蟛蜞菊化学成分研究

目的研究菊科蟛蜞菊属植物蟛蜞菊的化学成分。方法蟛蜞菊全草粉碎后用95%乙醇提取,提取物分别经过石油醚、乙酸乙酯和正丁醇萃取,石油醚部分采用硅胶柱层析、葡聚糖凝胶、反复重结晶、制备型HPLC等多种技术分离纯化,通过理化性质和波谱数据鉴定所得化合物的化学结构。结果从蟛蜞菊中分离得到12个化合物,分别鉴定为ent-kaura-9(11),16-en-19-oic acid(1),ent-kaura-16-en-19-oic acid(2),15β,16β-epoxy-17-hydroxy-ent-kauran-19-oic acid(3),16α,17-dihydroxy-ent-kauran-19-oic acid(4),16α-hydroxy-ent-kauran-19-oic acid(5),15α-hydroxy-entkaura-16-en-19-oic acid(6),3α-angeloyloxy-9β-hydroxy-ent-kaura-16-en-19-oic acid(7),3α-cinnamoyloxy-9β-hydroxy-entkaura-16-en-19-oic acid(8),3α-cinnamoyloxy-17-hydroxy-ent-kaura-15-en-19-oic acid(9),12α-methoxy-ent-kaura-9(11),16-en-19-oic acid(10),ent-12-oxokaur-9(11),16-en-19-oic acid(11),17-hydroxy-ent-kaura-15-en-19-oic acid(12)。结论化合物3⁹为首次从该植物中分离得到,化合物109为首次从该植物中分离得到,化合物10¹2为首次从该属中分离得到。     

番荔枝果皮弱极性成分研究(Ⅲ)

目的 研究番荔枝Annona squamosa Linn.果皮弱极性成分。方法 番荔枝果皮95%乙醇提取物采用硅胶柱进行分离纯化，根据理化性质及波谱数据鉴定所得化合物的结构。结果 从中分离得到6个化合物，分别鉴定为16α-17-acetoxy-18-nor-ent-kaurane-4β-ol (1)、ent-kaurane-16-en-19-ol (2)、ent-kuarane-15-en-17-al-18-oic acid (3)、ent-kuarane-15-en-17-al-19-oic acid (4)、16α,17-dihydroxy-ent-kaurane-19-oic acid methyl ester (5)、16α-ent-kaurane-17-ol (6)。结论 化合物1为新化合物，化合物3～6均为首次从番荔枝果皮中分离得到。     

番荔枝果皮小极性成分研究

目的:研究番荔枝果皮中的小极性成分。方法:番荔枝果皮95%乙醇提取物的小极性部位经硅胶柱分离,根据化合物理化性质和波谱数据鉴定结构。结果:从番荔枝果皮小极性部位中分离得到8个化合物,分别鉴定为:二十三烷酸(1)、β-谷甾醇(2)、琥珀酸(3)、annosquamosin D(4)、4α-hydroxy-19-nor-(E)-kauran-17-oic acid(5)、(E)-16β,17-dihydroxy-kauran-19-oic acid(6)、(E)-16α,17-dihydroxy-kauran-19-oic acid(7)、16β-hydroxy-17-acetoxy-(E)-kauran-19-oic acid(8)。结论:除化合物6外,其他均为首次从番荔枝果皮中分离得到。     

蜈蚣草二萜类化学成分及其抗炎活性

目的:研究蜈蚣草Pteris vittata的化学成分及其体外抗炎活性。方法:95%乙醇对蜈蚣草进行回流提取,不同极性有机溶剂萃取提取物,萃取物经过色谱柱进行分离纯化,采用NMR进行解析;通过脂多糖诱导RAW264.7细胞炎症模型评价获得的化合物的抗炎活性。结果:从乙酸乙酯部位分离得到6个化合物,分别鉴定为对映-3β-羟基-贝壳杉-16-烯(ent-3β-hydroxy-kaur-16-ene)(1),对映-3β-乙酰氧基-贝壳杉-16-烯(ent-3β-acetoxy-kaur-16-ene)(2),13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-xylopyranosyl)-oxy]ent-kaur-16-en-19-oic acid β-D-glucopyranosyl ester(3),13-[(2-O-α-D-glucopyranosyl-β-D-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid 2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl ester(4),越南巴豆素C(crotonkinin C)(5)和越南巴豆素D(crotonkinin D)(6)。抗炎活性实验表明,化合物1和2具有较强的抑制NO产生作用,IC_(50)值分别为9.5、8.3μmol·L~(-1)。结论:所有化合物均首次从该植物中分离得到;首次研究发现化合物1和2具有较强的抗炎活性。     

圆滑番荔枝的化学成分研究

 目的从圆滑番荔枝树皮提取分离活性化合物。方法95%乙醇提取、溶剂萃取、硅胶柱色谱、重结晶等，根据IR,MS,NMR等光谱技术和化学方法鉴定化合物的结构。结果分离到5个化合物，分别鉴定为ent-16α-hydro-kauran-17-oic acid (Ⅰ)、annonebinide B(ent-16α-hydro-kauran-19-oic acid-17-yl ent-16β-kauran-17-oate)(Ⅱ) 、ent-kauran-16α,17-diol(Ⅲ)、4α-hydroxy-19-nor-ent-kauran-17-oic acid (Ⅳ) 、liriodenine(Ⅴ)。结论Ⅱ为新化合物。     

剑叶凤尾蕨化学成分及其细胞毒活性研究

采用95%乙醇提取药材,提取液回收至无醇味后依次过聚酰胺树脂、MCI树脂、中压制备液相色谱和制备型高效液相色谱,从剑叶凤尾蕨全草中分离得到8个二萜类化合物和2个倍半萜类化合物。质谱(ESI-MS)数据和核磁共振(NMR)数据与文献数据对比鉴定分离得到的化合物分别为ent-3β-hydroxy-kaur-16-en-19-al(1),4-epi-kaurenic acid(2),mitrekaurenone(3),7β,16α,17-trihydroxy-ent-kauran-19-oic acid(4),crotonkinin E(5),crotonkinin F(6),pterisolic acid A(7),pterisolic acid C(8),(2R)-pterosin P(9)和dehydropterosin B(10)。化合物1~6首次从凤尾蕨属中分离得到,化合物7~10首次从剑叶凤尾蕨中获得。细胞毒活性测试表明化合物5~8具有一定的抑制人结肠癌细胞HCT-116、肝癌细胞Hep G2和人胃癌细胞BGC-823的活性。     

亮叶围涎树根的化学成分及其肿瘤细胞毒活性研究

目的:研究亮叶围涎树根的化学成分及其抗肿瘤活性.方法:应用硅胶,Sephadex LH-20,HPLC等各种色谱技术进行分离纯化,用NMR等谱学方法分析确定化合物结构.采用MTT法对分离得到的化合物进行抗肿瘤活性评价.结果:从亮叶围涎树根的95％乙醇提取物的乙酸乙酯萃取物中分离得到6个化合物,分别鉴定为:julibroside A2(1),3-[(2-acetamido-2-deoxyβ-D-glucopyranosyl)oxy]-16α-bydroxyolean-12-en-28-oic acid(2),没食子酸(3),没食子酸乙酯(4),(+)-儿茶素(5),(-)-没食子儿茶素没食子酸酯(6).化合物2对人源肿瘤细胞A2780具有较强的细胞毒活性(IC501.72 μmol·L-1).结论:化合物1～6均为首次从该植物中分离获得.化合物2对人源肿瘤细胞A2780具有明显的细胞毒活性.     

刺齿凤尾蕨化学成分及其体外抗肿瘤活性研究

乙醇提取刺齿凤尾蕨药材,提取物依次经过有机溶剂萃取,聚酰胺柱色谱、葡聚糖凝胶柱色谱和制备型HPLC色谱分离得到10个对映-贝壳杉烷型二萜类化合物。采用核磁共振(NMR)和质谱(ESI-MS)技术鉴定获得的化合物分别为geopyxin B(1),geopyxin E(2),ent-11α-hydroxy-18-acetoxykaur-16-ene(3),ent-14β-hydroxy-18-acetoxykaur-16-ene(4),neolaxiflorin L(5),ent-3β,19-dihydroxy-kaur-16-ene(6),ent-3β-hydroxy-kaur-16-ene(7),7β,17-dihydroxy-16α-ent-kauran-19-oic acid 19-O-β-Dglucopyranoside ester(8),crotonkinin C(9)和crotonkinin C(10)。化合物1~10均为首次从刺齿凤尾蕨中获得。体外活性研究表明,化合物1和2对Bel-7402细胞具有抑制作用,IC50分别为7.50,10.60μmol·L-1;化合物1和2对Hep G2细胞具有抑制作用,IC50分别为6.68,11.80μmol·L-1。     

三裂蟛蜞菊花的化学成分研究

目的:研究三裂蟛蜞菊花化学成分。方法:利用硅胶柱层析,通过理化性质和波谱学数据鉴定化合物的结构。结果:分离并鉴定了5个化合物:Grandiflorenic acid(4α-kaur-9(11),16-dien-19-oic acid,Ⅰ),6-异丁酰基-三叶拉色芹内酯(trilobolide-6-O-isobutyrate,Ⅱ),1β-Acetoxy-4α,9α-dihydroxy-6β-isobutyroxy-prostatolide(Ⅲ),对映16β,17-二羟基贝壳杉烷-19-羧酸(16β,17-dihydroxy-ent-kauran-19-oic acid,Ⅳ),β-胡萝卜苷(β-daucosterol,Ⅴ)。     

滨藜叶分药花化学成分研究

对唇形科分药花属植物滨藜叶分药花Perovskia atriplicifolia Benth.的干燥全草90%乙醇提取物的乙酸乙酯部分进行化学成分研究,从中分离得到15个化合物。经通过波谱数据分析及与文献对照,该15个化合物的结构分别鉴定为:蓟黄素(cirsimaritin,1),鼠尾草素(salvigenin,2),丁香醛(syringaldehyde,3),咖啡酸乙烯酯(vinyl caffeate,4),2α,3α-dihydroxyolean-12-en-28-oic acid(5),2α,3α-dihydroxyurs-12-en-28-oic acid(6),niga-ichigoside F1(2α,3β,19α,23-tetrahydroxyurs-12-en-28-oic acidO-β-D-glucopyranoside,7),绢毛榄仁苷(sericoside,8),4-epi-niga-ichigoside F1(2α,3β,19α,24-tetrahydroxyurs-12-en-28-oic acid O-β-D-glucopyranoside,9),瓜子金皂苷丁(2α,3β,24-trihydroxyolean-12-en-28-oic acid O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside,10),夏枯草苷(pruvuloside A,11),2α,3β,23-trihydroxyolean-12-en-28-oic acid O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside(12),迷迭香酸甲酯(rosmarinic acid methyl ester,13),β-谷甾醇(β-sitosterol,14),胡萝卜苷(daucosterol,15)。化合物1~13为首次从该属植物中分离得到。所有化合物均为首次从该种植物中分离得到。     

New ent-kaurane diterpenoids with anti-platelet aggregation activity from Annona squamosa

A phytochemical investigation on the stems of Annona squamosa led to the isolation of six new ent-kaurane diterpenoids, annomosin A (16beta-hydroxy-19-al-ent-kauran-17-yl 16beta-hydro-19-al-ent-kauran-17-oate) (1), annosquamosin C (16alpha-hydro-17-hydroxy-19-nor-ent-kauran-4alpha-ol) (2), annosquamosin D (16beta-acetoxy-17-hydroxy-19-nor-ent-kauran-4alpha-ol) (3), annosquamosin E (16beta-hydroxy-17-acetoxy-19-nor-ent-kauran-4alpha-formate) (4), annosquamosin F (16beta-hydroxy-17-acetoxy-18-nor-ent-kauran-4beta-hydroperoxide) (5), and annosquamosin G (16beta,17-dihydroxy-18-nor-ent-kauran-4beta-hydroperoxide) (6), along with 14 known ent-kaurane diterpenoids. The structures of 1-6 were elucidated by spectroscopic data interpretation. Compound 1 is the first dimeric ent-kaurane derivative to have been reported from a plant in the family Annonaceae. Certain useful NMR data were generalized to determine the stereochemistry of C-16 among the ent-kaurane diterpenoids investigated. ent-Kaur-16-en-19-oic acid (9) and 16alpha-hydro-19-al-ent-kauran-17-oic acid (17) showed complete inhibitory effects on rabbit platelet aggregation at 200 microM.     

Microbial transformations of isosteviol

Microbial transformations of the tetracyclic diterpenoid isosteviol (ent-16-ketobeyeran-19-oic acid) (2) have revealed that isosteviol is metabolized by Cunninghamella bainieri, Actinoplanes sp., Mucor recurvatus, and Cunninghamella blakesleeana to yield five new metabolites, ent-11alpha,12alpha-dihydroxy-16-ketobeyeran-19-oic acid (5), ent-11alpha,12alpha,17-trihydroxy-16-ketobeyeran-19-oic acid (6), ent-12alpha,15alpha-dihydroxy-16-ketobeyeran-19-oic acid (7), ent-7alpha,15alpha-dihydroxy-16- ketobeyeran-19-oic acid (8), and ent-9alpha-hydroxy-16-ketobeyeran-19-oic acid (9), together with three known metabolites, ent-7alpha-hydroxy-16-ketobeyeran-19-oic acid (3), ent-7beta-hydroxy-16-ketobeyeran-19-oic acid (4), and ent-12alpha-hydroxy-16-ketobeyeran-19-oic acid (10). The structures of these metabolites were established on the basis of HRFABMS and 1D and 2D NMR spectral data. In addition, metabolites 3-10 were tested for antihypertensive activity and were found to be less active than the parent compound 2.     

毛梗豨莶化学成分的研究Ⅱ

 目的：对毛梗-莶(Siegesbeckiaglabrescens)的化学成分进行分离、鉴定研究。方法：采用各种层析色谱技术进行分离。从毛梗莶中分离到了5个化合物,用IR,MS,₁H-NMR,₁₃C-NMR和₂D-NMR光谱鉴定化合物。结果：经光谱鉴定化合物为(Ⅰ)对映16β,17二羟基-贝壳杉-19-羧酸(ent-16β,17-dihydroxykauran-19-oicacid),化合物(Ⅱ)为单棕榈酸甘油脂(glyceralmon/opalmitate),化合物(Ⅲ)为对映 贝壳杉-16β,17,18-三醇(ent-kauran-16β,17,18-triol),化合物(Ⅳ)为18-羟基-贝壳杉-16-烯-19-羧酸(18-hydroxy-hauran-16-en-19-oicacid),化合物(Ⅴ)为胡萝卜苷(Daucosterol)。结论：化合物(Ⅰ)、(Ⅱ)、(Ⅲ)为首次从该植物中得到。     

红大戟中的非蒽醌类化学成分

运用硅胶、Sephadex LH-20柱色谱和HPLC制备色谱等方法进行分离和纯化,从茜草科红芽大戟属植物红大戟根的乙醇提取物中首次分离得到21个非蒽醌类成分;通过NMR和MS等波谱数据鉴定了化合物的结构,包括10个三萜:乌苏酸(1),齐墩果酸(2),3β,19α-二羟基-2-氧-乌苏-12-烯-28-酸(3),坡模酸(4),马斯里酸(5),3β,19α,24-三羟基-乌苏-12-烯-28-酸(6),委陵菜酸(7),救必应酸-3,23-缩丙酮(8),2α,3β,19α,23-四羟基-齐墩果-12-烯-28-酸(9),2α,3β,19α,23-四羟基-乌苏-12-烯-28-酸(10);4个豆甾酮:(24R)-24-豆甾-4,22-二烯-3-酮(11),(24R)-24-豆甾-4-烯-3-酮(12),(24R)-24-豆甾-3β-羟基-5,22-二烯-7-酮(13),(24R)-24-豆甾-3β-羟基-5-烯-7-酮(14);2个木脂素:桉脂素(15),刺五加酮(16);1个香豆素:8-甲氧基异欧前胡素(17);4个简单芳香类化合物:5-羟甲基呋喃醛(18),3-羟基-4-甲氧基苯甲酸(19),苯甲酸(20),2-羟基-5-甲氧基-苯丙烯醛(21)。在肿瘤细胞毒(MTT法,HCT-8,Bel7402,BGC-823,A549和A2780),神经细胞保护(去血清和谷氨酸损伤模型),抗氧化(Fe2+-Cys诱导大鼠肝微粒体丙二醛生成模型),抗炎(小鼠腹腔巨噬细胞分泌NO模型),抗HIV(VS-VG/HIV-luc模型)和抗糖尿病(PTP1B酶抑制模型)药理模型上筛选结果显示,在1.0×10-5mol.L-1浓度下,这些化合物均未表现出活性。     

信宜润楠的化学成分研究

通过萃取、正相硅胶、Sephadex LH-20、闪式柱色谱以及反相HPLC柱色谱等多种分离方法相结合,从信宜润楠乙醇提物中首次分离得到21个化合物;借助红外、质谱和核磁共振等波谱学分析方法鉴定了它们的结构,其中包括8个丁内酯类(1～8),8个木脂素类(9～16)和5个萜类化合物(17～21),化合物16是降七碳木脂烷类新天然产物。经体外活性筛选发现化合物5对胃癌(BGC-823)和卵巢癌(A2780)人肿瘤细胞株有选择性抑制活性,IC50分别为0.13×10-6,2.66×10-6mol.L-1;在1×10-5mol.L-1时,化合物8和9具有明显抑制PAF刺激大鼠多形核白细胞β-葡萄糖苷酸酶释放作用,抑制率分别为60.0%,54.2%。     

Transformation of steviol-16alpha,17-epoxide by Streptomyces griseus and Cunninghamella bainieri

Eight new ent-beyerane metabolites, 5-8, 12, and 14-16, and four new ent-kaurane metabolites, 3, 10, 11, and 13, together with two known metabolites, 4 and 9, were isolated from the microbial transformations of steviol-16alpha,17-epoxide using Streptomyces griseus ATCC 10137 and Cunninghamella bainieri ATCC 9244. The structures of the metabolites were characterized by IR, HRFABMS, and 1D and 2D NMR data. In addition, a GRE (glucocorticoid response element)-mediated luciferase reporter assay was used to initially screen for the biological activity of the 11 metabolites and stevioside. Steviol (1), steviol-16alpha,17-epoxide (2), ent-11alpha,13,16alpha,17-tetrahydroxykauran-19-oic acid (3), ent-17-hydroxy-16-ketobeyeran-19-oic acid (4), ent-9alpha,13-dihydroxy-16beta,17-epoxykauran-19-oic acid (10), ent-9alpha,17-dihydroxy-16-ketobeyeran-19-oic acid (12), ent-1beta,17-dihydroxy-16-ketobeyeran-19-oic acid (14), and stevioside showed significant effects; in particular, stevioside showed almost equal potency as dexamethasone.     

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??OBJECTIVE To study the chemical constituents from the roots of Rubus parvifolius. METHODS Various chromatographic techniques such as silica gel, Sephadex LH-20, and prep-HPLC column chromatography were used. RESULTS Nineteen compounds, including 12 triterpenoids were isolated from the roots of Rubus parvifolius. Based on the analysis of their spectroscopic data, the structures of these 19 compounds were identified as p-hydroxybenzoic acid(1), 4-hydroxy-3,5-dimethoxybenzoic acid(2), 3-methoxy-4-hydroxybenzoic acid(3), ??-sitosterol(4), oleanolic acid(5), ursolic acid(6), 2-oxopomolic acid(7), pomolic acid(8), p-hydroxyphenylethyl alcohol(9), psiguanin A(10), 2??-hydroxyursolic acid(11), tormentic acid(12), 2??,3??,19??,23-tetrahydroxyurs-12-en-28-oic acid(13), L-epicatechin(14), 2??,3??,19??,24- tetrahydroxyolean-12-en-28-oic acid(15), 2??,3??,19??,24-tetrahydroxyurs-12-en-28-oic acid(16), 2??,3??,19??-trihydroxyolean-12-en-23,28-dioic acid(17), suavissimoside R₁ (18), and daucosterol(19), respectively. CONCLUSION Compounds 1-3, 5, 7-10, 12, and 15-17 are isolated from the roots of R. parvifolius for the first time. Compounds 7 and 9 are isolated from the genus Rubus L. for the first time. Compounds 10 and 15-17 are isolated from the family Rosaceae for the first time.     

半边旗提取物及化学成分抗肿瘤作用的研究

目的：研究半边旗提取物及其单体化合物的抗肿瘤作用。方法：采用MTT法对半边旗提取物及其单体化合物进行抗肿瘤活性测试。结果：半边旗乙酸乙酯萃取物、正丁醇萃取物以及单体化合物11-βhydroxy-15-oxo-ent-kaur-16-en-19-oic acid 19--βD-glucoside（化合物Ⅰ）和11-βhydroxy-15-oxo-ent-kaur-16-en-19-oic acid（化合物Ⅱ,即5F）均可抑制两种肿瘤细胞HepGⅡ和NCI-H460的生长,且它们对两种肿瘤细胞的抑制作用呈剂量依赖关系和时间关系,相同浓度化合物Ⅱ对两种肿瘤细胞增殖的抑制率明显高于化合物Ⅰ。结论：半边旗乙酸乙酯萃取物、正丁醇萃取物是半边旗抗肿瘤的有效部位;半边旗中贝壳杉烷类化合物的抗肿瘤活性不仅与α,β-亚甲基环戊酮结构有关,还与是否连有糖基有关。     

Bioactive ent-clerodane diterpenoids from the aerial parts of Baccharis gaudichaudiana

Three new ent-clerodane diterpenes (1-3) were isolated from the aerial parts of Baccharis gaudichaudiana, and their structures were elucidated as 15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid (1), 13-epi-15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid (2), and 7-oxo-16-hydroxy-ent-clerod-3-en-15-oic acid methyl ester-18,19-olide (3), on the basis of spectroscopic data analysis. A known compound, 7-oxo-ent-clerod-3-en-15,16:18,19-diolide, was also identified. Compounds 1 and 2 showed enhancing activity of nerve growth factor (NGF)-induced neurite outgrowth in PC 12D cells.