Phenols, Acetylenes, and Sesquiterpene Lactones from Inulanthera nuda
✍ Scribed by Stefan Gafner; Jean-Luc Wolfender; Kurt Hostettmann; Helen Stoeckli-Evans; Stephen Mavi
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- German
- Weight
- 146 KB
- Volume
- 81
- Category
- Article
- ISSN
- 0018-019X
No coin nor oath required. For personal study only.
✦ Synopsis
Five new compounds, the sesquiterpene lactones 1 and 2, the 2H-pyran-2-one 9, the flavone glycoside 10, and the organic diacid 11 were isolated from the CH 2 Cl 2 extract (1 and 2) and from the BuOH part of the MeOH extract (9 ± 11) of the aerial parts of Inulanthera nuda KÌllersjÎ (Asteraceae). The structures were established by spectroscopic methods, including UV, IR, EI-MS, D/CI-MS and TSP-MS, 1 H-and 13 C-NMR as well as twodimensional NMR techniques. The sesquiterpene lactones were identified as 1a,4b,10b-trihydroxyguaia-2,11(13)-dieno-12,6a-lactone (1) and 4b,10b-dihydroxy-1a-methoxyguaia-2,11(13)-dieno-12,6a-lactone (2), while 9 was found to be 4-(b-d-glucopyranosyloxy)-6-methyl-2H-pyran-2-one, 10 was determined as luteolin 7-(2''-O-acetyl-b-d-glucuronoside) and 11 as (Z)-2-(4-hydroxybenzyl)butenedioic acid. The new compounds were accompanied by six more compounds (3 ± 8) from the CH 2 Cl 2 extract and ten compounds from the BuOH extract (including 12 ± 16). Compounds 3 and 4 were identified as (E)-and (Z)-O-acetyldendranthemenol, while the structures of 5 ± 8 were elucidated as the flavones salvigenin, 5-hydroxy-3',4',6,7-tetramethoxyflavone, eupatorin, and cirsilineol, respectively, from their spectroscopic data (EI-and D/CI-MS, UV, 1 H-and 13 C-NMR). Compounds 12 ± 16 were determined as scopolin, maltol 3-glucoside, and the flavone glycosides luteolin 7-glucuronide, apigenin 7-glucuronide, and scutellarein 7-glucuronide based on spectral evidences (D/ CI-and TSP-MS, UV, 1 H-and 13 C-NMR). The additional five compounds from the BuOH extract were identified on-line by HPLC-MS as chlorogenic acid, 3,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 4,5dicaffeoylquinic acid, and 3,4-dicaffeoylisoquinic acid. The identification was based on comparison of retention times and UV and mass spectra with authentic samples.
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## Abstract From the aerial parts of __A. melanolepis__, two new sesquiterpene lactones, melanolepin B ( = 1__α__,4__β__,8__α__‐trihydroxyeudesm‐11(13)‐en‐12,6__α__‐olide; **1**) and melanolepin C (= 1__α__,10__β__‐epoxy‐8__β__‐hydroxygermacra‐4(15),11(13)‐dien‐12,6__α__‐olide; **2**), were isolate