Phytotoxic withanolides from Jaborosa rotacea
Twelve new withanolides were isolated from the aerial part of Jaborosa rotacea: five had a spiranoid δ-lactone (1-5); one contained a 26,12-δ-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,...
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2006
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v69_n5_p783_Nicotra http://hdl.handle.net/20.500.12110/paper_01633864_v69_n5_p783_Nicotra |
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paper:paper_01633864_v69_n5_p783_Nicotra2023-06-08T15:14:17Z Phytotoxic withanolides from Jaborosa rotacea Burton, Gerardo herbicide jaborosalactone 29 [(20s,22s) 6alpha chloro 12alpha,22 epoxy 5beta,12beta,17beta trihydroxy 1 oxo witha 2,24 dien 26,22 olide] jaborosalactone 30 [(20s,22s) 12alpha 22 epoxy 6beta,12beta,17beta trihydroxy 1 oxo witha 2,4,24 (trien 26,22 olide] jaborosalactone 31 [(20s,23r) 12beta,26 epoxy 5alpha,6beta,17beta trihydroxy 26 oxo 12alpha,23 cycloergosta 2,24 (dien 1,22 dione] jaborosalactone 33 [(22s,23r) 12alpha,22 epoxy 5alpha,6beta,12beta,17beta tetrahydroxy 1 oxo witha 2,24 dien 26,23 olide] unclassified drug withanolide angiosperm article Jaborosa rotacea nuclear magnetic resonance phytotoxicity spectroscopy X ray diffraction Argentina Crystallography, X-Ray Ergosterol Lettuce Molecular Conformation Molecular Structure Phalaris Seedling Solanaceae Jaborosa Twelve new withanolides were isolated from the aerial part of Jaborosa rotacea: five had a spiranoid δ-lactone (1-5); one contained a 26,12-δ-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. © 2006 American Chemical Society and American Society of Pharmacognosy. Fil:Burton, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2006 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v69_n5_p783_Nicotra http://hdl.handle.net/20.500.12110/paper_01633864_v69_n5_p783_Nicotra |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
herbicide jaborosalactone 29 [(20s,22s) 6alpha chloro 12alpha,22 epoxy 5beta,12beta,17beta trihydroxy 1 oxo witha 2,24 dien 26,22 olide] jaborosalactone 30 [(20s,22s) 12alpha 22 epoxy 6beta,12beta,17beta trihydroxy 1 oxo witha 2,4,24 (trien 26,22 olide] jaborosalactone 31 [(20s,23r) 12beta,26 epoxy 5alpha,6beta,17beta trihydroxy 26 oxo 12alpha,23 cycloergosta 2,24 (dien 1,22 dione] jaborosalactone 33 [(22s,23r) 12alpha,22 epoxy 5alpha,6beta,12beta,17beta tetrahydroxy 1 oxo witha 2,24 dien 26,23 olide] unclassified drug withanolide angiosperm article Jaborosa rotacea nuclear magnetic resonance phytotoxicity spectroscopy X ray diffraction Argentina Crystallography, X-Ray Ergosterol Lettuce Molecular Conformation Molecular Structure Phalaris Seedling Solanaceae Jaborosa |
| spellingShingle |
herbicide jaborosalactone 29 [(20s,22s) 6alpha chloro 12alpha,22 epoxy 5beta,12beta,17beta trihydroxy 1 oxo witha 2,24 dien 26,22 olide] jaborosalactone 30 [(20s,22s) 12alpha 22 epoxy 6beta,12beta,17beta trihydroxy 1 oxo witha 2,4,24 (trien 26,22 olide] jaborosalactone 31 [(20s,23r) 12beta,26 epoxy 5alpha,6beta,17beta trihydroxy 26 oxo 12alpha,23 cycloergosta 2,24 (dien 1,22 dione] jaborosalactone 33 [(22s,23r) 12alpha,22 epoxy 5alpha,6beta,12beta,17beta tetrahydroxy 1 oxo witha 2,24 dien 26,23 olide] unclassified drug withanolide angiosperm article Jaborosa rotacea nuclear magnetic resonance phytotoxicity spectroscopy X ray diffraction Argentina Crystallography, X-Ray Ergosterol Lettuce Molecular Conformation Molecular Structure Phalaris Seedling Solanaceae Jaborosa Burton, Gerardo Phytotoxic withanolides from Jaborosa rotacea |
| topic_facet |
herbicide jaborosalactone 29 [(20s,22s) 6alpha chloro 12alpha,22 epoxy 5beta,12beta,17beta trihydroxy 1 oxo witha 2,24 dien 26,22 olide] jaborosalactone 30 [(20s,22s) 12alpha 22 epoxy 6beta,12beta,17beta trihydroxy 1 oxo witha 2,4,24 (trien 26,22 olide] jaborosalactone 31 [(20s,23r) 12beta,26 epoxy 5alpha,6beta,17beta trihydroxy 26 oxo 12alpha,23 cycloergosta 2,24 (dien 1,22 dione] jaborosalactone 33 [(22s,23r) 12alpha,22 epoxy 5alpha,6beta,12beta,17beta tetrahydroxy 1 oxo witha 2,24 dien 26,23 olide] unclassified drug withanolide angiosperm article Jaborosa rotacea nuclear magnetic resonance phytotoxicity spectroscopy X ray diffraction Argentina Crystallography, X-Ray Ergosterol Lettuce Molecular Conformation Molecular Structure Phalaris Seedling Solanaceae Jaborosa |
| description |
Twelve new withanolides were isolated from the aerial part of Jaborosa rotacea: five had a spiranoid δ-lactone (1-5); one contained a 26,12-δ-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. © 2006 American Chemical Society and American Society of Pharmacognosy. |
| author |
Burton, Gerardo |
| author_facet |
Burton, Gerardo |
| author_sort |
Burton, Gerardo |
| title |
Phytotoxic withanolides from Jaborosa rotacea |
| title_short |
Phytotoxic withanolides from Jaborosa rotacea |
| title_full |
Phytotoxic withanolides from Jaborosa rotacea |
| title_fullStr |
Phytotoxic withanolides from Jaborosa rotacea |
| title_full_unstemmed |
Phytotoxic withanolides from Jaborosa rotacea |
| title_sort |
phytotoxic withanolides from jaborosa rotacea |
| publishDate |
2006 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v69_n5_p783_Nicotra http://hdl.handle.net/20.500.12110/paper_01633864_v69_n5_p783_Nicotra |
| work_keys_str_mv |
AT burtongerardo phytotoxicwithanolidesfromjaborosarotacea |
| _version_ |
1768545413628952576 |