Sphenostylisins A鈥揔: Bioactive Modified Isoflavonoid Constituents of the Root Bark of Sphenostylis marginata ssp. erecta

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• 作者：Jie Li ; Li Pan ; Ye Deng ; Ulyana Mu帽oz-Acu帽a ; Chunhua Yuan ; Hongshan Lai ; Heebyung Chai ; Tangai E. Chagwedera ; Norman R. Farnsworth ; Esperanza J. Carcache de Blanco ; Chenglong Li ; Djaja D. Soejarto ; A. Douglas Kinghorn
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：October 18, 2013
• 年：2013
• 卷：78
• 期：20
• 页码：10166-10177
• 全文大小：495K
• 年卷期：v.78,no.20(October 18, 2013)
• ISSN：1520-6904

文摘

Sphenostylisins A鈥揅 (1鈥?b>3), three complex dimeric compounds representing two novel carbon skeletons, along with an additional eight new compounds, sphenostylisins D鈥揔 (4鈥?b>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鈥?b>3. The absolute configuration of sphenostylisin C (3) was established by electronic circular dichroism analysis. Plausible biogenetic relationships between the modified isoflavonoids 1鈥?b>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-魏B inhibitor (IC₅₀ = 6 nM).