传统中药白背叶和鹅绒委陵菜的化学成分及生物活性研究
|
摘要
本论文选取了两种传统中药白背叶[Mallotus apelta(Lour.)Muell.-Arg.]和鹅绒委陵菜(Potentilla anserine L.),对其进行了系统的化学成分及生物活性研究。
白背叶[Mallotus apelta(Lour.)Muell.-Arg.]为大戟科(Euphorbiaceae)野桐属(Mallotus)植物,分布于我国广西、海南等南方地区,是我国的传统中药,用于治疗慢性肝炎、口疮、外伤出血等。我们在对白背叶进行保肝活性筛选时,发现乙醇提取物及各萃取部位均具有一定的保肝活性,其中以乙醇提取物和正丁醇部位活性为最强;抗肿瘤活性筛选发现石油醚部位具有一定的细胞毒活性。
为了阐明白背叶的药效物质基础,我们对白背叶根进行了系统的化学成分研究,运用多种分离方法和波谱学技术共分离鉴定了24个化合物,包括6个香豆素苯丙素复合体类化合物、2个倍半萜类化合物、1个香豆素类化合物、1个木脂素类化合物、1个黄酮类化合物、2个酚苷类化合物、2个神经酰胺类化合物、6个三萜类化合物、3个甾醇类化合物。其中4个化合物为新化合物(M1～M3为香豆素苯丙素复合体类化合物、M7为倍半萜类化合物),M5、M8、M10-M19、M21等13个化合物为首次从野桐属中分离得到。这24个化合物是:malloapelinA(M1)、malloapelin B(M2)、malloapelin C(M3)、5'-demethylaquillochin(M4)、cleomiscosins A(M5)、cleomiscosins B(M6)、malloapelin D(M7)、dearabinosylpneumonathoside(M8)、东莨菪内酯(M9)、槲皮素(M10)、schizandriside(M11)、3-甲氧基-4-O-β-D-葡萄糖基苯甲酸(M12)、berchemolide(M13)、1-O-β-D-glucopy-ranosyl-(2S,3R,4E,8Z)-2-[(2-hydroxyhexadecanoyl)amido]-4,8-octadecadiene-1,3-diol(M14)、1-O-β-D-glucopyranosyl-(2S,3R,4E,8E)-2-[(2-hydroxyoctadecanoyl)amido]-4,8-octadecadiene-1,3-diol(M15)、β-香树脂醇乙酸酯(M16)、高根二醇(M17)、lup-20(29)-en-3β,30-diol(M18)、2α-hydroxyaleuritolic acid 3-p-hydroxybenzoate(M19)、α-香树脂醇乙酸酯(M20)、油桐酸(M21)、β-谷甾醇(M22)、胡萝卜苷(M23)、豆甾醇(M24)。对香豆素苯丙素复合体类化合物的生源途径进行了初步研究,假定了一条6,7,8-三羟基香豆素与3-甲氧基咖啡醇的自由基氧化偶连的生源途程,解释了得到的香豆素苯丙素复合体类化合物旋光值为零的问题。
对分离得到的3个香豆素苯丙素复合体类新化合物进行了多种生物活性筛选:保肝活性筛选结果表明,化合物M1-M3对半乳糖胺引起的大鼠肝脏内皮细胞损伤都具有一定的抑制作用,给药浓度为10~(-4)M时抑制率分别为3.5%、11.3%、26.2%;在抗肿瘤活性筛选时,发现化合物M2对人胃癌细胞(BGC-823)具有细胞毒作用(IC_(50)为0.74μM),化合物M3对人肺腺癌细胞(A549)和人卵巢癌细胞(A2780)均具有细胞毒作用(IC_(50)分别为0.65和0.43μM);抗HIV活性筛选未发现化合物M1～M3具有抗病毒活性。
鹅绒委陵菜(Potentilla anserine L.)为蔷薇科(Rosaceae)委陵菜属(Potentilla)植物,分布于我国北方各省及西南的四川、云南、西藏等地,是我国的传统中药,用于治疗吐血、疟疾痈疮、脾虚腹泻等症,民间还用于治疗糖尿病。在抗糖尿病活性筛选时,发现鹅绒委陵菜乙醇提取物及各萃取部位均具有一定的蛋白酪氨酸磷酸酶1B(PTP1B)抑制活性和α-葡萄糖苷酶抑制活性。
利用各种现代分离方法和波谱学技术,对鹅绒委陵菜进行了系统的化学成分研究,分离鉴定了53个化合物,包括23个黄酮类化合物、3个单萜类化合物、1个倍半萜类化合物、1个三萜类化合物、17个多酚类化合物、3个绿原酸衍生物、2个甾醇类化合物和3个其它类化合物。其中2个化合物(P1、P2)为新化合物,化合物P1为少见的由μ-truxinic acid基团相连接的双黄酮类化合物;化合物P2为单萜类化合物。P4～P7、P9～P13、P15～P16、P18～P19、P21～P22、P24～47、P51～P53等42个化合物为首次从委陵菜属中分离得到。这53化合物是:potentilin(P1)、2,6-dimethy1-2,3-dihydro-4-oxo-4H-pyran-2-acetic acid(P2)、kaempferol-3-O-β-D-(6-O-trans-p-coumaroyl)glucopyranoside(P3)、kaempferol-3-O-β-D-(2-O-trans-p-coumaroyl)glucopyranoside(P4)、apigenin-6-C-(2″-O-α-L-rhamnopyranosyl-β-D-glucopyranoside)(P5)、vicenin-Ⅱ(P6)、apigenin-6-C-β-D-glucopyranosyl-8-C-β-D-xylopyranoside(P7)、schaftoside(P8)、isovitexin(P9)、芦丁(P10)、quercetin-3,7-di-O-β-D-glucopyranoside(P11)、isoscutellarein-8-O-β-D-glucopyranoside(P12)、luteolin-3′-O-β-D-glucopyranoside(P13)、luteolin-7-O-β-D-glucuronide(P14)、luteolin-7-O-β-D-glucopyranoside(P15)、quercetin-7-O-β-D-glucopyranoside(P16)、黄芪苷(P17)、reynoutrin(P18)、quercetin-3-O-β-D-glucuronide(P19)、isoquercitrin(P20)、quercetin-3-O-α-L-rhamnopyranoside(P21)、木樨草素(P22)、槲皮素(P23)、5,7-二羟基色原酮(P24)、loliolide(P25)、isololiolide(P26)、dehydrocomifoliol(P27)、ellagic acid 4-O-β-D-glucopyranoside(P28)、ellagic acid 4-O-β-D-xylopyranoside(P29)、3'-O-methylellagic acid 4-O-β-D-glucopyranoside(P30)、短叶苏木酚酸(P31)、短叶苏木酚(P32)、vanillic acid 4-O-β-D-glucopyrano- side(P33)、picein(P34)、4-glucosyloxybenzoic acid(P35)、3,4-二羟基苯甲酸(P36)、咖啡酸(P37)、对羟基肉桂酸(P38)、对羟基苯甲酸(P39)、3,4-二羟基苯甲酸乙酯(P49)、丁香酸(P41)、β-hydroxypropiovanillone(P42)、对羟基苯甲醛(P43)、对羟基苯乙酮(P44)、绿原酸(P45)、4-O-caffeoylquinic acid(crytochlorogenic acid,P46)、5-O-caffeoylquinicacid(neochlorogenic acid,P47)、熊果酸(P48)、β-谷甾醇(P49)、胡萝卜苷(P50)、5-羟甲基糠醛(P51)、反式丁烯二酸(P52)、琥珀酸单乙酯(P53)。运用HPLC-DAD和LC-MS分析技术,获得了鹅绒委陵菜甲醇提取物的紫外(UV)和质谱(MS)图,结合从鹅绒委陵菜乙醇提取物中分离出的53个化合物,对相关峰进行了指认,为规范鹅绒委陵菜的质量控制标准,避免该属植物由于外观形态的类似而产生混用的现象提供科学依据。
药理活性筛选结果表明:(1)鹅绒委陵菜中化合物P3、P4、P10、P11、P29和P48均具有一定的蛋白酪氨酸磷酸酶1 B(PTP1B)抑制活性,在给药浓度为10μM时,抑制率分别达到51.0、51.7、30.4、45.9、64.1和34.4%。(2)抗炎活性筛选结果显示鹅绒委陵菜乙醇提取物石油醚部位、乙酸乙酯部位和水部位在100mg/kg剂量皮下给药时可明显抑制巴豆油引起的小鼠耳肿胀,抑制率分别为21.8、44.9和66.4%。(3)抗肿瘤活性筛选结果显示乙酸乙酯部位对人结肠癌细胞(HCT-8)、人肝癌细胞(Bel-7402)、人胃癌细胞(BGC-823)、人肺腺癌细胞(A549)和人卵巢癌细胞(A2780)都具有细胞毒作用,IC_(50)值分别为2.34、26.93、7.54、13.06和25.88μg/mL;石油醚部位对人肝癌细胞和人胃癌细胞具有一定的选择性细胞毒作用,其IC_(50)值分别为19.89和17.78μg/mL;该植物中含量较高的化合物P48(熊果酸)对人肺腺癌细胞和人卵巢癌细胞也具有一定的选择性细胞毒作用,IC_(50)值分别为0.76×10~(-6)和0.73×10~(-6)M。
The chemical constituents and bioactivities of two traditional Chinese medicines, Mallotus apelta(Lour.)Muell.-Arg,and Potentilla anserine L.,were studied in this paper.
Mallotus apelta(Lour.)Muell.-Arg.(Euphorbiaceae) is widely distributed in the south of China.Its roots and leaves are used in traditional Chinese medicine for the treatment of chronic hepatitis,ulcer,eczema and hemostasis.In our ongoing searching for hepatoprotective compounds from natural sources using rat hepatic epithetlial stem-like cells(WB-F344) with D-galactosamine as a screening system,the 70% ethanolic extract of the roots of M.apelta showed significant hepatoprotective activity. The petroleum ether soluble fraction of 70%ethanolic extract also showed moderate cytotoxic activity.
In order to elucidate the bioactive components of M.apelta,we carried out the chemical investigation of the roots of M.apelta.By using various separation technologies,24 compounds were isolated.On the basis of spectroscopic and chemical methods,their structures were established as follows:malloapelin A(M1),malloapelin B(M2),malloapelin C(M3),5'-demethylaquillochin(M4),cleomiscosins A(M5), cleomiscosins B(M6),malloapelin D(M7),dearabinosyl pneumonathoside(M8), scopoletin(M9),quercetin(M10),schizandriside(M11),vanillic acid glucoside(M12), berchemolide(M13),1-O-β-D-glucopyranosyl-(2S,3R,4E,SZ)-2-[(2-hydroxyhexadecanoyl)amido]-4, 8-octadecadiene-1,3-diol(M14),1-O-β-D-glucopyranosyl-(2S,3R,4E, 8E)-2-[(2-hydroxyoctadcaenoyl)amido]-4,8-octadecadiene-1,3-diol(M15),β-amyrin acetate(M16),erythrodiol(M17),1up-20(29)-en-3β,30-diol(M18),2α-hydroxyaleuritolic acid 3-p-hydroxybenzoate(M19),α-amyrin acetate(M20),aleuritolic acid (M21),β-sitosterol(M22),daucosterol(M23),stigmasterol(M24).Among them,there were three new coumarinolignoids(malloapelin A～C,M1～M3) and a new sesquiterpenoid(malloapelin D,M7).Thirteen known compounds(M5,M8,M10～M19,M21) were isolated for the first time from this species.
We proposed a plausible biosynthetic pathway for M1.It arise by oxidative coupling processes between 6,7,8-trihydroxy-coumarin and 3-methoxy-caffeyl alcohol.
The hepatoprotective activities of three new compounds M1-M3 were assessed by measuring their effects on the cell survival rate.All the coumarinolignoids showed inhibitory activity against D-galactosamine-induced toxicity in WB-F344 cell at 10~(-4)M in vitro,without any obvious cytotoxic effects with inhibitory rates of 3.5,11.3 and 26.2%,respectively.The antitumor test in vitro against human tumor cell lines with MTT method indicated that M2 showed cytotoxic activity against BGC-823 with an IC_(50) value of 0.74μM,and M3 showed cytotoxic activity against A549 and A2780 with IC_(50) value of 0.65 and 0.43μM,respectively.However,in the anti-HIV test in vitro,no compounds showed obvious activities against HIV.
Potentilla anserine L.(Rosaceae) has long been used as traditional Chinese medicinal herbs for anti-rheumatism,detoxification,and curing diabetes,which distributed in the north and southwest of China.In our previous biological investigations,the ethanol extracts,petroleum ether and EtOAc soluble fractions showed PTP1B andα-glucosidase inhibitory activities.
By means of chromatography methods and spectral technologies,we carried out the chemical investigation of P.anserine.53 Compounds were isolated.On the basis of spectroscopic and chemical methods,their structures were established as follows: potentilin(P1),2,6-dimethyl-2,3-dihydro-4-oxo-4H-pyran-2-acetic acid(P2),kaempferol-3-O-β-D-(6-O-trans-p-coumaroyl)glucop yranoside(P3), kaempferol-3-O-β-D-(2-O-trans-p-coumaroyl)glucopyranoside(P4), apigenin-6-C-(2"-O-α-L-rhamnopyranosyl-β-D-glucopyranoside)(P5), vicenin-Ⅱ(P6),apigenin-6-C-β-D-glucopyranosyl-8-C-β-D-xylopyranoside(P7), schaftoside(P8),isovitexin(P9),rutin(P10),quercetin-3,7-di-O-β-D-glucopyranoside(P11), isoscutellarein-8-O-β-D-glucopyranoside(P12),luteolin-3'-O-β-D-glucopyranoside(P13), luteolin-7-O-β-D-glucuronide(P14),luteolin-7-O-β-D-glucopyranoside(P15), quercetin-7-O-β-D-glucopyranoside(P16),astragalin(P17), reynoutrin(P18),quercetin-3-O-β-D-glucuronide(P19),isoquercitrin(P20),quercetin-3-O-α-L-rhamnopyranoside(P21), luteolin(P22),quercetin(P23),5,7-dihydroxychromone(P24), loliolide(P25),isololiolide(P26),dehydrocomifoliol(P27),ellagic acid 4-O-β-D-glucopyranoside(P28),ellagic acid 4-O-β-D-xylopyranoside(P29),3'-O- methylellagic acid 4-O-β-D-glucopyranoside(P30),brevifolincarboxylic acid(P31), brevifolin(P32),vanillic acid 4-O-β-D-glucopyranoside(P33),picein(P34),4-glucosyloxybenzoic acid(P35),3,4-dihydroxybenzoic acid(P36),caffeic acid(P37),E-4-hydroxycinnamic acid(P38),4-hydroxybenzoic acid(P39),ethyl-3,4-dihydroxybenzoate (P40),4-hydroxy-3,5-dimethoxy benzoic acid(P41),β-hydroxypropiovanillone(P42), 4-hydroxybenzaldehyde(P43),4-hydroxyacetophenone(P44),chlorogenic acid(P45), crytochlorogenic acid(P46),neochlorogenic acid(P47),ursolic acid(P48),β-sitosterol (P49),daucosterol(P50),5-hydroxymethyl furaldehyde(P51),E-2-butenedioic acid (P52),ethyl hydrogen succinate(P53).Among them,P1 was a rare new diflavonol ester ofμ-truxinic acid and P2 was a new normonoterpenoid.42 Compounds(P4～P7, P9～P13,P15～P16,P18～P19,P21～P22,P24～47,P51～P53) were isolated for the first time from this species.By using HPLC-DAD and LC-MS,we got the fingerprints of the methanol extracts of P.anserine.Some peaks of fingerprints were identified by comparing with the 53 compounds isolated from P.anserine.
The PTP 1B inhibitory activities of eighteen compounds isolated from P.anserine. were evaluated.At a concentration of 10μM,P3,P4,P10,P11,P29 and P48 showed moderate PTP1B inhibitory activities with inhibitory rates of 51.0,51.7,30.4,45.9, 64.1 and 34.4%,respectively.The petroleum ether,EtOAc and aqueous soluble fractions showed anti-flammatory activities against croton oil-induced rat ear swell at a dose of 100mg/kg,with inhibitory rates of 21.8,44.9 and 66.4%,respectively.In the anticancer activities assay,the EtOAc soluble fractions showed nonselective cytotoxicty against HCT-8,Bel-7402,BGC-823,A549 and A2780,with IC_(50) values of 2.34、26.93、7.54、13.06 and 25.88μg/mL,respectively.The petroleum ether soluble fractions showed selective cytotoxicty against Bel-7402 and BGC-823 with IC_(50) values of 19.89 and 17.78μg/mL,respectively.Compound P48 also showed selective cytotoxicty against A549 and A2780 with IC_(50) values of 0.76×10~(-6) and 0.73×10~(-6) M, respectively.
白背叶[Mallotus apelta(Lour.)Muell.-Arg.]为大戟科(Euphorbiaceae)野桐属(Mallotus)植物,分布于我国广西、海南等南方地区,是我国的传统中药,用于治疗慢性肝炎、口疮、外伤出血等。我们在对白背叶进行保肝活性筛选时,发现乙醇提取物及各萃取部位均具有一定的保肝活性,其中以乙醇提取物和正丁醇部位活性为最强;抗肿瘤活性筛选发现石油醚部位具有一定的细胞毒活性。
为了阐明白背叶的药效物质基础,我们对白背叶根进行了系统的化学成分研究,运用多种分离方法和波谱学技术共分离鉴定了24个化合物,包括6个香豆素苯丙素复合体类化合物、2个倍半萜类化合物、1个香豆素类化合物、1个木脂素类化合物、1个黄酮类化合物、2个酚苷类化合物、2个神经酰胺类化合物、6个三萜类化合物、3个甾醇类化合物。其中4个化合物为新化合物(M1～M3为香豆素苯丙素复合体类化合物、M7为倍半萜类化合物),M5、M8、M10-M19、M21等13个化合物为首次从野桐属中分离得到。这24个化合物是:malloapelinA(M1)、malloapelin B(M2)、malloapelin C(M3)、5'-demethylaquillochin(M4)、cleomiscosins A(M5)、cleomiscosins B(M6)、malloapelin D(M7)、dearabinosylpneumonathoside(M8)、东莨菪内酯(M9)、槲皮素(M10)、schizandriside(M11)、3-甲氧基-4-O-β-D-葡萄糖基苯甲酸(M12)、berchemolide(M13)、1-O-β-D-glucopy-ranosyl-(2S,3R,4E,8Z)-2-[(2-hydroxyhexadecanoyl)amido]-4,8-octadecadiene-1,3-diol(M14)、1-O-β-D-glucopyranosyl-(2S,3R,4E,8E)-2-[(2-hydroxyoctadecanoyl)amido]-4,8-octadecadiene-1,3-diol(M15)、β-香树脂醇乙酸酯(M16)、高根二醇(M17)、lup-20(29)-en-3β,30-diol(M18)、2α-hydroxyaleuritolic acid 3-p-hydroxybenzoate(M19)、α-香树脂醇乙酸酯(M20)、油桐酸(M21)、β-谷甾醇(M22)、胡萝卜苷(M23)、豆甾醇(M24)。对香豆素苯丙素复合体类化合物的生源途径进行了初步研究,假定了一条6,7,8-三羟基香豆素与3-甲氧基咖啡醇的自由基氧化偶连的生源途程,解释了得到的香豆素苯丙素复合体类化合物旋光值为零的问题。
对分离得到的3个香豆素苯丙素复合体类新化合物进行了多种生物活性筛选:保肝活性筛选结果表明,化合物M1-M3对半乳糖胺引起的大鼠肝脏内皮细胞损伤都具有一定的抑制作用,给药浓度为10~(-4)M时抑制率分别为3.5%、11.3%、26.2%;在抗肿瘤活性筛选时,发现化合物M2对人胃癌细胞(BGC-823)具有细胞毒作用(IC_(50)为0.74μM),化合物M3对人肺腺癌细胞(A549)和人卵巢癌细胞(A2780)均具有细胞毒作用(IC_(50)分别为0.65和0.43μM);抗HIV活性筛选未发现化合物M1～M3具有抗病毒活性。
鹅绒委陵菜(Potentilla anserine L.)为蔷薇科(Rosaceae)委陵菜属(Potentilla)植物,分布于我国北方各省及西南的四川、云南、西藏等地,是我国的传统中药,用于治疗吐血、疟疾痈疮、脾虚腹泻等症,民间还用于治疗糖尿病。在抗糖尿病活性筛选时,发现鹅绒委陵菜乙醇提取物及各萃取部位均具有一定的蛋白酪氨酸磷酸酶1B(PTP1B)抑制活性和α-葡萄糖苷酶抑制活性。
利用各种现代分离方法和波谱学技术,对鹅绒委陵菜进行了系统的化学成分研究,分离鉴定了53个化合物,包括23个黄酮类化合物、3个单萜类化合物、1个倍半萜类化合物、1个三萜类化合物、17个多酚类化合物、3个绿原酸衍生物、2个甾醇类化合物和3个其它类化合物。其中2个化合物(P1、P2)为新化合物,化合物P1为少见的由μ-truxinic acid基团相连接的双黄酮类化合物;化合物P2为单萜类化合物。P4～P7、P9～P13、P15～P16、P18～P19、P21～P22、P24～47、P51～P53等42个化合物为首次从委陵菜属中分离得到。这53化合物是:potentilin(P1)、2,6-dimethy1-2,3-dihydro-4-oxo-4H-pyran-2-acetic acid(P2)、kaempferol-3-O-β-D-(6-O-trans-p-coumaroyl)glucopyranoside(P3)、kaempferol-3-O-β-D-(2-O-trans-p-coumaroyl)glucopyranoside(P4)、apigenin-6-C-(2″-O-α-L-rhamnopyranosyl-β-D-glucopyranoside)(P5)、vicenin-Ⅱ(P6)、apigenin-6-C-β-D-glucopyranosyl-8-C-β-D-xylopyranoside(P7)、schaftoside(P8)、isovitexin(P9)、芦丁(P10)、quercetin-3,7-di-O-β-D-glucopyranoside(P11)、isoscutellarein-8-O-β-D-glucopyranoside(P12)、luteolin-3′-O-β-D-glucopyranoside(P13)、luteolin-7-O-β-D-glucuronide(P14)、luteolin-7-O-β-D-glucopyranoside(P15)、quercetin-7-O-β-D-glucopyranoside(P16)、黄芪苷(P17)、reynoutrin(P18)、quercetin-3-O-β-D-glucuronide(P19)、isoquercitrin(P20)、quercetin-3-O-α-L-rhamnopyranoside(P21)、木樨草素(P22)、槲皮素(P23)、5,7-二羟基色原酮(P24)、loliolide(P25)、isololiolide(P26)、dehydrocomifoliol(P27)、ellagic acid 4-O-β-D-glucopyranoside(P28)、ellagic acid 4-O-β-D-xylopyranoside(P29)、3'-O-methylellagic acid 4-O-β-D-glucopyranoside(P30)、短叶苏木酚酸(P31)、短叶苏木酚(P32)、vanillic acid 4-O-β-D-glucopyrano- side(P33)、picein(P34)、4-glucosyloxybenzoic acid(P35)、3,4-二羟基苯甲酸(P36)、咖啡酸(P37)、对羟基肉桂酸(P38)、对羟基苯甲酸(P39)、3,4-二羟基苯甲酸乙酯(P49)、丁香酸(P41)、β-hydroxypropiovanillone(P42)、对羟基苯甲醛(P43)、对羟基苯乙酮(P44)、绿原酸(P45)、4-O-caffeoylquinic acid(crytochlorogenic acid,P46)、5-O-caffeoylquinicacid(neochlorogenic acid,P47)、熊果酸(P48)、β-谷甾醇(P49)、胡萝卜苷(P50)、5-羟甲基糠醛(P51)、反式丁烯二酸(P52)、琥珀酸单乙酯(P53)。运用HPLC-DAD和LC-MS分析技术,获得了鹅绒委陵菜甲醇提取物的紫外(UV)和质谱(MS)图,结合从鹅绒委陵菜乙醇提取物中分离出的53个化合物,对相关峰进行了指认,为规范鹅绒委陵菜的质量控制标准,避免该属植物由于外观形态的类似而产生混用的现象提供科学依据。
药理活性筛选结果表明:(1)鹅绒委陵菜中化合物P3、P4、P10、P11、P29和P48均具有一定的蛋白酪氨酸磷酸酶1 B(PTP1B)抑制活性,在给药浓度为10μM时,抑制率分别达到51.0、51.7、30.4、45.9、64.1和34.4%。(2)抗炎活性筛选结果显示鹅绒委陵菜乙醇提取物石油醚部位、乙酸乙酯部位和水部位在100mg/kg剂量皮下给药时可明显抑制巴豆油引起的小鼠耳肿胀,抑制率分别为21.8、44.9和66.4%。(3)抗肿瘤活性筛选结果显示乙酸乙酯部位对人结肠癌细胞(HCT-8)、人肝癌细胞(Bel-7402)、人胃癌细胞(BGC-823)、人肺腺癌细胞(A549)和人卵巢癌细胞(A2780)都具有细胞毒作用,IC_(50)值分别为2.34、26.93、7.54、13.06和25.88μg/mL;石油醚部位对人肝癌细胞和人胃癌细胞具有一定的选择性细胞毒作用,其IC_(50)值分别为19.89和17.78μg/mL;该植物中含量较高的化合物P48(熊果酸)对人肺腺癌细胞和人卵巢癌细胞也具有一定的选择性细胞毒作用,IC_(50)值分别为0.76×10~(-6)和0.73×10~(-6)M。
The chemical constituents and bioactivities of two traditional Chinese medicines, Mallotus apelta(Lour.)Muell.-Arg,and Potentilla anserine L.,were studied in this paper.
Mallotus apelta(Lour.)Muell.-Arg.(Euphorbiaceae) is widely distributed in the south of China.Its roots and leaves are used in traditional Chinese medicine for the treatment of chronic hepatitis,ulcer,eczema and hemostasis.In our ongoing searching for hepatoprotective compounds from natural sources using rat hepatic epithetlial stem-like cells(WB-F344) with D-galactosamine as a screening system,the 70% ethanolic extract of the roots of M.apelta showed significant hepatoprotective activity. The petroleum ether soluble fraction of 70%ethanolic extract also showed moderate cytotoxic activity.
In order to elucidate the bioactive components of M.apelta,we carried out the chemical investigation of the roots of M.apelta.By using various separation technologies,24 compounds were isolated.On the basis of spectroscopic and chemical methods,their structures were established as follows:malloapelin A(M1),malloapelin B(M2),malloapelin C(M3),5'-demethylaquillochin(M4),cleomiscosins A(M5), cleomiscosins B(M6),malloapelin D(M7),dearabinosyl pneumonathoside(M8), scopoletin(M9),quercetin(M10),schizandriside(M11),vanillic acid glucoside(M12), berchemolide(M13),1-O-β-D-glucopyranosyl-(2S,3R,4E,SZ)-2-[(2-hydroxyhexadecanoyl)amido]-4, 8-octadecadiene-1,3-diol(M14),1-O-β-D-glucopyranosyl-(2S,3R,4E, 8E)-2-[(2-hydroxyoctadcaenoyl)amido]-4,8-octadecadiene-1,3-diol(M15),β-amyrin acetate(M16),erythrodiol(M17),1up-20(29)-en-3β,30-diol(M18),2α-hydroxyaleuritolic acid 3-p-hydroxybenzoate(M19),α-amyrin acetate(M20),aleuritolic acid (M21),β-sitosterol(M22),daucosterol(M23),stigmasterol(M24).Among them,there were three new coumarinolignoids(malloapelin A～C,M1～M3) and a new sesquiterpenoid(malloapelin D,M7).Thirteen known compounds(M5,M8,M10～M19,M21) were isolated for the first time from this species.
We proposed a plausible biosynthetic pathway for M1.It arise by oxidative coupling processes between 6,7,8-trihydroxy-coumarin and 3-methoxy-caffeyl alcohol.
The hepatoprotective activities of three new compounds M1-M3 were assessed by measuring their effects on the cell survival rate.All the coumarinolignoids showed inhibitory activity against D-galactosamine-induced toxicity in WB-F344 cell at 10~(-4)M in vitro,without any obvious cytotoxic effects with inhibitory rates of 3.5,11.3 and 26.2%,respectively.The antitumor test in vitro against human tumor cell lines with MTT method indicated that M2 showed cytotoxic activity against BGC-823 with an IC_(50) value of 0.74μM,and M3 showed cytotoxic activity against A549 and A2780 with IC_(50) value of 0.65 and 0.43μM,respectively.However,in the anti-HIV test in vitro,no compounds showed obvious activities against HIV.
Potentilla anserine L.(Rosaceae) has long been used as traditional Chinese medicinal herbs for anti-rheumatism,detoxification,and curing diabetes,which distributed in the north and southwest of China.In our previous biological investigations,the ethanol extracts,petroleum ether and EtOAc soluble fractions showed PTP1B andα-glucosidase inhibitory activities.
By means of chromatography methods and spectral technologies,we carried out the chemical investigation of P.anserine.53 Compounds were isolated.On the basis of spectroscopic and chemical methods,their structures were established as follows: potentilin(P1),2,6-dimethyl-2,3-dihydro-4-oxo-4H-pyran-2-acetic acid(P2),kaempferol-3-O-β-D-(6-O-trans-p-coumaroyl)glucop yranoside(P3), kaempferol-3-O-β-D-(2-O-trans-p-coumaroyl)glucopyranoside(P4), apigenin-6-C-(2"-O-α-L-rhamnopyranosyl-β-D-glucopyranoside)(P5), vicenin-Ⅱ(P6),apigenin-6-C-β-D-glucopyranosyl-8-C-β-D-xylopyranoside(P7), schaftoside(P8),isovitexin(P9),rutin(P10),quercetin-3,7-di-O-β-D-glucopyranoside(P11), isoscutellarein-8-O-β-D-glucopyranoside(P12),luteolin-3'-O-β-D-glucopyranoside(P13), luteolin-7-O-β-D-glucuronide(P14),luteolin-7-O-β-D-glucopyranoside(P15), quercetin-7-O-β-D-glucopyranoside(P16),astragalin(P17), reynoutrin(P18),quercetin-3-O-β-D-glucuronide(P19),isoquercitrin(P20),quercetin-3-O-α-L-rhamnopyranoside(P21), luteolin(P22),quercetin(P23),5,7-dihydroxychromone(P24), loliolide(P25),isololiolide(P26),dehydrocomifoliol(P27),ellagic acid 4-O-β-D-glucopyranoside(P28),ellagic acid 4-O-β-D-xylopyranoside(P29),3'-O- methylellagic acid 4-O-β-D-glucopyranoside(P30),brevifolincarboxylic acid(P31), brevifolin(P32),vanillic acid 4-O-β-D-glucopyranoside(P33),picein(P34),4-glucosyloxybenzoic acid(P35),3,4-dihydroxybenzoic acid(P36),caffeic acid(P37),E-4-hydroxycinnamic acid(P38),4-hydroxybenzoic acid(P39),ethyl-3,4-dihydroxybenzoate (P40),4-hydroxy-3,5-dimethoxy benzoic acid(P41),β-hydroxypropiovanillone(P42), 4-hydroxybenzaldehyde(P43),4-hydroxyacetophenone(P44),chlorogenic acid(P45), crytochlorogenic acid(P46),neochlorogenic acid(P47),ursolic acid(P48),β-sitosterol (P49),daucosterol(P50),5-hydroxymethyl furaldehyde(P51),E-2-butenedioic acid (P52),ethyl hydrogen succinate(P53).Among them,P1 was a rare new diflavonol ester ofμ-truxinic acid and P2 was a new normonoterpenoid.42 Compounds(P4～P7, P9～P13,P15～P16,P18～P19,P21～P22,P24～47,P51～P53) were isolated for the first time from this species.By using HPLC-DAD and LC-MS,we got the fingerprints of the methanol extracts of P.anserine.Some peaks of fingerprints were identified by comparing with the 53 compounds isolated from P.anserine.
The PTP 1B inhibitory activities of eighteen compounds isolated from P.anserine. were evaluated.At a concentration of 10μM,P3,P4,P10,P11,P29 and P48 showed moderate PTP1B inhibitory activities with inhibitory rates of 51.0,51.7,30.4,45.9, 64.1 and 34.4%,respectively.The petroleum ether,EtOAc and aqueous soluble fractions showed anti-flammatory activities against croton oil-induced rat ear swell at a dose of 100mg/kg,with inhibitory rates of 21.8,44.9 and 66.4%,respectively.In the anticancer activities assay,the EtOAc soluble fractions showed nonselective cytotoxicty against HCT-8,Bel-7402,BGC-823,A549 and A2780,with IC_(50) values of 2.34、26.93、7.54、13.06 and 25.88μg/mL,respectively.The petroleum ether soluble fractions showed selective cytotoxicty against Bel-7402 and BGC-823 with IC_(50) values of 19.89 and 17.78μg/mL,respectively.Compound P48 also showed selective cytotoxicty against A549 and A2780 with IC_(50) values of 0.76×10~(-6) and 0.73×10~(-6) M, respectively.
引文
[1]侯宽昭,中国种子植物科属词典.第2版[M].北京:科学出版社,1982:292.
[2]全国中草药汇编编写组,全国中草药汇编M].北京:人民卫生出版社,1975:297.
[3]浙江药用植物志编写组,浙江药用植物志[M].杭州:浙江科学技术出版社,1980:715.
[4]中国科学院昆明植物研究所,云南种子植物名录[M].昆明:云南人民出版社,1984:447.
[5]刘国民;李娟玲;王小精;何秋香,海南鸱鸪茶的民族植物学研究[J].海南师范大学学报(自然科学版) 2007,20,(2),167-171.
[6]Okabe,H.;Inoue,K.;Yamauchi,T.,Studies on the constituents of Mallotus japonicus Muell.Arg.L.cardiac glycosides from the seeds[J].Chem.Pharm.Bull.1976,24,(1),108-113.
[7]Shigematsu,N.;Kouno,I.;Kawano,N.,Phloroglucinol derivatives from fruits of Mallotus japonicus[J].Phytochemistty 1983,22,(1),323-325.
[8]Arisawa,M.;Fujita,A.;Suzuki,R.;Hayashi,T.;Morita,N.;Kawano,N.;Koshimura,S.,Studies on cytotoxic constituents in pericarps of Mallotusjaponicus,Part Ⅰ[J].J.Nat.Prod.1985,48,(3),455-459.
[9]Thakur,S.C.;Thakur,S.S.;Chaube,S.K.;Singh,S.P.,An etheral extract of Kamala[Mallotus philippinensis(Moll.Arg) Lam.]seed induce adverse effects on reproductive parameters of female rats[J].Reprod.Toxicol.2005,20,(1),149-156.
[10]Honma,H.,J.Agr.Chem.Soc.Japan 1939,15,394.
[11]Katsuhiko,O.;Hideo,N.;Meng,Z.M.;Youki,O.;Yoshimichi,S.;Mizuo,M.,Differential inhibitory effects of various herb extracts on the activities of reverse transcriptase and various deoxyribonucleic acid(DNA) polymerases[J].Chem.Pharm.Bull.1989,37,(7),1810-1812.
[12]Nair,S.P.;Madhusudana Rao,J.,Kamaladiol-3-acetate from the stem bark of Mallotus philippinensis[J].Phytochemistry 1993,32,(2),407-409.
[13]亓晓曼;杨益平;叶阳,白背叶茎的化学成分研究[J].中药材2005,28,(9),765-766.
[14]吴桂凡;韦松;蓝树彬;许学健,白背叶中一个新的异戊烯基二氢黄酮[J].中草药2006,37,(8),1126-1128.
[15]Huang,P.L.;Wang,L.W.;Lin,C.N.,New triterpenoids ofMallotus repandus[J].J.Nat.Prod.1999,62,(6),891-892.
[16]Hui,W.H.;Li,M.M.,Triterpenoids from two Mallotus species:a nor-triterpene and two new acids[J].Phytochemistry 1976,15,(6),985-986.
[17]Bandopadhyay,M.;Dhingra,V.K.;Mukerjee,S.K.;Pardeshi,N.P.;Seshadri,T.R.,Triterpenoid and other components of Mallotus Philippinensis[J].Phytochemistry 1972,11,(4),1511-1511.
[18]单雪琴,白背叶根化学成分的研究[J].植物学报 1984,27,(2),192-193.
[19]Pal,R.;Kulshreshtha,D.K.;Rastogi,R.P.,Mallotin-a new C32 triterpenoid from Mallotous stenanthus[J].Phytochemistry 1975,14,(10),2253-2255.
[20]Sutthivaiyakit,S.;Thongtan,J.;Pisutjaroenpong,S.;Jiaranantanont,K.;Kongsaeree,P.,D:A Friedo-oleanane lactones from the stems of Mallotus repandus[J].J.Nat.Prod 2001,64,(5),569-571.
[21]林连波:符小文;艾朝晖;申静;卫昆:李魏,海南山苦茶叶的化学成分研究I[J].中国中药杂志 2006,31,(6),477-479.
[22]Bai,Y.;Yang,Y.;Ye,Y.,Hookerianolides A-C:three novel casbane-type diterpenoid lactones from Mallotus hookerianus[J].Tetrahedron Lett.2006,47,(37),6637-6640.
[23]Cheng,X.F.;Chen,Z.L.,Three new diterpenoids from Mallotus apelta Muell.Arg[J].J.Asian Nat.Prod.Res.1999,1,(4),319-325.
[24]Cheng,X.F.;Chen,Z.L.;Meng,Z.M.,Two new diterpenoids from Mallotus apelta Muell.Arg[J].J.Asian Nat.Prod.Res.1999,1,(3),163-168.
[25]唐宗俭;宋纯清;冯胜初;杨益平;徐任生,锈毛野桐化学成分的研究Ⅰ[J].化学学报 1990,48,705-708.
[26]杨益平;唐宗俭;冯胜初;徐任生,锈毛野桐化学成分的研究Ⅲ[J].化学学报1992,50,200-204.
[27]杨益平;唐宗俭;徐任生,锈毛野桐化学成分的研究[J].化学学报 1992,50,205-208.
[28]李干鹏:杨丽娟;赵静峰;羊晓东;李良,滇黔野桐的化学成分研究[J].中草药2007,38,(6),804-806.
[29]Roberts,K.D.;Weiss,E.;Reichstein,T.,Die cardenolide der samen von Mallotus philipinensis(Lam.) Mull.-Arg[J].Helv.Chim.Acta.1963,46,(7),2886-2893.
[30]Roberts,K.D.;Weiss,E.;Reichstein,T.,Die cardenolide der samen von Mallotus paniculatus Muell.-Arg.(Euphorbiaceae).2[J].Helv.Chim.Acta.1967,50,(6),1645-1664.
[31]Okabe,H.;Inoue,K.;Yamauchi,T.,Studies on the constituents of Mallotus japonicus[J].Chem.Pharm.Bull 1976,24,(1),108-113.
[32]朱斌;白桂昌;蒋受军;魏峰;林瑞超,白背叶化学成分和含量测定研究[J].中国中药杂志2007,32,(10),932-934.
[33]Daikonya,A.;Katsuki,S.;Kitanaka,S.,Antiallergic Agents from Natural Sources 9.Inhibition of Nitric Oxide Production by Novel Chalcone Derivatives from Mallotus philippinensis (Euphorbiaceae)[J].Chem.Pharm.Bull.2004,52,(11),1326-1329.
[34]Tanaka,T.;Ito,T.;Iinuma,M.;Takahashi,Y.;Naganawa,H.,Dimeric chalcone derivatives from Mallotus philippensis[J].Phytochemisty 1998,48,(8),1423-1427.
[35]Ma,J.;Jones,S.H.;Hecht,S.M.,A Coumarin from Mallotus resinosus that Mediates DNA Cleavage[J].J.Nat.Prod.2004,67,(9),1614-1616.
[36]Cheng,X.F.;Chen,Z.L.,Coumarinolignoids of Mallotus apelta[J].Fitoterapia 2000,71,(3),341-342.
[37]Wei,K.;Li,W.;Koike,K.;Liu,L.;Fu,X.W.;Lin,L.B.;Chen,Y.J.;T.Nikaido,Two new galloylglucosides from the leaves of Mallotus furetianus[J].Chem.Pharm.Bull 2004,52,(6), 776-779.
[38]An,T.Y.;Hu,L.H.;Cheng,X.F.;Chen,Z.L.,Benzopyran derivatives from Mallotus apelta[J].Phytochemistry 2001,57,(2),273-278.
[39]Daikonya,A.;Katsuki,S.;Wu,J.B.;Kitanaka,S.,Anti-allergic agents from natural sources(4):anti-allergic activity of new phloroglucinol derivatives from Mallotus philippensis.(Euphorbiaceae)[J].Chem.Pharm.Bull.2002,50,(12),1566-1569.
[40]Supudompol,B.;Likhitwitayawuid,K.;Houghton,P.J.,Phloroglucinol derivatives from Mallotus pallidus[J].Phytochemistry 2004,65,(18),2589-2594.
[41]Arisawa,M.;Fujita,A.;Morita,N.;Okuyama,T.;Nishino,H.,Inhibition of Tumor-Promoter-Enhanced 3H-choline incorporation into cellular phospholipids by phloroglucinol derivatives from Mallotus japonicus[J].J.Nat.Prod.1991,54,(5),1409-1412.
[42]Fujita,A.;Hayashi,T.;Arisawa,M.;Shimizu,M.;Morita,N.;Kikruchi,T.;Tezuka,Y.,Studies on cytotoxic constituents in pericarps of Mallotus japonic,s,part Ⅲ[J].J.Nat.Prod.1988,51,(4),708-712.
[43]Saijo,R.;Nonaka,G.;Nishioka,I.,Gallic acid esters of bergenin and norbergenin from Mallotus japonicus[J].Phytochemistry 1990,29,(1),267-270.
[44]Yoshida,T.;Seno,K.;Takama,Y.;Okuda,T.,Bergenin derivatives from Mallotus japonicus[J].Phytochemistry 1982,21,(5),1180-1182.
[45]Okuda,T.;Seno,K.,Mallotusinic acid and mallotinic acid,new hydrolyzable tannins from Mallotus japonicus[J].Tetrahedron Lett.1978,19,(2),139-142.
[46]Cheng,X.F.;Meng,Z.M.;Chen,Z.L.,A pyridine-type alkaloid from Mallotus apelta[J].Phytochemistry 1998,49,(7),2193-2194.
[47]Kouno,I.;Shigematsu,N.;Iwagami,M.;Kawano,N.,Further phloroglucinol derivatives in the fruits of Mallotus japonicus[J].Phytochemistry 1985,24,(3),620-621.
[48]康飞;吕华冲,广西白背叶植物叶的化学成分[J].广东药学院学报 2007,23,(2),121-123.
[49]Suga,T.;Shishibori,T.;Nakaya,K.,Structure and biosynthesis of malloprenols from Mallotus japonicus[J].Phytochemistry 1980,19,(11),2327-2330.
[50]李吉来;陈飞龙;吕志平,白背叶根挥发性成分的研究[J].中药材 2003,26,(10),723-724.
[51]赵进军;吕志平;张绪富,白背叶根对肝纤维化大鼠的实验研究[J].现代诊断与治疗 2002.13,(5),257-259.
[52]赵进车;吕志平;张绪富,白背叶根对过氧化氢所致大鼠肝细胞损伤的保护作用[J].华西药学杂志 2003,18,(4),257-259.
[53]Thakur,S.C.;Thakur,S.S.;Chaube,S.K.;Singh,S.P.,An etheral extract of kamala(Mallotus philippinensis(Moll.-Arg.)Lam.) seed induce adverse effects on reproductive parameters of female rats[J].Reprod.Toxicol.2005,20,149-156.
[54]Chattopadhyay,D.;Arunachalam,G.;Mandal,A.B.;sUR,T.k.,Antimicrobial and anti-inflammatory activity of folklore:Mallotus peltatus leaf extract[J].J.Ethnopharmacol.2002,82,229-237.
[55]Intahpuak,S.;Panthong,A.;Kanjanapothi,D.;Taesotikul,T.,Anti-inflammatory and analgesic activities of Mallotus spodocarpus airy shaw[J].J.Ethnopharmacol.2004,90,69-72.
[56]Ishii,R.;Horie,M,;Koichi,Inhibition of lipopolysaccharide-induced pro-inflammatory cytokine expression via suppression of nuclear factor-KB activation by Mallotus japonicus phloroglucinol derivatives[J].Biochim.Biophys.Acta 2003,1620,108-118.
[57]Chattopadhyay,D.;Arunachalam,G.;Mandal,A.B.;S.C.Mandal,Evaluation of antipyretic activity of leaf extracts of Mallotus peltatus(Geist) Muell.Arg.var acuminatus:A folk medicine[J].Phytomedicine 2002,9,727-730.
[58]Katsube,T.;Tabata,H.;Ohta,Y.;Yamasaki,Y.,Screening for antioxidant activity in edible plant products:comparison of low-density lipoprotein oxidation assay,DPPH radical scavenging assay,and Folin-Ciocalteu assay[J].J.Agr.Food Chem.2004,52,2391-2392.
[59]谢金鲜:林启云;黄启武;罗明;王蔚,复方白背叶的药理研究Ⅰ[J].广西中医药 1993,16,(2),43-46.
[60]黄国东;李卫红;方显明,复方白背叶胶囊对急性上消化道出血疗效的序贯试验观察[J].广西中医药 1996,19,(1),4-5.
[61]谢金鲜;林启云;黄启武;罗明;王蔚,复方白背叶的药理研究Ⅱ[J].广西中医药 1994,17,(2),45-47.
[62]刘月丽;伍海涛;王立群;林连波,山苦茶提取物对动脉粥样硬化大鼠血管内皮功能的影响[J].中国热带医学 2008,8,(3),384-389.
[1]中国科学院中国植物志编辑委员会,中国植物志.第二十四卷第二分册[M].北京:科学出版社,1996.
[2]全国中草药汇编编写组,全国中草药汇编[M].北京:人民卫生出版社,1975:297.
[3]Lee,D.;Cuendet,M.;Vigo,J.S.;Graham,J.G.;Cabieses,F.;Fong,H.H,S.;Pezzuto,J.M.;Kinghom,A.D.,A novel cyclooxygenase-inhibitory stilbenolignan from the seeds of Aiphanes aculeata[J].Org.Lett.2001,3,(14),2169-2171.
[4]Cheng,X.F.;Chen,Z.L.,Coumarinolignoids of Mallotus apelta[J].Fitoterapia 2000,71,(3),341-342.
[5]Kikuzaki,H.;Kayano,S.;Fukutsuka,N.;Aoki,A.;Kasamatsu,K.;Yamasaki,Y.;Mitani,T.;Nakatani,N.,Abscisic acid related compounds and lignans in prunes(Prunus domestica L.) and their oxygen radical absorbancecapacity(ORAC)[J].J.Agric.Food Chem.2004,52,(2),344-349.
[6]Ray,A.B.;Chattopadhyay,S.K.;Kumar,S.;Konno,C.;Kiso,Y.;Hikino,H.,Structures of cleomiscosins,coumarinolignoids of Cleome viscosa seeds[J].Tetrahedron 1985,41,(1),209-214.
[7]Shimomura,H.;Sashida,Y.;Oohara,M.,Lignans from Machilus thunbergii[J].Phytochemistry 1988,27,(2),634-636.
[8]Bhandari,P.;Pant,P.;Rastogi,R.P.,Aquillochin,a coumarinolignan from Aquilaria agallocha[J].Phytochemistry 1982,21,(8),2147-2149.
[9]Champavier,Y.;Comte,G.;Vercauteren,J.;Allais,D.P.;Chulia,A.J.,Norterpenoid and sesquiterpenoid glucosides from Juniperus phynicea and Galega officinalis[J].Phytochemistry 1999,50,(7),1219-1223.
[10]顾正兵;陈新建;杨根金;李廷钊;刘文庸;张卫东,糙叶败酱活性成分的研究[J].中药材2002,25,(3),178-180.
[11]Takani,M.;Ohya,K.;Takahashi,K.,Studies on constituents of medicinal plants.Ⅹ Ⅻ.constituents of Schizandra nigra Max[J].Chem.Pharm.Bull.1979,27,(6),1422-1425.
[12]Sakurai,N.;Kobayashi,M.;Shigihara,A.;Inoue,T.,Berchemolide,a novel dimeric vanillic acid glucoside from Berchemia racemosa[J].Chem.Pharm.Bull.1992,40,(4),851-853.
[13]Jung,J.H.;Lee,C.O.;Kim,Y.C.;Kang,S.S.,New Bioactive Cerebrosides from Arisaema amurense[J].J.Nat.Prod.1996,59,(3),319-322.
[14]刘文粢;何凤雷:阮子镛;顾熊飞,狼毒大戟的化学成分研究[J].中国中药杂志 2001,26,(3),180-182.
[15]Ito,A.;Chai,H.B.;Kardono,L.B.S.;Setowati,F.M.;Afriastini,J.J.;Riswan,S.;Farnsworth,N.R.;Cordell,G.A.;Pezzuto,J.M.;Swanson,S.M.;Kinghorn,A.D.,Saponins from the bark of Nephelium maingayi[J].J.Nat.Prod.2004,67,(2),201-205.
[16]Abdel-Mogib,M.,A lupane triterpenoid from Maerua oblongifolia[J].Phytochemistry 1999,51,(3),445-448.
[17]Chaudhuri,S.K.;Fullas,F.;Brown,D.M.;Wani,M,C.;Wall,M.E.;Cai,L.;Mar,W.;Lee,S.K.;Luo,Y.;Zaw,K.;Fong,H.H.S.;Pezzuto,J.M.;Kinghorn,A.D.,Isolation and structural elucidation of pentacyclic triterpenoids from Maprounea africana[J].J.Nat.Prod.1995,58,(1),1-9.
[18]梁爽;陈海生;金永生;金丽;卢嘉;杜景伶,海南狗牙花化学成分研究[J].中国中药杂志2007,32,(13),1296-1299.
[19]Yang,S.M.;Liu,X.K.;Qing,C.;Wu,D.G.;Zhu,D.Y.,Chemical constituents from the roots of Homonoia riparia[J].Acta.Pharm.Sinica 2007,42,(3),285-289.
[20]Kojima,H.;Sato,N.;Hatano,A.;Ogura,H.,Sterol glucosides from Prunella vulgaris[J].Phytochemistry 1990,29,(7),2351-2355.
[21]何际婵;韦松;蓝树彬;许学健,黄杞茎皮化学成分研究[J].中草药 2006,37,(12),1788-1789.
[22]Cheng,M.J.,Chemical and cytotoxic constituents from the stem of Machilus zuihoensis[J].Helv Chim.Acta.2002,85,(7),1909-1914.
[1]中国植物志编委会,中国植物志 第三十七卷[M].北京:科学出版社,1985:223-331.
[2]江苏新医学院,中药大辞典[M].上海:上海科学技术出版社,1975:2705-2708.
[3]韦薇;陈锋;沈爱华,蕨麻的化学成分和药理作用研究进展[J].中国现代医药杂志 2008,10,(1),131-132.
[4]Bilia,A.R.;Palme,E.;Catalano,S.;Flamini,G.;Morelli,I.,New triterpenoid saponins from the roots of Potentilla tormentilla[J].J.Nat.Prod.1994,57,(3),333-338.
[5]薛培凤;乔梁;梁鸿;赵玉英,多裂委陵菜化学成分的研究[J].北京大学学报(医学版) 2004,36,(1),21-23.
[6]刘普;潘勤;张彦文;姚智,委陵菜三萜成分研究[J].中国中药杂志 2006,31,(22),1875-1879.
[7]王庆贺;李志勇;沈阳;林厚文;舒薇;周剑斌,委陵菜三帖类化学成分研究.中国中药杂志2006,31,(17),1434-1436.
[8]Li,P.L.;Zhang,Z.X.;Jia,Z.J.,A new taraxastane-type triterpenoid from Potentilla multicaulis[J].Chin.Chem.Lett.2006,17,(12),1573-1575.
[9]洪霞;蔡光明;韩晋;袁海龙;刘峰群;赵艳玲,新化合物蕨麻苷的结构鉴定[J].解放军药学学报 2004,20,(6),411-414.
[10]薛培凤;路新华;王邠;梁鸿;赵玉英,多裂委陵菜中的四甲基环己烯型单萜苷[J].中国中药杂志 2005,30,(13),983-986.
[11]邹俊利,翻白草的研究进展[J].黑龙江医药科学 2006,29,(4),104-105.
[12]冯卫生;郑晓珂;吉田隆志;奥田拓男,翻白草根中可水解单宁的研究[J].天然产物研究与开发1996,8,(3),27-29.
[13]Xue,P.F.;Liang,H.;Wang,B.;Zhao,Y.Y.,Chemical constituents from Potentilla multifida L.[J].J.Chin.Pharm.Sci.2005,14,(2),86-88.
[14]钟海军;陈纪军;王惠共;罗士德,翻白叶的化学成分[J].中草药 2000,31,(7),488-490.
[15]高雯;沈阳:张红军;汤华;林厚文;邱峰,委陵菜的化学成分研究[J].药学服务与研究2007,7,(4),262-264.
[16]薛培凤;李胜荣;雷静怡;李丽,委陵菜中酸性成分研究[J].内蒙古医学院学报 2007,29,(5),313-315.
[17]Wilkes,S.;Glasl,H.,Isolation,characterization,and systematic significance of 2-pyrone-4,6-dicarboxylic acid in Rosaceae[J].Phytochemistry 2001,58,(3),441-449.
[18]蔡玉华;刘梁;刘长林,三叶委陵菜根化学成分的研究[J].武汉理工大学学报 2005,27,(9),32-33.
[19]张颖;张立木;高允升;齐永秀;李同德;王晓丹,高效液相色谱法测定翻白草中没食子酸含量[J].中国医院药学杂志 2006,26,(3),355-356.
[20]赵国丁;陈建平;袁少飞,蕨麻多糖的含量测定及定性鉴别[J].今日科苑 2007,20,173-174.
[21]皮立;胡凤祖,臧药蕨麻油脂化合物的GC-MS分析[J].中草药2007,38,(11),1625-1627.
[22]Syiem,D.;Syngai,G.;Khup,P.Z.;Khongwir,B.S.;Kharbuli,B.;Kayang,H.,Hypoglycemic effects of Potentilla fulgens L.in normal and alloxan-induced diabetic mice[J].J.Ethnopharmacology 2002,83,55-61.
[23]Zhao,Y.L.;Cai,G.M.;Hong,X.;Shan,L.M.;Xiao,X.H.,Anti-hepatitis B virus activities of triterpenoid saponin compound from Potentilla anserine L.[J].Phytomedicine 2008,15,253-258.
[24]刘梁;韩定献;周军;刘长林;杨占秋,三叶委陵菜根中三萜类化合物抗病毒作用研究[J].时珍国医国药2006,17(8),1484-1485.
[25]Chen,K.L.;Plumb,G.W.;Bennett,R.N.;Bao,Y.P.,Antioxidant activities of extracts from five anti-viral medicinal plants[J].J.Ethnopharmacology 2005,96,201-205.
[26]Gürbüz,I.;Ozkan,A.M.;Yesilada,E.;Kutsal,O.,Anti-ulcerogenic activity of some plants used in folk medicine of P inarbasi(Kayseri,Turkey)[J].J.Ethnopharmacology 2005,101,313-318.
[27]向红,民间草药西南委陵菜抗菌作用的实验[J].贵州师范大学学报(自然科学版)2003,21,(2),55-57.
[28]边可君;徐辉碧;黄开勋;韩定献,三叶委陵菜乙醇提取物镇痛作用的研究[J].江苏临床医学杂志2002,6,(3),200-203.
[29]李贞;张铁权;叶亮;贾玉海,委陵菜对四氯化碳致小鼠肝损伤保护作用[J].辽宁中医杂志2004,31,(5),422-423.
[30]李贞;程留芳;张铁权;李舒;贾上海,委陵菜防治四氯化碳致大鼠肝纤维化实验研究[J].辽宁中医杂志 2007,2007,(34),8.
[31]李灵芝;张丽;龚海英,蕨麻醇提取物的抗缺氧与抗氧化研究[J].中国食品卫生杂志 2005,4,(17),306-308.
[1]王晋;张坚;康胜利,青海产蕨麻营养成分的研究[J].青海医药杂志 1998,28,(2),52-53.
[2]Montaudo,G.;Caccamese,S.,Structure and conformation of chalcone photodimers and related compounds[J].J.Org.Chem.1973,33,(4),710-716.
[3]Ben-Efraim,D.A.;Green,B.S.,The use of mid-points or average NMR chemical shifts in stereochemical assignments[J],Tetrahedron 1974,30,2357-2364.
[4]El-Ansari,M.A.;Nawwar,M.A.;Saleh,N.A.M.,Stachysetin,a diapigenin-7-glucosidep,p'-dihydroxy-truxinate from Stachys aegyptiaca[J].Phytochemistry 1995,40,(5),1543-1548.
[5]Isaza,J.H.;Ito,H.;Yoshida,T.,A flavonol glycoside-lignan ester and accompanying acylated glucosides from Monochaetum multiflorum[J].Phytochemistry 2001,58,(2),321-327.
[6]Daniel,O.,A new general synthesis of 2,2-dialkyl-2,3-dihydro-4H-pyran-4-ones and their application for the in situ preparation of electron-rich dienes in carbonyl-alkyne exchange reactions with acetylenes[J].Helvetica Chimica Acta 1991,74,(1),27-46.
[7]Tsukamoto,S.;Tomise,K.;Aburatani,M.;Onuki,H.;Hirorta,H.;Ishiharajima,E.;Ohta,T.,Isolation of cytochrome P450 inhibitors from strawberry fruit,Fragaria ananassa[J].J.Nat.Prod.2004,67,(11),1839-1841.
[8]Hohmann,J.;Pall,Z.;Gunther,G.;Mathe,I.,Flavonolacyl glycosides of the aerial parts of Erynqium campestre[J].Planta Med.1997,63,(1),96.
[9]Rayyan,S.;Fossen,T.;Andersen,O.M.,Flavone C-glycosides from leaves of Oxalis triangularis[J].J.Agric.Food Chem.2005,53,(26),10057-10060.
[10]Xie,C.;Veitch,N.C.;Houghton,P.J.;Simmonds,M.S.J.,Flavone C-glycosides from Viola yedoensis Makino[J].Chem.Pharm.Bull.2003,51,(10),1204-1207.
[11]Wang,M.;Kikuzaki,H.;Csiszar,K.;Boyd,C.D.;Maunakea,A.;Fong,S.F.T.;Ghai,G.;Rosen,R.T.;Nakatani,N.;Ho,C.T.,Novel trisaccharide fatty acid ester identified from the fruits of Morinda citrifolia(Noni)[J].J.Agric.Food Chem.1999,47,(12),4880-4882.
[12]黄胜阳;石建功;杨永春;胡世林,长苞凹舌兰化学成分研究[J].药学学报 2002,37,(3),199-203.
[13]Topcu,G.;Ay,M.;Bilici,A.;Sarikurkcu,C.;Ulubelen,A.,A new flavone from antioxidant extracts of Pistacia terebinthus[J].Food Chemistry 2007,103,(3),816-822.
[14]Hsu,H.F.;Houng,J.Y.;Chang,C.L.;Wu,C.C.;Chang,F.R.;Wu,Y.C.,Antioxidant activity, cytotoxicity,and DNA information of Glossogyne tenuifolia[J].J.Agric.Food Chem.2005,53,(15),6117-6125.
[15]Errea,M.I.;Matulewicz,M.C.,Cold water-soluble polysaccharides from tetrasporic Pterocladia capillacea[J].Phytochemistry 1994,37,(4),1075-1078.
[16]Bertrand Alluis,O.D.,Quercetin(=2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one)glycosides and sulfates:chemical synthesis,complexation,and antioxidant properties[J].Helvetica Chimica Acta 2001,84,(5),1133-1156.
[17]Kim,H.Y.;Moon,B.H.;Lee,H.J.;Choi,D.H.,Flavonol glycosides from the leaves of Eucommia ulmoides O.with glycation inhibitory activity[J].Journal of Ethnopharmacology 2004,93,(2-3),227-230.
[18]Zou,Y.;Kim,A.R.;Kim,J.E.;Choi,J.S.;Chung,H.Y.,Peroxynitrite scavenging activity of sinapic acid(3,5-dimethoxy-4-hydroxycinnamic acid) isolated from Brassica juncea[J].J.Agric.Food Chem.2002,50,(21),5884-5890.
[19]Merfort,I.;Wendisch,D.,Flavonoid glucuronides from the flowers of Arnica montana[J].Planta Med.1988,54,(3),247-250.
[20]吴海峰:潘莉;丁立生;张晓峰,臧药五脉绿绒蒿的化学成分研究[J].天然产物研究与开发 2007,19,811-813.
[21]顾正兵;陈新建;杨根金;李廷钊;刘文庸;张卫东,糙叶败酱活性成分的研究[J].中药材2002,25,(3),178-180.
[22]李占林;李丹毅;李铣;李宁;孟大利,文冠果果壳中一个新生物碱[J].药学学报2006,42,(12),1197-1200.
[23]Kimura,J.;Maki,N.,New loliolide derivatives from the brown alga Undaria pinnatifida[J].J.Nat.Prod.2002,65,(1),57-58.
[24]Champavier,Y.;Comte,G.;Vercauteren,J.;Allais,D.P.;Chulia,A.J.,Norterpenoid and sesquiterpenoid glucosides from Juniperus phynicea and Galega officinalis[J].Phytochemistry 1999,50,(7),1219-1223.
[25]Yan,X.H.;Guo,Y.W.,Two new ellagic acid glycosides from leaves of diplopanax stachyanthus[J].J.Asian Nat.Prod.Res.2004,6,(4),271-276.
[26]Khallouki,F.;Haubner,R.;Hull,W.E.;Erben,G.:Spiegelhalder,B.;Bartsch,H.;Owen,R.W.,Isolation,purification and identification of ellagic acid derivatives,catechins,and procyanidins from the root bark of Anisophyllea dichostyla R.[J],Br.Food and Chemical Toxicology 2007,45,(3),472-485.
[27]石心红;杜晓犁;孔令义,准噶尔大戟根化学成分的研究[J].中国中药杂志 2006,31,(18),1503-1506.
[28]Baderschneider,B.;Winterhalter,P.,Isolation and Characterization of Novel benzoates,cinnamates,flavonoids,and lignans from riesling wine and screening for antioxidant activity[J].J.Agric.Food Chem.2001,49,(6),2788-2798.
[29]Perry,N.B.;Benn,M.H.;Foster,L.M.;Routledge,A.;Weavers,R.T.,The glycosidic precursor of(Z)-5-ethylidene-2(5H)-furanone in Halocarpus biformis juvenile foliage[J],Phytochemistry 1996,42,(2),453-459.
[30]Li,W.-W.;Barz,W.,Structure and accumulation of phenolics in elicited Echinacea purpurea Cell Cultures[J].Planta Medica 2005,(3),248-254.
[31]邱鹰昆;窦德强;裴玉萍;吉川雅之;松田久司;陈英杰,仙人掌的化学成分研究[J].中国药科大学学报 2005,36,(3),213-215.
[32]H.,T.;D.,T.;T.,H.;K.,N.,Stable isotope-labeling studies on the oxidative coupling of caffeic acid via o-quinone[J].Biosci.Biotech.Biochem.2001,65,(12),2613-2621.
[33]张悦;阮汉利;张勇慧;皮惠芳;吴继洲,鄂西大蓟化学成分的研究[J].医药导报 2007,26,(12),1425-1426.
[34]王伟;赵庆春;安晔;吴立军,中药蜂房的化学成分研究[J].中国药物化学杂志 2008,18,(1),54-55.
[35]李药兰;苏妙贤;岑颖洲;叶文才,小紫金牛的化学成分研究[J].中药材 2006,29,(4),331-333.
[36]Karonen,M.;Hamalainen,M.;Nieminen,R.;Klika,K.D.;Loponen,J.;Ovcharenko,V.V.;Moilanen,E.;Pihlaja,K.,Phenolic extractives from the bark of Pinus sylvestris L.and their effects on inflammatory mediators nitric oxide and prostaglandin E2[J].J.Agric.Food Chem.2004,52,(25),7532-7540.
[37]孙东东;李祥;陈建伟;何立巍,板蓝根醇提部位化学成分研究[J].中国药房 2007,18,(30),2325-2326.
[38] 李云森;罗士德;张勉;陈纪军;王峥涛,棉毛橐吴的化学成分[J].中国中药杂志 2001,26,(12),835-837.
[39]Nakatani,N.;Kayano,S.;Kikuzaki,H.;Sumino,K.;Katagiri,K.;Mitani,T.,Identification,quantitative determination,and antioxidative activities of chlorogenic acid isomers in prune (Prunus domestica L.)[J].J.Agric.Food Chem.2000,48,(11),5512-5516.
[40]丁丽丽;王顺春;王峥涛,猫人参化学成分的研究[J].中国中药杂志 2007,32,(18),1893-1895.
[41]袁干军;杜方麓,硕苞蔷薇果的化学成分研究[J].中药材 2000,23,(8),454-456.
[42]赵爱华;赵勤实;彭丽艳;孙汉董,鬼针草中一个新的查耳酮苷[J].云南植物研究 2004,26,(1),121-126.
[43]Chen,P.;Tucker,W.;Dauterman,W.,Structure of biologically produced malathion monoacid[J].J.Agric.Food Chem.1969,17,(1),86-90.
[44]沈德凤;杨波;付红伟,翻白草中熊果酸的含量测定[J].中国野生植物资源 2002,21,(4),55-56.
[2]全国中草药汇编编写组,全国中草药汇编M].北京:人民卫生出版社,1975:297.
[3]浙江药用植物志编写组,浙江药用植物志[M].杭州:浙江科学技术出版社,1980:715.
[4]中国科学院昆明植物研究所,云南种子植物名录[M].昆明:云南人民出版社,1984:447.
[5]刘国民;李娟玲;王小精;何秋香,海南鸱鸪茶的民族植物学研究[J].海南师范大学学报(自然科学版) 2007,20,(2),167-171.
[6]Okabe,H.;Inoue,K.;Yamauchi,T.,Studies on the constituents of Mallotus japonicus Muell.Arg.L.cardiac glycosides from the seeds[J].Chem.Pharm.Bull.1976,24,(1),108-113.
[7]Shigematsu,N.;Kouno,I.;Kawano,N.,Phloroglucinol derivatives from fruits of Mallotus japonicus[J].Phytochemistty 1983,22,(1),323-325.
[8]Arisawa,M.;Fujita,A.;Suzuki,R.;Hayashi,T.;Morita,N.;Kawano,N.;Koshimura,S.,Studies on cytotoxic constituents in pericarps of Mallotusjaponicus,Part Ⅰ[J].J.Nat.Prod.1985,48,(3),455-459.
[9]Thakur,S.C.;Thakur,S.S.;Chaube,S.K.;Singh,S.P.,An etheral extract of Kamala[Mallotus philippinensis(Moll.Arg) Lam.]seed induce adverse effects on reproductive parameters of female rats[J].Reprod.Toxicol.2005,20,(1),149-156.
[10]Honma,H.,J.Agr.Chem.Soc.Japan 1939,15,394.
[11]Katsuhiko,O.;Hideo,N.;Meng,Z.M.;Youki,O.;Yoshimichi,S.;Mizuo,M.,Differential inhibitory effects of various herb extracts on the activities of reverse transcriptase and various deoxyribonucleic acid(DNA) polymerases[J].Chem.Pharm.Bull.1989,37,(7),1810-1812.
[12]Nair,S.P.;Madhusudana Rao,J.,Kamaladiol-3-acetate from the stem bark of Mallotus philippinensis[J].Phytochemistry 1993,32,(2),407-409.
[13]亓晓曼;杨益平;叶阳,白背叶茎的化学成分研究[J].中药材2005,28,(9),765-766.
[14]吴桂凡;韦松;蓝树彬;许学健,白背叶中一个新的异戊烯基二氢黄酮[J].中草药2006,37,(8),1126-1128.
[15]Huang,P.L.;Wang,L.W.;Lin,C.N.,New triterpenoids ofMallotus repandus[J].J.Nat.Prod.1999,62,(6),891-892.
[16]Hui,W.H.;Li,M.M.,Triterpenoids from two Mallotus species:a nor-triterpene and two new acids[J].Phytochemistry 1976,15,(6),985-986.
[17]Bandopadhyay,M.;Dhingra,V.K.;Mukerjee,S.K.;Pardeshi,N.P.;Seshadri,T.R.,Triterpenoid and other components of Mallotus Philippinensis[J].Phytochemistry 1972,11,(4),1511-1511.
[18]单雪琴,白背叶根化学成分的研究[J].植物学报 1984,27,(2),192-193.
[19]Pal,R.;Kulshreshtha,D.K.;Rastogi,R.P.,Mallotin-a new C32 triterpenoid from Mallotous stenanthus[J].Phytochemistry 1975,14,(10),2253-2255.
[20]Sutthivaiyakit,S.;Thongtan,J.;Pisutjaroenpong,S.;Jiaranantanont,K.;Kongsaeree,P.,D:A Friedo-oleanane lactones from the stems of Mallotus repandus[J].J.Nat.Prod 2001,64,(5),569-571.
[21]林连波:符小文;艾朝晖;申静;卫昆:李魏,海南山苦茶叶的化学成分研究I[J].中国中药杂志 2006,31,(6),477-479.
[22]Bai,Y.;Yang,Y.;Ye,Y.,Hookerianolides A-C:three novel casbane-type diterpenoid lactones from Mallotus hookerianus[J].Tetrahedron Lett.2006,47,(37),6637-6640.
[23]Cheng,X.F.;Chen,Z.L.,Three new diterpenoids from Mallotus apelta Muell.Arg[J].J.Asian Nat.Prod.Res.1999,1,(4),319-325.
[24]Cheng,X.F.;Chen,Z.L.;Meng,Z.M.,Two new diterpenoids from Mallotus apelta Muell.Arg[J].J.Asian Nat.Prod.Res.1999,1,(3),163-168.
[25]唐宗俭;宋纯清;冯胜初;杨益平;徐任生,锈毛野桐化学成分的研究Ⅰ[J].化学学报 1990,48,705-708.
[26]杨益平;唐宗俭;冯胜初;徐任生,锈毛野桐化学成分的研究Ⅲ[J].化学学报1992,50,200-204.
[27]杨益平;唐宗俭;徐任生,锈毛野桐化学成分的研究[J].化学学报 1992,50,205-208.
[28]李干鹏:杨丽娟;赵静峰;羊晓东;李良,滇黔野桐的化学成分研究[J].中草药2007,38,(6),804-806.
[29]Roberts,K.D.;Weiss,E.;Reichstein,T.,Die cardenolide der samen von Mallotus philipinensis(Lam.) Mull.-Arg[J].Helv.Chim.Acta.1963,46,(7),2886-2893.
[30]Roberts,K.D.;Weiss,E.;Reichstein,T.,Die cardenolide der samen von Mallotus paniculatus Muell.-Arg.(Euphorbiaceae).2[J].Helv.Chim.Acta.1967,50,(6),1645-1664.
[31]Okabe,H.;Inoue,K.;Yamauchi,T.,Studies on the constituents of Mallotus japonicus[J].Chem.Pharm.Bull 1976,24,(1),108-113.
[32]朱斌;白桂昌;蒋受军;魏峰;林瑞超,白背叶化学成分和含量测定研究[J].中国中药杂志2007,32,(10),932-934.
[33]Daikonya,A.;Katsuki,S.;Kitanaka,S.,Antiallergic Agents from Natural Sources 9.Inhibition of Nitric Oxide Production by Novel Chalcone Derivatives from Mallotus philippinensis (Euphorbiaceae)[J].Chem.Pharm.Bull.2004,52,(11),1326-1329.
[34]Tanaka,T.;Ito,T.;Iinuma,M.;Takahashi,Y.;Naganawa,H.,Dimeric chalcone derivatives from Mallotus philippensis[J].Phytochemisty 1998,48,(8),1423-1427.
[35]Ma,J.;Jones,S.H.;Hecht,S.M.,A Coumarin from Mallotus resinosus that Mediates DNA Cleavage[J].J.Nat.Prod.2004,67,(9),1614-1616.
[36]Cheng,X.F.;Chen,Z.L.,Coumarinolignoids of Mallotus apelta[J].Fitoterapia 2000,71,(3),341-342.
[37]Wei,K.;Li,W.;Koike,K.;Liu,L.;Fu,X.W.;Lin,L.B.;Chen,Y.J.;T.Nikaido,Two new galloylglucosides from the leaves of Mallotus furetianus[J].Chem.Pharm.Bull 2004,52,(6), 776-779.
[38]An,T.Y.;Hu,L.H.;Cheng,X.F.;Chen,Z.L.,Benzopyran derivatives from Mallotus apelta[J].Phytochemistry 2001,57,(2),273-278.
[39]Daikonya,A.;Katsuki,S.;Wu,J.B.;Kitanaka,S.,Anti-allergic agents from natural sources(4):anti-allergic activity of new phloroglucinol derivatives from Mallotus philippensis.(Euphorbiaceae)[J].Chem.Pharm.Bull.2002,50,(12),1566-1569.
[40]Supudompol,B.;Likhitwitayawuid,K.;Houghton,P.J.,Phloroglucinol derivatives from Mallotus pallidus[J].Phytochemistry 2004,65,(18),2589-2594.
[41]Arisawa,M.;Fujita,A.;Morita,N.;Okuyama,T.;Nishino,H.,Inhibition of Tumor-Promoter-Enhanced 3H-choline incorporation into cellular phospholipids by phloroglucinol derivatives from Mallotus japonicus[J].J.Nat.Prod.1991,54,(5),1409-1412.
[42]Fujita,A.;Hayashi,T.;Arisawa,M.;Shimizu,M.;Morita,N.;Kikruchi,T.;Tezuka,Y.,Studies on cytotoxic constituents in pericarps of Mallotus japonic,s,part Ⅲ[J].J.Nat.Prod.1988,51,(4),708-712.
[43]Saijo,R.;Nonaka,G.;Nishioka,I.,Gallic acid esters of bergenin and norbergenin from Mallotus japonicus[J].Phytochemistry 1990,29,(1),267-270.
[44]Yoshida,T.;Seno,K.;Takama,Y.;Okuda,T.,Bergenin derivatives from Mallotus japonicus[J].Phytochemistry 1982,21,(5),1180-1182.
[45]Okuda,T.;Seno,K.,Mallotusinic acid and mallotinic acid,new hydrolyzable tannins from Mallotus japonicus[J].Tetrahedron Lett.1978,19,(2),139-142.
[46]Cheng,X.F.;Meng,Z.M.;Chen,Z.L.,A pyridine-type alkaloid from Mallotus apelta[J].Phytochemistry 1998,49,(7),2193-2194.
[47]Kouno,I.;Shigematsu,N.;Iwagami,M.;Kawano,N.,Further phloroglucinol derivatives in the fruits of Mallotus japonicus[J].Phytochemistry 1985,24,(3),620-621.
[48]康飞;吕华冲,广西白背叶植物叶的化学成分[J].广东药学院学报 2007,23,(2),121-123.
[49]Suga,T.;Shishibori,T.;Nakaya,K.,Structure and biosynthesis of malloprenols from Mallotus japonicus[J].Phytochemistry 1980,19,(11),2327-2330.
[50]李吉来;陈飞龙;吕志平,白背叶根挥发性成分的研究[J].中药材 2003,26,(10),723-724.
[51]赵进军;吕志平;张绪富,白背叶根对肝纤维化大鼠的实验研究[J].现代诊断与治疗 2002.13,(5),257-259.
[52]赵进车;吕志平;张绪富,白背叶根对过氧化氢所致大鼠肝细胞损伤的保护作用[J].华西药学杂志 2003,18,(4),257-259.
[53]Thakur,S.C.;Thakur,S.S.;Chaube,S.K.;Singh,S.P.,An etheral extract of kamala(Mallotus philippinensis(Moll.-Arg.)Lam.) seed induce adverse effects on reproductive parameters of female rats[J].Reprod.Toxicol.2005,20,149-156.
[54]Chattopadhyay,D.;Arunachalam,G.;Mandal,A.B.;sUR,T.k.,Antimicrobial and anti-inflammatory activity of folklore:Mallotus peltatus leaf extract[J].J.Ethnopharmacol.2002,82,229-237.
[55]Intahpuak,S.;Panthong,A.;Kanjanapothi,D.;Taesotikul,T.,Anti-inflammatory and analgesic activities of Mallotus spodocarpus airy shaw[J].J.Ethnopharmacol.2004,90,69-72.
[56]Ishii,R.;Horie,M,;Koichi,Inhibition of lipopolysaccharide-induced pro-inflammatory cytokine expression via suppression of nuclear factor-KB activation by Mallotus japonicus phloroglucinol derivatives[J].Biochim.Biophys.Acta 2003,1620,108-118.
[57]Chattopadhyay,D.;Arunachalam,G.;Mandal,A.B.;S.C.Mandal,Evaluation of antipyretic activity of leaf extracts of Mallotus peltatus(Geist) Muell.Arg.var acuminatus:A folk medicine[J].Phytomedicine 2002,9,727-730.
[58]Katsube,T.;Tabata,H.;Ohta,Y.;Yamasaki,Y.,Screening for antioxidant activity in edible plant products:comparison of low-density lipoprotein oxidation assay,DPPH radical scavenging assay,and Folin-Ciocalteu assay[J].J.Agr.Food Chem.2004,52,2391-2392.
[59]谢金鲜:林启云;黄启武;罗明;王蔚,复方白背叶的药理研究Ⅰ[J].广西中医药 1993,16,(2),43-46.
[60]黄国东;李卫红;方显明,复方白背叶胶囊对急性上消化道出血疗效的序贯试验观察[J].广西中医药 1996,19,(1),4-5.
[61]谢金鲜;林启云;黄启武;罗明;王蔚,复方白背叶的药理研究Ⅱ[J].广西中医药 1994,17,(2),45-47.
[62]刘月丽;伍海涛;王立群;林连波,山苦茶提取物对动脉粥样硬化大鼠血管内皮功能的影响[J].中国热带医学 2008,8,(3),384-389.
[1]中国科学院中国植物志编辑委员会,中国植物志.第二十四卷第二分册[M].北京:科学出版社,1996.
[2]全国中草药汇编编写组,全国中草药汇编[M].北京:人民卫生出版社,1975:297.
[3]Lee,D.;Cuendet,M.;Vigo,J.S.;Graham,J.G.;Cabieses,F.;Fong,H.H,S.;Pezzuto,J.M.;Kinghom,A.D.,A novel cyclooxygenase-inhibitory stilbenolignan from the seeds of Aiphanes aculeata[J].Org.Lett.2001,3,(14),2169-2171.
[4]Cheng,X.F.;Chen,Z.L.,Coumarinolignoids of Mallotus apelta[J].Fitoterapia 2000,71,(3),341-342.
[5]Kikuzaki,H.;Kayano,S.;Fukutsuka,N.;Aoki,A.;Kasamatsu,K.;Yamasaki,Y.;Mitani,T.;Nakatani,N.,Abscisic acid related compounds and lignans in prunes(Prunus domestica L.) and their oxygen radical absorbancecapacity(ORAC)[J].J.Agric.Food Chem.2004,52,(2),344-349.
[6]Ray,A.B.;Chattopadhyay,S.K.;Kumar,S.;Konno,C.;Kiso,Y.;Hikino,H.,Structures of cleomiscosins,coumarinolignoids of Cleome viscosa seeds[J].Tetrahedron 1985,41,(1),209-214.
[7]Shimomura,H.;Sashida,Y.;Oohara,M.,Lignans from Machilus thunbergii[J].Phytochemistry 1988,27,(2),634-636.
[8]Bhandari,P.;Pant,P.;Rastogi,R.P.,Aquillochin,a coumarinolignan from Aquilaria agallocha[J].Phytochemistry 1982,21,(8),2147-2149.
[9]Champavier,Y.;Comte,G.;Vercauteren,J.;Allais,D.P.;Chulia,A.J.,Norterpenoid and sesquiterpenoid glucosides from Juniperus phynicea and Galega officinalis[J].Phytochemistry 1999,50,(7),1219-1223.
[10]顾正兵;陈新建;杨根金;李廷钊;刘文庸;张卫东,糙叶败酱活性成分的研究[J].中药材2002,25,(3),178-180.
[11]Takani,M.;Ohya,K.;Takahashi,K.,Studies on constituents of medicinal plants.Ⅹ Ⅻ.constituents of Schizandra nigra Max[J].Chem.Pharm.Bull.1979,27,(6),1422-1425.
[12]Sakurai,N.;Kobayashi,M.;Shigihara,A.;Inoue,T.,Berchemolide,a novel dimeric vanillic acid glucoside from Berchemia racemosa[J].Chem.Pharm.Bull.1992,40,(4),851-853.
[13]Jung,J.H.;Lee,C.O.;Kim,Y.C.;Kang,S.S.,New Bioactive Cerebrosides from Arisaema amurense[J].J.Nat.Prod.1996,59,(3),319-322.
[14]刘文粢;何凤雷:阮子镛;顾熊飞,狼毒大戟的化学成分研究[J].中国中药杂志 2001,26,(3),180-182.
[15]Ito,A.;Chai,H.B.;Kardono,L.B.S.;Setowati,F.M.;Afriastini,J.J.;Riswan,S.;Farnsworth,N.R.;Cordell,G.A.;Pezzuto,J.M.;Swanson,S.M.;Kinghorn,A.D.,Saponins from the bark of Nephelium maingayi[J].J.Nat.Prod.2004,67,(2),201-205.
[16]Abdel-Mogib,M.,A lupane triterpenoid from Maerua oblongifolia[J].Phytochemistry 1999,51,(3),445-448.
[17]Chaudhuri,S.K.;Fullas,F.;Brown,D.M.;Wani,M,C.;Wall,M.E.;Cai,L.;Mar,W.;Lee,S.K.;Luo,Y.;Zaw,K.;Fong,H.H.S.;Pezzuto,J.M.;Kinghorn,A.D.,Isolation and structural elucidation of pentacyclic triterpenoids from Maprounea africana[J].J.Nat.Prod.1995,58,(1),1-9.
[18]梁爽;陈海生;金永生;金丽;卢嘉;杜景伶,海南狗牙花化学成分研究[J].中国中药杂志2007,32,(13),1296-1299.
[19]Yang,S.M.;Liu,X.K.;Qing,C.;Wu,D.G.;Zhu,D.Y.,Chemical constituents from the roots of Homonoia riparia[J].Acta.Pharm.Sinica 2007,42,(3),285-289.
[20]Kojima,H.;Sato,N.;Hatano,A.;Ogura,H.,Sterol glucosides from Prunella vulgaris[J].Phytochemistry 1990,29,(7),2351-2355.
[21]何际婵;韦松;蓝树彬;许学健,黄杞茎皮化学成分研究[J].中草药 2006,37,(12),1788-1789.
[22]Cheng,M.J.,Chemical and cytotoxic constituents from the stem of Machilus zuihoensis[J].Helv Chim.Acta.2002,85,(7),1909-1914.
[1]中国植物志编委会,中国植物志 第三十七卷[M].北京:科学出版社,1985:223-331.
[2]江苏新医学院,中药大辞典[M].上海:上海科学技术出版社,1975:2705-2708.
[3]韦薇;陈锋;沈爱华,蕨麻的化学成分和药理作用研究进展[J].中国现代医药杂志 2008,10,(1),131-132.
[4]Bilia,A.R.;Palme,E.;Catalano,S.;Flamini,G.;Morelli,I.,New triterpenoid saponins from the roots of Potentilla tormentilla[J].J.Nat.Prod.1994,57,(3),333-338.
[5]薛培凤;乔梁;梁鸿;赵玉英,多裂委陵菜化学成分的研究[J].北京大学学报(医学版) 2004,36,(1),21-23.
[6]刘普;潘勤;张彦文;姚智,委陵菜三萜成分研究[J].中国中药杂志 2006,31,(22),1875-1879.
[7]王庆贺;李志勇;沈阳;林厚文;舒薇;周剑斌,委陵菜三帖类化学成分研究.中国中药杂志2006,31,(17),1434-1436.
[8]Li,P.L.;Zhang,Z.X.;Jia,Z.J.,A new taraxastane-type triterpenoid from Potentilla multicaulis[J].Chin.Chem.Lett.2006,17,(12),1573-1575.
[9]洪霞;蔡光明;韩晋;袁海龙;刘峰群;赵艳玲,新化合物蕨麻苷的结构鉴定[J].解放军药学学报 2004,20,(6),411-414.
[10]薛培凤;路新华;王邠;梁鸿;赵玉英,多裂委陵菜中的四甲基环己烯型单萜苷[J].中国中药杂志 2005,30,(13),983-986.
[11]邹俊利,翻白草的研究进展[J].黑龙江医药科学 2006,29,(4),104-105.
[12]冯卫生;郑晓珂;吉田隆志;奥田拓男,翻白草根中可水解单宁的研究[J].天然产物研究与开发1996,8,(3),27-29.
[13]Xue,P.F.;Liang,H.;Wang,B.;Zhao,Y.Y.,Chemical constituents from Potentilla multifida L.[J].J.Chin.Pharm.Sci.2005,14,(2),86-88.
[14]钟海军;陈纪军;王惠共;罗士德,翻白叶的化学成分[J].中草药 2000,31,(7),488-490.
[15]高雯;沈阳:张红军;汤华;林厚文;邱峰,委陵菜的化学成分研究[J].药学服务与研究2007,7,(4),262-264.
[16]薛培凤;李胜荣;雷静怡;李丽,委陵菜中酸性成分研究[J].内蒙古医学院学报 2007,29,(5),313-315.
[17]Wilkes,S.;Glasl,H.,Isolation,characterization,and systematic significance of 2-pyrone-4,6-dicarboxylic acid in Rosaceae[J].Phytochemistry 2001,58,(3),441-449.
[18]蔡玉华;刘梁;刘长林,三叶委陵菜根化学成分的研究[J].武汉理工大学学报 2005,27,(9),32-33.
[19]张颖;张立木;高允升;齐永秀;李同德;王晓丹,高效液相色谱法测定翻白草中没食子酸含量[J].中国医院药学杂志 2006,26,(3),355-356.
[20]赵国丁;陈建平;袁少飞,蕨麻多糖的含量测定及定性鉴别[J].今日科苑 2007,20,173-174.
[21]皮立;胡凤祖,臧药蕨麻油脂化合物的GC-MS分析[J].中草药2007,38,(11),1625-1627.
[22]Syiem,D.;Syngai,G.;Khup,P.Z.;Khongwir,B.S.;Kharbuli,B.;Kayang,H.,Hypoglycemic effects of Potentilla fulgens L.in normal and alloxan-induced diabetic mice[J].J.Ethnopharmacology 2002,83,55-61.
[23]Zhao,Y.L.;Cai,G.M.;Hong,X.;Shan,L.M.;Xiao,X.H.,Anti-hepatitis B virus activities of triterpenoid saponin compound from Potentilla anserine L.[J].Phytomedicine 2008,15,253-258.
[24]刘梁;韩定献;周军;刘长林;杨占秋,三叶委陵菜根中三萜类化合物抗病毒作用研究[J].时珍国医国药2006,17(8),1484-1485.
[25]Chen,K.L.;Plumb,G.W.;Bennett,R.N.;Bao,Y.P.,Antioxidant activities of extracts from five anti-viral medicinal plants[J].J.Ethnopharmacology 2005,96,201-205.
[26]Gürbüz,I.;Ozkan,A.M.;Yesilada,E.;Kutsal,O.,Anti-ulcerogenic activity of some plants used in folk medicine of P inarbasi(Kayseri,Turkey)[J].J.Ethnopharmacology 2005,101,313-318.
[27]向红,民间草药西南委陵菜抗菌作用的实验[J].贵州师范大学学报(自然科学版)2003,21,(2),55-57.
[28]边可君;徐辉碧;黄开勋;韩定献,三叶委陵菜乙醇提取物镇痛作用的研究[J].江苏临床医学杂志2002,6,(3),200-203.
[29]李贞;张铁权;叶亮;贾玉海,委陵菜对四氯化碳致小鼠肝损伤保护作用[J].辽宁中医杂志2004,31,(5),422-423.
[30]李贞;程留芳;张铁权;李舒;贾上海,委陵菜防治四氯化碳致大鼠肝纤维化实验研究[J].辽宁中医杂志 2007,2007,(34),8.
[31]李灵芝;张丽;龚海英,蕨麻醇提取物的抗缺氧与抗氧化研究[J].中国食品卫生杂志 2005,4,(17),306-308.
[1]王晋;张坚;康胜利,青海产蕨麻营养成分的研究[J].青海医药杂志 1998,28,(2),52-53.
[2]Montaudo,G.;Caccamese,S.,Structure and conformation of chalcone photodimers and related compounds[J].J.Org.Chem.1973,33,(4),710-716.
[3]Ben-Efraim,D.A.;Green,B.S.,The use of mid-points or average NMR chemical shifts in stereochemical assignments[J],Tetrahedron 1974,30,2357-2364.
[4]El-Ansari,M.A.;Nawwar,M.A.;Saleh,N.A.M.,Stachysetin,a diapigenin-7-glucosidep,p'-dihydroxy-truxinate from Stachys aegyptiaca[J].Phytochemistry 1995,40,(5),1543-1548.
[5]Isaza,J.H.;Ito,H.;Yoshida,T.,A flavonol glycoside-lignan ester and accompanying acylated glucosides from Monochaetum multiflorum[J].Phytochemistry 2001,58,(2),321-327.
[6]Daniel,O.,A new general synthesis of 2,2-dialkyl-2,3-dihydro-4H-pyran-4-ones and their application for the in situ preparation of electron-rich dienes in carbonyl-alkyne exchange reactions with acetylenes[J].Helvetica Chimica Acta 1991,74,(1),27-46.
[7]Tsukamoto,S.;Tomise,K.;Aburatani,M.;Onuki,H.;Hirorta,H.;Ishiharajima,E.;Ohta,T.,Isolation of cytochrome P450 inhibitors from strawberry fruit,Fragaria ananassa[J].J.Nat.Prod.2004,67,(11),1839-1841.
[8]Hohmann,J.;Pall,Z.;Gunther,G.;Mathe,I.,Flavonolacyl glycosides of the aerial parts of Erynqium campestre[J].Planta Med.1997,63,(1),96.
[9]Rayyan,S.;Fossen,T.;Andersen,O.M.,Flavone C-glycosides from leaves of Oxalis triangularis[J].J.Agric.Food Chem.2005,53,(26),10057-10060.
[10]Xie,C.;Veitch,N.C.;Houghton,P.J.;Simmonds,M.S.J.,Flavone C-glycosides from Viola yedoensis Makino[J].Chem.Pharm.Bull.2003,51,(10),1204-1207.
[11]Wang,M.;Kikuzaki,H.;Csiszar,K.;Boyd,C.D.;Maunakea,A.;Fong,S.F.T.;Ghai,G.;Rosen,R.T.;Nakatani,N.;Ho,C.T.,Novel trisaccharide fatty acid ester identified from the fruits of Morinda citrifolia(Noni)[J].J.Agric.Food Chem.1999,47,(12),4880-4882.
[12]黄胜阳;石建功;杨永春;胡世林,长苞凹舌兰化学成分研究[J].药学学报 2002,37,(3),199-203.
[13]Topcu,G.;Ay,M.;Bilici,A.;Sarikurkcu,C.;Ulubelen,A.,A new flavone from antioxidant extracts of Pistacia terebinthus[J].Food Chemistry 2007,103,(3),816-822.
[14]Hsu,H.F.;Houng,J.Y.;Chang,C.L.;Wu,C.C.;Chang,F.R.;Wu,Y.C.,Antioxidant activity, cytotoxicity,and DNA information of Glossogyne tenuifolia[J].J.Agric.Food Chem.2005,53,(15),6117-6125.
[15]Errea,M.I.;Matulewicz,M.C.,Cold water-soluble polysaccharides from tetrasporic Pterocladia capillacea[J].Phytochemistry 1994,37,(4),1075-1078.
[16]Bertrand Alluis,O.D.,Quercetin(=2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one)glycosides and sulfates:chemical synthesis,complexation,and antioxidant properties[J].Helvetica Chimica Acta 2001,84,(5),1133-1156.
[17]Kim,H.Y.;Moon,B.H.;Lee,H.J.;Choi,D.H.,Flavonol glycosides from the leaves of Eucommia ulmoides O.with glycation inhibitory activity[J].Journal of Ethnopharmacology 2004,93,(2-3),227-230.
[18]Zou,Y.;Kim,A.R.;Kim,J.E.;Choi,J.S.;Chung,H.Y.,Peroxynitrite scavenging activity of sinapic acid(3,5-dimethoxy-4-hydroxycinnamic acid) isolated from Brassica juncea[J].J.Agric.Food Chem.2002,50,(21),5884-5890.
[19]Merfort,I.;Wendisch,D.,Flavonoid glucuronides from the flowers of Arnica montana[J].Planta Med.1988,54,(3),247-250.
[20]吴海峰:潘莉;丁立生;张晓峰,臧药五脉绿绒蒿的化学成分研究[J].天然产物研究与开发 2007,19,811-813.
[21]顾正兵;陈新建;杨根金;李廷钊;刘文庸;张卫东,糙叶败酱活性成分的研究[J].中药材2002,25,(3),178-180.
[22]李占林;李丹毅;李铣;李宁;孟大利,文冠果果壳中一个新生物碱[J].药学学报2006,42,(12),1197-1200.
[23]Kimura,J.;Maki,N.,New loliolide derivatives from the brown alga Undaria pinnatifida[J].J.Nat.Prod.2002,65,(1),57-58.
[24]Champavier,Y.;Comte,G.;Vercauteren,J.;Allais,D.P.;Chulia,A.J.,Norterpenoid and sesquiterpenoid glucosides from Juniperus phynicea and Galega officinalis[J].Phytochemistry 1999,50,(7),1219-1223.
[25]Yan,X.H.;Guo,Y.W.,Two new ellagic acid glycosides from leaves of diplopanax stachyanthus[J].J.Asian Nat.Prod.Res.2004,6,(4),271-276.
[26]Khallouki,F.;Haubner,R.;Hull,W.E.;Erben,G.:Spiegelhalder,B.;Bartsch,H.;Owen,R.W.,Isolation,purification and identification of ellagic acid derivatives,catechins,and procyanidins from the root bark of Anisophyllea dichostyla R.[J],Br.Food and Chemical Toxicology 2007,45,(3),472-485.
[27]石心红;杜晓犁;孔令义,准噶尔大戟根化学成分的研究[J].中国中药杂志 2006,31,(18),1503-1506.
[28]Baderschneider,B.;Winterhalter,P.,Isolation and Characterization of Novel benzoates,cinnamates,flavonoids,and lignans from riesling wine and screening for antioxidant activity[J].J.Agric.Food Chem.2001,49,(6),2788-2798.
[29]Perry,N.B.;Benn,M.H.;Foster,L.M.;Routledge,A.;Weavers,R.T.,The glycosidic precursor of(Z)-5-ethylidene-2(5H)-furanone in Halocarpus biformis juvenile foliage[J],Phytochemistry 1996,42,(2),453-459.
[30]Li,W.-W.;Barz,W.,Structure and accumulation of phenolics in elicited Echinacea purpurea Cell Cultures[J].Planta Medica 2005,(3),248-254.
[31]邱鹰昆;窦德强;裴玉萍;吉川雅之;松田久司;陈英杰,仙人掌的化学成分研究[J].中国药科大学学报 2005,36,(3),213-215.
[32]H.,T.;D.,T.;T.,H.;K.,N.,Stable isotope-labeling studies on the oxidative coupling of caffeic acid via o-quinone[J].Biosci.Biotech.Biochem.2001,65,(12),2613-2621.
[33]张悦;阮汉利;张勇慧;皮惠芳;吴继洲,鄂西大蓟化学成分的研究[J].医药导报 2007,26,(12),1425-1426.
[34]王伟;赵庆春;安晔;吴立军,中药蜂房的化学成分研究[J].中国药物化学杂志 2008,18,(1),54-55.
[35]李药兰;苏妙贤;岑颖洲;叶文才,小紫金牛的化学成分研究[J].中药材 2006,29,(4),331-333.
[36]Karonen,M.;Hamalainen,M.;Nieminen,R.;Klika,K.D.;Loponen,J.;Ovcharenko,V.V.;Moilanen,E.;Pihlaja,K.,Phenolic extractives from the bark of Pinus sylvestris L.and their effects on inflammatory mediators nitric oxide and prostaglandin E2[J].J.Agric.Food Chem.2004,52,(25),7532-7540.
[37]孙东东;李祥;陈建伟;何立巍,板蓝根醇提部位化学成分研究[J].中国药房 2007,18,(30),2325-2326.
[38] 李云森;罗士德;张勉;陈纪军;王峥涛,棉毛橐吴的化学成分[J].中国中药杂志 2001,26,(12),835-837.
[39]Nakatani,N.;Kayano,S.;Kikuzaki,H.;Sumino,K.;Katagiri,K.;Mitani,T.,Identification,quantitative determination,and antioxidative activities of chlorogenic acid isomers in prune (Prunus domestica L.)[J].J.Agric.Food Chem.2000,48,(11),5512-5516.
[40]丁丽丽;王顺春;王峥涛,猫人参化学成分的研究[J].中国中药杂志 2007,32,(18),1893-1895.
[41]袁干军;杜方麓,硕苞蔷薇果的化学成分研究[J].中药材 2000,23,(8),454-456.
[42]赵爱华;赵勤实;彭丽艳;孙汉董,鬼针草中一个新的查耳酮苷[J].云南植物研究 2004,26,(1),121-126.
[43]Chen,P.;Tucker,W.;Dauterman,W.,Structure of biologically produced malathion monoacid[J].J.Agric.Food Chem.1969,17,(1),86-90.
[44]沈德凤;杨波;付红伟,翻白草中熊果酸的含量测定[J].中国野生植物资源 2002,21,(4),55-56.
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |