Chinese Journal of Organic Chemistry >
Recent Progress of Natural Product Spirobisnaphthalenes
Received date: 2017-05-15
Revised date: 2017-06-21
Online published: 2017-07-07
Supported by
Project supported by the National Natural Science Foundation of China (No. 21172254).
Spirobisnaphthalenes (spirodioxynaphthalenes) are one class of highly oxidized natural products in which two naphthalenes are connected by spiroketal or binaphthalene spiroether. Because of their novel and complex structures, multi-chiral centers and broad bioactivities, synthetic chemists paid a lot of attention to this type of compounds in recent years. The new research progresses of spirobisnaphthalene natural products after 2010 are reviewed based on the results in our laboratory, including 62 new chemical structures, total synthesis and modification, biosynthetic pathway, bioactivities and structure-activity relationships of spirobisnaphthalenes. The objective is to promote the creation of novel drugs and agrochemicals by lead discovery and modification of natural products in China.
Key words: spirobisnaphthalene; spiroketal; natural product; synthesis; bioactivity
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
[1] Miyashita, K.; Imanishi, T. Chem. Rev. 2005, 105, 4515.
[2] Zhou, L.; Zhao, J.; Shao, T.; Cai, X.; Peng, Y. Mini-Rev. Med. Chem. 2010, 10, 977.
[3] Cai, Y. S.; Guo, Y. W.; Krohn, K. Nat. Prod. Rep. 2010, 27, 1840.
[4] 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.
[5] 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.
[6] Martínez-Luis, S.; Cherigo, L.; Higginbotham, S.; Arnold, E.; Spadafora, C.; Ibañez, A.; Gerwick, W. H.; Cubilla-Rios, L. Int. Microbiol. 2011, 14, 95.
[7] Shao, T.; Song, X.; Chen, G.; Han, C.; Zheng, C.; Yao, G. Chin. Tradit. Herb. Drugs 2013, 44, 2208(in Chinese). (邵泰明, 宋小明, 陈光英, 韩长日, 郑彩娟, 姚国贵, 中草药, 2013, 44, 2208.)
[8] Ekuadzi, E.; Dickson, R. A.; Fleischer, T. C.; Amponsah, I. K.; Pistorius, D.; Oberer, L. J. Nat. Prod. 2014, 28, 1210.
[9] Ai, W.; Wei, X.; Lin, X.; Sheng, L.; Wang, Z.; Tu, Z.; Yang, X.; Zhou, X.; Li, J.; Liu, Y. Tetrahedron 2014, 70, 5806.
[10] Pudhom, K.; Teerawatananond, T. J. Nat. Prod. 2014, 77, 1962.
[11] Pudhom, K.; Teerawatananond, T.; Chookpaiboon, S. Mar. Drugs 2014, 12, 1271.
[12] 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.
[13] Macías-Rubalcava, M. L.; Ruiz-Velasco, Sobrino, M. E.; Meléndez-González, C.; Hernández-Ortega, S. J. Agric. Food Chem. 2014, 62, 3553.
[14] 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.
[15] Li, T.-X.; Yang, M.-H.; Wang, X.-B.; Wang, Y.; Kong, L.-Y. J. Nat. Prod. 2015, 78, 2511.
[16] Bunyapaiboonsri, T.; Yoiprommarat, S.; Nopgason, R.; Intereya, K.; Suvannakad, R.; Sakayaroj, J. Tetrahedron 2015, 71, 5572.
[17] Yu, H.; Bai, H.; Mei, W.; Zuo, W.; Wang, H.; Yang, J.; Dai, H. J. Trop. Subtrop. Bot. 2015, 23, 323.
[18] Xu, Y.; Mafezoli, J.; Oliveira, M. C. F.; Jana, M. U.; Arnold, A. E.; Gunatilaka, A. A. L. J. Nat. Prod. 2015, 78, 2738.
[19] Happi, G.; Kouama, S. F.; Talontsi, F.; Zühlke, S.; Lamshöft, M.; Spiteller, M. Fitoterapia 2015, 102, 35.
[20] Jiang, H.; Ma, S.-G.; Li, Y.; Liu, Y.-B.; Li, L.; Qu, J.; Yu, S.-S. Bioorg. Med. Chem. Lett. 2016, 26, 4832.
[21] Xie, F.; Chang, W.; Zhang, M.; Li, Y.; Li, W.; Shi, H.; Zheng, S.; Lou, H. Sci. Rep. 2016, 6, 33687.
[22] Kamal, N.; Viegelmann, C. V.; Clements, C. J.; Edrada-Ebel, R. Planta Med. 2016, 83, 565.
[23] Siridechakorn, I.; Yue, Z.; Mittraphab, Y.; Lei, X.; Pudhom, K. Bioorg. Med. Chem. 2017, 25, 2878.
[24] (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.
[25] Chen, X.; Shi, Q.; Lin, G.; Guo, S.; Yang, J. J. Nat. Prod. 2009, 72, 1712.
[26] Masahiko, I.; Panida, C.; Pranee, R.; Kitlada, S.; Prasert, S.; Palangpon, K.; Samran, P. J. Antibiot. 2015, 68, 334.
[27] Chen, S.; Chen, D.; Cai, R.; Cui, H.; Long, Y.; Lu, Y.; Li, C.; She, Z. J. Nat. Prod. 2016, 79, 2397.
[28] 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.
[29] Erika, E. E. Ph.D Dissertation, University of Pittsburgh, USA, 2008.
[30] Krohn, K.; Wang, S.; Ahmed, I.; Altun, S.; Aslan, A.; Florke, U.; Kock, I.; Schlummer, S. Eur. J. Org. Chem. 2010, 4476.
[31] Wang, R.; Liu, G.; Yang, M.; Wang, M.; Zhou, L. Molecules 2016, 21, 600.
[32] Aslan, A.; Altun, S.; Ahmed, I.; Florke, U.; Schulz, B.; Krohn, K. Eur. J. Org. Chem. 2011, 1176.
[33] Murphy, A. C.; Devenish, S. R. A.; Muscroft-Taylor, A. C.; Blunt, J. W.; Munro, M. H. G. Org. Biomol. Chem. 2008, 6, 3854.
[34] Tsukamoto, H.; Hanada, S.; Kumasaka, K.; Kagaya, N.; Izumikawa, M.; Shinya, K.; Doi, T.; Org. Lett. 2016, 18, 4848.
[35] Bode, H. B.; Wegner, B.; Zeeck, A. J. Antibiot. 2000, 53, 153.
[36] Chi, S.; Heathcock, C. H. Org. Lett. 1999, 1, 3.
[37] Ai, W.; Lin, L.; Wang, Z.; Lu, X.; Mangaladoss, F.; Yang, X.; Zhou, X.; Tu, Z.; Liu, Y. J. Antibiot. 2015, 68, 213.
[38] Zhao, J.; Zheng, B.; Li, Y.; Shan, T.; Mou, Y.; Lu, S.; Li, P.; Zhou, L. Molecules 2011, 16, 847.
[39] Zhao, J.; Li, Y.; Shan, T.; Mou, Y.; Zhou, L. World J. Microbiol. Biotechnol. 2011, 27, 2753.
[40] Li, Y.; Li, P.; Mou, Y.; Zhao, J.; Shan, T.; Ding, C.; Zhou, L. World J. Microbiol. Biotechnol. 2012, 28, 1407.
[41] Mou, Y.; Meng, J.; Fu, X.; Wang, X.; Tian, J.; Wang, M.; Peng, Y.; Zhou, L. Molecules 2013, 18, 15587.
[42] Zhao, J.; Wang, X.; Sun, W.; Mou, Y.; Peng, Y.; Zhou, L. Electron. J. Biotechnol. 2013, 16, 1.
[43] Mou, Y.; Luo, H.; Mao, Z.; Shan, T.; Sun, W.; Zhou, K.; Zhou, L. Int. J. Mol. Sci. 2013, 14, 979.
[44] Li, Y.; Shan, T.; Mou, Y.; Li, P.; Zhao, J.; Zhao, W.; Peng, Y.; Zhou, L.; Ding, C. Molecules 2012, 17, 3761.
[45] Mou, Y.; Zhou, K.; Xu, D.; Yu, R.; Li, J.; Yue, Y.; Zhou, L. Nat. Prod. Res. Dev. 2015, 27, 205(in Chinese). (牟燕, 周开谊, 徐丹, 于瑞婷, 李京, 岳阳, 周立刚, 天然产物研究与开发, 2015, 27, 205.)
[46] Mou, Y.; Li, J.; Zhou, K.; Yu, R.; Xu, D.; Luo, H.; Lai, D.; Zhou, L. Trop. J. Pharm. Res. 2015, 14, 407.
[47] Mou, Y.; Xu, D.; Mao, Z.; Dong, X.; Lin, F.; Wang, A.; Lai, D.; Zhou, L.; Xie, B. Molecules 2015, 20, 20320.
[48] Mou, Y.; Zhou, K.; Xu, D.; Yu, R.; Li, J.; Yin, C.; Zhou, L. Trop. J. Pharm. Res. 2015, 14, 241.
[49] Ortega, H. E.; Teixeira, E. M.; Rabello, A.; Higginbotham, S.; Cubilla-Ríos, L. Nat. Chem. Commun. 2014, 9, 95.
[50] Chen, X.; Shi, Q.; Wang, C.; Li, B.; Wang, A.; Guo, S. Mycosys-tema 2013, 32, 729.
[51] Li, B.; Wang, C.; Chen, X.; Lyu, J.; Guo, S. J. Chromatogr. B 2013, 938, 1.
[52] Cai, X.; Shan, T.; Li, P.; Huang, Y.; Xu, L.; Zhou, L.; Wang, M.; Jiang, W. Nat. Prod. Commun. 2009, 4, 1469.
[53] Zhong L.; Wang L.; Shan T.; Liu H.; Zhao J.; Xu L.; Zhou L. Nat. Prod. Res. Dev. 2012, 24, 20(in Chinese). (钟灵允, 王兰, 单体江, 刘浩, 赵江林, 徐梁, 周立刚, 天然产物研究与开发, 2012, 24, 20.)
[54] Martinez-Luis, S.; Della-Togna, G.; Coley, P.; Kursar, T.; Gerwick, W.; Cubilla-Rios, L. J. Nat. Prod. 2008, 71, 2011.
[55] Martinez-Luis, S.; Della-Togna, G.; Coley, P.; Kursar, T.; Gerwick, W.; Cubilla-Rios, L. Rev. Latinoam. Quim. 2009, 37, 104.
[56] Dong, J.; Song, H.; Li, J.; Tang, Y.; Sun, R.; Wang, L. J. Nat. Prod. 2008, 71, 952.
[57] Zhou, Y.; Shen, K.; Dong, J.; Wang, L.; Sun, R.; Wang, C.; Wang, L. Zhang, K. Chin. J. Antibiot. 2009, 34, 74(in Chinese). (周永平, 申开泽, 董锦艳, 王利梅, 孙蓉, 王纯仁, 王乐, 张克勤, 中国抗生素杂志, 2009, 34, 74.)
[58] Tian, J.; Liu, X.; Liu, Z.; Lai, D.; Zhou, L. Pest Manage. Sci. 2016, 72, 961.
[59] 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.
[60] 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.
[61] Gocer, H.; Aslan, A.; Gulcin, I.; Supuran, C. T. J. Enzyme Inhib. Med. Chem. 2015, 31, 503.
[62] Arabaci, B.; Gulcin, I.; Alwasel, S. Molecules 2014, 19, 10103.
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