| Objectives The current study was aimd to investigate the chemical constituents of Iliicium simonsii.C hemical constituents were isolated and purified by silica gel,Sephadex LH-20,Rp-C18 and pre HPLC methods.The structures from the friuts of I.simonsii were elucidated by spectroscopic methods including NMR,HRESIMS,and circular dichroism(CD).And the neuroprotective activity of the compounds from I.simonsii was also discussed.Methods 1 Fruits of I.simonsii(30 kg)were air-dried,ground,and extracted(2 h each)with Et OH/H2O(8 × 30 L,95:5,v/v)by refluxing(90–95 °C).The combined Et OH extracts were evaporated to near dryness under vacuum.The resulting residue was absorbed on kieselguhr and then successively extracted with petroleum ether,Et OAc,and Me OH.2 The Et OAc extract(300 g)after solvent evaporation was ongoing search for structurally unique and biologically interesting constituents.The compounds of Et OAc extract were isolated by silica gel,Sephadex LH-20,Rp-C18 and pre HPLC methods.The structures were elucidated by extensive spectroscopic analyses methods including NMR,HRESIMS,and circular dichroism(CD).3 The neuroprotective activity of compounds were evaluated by measuring the pheochromocytoma(PC12)cells viability using the MTT method,which were treated with glutamate and serum deprivation,injury modelResults 1 Twenty-eight compounds including nine sesquiterpenes 3?-OH-veranisati ns D(1),neoanisatin(2),veranisatin(3),veranisatins D(4),merrillanolide(5),8?-oxo-di hydrophaseic acid(6),ligandrumin B(7),1?-Hydroxy-3-deoxy-pseudoanisatin(8),liga ndrumin A(9),six lignans(-)-secoisolariciresinol(10),simulanol(11),(7R,8S)-dihy dro dehydrogenated dioxanol(12),(-)-Isolariciresinol 2a-O-?-D-glucopyranoside(13),??? C(14),Erythro-guaiacylglycerol-?-O-4?-coniferyl alcohol(15),two monoterpen es(1R,4R,5S)-5-endo-hydroxycamphor 5-O-?-D-glucopyranoside(27),Loliolide(28),and eleven other kinds of constituents 4-methoxybenzene-1,2-diol(16),5-(2-hydroxy ethyl)-2-methoxybenzaldehyd(17),1,4-benzenediol(18),4-(3-hydroxypropyl)-2-methox yphenol(19),4-methoxybenzaldehyde(20),4-hydroxybenzaldehyde(21),3-methoxy-4-h ydroxybenzaldehyde(22),2-(4-hydroxyphenyl)-?-D-Glucopyrano(23),4-hydroxyacetophenone(24),gallic acid(25),caesalpiniaphenol D(26)were isolated from the fruits o f Iliicium simonsii.2 Cell survival rates of compounds 1-5 exhibited were 34.3 ± 0.7 %,51.8 ± 0.4 %,31.6 ± 2.4 %,58.3 ± 1.5 %,63.4 ± 5.4 % lo-wer than t hat in serum deprivation-induced and differences were significant.Cell survival rat es of compounds 7 and 9 exhibited were 2.5 ± 3.1 %,73.3 ± 2.4 % higher than that in serum deprivation-induced and differences were significant.Cell survival r ates of compounds 14 exhibited was 67.4 ± 3.4 % higher than that in serum depr ivation-induced and differences were significant.3 Cell survival rates of compound s 1-5 exhibited were 44.2 ± 1.6 %,38.2 ± 4.3 %,57.2 ± 1.9 %,49.1 ± 1.7 %,47.4 ± 5.4 % lower than that in glutamate and differences were significant.Cell s urvival rates of compounds 14 exhibited was 67.4 ± 3.4 % higher than that in gl utamate and differences were significant.Conclusions 1 One new sesquiterpene compund,1,along with eight known sesquiterpenes(2-9),six known lignans(10-15),two known monoterpenes(27 and 28),and eleven other kinds of known constituents(16-26).Compounds(14?26?28)were isolated from Iliicium for the first time,Compounds(6?7?9?10?11?13?15?16?17?18?19?20?22?24?25?27)were isolated from Iliicium simonsii for the first time.2 New compound 1 possible exhibited toxic activities and(7,9 and 14)possible exhibited protective activities at 10-4 M. |
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