Phytotoxic Withanolides from Jaborosa rotacea

Twelve new withanolides were isolated from the aerial part of Jaborosa rotacea: five had a spiranoid delta-lactone (1-5); one contained a 26,12-delta-lactone and a C-12-C-23 bond (6); five corresponded to trechonolide-type withanolides with configuration at C-23 opposite of those previously isolated...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2006-05, Vol.69 (5), p.783-789
Main Authors: NICOTRA, Viviana E., RAMACCIOTTI, Natalia S., GIL, Roberto R., OBERTI, Juan C., FERESIN, Gabriela E., GUERRERO, Cecilia A., BAGGIO, Ricardo F., GARLAND, M. Teresa, BURTON, Gerardo
Format: Article
Language:English
Subjects:
Argentina
Biological and medical sciences
Crystallography, X-Ray
Ergosterol - analogs & derivatives
Ergosterol - chemistry
Ergosterol - isolation & purification
Ergosterol - pharmacology
General pharmacology
Lactuca - drug effects
Lactuca - growth & development
Medical sciences
Molecular Conformation
Molecular Structure
Phalaris - drug effects
Phalaris - growth & development
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Seedlings - drug effects
Seedlings - growth & development
Solanaceae - chemistry
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Summary:Twelve new withanolides were isolated from the aerial part of Jaborosa rotacea: five had a spiranoid delta-lactone (1-5); one contained a 26,12-delta-lactone and a C-12-C-23 bond (6); five corresponded to trechonolide-type withanolides with configuration at C-23 opposite of those previously isolated (7, 8, 10-12); two of these have an additional oxido-bridge between C-21 and C-24; finally a withanolide with a hemiketal ring formed between a 21-hydroxyl and a 12-ketone (13) and the closely related jaborosalactone R were also isolated. New compounds were fully characterized by a combination of spectroscopic methods (1D and 2D NMR and MS). The structures of the spiranoid withanolide and of the epimer of trechonolide A were confirmed by X-ray diffraction studies. Compounds 4, 5, 6, and 8 showed selective phytotoxicity toward monocotyledoneous and dicotyledoneous species.
ISSN:0163-3864
1520-6025
DOI:10.1021/np0600090