小黄皮茎的木脂素类化学成分研究

目的研究小黄皮Clausena emarginata茎的木脂素类化学成分。方法采用硅藻土、硅胶等多种柱色谱、MPLC及制备型HPLC等方法对小黄皮茎的木脂素类化学成分进行分离纯化,根据理化性质结合现代波谱学方法鉴定化合物结构;并对其抑制脂多糖(LPS)诱导小胶质细胞BV2细胞一氧化氮(NO)的活性进行测试。结果从小黄皮茎的95%乙醇提取物的氯仿部位分离得到16个木脂素类化合物,分别鉴定为buddlenol C(1)、hedyotol D(2)、hedyotol C(3)、3-(2,4-二羟基-3-甲氧基苄基)-4-(4-羟基-3-甲氧基苄基)四氢呋喃(4)、tripterygiol(5)、busaliol(6)、2,3-bis[(4-hydroxy-3,5-dimethoxyphenyl)-methyl]-1,4-butanediol(7)、polystachyol(8)、丁香树脂酚(9)、nitidanin(10)、4-[3-hydroxymethyl-5-((E)-3-hydroxypropenyl)-7-methoxy-2,3-dihydrobenzofuran-2-yl]-2,6-dimethoxy-phenol(11)、erythro-guaiacylglycerol-β-O-4′-sinapyl ether(12)、erythro-guaiacylglycerol-8-O-4′-(coniferyl alcohol)ether(13)、赤式-1-(4-羟基-3-甲氧基苄基)-2-(4-甲酰基-2-甲氧基苯氧基)-丙烷-1,3-二醇(14)、rosalaevin B(15)和去氢双松柏醇(16)。结论化合物1～15为首次从该植物中分离得到,化合物8和16对LPS诱导BV2细胞产生NO具有一定的抑制活性。     

小黄皮茎的化学成分研究

目的研究芸香科植物小黄皮Clausena emarginata茎的化学成分。方法利用大孔树脂、硅胶柱色谱、反相柱色谱、凝胶柱色谱、中压液相等色谱方法对小黄皮茎的化学成分进行分离,再经制备液相进行纯化,通过紫外光谱、质谱和核磁共振谱等方法鉴定化合物结构。初步考察化合物11和12的神经保护活性。结果从小黄皮茎的95%乙醇提取物的石油醚和丙酮2个洗脱部位分离得到16个化合物,分别鉴定为1H-indole-3-carboxaldehyde(1)、E-N-benzoiltiramine(2)、去氢双松柏醇(3)、tortoside A(4)、浙贝素(5)、evofolin B(6)、2,3,5,4′-四羟基二苯乙烯-2-O-β-D-葡萄糖苷(7)、紫花松果菊苷A(8)、3-甲基咔唑(9)、murrayafoline A(10)、clausine Z(11)、indizoline(12)、clausenaline B(13)、mafaicheenamine A(14)、dictamnine(15)和和厚朴酚(16)。结论化合物1~8为首次从该属植物中分离得到,化合物1~16为首次从该植物中分离得到。化合物11和12对鱼藤酮损伤PC12细胞模型具有一定的神经保护作用。     

广西黄皮叶挥发油化学成分GC-MS分析研究

目的:对广西黄皮叶挥发油进行气相-质谱研究.方法:利用水蒸气蒸馏法提取广西黄皮叶挥发油,采用气相色谱-质谱联用法鉴定化学成分,归一化法测定各成分相对含量.结果:从广西黄皮叶挥发油中共分离出40多个组分,鉴定了其中32个化合物,占总量的90%以上,主要成分为石竹烯(25.31%)、石竹烯氧化物(14.86%)、β-红没药烯(8.95%)、斯巴醇(8.88%)、柏木-8(15)-烯-9-醇(7.54%)、α-法呢烯(6.51%)等,并鉴定出12种文献未见报道的组分.结论:广西黄皮叶挥发油中含倍半萜醇类、倍半萜烯类及其含氧衍生物等多种化学成分,本试验为广西黄皮叶的进一步开发利用提供了科学依据.     

小黄皮茎的化学成分及生物活性研究

目的 研究小黄皮Clausena emarginata茎的化学成分及其保肝活性.方法 采用硅藻土、硅胶等多种柱色谱、中压制备液相色谱(MPLC)及制备型HPLC等方法对小黄皮茎的化学成分进行分离纯化,根据化合物理化性质结合现代波谱学方法鉴定化合物结构;并测试其对DL-半乳糖胺诱导肝细胞损伤的保护活性及其对脂多糖(LPS...     

A new megastigmane glucoside and a new amide alkaloid from the leaves of Clausena lansium (Lour.) Skeels

A new megastigmane glucoside (6S,7E,9S)-6,9,10-trihydroxy-4,7-megastigmadien-3-one 9-O-β-d-glucopyranoside (1) and a new amide alkaloid (E)-N-(4-methoxyphenethyl)-2-methylbut-2-enamide (2), together with three known amide alkaloids (3–5), were isolated from the leaves of Clausena lansium (Lour.) Skeels. Their structures were elucidated by their physicochemical properties and analysis of their spectral data.     

Carbazole alkaloids as new cell cycle inhibitor and apoptosis inducers from Clausena dunniana Levl

Carbazole alkaloids, 3-methylcarbazole (1), murrayafoline A (2), girinimbine (3), mahanimbine (4) and bicyclomahanimbine (5), were isolated for the first time from Clausena dunniana Levl. by bioassay-guided separation procedure and were identified by spectroscopic methods. Compounds 1 - 5 showed growth inhibitory activity (1, IC₅₀ 25 μg/ml) on human fibrosarcoma HT-1080 cells and cell cycle M-phase inhibitory (2, MIC 0.78 μg/ml) and apoptosis inducing (2, MIC 1.56 μg/ml; 3, MIC 25 μg/ml; 4, MIC 20 μg/ml; 5, MIC 30 μg/ml) activities on mouse tsFT210 cells, respectively, and 2 - 5 provided the first examples of carbazole alkaloids as new cell cycle inhibitors and apoptosis inducers.     

Anti-inflammatory amide alkaloids from the stems of Clausena emarginata

Two new amide alkaloids, clauemaramide A (1) and clauemaramide B (2), and three known analogs were isolated from the stems of Clausena emarginata. Their structures were determined on the basis of spectroscopic analyses. The absolute configurations of 1 and 2 were confirmed by CD spectroscopy. Compound 3 showed moderate inhibitory effects on LPS-induced NO production (IC₅₀ value = 4.9 μM).     

黄皮酰胺的合成

根据推测的生源关系,以仿生路线合成了有保肝活性的植物成分黄皮酰胺。     

Carbazole alkaloids from the peels of Clausena lansium

A new carbazole alkaloid, claulansine K (1), together with six known carbazole alkaloids (2–7), was isolated from the peels of Clausena lansium (Lour.) Skeels. The new compound was elucidated using a combination of 1D and 2D NMR (HMQC, HMBC, COSY, and ROESY) techniques, and HR-EI-MS analyses. Compound 1 showed in vitro α-glucosidase inhibitory activity with the IC₅₀ value of 0.11 mM. Compound 2 exhibited moderate antibacterial activity against Staphylococcus aureus with the diameter of inhibition zone of 14.2 mm.     

Isolation of seselin from Clausena anisata (Rutaceae) leaves and its effects on the feeding and development of Lucilia cuprina larvae may explain its use in ethnoveterinary medicine

Ethnopharmacological relevance

The leaves of Clausena anisata are used traditionally to expel maggots from wounds of animals in Zimbabwe. We have previously proved in the laboratory that the plant certainly affects the behaviour and growth of blowfly larvae. The objective of this study was to isolate and identify the active compounds responsible for this activity.

Materials and methods

The acetone extract of Clausena anisata leaf powder was separated by solvent–solvent partition into five fractions. The n-hexane fraction was the most active in the larvicidal assay and therefore subjected to open column chromatography on silica gel.

Results

The isolated compound was identified by nuclear magnetic resonance (NMR) and mass spectroscopy (MS) as the pyranocoumarin, seselin, chemically known as 2′,2′-dimethylpyranocoumarin. It inhibited feed intake in the first and second instars of blowfly larvae at the minimum concentration tested of 1 ppm resulting in significant lower mass pupae (13.5±0.5 mg and 22.4±0.4 mg for the first and second instar larvae respectively) compared to the solvent control group (26.19±0.8 mg) (p<0.05).

Conclusions

This is the first report of the isolation of seselin from the leaves of Clausena anisata and the first report of the compound having an effect against blowfly larvae.