Sesquiterpenes from Oplopanax horridus

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• 作者：Taichi Inui ; Yuehong Wang ; Dejan Nikolic ; David C. Smith ; Scott G. Franzblau ; Guido F. Pauli
• 刊名：Journal of Natural Products
• 出版年：2010
• 出版时间：April 23, 2010
• 年：2010
• 卷：73
• 期：4
• 页码：563-567
• 全文大小：132K
• 年卷期：v.73,no.4(April 23, 2010)
• ISSN：1520-6025

文摘

From the anti-TB active fractions of the inner stem bark of Oplopanax horridus, two new heterocyclic nerolidol derivatives, 3,10-epoxy-3,7,11-trimethyldodeca-1,6-dien-11-ol, named neroplomacrol (1), and rel-(3S,6R,7S,10R)-7,10-epoxy-3,7,11-trimethyldodec-1-ene-3,6,11-triol, named neroplofurol (2), were isolated together with oplopandiol (3), falcarindiol (4), and sesamin (5). Extensive spectroscopic analysis revealed that 1 possesses a novel 3,10-oxanonacyclic ring system. Computer-iterated full spin system analysis led to the generation of ¹H NMR fingerprints that will facilitate future dereplication of analogues by providing characteristic spin−spin coupling patterns. The full spin analysis of 5 revealed asymmetric coupling patterns among the chemically equivalent spins, thus confirming the magnetic asymmetry of 5. It was further demonstrated that ¹H NMR fingerprints and MS data enable dereplication of isolates at a submilligram levels including their relative configuration. Countercurrent concentration of the anti-TB activity of the ethnobotanical O. horridus versus the Mycobacterium tuberculosis Erdman strain led to polyynes 3 and 4 as main anti-TB active principles. Their synergistic behavior is linked to a complex fraction containing the new nerolidiol sesquiterpenes, 1 and 2, as phytochemical marker compounds.