Recent Progress of Natural Product Spirobisnaphthalenes
- Corresponding author: Wang Ming'an, wangma@cau.edu.cn
Citation:
Liu Xinlei, Zhao Yu, Wang Weiwei, Wang Ming'an, Zhou Ligang. Recent Progress of Natural Product Spirobisnaphthalenes[J]. Chinese Journal of Organic Chemistry,
;2017, 37(11): 2883-2894.
doi:
10.6023/cjoc201705020
Miyashita, K.; Imanishi, T. Chem. Rev. 2005, 105, 4515.
doi: 10.1021/cr040613k
Zhou, L.; Zhao, J.; Shao, T.; Cai, X.; Peng, Y. Mini-Rev. Med. Chem. 2010, 10, 977.
doi: 10.2174/138955710792007178
Cai, Y. S.; Guo, Y. W.; Krohn, K. Nat. Prod. Rep. 2010, 27, 1840.
doi: 10.1039/c0np00031k
Liu, X.-T.; Schwan, W. R.; Volk, T. J.; Rott, M.; Liu, M.; Huang, P.; Liu, Z.; Wang, Y.; Zitomer, N. C.; Sleger, C.; Hartsel, S.; Monte, A.; Zhang, L. J. Nat. Prod. 2012, 75, 1534.
doi: 10.1021/np300221a
Cai, Y. S.; Kurtan, T.; Miao, Z. H.; Mandi, A.; Istvan, K.; Liu, H. L.; Ding, J.; Guo, Y. W. J. Org. Chem. 2011, 76, 1821.
doi: 10.1021/jo1024877
Martínez-Luis, S.; Cherigo, L.; Higginbotham, S.; Arnold, E.; Spadafora, C.; Ibañez, A.; Gerwick, W. H.; Cubilla-Rios, L. Int. Microbiol. 2011, 14, 95.
Shao, T.; Song, X.; Chen, G.; Han, C.; Zheng, C.; Yao, G. Chin. Tradit. Herb. Drugs 2013, 44, 2208(in Chinese).
Ekuadzi, E.; Dickson, R. A.; Fleischer, T. C.; Amponsah, I. K.; Pistorius, D.; Oberer, L. J. Nat. Prod. 2014, 28, 1210.
doi: 10.1080/14786419.2014.921685
Ai, W.; Wei, X.; Lin, X.; Sheng, L.; Wang, Z.; Tu, Z.; Yang, X.; Zhou, X.; Li, J.; Liu, Y. Tetrahedron 2014, 70, 5806.
doi: 10.1016/j.tet.2014.06.041
Pudhom, K.; Teerawatananond, T. J. Nat. Prod. 2014, 77, 1962.
doi: 10.1021/np500068y
Pudhom, K.; Teerawatananond, T.; Chookpaiboon, S. Mar. Drugs 2014, 12, 1271.
doi: 10.3390/md12031271
Lu, X.; Chen, G.; Li, Z.; Zhang, Y.; Wang, Z.; Rong, W.; Pei, Y.; Pan, H.; Hua, H.; Bai, J. Helv. Chim. Acta 2014, 97, 1289.
doi: 10.1002/hlca.201300436
Macías-Rubalcava, M. L.; Ruiz-Velasco, Sobrino, M. E.; Meléndez-González, C.; Hernández-Ortega, S. J. Agric. Food Chem. 2014, 62, 3553.
doi: 10.1021/jf500965k
Shan, T.; Tian, J.; Wang, X.; Mou, Y.; Mao, Z.; Lai, D.; Dai, J.; Peng, Y.; Zhou, L.; Wang, M. J. Nat. Prod. 2014, 77, 2151.
doi: 10.1021/np400988a
Li, T.-X.; Yang, M.-H.; Wang, X.-B.; Wang, Y.; Kong, L.-Y. J. Nat. Prod. 2015, 78, 2511.
doi: 10.1021/acs.jnatprod.5b00008
Bunyapaiboonsri, T.; Yoiprommarat, S.; Nopgason, R.; Intereya, K.; Suvannakad, R.; Sakayaroj, J. Tetrahedron 2015, 71, 5572.
doi: 10.1016/j.tet.2015.06.061
Yu, H.; Bai, H.; Mei, W.; Zuo, W.; Wang, H.; Yang, J.; Dai, H. J. Trop. Subtrop. Bot. 2015, 23, 323.
Xu, Y.; Mafezoli, J.; Oliveira, M. C. F.; Jana, M. U.; Arnold, A. E.; Gunatilaka, A. A. L. J. Nat. Prod. 2015, 78, 2738.
doi: 10.1021/acs.jnatprod.5b00717
Happi, G.; Kouama, S. F.; Talontsi, F.; Zühlke, S.; Lamshöft, M.; Spiteller, M. Fitoterapia 2015, 102, 35.
doi: 10.1016/j.fitote.2015.01.018
Jiang, H.; Ma, S.-G.; Li, Y.; Liu, Y.-B.; Li, L.; Qu, J.; Yu, S.-S. Bioorg. Med. Chem. Lett. 2016, 26, 4832.
doi: 10.1016/j.bmcl.2016.08.019
Xie, F.; Chang, W.; Zhang, M.; Li, Y.; Li, W.; Shi, H.; Zheng, S.; Lou, H. Sci. Rep. 2016, 6, 33687.
doi: 10.1038/srep33687
Kamal, N.; Viegelmann, C. V.; Clements, C. J.; Edrada-Ebel, R. Planta Med. 2016, 83, 565.
doi: 10.1055/s-0042-118601
Siridechakorn, I.; Yue, Z.; Mittraphab, Y.; Lei, X.; Pudhom, K. Bioorg. Med. Chem. 2017, 25, 2878.
doi: 10.1016/j.bmc.2017.02.054
(a) Van der Sar, S. A.; Blunt, J. W.; Munro, M. H. G. Org. Lett. 2006, 8, 2059.
(b) Van der Sar, S. A.; Lang, G.; Mitova, M. I.; Blunt, J. W.; Cole, A. L. J.; Cummings, N.; Ellis, G.; Munro, M. H. G. J. Org. Chem. 2008, 73, 8635.
Chen, X.; Shi, Q.; Lin, G.; Guo, S.; Yang, J. J. Nat. Prod. 2009, 72, 1712.
doi: 10.1021/np900302w
Masahiko, I.; Panida, C.; Pranee, R.; Kitlada, S.; Prasert, S.; Palangpon, K.; Samran, P. J. Antibiot. 2015, 68, 334.
doi: 10.1038/ja.2014.153
Chen, S.; Chen, D.; Cai, R.; Cui, H.; Long, Y.; Lu, Y.; Li, C.; She, Z. J. Nat. Prod. 2016, 79, 2397.
doi: 10.1021/acs.jnatprod.6b00639
Wang, K.; Bao, L.; Ma, K.; Qi, W.; Song, F.; Yao, Y.; Yin, W.; Zhang, L.; Huang, Y.; Han, J.; Liu, H. Eur. J. Org. Chem. 2016, 25, 4338.
Erika, E. E. Ph.D Dissertation, University of Pittsburgh, USA, 2008.
Krohn, K.; Wang, S.; Ahmed, I.; Altun, S.; Aslan, A.; Florke, U.; Kock, I.; Schlummer, S. Eur. J. Org. Chem. 2010, 4476.
Wang, R.; Liu, G.; Yang, M.; Wang, M.; Zhou, L. Molecules 2016, 21, 600.
doi: 10.3390/molecules21050600
Aslan, A.; Altun, S.; Ahmed, I.; Florke, U.; Schulz, B.; Krohn, K. Eur. J. Org. Chem. 2011, 1176.
Murphy, A. C.; Devenish, S. R. A.; Muscroft-Taylor, A. C.; Blunt, J. W.; Munro, M. H. G. Org. Biomol. Chem. 2008, 6, 3854.
doi: 10.1039/b812263f
Tsukamoto, H.; Hanada, S.; Kumasaka, K.; Kagaya, N.; Izumikawa, M.; Shinya, K.; Doi, T.; Org. Lett. 2016, 18, 4848.
doi: 10.1021/acs.orglett.6b02328
Bode, H. B.; Wegner, B.; Zeeck, A. J. Antibiot. 2000, 53, 153.
doi: 10.7164/antibiotics.53.153
Chi, S.; Heathcock, C. H. Org. Lett. 1999, 1, 3.
doi: 10.1021/ol990020+
Ai, W.; Lin, L.; Wang, Z.; Lu, X.; Mangaladoss, F.; Yang, X.; Zhou, X.; Tu, Z.; Liu, Y. J. Antibiot. 2015, 68, 213.
doi: 10.1038/ja.2014.126
Zhao, J.; Zheng, B.; Li, Y.; Shan, T.; Mou, Y.; Lu, S.; Li, P.; Zhou, L. Molecules 2011, 16, 847.
doi: 10.3390/molecules16010847
Zhao, J.; Li, Y.; Shan, T.; Mou, Y.; Zhou, L. World J. Microbiol. Biotechnol. 2011, 27, 2753.
doi: 10.1007/s11274-011-0750-2
Li, Y.; Li, P.; Mou, Y.; Zhao, J.; Shan, T.; Ding, C.; Zhou, L. World J. Microbiol. Biotechnol. 2012, 28, 1407.
doi: 10.1007/s11274-011-0940-y
Mou, Y.; Meng, J.; Fu, X.; Wang, X.; Tian, J.; Wang, M.; Peng, Y.; Zhou, L. Molecules 2013, 18, 15587.
doi: 10.3390/molecules181215587
Zhao, J.; Wang, X.; Sun, W.; Mou, Y.; Peng, Y.; Zhou, L. Electron. J. Biotechnol. 2013, 16, 1.
Mou, Y.; Luo, H.; Mao, Z.; Shan, T.; Sun, W.; Zhou, K.; Zhou, L. Int. J. Mol. Sci. 2013, 14, 979.
doi: 10.3390/ijms14010979
Li, Y.; Shan, T.; Mou, Y.; Li, P.; Zhao, J.; Zhao, W.; Peng, Y.; Zhou, L.; Ding, C. Molecules 2012, 17, 3761.
doi: 10.3390/molecules17043761
Mou, Y.; Zhou, K.; Xu, D.; Yu, R.; Li, J.; Yue, Y.; Zhou, L. Nat. Prod. Res. Dev. 2015, 27, 205(in Chinese).
Mou, Y.; Li, J.; Zhou, K.; Yu, R.; Xu, D.; Luo, H.; Lai, D.; Zhou, L. Trop. J. Pharm. Res. 2015, 14, 407.
doi: 10.4314/tjpr.v14i3.8
Mou, Y.; Xu, D.; Mao, Z.; Dong, X.; Lin, F.; Wang, A.; Lai, D.; Zhou, L.; Xie, B. Molecules 2015, 20, 20320.
doi: 10.3390/molecules201119700
Mou, Y.; Zhou, K.; Xu, D.; Yu, R.; Li, J.; Yin, C.; Zhou, L. Trop. J. Pharm. Res. 2015, 14, 241.
doi: 10.4314/tjpr.v14i2.8
Ortega, H. E.; Teixeira, E. M.; Rabello, A.; Higginbotham, S.; Cubilla-Ríos, L. Nat. Chem. Commun. 2014, 9, 95.
Chen, X.; Shi, Q.; Wang, C.; Li, B.; Wang, A.; Guo, S. Mycosys-tema 2013, 32, 729.
Li, B.; Wang, C.; Chen, X.; Lyu, J.; Guo, S. J. Chromatogr. B 2013, 938, 1.
doi: 10.1016/j.jchromb.2013.08.004
Cai, X.; Shan, T.; Li, P.; Huang, Y.; Xu, L.; Zhou, L.; Wang, M.; Jiang, W. Nat. Prod. Commun. 2009, 4, 1469.
Zhong L.; Wang L.; Shan T.; Liu H.; Zhao J.; Xu L.; Zhou L. Nat. Prod. Res. Dev. 2012, 24, 20(in Chinese).
doi: 10.3969/j.issn.1001-6880.2012.01.006
Martinez-Luis, S.; Della-Togna, G.; Coley, P.; Kursar, T.; Gerwick, W.; Cubilla-Rios, L. J. Nat. Prod. 2008, 71, 2011.
doi: 10.1021/np800472q
Martinez-Luis, S.; Della-Togna, G.; Coley, P.; Kursar, T.; Gerwick, W.; Cubilla-Rios, L. Rev. Latinoam. Quim. 2009, 37, 104.
Dong, J.; Song, H.; Li, J.; Tang, Y.; Sun, R.; Wang, L. J. Nat. Prod. 2008, 71, 952.
doi: 10.1021/np800034g
Zhou, Y.; Shen, K.; Dong, J.; Wang, L.; Sun, R.; Wang, C.; Wang, L. Zhang, K. Chin. J. Antibiot. 2009, 34, 74(in Chinese).
Tian, J.; Liu, X.; Liu, Z.; Lai, D.; Zhou, L. Pest Manage. Sci. 2016, 72, 961.
doi: 10.1002/ps.2016.72.issue-5
Macías-Rubalcava, M. L.; Ruiz-Velasco, Sobrino, M. E.; Meléndez-González, C.; King-Díaz, B.; Lotina-Hennsen, B. J. Photochem. Photobiol. B 2014, 138, 17.
doi: 10.1016/j.jphotobiol.2014.05.003
Macías-Rubalcava, M. L.; Hernández-Bautista, B. E.; Jemenez-Estrada, M.; Gonzalez, M. C.; Glenn, A. E.; Hanlin, R. T.; Hernández-Ortega, S.; Saucedo-Garcia, A.; Muria-Ganzalez, J. M.; Anaya, A. L. Phytochemistry 2008, 69, 1185.
doi: 10.1016/j.phytochem.2007.12.006
Gocer, H.; Aslan, A.; Gulcin, I.; Supuran, C. T. J. Enzyme Inhib. Med. Chem. 2015, 31, 503.
Arabaci, B.; Gulcin, I.; Alwasel, S. Molecules 2014, 19, 10103.
doi: 10.3390/molecules190710103
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Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb2 complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
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