Exploring the Universe of Natural Products: Recent Advances in Synthesis, Isolation and Structural Elucidation II

A special issue of Plants (ISSN 2223-7747). This special issue belongs to the section "Phytochemistry".

Deadline for manuscript submissions: closed (31 May 2023) | Viewed by 14407

Special Issue Editors


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Guest Editor
Department of Pharmaceutical Sciences, University of Piemonte Orientale, Largo Guido Donegani 2/3, 28100 Novara, Italy
Interests: natural product chemistry; synthetic methodologies applied to natural product synthesis; medicinal chemistry of natural products
Special Issues, Collections and Topics in MDPI journals

E-Mail Website
Guest Editor
Department of Pharmaceutical Sciences, University of Eastern Piedmont, Largo Donegani 2, 28100 Novara, Italy
Interests: phytochemistry; isolation and structural elucidation of secondary metabolites; bioprospecting
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Plants represent a fantastic cornucopia of secondary metabolites characterized by unique carbon skeletons related to powerful biological activities that have favored the birth of different traditional medicine systems. Although the plant kingdom has been widely explored already, many areas remain untouched, retaining their “treasures”. The study of natural products requires different expertise, and this multidisciplinary field can contribute to creating opportunities in the identification of new compounds with interesting pharmacological and ecological profiles. This issue will be an opportunity to showcase the latest advances in the exploration of untouched areas of the plant kingdom, focusing our attention on the isolation, structure characterization, and synthesis of interesting secondary metabolites. 

Dr. Alberto Minassi
Guest Editor

Manuscript Submission Information

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Keywords

  • isolation and structural elucidation
  • synthesis of natural products
  • bioactive secondary metabolites
  • plant secondary metabolites
  • synthetic methodologies applied to natural products

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Published Papers (5 papers)

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Research

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13 pages, 1994 KiB  
Article
Chemical Composition and In Vitro Evaluation of Antioxidant and Antiproliferative Effects of Volatile Oils Hydrodistilled from Onobrychis carduchorum C.C. Towns., a Kurdish Traditional Plant
by Hawraz Ibrahim M. Amin, Kamaran Abdoulrahman, Azad S. Sadraddin, Heman A. Smail, Zanko Hassan Jawhar, Kovan Dilawer Issa, Chabaco Armijos and Giovanni Vidari
Plants 2023, 12(16), 3013; https://doi.org/10.3390/plants12163013 - 21 Aug 2023
Viewed by 1318
Abstract
The volatile oils hydrodistilled from the aerial parts and roots of O. carduchorum C.C Towns. (Fabaceae) have been chemically characterized for the first time. A total of 43 constituents with an abundance >0.03% were identified and quantified in the two oils by GC/MS [...] Read more.
The volatile oils hydrodistilled from the aerial parts and roots of O. carduchorum C.C Towns. (Fabaceae) have been chemically characterized for the first time. A total of 43 constituents with an abundance >0.03% were identified and quantified in the two oils by GC/MS and GC/FID analyses. They comprise 38 components (98.58%) of the oil isolated from the aerial parts (OCA) and 34 components (93.33%) of the oil from the roots (OCR). Six constituents, α-pinene (23.11 ± 0.1%), β-elemene (17.33 ± 0.1%), 1,8-cineole (12.15 ± 0.2%), furfural (7.91 ± 0.1%), terpineol-4-ol (6.32 ± 0.2%), and limonene (4.13 ± 0.1%), accounted for about 75% of the total OCA oil. On the other hand, 1,8-cineole (15.79 ± 0.1%), furfural (10.44 ± 0.1%), β-elemene (10.14 ± 0.2%), α-terpineol (7.74 ± 0.1%), linalool (7.45 ± 0.1%), and α-pinene (4.76 ± 0.1%) made up about 60% of the OCR oil. The IC50 values of the scavenging activities of the OCA and OCR oils towards the DPPH radical and H2O2 were 79.8 ± 0.5 and 153.3 ± 0.6 μg/mL and 394.09 ± 0.2 and 311.67 ± 0.4 μg/mL, respectively. In addition, in the MTS assay, the OCA and OCR oils showed significant antiproliferative effects against T47D, MDA-MB-453, BG-1, and A549 human cancer cells that were more powerful than those against two normal human cell lines, HEK-293 and HFF-1. The abundant presence of β-elemene as an antiproliferative component of the two oils suggested the existence of a new chemotype of O. carduchorum. Full article
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9 pages, 2234 KiB  
Article
Non-Volatile Terpenoids and Lipophilic Flavonoids from Achillea erba-rotta Subsp. moschata (Wulfen) I. Richardson
by Stefano Salamone, Nicola Aiello, Pietro Fusani, Antonella Rosa, Mariella Nieddu, Giovanni Appendino and Federica Pollastro
Plants 2023, 12(2), 402; https://doi.org/10.3390/plants12020402 - 15 Jan 2023
Cited by 1 | Viewed by 1604
Abstract
Musk yarrow (Achillea erba-rotta subsp. moschata (Wulfen) I. Richardson) is endemic to the Central Alps, and is used to flavour alcoholic beverages. Despite its popularity as aromatizing agent and its alleged beneficial effects on digestion, the phytochemical profile of the plant is [...] Read more.
Musk yarrow (Achillea erba-rotta subsp. moschata (Wulfen) I. Richardson) is endemic to the Central Alps, and is used to flavour alcoholic beverages. Despite its popularity as aromatizing agent and its alleged beneficial effects on digestion, the phytochemical profile of the plant is still largely unknown and undiscovered. As a consequence, its authentication in aromatized products is impossible beyond sensory analysis allowing forgery. To address these issues, we phytochemically characterized a sample of musk yarrow from the Italian Eastern Alps, identifying, in addition to widespread phytochemicals (taraxasterol, apigenin), the guaianolides 3, 8, 9; the seco-caryophyllane 6; and the polymethoxylated lipophilic flavonoids 1, 4, and 5. The flavonoid xanthomicrol 1, a major constituent of the plant, was cytotoxic to HeLa cells, but only modestly affected primary 3T3 fibroblasts. On account of their stability, detectability by UV absorption, and concentration, the oxygenated flavonoids qualify as markers to validate the supply chain of the plant growers to consumers. Full article
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23 pages, 5497 KiB  
Article
The Structural, Biological, and In-Silico Profiling of Novel Capryloyl Tetra-Glucoside and Aliphatic Ester Constituents from the Abutilon indicum Offers New Perspectives on the Treatment of Pain and Inflammation
by Shadma Wahab, Abdulrhman Alsayari, Abdullatif Bin Muhsinah, Dalia Almaghaslah, Anzarul Haque, Mohammad Khalid, Sulaiman Mohammed Alnasser, Faizul Azam and Md. Sarfaraj Hussain
Plants 2022, 11(19), 2583; https://doi.org/10.3390/plants11192583 - 30 Sep 2022
Cited by 1 | Viewed by 1726
Abstract
Abutilon indicum L. (Malvaceae), more often referred to as Peeli booti, Kanghi, and Kakhi, is a perennial shrub found in many countries of Asia. Traditionally, this plant is used as a diuretic to treat inflammation, discomfort, urethral infections, and gout. Inflammation and pain [...] Read more.
Abutilon indicum L. (Malvaceae), more often referred to as Peeli booti, Kanghi, and Kakhi, is a perennial shrub found in many countries of Asia. Traditionally, this plant is used as a diuretic to treat inflammation, discomfort, urethral infections, and gout. Inflammation and pain are key topics of interest for researchers throughout the globe, since they are linked to almost every illness that could affect humans or animals. The present study was conducted to isolate the phytoconstituents from the methanolic extract of Abutilon indicum collected from the Bihar state Koshi river belt in India, and to evaluate the isolated phytoconstituents’ ability to reduce nociception and inflammation. Furthermore, molecular docking was performed to investigate the molecular interaction profile, with possible therapeutic targets for anti-inflammatory medicines. A. indicum methanolic extract yielded two novel phytocompounds identified as 5′-hydroxyhexyl n-hexadecanoate (AB-01) and n-octanoyl-β-D-glucopyranosyl-(2′-1′′)-β-D-glucopyranosyl-(2′′-1′′′)-β-D-glucopyranosyl-(2′′′-1′′′′)-β-D-glucopyranoside (AB-05), together with three previously recognized phytocompounds such as ester glucoside. All isolated molecules were tested for the efficacy of analgesic and anti-inflammatory characteristics at doses of 5 and 10 mg/kg body weight. The isolated compound’s molecular interaction profile with anti-inflammatory drug targets cyclooxygenase-2 and tumor necrosis factor-alpha possessed high potential energy in molecular docking. These findings may aid in developing anti-inflammatory and analgesic drugs from A. indicum. Full article
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14 pages, 834 KiB  
Article
Phytochemical Characterization of Cannabis sativa L. Chemotype V Reveals Three New Dihydrophenanthrenoids That Favorably Reprogram Lipid Mediator Biosynthesis in Macrophages
by Stefano Salamone, Lorenz Waltl, Anna Pompignan, Gianpaolo Grassi, Giuseppina Chianese, Andreas Koeberle and Federica Pollastro
Plants 2022, 11(16), 2130; https://doi.org/10.3390/plants11162130 - 16 Aug 2022
Cited by 4 | Viewed by 2999
Abstract
The growing general interest surrounding Cannabis sativa L. has led to a renewal in breeding and resulted in an impressive variability of chemotypical characteristics that required the division of cannabis into different recognized chemotypes. The chemotype V has been overlooked in terms of [...] Read more.
The growing general interest surrounding Cannabis sativa L. has led to a renewal in breeding and resulted in an impressive variability of chemotypical characteristics that required the division of cannabis into different recognized chemotypes. The chemotype V has been overlooked in terms of phytochemical composition due to the almost total absence of cannabinoids, on which biomedical attention is focused. Systematic approaches addressing diverse chemotypes are, however, needed to discriminate and define phytochemical aspects beyond cannabinoids. Such thoroughly characterized chemotypes guarantee blinding in controlled studies by mimicking the sensory properties of hemp and may help to unravel the “entourage effect”. Capitalizing on the ability of cannabis to synthesize a large number of non-cannabinoid phenolic compounds, we here investigated, for the first time, the composition of the Ermo chemotype V and identified new compounds: two dihydrophenanthrenes and the methoxy-dihydrodenbinobin. All three compounds suppress pro-inflammatory leukotriene biosynthesis in activated macrophage subtypes by targeting 5-lipoxygenase, but substantially differ in their capacity to elevate the levels of specialized pro-resolving lipid mediators and their precursors in M2 macrophages. We conclude that the discovered compounds likely contribute to the anti-inflammatory properties of Cannabis sativa L. chemotype V and might promote inflammation resolution by promoting a lipid mediator class switch. Full article
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Review

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21 pages, 2841 KiB  
Review
Cannabinol: History, Syntheses, and Biological Profile of the Greatest “Minor” Cannabinoid
by Chiara Maioli, Daiana Mattoteia, Hawraz Ibrahim M. Amin, Alberto Minassi and Diego Caprioglio
Plants 2022, 11(21), 2896; https://doi.org/10.3390/plants11212896 - 28 Oct 2022
Cited by 14 | Viewed by 6110
Abstract
Cannabis (Cannabis sativa L.) is an outstanding source of bioactive natural products, with more than 150 different phytocannabinoids isolated throughout the decades; however, studies of their bioactivity have historically concentrated on the so-called “big four” [∆9-THC (1a), CBD [...] Read more.
Cannabis (Cannabis sativa L.) is an outstanding source of bioactive natural products, with more than 150 different phytocannabinoids isolated throughout the decades; however, studies of their bioactivity have historically concentrated on the so-called “big four” [∆9-THC (1a), CBD (2a), CBG (3a) and CBC (4a)]. Among the remaining products, which have traditionally been referred to as “minor cannabinoids”, cannabinol (CBN, 5a) stands out for its important repercussions and implications on the global scientific landscape. Throughout this review, we will describe why CBN (5a) deserves a prominent place within the so-called “cannabinome”, providing an overview on its history, the syntheses developed, and its bioactivity, highlighting its promising pharmacological potential and the significant impact that the study of its chemistry had on the development of new synthetic methodologies. Full article
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