Sphenostylisins A-K, Bioactive Modified Isoflavonoid Constituents of the Root Bark of Sphenostylis marginata ssp. erecta
| Autor: | Norman R. Farnsworth, Chenglong Li, Ulyana Muñoz-Acuña, Djaja D. Soejarto, Ye Deng, Heebyung Chai, T E Chagwedera, Li Pan, Esperanza J. Carcache de Blanco, Chunhua Yuan, Jie Li, Hongshan Lai, A. Douglas Kinghorn |
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| Jazyk: | angličtina |
| Rok vydání: | 2013 |
| Předmět: |
Circular dichroism
Magnetic Resonance Spectroscopy biology Chemistry Stereochemistry Plant Extracts Circular Dichroism Organic Chemistry Absolute configuration Nuclear magnetic resonance spectroscopy biology.organism_classification Isoflavones Article Isoflavonoid visual_art visual_art.visual_art_medium Organic chemistry Bark Sphenostylisin-C Sphenostylis |
| Popis: | Sphenostylisins A–C (1–3), three complex dimeric compounds representing two novel carbon skeletons, along with an additional eight new compounds, sphenostylisins D–K (4–11), were isolated from the active chloroform-soluble extract of the root bark of Sphenostylis marginata ssp. erecta using a bioactivity-guided isolation approach. The structures were elucidated by means of detailed spectroscopic analysis, including NMR and HRESIMS analysis, and tandem MS fragmentation was utilized to further support the structures of 1–3. The absolute configuration of sphenostylisin C (3) was established by electronic circular dichroism analysis. Plausible biogenetic relationships between the modified isoflavonoids 1–11 are proposed, and a cyclization reaction of 9 was conducted to support one of the biogenetic proposals made. All of these pure isolates were evaluated against a panel of in vitro bioassays, and among the results obtained, sphenostylisin A (1) was found to be a very potent NF-κB inhibitor (IC50 = 6 nM). |
| Databáze: | OpenAIRE |
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