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

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Abstract

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.

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Abbreviations

GC-MS:

Combined gas–liquid chromatography–mass spectrometry

HFCA:

9-Hydroxyfluorene-9-carboxylic acid

1H-NMR:

Proton nuclear magnetic resonance

IAA:

Indole-3-acetic acid

NPA:

N-(1-Naphthyl)phthalamic acid

PCIB:

p-Chlorophynoxyisobutyric acid

TIBA:

2,3,5-Triiodobenzoic acid

TLC:

Thin-layer chromatography

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Acknowledgments

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

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Authors and Affiliations

  1. Graduate School of Science, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka, 599-8531, Japan

    Junichi Ueda, Yuta Toda, Kiyotaka Kato, Yuichi Kuroda & Eiji Uheda

  2. Graduate School of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki, 305-8577, Japan

    Tsukasa Arai, Tsuyoshi Hasegawa, Hideyuki Shigemori & Koji Hasegawa

  3. Koshiro Co. Ltd., 57 Wakamiya-suji, Namikawa, Oui-cho, Kameoka, Kyoto, 621-0013, Japan

    Jinichiro Kitagawa

  4. Faculty of Liberal Arts and Sciences, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka, 599-8531, Japan

    Kensuke Miyamoto

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  1. Junichi Ueda
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  2. Yuta Toda
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  3. Kiyotaka Kato
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Correspondence to Junichi Ueda.

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Communicated by P. K. Nagar.

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Ueda, J., Toda, Y., Kato, K. et al. Identification of dehydrocostus lactone and 4-hydroxy-β-thujone as auxin polar transport inhibitors. Acta Physiol Plant 35, 2251–2258 (2013). https://doi.org/10.1007/s11738-013-1261-6

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  • DOI: https://doi.org/10.1007/s11738-013-1261-6

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