Avenaol, a germination stimulant for root parasitic plants from Avena strigosa

Hyun Il Kim; Takaya Kisugi; Pichit Khetkam; Xiaonan Xie; Kaori Yoneyama; Kenichi Uchida; Takao Yokota; Takahito Nomura; Christopher S P McErlean; Koichi Yoneyama

doi:10.1016/j.phytochem.2014.03.030

Avenaol, a germination stimulant for root parasitic plants from Avena strigosa

Phytochemistry. 2014 Jul:103:85-88. doi: 10.1016/j.phytochem.2014.03.030. Epub 2014 Apr 23.

Authors

Affiliations

¹ Weed Science Center, Utsunomiya University, 350 Mine-machi, Utsunomiya 321-8505, Japan; United Graduate School of Agriculture, Tokyo University of Agriculture and Technology, 3-8-1 Harumi-cho, Fuchu, Tokyo 183-8538, Japan.
² Weed Science Center, Utsunomiya University, 350 Mine-machi, Utsunomiya 321-8505, Japan.
³ Department of Biosciences, Teikyo University, 1-1 Toyosatodai, Utsunomiya 320-8551, Japan.
⁴ School of Chemistry, The University of Sydney, NSW 2006, Australia.
⁵ Weed Science Center, Utsunomiya University, 350 Mine-machi, Utsunomiya 321-8505, Japan. Electronic address: yoneyama@cc.utsunomiya-u.ac.jp.

PMID: 24768285
DOI: 10.1016/j.phytochem.2014.03.030

Abstract

Root exudates from the allelopathic plant, black oat (Avena strigosa Schreb.), were found to contain at least six different germination stimulants for root parasitic plants, but no known strigolactones (SLs). One of these germination stimulants was purified and named avenaol. Its HR-ESI-TOFMS analysis indicated that the molecular formula of avenaol is C20H24O7, and thus it contains an additional carbon compared with known C19-SLs. Its structure was determined as 5-((E)-(5-(3-hydroxy-1,5,5-trimethyl-2-oxobicyclo[4.1.0]heptan-7-yl)-2-oxodihydrofuran-3(2H)-ylidene)methoxy)-3-methylfuran-2(5H)-one, by 1D and 2D NMR spectroscopy, and ESI- and EI-MS spectrometry. Although avenaol contains the C-D moiety, the common structural feature for all known SLs, it lacks the B ring and has an additional carbon atom between the A and C rings. Avenaol is a potent germination stimulant of Phelipanche ramosa seeds, but only a weak stimulant for seeds of Striga hermonthica and Orobanche minor.

Keywords: Avena strigosa; Avenaol; Black oat; Orobanchaceae; Orobanche minor; Phelipanche ramosa; Poaceae; Striga hermonthica; Strigolactone.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Germination / drug effects*
Lactones / chemistry*
Lactones / pharmacology*
Orobanche / drug effects
Plant Exudates / chemistry*
Plant Exudates / pharmacology
Plant Roots / chemistry*
Poaceae / chemistry*
Striga / drug effects

Substances

Lactones
Plant Exudates