title: Spirotrichilins A and B: Two Rearranged Spirocyclic Limonoids from Trichilia connaroides.
abstract: Spirotrichilins A (1) and B (2), two novel limonoids with an unprecedented spiro[cyclopenta[b]furan-2,1'-cyclopentan] ring system in A/B/C rings, were isolated from the fruits of trichilia connaroides. Their planar structures and absolute configurations were established based on 1D-, 2D-NMR data, electronic circular dichroism (ECD) exciton chirality method and time-dependent density functional theory (TDDFT)/ECD calculation. A benzilic acid-like rearrangement in ring A was proposed as the key step in the plausible biogenetic pathway of 1 and 2.
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University , 24 Tong Jia Xiang, Nanjing 210009, People's Republic of China.
authors.forename: Fa-Liang
authors.initials: FL
authors.lastname: An
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University , 24 Tong Jia Xiang, Nanjing 210009, People's Republic of 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, People's Republic of China.
authors.forename: Rui-Jun
authors.initials: RJ
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, People's Republic of 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, People's Republic of 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, People's Republic of 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, People's Republic of China.
authors.forename: Lei
authors.initials: L
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, People's Republic of China.
authors.forename: He-Quan
authors.initials: HQ
authors.lastname: Yao
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University , 24 Tong Jia Xiang, Nanjing 210009, People's Republic of 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, People's Republic of 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, People's Republic of China.
authors.forename: Ling-Yi
authors.initials: LY
authors.lastname: Kong
mesh_terms: D001669:Biochemical Phenomena; D002942:Circular Dichroism; D005638:Fruit; D036701:Limonins / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D029582:Meliaceae / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D036701:Limonins; D013141:Spiro Compounds; C000611117:spirotrichilin A; C000611145:spirotrichilin B