer chromatography



This work was partially supported by JSPS KAKENHI Grant Number 23510260.


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Copyright information

© Franciszek Górski Institute of Plant Physiology, Polish Academy of Sciences, Kraków 2013

Authors and Affiliations

  • Junichi Ueda
    • 1
    Email author
  • Yuta Toda
    • 1
  • Kiyotaka Kato
    • 1
  • Yuichi Kuroda
    • 1
  • Tsukasa Arai
    • 2
  • Tsuyoshi Hasegawa
    • 2
  • Hideyuki Shigemori
    • 2
  • Koji Hasegawa
    • 2
  • Jinichiro Kitagawa
    • 3
  • Kensuke Miyamoto
    • 4
  • Eiji Uheda
    • 1
  1. 1.Graduate School of Science, Osaka Prefecture UniversitySakaiJapan
  2. 2.Graduate School of Life and Environmental Sciences, University of TsukubaTsukubaJapan
  3. 3.Koshiro Co. Ltd.KameokaJapan
  4. 4.Faculty of Liberal Arts and Sciences, Osaka Prefecture UniversitySakaiJapan

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