海南染木树叶中的蒽醌成分研究
收稿日期: 2013-10-14
修回日期: 2013-11-13
网络出版日期: 2013-11-21
基金资助
国家自然科学基金（Nos. 21162009，31360069）；973计划前期研究专项课题（No. 2011CB512010）；国家级大学生创新训练（No. 201311658019）资助项目.
Anthraquinones from the Leaves of Saprosma hainanense
Received date: 2013-10-14
Revised date: 2013-11-13
Online published: 2013-11-21
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21162009, 31360069), the 973 Research Program of the Ministry of Science and Technology of China (No. 2011CB512010), and the National Undergraduate Innovation Training Programs (No. 201311658019).
从海南染木树叶乙醇提取物的乙酸乙酯萃取部位分离得到9个蒽醌类化合物，采用高分辨质谱、一维和二维核磁共振等现代波谱技术，鉴定上述化合物的结构分别为：7-羟基-1，2-二甲氧基-6-甲基-9，10-蒽醌（1），1-羟基-3，6-二甲氧基-9，10-蒽醌（2），10，10’-二蒽酮（3），9，10-蒽醌（4），甲基异茜草素（5），虎刺醇（6），2-羟基-3-甲基-9，10-蒽醌（7），3-羟基-1，2-二甲氧基-9，10-蒽醌（8）和3-羟基-1-甲氧基-2-甲酯基-9，10-蒽醌（9）. 其中化合物1和2为新天然产物，且化合物1的波谱数据迄今未见任何报道. 除化合物9外，其余化合物均为首次从该属植物中分离得到. 抗菌活性测试显示，化合物2和9对多种菌株具有很好的抑制作用，尤其是金黄色葡萄球菌，最小抑菌浓度（MIC）值均达到0.078 μg/mL；化合物1和6对枯草芽孢杆菌、金黄色葡萄球菌显示出与阳性对照环丙沙星相当或者更强的抑制活性.
王燕 , 陈文豪 , 陈光英 , 宋小平 , 张大帅 , 傅波 , 陈怡 . 海南染木树叶中的蒽醌成分研究[J]. 有机化学, 2014 , 34(3) : 522 -525 . DOI: 10.6023/cjoc201310014
Nine anthraquinones were isolated from the leaves of Saprosma hainanense. On the basis of spectroscopic data analyses (HRESIMS, 1D-and 2D-NMR) and that reported in the literature, The structures were established as 7-hydroxy-1,2-dimethoxy-6-methylanthraquinone (1), 1-hydroxy-3,6-dimethoxyanthraquinone (2), 10,10'-bianthrone (3), 9,10-anthraquinone (4), rubiadin (5), ramnacanthol (6), 2-hydroxy-3-methyl-9,10-anthraquinone (7), 3-hydroxy-1,2-dimethoxyanthraquinone (8) and 3-hydroxy-1-methoxy-2-carbomethoxy-9,10-anthraquinone (9). Among them, compounds 1 and 2 were new natural products, and 1 has no spectroscopic data reported until now. All compounds except 9 were isolated from this genus for the first time. Compounds 2 and 9 showed stronger inhibitory activities to the most of the bacteria, especially to the Staphylococcus aureus, with the minimum inhibitory concentration (MIC) values of 0.087 μg/mL. Compounds 1 and 6 exhibited the higher inhibitory activities against Bacillus subtilis and Staphylococcus aureus than positive control ciprofloxacin.
[1] Wang, Q.; Lin, H. W.; Shen, Y.; Jin, C. Y.; Guo, C. Lishizhen Med. Mater. Med. Res. 2000, 9, 793 (in Chinese).
(王青, 林厚文, 沈阳, 金翠英, 郭澄, 时珍国医国药, 2000, 9, 793.)
[2] Wang, Q.; Jin, C. Y.; Lin, H. W.; Shen, Y. Chin. Med. Mater. 2000, 23, 634 (in Chinese).
(王青, 金翠英, 林厚文, 沈阳, 中药材, 2000, 23, 634.)
[3] Ling, S. K.; Komorita, A.; Tanaka, T.; Fujioka, T.; Mihashi, K.; Kouno, I. J. Nat. Prod. 2002, 65, 656.
[4] Ling, S. K.; Komorita, A.; Tanaka, T.; Mihashi, K.; Kouno, I. Chem. Pharm. Bull. 2002, 50, 1035.
[5] Singh, D. N.; Verma, N.; Raghuwanshi, S.; Shukla, P. K.; Kulshreshtha, D. K. Bioorg. Med. Chem. Lett. 2006, 16, 4512.
[6] Wang, L.; Chen, G. Y.; Han, R.; Yuan, Y.; Yang, B.; Zhang, Y.; Wang, J.; Zhong, X. Q.; Huang, X. Chem. Pharm. Bull. 2011, 47(3), 338.
[7] Jacobson, R. A.; Roger, A. Opianic Acid Phenols 1925, 47, 2011.
[8] Iwao, M.; Kuraisin, T. Bull. Chem. Soc. Jpn. 1987, 60, 4051.
[9] Huang, N. Z.; Lakshmikantham, M. V.; Cava, M. P. J. Org. Chem. 1987, 52(2), 169.
[10] Mohanlall, V.; Odhav, B. J. Med. Plants Res. 2013, 7(14), 877.
[11] Zhao, F.; Wang, S. J.; Wu, X. L.; Yu, Y.; Yue, Z. G.; Liu, B.; Lin, S.; Zhu, C. G.; Yang, Y. C.; Shi, J. G. China J. Chin. Mater. Med. 2011, 36(21), 2980 (in Chinese).
(赵峰, 王素娟, 吴秀丽, 于洋, 岳正刚, 刘波, 林生, 朱承根, 杨永春, 石建功, 中国中药杂志, 2011, 36(21), 2980.)
[12] Kamiya, K.; Hamabe, W.; Tokuyama, S.; Hirano, K.; Satake, T.; Yonezawa, Y. K.; Yoshida, H.; Mizushina, Y. Food Chem. 2010, 118, 725.
[13] Zhang, H. L.; Zhang, Q. W.; Zhang, X. Q.; Ye, W. C.; Wang, Y. T. Chin. J. Nat. Med. 2010, 8(3), 1 (in Chinese).
(张海龙, 张庆文, 张晓琦, 叶文才, 王一涛, 中国天然药物, 2010, 8(30), 1.)
[14] Ling, S. K.; Akiko, K.; Takashi, T.; Fujioka, T.; Mihashi, K.; Kouno, I. Chem. Pharm. Bull. 2002, 50(8), 1035.
/
| 〈 |
|
〉 |
