Fabacyl acetate, a germination stimulant for root parasitic plants from Pisum sativum.
A germination stimulant, fabacyl acetate, was purified from root exudates of pea (Pisum sativum L.) and its structure was determined as ent-2'-epi-4a,8a-epoxyorobanchyl acetate [(3aR,4R,4aR,8bS,E)-4a,8a-epoxy-8,8-dimethyl-3-(((R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yloxy)methylene)-2-oxo-3,3a,4,5,6,7,8,8b-decahydro-2H-indeno[1,2-b]furan-4-yl acetate], by 1D and 2D NMR spectroscopic, ESI- and EI-MS spectrometric, X-ray crystallographic analyses, and by comparing the (1)H NMR spectroscopic data and relative retention times (RR(t)) in LC-MS and GC-MS with those of synthetic standards prepared from (+)-orobanchol and (+)-2'-epiorobanchol. The (1)H NMR spectroscopic data and RR(t) of fabacyl acetate were identical with those of an isomer prepared from (+)-2'-epiorobanchol except for the opposite sign in CD spectra. This is the first natural ent-strigolactone containing an epoxide group. Fabacyl acetate was previously detected in root exudates of other Fabaceae plants including faba bean (Vicia faba L.) and alfalfa (Medicago sativa L.).
Xie
Xiaonan
X
Weed Science Center, Utsunomiya University, 350 Mine-machi, Utsunomiya 321-8505, Japan.
Yoneyama
Kaori
K
Harada
Yuta
Y
Fusegi
Norio
N
Yamada
Yoichi
Y
Ito
Satoshi
S
Yokota
Takao
T
Takeuchi
Yasutomo
Y
Yoneyama
Koichi
K
D000085:Acetates / Q000737:chemistry* / Q000378:metabolism*; D018360:Crystallography, X-Ray; D018525:Germination; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D031672:Orobanche / Q000254:growth & development / Q000378:metabolism; D018517:Plant Roots / Q000737:chemistry* / Q000254:growth & development* / Q000378:metabolism
D000085:Acetates