Effect of drimenol and synthetic derivatives on growth and germination of Botrytis cinerea : Evaluation of possible mechanism of action

Robles-Kelly, Christian; Rubio, Julia; Thomas, Mario; Sedán, Claudia; Martínez, Rolando; Olea, Andrés F.; Carrasco, Héctor; Taborga, Lautaro; Silva-Moreno, Evelyn

doi:10.1016/j.pestbp.2016.11.006

Cited by 20 publications

(31 citation statements)

References 35 publications

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“…In Figure 2 B, the percentage of inhibition of hyphal growth is shown at different polygodial concentrations. The results indicate that polygodial reduces the B. cinerea mycelium growth by nearly 50% after two days of incubation at 80 and 160 ppm, and an EC 50 value of 117 ppm has been obtained, which is higher than those reported for drimenol and its derivatives (80 ppm) and for a commercial natural fungicide, BC-1000 (30 ppm) [ 19 ].…”

Section: Resultsmentioning

confidence: 99%

“…In the same way, the effect of polygodial on reactive oxygen species (ROS) production was examined by incubating B. cinerea conidia in the presence of polygodial for 2 h at 21 °C. The production of ROS was evaluated using ROS-Glo™ H 2 O 2 Assay as described by Robles-Kelly et al [ 19 ]. In Figure 7 are shown the luminescence yields measured in presence of polygodial (100 ppm), drimenol (80 ppm) and menadione that is used as positive control.…”

Section: Resultsmentioning

confidence: 99%

“…However, a recent study carried out on a group of sesquiterpenes and derivatives indicates that the presence of the Δ 7,8 -double bond is necessary for the activity against yeast, even though the activity is much higher when this double bond is forming part of the C-8 α,β-unsaturated aldehyde moiety [ 18 ]. Recently, we have shown that the presence of the ∆ 7,8 -double bond in drimenol ( Figure 1 ) and its derivatives is critical for antifungal activity against B. cinerea [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

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Antifungal Effect of Polygodial on Botrytis cinerea, a Fungal Pathogen Affecting Table Grapes

Carrasco

Robles-Kelly

Rubio

et al. 2017

IJMS

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The antifungal activity of polygodial, a secondary metabolite extracted from Canelo, on mycelial growth of different Botrytis cinerea isolates has been evaluated. The results show that polygodial affects growth of normal and resistant isolates of B. cinerea with EC50 values ranging between 117 and 175 ppm. In addition, polygodial markedly decreases the germination of B. cinerea, i.e., after six hours of incubation the percentage of germination decreases from 92% (control) to 25% and 5% in the presence of 20 ppm and 80 ppm of polygodial, respectively. Morphological studies indicate that conidia treated with polygodial are smaller, with irregular membrane border, and a lot of cell debris, as compared to conidia in the control. The existence of polygodial-induced membrane damage was confirmed by SYTOX® Green uptake assay. Gene expression studies confirm that the effect of polygodial on B. cinerea is mainly attributed to inhibition of germination and appears at early stages of B. cinerea development. On the other hand, drimenol, a drimane with chemical structure quite similar to polygodial, inhibits the mycelial growth efficiently. Thus, both compounds inhibit mycelial growth by different mechanisms. The different antifungal activities of these compounds are discussed in terms of the electronic density on the double bond.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Antifungal Effect of Polygodial on Botrytis cinerea, a Fungal Pathogen Affecting Table Grapes

Carrasco

Robles-Kelly

Rubio

et al. 2017

IJMS

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“…Molecule 1 is a natural product presents in liverworts and higher plants (44, 45), and its antifungal mechanism against human pathogenic fungi has not been reported previously. A recent study has shown that 1 has antifungal activity against Botrytis cinerea , a plant fungal pathogen and the mechanisms appear to act by fungal membrane damage and reactive oxygen species (ROS) production (46).…”

Section: Discussionmentioning

confidence: 99%

Broad-Spectrum Antifungal Activities and Mechanism of Drimane Sesquiterpenoids

Edouarzin

Horn

Paduyal

et al. 2019

Preprint

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25Eight drimane sesquiterpenoids including (-)-drimenol and (+)-albicanol were synthesized 26 from (+)-sclareolide and evaluated for their antifungal activities. Three compounds, (-)-drimenol, 27 (+)-albicanol, and (1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-decahydronaphthalene-1-28 carbaldehyde (4) showed strong activity against C. albicans. (-)-Drimenol, the strongest inhibitor 29 of the three, (at concentrations of 8 -64 g/ml, causing 100% death of fungi), acts not only against 30 C. albicans as a fungicidal manner, but also inhibits other fungi such as Aspergillus, Cryptococcus, 31 Pneumocystis, Blastomyces, Fusarium, Rhizopus, Saksenaea and FLU resistant strains of C. 32 albicans, C. glabrata, C. krusei, C. parapsilosis and C. auris. These observations suggest drimenol 33 is a broad-spectrum antifungal agent. At high concentration (100 μg/ml), drimenol caused a 34 rupture of the fungal cell wall/membrane. In a nematode model of C. albicans infection, drimenol 35 rescued the worms from C. albicans-mediated death, indicating drimenol is tolerable and bioactive 36 in a metazoan. Genome-wide fitness profiling assays of both S. cerevisiae (nonessential 37 homozygous and essential heterozygous) and C. albicans (Tn-insertion mutants) collections 38 revealed putative genes and pathways affected by drimenol. Using a C. albicans mutants spot 39 assay, the Crk1 kinase associated gene products, Ret2, Cdc37, and novel putative targets 40 orf19.759, orf19.1672, and orf19.4382 were revealed to be the potential targets of drimenol. 41 Further, computational modeling results suggest possible modification of the structure of drimenol 42 including the A ring for improving antifungal activity. 43 44 45 46 47 48 Life-threatening fungal infections are an important cause of morbidity and mortality, 49 particularly for patients with immune deficiency and those who are undergoing chemotherapeutic 50 treatments. Some of the leading invasive fungal pathogens include Candida sp., Aspergillus sp. 51 and Cryptococcus sp. Currently, the antifungal therapeutic options are limited, especially when 52 compared to available antibacterial agents (1-4). Among the five classes of antifungals, azoles, 53 echiocandins, polyenes, allylamines, and pyrimidine derivatives, only three are used clinically; 54 azoles, echiocandins, and polyenes. Azole drugs, such as fluconazole (FLU), inhibit ergosterol 55 synthesis through inhibition of lanosterol 14--demethylase, impairing formation of the fungal 56 cell wall. Echocandins, such as caspofungin (CAS), block 1,3--glucan synthase and lead to 57 depletion of glucan in fungal cell wall. Polyenes, including amphotericin B (AMB), bind to 58 ergosterol in fungal cell membrane and change the cell membrane transition temperature, resulting 59 in leakage of ions and small organic molecules, and eventual cell death. Allylamines, such as 60 amorolfin, affect ergosterol synthesis by inhibition of squalene epoxidase. Pyrimidines, such as 61 flucytosine (or 5-fluorocytosine), block nucleic acid synthesis,...

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“…These terpenes have antifungal properties against Gaeumannomyces graminis fungus, a causal agent of infection in wheat [58]. Furthermore, polygodial and drimenol terpenes isolated from canelo have shown to have antifungal activity against Botrytis cinerea, the causal agent of infection in table grape [59,60]. (Figure 8), isolated from the resinous exudate Eupatorium salvia leaves (salvia macho), in vitro, inhibit the mycelial growth of B. cinerea [61].…”

Section: Active Compounds Obtained From Plantsmentioning

confidence: 99%

Natural Compounds: A Sustainable Alternative to the Phytopathogens Control

Jiménez-Reyes¹,

Carrasco

Olea

et al. 2019

J. Chil. Chem. Soc.

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Fungi are the primary infectious agents in plants causing significant economic losses in agroindustry. Traditionally, these pathogens have been treated with different synthetic fungicides such as hydroxianilides, anilinopyrimidines, and azoles, to name a few. However, the indiscriminate use of these chemicals has increased fungi resistance in plants. Natural products have been researched as a control, and an alternative to these synthetic fungicides since they are not harmful to health and contribute to the environment caring. This review describes plants extracts, essential oils, and active compounds or secondary metabolites as antifungal agents both, in vitro and in vivo. Active compounds have been recently described as the best candidates for the control of phytopathogenic fungi. When metabolized by plants, these compounds concentrations rely on the environmental conditions and pathogens incidence. However, one issue regarding the direct application of these preformed compounds in plants touch upon their low persistence in the environment, and their even lower bioavailability than synthetic fungicides. Hence the challenge is to develop useful formulations based on natural products to increase the compounds solubility facilitating thus their application in the field while maintaining their properties.

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Effect of drimenol and synthetic derivatives on growth and germination of Botrytis cinerea : Evaluation of possible mechanism of action

Cited by 20 publications

References 35 publications

Antifungal Effect of Polygodial on Botrytis cinerea, a Fungal Pathogen Affecting Table Grapes

Antifungal Effect of Polygodial on Botrytis cinerea, a Fungal Pathogen Affecting Table Grapes

Broad-Spectrum Antifungal Activities and Mechanism of Drimane Sesquiterpenoids

Natural Compounds: A Sustainable Alternative to the Phytopathogens Control

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