Endoperoxide polyketides from a Chinese Plakortis simplex: Further evidence of the impact of stereochemistry on antimalarial activity of simple 1,2-dioxanes
文献类型：期刊论文
| 作者 | Chianese, Giuseppina1; Persico, Marco1; Yang, Fan2; Lin, Hou-Wen2; Guo, Yue-Wei3 ; Basilico, Nicoletta4; Parapini, Silvia5; Taramelli, Donatella5; Taglialatela-Scafati, Orazio1; Fattorusso, Caterina1
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| 刊名 | BIOORGANIC & MEDICINAL CHEMISTRY
 |
| 出版日期 | 2014-09-01 |
| 卷号 | 22期号:17页码:4572-4580 |
| 关键词 | Marine sponges 1,2-Dioxanes In vitro antimalarial activity Stereochemistry Computational analysis |
| ISSN号 | 0968-0896 |
| DOI | 10.1016/j.bmc.2014.07.034 |
| 文献子类 | Article |
| 英文摘要 | Chemical investigation of the organic extract obtained from the sponge Plakortis simplex collected in the South China Sea afforded five new polyketide endoperoxides (2 and 4-7), along with two known analogues (1 and 3). The stereostructures of these metabolites have been deduced on the basis of spectroscopic analysis and chemical conversion. The isolated endoperoxide derivatives have been tested for their in vitro antimalarial activity against Plasmodium falciparum strains, showing IC50 values in the low micromolar range. The structure-activity relationships were analyzed by means of a detailed computational investigation and rationalized in the light of the mechanism of action proposed for this class of simple antimalarials. The relative orientation of the atoms involved in the putative radical generation and transfer reaction was demonstrated to have a great impact on the antimalarial activity. The resulting 3D pharmacophoric model can be a useful guide to design simple and effective antimalarial lead compounds belonging to the class of 1,2-dioxanes. (C) 2014 Elsevier Ltd. All rights reserved. |
| WOS关键词 | PLASMODIUM-FALCIPARUM ; SPONGE ; MANADOPEROXIDES ; CYCLOPEROXIDES ; PEROXIDES ; AGENTS |
| 资助项目 | European Union: Project Bluegenics[311848] ; European Union: Project IRSES[246987] ; Italian MIUR: FIRB Project[RBFR12WB3W_003] ; China National Funds for Distinguished Young Scientists[81225023] ; National Natural Science Foundation of China[81172978] ; National Natural Science Foundation of China[41106127] ; National High Technology Research and Development Program of China[2011AA09070107] ; National High Technology Research and Development Program of China[2013AA092902] ; [12XD1400200] |
| WOS研究方向 | Biochemistry & Molecular Biology ; Pharmacology & Pharmacy ; Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000341293300005 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/276926]  |
| 专题 | 天然药物化学研究室 中科院受体结构与功能重点实验室 新药研究国家重点实验室 |
| 通讯作者 | Lin, Hou-Wen |
| 作者单位 | 1.Univ Naples Federico II, Dipartimento Farm, I-80131 Naples, Italy; 2.Shanghai Jiao Tong Univ, Key Lab Marine Drugs, Dept Pharm, Renji Hosp,Sch Med, Shanghai 200127, Peoples R China; 3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China; 4.Univ Milan, Dipartimento Sci Biomed Chirurg & Odontoiatr, I-20133 Milan, Italy; 5.Univ Milan, Dipartimento Sci Farmacol & Biomol, I-20133 Milan, Italy |
| 推荐引用方式 GB/T 7714 | Chianese, Giuseppina,Persico, Marco,Yang, Fan,et al. Endoperoxide polyketides from a Chinese Plakortis simplex: Further evidence of the impact of stereochemistry on antimalarial activity of simple 1,2-dioxanes[J]. BIOORGANIC & MEDICINAL CHEMISTRY,2014,22(17):4572-4580. |
| APA | Chianese, Giuseppina.,Persico, Marco.,Yang, Fan.,Lin, Hou-Wen.,Guo, Yue-Wei.,...&Fattorusso, Caterina.(2014).Endoperoxide polyketides from a Chinese Plakortis simplex: Further evidence of the impact of stereochemistry on antimalarial activity of simple 1,2-dioxanes.BIOORGANIC & MEDICINAL CHEMISTRY,22(17),4572-4580. |
| MLA | Chianese, Giuseppina,et al."Endoperoxide polyketides from a Chinese Plakortis simplex: Further evidence of the impact of stereochemistry on antimalarial activity of simple 1,2-dioxanes".BIOORGANIC & MEDICINAL CHEMISTRY 22.17(2014):4572-4580. |
入库方式： OAI收割
来源：上海药物研究所
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