title: Involucratustones A-C: Unprecedented Sesquiterpene Dimers Containing Multiple Contiguous Quaternary Carbons from Stahlianthus involucratus.
abstract: Involucratustones A-C (1-3), three cadinane dimers containing multiple contiguous quaternary carbons, were isolated from the rhizomes of Stahlianthus involucratus. Their structures were determined by a combination of NMR spectroscopy, chemical conversion, and X-ray diffraction analysis. Compounds 1 and 2 are rearranged homodimers of cadinane sesquiterpene fused with a unique fully substituted 1-oxaspiro[4.4]nonane core observed for the first time in natural products, and 3 is a novel 3',4'-seco-cadinane-dimer. Compounds 1 and 2 exhibited potent cytotoxic activities, and 3 showed notable anti-inflammatory effect.
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009 (P. R. China).
authors.forename: Qiang-Ming
authors.initials: QM
authors.lastname: Li
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009 (P. R. China).
authors.forename: Jian-Guang
authors.initials: JG
authors.lastname: Luo
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009 (P. R. China).
authors.forename: Yang-Mei
authors.initials: YM
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009 (P. R. China).
authors.forename: Zhong-Rui
authors.initials: ZR
authors.lastname: Li
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009 (P. R. China).
authors.forename: Xiao-Bing
authors.initials: XB
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009 (P. R. China).
authors.forename: Ming-Hua
authors.initials: MH
authors.lastname: Yang
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009 (P. R. China).
authors.forename: Jun
authors.initials: J
authors.lastname: Luo
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009 (P. R. China).
authors.forename: Hong-Bin
authors.initials: HB
authors.lastname: Sun
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009 (P. R. China).
authors.forename: Yi-Jun
authors.initials: YJ
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009 (P. R. China). cpu_lykong@126.com.
authors.forename: Ling-Yi
authors.initials: LY
authors.lastname: Kong
mesh_terms: D001688:Biological Products / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification; D013141:Spiro Compounds / Q000737:chemistry*; D014961:X-Ray Diffraction
chemical_list: D001688:Biological Products; D012717:Sesquiterpenes; D013141:Spiro Compounds; C000606505:involucratustone A; C000606506:involucratustone B; C000606507:involucratustone C
keywords: cadinane sesquiterpene dimer; natural products; quaternary carbons; spiro compounds; structure elucidation