Unprecedented Quassinoids with Promising Biological Activity from Harrisonia perforata.

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. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Xin Fang, Ying Tong Di, Yu Zhang, Zhi Ping Xu, Yang Lu, Qian Qian Chen, Qi Tai Zheng, Xiao Jiang Hao. Unprecedented Quassinoids with Promising Biological Activity from Harrisonia perforata. Angewandte Chemie (International ed. in English). 2015 May 4;54(19):5592-5

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PMID: 25810025

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