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Biomass Chemical Engineering ›› 2021, Vol. 55 ›› Issue (1): 49-55.doi: 10.3969/j.issn.1673-5854.2021.01.007

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Quantitative Structure-activity Relationship Analysis of Citral-based Antifungal Derivatives Against Colletotrichum gloeosporioides

Rong ZENG1, Hongyan SI1, Shangxing CHEN1, Jie SONG2, Zongde WANG1, Shengliang LIAO1,*()   

  1. 1. College of Forestry, Jiangxi Agricultural University, East China Woody Fragrance and Flavor Engineering Technology Research Center of National Forestry and Grassland Administration, Nanchang 330045, China
    2. Department of Chemistry and Biochemistry, University of Michigan-Flint, Flint MI 48502, USA
  • Received:2020-07-15 Online:2021-01-30 Published:2021-01-25
  • Contact: Shengliang LIAO E-mail:liaosl@jxau.edu.cn


In order to investigate the relationship between the structure of citral derivatives and their antifungal activities against Colletotrichum gloeosporioides, the quantitative structure-activity relationship study of citral-based derivatives against C. gloeosporioides was carried out. The computational chemistry softwares GaussView 05, Gaussian 09W, Ampac and Codessa were used to finish the molecular structure optimization, descriptor calculation and screening, and QSAR model construction. The results showed that the best QSAR model with four descriptors, including Min e-e repulsion for a H atom; ESP-FPSA-3 Fractional PPSA(PPSA-3/TMSA); number of H atoms; WPSA-3 Weighted PPSA(PPSA-3*TMSA/1000), were established, and its correlation coefficient (R2) was 0.926 5. Internal validation and external validation of the best QSAR model were carried out. The result of the leave-one-out internal validation was RCV2=0.865 7, the results of the three-fold internal validation were Rtraining2=0.879 3, Rtest2=0.882 4, and the result of external validation was Rext2=0.946 7. These results indicated that the best QSAR model exhibited good stability and predictability. Analysis of the modeling descriptors indicated that the descriptors related to hydrogen bond donors in the molecular structure of citral-based derivatives had a significant effect on antifungal activity against C. gloeosporioides. This study can provide theoretical guidance for the design of citral-based derivatives with better antifungal activity against C. gloeosporioides.

Key words: citral, derivatives, quantitative structure-activity relationship (QSAR), heuristic regression

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