Density-functional theory of the catnip molecule, nepetalactone

Nepetalactones belongs to the group of iridoid monoterpenoids, which are present in the aerial parts of nepeta plants. Nepetalactone is an attractant to feline animals causing euphoric effects, while it is a repellent to mosquitoes and cockroaches. It is also a pheromone for several insect aphid spe...

Full description

Saved in:
Bibliographic Details
Published in:Molecular and cellular biochemistry 2022-04, Vol.477 (4), p.1139-1153
Main Authors: Badshah, Syed Lal, Jehan, Rabiya
Format: Article
Language:English
Subjects:
Analysis
Animals
Aquatic insects
Biochemistry
Biomedical and Life Sciences
Cardiology
Cats
Chemical bonds
Cockroaches
Cyclopentane Monoterpenes - chemistry
Dengue fever
Density functional theory
Electronic structure
Enzymes
Farms
Hypothalamus
Insect Repellents - chemistry
Insects
Life Sciences
Malaria
Medical Biochemistry
Molecular orbitals
Molecular structure
Monoterpenoids
Mosquitoes
Nervous system
Neurons
NMR
Nuclear magnetic resonance
Oncology
Pyrones - chemistry
Repellents
Spectra
Spectral signatures
Spectroscopy, Fourier Transform Infrared
Tropical diseases
Vector-borne diseases
Viral infections
Zika virus
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Nepetalactones belongs to the group of iridoid monoterpenoids, which are present in the aerial parts of nepeta plants. Nepetalactone is an attractant to feline animals causing euphoric effects, while it is a repellent to mosquitoes and cockroaches. It is also a pheromone for several insect aphid species. The main objective of this research was to study the electronic and spectral properties of nepetalactones. We investigated its structural properties using hybrid density-functional theory of B3LYP and WB97XD functional with the 6-311++G(d,p) basis set to optimize the geometry, and then computed the electronic structure, HOMO–LUMO, natural bond orbitals, molecular electronic potential and its contour map. We also obtained spectral signatures of NMR, IR and UV–Vis, and compared them with experimental data from the literature. The DFT study provided different electronic and spectral information that will be of value for further research on making new derivatives of nepetalactones for commercial purposes. Nepetalactones have a promising future in the development of novel mosquito repellents for the control of malaria and arboviral diseases.
ISSN:0300-8177
1573-4919
DOI:10.1007/s11010-022-04366-8