Sonochemical Synthesis of 2’-Hydroxy-Chalcone Derivatives with Potential Anti-Oomycete Activity

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Abstract

This work reports on the synthesis of eight new 2′-hydroxy-chalcones with potential anti-phytopathogenic applications in agroindustry, AMONG others, via Claisen–Schmidt condensation and ultrasound assisted reaction. Assays showed three chalcones with allyl moieties strongly inhibited growth of phytopathogenic oomycete Phytophthora infestans; moreover, compound 8a had a half maximal effective concentration (EC ₅₀) value (32.5 µg/mL) similar to that of metalaxyl (28.6 µg/mL). A software-aided quantitative structure–activity relationship (QSAR) analysis of the whole series suggests that the structural features of these new chalcones—namely, the fluoride, hydroxyl, and amine groups over the carbon 3′ of the chalcone skeleton—increase anti-oomycete activity.

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Human health risk assessment of antibiotic resistance associated with antibiotic residues in the environment: A review

Yujie Ben, Caixia Fu, Min Shan Hu … (2019)

The extensive use of antibiotics leading to the rapid spread of antibiotic resistance poses high health risks to humans, but to date there is still lack of a quantitative model to properly assess the risks. Concerns over the health risk of antibiotic residues in the environment are mainly (1) the potential hazard of ingested antibiotic residues in the environment altering the human microbiome and promoting emergence and selection for bacteria resistance inhabiting the human body, and (2) the potential hazard of creating a selection pressure on environmental microbiome and leading to reservoirs of antibiotic resistance in the environment. We provide a holistic view of health risk assessment of antibiotic resistance associated with antibiotic residues in the environment in contrast with that of the antibiotic resistant bacteria and discuss the main knowledge gaps and the future research that should be prioritized to achieve the quantitative risk assessment. We examined and summarized the available data and information on the four core elements of antibiotic resistance associated with antibiotic residues in the environment: hazard identification, exposure assessment, dose-response assessment, and risk characterization. The data required to characterize the risks of antibiotic residues in the environment is severely limited. The main future research needs have been identified to enable better assessments of antibiotic resistance associated with antibiotic residues in the environment: (1) establishment of a standardized monitoring guide of antibiotic residues and antibiotic resistance in the environment, (2) derivation of the relationship between antibiotic levels and pathogenic antibiotic-resistance development in different settings, and (3) establishment of the dose-response relationship between pathogenic antibiotic resistant bacteria and various infection diseases. After identification of key risk determinant parameters, we propose a conceptual framework of human health risk assessments of antibiotic residues in the environment. CAPSULE: A holistic view of human health risk assessment of antibiotic residues in the environment was provided.

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Beware of q2!

Alexander Golbraikh, Alexander Tropsha (2001)

Validation is a crucial aspect of any quantitative structure-activity relationship (QSAR) modeling. This paper examines one of the most popular validation criteria, leave-one-out cross-validated R2 (LOO q2). Often, a high value of this statistical characteristic (q2 > 0.5) is considered as a proof of the high predictive ability of the model. In this paper, we show that this assumption is generally incorrect. In the case of 3D QSAR, the lack of the correlation between the high LOO q2 and the high predictive ability of a QSAR model has been established earlier [Pharm. Acta Helv. 70 (1995) 149; J. Chemomet. 10(1996)95; J. Med. Chem. 41 (1998) 2553]. In this paper, we use two-dimensional (2D) molecular descriptors and k nearest neighbors (kNN) QSAR method for the analysis of several datasets. No correlation between the values of q2 for the training set and predictive ability for the test set was found for any of the datasets. Thus, the high value of LOO q2 appears to be the necessary but not the sufficient condition for the model to have a high predictive power. We argue that this is the general property of QSAR models developed using LOO cross-validation. We emphasize that the external validation is the only way to establish a reliable QSAR model. We formulate a set of criteria for evaluation of predictive ability of QSAR models.

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Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata.

Supinya Tewtrakul, Sanan Subhadhirasakul, Chatchanok Karalai … (2006)

Searching for anti-HIV-1 protease (PR) inhibitors of Thai medicinal plants led to the isolation of a new cyclohexenyl chalcone named panduratin C (1) and chalcone derivatives (2-6) from the methanol extract of Boesenbergia pandurata rhizomes. The known compounds were identified to be panduratin A (2), hydroxypanduratin A (3), helichrysetin (4), 2',4',6'-trihydroxyhydrochalcone (5), and uvangoletin (6). The structures of all compounds were elucidated on the basis of chemical and spectroscopic methods. It was found that 3 possessed the most potent anti-HIV-1 PR activity with an IC50 value of 5.6 microM, followed by 2 (IC50 = 18.7 microM), whereas other compounds exhibited only mild activity. Structure-activity relationships of these compounds on anti-HIV-1 PR activity are summarized as follows: (1) hydroxyl moiety at position 4 conferred higher activity than methoxyl group; (2) prenylation of dihydrochalcone was essential for activity; (3) hydroxylation at position 4''' reduced activity; and (4) introduction of double bond at C1' and C6' of chalcone gave higher activity. As regards active constituents contained in B. pandurata rhizomes, hydroxypanduratin A (3) and panduratin A (2) are active principles against HIV-1 PR.

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Journal

Journal ID (nlm-ta): Antibiotics (Basel)

Journal ID (iso-abbrev): Antibiotics (Basel)

Journal ID (publisher-id): antibiotics

Title: Antibiotics

Publisher: MDPI

ISSN (Electronic): 2079-6382

Publication date (Electronic): 04 September 2020

Publication date Collection: September 2020

Volume: 9

Issue: 9

Electronic Location Identifier: 576

Affiliations

[1 ]Laboratorio de Productos Naturales y Síntesis Orgánica (LPNSO), Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, Chile; genesis.lopez.miranda@ 123456gmail.com

[2 ]Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Av. Universidad #330, Curauma, Valparaíso 2340000, Chile; marco.mellado@ 123456pucv.cl

[3 ]Departamento de Ciencias Básicas, Campus Fernando May Universidad del Biobío. Avda. Andrés Bello 720, Casilla 447, Chillán 3780000, Chile; ewerner@ 123456ubiobio.cl

[4 ]Departamento de Química, Universidad Técnica Federico Santa María, Av. Santa María 6400, Vitacura, Santiago 7630000, Chile; bastian.said@ 123456usm.cl

[5 ]Instituto de Microbiología Clínica, Facultad de Medicina, Universidad Austral de Chile, Los Laureles s/n, Isla Teja, Valdivia 5090000, Chile; patricio.godoy@ 123456uach.cl

[6 ]Centro de Investigación Australbiotech, Universidad Santo Tomás, Avda. Ejército 146, Santiago 8320000, Chile; ncaro@ 123456australbiotech.cl

[7 ]Escuela de Agronomía Pontificia Universidad Católica de Valparaíso, Quillota, SanFrancisco s/n La Palma, Quillota 2260000, Chile; ximena.besoain@ 123456pucv.cl

[8 ]Escuela de Obstetricia y Puericultura, Facultad de Medicina, Universidad de Valparaíso, Angamos 655, Reñaca, Viña del Mar 2520000, Chile

Author notes

[* ]Correspondence: ivan.montenegro@ 123456uv.cl (I.M.); alejandro.madrid@ 123456upla.cl (A.M.); Tel.: +56-032-250-0526 (A.M.)

Author information

Marco Mellado https://orcid.org/0000-0001-9577-5180

Ximena Besoain https://orcid.org/0000-0002-4861-7961

Alejandro Madrid https://orcid.org/0000-0001-8977-7032

Article

Publisher ID: antibiotics-09-00576

DOI: 10.3390/antibiotics9090576

PMC ID: 7560025

PubMed ID: 32899705

SO-VID: c3647f1d-3969-40d7-b348-d7745fb17577

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Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

Sonochemical Synthesis of 2’-Hydroxy-Chalcone Derivatives with Potential Anti-Oomycete Activity

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Human health risk assessment of antibiotic resistance associated with antibiotic residues in the environment: A review

Beware of q2!

Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata.

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