Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 19, Pages 5592-5595Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201412126
Keywords
biosynthetic pathways; insecticidal activity; natural products; nicotinic acetylcholine receptors; structure elucidation
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Funding
- National Science Foundation of China [21432010]
- Science Foundation of Yunnan [2014A050]
- Technological leading talent project of Yunnan
- Xibuzhiguang Project
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Perforalactone A (1), a new 20S quassinoid with a unique cagelike 2,4-dioxaadamantane ring system and a migrated side chain, was isolated from the plant Harrisonia perforata together with two biosynthetically related new quassinoids. The structures of these natural products were elucidated by NMR spectroscopy, X-ray diffraction analysis, computational modeling, and the CD excitation chirality method. The compounds exhibited notable biological properties, including insecticidal activity against Aphis medicaginis Koch and antagonist activity at the nicotinic acetylcholine receptor of Drosophila melanogaster. The structural features of these compounds may be related to their promising biological characteristics. Their biosynthesis and an alternative origin of quassinoid-type natural products are also discussed.
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