Chinese Journal of Organic Chemistry >
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).
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.
Wang Yan , Chen Wenhao , Chen Guangying , Song Xiaoping , Zhang Dashuai , Fu Bo , Chen Yi . Anthraquinones from the Leaves of Saprosma hainanense[J]. Chinese Journal of Organic Chemistry, 2014 , 34(3) : 522 -525 . DOI: 10.6023/cjoc201310014
[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.
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