Colonization of the roots of various tobacco species and cultivars (Nicotiana glauca Grah., N. longiflora Cav., N. rustica L., N. tabacum L., N. tabacum L. cv. Samsun NN, N. sanderae hort. Sander ex Wats.) as well as tomato plants (Lycopersicon esculentum L. cv. Moneymaker) by the arbuscular mycorrhizal fungus Glomus intraradices Schenck and Smith resulted in the accumulation of several glycosylated C13 cyclohexenone derivatives. Eight derivatives were isolated from the mycorrhizal roots by preparative high performance liquid chromatography (HPLC) and spectroscopically identified (MS and NMR) as mono-, di- and triglucosides of 6-(9-hydroxybutyl)-1,1,5-trimethyl-4-cyclohexen-3-one and monoglucosides of 6-(9-hydroxybutyl)-1,5-dimethyl-4-cyclohexen-3-one-1-carboxylic acid and 6-(9-hydroxybutyl)-1,1-dimethyl-4-cyclohexen-3-one-5-carboxylic acid. In contrast to the induced cyclohexenone derivatives, accumulation of the coumarins scopoletin and its glucoside (scopolin) in roots of N. glauca Grah. and N. tabacum L. cv. Samsun NN, was markedly suppressed.
tobacco; tomato; Solanaceae; Glomus intraradices; arbuscular mycorrhiza; cyclohexenone derivatives; isoprenoids; coumarins
NCBI PubMed ID: 10939350Publication DOI: 10.1016/s0031-9422(00)00047-9Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: dstrack@ipb.uni-halle.de
Institutions: Leibniz-Institut für Pflanzenbiochemie (IPB), Abteilung Sekundärstoffwechsel, Halle (Saale), Germany, Gesellschaft für Biotechnologische Forschung (GBF), Braunschweig, Germany
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, acid hydrolysis, HPLC, extraction, evaporation
Found