Avenaol, a germination stimulant for root parasitic plants from Avena strigosa.
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.
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.
Hyun Il
HI
Kim
Weed Science Center, Utsunomiya University, 350 Mine-machi, Utsunomiya 321-8505, Japan.
Takaya
T
Kisugi
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.
Pichit
P
Khetkam
Weed Science Center, Utsunomiya University, 350 Mine-machi, Utsunomiya 321-8505, Japan.
Xiaonan
X
Xie
Weed Science Center, Utsunomiya University, 350 Mine-machi, Utsunomiya 321-8505, Japan.
Kaori
K
Yoneyama
Department of Biosciences, Teikyo University, 1-1 Toyosatodai, Utsunomiya 320-8551, Japan.
Kenichi
K
Uchida
Department of Biosciences, Teikyo University, 1-1 Toyosatodai, Utsunomiya 320-8551, Japan.
Takao
T
Yokota
Weed Science Center, Utsunomiya University, 350 Mine-machi, Utsunomiya 321-8505, Japan.
Takahito
T
Nomura
School of Chemistry, The University of Sydney, NSW 2006, Australia.
Christopher S P
CSP
McErlean
Weed Science Center, Utsunomiya University, 350 Mine-machi, Utsunomiya 321-8505, Japan. Electronic address: yoneyama@cc.utsunomiya-u.ac.jp.
Koichi
K
Yoneyama
D018525:Germination / Q000187:drug effects*; D007783:Lactones / Q000737:chemistry* / Q000494:pharmacology*; D031672:Orobanche / Q000187:drug effects; D053147:Plant Exudates / Q000737:chemistry* / Q000494:pharmacology; D018517:Plant Roots / Q000737:chemistry*; D006109:Poaceae / Q000737:chemistry*; D034362:Striga / Q000187:drug effects
D007783:Lactones; D053147:Plant Exudates
Avena strigosa; Avenaol; Black oat; Orobanchaceae; Orobanche minor; Phelipanche ramosa; Poaceae; Striga hermonthica; Strigolactone