Isolation and structure elucidation of three neo-clerodane diterpenes from Teucrium fruticans L. (LABIATAE).
Recently, the isolation from Teucrium fruticans of neo-clerodanes, namely 7beta-hydroxyfruticolone, 11-hydroxyfruticolone, deacetylfruticolone and 6-acetyl-10-hydroxyteucjaponin B, in addition to fruticolone, isofruticolone and 8beta-hydroxyfruticolone (three out of the four previously reported ones), and 6-acetylteucjaponin B (isolated from T. scordium and T. grisebachii) was reported. Minor compounds presumably of neo-clerodane nature were shown by HPLC analysis on a new extract. Three new compounds, difuranofruticol, deoxyfruticolone and 10-hydroxyteucjaponin B, and the known 7,8-didehydrofruticolone were unambiguously elucidated based on extensive NMR spectral studies (one- and two-dimensional experiments). The compounds were assayed for their antifeedant activity against Spodoptera littoralis and for their antifungal activity against Rhizoctonia solani. Compounds 9-11 showed low antifeedant activity and the feeding ratio of 12 was moderate-low. None of the tested compounds displayed significant activity against R. solani.
Coll
Josep
J
Instituto de Investigaciones Químicas y Ambientales de Barcelona, Josep Pascual Vila, Departamento de Química Orgánica Biológica, Consejo Superior de Investigaciones Científicas, Jordi Girona 18-26, 08034 Barcelona, Spain. jctqob@iiqab.csic.es
Tandrón
Yudelsy
Y
D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D045785:Diterpenes, Clerodane / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D005247:Feeding Behavior / Q000187:drug effects; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012232:Rhizoctonia / Q000187:drug effects; D018411:Spodoptera / Q000187:drug effects / Q000502:physiology; D013329:Structure-Activity Relationship; D031367:Teucrium / Q000737:chemistry*
D000935:Antifungal Agents; D045785:Diterpenes, Clerodane; D007306:Insecticides