Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
6.7
4.6
Journals
Molecules
Special Issues
Chemistry of Natural Organic Compounds
molecules-logo
Submit to Molecules Review for Molecules Propose a Special Issue

Journal Menu

► Journal Menu

Journal Browser

► Journal Browser
share announcement

Chemistry of Natural Organic Compounds

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 October 2021) | Viewed by 18259

Special Issue Editor

Prof. Dr. Andrei I. Khlebnikov

E-Mail Website
Guest Editor
Kizhner Research Center, Tomsk Polytechnic University, 634050 Tomsk, Russia
Interests: organic chemistry; drug design; coordination chemistry; chemistry of natural organic compounds

Special Issue Information

Dear Colleagues,

Modern organic chemistry is a complex integrated discipline that is based on enormous factual material and has a theoretical foundation using the concepts and methods of physical chemistry and physics, biological chemistry and biology, industrial chemistry and technology. Therefore, it is logical to subdivide organic chemistry into several branches, closely intertwined but at the same time quite different from each other.

One of these disciplines is the chemistry of natural compounds. Developing in the bosom of organic chemistry from the very beginning of its inception as a science, it continuously enriches the latter with new ideas, new facts, and new methods. Currently, the chemistry of natural compounds is the largest branch of organic chemistry. More than half of all research and publications in the field of organic chemistry in recent decades were devoted to substances of natural origin.

The importance of chemistry of natural compounds for solving many basic problems of natural science is difficult to overestimate. Located on the border with biological disciplines and closely related to biochemistry, the chemistry of natural compounds plays a crucial role in studying the mechanism of action of enzymes and the chemical nature of biological processes, including the transmission of inherited traits, the essence of aging processes, problems of nervous activity and other no less important questions. Natural organic compounds are extremely important for the fight against the most dangerous diseases (radiation sickness, cancer, HIV, diabetes, tuberculosis, hypertension, etc.).

This Special issue of Molecules welcomes leading scientists to submit original research papers and reviews in the field of natural organic compounds isolation, synthesis, analysis, chemical modification, and biological activity. Potential topics include but are not limited to keywords listed below.

Prof. Dr. Andrei I. Khlebnikov
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Carbohydrates and polysaccharides
  • Polyphenols
  • Coumarins, flavonoids and related compounds
  • Terpenoids
  • Steroids
  • Amino acids, peptides and proteins
  • Alkaloids
  • Nucleosides, nucleotides and nucleic acids
  • Porphyrins
  • Chemical modification of natural organic compounds

Published Papers (6 papers)

Download All Papers
Order results
Result details
Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:

Research

31 pages, 3680 KiB  
Article
Syntheses Based on 3,4α-Epoxy-1,5,7α,6β(H)-guai-10(14),11(13)-dien-6,12-olide
by Sergazy Adekenov
Molecules 2022, 27(6), 1862; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27061862 - 13 Mar 2022
Cited by 1 | Viewed by 1966
Abstract
The sesquiterpene γ-lactone estafiatin 1, the molecule of which has a structure of 3,4α-epoxy-1,5,7α,6β(H)-guai-10(14),11(13)-dien-6,12-olide, is characteristic of plants of the genera Achillea L. and Artemisia L. of the Asteraceae family. This article presents the results of chemical modification for three reaction centers [...] Read more.
The sesquiterpene γ-lactone estafiatin 1, the molecule of which has a structure of 3,4α-epoxy-1,5,7α,6β(H)-guai-10(14),11(13)-dien-6,12-olide, is characteristic of plants of the genera Achillea L. and Artemisia L. of the Asteraceae family. This article presents the results of chemical modification for three reaction centers of the estafiatin molecule 1: epoxy cycle, exomethylene group conjugated with γ-lactone carbonyl, and exomethylene group in position C10=C14; and at the same time 33 new derivatives were synthesized, the structures of which were established based on physicochemical constants, spectral data (IR-, PMR-, 13C-NMR), and X-ray diffraction analysis. The stereo- and regiospecificity, as well as the chemoselectivity of the reaction based on estafiatin molecule 1, are discussed. The reactivity of the substrate is significantly influenced by the stereochemistry of its molecule, the nature of the reagent, and the reaction medium. Based on the results of in silico screening, derivatives of estafiatin with high binding energies for both DNA-topoisomerase I and DNA-topoisomerase II were identified. The values of the inhibitory dose of IC50 for estafiatin 1 and its derivatives were determined on cell lines of eight types of tumors. in vivo experiments of the samples made it possible to establish that estafiatin 1 and its derivatives have pronounced antitumor activity against Pliss lymphosarcoma, Walker’s carcinosarcoma, sarcoma 45, sarcoma-180, alveolar liver cancer PC-1, leukemia P-388 and L-1210, and sarcoma-45 resistant to 5-fluorouracil. Full article
(This article belongs to the Special Issue Chemistry of Natural Organic Compounds)
►▼ Show Figures

Figure 1

20 pages, 1007 KiB  
Article
Innate Immunomodulatory Activity of Cedrol, a Component of Essential Oils Isolated from Juniperus Species
by Gulmira Özek, Igor A. Schepetkin, Moldir Yermagambetova, Temel Özek, Liliya N. Kirpotina, Shyryn S. Almerekova, Saule I. Abugalieva, Andrei I. Khlebnikov and Mark T. Quinn
Molecules 2021, 26(24), 7644; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26247644 - 16 Dec 2021
Cited by 17 | Viewed by 2957
Abstract
Little is known about the immunomodulatory activity of essential oils isolated from Juniperus species. Thus, we isolated essential oils from the cones and leaves of eight juniper species found in Montana and in Kazakhstan, including J. horizontalis, J. scopolorum, J. communis [...] Read more.
Little is known about the immunomodulatory activity of essential oils isolated from Juniperus species. Thus, we isolated essential oils from the cones and leaves of eight juniper species found in Montana and in Kazakhstan, including J. horizontalis, J. scopolorum, J. communis, J. seravschanica, J. sabina, J. pseudosabina, J. pseudosabina subsp. turkestanica, and J. sibirica. We report here the chemical composition and innate immunomodulatory activity of these essential oils. Compositional analysis of the 16 samples of Juniper essential oils revealed similarities and differences between our analyses and those previously reported for essential oils from this species. Our studies represent the first analysis of essential oils isolated from the cones of four of these Juniper species. Several essential oil samples contained high levels of cedrol, which was fairly unique to three Juniper species from Kazakhstan. We found that these essential oils and pure (+)-cedrol induced intracellular Ca2+ mobilization in human neutrophils. Furthermore, pretreatment of human neutrophils and N-formyl peptide receptor 1 and 2 (FPR1 and FPR2) transfected HL60 cells with these essential oils or (+)-cedrol inhibited agonist-induced Ca2+ mobilization, suggesting these responses were desensitized by this pretreatment. In support of this conclusion, pretreatment with essential oils from J. seravschanica cones (containing 16.8% cedrol) or pure (+)-cedrol inhibited human neutrophil chemotaxis to N-formyl peptide. Finally, reverse pharmacophore mapping predicted several potential kinase targets for cedrol. Thus, our studies have identified cedrol as a novel neutrophil agonist that can desensitize cells to subsequent stimulation by N-formyl peptide. Full article
(This article belongs to the Special Issue Chemistry of Natural Organic Compounds)
►▼ Show Figures

Graphical abstract

11 pages, 1688 KiB  
Article
Twice as Nice: The Duff Formylation of Umbelliferone Revised
by Vladislav V. Skarga, Vadim V. Negrebetsky, Yuri I. Baukov and Mikhail V. Malakhov
Molecules 2021, 26(24), 7482; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26247482 - 10 Dec 2021
Cited by 8 | Viewed by 2767
Abstract
More efficient and preferably more convenient and greener synthetic solutions in coumarin scaffold functionalization are in steady demand. The Duff ortho-formylation of unsubstituted umbelliferone was revised in this study. The reaction conditions were optimized based upon data from the literature analysis and [...] Read more.
More efficient and preferably more convenient and greener synthetic solutions in coumarin scaffold functionalization are in steady demand. The Duff ortho-formylation of unsubstituted umbelliferone was revised in this study. The reaction conditions were optimized based upon data from the literature analysis and resulted in unexpectedly rapid ortho-formylation of umbelliferone, yielding a mixture of ortho-formyl position isomers. Thorough studies on the separation of ortho-formylated umbelliferones using chromatographic and recrystallization methods as well as the evaluation of their solubility in common organic solvents led to complete resolution of 8-formyl- and 6-formylumbelliferones. The precise protocol for simultaneous preparation, extraction, and purification of 8-formyl- and 6-formylumbelliferones is provided, and the prospective studies of biological and pharmacological activities of these compounds are synopsized. Full article
(This article belongs to the Special Issue Chemistry of Natural Organic Compounds)
►▼ Show Figures

Figure 1

13 pages, 979 KiB  
Article
Bioguided Isolation of Active Compounds from Rhamnus alaternus against Methicillin-Resistant Staphylococcus aureus (MRSA) and Panton-Valentine Leucocidin Positive Strains (MSSA-PVL)
by Ikrame Zeouk, Wessal Ouedrhiri, Ines Sifaoui, Isabel L. Bazzocchi, José E. Piñero, Ignacio A. Jiménez, Jacob Lorenzo-Morales and Khadija Bekhti
Molecules 2021, 26(14), 4352; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26144352 - 19 Jul 2021
Cited by 5 | Viewed by 2127
Abstract
Despite intensified efforts to develop an effective antibiotic, S. aureus is still a major cause of mortality and morbidity worldwide. The multidrug resistance of bacteria has considerably increased the difficulties of scientific research and the concomitant emergence of resistance is to be expected. [...] Read more.
Despite intensified efforts to develop an effective antibiotic, S. aureus is still a major cause of mortality and morbidity worldwide. The multidrug resistance of bacteria has considerably increased the difficulties of scientific research and the concomitant emergence of resistance is to be expected. In this study we have investigated the in vitro activity of 15 ethanol extracts prepared from Moroccan medicinal plants traditionally used for treatment of skin infections. Among the tested species I. viscosa, C. oxyacantha, R. tinctorum, A. herba alba, and B. hispanica showed moderate anti-staphylococcal activity. However, R. alaternus showed promising growth-inhibitory effects against specific pathogenic bacteria especially methicillin-susceptible Staphylococcus aureus Panton-Valentine leucocidin positive (MSSA-PVL) and methicillin-resistant S. aureus (MRSA). The bioguided fractionation of this plant using successive chromatographic separations followed by nuclear magnetic resonance (NMR) and mass spectrometry (MS) including EIMS and HREIMS analysis yielded the emodin (1) and kaempferol (2). Emodin being the most active with MICs ranging between 15.62 and 1.95 µg/mL and showing higher activity against the tested strains in comparison with the crude extract, its mechanism of action and the structure-activity relationship were interestingly discussed. The active compound has not displayed toxicity toward murine macrophage cells. The results obtained in the current study support the traditional uses of R. alaternus and suggest that this species could be a good source for the development of new anti-staphylococcal agents. Full article
(This article belongs to the Special Issue Chemistry of Natural Organic Compounds)
►▼ Show Figures

Graphical abstract

21 pages, 1324 KiB  
Article
Chemical Composition and Immunomodulatory Activity of Essential Oils from Rhododendron albiflorum
by Igor A. Schepetkin, Gulmira Özek, Temel Özek, Liliya N. Kirpotina, Andrei I. Khlebnikov and Mark T. Quinn
Molecules 2021, 26(12), 3652; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26123652 - 15 Jun 2021
Cited by 16 | Viewed by 3119
Abstract
Rhododendron (Ericaceae) extracts contain flavonoids, chromones, terpenoids, steroids, and essential oils and are used in traditional ethnobotanical medicine. However, little is known about the immunomodulatory activity of essential oils isolated from these plants. Thus, we isolated essential oils from the flowers and leaves [...] Read more.
Rhododendron (Ericaceae) extracts contain flavonoids, chromones, terpenoids, steroids, and essential oils and are used in traditional ethnobotanical medicine. However, little is known about the immunomodulatory activity of essential oils isolated from these plants. Thus, we isolated essential oils from the flowers and leaves of R. albiflorum (cascade azalea) and analyzed their chemical composition and innate immunomodulatory activity. Compositional analysis of flower (REOFl) versus leaf (REOLv) essential oils revealed significant differences. REOFl was comprised mainly of monoterpenes (92%), whereas sesquiterpenes were found in relatively low amounts. In contrast, REOLv was primarily composed of sesquiterpenes (90.9%), with a small number of monoterpenes. REOLv and its primary sesquiterpenes (viridiflorol, spathulenol, curzerene, and germacrone) induced intracellular Ca2+ mobilization in human neutrophils, C20 microglial cells, and HL60 cells transfected with N-formyl peptide receptor 1 (FPR1) or FPR2. On the other hand, pretreatment with these essential oils or component compounds inhibited agonist-induced Ca2+ mobilization and chemotaxis in human neutrophils and agonist-induced Ca2+ mobilization in microglial cells and FPR-transfected HL60 cells, indicating that the direct effect of these compounds on [Ca2+]i desensitized the cells to subsequent agonist activation. Reverse pharmacophore mapping suggested several potential kinase targets for these compounds; however, these targets were not supported by kinase binding assays. Our results provide a cellular and molecular basis to explain at least part of the beneficial immunotherapeutic properties of the R. albiflorum essential oils and suggest that essential oils from leaves of this plant may be effective in modulating some innate immune responses, possibly by inhibition of neutrophil migration. Full article
(This article belongs to the Special Issue Chemistry of Natural Organic Compounds)
►▼ Show Figures

Graphical abstract

15 pages, 4935 KiB  
Article
Synthesis of Natural (−)-Antrocin and Its Enantiomer via Stereoselective Aldol Reaction
by Venkatachalam Angamuthu and Dar-Fu Tai
Molecules 2020, 25(4), 831; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25040831 - 14 Feb 2020
Cited by 5 | Viewed by 3666
Abstract
The total synthesis of (−)-antrocin and its enantiomer are presented. Antrocin (−)-1 is an important natural product which acts as an antiproliferative agent in a metastatic breast cancer cell line (IC50: 0.6 μM). The key features of this synthesis [...] Read more.
The total synthesis of (−)-antrocin and its enantiomer are presented. Antrocin (−)-1 is an important natural product which acts as an antiproliferative agent in a metastatic breast cancer cell line (IC50: 0.6 μM). The key features of this synthesis are: (a) selective anti-addition of trimethylsilyl cyanide (TMSCN) to α,β-unsaturated ketone; (b) resolution of (±)-7 using chiral auxiliary L-dimethyl tartrate through formation of cyclic ketal diastereomers followed by simple column chromatography separation and acid hydrolysis; (c) substrate-controlled stereoselective aldol condensation of (+)-12 with monomeric formaldehyde and pyridinium chlorochromate (PCC) oxidation for synthesis of essential lactone core in (−)-14; and (d) non-basic Lombardo olefination of the carbonyl at the final step to yield (−)-antrocin. In addition, (+)-9 cyclic ketal diastereomer was converted to (+)-antrocin with similar reaction sequences. Full article
(This article belongs to the Special Issue Chemistry of Natural Organic Compounds)
►▼ Show Figures

Graphical abstract

Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
 
Displaying articles 1-6
Back to TopTop