Pyrrole alkaloids from Bolbostemma Paniculatum

Three pyrrole alkaloids were isolated from Bolbostemma paniculatum. Their structures were elucidated as 4-(2-formyl-5-methoxymethylpyrrol-1-yl)butyric acid methyl ester (1), 2-(2-formyl-5-methoxymethylpyrrol-1-yl)-3-phenylpropionic acid methyl ester (2) and α-methyl pyrrole ketone (3) by spectroscopic techniques. Among them, 1 and 2 are new compounds.     

A new cucurbitacin from Bolbostemma paniculatum Franguent

A new cucurbitacin with an unusual ring A, isocucurbitacin D 25-O-acetate (1), was isolated from Bolbostemma paniculatum Franguent together with one known compound, cucurbitacin E (2). The structure of new compound was established by spectroscopic methods.     

A new cucurbitacin from Bolbostemma paniculatum Franguent

A new cucurbitacin with an unusual ring A, isocucurbitacin D 25-O-acetate (1), was isolated from Bolbostemma paniculatum Franguent together with one known compound, cucurbitacin E (2). The structure of new compound was established by spectroscopic methods.     

New triterpenoid saponins from bulbs of Bolbostemma paniculatum

Nine new triterpenoid saponins were isolated from the bulbs of Bolbostemma paniculatum (Maxim.) Franquet (Cucurbitaceae): 7beta,18,20,26-tetrahydroxy-(20S)-dammar-24 E-en-3-O-alpha-L-(3-acetyl)arabinopyranosyl-(1-->2)-beta-D-glucopyranoside, 7beta,18,20,26-tetrahydroxy-(20S)-dammar-24E-en-3-O-alpha-L-(4-acetyl)arabinopyranosyl-(1-->2)-beta-D-glucopyranoside, 7beta,18,20,26-tetrahydroxy-(20S)-dammar-24E-en-3-O-alpha-L-arabinopyranosyl-(1-->2)-beta-D-(6-acetyl)glucopyranoside, 7beta,20,26-trihydroxy-(20S)-dammar-24E-en-3-O-alpha-L-arabinopyranosyl-(1-->2)-beta-D-glucopyranoside, 7beta,20,26-trihydroxy-(20S)-dammar-24E-en-3-O-alpha-L-(3-acetyl)arabinopyranosyl-(1-->2)-beta-D-glucopyranoside, 7beta,20,26-trihydroxy-(20S)-dammar-24E-en-3-O-alpha-L-(4-acetyl)arabinopyranosyl-(1-->2)-beta-D-glucopyranoside, 7beta,20,26-trihydroxy-8-formyl-(20S)-dammar-24E-en-3-O-alpha-L-(3-acetyl)arabinopyranosyl-(1-->2)-beta-D-glucopyranoside, 7beta,20,26-trihydroxy-8-formyl-(20S)-dammar-24E-en-3- O-alpha-L-(4-acetyl)arabinopyranosyl-(1-->2)-beta-D-glucopyranoside and 6'-O-palmitoyltubeimoside I. In addition, four known triterpenoid saponins: tubeimoside I, tubeimoside II, tubeimoside III and tubeimoside IV were isolated. The structures of the above compounds were elucidated based on spectroscopic studies, and the configuration of C-20 of tubeimoside IV was revised as S rather than R as reported in previous literature. The compounds were tested for their antiviral activity     

土贝母苷甲和苷乙的抗肿瘤作用

土贝母[Bolbostemma paniculatum(Maxim)Franquet(Cucurbitaceae)]是一种传统中药。土贝母苷甲和苷乙都是从土贝母中分离、纯化出来的抗肿瘤活性成分，属齐墩果烷型三萜皂苷，苷甲和苷乙在结构上的惟一区别是苷乙16位碳上的羟基。苷甲和苷乙的构效关系研究表明，苷乙的抗肿瘤活性较苷甲更强，毒性更低。苷甲和苷乙都能诱导细胞周期阻滞和细胞凋亡。     

中药土贝母研究进展

目的介绍土贝母研究的新进展 ,并对其开发前景进行预测。方法通过查阅近年来国内外有关的资料 ,对土贝母化学成分、药理作用、毒理研究及临床应用等进行综述。结果与结论土贝母有抗肿瘤、杀精子、抗病毒等多种药理活性 ,可望开发成抗肿瘤、抗病毒及避孕等方面的新药     

Solubilizing effect and inclusion reaction of cyclic bisdesmosides from tubers of Bolbostemma paniculatum

Tubeimosides I, II and III (cyclic bisdesmosides) have been isolated from Chinese cucurbitaceous crude drug Tu-bei-mu, a tuber of Bolbostemma paniculatum (Maxim.) Franquet. Solubilizing effects of these cyclic bisdesmosides on water insoluble or less-soluble compounds were examined. It was revealed that cyclic bisdesmosides were effective on increasing the solubility of Yellow OB, dl-alpha-tocopherol and saponin A from Sapindus mukurossi. The critical micell concentration (cmc) and association number as well as diameter of micell of tubeimoside I in water were also measured. The interaction of tubeimoside I with 1-anilino-8-naphthalene-sulfonate (ANS) in aqueous solution was investigated photometrically. It was observed that tubeimoside I strongly enhanced the intensity of fluorescence of ANS, suggesting the significant formation of inclusion complex.     

中药土贝母中环形双糖链皂苷活性成分的分离和鉴定

目的:研究中药土贝母中的环形双糖链皂苷活性成分。方法:采用稻瘟霉模型生物活性追踪方法,应用多种色谱技术进行分离,根据波谱解析和化学手段鉴定其结构。结果:分离并鉴定了4个具有诱导稻瘟霉菌丝变形活性的环形双糖链皂苷:tubeimosideⅠ(1),tubeimosideⅡ(2),tubeimosideⅢ(3)和tubeimosideⅤ(4)。结论:化合物(4)为一种新的环形双糖链皂苷,是第4个从天然界获得的该类型皂苷,且对K-562和BEL-7402肿瘤细胞显示显著的细胞毒性,对1%兔红细胞悬液有较强溶血作用。     

土贝母化学成分的分离与鉴定

目的研究中药土贝母的化学成分.方法用硅胶、Sephadex LH-20柱色谱法进行分离纯化,通过理化性质及光谱数据,结合化学反应确定化合物的结构.结果分离得到7个化合物,分别鉴定为β-谷甾醇(Ⅰ)、胡萝卜苷(Ⅱ)、胡萝卜苷棕榈酸酯(Ⅲ)、β-谷甾醇棕榈酸酯(Ⅳ)、5-羟甲基糠醛(Ⅴ)、麦芽酚(Ⅵ)、正丁基-β-D-吡喃果糖苷(Ⅶ).结论除化合物Ⅵ外,其他化合物均为首次从该植物中分离得到.     

土贝母皂苷对人低分化上皮样鼻咽癌细胞(CNE-2Z)微管的作用

目的：探讨土贝母皂苷(皂苷)对人低分化上皮样鼻咽癌细胞株(CNE-2Z)微管的影响：方法：采用细胞免疫荧光法观察皂苷处理的CNE-2Z细胞微管的变化，蛋白免疫印迹法分析皂苷处理的CNE-2Z细胞中聚合和未聚合微管蛋白含量的变化。结果：免疫荧光图像结果表明，皂苷作用的CNE-2Z细胞丧失正常的微管网络，蛋白免疫印迹结果证实皂苷使CNE-2Z细胞未聚合的微管蛋白比例增加，而且这一作用与剂量和时间呈正相关。结论：皂苷能抑制CNE-2Z细胞内微管的聚合，提示皂苷是一种有效的抗微管剂、     

土贝母的化学成分及药理作用研究进展

土贝母中含有皂苷类、有机酸类、甾醇类、生物碱类等化学成分,药理作用为抗病毒、抗癌、抑制免疫、杀精等。通过对土贝母的化学成分及药理作用概况进行综述,以期为该药材的进一步开发研究提供参考。     

土贝母苷甲诱导HeLa细胞周期阻滞和凋亡

目的 :研究土贝母苷甲 (下称苷甲 )抗肿瘤作用的机制 ,探索它对细胞周期和细胞凋亡的影响。方法 :采用MTT法检测苷甲对细胞生长的抑制作用 ;采用流式细胞术 ,光学、荧光和电子显微镜 ,以及DNA琼脂糖凝胶电泳检查和分析苷甲对细胞周期和细胞凋亡的影响 ;采用蛋白免疫印迹法检测凋亡相关基因bcl 2和bax表达的变化。结果 :苷甲对HeLa细胞的生长有强抑制作用 ,其 2 4、4 8和 72h的IC50 值分别为 35 .7,2 3.6 ,17.4 μmol·L-1。在苷甲的作用下 ,细胞周期阻滞在G2 M期 ,细胞在形态学和生物化学上都出现了细胞凋亡的典型证据。蛋白免疫印迹结果揭示bcl 2下调 ,bax过表达。结论 :苷甲诱导的细胞周期阻滞和凋亡在苷甲的抗肿瘤效果中可能起着重要作用 ,而苷甲诱导的细胞凋亡与bcl 2的下调及bax的过表达密切相关。     

Pyrrole 2-carbaldehyde derived alkaloids from the roots of Angelica dahurica

Journal of Natural Medicines - Six new pyrrole 2-carbaldehyde derived alkaloids, dahurines A–F (1–6), along with five known ones (7–11) and butyl 2-pyrrolidone-5-carboxylate (12)...     

土贝母苷甲对小鼠B16黑色素瘤和Lewis肺癌转移的抑制作用

目的:本研究旨在探讨土贝母苷甲对小鼠B16黑色素瘤和Lewis肺癌转移的影响。方法:采用裸BALB/c小鼠B16黑色素瘤实验转移和裸BALB/c小鼠Lewis肺癌自发转移模型研究土贝母苷甲对肿瘤转移的影响;采用免疫组织化学法检测土贝母苷甲对转移相关基因CD44v6、ErbB-2和nm23-H1表达的影响。结果:腹腔注射低于全身中毒水平剂量的土贝母苷甲明显减少接种B16黑色素瘤细胞小鼠的肺重和肺转移灶数量,而对小鼠的健康和活力无明显影响;土贝母苷甲(2、3 mg.kg-1.d-1×14 d)和环磷酰胺(50 mg.kg-1.wk-1×2 d)对B16黑色素瘤细胞肺转移的抑制率分别为68.8%、82.8%和49.1%。土贝母苷甲治疗组小鼠Lewis肺癌原发肿瘤的平均瘤重明显低于对照组(P<0.05)。土贝母苷甲(2、3 mg.kg-1.d-1×14 d)和环磷酰胺(50 mg.kg-1.w-1×2 d)治疗组小鼠的肝转移抑制率分别为46.3%、52.0%和54.7%。土贝母苷甲显著下调促转移基因CD44v6和ErbB-2的表达,上调抑转移基因nm23-H1的表达。结论:土贝母苷甲对小鼠B16黑色素瘤的实验性转移和Lewis肺癌的自发性转移都有显著的抑制作用。土贝母苷甲对肿瘤转移的这种抑制作用与其抑制原发肿瘤生长、下调促转移基因CD44v6和ErbB-2及上调抑转移基因nm23-H1的表达有关,提示土贝母苷甲是一个阻止癌扩散和转移的候补化合物。     

Pyrrole and indole alkaloids from an endophytic Fusarium incarnatum (HKI00504) isolated from the mangrove plant Aegiceras corniculatum

Two new pyrrole alkaloids, N-[4-(2-formyl-5-hydroxymethyl-pyrrol-1-yl)-butyl]-acetamide (1) and N-[5-(2-formyl-5-hydroxymethyl-pyrrol-1-yl)-pentyl]-acetamide (2), and a new indole derivative (3aR,8aR)-3a-acetoxyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indol (3) were isolated, together with ( - )-3a-hydroxyfuroindoline, (3aR,8aS)-1-acetyl-1,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indol-3a-ol, and N-acetyltryptamine A, from an endophytic ascomycetous fungus, Fusarium incarnatum (HKI00504), which was isolated from the mangrove plant Aegiceras corniculatum. The structures of compounds 1-3 were determined on the basis of extensive spectroscopic data analyses.     

Pyrrole and indole alkaloids from an endophytic Fusarium incarnatum (HKI00504) isolated from the mangrove plant Aegiceras corniculatum

Two new pyrrole alkaloids, N-[4-(2-formyl-5-hydroxymethyl-pyrrol-1-yl)-butyl]-acetamide (1) and N-[5-(2-formyl-5-hydroxymethyl-pyrrol-1-yl)-pentyl]-acetamide (2), and a new indole derivative (3aR,8aR)-3a-acetoxyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indol (3) were isolated, together with ( - )-3a-hydroxyfuroindoline, (3aR,8aS)-1-acetyl-1,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indol-3a-ol, and N-acetyltryptamine A, from an endophytic ascomycetous fungus, Fusarium incarnatum (HKI00504), which was isolated from the mangrove plant Aegiceras corniculatum. The structures of compounds 1-3 were determined on the basis of extensive spectroscopic data analyses.     

徐长卿中酚类成分的分离与鉴定

目的研究徐长卿(Cynanchum paniculatum(Bge.)Kitag.)的酚类成分,为其药理活性的研究奠定物质基础。方法通过多种色谱方法进行分离纯化,根据理化性质和1H-NMR、13C-NMR波谱数据分析进行结构鉴定。结果从徐长卿中分离得到14个酚类化合物,分别鉴定为:苯甲酸(benzoic acid,1)、3-甲基苯酚(3-methylphenol,2)、对羟基苯乙酮(p-hydroxyacetophenone,3)、3-羟基苯乙酮(3-hydroxyacetophenone,4)、对甲氧基苯甲酸(p-methoxybenzoic acid,5)、肉桂酸(cinnamic acid,6)、2,4-二羟基苯乙酮(2,4-dihydroxyacetophenone,7)、2,5-二羟基苯乙酮(2,5-dihydroxyacetophenone,8)、罗布麻宁(apocynin,9)、2,5-二羟基-4-甲氧基苯乙酮(2,5-dihydroxy-4-methoxyacetophenone,10)、丁香醛(syringaldehyde,11)、3,5-二甲氧基-4-羟基苯乙酮(4-hydroxy-3,5-dimethoxyacetophenone,12)、3-吲哚甲醛(1H-indole-3-carboxaldehyde,13)和3-甲氧基-4,5-亚甲二氧基-苯乙酮(3-methoxy-4,5-methylenedioxy-acetophenone,14)。结论化合物2、5、12¹4为首次从鹅绒藤属植物中分离得到,化合物1、6、8、9、11为首次从该植物中分离得到。     

Pyrrole carboxamidine tryptase inhibitors from Leptonychia pubescens

The root and stem bark extracts of a Nigerian sample of Leptonychia pubescens Keay (Sterculiaceae) were found to inhibit the serine protease tryptase, a potential therapeutic target for the treatment of asthma and chronic obstructive pulmonary disease (COPD). Bioassay-guided isolation led to the identification of 1-beta-ribofuranosylbrunfelsamidine as the active component with a tryptase IC (50) of 3 microM. Brunfelsamidine was also isolated, but was only weakly active.     

Synthese phenylsubstituierter Pyrrole

Synthesis of Phenylsubstituted Pyrroles Condensation of 2-anilino-2-phenyl-acetophenone with the carbonyl-compounds R¹? CO? CH₂? R², catalized by formic acid leads to 1,2,3-triphenylpyrroles with the substituted groups R¹ and R².