title: Unprecedented Quassinoids with Promising Biological Activity from Harrisonia perforata.
abstract: 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.
authors: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan (PR China).
authors: Xin
authors: X
authors: Fang
authors: Ying Tong
authors: YT
authors: Di
authors: Yu
authors: Y
authors: Zhang
authors: Zhi Ping
authors: ZP
authors: Xu
authors: Yang
authors: Y
authors: Lu
authors: Qian Qian
authors: QQ
authors: Chen
authors: Qi Tai
authors: QT
authors: Zheng
authors: Xiao Jiang
authors: XJ
authors: Hao
mesh_terms: D000818:Animals; D001688:Biological Products / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D001517:Coleoptera / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D004331:Drosophila melanogaster / Q000737:chemistry / Q000378:metabolism; D007306:Insecticides / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D008968:Molecular Conformation; D036702:Quassins / Q000096:biosynthesis / Q000737:chemistry / Q000494:pharmacology*; D011978:Receptors, Nicotinic / Q000378:metabolism*; D029641:Simaroubaceae / Q000737:chemistry* / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D001688:Biological Products; D007306:Insecticides; D036702:Quassins; D011978:Receptors, Nicotinic
keywords: biosynthetic pathways; insecticidal activity; natural products; nicotinic acetylcholine receptors; structure elucidation