Synthesis, Biological Evaluation, and Structure-Activity Relationship Study of Unsaturated Spiroacetals as Potential Sex Attractants to Oriental Fruit Flies (Bactrocera dorsalis)

doi:10.6023/cjoc201808022

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (3): 747-753.DOI: 10.6023/cjoc201808022 Previous Articles Next Articles

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不饱和螺环缩酮的合成及对桔小实蝇(Bactrocera dorsalis)性引诱活性与构效关系研究

李九一^a, 陈立^b, 尹标林^a

a 华南理工大学化学与化工学院广东省功能分子工程重点实验室广州 510640;
b 中国科学院动物研究所农业虫害鼠害综合治理研究国家重点实验室北京 100101

收稿日期:2018-08-20 修回日期:2018-09-29 发布日期:2018-11-12
通讯作者: 尹标林 E-mail:blyin@scut.edu.cn
基金资助:
国家自然科学基金（Nos.21572068，21871094）资助项目.

Synthesis, Biological Evaluation, and Structure-Activity Relationship Study of Unsaturated Spiroacetals as Potential Sex Attractants to Oriental Fruit Flies (Bactrocera dorsalis)

Li Jiuyi^a, Chen Li^b, Yin Biaolin^a

a Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640;
b State Key Laboratory of Integrated Management of Pest Insects and Rodents, Institute of Zoology, Chinese Academy of Sciences, Beijing 100101

Received:2018-08-20 Revised:2018-09-29 Published:2018-11-12
Contact: 10.6023/cjoc201808022 E-mail:blyin@scut.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21572068, 21871094).

1. Synthesis, Biological Evaluation, and Structure-Activity Relationship Study of Unsaturated Spiroacetals as Potential Sex Attractants to Oriental Fruit Flies (Bactrocera dorsalis).PDF(1996KB)

Abstract

Spiroacetal motif is widely distributed in many bioactive natural products of different origins and essentially contributes to various bioactivities. In this paper, two series of spiroacetals were synthesized and biologically evaluated as insect sex attractant towards oriental fruit flies (Bactrocera dorsalis) using methyleugenol as the standard. Biological evaluation demonstrated that a large part of the tested compounds triggered apparent electrophysiological responses from both male and female fruit flies. The stereochemistry of the spiroacetals and the substitution on their phenyl rings influenced the responses to some degree.

Key words: spiroacetals, sex attractant, oriental fruit fly (Bactrocera dorsalis), electroantennogram response

Cite this article

Li Jiuyi, Chen Li, Yin Biaolin. Synthesis, Biological Evaluation, and Structure-Activity Relationship Study of Unsaturated Spiroacetals as Potential Sex Attractants to Oriental Fruit Flies (Bactrocera dorsalis)[J]. Chin. J. Org. Chem., 2019, 39(3): 747-753.

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[1] (a) White, I. M.; Elson-Harris, M. M. Fruit Flies of Economic Significance:Their Identification and Bionomics, CAB International, Wallingford, U. K. 1992.
(b) Clarke, A. R.; Armstrong, K. F.; Carmichael, A. E.; Milne, J. R.; Raghu, S.; Roderick, G. K.; Yeates, D. K. Annu. Rev. Entomol. 2005, 50, 293.
(c) United States Department of Agriculture Host List:Oriental Fruit Fly; Biological Assessment Support Staff, Plant Protection and Quarantine, USDAAPHIS, Hyattsville, MD, 1983.
[2] (a) Allwood, A. J.; Chinajariyawong, A.; Kritsaneepaiboon, S.; Drew, R. A. I.; Hamacek, E. L.; Hancock, D. L.; Hengsawad, C.; Jipanin, J. C.; Jirasurat, M.; Krong, C. K.; Leong, C. T. S.; Vijaysegaran, S. Raffles Bull. Zool. 1999, 47(Suppl. 7), 1.
(b) Clarke, A. R.; Allwood, A.; Chinajariyawong, A.; Drew, R. A. I.; Hengsawad, C.; Jirasurat, M.; Krong, C. K.; Kritsaneepaiboon, S.; Vijaysegaran, S. Raffles Bull. Zool. 2001, 49, 207.
(c) Ye, H.; Liu, J.-H. Insect Sci. 2005, 12, 387.
[3] Verghese, A.; Tandon, P. L.; Stonehouse, J. M. Crop Prot. 2004, 23, 61.
[4] (a) Jin, T.; Zeng, L.; Lin, Y. Y.; Lu, Y. Y.; Liang, G. W. Pest Manage. Sci. 2011, 67, 370.
(b) Hsu, J. C.; Feng, H. T.; Wu, W. J. J. Econ. Entomol. 2004, 97, 1682.
(c) Hsu, J. C.; Feng, H. T. J. Econ. Entomol. 2006, 99, 931.
(d) Zhang, R. M.; He, S. Y.; Chen, J. H. J. Econ. Entomol. 2014, 107, 1233.
[5] (a) Pan, Z. P.; Lu, Y. Y.; Zeng, L.; Zeng, X. N. Acta Entomol. Sin. 2008, 51, 609(in Chinese).
(b) Jean-Charles, B.; Thomas, B.; Dominique, B.; Benoit, S. Arch. Insect Biochem. Physiol. 2002, 51, 55.
[6] (a) Howlett, F. M. B. Entomol. Res. 1915, 6, 297.
(b) Metcalf, R. L.; Mitchell, W. C.; Fukuto, T. R.; Metcalf, E. R. Proc. Natl. Acad. Sci. U. S. A. 1975, 72, 2501.
[7] For reviews on spiroacetal-containing natural products, see:(a) Franke, W.; Kitching, W. Curr. Org. Chem. 2001, 5, 233.
(b) Jacobs, M. F.; Kitching, W. Curr. Org. Chem. 1998, 2, 395.
(c) Fletcher, M. T.; Kitching, W. Chem. Rev. 1995, 95, 789.
(d) Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617.
(e) Boivin, T. L. B. Tetrahedron 1987, 43, 3309.
[8] For reviews on the bioactivities and syntheses of spiroacetals, see:(a) Aho, J. E.; Pihko, P. M.; Rissa, T. K. Chem. Rev. 2005, 105, 4406.
(b) Mead, K. T.; Brewer, B. N. Curr. Org. Chem. 2003, 7, 227.
(c) Booth, Y. K.; Kitching, W.; De Voss, J. J. Nat. Prod. Rep. 2009, 26, 490.
[9] Francke, W.; Heemann, V.; Gerken, B.; Renwick, J. A. A.; Vité, J. P. Naturwissenschaften 1977, 64, 590.
[10] Baker, R.; Herbert, R.; Howse, P. E.; Jones, O. T.; Francke, W.; Reith, W. J. Chem. Soc., Chem. Commun. 1980, 52.
[11] Tengö, J.; Ågren, L.; Baur, B.; Isaksson, R.; Liljefors, T.; Mori, K.; König, W. A.; Francke, W. J. Chem. Ecol. 1990, 16, 429.
[12] Baker, R.; Bacon, A. J. Experientia 1985, 41, 1484.
[13] Li, J.; Peng, H.; Wang, F.; Wang, X.; Jiang, H.; Yin, B. Org. Lett. 2016, 18, 3226.
[14] Mazomenos, B. E.; Haniotakis, G. E. J. Chem. Ecol. 1985, 11, 397.
[15] Fan, J.-F.; Yin, B.-L.; Zhang, Y.-F.; Wu, Y.-L.; Wu, Y.-K. Acta Chim. Sinica 2001, 59, 1756(in Chinese). (范俊发, 尹标林, 张瑜峰, 吴毓林, 伍贻康, 化学学报, 2001, 59, 1756.)
[16] Chen, L.; Fadamiro, H. Y. J. Insect Behav. 2007, 20, 267.

不饱和螺环缩酮的合成及对桔小实蝇(Bactrocera dorsalis)性引诱活性与构效关系研究

Synthesis, Biological Evaluation, and Structure-Activity Relationship Study of Unsaturated Spiroacetals as Potential Sex Attractants to Oriental Fruit Flies (Bactrocera dorsalis)

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