Acylphloroglucinol derivatives from the twigs and leaves of Callistemon salignus
Acylphloroglucinol derivatives from the twigs and leaves of Callistemon salignus
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DOI：
10.1016/j.tet.2017.01.052
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发表时间：
2017-04-06
期刊：
影响因子：
2.1
通讯作者：
Liu, Hai-Yang
中科院分区：
文献类型：
--
作者：
Qin, Xu-Jie;Liu, Hui;Liu, Hai-Yang
从金盏花（Callistemon salignus）的枝条和叶片中分离得到3个新的酰基间苯三酚衍生物，callisalignones A-C(1-3)， 6个新的meroteroids， callisalignene A-F(4-9)，以及18个已知的类似物（10-27）。通过综合光谱证据（核磁共振、质谱和电子圆二色性计算）确定了它们的结构和绝对构型。通过与callisalignone B(2)的ECD光谱比较，确定了calisalignone B（13）和H（14）的绝对构型。callisalign烯B和C是-三酮和酰基间苯三酚的新加合物，而callisalign烯A-D则是酰基间苯三酚和-邻苯二烯通过hetero-Diels-Alder反应形成的不同偶联模式的新二萜类化合物。桃金酮D（15）对金黄色葡萄球菌和3株耐药金黄色葡萄球菌的MIC值分别为1.953和0.975 μ g/mL，具有显著的抑菌活性。异omyrtucommone B（17）对大肠杆菌具有显著的抑菌活性，MIC值为0.122 μ g/mL。细胞毒实验显示，isomyrtucommone B（17）对HCT116的IC50值为2.09 +/- 0.10 μ M. (C) 2017 Elsevier Ltd.。版权所有。
Three new acylphloroglucinol derivatives, callisalignones A-C (1-3), six new meroterpenoids, callisalignenes A-F (4-9), along with 18 known analogues (10-27) were isolated from the twigs and leaves of Callistemon salignus. Their structures and absolute configurations were established by comprehensive spectroscopic evidences (NMR, MS, amd electronic circular dichroism calculations). The absolute configurations of callistenones B (13) and H (14) were determined by comparison of their ECD spectra with that of callisalignone B (2). Callisalignones B and C are new adducts of beta-triketone and acylphloroglucinol, whereas callisalignenes A-D are new meroterpenoids of acylphloroglucinol and alpha-phellandrene with different coupling models via hetero-Diels-Alder reaction, respectively. Myrtucommulone D (15) showed significant antibacterial activity against Staphylococcus aureus and three drug resistant S. aureus strains with MIC values of 1.953 and 0.975 mu g/mL, respectively. Isomyrtucommulone B (17) displayed remarkable antibacterial activity against Escherichia coli with an MIC value of 0.122 mu g/mL. Cytotoxic assay revealed that isomyrtucommulone B (17) was the most active against HCT116 with an IC50 value of 2.09 +/- 0.10 mu M. (C) 2017 Elsevier Ltd. All rights reserved.