Citation: Wu Qiongyou, Zhang Rui, Pan Jinhuan, Clough John, Gu Yucheng, Yang Guangfu. Design and Synthesis of Natural Product Mevalocidin Chiral Center Based Analogues[J]. Chinese Journal of Organic Chemistry, ;2018, 38(4): 840-845. doi: 10.6023/cjoc201710023 shu

Design and Synthesis of Natural Product Mevalocidin Chiral Center Based Analogues

a.
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079
b.
Syngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire RG426 EY, United Kingdom

Corresponding author: Wu Qiongyou, qywu@mail.ccnu.edu.cn Yang Guangfu, gfyang@mail.ccnu.edu.cn
Received Date: 21 October 2017
Revised Date: 24 November 2017
Available Online: 12 April 2017
Fund Project: the National Natural Science Foundation of China 21472063Project supported by the National Natural Science Foundation of China (No. 21472063)

Figures(3)

Mevalocidin is a phytotoxin, produced by two fungal isolates designated Rosellinia DA092917 and Fusarium DA056446, and has a broad spectrum of post emergence herbicidal activity at relatively high rate (4 kg/ha). Structural modification of mevalocidin at its chiral center was investigated with the aim of discovering of novel herbicides with improved activity. In order to determine the role of hydroxyl and methyl groups of mevalocidin exhibiting the herbicidal activity, we designed (±)-deoxy-mevalocidin (1) and (±)-demethyl-mevalocidin (2), respectively. These two designed compounds were synthesized (racemate) through two different synthetic approaches and characterized by ¹H NMR, ¹³C NMR and HRMS spectra. The herbicidal activities of the synthesized compounds were evaluated against both dicotyledon and monocotyledon weeds. Bioassay results indicated that the both synthesized analogues lost the herbicidal activity when compared to parent and it demonstrated that methyl and/or hydroxyl groups at the chiral center of mevalocidin are crucial for its herbicidal activity. Thus, this study will provide insights into the structural modification of mevalocidin.
- natural product,
- mevalocidin,
- chiral center,
- structural modification,
- herbicidal activity
1. [1]
  Guan, A. Y.; Liu, C. L.; Yang, X. P.; Dekeyser, M. Chem. Rev. 2014, 114, 7079. doi: 10.1021/cr4005605
2. [2]
  Hashidoko, Y.; Shinano, T. J. Pest. Sci. 2011, 36, 106. doi: 10.1584/jpestics.W10-79
3. [3]
  Jeschke, P. Pest Manage. Sci. 2010, 66, 10. doi: 10.1002/ps.v66:1
4. [4]
  Damalas, C. A.; Eleftherohorinos, I. G. Int. J. Environ. Res. Public Health 2011, 8, 1402. doi: 10.3390/ijerph8051402
5. [5]
  Duke, S. O. Pest Manage. Sci. 2012, 68, 505. doi: 10.1002/ps.2333
6. [6]
  Dayan, F. E.; Owens, D. K.; Duke, S. O. Pest Manage. Sci. 2012, 68, 519. doi: 10.1002/ps.2332
7. [7]
  Butler, M. S. J. Nat. Prod. 2004, 67, 2141. doi: 10.1021/np040106y
8. [8]
  Dayan, F. E.; Duke, S. O. Plant Physiol. 2014, 166, 1090. doi: 10.1104/pp.114.239061
9. [9]
  Zhang, Z.; Xing, A.; Staswick, P. Clemente, T. E. Plant Cell, Tissue Organ Cul. 1999, 56, 37. doi: 10.1023/A:1006298622969
10. [10]
  Bayer, E.; Gugel, K. H.; Haegele, K.; Hagenmaier, H.; Esipov, S. E.; Koenig, W. A.; Zaehner, H. Helv. Chim. Acta 1972, 55, 224. doi: 10.1002/hlca.v55:1
11. [11]
  Omura, S.; Hinotozawa, K.; Imamura, N.; Murata, M. J. Antibiot. 1984, 37, 939. doi: 10.7164/antibiotics.37.939
12. [12]
  Hoerlein, G. Rev. Environ. Contam. Toxicol. 1994, 138, 73.
13. [13]
  Mitchell, G.; Bartlett, D. W.; Fraser, T. E. M.; Hawkes, T. R.; Holt, D. C.; Townson, J. K.; Wichert, R. A. Pest Manage. Sci. 2001, 57, 120. doi: 10.1002/(ISSN)1526-4998
14. [14]
  Gerwick, B. C. ; Graupner, P. R. ; Fields, S. C. ; Schmitzer, P. R. ; Brewster, W. K. US 7393812, 2008[Chem. Abstr. 2006, 485213].
15. [15]
  Lichtner, F. Austral. J. Plant Physiol. 2000, 27, 609.
16. [16]
  Gerwick, B. C.; Brewser, W. K.; de Bore, G. J.; Fields, S. C.; Graupner, P. R.; Hahn, D. R.; Pearce, C. J.; Schmitzer, P. R.; Webster, J. D. J. Chem. Ecol. 2013, 39, 253. doi: 10.1007/s10886-013-0238-7
17. [17]
  Lin, L.; Mulholland, N.; Wu, Q. Y.; Beattie, D.; Huang, S. W.; Irwin, D.; Clough, J.; Gu, Y. C.; Yang, G. F. J. Agric. Food Chem. 2012, 60, 4480. doi: 10.1021/jf300610j
18. [18]
  Lin, L.; Mulholland, N.; Huang, S. W.; Beattie, D.; Irwin, D.; Gu, Y. C.; Clough, J.; Wu, Q. Y.; Yang, G. F. Chem. Biol. Drug Des. 2012, 80, 682. doi: 10.1111/jpp.2012.80.issue-5
19. [19]
  Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208. doi: 10.1021/ja993349z
20. [20]
  Villieras, J.; Rambaud, M. Synth. Commun. 1983, 300.
21. [21]
  Suizu, H.; Shigeoka, D.; Aoyama, H.; Yoshimitsu, T. Org. Lett. 2015, 17, 126. doi: 10.1021/ol503356m
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1.
沈阳化工大学材料科学与工程学院沈阳 110142