Abstract
4-Nerolidylcatechol (4NRC), a secondary metabolite described as a potent antioxidant that presents anti-inflammatory, antimalarial, analgesic, and cytotoxic properties, has been receiving prominence in the catechol class. In this work, a theoretical DFT study of the vibrational, structural, and quantum properties of 4-nerolidylcatechol (4NRC) using the B3LYP/6-311G (2d,p) level is presented. The theoretical molecular geometry data were compared with the X-ray data of a similar molecule in the associated literature and a conformational study is presented, with the aim of providing a good comprehension of the 4NRC structural arrangement and stability. Also, HOMO-LUMO energy gap and natural bond orbitals (NBOs) were performed and discussed. The calculated UV spectrum showed similarity to the experimentally obtained data, with transitions assigned. The comparative IR studies revealed that intermolecular hydrogen bonds that stabilize dimeric forms are plausible and also allowed the assignment of several characteristic vibrations. Molecular docking calculations with DNA topoisomerase I-DNA complex (TOPO-I), glyceraldehyde 3-phospate dehydrogenase (GAPDH), and Plasmodium falciparum lactate dehydrogenase (PfLDH) showed binding free energies of −6.3, −6.5, and −7.6 kcal/mol, respectively, which indicates that 4NRC is a good competitive inhibitor for these enzymes.
Highlights
Catechols are a group of small molecules with physiological importance, acting as effective structural units in many adrenergic, Parkinson’s disease [1], attention-deficit hyperactivity disorder (ADHD) [2], bronchodilator, antidepressants, antihypertensive drugs, perfumes, and agrochemical ingrediants [3]
natural bond orbitals (NBOs) values were obtained with the program NBO 3.1, implemented in the GAUSSIAN 09 package. e assignments of the calculated IR wavenumbers were aided by the animation option present in GAUSSVIEW 5.0, which promotes a visual presentation of the vibrational modes [29]. e potential energy distribution (PED) was calculated using the VEDA 4 software package [30]. e basis set superposition error (BSSE) of the interaction energies of the dimer was corrected by the counterpoise (CP) method [31]. e methodology consisted in the single point CP corrections on the conventionally optimized structures
Geometry Optimization and Conformational Analysis. e theoretical geometry optimization results of the studied molecules, which were calculated using the B3LYP/6-311G (2d,p) approach, were compared with X-ray data for epinine hydrobromide [32], due to the fact that it is a similar structure (Table S1). e compound shows certain polarities being soluble in chloroform and ethyl acetate, with a theoretical dipole moment of 2.09 D. e structure showed stable conformations and good structural cohesion with C1 symmetry and energy values of −968.97 a.u
Summary
Catechols are a group of small molecules with physiological importance, acting as effective structural units in many adrenergic, Parkinson’s disease [1], attention-deficit hyperactivity disorder (ADHD) [2], bronchodilator, antidepressants, antihypertensive drugs, perfumes, and agrochemical ingrediants (for the production of pesticides) [3]. Its potent antioxidant activity is largely established in the literature [8,9,10,11,12], but other pharmacological properties, such as antimicrobial [13], analgesic, anti-inflammatory [14], cytotoxic [15, 16], and antimalarial activities [17] are related to 4NRC It is the major secondary metabolite of Piper genus plants, traditionally known for their use in the treatment of various diseases [12, 15, 17,18,19,20]. It is important to mention that a theoretical study of the interaction of 4NRC with 2hydroxypropyl-β-cyclodextrin (HP-b-CD) was performed previously but through a mechanical molecular approach [27]
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
