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Phytochemistry

Title:		"Ryecyanatines A and B and ryecarbonitrilines A and B, substituted cyanatophenol, cyanatobenzo[1,3]dioxole, and benzo[1,3]dioxolecarbonitriles from rye (Secale cereale L.) root exudates: Novel metabolites with allelopathic activity on Orobanche seed germination and radicle growth"
Author(s):		Cimmino A; Fernandez-Aparicio M; Avolio F; Yoneyama K; Rubiales D; Evidente A;
Address:		"Dipartimento di Scienze Chimiche, Universita di Napoli Federico II, Complesso Universitario Monte S. Angelo, Via Cintia, 4, 80126 Napoli, Italy. Utsunomiya University, Weed Science Center, Utsunomiya, Tochigi 321-8505, Japan; INRA, UMR1347 Agroecologie, BP 86510, F-21000 Dijon, France. Utsunomiya University, Weed Science Center, Utsunomiya, Tochigi 321-8505, Japan. Institute for Sustainable Agriculture, CSIC, Apdo. 4084, 14080 Cordoba, Spain. Dipartimento di Scienze Chimiche, Universita di Napoli Federico II, Complesso Universitario Monte S. Angelo, Via Cintia, 4, 80126 Napoli, Italy. Electronic address: evidente@unina.it"
Journal Title:		Phytochemistry
Year:		2015
Volume:		20141124
Issue:
Page Number:		57 - 65
DOI:		10.1016/j.phytochem.2014.10.034
ISSN/ISBN:		1873-3700 (Electronic) 0031-9422 (Linking)
Abstract:		"Orobanche and Phelipanche species (the broomrapes) are root parasitic plants, some of which represent serious weed problems causing heavy yield losses on important crops. Current control relies on the use of certain agronomic practices, resistant crop varieties, and herbicides, albeit success has been marginal. Agronomic practices such as the use of allelopathic species in intercropping or cover crops, or the use of direct seedling over residues of allelopathic species incorporate the principle of allelopathy exerted by molecules exuded from roots or released by crop residues to control broomrapes. In addition, the isolation of natural substances from root exudates of plants with potential to inhibit broomrape development opens the door to the design of new herbicides based on natural and benign sources. Ryecyanatines A and B and ryecarbonitrilines A and B, the first new substituted cyanatophenol, substituted cyanatobenzo[1,3]dioxole, and the latter two new substituted benzo[1,3]dioxolecarbonitriles were isolated from rye (Secale cereale L.) root exudates. They were characterized as 4-cyanato-2-methoxyphenol, 2-cyanato-benzo[1,3]dioxole, 2-methoxybenzo[1,3]dioxole-5-carbonitrile and benzo[1,3]dioxole-2-carbonitrile by spectroscopic (essentially NMR and HRESI MS spectra) methods. These compounds were investigated for allelopathic activity on Orobanche germination and development. Ryecarbonitriline A induced germination of Orobanche cumana seeds, and this germination can be considered as suicidal because O. cumana does not parasite rye roots and cannot survive without host resources beyond germination stage. In addition, ryecyanatine A promotes a rapid cessation of O. cumana, Orobanche crenata and Orobanche minor radicle growth with the promotion of a layer of papillae at the radicle tip in O. cumana and O. crenata hampering the contact of the parasite to the host. Ryecarbonitriline B also displayed the same activity although being less active than ryecyanatine A and mainly restricted to O. cumana"
Keywords:		Allelopathy Benzodioxoles/*chemistry/isolation & purification Germination/*drug effects Herbicides/chemistry/isolation & purification Molecular Structure Nitriles/chemistry/isolation & purification Orobanche/*drug effects Phenols/chemistry/isolation & pur;
Notes:		"MedlineCimmino, Alessio Fernandez-Aparicio, Monica Avolio, Fabiana Yoneyama, Koichi Rubiales, Diego Evidente, Antonio eng Research Support, Non-U.S. Gov't England 2014/12/04 Phytochemistry. 2015 Jan; 109:57-65. doi: 10.1016/j.phytochem.2014.10.034. Epub 2014 Nov 24"