Journal
JOURNAL OF NATURAL PRODUCTS
Volume 77, Issue 1, Pages 148-153Publisher
AMER CHEMICAL SOC
DOI: 10.1021/np400886s
Keywords
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Funding
- NSF [DEB 1145609]
- University of Nevada, Reno
- Direct For Biological Sciences
- Division Of Environmental Biology [1145609] Funding Source: National Science Foundation
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The known prenylated benzoic acid derivative 3-geranyl-4-hydroxy-5-(3 '',3 ''-dimethylallyl)benzoic acid (1) and two new chromane natural products were isolated from the methanolic extract of the leaves of Piper kelleyi Tepe (Piperaceae), a midcanopy tropical shrub that grows in lower montane rain forests in Ecuador and Peru. Structure determination using ID and 2D NMR analysis led to the structure of the chromene 2 and to the reassignment of the structure of cumanensic acid as 4, an isomeric chromene previously isolated from Piper gaudichaudianum. The structure and relative configuration of new chromane 3 was determined using 1D and 2D NMR spectroscopic analysis and was found to be racemic by ECD spectropolarimetry. The biological activity of 1-3 was evaluated against a lab colony of the generalist caterpillar Spodoptera exigua (Noctuidae), and low concentrations of 2 and 3 were found to significantly reduce fitness. Further consideration of the biosynthetic relationship of the three compounds led to the proposal that 1 is converted to 2 via an oxidative process, whereas 3 is produced through hetero-[4+2] dimerization of a quinone methide derived from the chromene 2.
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