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Natural Product Research
Formerly Natural Product Letters
Volume 34, 2020 - Issue 24
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Research Articles

Studies on the bioactive flavonoids isolated from Azadirachta indica

Francisco Cen-Pachecoa Faculty of Bioanalysis, Veracruz University, Veracruz, Veracruz, MéxicoCorrespondence[email protected] [email protected]
ORCID Iconhttps://orcid.org/0000-0001-8506-2435View further author information
ORCID Icon,
Araceli Ortiz-Celiseob Food Research and Development Unit, Technological Institute of Veracruz, México and Faculty of Bioanalysis, Veracruz University, Veracruz, Veracruz, MéxicoView further author information
,
Alvaro Peniche-Cardeñac Faculty of Medicine Veterinary and Zootechnics, Veracruz University, Veracruz, Veracruz, MéxicoView further author information
,
Omar Bravo-Ruizc Faculty of Medicine Veterinary and Zootechnics, Veracruz University, Veracruz, Veracruz, MéxicoView further author information
,
Fernando C. López-Fentanesa Faculty of Bioanalysis, Veracruz University, Veracruz, Veracruz, MéxicoView further author information
,
Gerardo Valerio-Alfarod Food Research and Development Unit Technological Institute of Veracruz, Veracruz, Veracruz, MéxicoView further author information
&
José J. Fernándeze Institute of Bio-Organic Chemistry Antonio González, Department of Organic Chemistry, University of La Laguna, La Laguna, Tenerife, SpainCorrespondence[email protected] [email protected]
View further author information
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Pages 3483-3491 | Received 25 Oct 2018, Accepted 04 Feb 2019, Published online: 05 Mar 2019
 
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Abstract

Two novel natural metabolites, 3-O-butyl-(-)-epicatechin (1) and 3-O-butyl-(-)-epigallocatechin (2), as well as several known substances, (−)-epicatechin (3), (+)-gallocatechin (4), (−)-epigallocatechin (5), azadirachtin A (6), trilinolein (7) and octadecanoic acid-tetrahydrofuran-3,4-diyl ester (8), were isolated from the bark of Azadirachta indica. The structures of all compounds were established by comprehensive and comparative spectroscopic analysis of NMR and ESI-HRMS data. The new metabolites 1 and 2 represent one of the few examples of natural compounds with a butyl ether group moiety. The acaricidal activity of the compounds was tested using a standard Shaw larval immersion assay. All the compounds, except 7, possess a LD50 value less than or equal to 7.2 mM.

Graphical Abstract

Disclosure statement

The authors declare that they have no competing interests.

Additional information

Funding

This work was supported by the Secretary of Public Education of Mexico [SEP-PROMEP, grant number PROMEP/103.5/13/7135].

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