紫玉盘种子中的番荔枝内酯成分研究I. 紫玉盘素(Microcarpacin)的分离及结构鉴定

从紫玉盘(Uvaria microcarpa Champ. ex Benth)种子中首次分离得到一个新的邻双四氢呋喃环番荔枝内酯(Annonaceousacetogenin)化合物-紫玉盘素(Microcarpacin)。同时首次以纯化合物形式分离得到两个已知的番荔枝内酯Narumicins I和Narumicins II.     

紫玉盘种子中的番荔枝内酯成分研究 Ⅰ.紫玉盘素(Microcarpacin)的分离及结构鉴定

从紫玉盘(Uvaria microcarpa Champ.ex Benth)种子中首次分离得到一个新的邻双四氢呋喃环番荔枝内酯(Annonaceous acetogenin)化合物—紫玉盘素(Microcarpacin).同时首次以纯化合物形式分离得到两个已知的番荔枝内酯NarumicinsⅠ和Narumicins Ⅱ.     

紫玉盘素B的分离与鉴定

从紫玉盘(Uvaria microcarpa)种子中首次分离得到二个白色蜡状固体, 经光谱分析鉴定: 一个为新的番荔枝内酯-紫玉盘素B(Microcarpacin B), 一个为已知的番荔枝内酯-Rollinicin。     

阿蒂莫耶化学成分的研究及阿蒂莫耶素B的分离和结构

从阿蒂莫耶(Annona atemoya Hort)种子中, 首次分离到四个白色蜡状固体,经光谱分析, 分别为新的番荔枝内酯(Annonaceous acetogenin)-阿蒂莫耶素B(Atemoyacin B)和三个已知的番荔枝内酯Bullatacin, Molvizarin和Rollinicin。     

牛心果化学成分的研究

从牛心果(Annona glabra Linn)树皮中, 分离到三个白色蜡状固体, 经光谱分析, 它们分别为 强抗肿瘤活性番荔枝内酯(annonaceous acetogenin) 化合物-----annonacin,corossolone和solamin.     

阿蒂莫耶番荔枝内酯的研究

本文首次报道从阿蒂莫耶番荔枝(Annona atemoya Hort)种子中分离到七个白色蜡状固体, 经光谱鉴定, 它们分别为已知的抗肿瘤活性番荔枝内酯(annonaceous acetogenin)-Asimicin, Motrilin, Isodesacetyluvaricin,Cherimolin-1, Almunequin, Squamocin-K和Neoannonin。     

番荔枝内酯————明日抗癌之星

本文介绍一类近年来被发现于番荔枝科(Annonaceae)植物中的强抗肿瘤活性化合物----番荔枝内酯(annonaceousacetogenin) , 从这类化合物的结构特点, 生理活性, 生源假说, 化学合成等几个方面综述了在该领域的氧基状况 .     

阿蒂莫耶素D的分离与结构

从阿蒂莫耶(Annonaatemoya(I)Hort)种子中分离到一个新的邻双四氢呋喃环型番荔枝内酯(Annonaceousacetogenin)-阿蒂莫耶素D(AtemoyacinD),同时分离到四个已知番荔枝内酯neo-annoninB、neodesacetyluvaricin、parviflorin和annonacin。     

海南暗罗根中一个新的克罗烷型二萜

采用硅胶柱层析,制备薄层层析等色谱方法,从海南暗罗根中分离得到8个二萜类化合物,分别鉴定为polyalimide A(1),kolavenic acid(2),2-oxo-kolavenic acid(3),2-oxo-14,15-bisnor-3,11E-kolavadien-13-one(4),3,4-dihydroxyclerodan-13E-en-15-oic acid(5),longimide B(6),16-oxocleroda-3,13E-dien-15-oic acid(7),solidagonal acidmethyl ester(8).其中化合物1为新化合物,化合物5首次从番荔枝科分离得到,所有化合物首次从该植物中分离得到.化合物2和3对人肿瘤细胞SPCA-1,SGC-7901和K-562显示微弱的细胞毒性.     

阿蒂莫耶根番荔枝内酯的研究

从阿蒂莫耶(AnnonaatemoyaHort)根中分离到一个新的含有四个羟基的邻双四氢呋喃环型番荔枝内酯(Annonaceousacetogenin)-阿蒂莫耶素C(AtemoyacinC),同时分离到五个已知番荔枝内酯isocherimolin-1、bullatacin、rollinicin、almunequin和atemoyacinB。     

New cytotoxic annonaceous acetogenin mimetics having a nitrogen-heterocyclic terminal and their application to cell imaging

A terminal unsaturated lactone or its equivalent is commonly believed to be essential for the cytotoxicity of natural annonaceous acetogenins and their artificial mimetics. In this work, we discovered a series of new cytotoxic ethylene glycol ether-containing mimetics, in which a variety of simple aliphatic nitrogen-heterocycles were introduced to replace the lactone terminal of AA005 (1), a representative bioactive polyether mimic identified from our previous research, for the first time. Among these, mimic 4 bearing a terminal piperazine was found to be the most potent compound against the proliferation of three cancer cells. Based on our new findings, a fluorescent probe 7 was also developed and successfully applied to the imaging of cancer cells. This work provides a new strategy for developing simpler cytotoxic mimetics of natural annonaceous acetogenins and molecular tools for biological imaging.     

Chemical Biology Studies on Molecular Diversity of Annonaceous Acetogenins

Annonaceous acetogenins, isolated from the Annonaceae plants, have been attracting worldwide attention in recent years due to their biological activities, especially as growth inhibitors of certain tumor ceils [ 1 ]. They have been shown to function by blocking complex I in mitochondria [2] as well as ubiquinone-linked NADPH oxidase in the cells of specific tumor cell lines, including some multidrug-resistant ones [3]. These features make these acetogenins excellent leads for the new antitumor agents. In our previous work, the compounds 1a to 1d (Figure 1), which relies on structure simplification while maintaining all essential functionalities of the acetogenins, was in vitro tested against several human solid tumor cell lines and showed interesting cell selectivity [4]. All four analogues show remarkable activity against the HCT-8 and HT-29 cell lines, while compound 1c was found the best [4bi. In order to further investigate the effects of key structural features, a convergent parallel fragments assembly strategy was developed [4e]. In addition, the biological relevancies of typical annonaceous acetogenin mimetics were also studied [4f].     

Enantioselective synthesis of the 4-hydroxy buteneolide terminus of mucocin and related annonaceous acetogenins

The 4-hydroxy buteneolide terminus 3, applicable to mucocin 1 and related annonaceous acetogenins, was prepared in an expeditious manner from the selenocarbonate 2 via an intramolecular acyl radical cyclization followed by an enantioselective Lewis-acid catalyzed Keck-allylation reaction.     

The utility of furan-, pyrrole-, and thiophene-based 2-silyloxy dienes as demonstrated by modular synthesis of annonaceous acetogenin core units and their pyrrolidine and thiolane analogues

We report a modular strategy for obtaining the core units of annonaceous acetogenins and their nitrogen and sulfur analogues, which generates great structural diversity. This synthesis is based on the application of a reiterative vinylogous addition protocol involving a unique triad of silyloxy diene modules, 2-[(tert-butyldimethylsilyl)oxy]furan (TBSOF), N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole (TBSOP), and 2-[(tert-butyldimethylsilyl)oxy]thiophene (TBSOT) and suitable heteroatom-stabilized carbenium ions. By combining TBSOF, TBSOP, and TBSOT nucleophilic synthons with certain tetrahydrofuran, pyrrolidine, and thiolane acceptors, the construction of varied, adjacently linked oligo-heterocyclic motifs related to the core segments of the annonaceous acetogenins is assured. At first, the reliability of the pivotal coupling maneuver was certified, by assembling a collection of 18 model constructs, covering all oxygen, nitrogen, and sulfur heteroatom combinations (i.e., compounds 7-9, 13-15, and 19-21). This uniformed protocol was then suited to forge advanced bis-tetrahydrofuran, bis-pyrrolidine, and bis-thiolane scaffolds encompassing the heterocyclic core portion of various binuclear annonaceous acetogenins and relatives. The utility of this synthesis was demonstrated by the preparation of a repertoire of eight isomeric bis-tetrahydrofuran units, 41-48, two bis-pyrrolidine units, 62 and 63, and four bis-thiolane units, 78-81.     

Four cytotoxic annonaceous acetogenins from the seeds of Annona squamosa

Four new annonaceous acetogenins (ACGs), squamocin-I (1), II (2) and III (3) and squamoxinone-D (4), together with seven known ACGs (5–11), were isolated from the seeds of Annona squamosa. The structures of all isolates were elucidated and characterised by spectral and chemical methods. Compounds 1–4 were evaluated for their cytotoxicities against Hep G2, SMMC 7721, BEL 7402, BGC 803 and H460 human cancer cell lines. Compound 1 exhibited better potent activity than the positive compound and compound 3 shows selectively cytotoxical activity against H460 with IC₅₀ values of 0.0492 μg/ml.