Spiranoid withanolides from Jaborosa runcinata and Jaborosa araucana

From the aerial parts of Jaborosa runcinata six new withanolides were isolated and named jaborosalactones 1-6 (1-6). All contain a side chain with a carbon-carbon bond between C-12 of the intact steroid nucleus and C-23 and a spiranoid γ-lactone at the latter position. The additional ring thus forme...

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Detalles Bibliográficos
Autores principales: Cirigliano, A.M., Veleiro, A.S., Bonetto, G.M., Oberti, J.C., Burton, G.
Formato: JOUR
Materias:
jaborosalactone 1
jaborosalactone 2
jaborosalactone 3
jaborosalactone 4
jaborosalactone 5
jaborosalactone 6
unclassified drug
withanolide
article
biogenesis
cell transformation
drug isolation
molecular model
nonhuman
spectroscopy
structure analysis
Jaborosa araucana
Jaborosa runcinata
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_01633864_v59_n8_p717_Cirigliano
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_01633864_v59_n8_p717_Cirigliano
record_format dspace
spelling todo:paper_01633864_v59_n8_p717_Cirigliano2023-10-03T15:02:07Z Spiranoid withanolides from Jaborosa runcinata and Jaborosa araucana Cirigliano, A.M. Veleiro, A.S. Bonetto, G.M. Oberti, J.C. Burton, G. jaborosalactone 1 jaborosalactone 2 jaborosalactone 3 jaborosalactone 4 jaborosalactone 5 jaborosalactone 6 unclassified drug withanolide article biogenesis cell transformation drug isolation molecular model nonhuman spectroscopy structure analysis Jaborosa araucana Jaborosa runcinata From the aerial parts of Jaborosa runcinata six new withanolides were isolated and named jaborosalactones 1-6 (1-6). All contain a side chain with a carbon-carbon bond between C-12 of the intact steroid nucleus and C-23 and a spiranoid γ-lactone at the latter position. The additional ring thus formed has a 17(20)-ene-22-keto system. Jaborosalactones 4-6 (4-6) also contain a hydroxyl group at C-21. From the aerial parts of Jaborosa araucana were isolated the known withanolides trechonolide A (8), its 5α,6β- dihydroxy analogue jaborosotetrol (9), and the spiranoid withanolide jaborosalactone 2 (2), also isolated from J. runcinata. The stereochemistry of the spiranoid center at C-23 was determined as 23R based on NOESY NMR spectra and molecular modeling using the AM1 semiempirical method. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_01633864_v59_n8_p717_Cirigliano
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic jaborosalactone 1
jaborosalactone 2
jaborosalactone 3
jaborosalactone 4
jaborosalactone 5
jaborosalactone 6
unclassified drug
withanolide
article
biogenesis
cell transformation
drug isolation
molecular model
nonhuman
spectroscopy
structure analysis
Jaborosa araucana
Jaborosa runcinata
spellingShingle jaborosalactone 1
jaborosalactone 2
jaborosalactone 3
jaborosalactone 4
jaborosalactone 5
jaborosalactone 6
unclassified drug
withanolide
article
biogenesis
cell transformation
drug isolation
molecular model
nonhuman
spectroscopy
structure analysis
Jaborosa araucana
Jaborosa runcinata
Cirigliano, A.M.
Veleiro, A.S.
Bonetto, G.M.
Oberti, J.C.
Burton, G.
Spiranoid withanolides from Jaborosa runcinata and Jaborosa araucana
topic_facet jaborosalactone 1
jaborosalactone 2
jaborosalactone 3
jaborosalactone 4
jaborosalactone 5
jaborosalactone 6
unclassified drug
withanolide
article
biogenesis
cell transformation
drug isolation
molecular model
nonhuman
spectroscopy
structure analysis
Jaborosa araucana
Jaborosa runcinata
description From the aerial parts of Jaborosa runcinata six new withanolides were isolated and named jaborosalactones 1-6 (1-6). All contain a side chain with a carbon-carbon bond between C-12 of the intact steroid nucleus and C-23 and a spiranoid γ-lactone at the latter position. The additional ring thus formed has a 17(20)-ene-22-keto system. Jaborosalactones 4-6 (4-6) also contain a hydroxyl group at C-21. From the aerial parts of Jaborosa araucana were isolated the known withanolides trechonolide A (8), its 5α,6β- dihydroxy analogue jaborosotetrol (9), and the spiranoid withanolide jaborosalactone 2 (2), also isolated from J. runcinata. The stereochemistry of the spiranoid center at C-23 was determined as 23R based on NOESY NMR spectra and molecular modeling using the AM1 semiempirical method.
format JOUR
author Cirigliano, A.M.
Veleiro, A.S.
Bonetto, G.M.
Oberti, J.C.
Burton, G.
author_facet Cirigliano, A.M.
Veleiro, A.S.
Bonetto, G.M.
Oberti, J.C.
Burton, G.
author_sort Cirigliano, A.M.
title Spiranoid withanolides from Jaborosa runcinata and Jaborosa araucana
title_short Spiranoid withanolides from Jaborosa runcinata and Jaborosa araucana
title_full Spiranoid withanolides from Jaborosa runcinata and Jaborosa araucana
title_fullStr Spiranoid withanolides from Jaborosa runcinata and Jaborosa araucana
title_full_unstemmed Spiranoid withanolides from Jaborosa runcinata and Jaborosa araucana
title_sort spiranoid withanolides from jaborosa runcinata and jaborosa araucana
url http://hdl.handle.net/20.500.12110/paper_01633864_v59_n8_p717_Cirigliano
work_keys_str_mv AT ciriglianoam spiranoidwithanolidesfromjaborosaruncinataandjaborosaaraucana
AT veleiroas spiranoidwithanolidesfromjaborosaruncinataandjaborosaaraucana
AT bonettogm spiranoidwithanolidesfromjaborosaruncinataandjaborosaaraucana
AT obertijc spiranoidwithanolidesfromjaborosaruncinataandjaborosaaraucana
AT burtong spiranoidwithanolidesfromjaborosaruncinataandjaborosaaraucana
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