Coqueiro Aline, Choi Young H, Verpoorte Robert, Gupta Karthick B S S, De Mieri Maria, Hamburger Matthias, Young Maria C M, Stapleton Paul, Gibbons Simon, Bolzani Vanderlan da S
Natural Products Laboratory, Institute of Biology, Leiden University , Sylviusweg 72, Leiden, 2333 BE, The Netherlands.
Research Department of Pharmaceutical and Biological Chemistry, UCL School of Pharmacy , 29-39 Brunswick Square, London, WC1N 1AX, United Kingdom.
J Nat Prod. 2016 Mar 25;79(3):470-6. doi: 10.1021/acs.jnatprod.5b00858. Epub 2016 Feb 22.
Bioactivity-guided fractionation of the EtOH extract of the branches of Kielmeyera variabilis led to the isolation of a new acylphoroglucinol (1), which was active against all the MRSA strains tested herein, with pronounced activity against strain EMRSA-16. Compound 1 displayed an MIC of 0.5 mg/L as compared with an MIC of 128 mg/L for the control antibiotic norfloxacin. The structure of the new compound was elucidated by 1D and 2D NMR spectroscopic analysis and mass spectrometry, and experimental and calculated ECD were used to determine the absolute configurations. The compounds β-sitosterol (2), stigmasterol (3), ergost-5-en-3-ol (4), and osajaxanthone (5) also occurred in the n-hexane fraction. The EtOAc fraction contained nine known xanthones: 3,6-dihydroxy-1,4,8-trimethoxyxanthone (6), 3,5-dihydroxy-4-methoxyxanthone (7), 3,4-dihydroxy-6,8-dimethoxyxanthone (8), 3,4-dihydroxy-2-methoxyxanthone (9), 5-hydroxy-1,3-dimethoxyxanthone (10), 4-hydroxy-2,3-dimethoxyxanthone (11), kielcorin (12), 3-hydroxy-2-methoxyxanthone (13), and 2-hydroxy-1-methoxyxanthone (14), which showed moderate to low activity against the tested MRSA strains.
对变色基尔米耶拉树枝乙醇提取物进行生物活性导向的分级分离,得到一种新的酰基间苯三酚(1),它对本文测试的所有耐甲氧西林金黄色葡萄球菌(MRSA)菌株均有活性,对EMRSA - 16菌株有显著活性。化合物1的最低抑菌浓度(MIC)为0.5mg/L,而对照抗生素诺氟沙星的MIC为128mg/L。通过一维和二维核磁共振光谱分析以及质谱对新化合物的结构进行了阐明,并使用实验和计算的电子圆二色光谱(ECD)来确定其绝对构型。化合物β - 谷甾醇(2)、豆甾醇(3)、麦角甾 - 5 - 烯 - 3 - 醇(4)和奥沙黄酮(5)也存在于正己烷馏分中。乙酸乙酯馏分含有九种已知的氧杂蒽酮:3,6 - 二羟基 - 1,4,8 - 三甲氧基氧杂蒽酮(6)、3,5 - 二羟基 - 4 - 甲氧基氧杂蒽酮(7)、3,4 - 二羟基 - 6,8 - 二甲氧基氧杂蒽酮(8)、3,4 - 二羟基 - 2 - 甲氧基氧杂蒽酮(9)、5 - 羟基 - 1,3 - 二甲氧基氧杂蒽酮(10)、4 - 羟基 - 2,3 - 二甲氧基氧杂蒽酮(11)、基尔考林(12)、3 - 羟基 - 2 - 甲氧基氧杂蒽酮(13)和2 - 羟基 - 1 - 甲氧基氧杂蒽酮(14),它们对测试的MRSA菌株表现出中度至低度活性。