Medicarpin, an antifungal compound identified in hexane extract of Dalbergia congestiflora Pittier heartwood

Martínez-Sotres, Carmen; López-Albarrán, Pablo; Cruz-de-León, José; García-Moreno, Teresa; Rutiaga-Quiñones, José Guadalupe; Vázquez-Marrufo, Gerardo; Tamariz-Mascarúa, Joaquín; Herrera-Bucio, Rafael

doi:10.1016/j.ibiod.2011.11.016

Cited by 33 publications

(18 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Factors affecting laccase activity were identified as the following: heavy metals, chelating agents, halides, ionic strength, organic solvents, and surfactants. Inorganic species such as hydrogen peroxide [67], bases [68], and organic inhibitors such as dipeptides [69], β-mercaptoethanol [70] as well as hardly available natural compounds such high-molecular-weight humic acids [71], ptilomycalin A [72], and medicarpin [73,74] complete the above list. To the best of our knowledge, only the semi-synthetic hydrazide-hydrazone ether derivative of coumarin and gentisaldehyde (2,5-dihydroxybenzaldehyde) [41] is known to inhibit laccase, with a mixed type of inhibition (K iu = 35 µM and K ic = 490 µM).…”

Section: Kinetic Studiesmentioning

confidence: 99%

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

et al. 2020

View full text Add to dashboard Cite

A series of hydrazide-hydrazones 1–3, the imine derivatives of hydrazides and aldehydes bearing benzene rings, were screened as inhibitors of laccase from Trametes versicolor. Laccase is a copper-containing enzyme which inhibition might prevent or reduce the activity of the plant pathogens that produce it in various biochemical processes. The kinetic and molecular modeling studies were performed and for selected compounds, the docking results were discussed. Seven 4-hydroxybenzhydrazide (4-HBAH) derivatives exhibited micromolar activity Ki = 24–674 µM with the predicted and desirable competitive type of inhibition. The structure–activity relationship (SAR) analysis revealed that a slim salicylic aldehyde framework had a pivotal role in stabilization of the molecules near the substrate docking site. Furthermore, the presence of phenyl and bulky tert-butyl substituents in position 3 in salicylic aldehyde fragment favored strong interaction with the substrate-binding pocket in laccase. Both 3- and 4-HBAH derivatives containing larger 3-tert-butyl-5-methyl- or 3,5-di-tert-butyl-2-hydroxy-benzylidene unit, did not bind to the active site of laccase and, interestingly, acted as non-competitive (Ki = 32.0 µM) or uncompetitive (Ki = 17.9 µM) inhibitors, respectively. From the easily available laccase inhibitors only sodium azide, harmful to environment and non-specific, was over 6 times more active than the above compounds.

show abstract

Section: Kinetic Studiesmentioning

confidence: 99%

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

et al. 2020

View full text Add to dashboard Cite

show abstract

“…In general, bark extracts from P. strobus exhibited a higher inhibitory potential than the other evaluated extracts, whereas bark extracts from P. caribaea had the lowest one, against T. versicolor fungi growth, at the concentrations tested experimentally. In previous studies, Rutiaga et al (1995) reported that extracts from Enterolobium cyclocarpum obtained using ethanol and cyclohexane against T. versicolor fungus growth, at a concentration of 1.0 g L -1 show inhibition values of 80% and 25%, respectively; applying the same solvents and concentration to extracts from Dalbergia granadillo, inhibition values were 85% and 100%, respectively.…”

Section: Antifungal Potentialmentioning

confidence: 95%

“…The agar dilution method (Rutiaga et al 1995) for antifungal potential of pine bark extracts was used. To prevent alteration of physicochemical stability, the extracts were not sterilized.…”

Section: Antifungal Assaysmentioning

confidence: 99%

“…Petri dishes containing only culture medium (blank) and other Petri dishes containing both culture medium and a solvent mixture (controls) were inoculated with fungi. Antifungal activity (AFA) was calculated according to the following formula (Rutiaga et al 1995):…”

Section: Antifungal Assaysmentioning

confidence: 99%

“…orinocense Benth, Tabebuia serratifolia (Vahl) Nicholson and, Peltogyne porphyrocardia Griseb; T. versicolor fungus growth showed inhibition values of 67%, 81%, 90% and 40%, respectively, at a concentration of 0.2% v/v. Martínez-Sotres et al (2012) reported that heartwood extracts from Dalbergia congestiflora Pittier obtained using hexane, inhibited a 100% of T. versicolor growth at a concentration of 250 mg L -1 , whereas extracts obtained using acetone show a 0% inhibition at the same concentration. Conifer bark extracts in the present study showed better performance at the same concentrations than all the hardwood extracts cited above, except on Dalbergia extracts using hexane.…”

Section: Antifungal Potentialmentioning

confidence: 99%

See 2 more Smart Citations

Fungitoxic Potential of Extracts of Four Pinus spp. Bark to Inhibit Fungus Trametes versicolor (L. ex. Fr.) Pilát

Lomelí-Ramírez¹,

Dávila-Soto²,

Silva-Guzmán³

et al. 2016

BioResources

View full text Add to dashboard Cite

Pinus bark was extracted through a mixture of acetone-hexane-water 54:44:2 V. Bioassays were performed according to the agar dilution method (petri dish) using concentrations of 0.1, 0.5, and 1.0 mg mL -1 for each of the obtained extracts. All extracts showed some inhibition degree. Crude extracts of P. strobus bark showed the greatest inhibition degree. Antifungal potential of all tested extracts at a concentration of 1.0 mg mL -1 was classified as toxic. Through simple regression models, concentrations were calculated in order to achieve a 50% inhibition (IC50) and the minimal inhibition concentration (MIC). MIC values were 1.58, 1.72, 1.24, and 1.94 mg mL -1 for bark extracts of P. strobus, P. douglasiana, P. caribaea, and P. leiophylla, respectively.

show abstract

New Insights into Heartwood and Heartwood Formation

Kampe

Magel

2013

Plant Cell Monographs

View full text Add to dashboard Cite

Medicarpin, an antifungal compound identified in hexane extract of Dalbergia congestiflora Pittier heartwood

Cited by 33 publications

References 7 publications

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

Fungitoxic Potential of Extracts of Four Pinus spp. Bark to Inhibit Fungus Trametes versicolor (L. ex. Fr.) Pilát

New Insights into Heartwood and Heartwood Formation

Contact Info

Product

Resources

About