溴酚酸：斐济红藻 Callophycus sp. 的生物活性天然产物
Bromophycoic acids: bioactive natural products from a Fijian red alga Callophycus sp.
机构信息
School of Biology, Aquatic Chemical Ecology Center, Institute of Bioengineering and Biosciences, Georgia Institute of Technology, Atlanta, Georgia 30332, USA.
出版信息
J Org Chem. 2012 Sep 21;77(18):8000-6. doi: 10.1021/jo301246x. Epub 2012 Sep 5.
Abstract
Bioassay-guided fractionation of extracts from a Fijian red alga in the genus Callophycus resulted in the isolation of five new compounds of the diterpene-benzoate class. Bromophycoic acids A-E (1-5) were characterized by NMR and mass spectroscopic analyses and represent two novel carbon skeletons, one with an unusual proposed biosynthesis. These compounds display a range of activities against human tumor cell lines, malarial parasites, and bacterial pathogens including low micromolar suppression of MRSA and VREF.
摘要
从斐济红藻 Callophycus 属中提取的生物测定指导分离，得到了五个新的二萜-苯甲酸酯类化合物。溴藻酸 A-E（1-5）通过 NMR 和质谱分析进行了表征，代表了两种新型的碳骨架，其中一种具有不寻常的提议生物合成。这些化合物对人类肿瘤细胞系、疟原虫寄生虫和包括耐甲氧西林金黄色葡萄球菌（MRSA）和万古霉素耐药肠球菌（VREF）在内的细菌病原体显示出一系列的活性，抑制活性低至微摩尔水平。
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ChemMedChem. 2011 Sep 5;6(9):1572-7. doi: 10.1002/cmdc.201100252. Epub 2011 Jul 5.
3
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Bioorg Med Chem Lett. 2010 Oct 1;20(19):5662-5. doi: 10.1016/j.bmcl.2010.08.031. Epub 2010 Aug 10.
4
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6
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7
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9
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Bioinformatics. 2007 Nov 1;23(21):2947-8. doi: 10.1093/bioinformatics/btm404. Epub 2007 Sep 10.
10
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