Microwave-Assisted Semisynthesis and Leishmanicidal Activity of Some Phenolic Constituents from Lichens-Reference-Cited by-同舟云学术

Microwave-Assisted Semisynthesis and Leishmanicidal Activity of Some Phenolic Constituents from Lichens

Published:2023-09-26 Issue:10 Volume:10 Page:524
ISSN:2297-8739
Container-title:Separations
language:en
Short-container-title:Separations

Author:

Castañeta Grover¹^ORCID,Villagomez Rodrigo¹,Salamanca Efrain²,Canaviri-Paz Pamela³^ORCID,Bravo José A.¹,Vila José L.¹,Bárcenas-Pérez Daniela⁴⁵^ORCID,Cheel José⁴^ORCID,Sepúlveda Beatriz⁶,Giménez Alberto²,Areche Carlos⁷^ORCID

Affiliation:

1. Instituto de Investigaciones Químicas IIQ, Universidad Mayor de San Andrés UMSA, Av. Villazón N° 1995, Box 303, La Paz 0201-0220, Bolivia

2. Instituto de Investigaciones Fármaco Bioquímicas, Área de Química Farmacéutica, Facultad de Ciencias Farmacéuticas y Bioquímicas, Universidad Mayor de San Andrés, Av. Saavedra N° 2224, Miraflores, Box 303, La Paz 0201-0220, Bolivia

3. Department of Food Technology, Engineering and Nutrition, Faculty of Engineering, Lund University, Box 117, SE-221 00 Lund, Sweden

4. Laboratory of Algal Biotechnology-Centre ALGATECH, Institute of Microbiology of the Czech Academy of Sciences, Opatovicky Mlyn, 37981 Trebon, Czech Republic

5. Faculty of Science, University of South Bohemia, Branišovská 1760, 37005 České Budějovice, Czech Republic

6. Departamento de Ciencias Químicas, Campus Viña del Mar, Universidad Andres Bello, Quillota 980, Viña del Mar 2520000, Chile

7. Departamento de Química, Facultad de Ciencias, Universidad de Chile, Box 653, Las Palmeras 3425, Ñuñoa, Santiago 8320000, Chile

Abstract

Leishmaniasis is considered one of the most untreated tropical diseases in the world. In this study, we investigated the in vitro leishmanicidal activity and cytotoxicity of various isolated lichen substances, including atranorin (1), usnic acid (2), gyrophoric acid (3), salazinic acid (4), galbinic acid (5), and parietin (6), and some semi-synthetic imine derivatives of usnic acid (7, 8, 9) and atranorin (10, 11, 12, 13). Imine condensation reactions with hydrazine and several amines were assisted by microwave heating, an efficient and eco-friendly energy source. The most interesting result was obtained for compound 2, which has high leishmanicidal activity but also high cytotoxicity. This cytotoxicity was mitigated in its derivative, 9, with better selectivity and high antileishmanic activity. This result may indicate that the usnic acid derivative (9) obtained using condensation with two cyclohexylamine groups is a promising lead compound for the discovery of new semisynthetic antiparasitic drugs.

Funder

Agencia Nacional de Investigación y Desarrollo de CHILE

Publisher

MDPI AG

Subject

Filtration and Separation,Analytical Chemistry

Link

https://www.mdpi.com/2297-8739/10/10/524/pdf

Reference48 articles.

1. WHO (2010). Control of the Leishmaniases: Report of a Meeting of the WHO Expert Commitee on the Control of Leishmaniases, Report No. 9789241209496.

2. Ultrastructural Analysis of Leishmania infantum chagasi Promastigotes Forms Treated In Vitro with Usnic Acid;Martins;Sci. World J.,2015

3. Cheuka, P., Mayoka, G., Mutai, P., and Chibale, K. (2017). The Role of Natural Products in Drug Discovery and Development against Neglected Tropical Diseases. Molecules, 22.

4. The impact of microwave synthesis on drug discovery;Kappe;Nat. Rev. Drug Discov.,2006

5. Leadbeater, N. (2010). Microwave Heating as a Tool for Sustainable Chemistry, CRC Press.