Spiranoid Withanolides from Jaborosa runcinata and Jaborosa araucana
1996; American Chemical Society; Volume: 59; Issue: 8 Linguagem: Inglês
10.1021/np960210i
ISSN1520-6025
AutoresAdriana M. Cirigliano, Adriana S. Veleiro, Gloria M. Bonetto, Juan C. Oberti, Gerardo Burton,
Tópico(s)Pharmacological Effects of Medicinal Plants
ResumoFrom 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.
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