Special Issue "Synthesis of Flavonoids or Other Nature-Inspired Small Molecules"

A special issue of Molbank (ISSN 1422-8599). This special issue belongs to the section "Natural Products".

Deadline for manuscript submissions: 15 December 2021.

Special Issue Editor

Dr. Giovanni Ribaudo
E-Mail Website
Guest Editor
Department of Molecular and Translational Medicine, University of Brescia, Viale Europa 11, 25123 Brescia, Italy
Interests: medicinal chemistry; organic synthesis; analytical chemistry; mass spectrometry; NMR; natural products; molecular modeling
Special Issues and Collections in MDPI journals

Special Issue Information

Dear Colleagues,

Every organic chemist should agree that, as stated by Nobel Laureate Frances H. Arnold, “by far, nature is the best chemist of all time”. Natural compounds are characterized by a unique variety of chemical structures, functional groups, and stereochemical properties. Moreover, from the medicinal chemistry point of view, several naturally occurring small molecules are endowed with valuable biological activities and have inspired the design and development of drugs.

Flavonoids represent an outstanding example among natural compounds. These molecules are polyphenols produced by plants and fungi, constituted by two phenyls and a heterocyclic ring, disposed differently according to the sub-category. Flavonoids and semi-synthetic derivatives have been extensively studied in light of their wide bioactivity spectrum: antioxidant, antiproliferative, antibacterial and anti-inflammatory. In addition, several other classes of natural or nature-inspired molecules, such as alkaloids and terpenoids, are particularly attractive from a chemical or biological perspective.

This Special Issue aims at collating original contributions describing the synthesis of natural compounds and semi-synthetic derivatives of natural molecules. Articles should contain original and efficient synthetic approaches or significant process innovations in the preparation of natural and semi-synthetic compounds, with a particular focus on biologically relevant molecules. Moreover, research articles reporting significant results concerning extraction procedures, structural elucidation and structural characterization of natural compounds and derivatives involving the use of advanced analytical techniques (chromatography, 1D and 2D NMR, mass spectrometry, IR and UV spectroscopy) are particularly welcome.

Dr. Giovanni Ribaudo
Guest Editor

Manuscript Submission Information

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Keywords

  • flavonoids
  • alkaloids
  • natural compounds
  • semi-synthetic compounds
  • heterocycles
  • organic chemistry
  • stereochemistry
  • structural elucidation
  • analytical chemistry

Published Papers (7 papers)

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Research

Communication
Bioactive Antidiabetic Flavonoids from the Stem Bark of Cordia dichotoma Forst.: Identification, Docking and ADMET Studies
Molbank 2021, 2021(2), M1234; https://doi.org/10.3390/M1234 - 11 Jun 2021
Viewed by 218
Abstract
Cordia dichotoma Forst. (F. Boraginaceae) has been traditionally used for the management of a variety of human ailments. In our earlier work, the antidiabetic activity of methanolic bark extract of C. dichotoma (MECD) has been reported. In this paper, two flavonoid molecules were [...] Read more.
Cordia dichotoma Forst. (F. Boraginaceae) has been traditionally used for the management of a variety of human ailments. In our earlier work, the antidiabetic activity of methanolic bark extract of C. dichotoma (MECD) has been reported. In this paper, two flavonoid molecules were isolated (by column chromatography) and identified (by IR, NMR and mass spectroscopy/spectrometry) from the MECD with an aim to investigate their antidiabetic effectiveness. Molecular docking and ADMET studies were carried out using AutoDock Vina software and Swiss ADME online tool, respectively. The isolated flavonoids were identified as 3,5,7,3′,4′-tetrahydroxy-4-methoxyflavone-3-O-l-rhamnopyranoside and 5,7,3′-trihydroxy-4-methoxyflavone-7-O-l-rhamnopyranoside (quercitrin). Docking and ADMET studies revealed the promising binding affinity of flavonoid molecules for human lysosomal α-glucosidase and human pancreatic α-amylase with acceptable ADMET properties. Based on computational studies, our study reports the antidiabetic potential of the isolated flavonoids with predictive pharmacokinetics profile. Full article
(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)
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Short Note
Kokosanolide D: A New Tetranortriterpenoid from Fruit Peels of Lansium domesticum Corr. cv Kokossan
Molbank 2021, 2021(2), M1232; https://doi.org/10.3390/M1232 - 10 Jun 2021
Viewed by 309
Abstract
A novel tetranortriterpenoid named kokosanolide D has been isolated from fruit peels of Lansium domesticum. The structure of kokosanolide D was elucidated primarily on the basis of spectroscopic data including infrared, 1D and 2D-NMR, as well as high resolution mass spectroscopy analysis [...] Read more.
A novel tetranortriterpenoid named kokosanolide D has been isolated from fruit peels of Lansium domesticum. The structure of kokosanolide D was elucidated primarily on the basis of spectroscopic data including infrared, 1D and 2D-NMR, as well as high resolution mass spectroscopy analysis and comparison with related compounds previously reported. Full article
(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)
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Short Note
N-[7-Chloro-4-[4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl]quinoline]-acetamide
Molbank 2021, 2021(2), M1213; https://doi.org/10.3390/M1213 - 20 May 2021
Viewed by 349
Abstract
The 1,2,3-triazole is a well-known biologically active pharmacophore constructed by the copper-catalyzed azide–alkyne cycloaddition. We herein reported the synthesis of 4-amino-7-chloro-based [1,2,3]-triazole hybrids via Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of 4-azido-7-chloroquinoline with an alkyne derivative of acetaminophen. The compound was fully characterized by Fourier-transform [...] Read more.
The 1,2,3-triazole is a well-known biologically active pharmacophore constructed by the copper-catalyzed azide–alkyne cycloaddition. We herein reported the synthesis of 4-amino-7-chloro-based [1,2,3]-triazole hybrids via Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of 4-azido-7-chloroquinoline with an alkyne derivative of acetaminophen. The compound was fully characterized by Fourier-transform infrared (FTIR), proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), heteronuclear single quantum coherence (HSQC), ultraviolet (UV) and high-resolution mass spectroscopies (HRMS). This compound was screened in vitro with different normal and cancer cell lines. The drug likeness of the compound was also investigated by predicting its pharmacokinetic properties. Full article
(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)
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Short Note
2-Propyl-N′-[1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]pentanehydrazide
Molbank 2020, 2020(4), M1164; https://doi.org/10.3390/M1164 - 26 Oct 2020
Viewed by 732
Abstract
2-Propyl-N′-[1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]pentanehydrazide was obtained in 80% yield via the Einhorn variation of the Schotten–Baumann method by (+)-camphor hydrazide condensation with valproic acid (VPA) chloride. The structure of the titled compound was verified by Raman, FTIR, 1H-NMR, and 13C-NMR spectral analysis [...] Read more.
2-Propyl-N′-[1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]pentanehydrazide was obtained in 80% yield via the Einhorn variation of the Schotten–Baumann method by (+)-camphor hydrazide condensation with valproic acid (VPA) chloride. The structure of the titled compound was verified by Raman, FTIR, 1H-NMR, and 13C-NMR spectral analysis along with FAB-mass spectrometry. Thermal properties of synthesized derivative were elucidated by DSC and its purity by HPLC. The compound was successfully tested as a potential anticonvulsant agent based on models of chemically- and electrically-induced seizures. Full article
(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)
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Short Note
3-Hydroxy-8,14-secogammacera-7,14-dien-21-one: A New Onoceranoid Triterpenes from Lansium domesticum Corr. cv kokossan
Molbank 2020, 2020(4), M1157; https://doi.org/10.3390/M1157 - 30 Sep 2020
Cited by 1 | Viewed by 871
Abstract
A new onoceranoid triterpenes, namely 3-hydroxy-8,14-secogammacera-7,14-dien-21-one (1), has been isolated from the fruit peels of Lansium domesticum Corr. cv kokossan. The structure of 1 was determined on the basis of spectroscopic data including infrared, 1D and 2D-NMR, as well as [...] Read more.
A new onoceranoid triterpenes, namely 3-hydroxy-8,14-secogammacera-7,14-dien-21-one (1), has been isolated from the fruit peels of Lansium domesticum Corr. cv kokossan. The structure of 1 was determined on the basis of spectroscopic data including infrared, 1D and 2D-NMR, as well as high resolution mass spectroscopy analysis. Compound 1 showed a weak activity against MCF-7 breast cancer cell lines. Full article
(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)
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Short Note
5,5′-Oxybis(1,3,7-trihydroxy-9H-xanthen-9-one): A New Xanthone from the Stem Bark of Garcinia porrecta (Clusiaceae)
Molbank 2020, 2020(3), M1153; https://doi.org/10.3390/M1153 - 12 Aug 2020
Viewed by 779
Abstract
A new polyoxygenated dimer-type xanthone, namely 5,5′-oxybis(1,3,7-trihydroxy-9H-xanthen-9-one (1), has been isolated from the stem bark of Garcinia porrecta. The structure of 1 was determined based on spectroscopic data, including 1D and 2D-NMR as well as high resolution mass spectroscopy analysis. Full article
(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)
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Short Note
2-(3,4-Dihydroxyphenyl)-4-(2-(4-nitrophenyl)hydrazono)-4H-chromene-3,5,7-triol
Molbank 2020, 2020(3), M1144; https://doi.org/10.3390/M1144 - 29 Jun 2020
Cited by 4 | Viewed by 1038
Abstract
On the basis of the knowledge from traditional herbal and folk medicine, flavonoids are among the most studied chemical classes of natural compounds for their potential activity as phosphodiesterase 5 (PDE5) inhibitors. We here describe the preparation of a semi-synthetic hydrazone derivative of [...] Read more.
On the basis of the knowledge from traditional herbal and folk medicine, flavonoids are among the most studied chemical classes of natural compounds for their potential activity as phosphodiesterase 5 (PDE5) inhibitors. We here describe the preparation of a semi-synthetic hydrazone derivative of quercetin, 2-(3,4-dihydroxyphenyl)-4-(2-(4-nitrophenyl)hydrazono)-4H-chromene-3,5,7-triol, that was obtained via a single-step modification of the natural compound. The product was characterized by NMR, mass spectrometry and HPLC. Preliminary molecular modeling studies suggest that this compound could efficiently interact with PDE5. Full article
(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)
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