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

Avenaol, a germination stimulant for root parasitic plants, was isolated from root exudates of an allelopathic grass Avena strigosa. Avenaol is a C20 stimulant structurally related to strigolactones and highly active on Phelipanche ramosa. [Display omitted] •Allelopathic grass Avena strigosa produce...

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Published in:Phytochemistry (Oxford) 2014-07, Vol.103, p.85-88
Main Authors: Kim, Hyun Il, Kisugi, Takaya, Khetkam, Pichit, Xie, Xiaonan, Yoneyama, Kaori, Uchida, Kenichi, Yokota, Takao, Nomura, Takahito, McErlean, Christopher S.P., Yoneyama, Koichi
Format: Article
Language:English
Subjects:
Avena strigosa
Avenaol
Black oat
Germination - drug effects
Lactones - chemistry
Lactones - pharmacology
Orobanchaceae
Orobanche - drug effects
Orobanche minor
Phelipanche ramosa
Plant Exudates - chemistry
Plant Exudates - pharmacology
Plant Roots - chemistry
Poaceae
Poaceae - chemistry
Striga - drug effects
Striga hermonthica
Strigolactone
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Summary:Avenaol, a germination stimulant for root parasitic plants, was isolated from root exudates of an allelopathic grass Avena strigosa. Avenaol is a C20 stimulant structurally related to strigolactones and highly active on Phelipanche ramosa. [Display omitted] •Allelopathic grass Avena strigosa produces no known strigolactones.•Avenaol is a C20 germination stimulant structurally related to strigolactones.•Avenaol is more active on Phelipanche ramosa, but less active on Striga hermonthica and Orobanche minor. 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.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2014.03.030