title: Protolimonoids and norlimonoids from the stem bark of Toona ciliata var. pubescens.
abstract: Six new tirucallane protolimonoids, toonapubesins A-F (1-6), one new rearranged tirucallane protolimonoid, toonapubesin G (7), and two new 21,22,23-trinorapotirucallane limonoids, toonapubesic acids A (8) and B (9), possessing an unprecedented carbon skeleton, along with five known tirucallane protolimonoids (10-14) and one known apotirucallane limonoid (15), were isolated from the stem bark of Toona ciliata var. pubescens. Their structures and relative configurations were determined by detailed spectroscopic analysis and by chemical methods. The proposed structures of 8 and 11 were confirmed by X-ray diffraction analysis of their respective derivatives (8a and 11a). The absolute configuration of 8 was determined by a novel solid-state TDDFT ECD approach on its derivative 8a while the absolute configuration of 10 was determined by the modified Mosher's method. In addition, the structures of dyvariabilin H (10c) proposed by Sticher et al. and cneorin-NP(36) (11b) by Mondon et al. were corrected as 10 and 11, respectively. Toonapubesin G (7) showed promising inhibitory activity against CDC25B with an IC(50) value of 2.1 μM, while compound 8a showed significant cell protecting activity against H(2)O(2)-induced SH-SY5Y cell damage with 11.5% increase in cell viability.
authors: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China.
authors: Jian-Rong
authors: JR
authors: Wang
authors: Hai-Li
authors: HL
authors: Liu
authors: Tibor
authors: T
authors: Kurtán
authors: Attila
authors: A
authors: Mándi
authors: Sándor
authors: S
authors: Antus
authors: Jia
authors: J
authors: Li
authors: Hai-Yan
authors: HY
authors: Zhang
authors: Yue-Wei
authors: YW
authors: Guo
mesh_terms: D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D018360:Crystallography, X-Ray; D004365:Drugs, Chinese Herbal / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D006861:Hydrogen Peroxide / Q000009:adverse effects; D036701:Limonins / Q000737:chemistry* / Q000145:classification / Q000302:isolation & purification / Q000494:pharmacology; D029582:Meliaceae / Q000737:chemistry*; D015394:Molecular Structure; D009447:Neuroblastoma / Q000188:drug therapy / Q000473:pathology; D019906:Nuclear Magnetic Resonance, Biomolecular; D018384:Oxidative Stress / Q000187:drug effects; D024301:Plant Bark / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D020687:cdc25 Phosphatases / Q000037:antagonists & inhibitors* / Q000378:metabolism
chemical_list: D004365:Drugs, Chinese Herbal; D036701:Limonins; D006861:Hydrogen Peroxide; D020687:cdc25 Phosphatases