In Silico Studies on Sennidines—Natural Dianthrones from Senna

Abstract

The rapid development of technology allows for more accurate research of biological systems with the use of in silico methods. One of the tools is the quantum-chemical method used for determining the structure, properties and interactions of molecules of great pharmacological importance. The accuracy of theoretical models is increasing and can be a real help in biology, chemistry and pharmacy. The aim of the study is to determine the spatial structure and intramolecular interactions of sennidines—natural pharmaceutical substances present in Senna species. Calculations carried out in the gas-phase and in the solvent model, compared with the available experimental data indicate the possibility of sennidines to form conformers. QTAIM and NCI analysis suggests the presence of many intramolecular interactions in the sennidin structure. Taking into account the lowest energy optimized structure, it can be predicted that the sennidin in the gauche conformation will be present in the plant material. The single C-C bond connecting the anthrone moieties is elongated and its reduced Bond Dissociation Energy (BDE) could be the cause of an easy breakdown of the sennidin molecule into monoanthrones. This work contains data on theoretical, vibrational and electron excitation spectra, which can be used in the analysis of experimental samples.

Theoretical Studies on the Structure and Intramolecular Interactions of Fagopyrins—Natural Photosensitizers of Fagopyrum

“…Such structure allows for the occurrence of numerous intramolecular interactions of diverse nature [38]. QTAIM analysis confirms the presence of the hydrogen bond interactions in the "peri" region of fagopyrin F. Hydroxyl groups directed to carbonyl oxygen form a stable moiety as in the case of hypericin and sennidin [13,14]. QTAIM analysis indicates that OHN interaction can be formed in both the "peri" and "bay" region.…”

“…The structure and intramolecular interactions of polycyclic compounds affect the physical and chemical properties and can influence potential applications of the compounds in pharmacy and medicine [9][10][11][12]. As shown in earlier work on hypericin [13] and sennidines [14], a highly substituted polycyclic system can exhibit a non-planar structure due to a variety of intramolecular interactions. At the time of writing this paper, data unambiguously define the spatial and electronic structures of fagopyrins.…”

“…The structure with the lowest energy (structure 14) favors the formation of OHN hydrogen bonds and the breaking of the OHO hydrogen bonds in the "bay" region of the molecule. The piperidine ring shows a "chair" conformation for all the obtained structures (structure [13][14][15][16][17][18]. Breaking of the OHN hydrogen bond located in the "bay" region results in leaving the piperidine ring free and increasing the energy of the molecule by 7.0 kcal•mol −1 (structure 13).…”

Values of Islamic Education and Science Learning in the Tradition of Jeleng Minyak 1000 Hajat

“…In addition, the swallow's nest contains nutrients water 15.90%, Alanine 1.31%, Arginine 3.93%, Amino Acid 4.56, Aspartic Acid 6.34%, Glutamic Acid 9.61%, Sialic Acid 9%, Phenylalanine 4.49%, Fucose 0.7%, Galactose 16.9%, Galactosamine 7.2%, Glycine 1.87%, Glucosamine 5.3%, Histidine 2.31%, Isoleucine 1.80%, Carbohydrates 22.28%, Fat 0, 67%, Leucine 3.84%, Lysine 5.44%, Methionine 0.48%, Proline 3.64%, Protein 58.55%, Serine 4.56%, Tyrosine 3.92%, Threonine 3.82%, Valine 3.93% has propertiesAnti-inflammatory (Novenda & Nuroini, 2019) as well as antioxidants (Courtois et al, 2021). Senna leaves have anti-inflammatory activity, oxidative stress (Nayan et al, 2021;Szymanski & Majerz, 2021) as well as antioxidants (Senna et al, 2022) and antiinfective (Alshehri et al, 2022). Saffron as an anticonvulsant, anti-depressant, anti-inflammatory, antitumor, free radical scavenger, and improves memory (Ashktorab et al, 2019;Zeinali et al, 2019).…”