Asymmetric preparation of antifungal 1-(4′-chlorophenyl)-1-cyclopropyl methanol and 1-(4′-chlorophenyl)-2-phenylethanol. Study of the detoxification mechanism by Botrytis cinerea

Pinedo-Rivilla, Cristina; Bustillo, Antonio; Hernández-Galán, Rosario; Aleu, Josefina; Collado, Isidro G.

doi:10.1016/j.molcatb.2011.02.005

Cited by 9 publications

(5 citation statements)

References 22 publications

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“…The most active compounds (5 and 10) were also tested by the poisoned food technique [71,36], obtaining similar results to the previous micro-dilution data (Figures S28 and S29). The most active compounds (5 and 10) were also tested by the poisoned food technique [36,71], obtaining similar results to the previous micro-dilution data (Figures S28 and S29).…”

Section: Antifungal Assaysupporting

confidence: 82%

Bio-Guided Isolation of New Compounds from Baccharis spp. as Antifungal against Botrytis cinerea

et al. 2022

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Baccharis genus Asteraceae is widely used in traditional treatment against fever, headache, hepatobiliary disorders, skin ulcers, diabetes, and rheumatism, as well as an antispasmodic and diuretic. Its phytochemistry mainly shows the presence of flavonoids and terpenoids such as monoterpenes, sesquiterpenes, diterpenes, and triterpenes. Some of them have been evaluated for biological activities presenting allelopathic, antimicrobial, cytotoxic, and anti-inflammatory properties. In this paper, our research group reported the isolation, characterization, and antifungal evaluation of several molecules isolated from the dichloromethane extract from Baccharis prunifolia, Baccharis trinervis, and Baccharis zumbadorensis against the phytopathogen fungus Botrytis cinerea. The isolated compounds have not previously been tested against Botrytis, revealing an important source of antifungals in the genus Baccharis. Six known flavones were isolated from B. prunifolia. The dichloromethane extracts of B. trinervis and B. zumbadorensis were subjected to a bio-guided isolation, obtaining three known flavones, an α-hydroxidihydrochalcone mixture, one labdane, one triterpene, and two norbisabolenes from the most active fractions. The compounds 4′-methoxy-α-hydroxydihydrochalcone (7A), 3β,15-dihydroxylabdan-7-en-17-al (8), and 13-nor-11,12-dihydroxybisabol-2-enone (11) are novel. The most active compounds were the Salvigenin (5) and 1,2-dihydrosenedigital-2-one (10) with an IC50 of 13.5 and 3.1 μg/mL, respectively.

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Section: Antifungal Assaysupporting

confidence: 82%

Bio-Guided Isolation of New Compounds from Baccharis spp. as Antifungal against Botrytis cinerea

et al. 2022

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“…So far, it was known that B. cinerea is able to modify compounds from toxic to products with lower toxicity through enzymes, such as hydroxylases, epoxidases, or reductases [8,26,27,28,29]. Hargreavfs et al [30] reported that B. cinerea was able to reduce the carbonyl group present in the phytoalexin wierona acid after three days of incubation [30].…”

Section: Resultsmentioning

confidence: 99%

Detoxification Mechanism of 8,8-Dimethyl-3-[(R-phenyl)amino]-1,4,5(8H)-naphthalentrione Derivatives by Botrytis cinerea

et al. 2019

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The effect of 8,8-dimethyl-3-[(R-phenyl)amino]-1,4,5(8H)-naphthalentrione derivatives (compounds 1–13) on the mycelial growth of Botrytis cinerea was evaluated. The fungitoxic effect depended on the substituent and its position in the aromatic ring. Compounds substituted with halogens in meta and/or para positions (compounds 3, 4, 5 and 7), methyl (compounds 8 and 9), methoxyl (compounds 10 and 11), or ethoxy-carbonyl groups (compound 12) presented higher antifungal activity than compound 1, which had an unsubstituted aromatic ring. In addition, compounds with halogens in the ortho position, such as compounds 2 and 6, and a substitution with an acetyl group in the para position (compound 13) were less active. The role of the ABC efflux pump Bctr B-type as a defense mechanism of B. cinerea against these naphthalentrione derivatives was analyzed. This pump could be involved in the detoxification of compounds 2, 6, and 13. On the contrary, this mechanism would not participate in the detoxification of compounds 1, 7, 9 and 12. Finally, the biotransformation of compound 7 by B. cinerea was studied. A mixture of two biotransformed products was obtained. One of them was compound 7A, which is reduced at C1 and C4, compared to compound 7. The other product of biotransformation, 7B, is oxidized at C7.

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“…Baker's yeast is commonly used in the successful reduction of a variety of carbonyl compounds into optically active alcohols with S-configurations [4,[20][21][22][23].…”

Section: Baker's Yeast Reductionmentioning

confidence: 99%

Biocatalytic Preparation of Chloroindanol Derivatives. Antifungal Activity and Detoxification by the Phytopathogenic Fungus Botrytis cinerea

Pinedo-Rivilla

Moraga

Pérez-Sasián

et al. 2020

Plants

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Indanols are a family of chemical compounds that have been widely studied due to their broad range of biological activity. They are also important intermediates used as synthetic precursors to other products with important applications in pharmacology. Enantiomerically pure chloroindanol derivatives exhibiting antifungal activity against the phytopathogenic fungus Botrytis cinerea were prepared using biocatalytic methods. As a result of the biotransformation of racemic 6-chloroindanol (1) and 5-chloroindanol (2) by the fungus B. cinerea, the compounds anti-(+)-6-chloroindan-1,2-diol (anti-(+)-7), anti-(+)-5-chloroindan-1,3-diol (anti-(+)-8), syn-(+)-5-chloroindan-1,3-diol (syn-(+)-8), syn-(-)-5-chloroindan-1,3-diol (syn-(-)-8), and anti-(+)-5-chloroindan-1,2-diol (anti-(+)-9) were isolated for the first time. These products were characterized by spectroscopic techniques and their enantiomeric excesses studied by chromatographic techniques. The results obtained in the biotransformation seem to suggest that the fungus B. cinerea uses oxidation reactions as a detoxification mechanism.

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Asymmetric preparation of antifungal 1-(4′-chlorophenyl)-1-cyclopropyl methanol and 1-(4′-chlorophenyl)-2-phenylethanol. Study of the detoxification mechanism by Botrytis cinerea

Cited by 9 publications

References 22 publications

Bio-Guided Isolation of New Compounds from Baccharis spp. as Antifungal against Botrytis cinerea

Bio-Guided Isolation of New Compounds from Baccharis spp. as Antifungal against Botrytis cinerea

Detoxification Mechanism of 8,8-Dimethyl-3-[(R-phenyl)amino]-1,4,5(8H)-naphthalentrione Derivatives by Botrytis cinerea

Biocatalytic Preparation of Chloroindanol Derivatives. Antifungal Activity and Detoxification by the Phytopathogenic Fungus Botrytis cinerea

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