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. 2021 Jul 26;10(8):1527.
doi: 10.3390/plants10081527.

Activity of Anthracenediones and Flavoring Phenols in Hydromethanolic Extracts of Rubia tinctorum against Grapevine Phytopathogenic Fungi

Natalia Langa-Lomba  1   2 , Eva Sánchez-Hernández  3 , Laura Buzón-Durán  3 , Vicente González-García  2 , José Casanova-Gascón  1 , Jesús Martín-Gil  3 , Pablo Martín-Ramos  1
Affiliations

Activity of Anthracenediones and Flavoring Phenols in Hydromethanolic Extracts of Rubia tinctorum against Grapevine Phytopathogenic Fungi

Natalia Langa-Lomba et al. Plants (Basel). .

Abstract

In this work, the chemical composition of Rubia tinctorum root hydromethanolic extract was analyzed by GC-MS, and over 50 constituents were identified. The main phytochemicals were alizarin-related anthraquinones and flavoring phenol compounds. The antifungal activity of this extract, alone and in combination with chitosan oligomers (COS) or with stevioside, was evaluated against the pathogenic taxa Diplodia seriata, Dothiorella viticola and Neofusicoccum parvum, responsible for the so-called Botryosphaeria dieback of grapevine. In vitro mycelial growth inhibition tests showed remarkable activity for the pure extract, with EC50 and EC90 values as low as 66 and 88 μg·mL-1, respectively. Nonetheless, enhanced activity was attained upon the formation of conjugate complexes with COS or with stevioside, with synergy factors of up to 5.4 and 3.3, respectively, resulting in EC50 and EC90 values as low as 22 and 56 μg·mL-1, respectively. The conjugate with the best performance (COS-R. tinctorum extract) was then assayed ex situ on autoclaved grapevine wood against D. seriata, confirming its antifungal behavior on this plant material. Finally, the same conjugate was evaluated in greenhouse assays on grafted grapevine plants artificially inoculated with the three aforementioned fungal species, resulting in a significant reduction in the infection rate in all cases. This natural antifungal compound represents a promising alternative for developing sustainable control methods against grapevine trunk diseases.

Keywords: Botryosphaeriaceae; GTDs; Vitis vinifera; antifungal; chitosan; madder; stevioside.

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Conflict of interest statement

The authors declare no conflict of interest. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript, or in the decision to publish the results.

Figures

Figure 1
Figure 1
(a) Structures of different anthracenediones and phenols; (b) structures of alizarin-3-O-β-primeveroside, 3; lucidin-3-O-β-primeveroside, 1; and their aglycons (alizarin, 4; lucidin, 2). Glc, D-glucose; xyl, D-xylose.
Figure 2
Figure 2
Colony growth measures of (a) D. seriata, (b) D. viticola and (c) N. parvum strains when cultured in PDA plates containing the various control products (viz. chitosan oligomers (COS), stevioside, R. tinctorum hydromethanolic extract, stevioside−R. tinctorum and COS-R. tinctorum conjugate complexes) at concentrations in the 62.5−1500 and 15.62−250 μg·mL−1 range ordered according to the least and the most active products, respectively. The same letters above concentrations indicate that they are not significantly different at p < 0.05. Error bars represent standard deviations.
Figure 2
Figure 2
Colony growth measures of (a) D. seriata, (b) D. viticola and (c) N. parvum strains when cultured in PDA plates containing the various control products (viz. chitosan oligomers (COS), stevioside, R. tinctorum hydromethanolic extract, stevioside−R. tinctorum and COS-R. tinctorum conjugate complexes) at concentrations in the 62.5−1500 and 15.62−250 μg·mL−1 range ordered according to the least and the most active products, respectively. The same letters above concentrations indicate that they are not significantly different at p < 0.05. Error bars represent standard deviations.
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References

    1. Qiu H., Liu R., Long L. Analysis of chemical composition of extractives by acetone and the chromatic aberration of teak (Tectona Grandis L.F.) from China. Molecules. 2019;24:1989. doi: 10.3390/molecules24101989. - DOI - PMC - PubMed
    1. Murdock K.C., Child R.G., Fabio P.F., Angier R.D., Wallace R.E., Durr F.E., Citarella R.V. Antitumor agents. 1. 1,4-Bis[(aminoalkyl)amino]-9,10-anthracenediones. J. Med. Chem. 1979;22:1024–1030. doi: 10.1021/jm00195a002. - DOI - PubMed
    1. Coufal N., Farnaes L. Anthracyclines and anthracenediones. In: Minev B., editor. Cancer Management in Man: Chemotherapy, Biological Therapy, Hyperthermia and Supporting Measures. Springer; Dordrecht, The Netherlands: 2011. pp. 87–102. - DOI
    1. Wuthi-udomlert M., Kupittayanant P., Gritsanapan W. In vitro evaluation of antifungal activity of anthraquinone derivatives of Senna alata. J. Health Res. 2010;24:117–122.
    1. Agarwal S., Singh S.S., Verma S., Kumar S. Antifungal activity of anthraquinone derivatives from Rheum emodi. J. Ethnopharmacol. 2000;72:43–46. doi: 10.1016/S0378-8741(00)00195-1. - DOI - PubMed

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