Synthesis and in Vitro Antifungal Activity against Botrytis cinerea of Geranylated Phenols and Their Phenyl Acetate Derivatives

Chávez, Marı́a Isabel; Soto, Mauricio; Taborga, Lautaro; Díaz, Katy; Olea, Andrés F.; Bay, Camila; Peña‐Cortés, Hugo; Espinoza, Luis

doi:10.3390/ijms160819130

Cited by 10 publications

(31 citation statements)

References 18 publications

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“…Linear geranylated phenols/methoxyphenols have been synthesized by direct coupling of geraniol with the respective phenol or methoxyphenols. This reaction has been studied for many authors, because it is directly related to the synthesis of biologically-active phenolic terpenoids [ 11 , 14 , 20 , 26 , 27 , 28 , 29 , 30 ]. The coupling is commonly carried out in strong mineral acids or aprotic solvents with Lewis acids, e.g., BF 3 ·Et 2 O, in dioxane for the synthesis of tocopherols and geranyl and farnesyl analogs of the ubiquinones, p -toluenesulfonic acid in CH 2 CI 2 for the synthesis of cannabigerol and related marihuana constituents [ 39 ].…”

Section: Resultsmentioning

confidence: 99%

“…The coupling is commonly carried out in strong mineral acids or aprotic solvents with Lewis acids, e.g., BF 3 ·Et 2 O, in dioxane for the synthesis of tocopherols and geranyl and farnesyl analogs of the ubiquinones, p -toluenesulfonic acid in CH 2 CI 2 for the synthesis of cannabigerol and related marihuana constituents [ 39 ]. Alternatively, BF 3 ·Et 2 O/AgNO 3 has been used as a catalyst and acetonitrile as a solvent [ 29 , 30 ]. In this work, Compounds 1 , 3 , 14 , 15 , 17 and 19 were synthesized through this reaction, using dioxane as the solvent, BF 3 ·Et 2 O as the catalyst and in the presence or absence of a nitrogen atmosphere.…”

Section: Resultsmentioning

confidence: 99%

“…Thus, the interesting biological activity shown by 1 and other prenyl derivatives [ 17 ] (see Figure 1 ) has prompted us to undertake the synthesis of a significant number of linear geranylated phenols, including Compounds 1 – 3 and some geranylated methoxyphenyl/acetate analogs [ 26 , 27 , 28 , 29 , 30 , 31 , 32 ], in order to evaluate the in vitro cytotoxic activity on some cancer lines and the inhibitory effects on the mycelial growth of plant pathogen Botrytis cinerea [ 29 , 30 , 31 ]. The latter is a facultative phytopathogenic fungus that attacks the flowers, fruits, leaves and stems of more than 200 plant species [ 33 ].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of New Hydrated Geranylphenols and in Vitro Antifungal Activity against Botrytis cinerea

Soto

Espinoza

Chávez

et al. 2016

IJMS

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Geranylated hydroquinones and other geranylated compounds isolated from Aplydium species have shown interesting biological activities. This fact has prompted a number of studies where geranylated phenol derivatives have been synthesized in order to assay their bioactivities. In this work, we report the synthesis of a series of new hydrated geranylphenols using two different synthetic approaches and their inhibitory effects on the mycelial growth of Botrytis cinerea. Five new hydrated geranylphenols were obtained by direct coupling reaction between geraniol and phenol in dioxane/water and using BF3·Et2O as the catalyst or by the reaction of a geranylated phenol with BF3·Et2O. Two new geranylated quinones were also obtained. The synthesis and structural elucidation of all new compounds is presented. All hydrated geranylphenols efficiently inhibit the mycelial growth of B. cinerea. Their activity is higher than that observed for non-hydrated compounds. These results indicate that structural modification on the geranyl chain brings about an enhancement of the inhibition effect of geranylated phenol derivatives.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of New Hydrated Geranylphenols and in Vitro Antifungal Activity against Botrytis cinerea

Soto

Espinoza

Chávez

et al. 2016

IJMS

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“…The antifungal activity against B. cinerea of these geranylphenol was higher when the number of methoxy groups increased (Chávez et al . ). On the other hand, the antifungal activity against B. cinerea of the alkaloids flindersine and haplamine was analysed.…”

Section: Resultsmentioning

confidence: 97%

Characterization of the fungitoxic activity onBotrytis cinereaof the aristolochic acids I andII

Melo

Sanhueza

Mendoza

et al. 2018

Lett Appl Microbiol

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Significance and Impact of the Study: The fungitoxic effect on Botrytis cinerea of aristolochic acids I and II was characterized. The only structural difference among these compounds is a methoxy group at carbon 8. However, despite their structural similarity, the fungitoxic effect of aristolochic acid I was higher than the effect of aristolochic acid II. This result suggests that the methoxy group is important for the fungitoxic activity of these compounds on B. cinerea. AbstractThe fungitoxic effect of aristolochic acids I and II on mycelial growth and conidial germination of Botrytis cinerea was analysed. Aristolochic acid I had a higher effect on mycelial growth of B. cinerea than aristolochic acid II with IC 50 value of 18Á7 and 57Á0 lg ml À1 , respectively. These compounds did not affect the conidia germination. Also, the effect of both compounds on DNA and plasmatic membrane integrity of B. cinerea was studied. Only aristolochic acid II was able to cause damage to the integrity of the plasmatic membrane. When the fungus was incubated with a mixture of these compounds, degradation of DNA was observed. Finally, biotransformation products were not detected in the culture broth when B. cinerea was incubated in the presence of the aristolochic acids. Studies of structural characteristics that increase the antifungal effect of compounds against B. cinerea will permit to design new molecules to control this phytopathogenic fungus.

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“…Other synthetic geranylphenols, such as 2-geranyl-5methyl resorcinol and 4-geranyl-5-methyl resorcinol ( Figure 1A), showed antimicrobial and antifungal activities [16][17][18][19] . Recently, our research group has developed the synthesis, structural determination and antifungal activity of a series of linear geranylphenols derivatives of 2-geranylhydroquinones, such 2-geranylphloroglucinol ( Figure 1A) [20][21][22][23][24][25][26] .…”

Section: Linearmentioning

confidence: 99%

Cytotoxic Effect of Geranylphenol Derivatives in the Human Breast Cancer Cell Line MDA-MB-231 and Gastric Cancer Cell Line MKN74

Espinoza

Taborga

Araya

et al. 2020

Bangladesh J Med Sci

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Background: Previous studies have demonstrated that geranyl metabolites, found mainly in marine organisms, exhibit interesting antimicrobial and antifungal activities. In addition, linear geranyl derivatives have been synthesized as drugs and reported cytotoxic and anticancer activities. Aims: Considering the biological testing and the structural features of these compounds, we evaluated seven linear geranylphenol derivatives on the human breast cancer cell line MDA-MB-231, and the human gastric cancer cell line MKN74. Results: We found that compounds 2, 5 and 7 were cytotoxic for both cancer cell lines. From them, the most potent was compound 2, with an IC50=7.5 μM for MKN74 cells, and compound 7, with an IC50=14.73 μM for MDA-MB-231 cells. By nuclear staining and inmunocytochemistry, we detected that the three compounds induced cell death, and by Western blot analysis, we observed a remarkable decrease in the expression of cyclin D1 and the retinoblastoma protein, key regulators of the cell cycle. Conclusion: Considering that compounds 2 and 7 were the most potent compounds inducing cell death, and were able to decrease the expression of retinoblastoma protein and cyclin D1, proteins usually altered in different types of cancers, they appear as promising therapeutic agents against cancer. Bangladesh Journal of Medical Science Vol.19(3) 2020 p.486-500

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Synthesis and in Vitro Antifungal Activity against Botrytis cinerea of Geranylated Phenols and Their Phenyl Acetate Derivatives

Cited by 10 publications

References 18 publications

Synthesis of New Hydrated Geranylphenols and in Vitro Antifungal Activity against Botrytis cinerea

Synthesis of New Hydrated Geranylphenols and in Vitro Antifungal Activity against Botrytis cinerea

Characterization of the fungitoxic activity onBotrytis cinereaof the aristolochic acids I andII

Cytotoxic Effect of Geranylphenol Derivatives in the Human Breast Cancer Cell Line MDA-MB-231 and Gastric Cancer Cell Line MKN74

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