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中国番荔枝科植物抗癌有效成分研究 总被引:6,自引:0,他引:6
介绍了近年来我们实验室中国番荔枝科植物抗癌有效成分研究工作。从番荔枝科5种紫玉盘属植物,5种哥纳香属植物,1种番荔枝属植物,1种囊瓣木属植物中分离得到59种新的番荔枝内酯,32种新的多氧取代环己烯,12种新的苯乙烯吡喃酮和3种新的生物碱,并通过化学和光谱方法鉴定了它们的结构。大部分化合物显示了较强的抗癌活性。并对抗癌活性成分海南哥纳香醇甲进行了全合成。 相似文献
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Goniothalamin是由番荔枝科(annonaceae)家族中分离出的抗肿瘤活性天然产物分子,具有苯乙烯基及α,β-不饱和-δ-内酯两个关键片段。药物化学家近年来利用氟原子或者含氟基团对这两个关键药效基团进行了系统的结构修饰,试图利用氟独特的物理化学性质调控药效基团电子属性以获取具有更佳生理活性的化合物。本文主要从含氟基团引入的位点设计以及合成方法角度,总结了goniothalamin内酯含氟修饰物合成与生理活性研究进展,并进行了发展前景展望。 相似文献
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海南狭瓣鹰爪花(Artabotrys hainanensis R.E. Fries)为番荔枝科鹰爪花属植物,该属植物在世界上约有100种,主要分布在热带和亚热带地区.我国产4种,广东有2种,即香港鹰爪花(A.hongkongensis Hance)和鹰爪花[A.hexapetalus(Linn.f)Bhandari],海南有2种,即毛叶鹰爪花(A.pilosus)和海南狭瓣鹰爪花(A.hainanensis R.E. Fries).海南鹰爪花在海南岛分布较广,储量十分丰富.在民间,海南狭瓣鹰爪花作药用植物已有很长历史,具有清热解毒、消炎止痛的作用,常用作治疗疟疾和头颈部淋巴结核.番荔枝科植物富含抗肿瘤活性成分而被受国内外学者关注,先后对鹰爪花属多种植物的根、茎(皮)、叶和果实的化学成分进行了研究,分离得到生物碱类、黄酮flavone类和萜类[1-4]等四十多种化合物.海南狭瓣鹰爪花为海南特有植物,其化学成分研究至今尚未见报道.为寻找新的药理活性成分,我们对海南狭瓣鹰爪花茎和叶的化学成分进行了研究.海南狭瓣鹰爪花药材采集于海南尖峰岭. 相似文献
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Shi Sun Jingchun Liu Xiuxiu Sun Wenjun Zhu Fei Yang Lisa Felczak Q. Ping Dou Kequan Zhou 《Tetrahedron letters》2017,58(19):1895-1899
Five bioactive Annonaceous acetogenins, including three new compounds, annonamuricins A (1), B (2), and C (3), one registered but no spectral data reported compounds, annonamuricin D (4), and one known compound annonacin (5) were isolated from Graviola fruit (Annona muricata) and further determined through bioassay-guided fractionation. All five compounds are C35 Anonnonaceous acetogenins with a mono-tetrahydrofuran ring and four hydroxyls. Their structures were elucidated using spectral methods as well as chemical modification after isolation via chromatographic techniques and HPLC purification. These acetogenins demonstrated potent anti-proliferative activities against human prostate cancer PC-3 cells. 相似文献
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The total synthesis of mono-THF acetogenins, cis-solamin A and B, and reticulatacin, was accomplished starting with muricatacin. The backbone of the mono-THF acetogenins was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and γ-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure γ-lactone moiety. Notably, cis-THF compounds were obtained without using protective groups. 相似文献
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Arndt S Emde U Bäurle S Friedrich T Grubert L Koert U 《Chemistry (Weinheim an der Bergstrasse, Germany)》2001,7(5):993-1005
The natural product hybrids quinone-mucocin and quinone- squamocin D were synthesized. In these hybrids, the butenolide unit of the annonaceous acetogenins mucocin and squamocin D is exchanged for the quinone moiety of the natural complex I substrate ubiquinone. For both syntheses, a modular, highly convergent approach was applied. Quinone-mucocin was constructed out of a tetrahydropyran (THP) component 1, a tetrahydrofuran (THF) unit 2, and a quinone precursor 3. A stereoselective, organometallic coupling reaction was chosen for the addition of the THP unit to the rest of the molecule. In the final step, the oxidation to the free quinone was achieved by using cerium(IV) ammonium nitrate (CAN) as the oxidizing agent. Quinone-squamocin D was assembled in a similar manner, from the chiral side chain bromide 16, the central bis-THF core 17, and the quinone precursor 18. Inhibition of complex I (isolated from bovine heart mitochondria) by the quinone acetogenins and several smaller building blocks was examined; quinone mucocin and quinone-squamocin D act as strong inhibitors of complex I. These results and the data from the smaller substructures indicate that other substructures of the acetogenins besides the butenolide group, such as the polyether component and the lipophilic left-hand side chain, are necessary for the strong binding of the acetogenins to complex I. 相似文献
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Wang LQ Nakamura N Meselhy MR Hattori M Zhao WM Cheng KF Yang RZ Qin GW 《Chemical & pharmaceutical bulletin》2000,48(8):1109-1113
Four novel mono-tetrahydrofuran (THF) acetogenins, montanacins B-E (1-4), were isolated from the ethanolic extract of the leaves of Annona montana. The structures of 1-4 were established by spectroscopic methods and their absolute stereochemistries were determined by the advanced Mosher ester method. Montancins D (3) and E (4) bear a non-adjacent tetrahydropyran (THP) ring along with a THF ring and are the most unusual type of acetogenins discovered so far. 相似文献
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Thirty-six stereoisomers of bifunctional adjacent bis-THF (tetrahydrofuran) lactones have been synthesized, which can afford a complete library of the adjacent bis-THF Annonaceous acetogenins. The bis-THF lactones were synthesized, starting from the enantioselectively pure 8,9:12,13-(E,E and Z,E)-16-benzyloxy-5-hydroxy-hexadeca-1,4-olide, in a highly distereoselective manner using oxidative reactions, including rhenium(VII) oxides-mediated oxidative cyclization, Shi's asymmetric epoxidation, and Sharpless asymmetric dihydroxylation reactions. Using the nonsymmetrical bis-THF lactones, syntheses of two nonnatural acetogenins were achieved. 相似文献
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Alexandra G. Durn M. Teresa Gutirrez Francisco J. R. Mejías Jos M. G. Molinillo Francisco A. Macías 《Molecules (Basel, Switzerland)》2021,26(10)
Annona cherimola Mill., or the custard apple, is one of the species belonging to the Annonaceae family, is widely used in traditional medicine, and has been reported to be a valuable source of bioactive compounds. A unique class of secondary metabolites derived from this family are Annonaceous acetogenins, lipophilic polyketides considered to be amongst the most potent antitumor compounds. This review provides an overview of the chemical diversity, isolation procedures, bioactivity, modes of application and synthetic derivatives of acetogenins from A. cherimola Mill. 相似文献
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Yao Zhu-Jun 《合成化学》2004,12(Z1)
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]. 相似文献
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A short asymmetric approach for the synthesis of bis-tetrahydrofuran units of various annonaceous acetogenins is described. The key steps of the synthesis are self-cross metathesis and Sharpless asymmetric dihydroxylation. 相似文献