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Citation: 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]. Chinese Journal of Organic Chemistry, ;2019, 39(3): 747-753. doi: 10.6023/cjoc201808022 shu

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

Corresponding author: Yin Biaolin, blyin@scut.edu.cn
Received Date: 20 August 2018
Revised Date: 29 September 2018
Available Online: 11 March 2018
Fund Project: the National Natural Science Foundation of China 21572068Project supported by the National Natural Science Foundation of China (Nos. 21572068, 21871094)the National Natural Science Foundation of China 21871094

Figures(1)

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.
- spiroacetals,
- sex attractant,
- oriental fruit fly (Bactrocera dorsalis),
- electroantennogram response
1. [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, USDA-APHIS, Hyattsville, MD, 1983.
2. [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. [3]
  Verghese, A.; Tandon, P. L.; Stonehouse, J. M. Crop Prot. 2004, 23, 61. doi: 10.1016/S0261-2194(03)00087-5
4. [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. [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. [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. [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. [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. [9]
  Francke, W.; Heemann, V.; Gerken, B.; Renwick, J. A. A.; Vité, J. P. Naturwissenschaften 1977, 64, 590. doi: 10.1007/BF00450651
10. [10]
  Baker, R.; Herbert, R.; Howse, P. E.; Jones, O. T.; Francke, W.; Reith, W. J. Chem. Soc., Chem. Commun. 1980, 52.
11. [11]
  Tengö, J.; Ågren, L.; Baur, B.; Isaksson, R.; Liljefors, T.; Mori, K.; König, W. A.; Francke, W. J. Chem. Ecol. 1990, 16, 429. doi: 10.1007/BF01021775
12. [12]
  Baker, R.; Bacon, A. J. Experientia 1985, 41, 1484.
13. [13]
  Li, J.; Peng, H.; Wang, F.; Wang, X.; Jiang, H.; Yin, B. Org. Lett. 2016, 18, 3226. doi: 10.1021/acs.orglett.6b01472
14. [14]
  Mazomenos, B. E.; Haniotakis, G. E. J. Chem. Ecol. 1985, 11, 397. doi: 10.1007/BF01411425
15. [15]
  Fan, J.-F.; Yin, B.-L.; Zhang, Y.-F.; Wu, Y.-L.; Wu, Y.-K. Acta Chim. Sinica 2001, 59, 1756(in Chinese).
16. [16]
  Chen, L.; Fadamiro, H. Y. J. Insect Behav. 2007, 20, 267. doi: 10.1007/s10905-007-9079-y
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