Phytochemical Analyses of Secondary Metabolites of Aromatic, Medicinal and Food Plants

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

Deadline for manuscript submissions: 31 August 2024 | Viewed by 6365

Special Issue Editors


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Guest Editor
Faculty of Pharmacy, Free University of Brussels, Av. Frankin Roosevelt, 50, 1050 Brussels, Belgium
Interests: extraction techniques; GCMS; natural products; phytochemistry

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Guest Editor
Department of Food and Drug, University of Parma, Parco Area delle Scienze 27/A, 43124 Parma, Italy
Interests: edible flowers; ornamental plants; postharvest; plant physiology; bioactive compounds; volatile organic compounds; in vitro tissue culture and plant propagation; nutraceuticals; functional food
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Special Issue Information

Dear Colleagues,

Plant secondary metabolites (PSMs) are small organic molecules characterized by different molecular structures and several biological functions. These molecules are essential for plants to interact with the ecosystem in which they live, protecting them from both biotic and abiotic stresses, attracting pollinators, and taking part in symbiotic interactions, thus increasing plant survival rate. Environmental, geographical, morphogenetic, and genetic factors can qualitatively and quantitatively affect PSMs; therefore, their amount and type can vary significantly between plants within the same genera, species, and population.

Aromatic, medicinal, and food plants are historically known as pivotal sources of PSMs, and are currently exploited as drugs, perfumes and fragrances, natural dyes, spice and food flavoring, food preservatives, and natural ingredient in cosmetics or food supplements.

Today, there is a growing focus on green and innovative methods for extracting metabolites, high-performance identification technologies for PSMs in plants, and determining how they can be externally induced for various purposes, as well as  identifying their volatile organic compounds (VOCs) profile, chemotaxonomy, functional foods, and metabolomics.

This Special Issue will cover research on the phytochemical composition of cultivated and wild aromatic, medicinal, and food plants, with an emphasis on their aromatic profile and phytonutritional content. Papers concerning innovative extraction, isolation, and identification methodologies, PSMs’ bioactive properties, and industrial uses are also welcome.

Dr. Basma Najar
Dr. Ilaria Marchioni
Guest Editors

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Keywords

  • volatile organic compounds
  • essential oils
  • nutraceuticals
  • bioactive properties
  • secondary metabolites
  • phytochemistry
  • metabolomic
  • extraction techniques

Published Papers (6 papers)

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Research

24 pages, 525 KiB  
Article
Exploring the Volatile Composition and Antibacterial Activity of Edible Flower Hydrosols with Insights into Their Spontaneous Emissions and Essential Oil Chemistry
by Basma Najar, Ylenia Pieracci, Filippo Fratini, Laura Pistelli, Barbara Turchi, Dario Varriale, Luisa Pistelli, Maria Francesca Bozzini and Ilaria Marchioni
Plants 2024, 13(8), 1145; https://doi.org/10.3390/plants13081145 (registering DOI) - 19 Apr 2024
Abstract
In the circular economy framework, hydrosols, by-products of the essential oil industry, are gaining attention for their potential in waste reduction and resource reuse. This study analyzed hydrosols from six edible flowers, investigating their chemical composition (VOC-Hyd) and antibacterial properties alongside volatile organic [...] Read more.
In the circular economy framework, hydrosols, by-products of the essential oil industry, are gaining attention for their potential in waste reduction and resource reuse. This study analyzed hydrosols from six edible flowers, investigating their chemical composition (VOC-Hyd) and antibacterial properties alongside volatile organic compounds of fresh flowers (VOC-Fs) and essential oils (EOs). Antirrhinum majus exhibited ketones as major VOC-Fs (62.6%) and VOC-Hyd (41.4%), while apocarotenoids dominated its EOs (68.0%). Begonia cucullata showed alkanes (33.7%) and aldehydes (25.7%) as primary VOC-Fs, while alkanes were prevalent in both extracts (65.6% and 91.7% in VOC-Hyd and in EOs, respectively). Calandula officinalis had monoterpenoids in VOC-Fs and VOC-Hyd (89.3% and 49.7%, respectively), while its EOs were rich in sesquiterpenoids (59.7%). Dahlia hortensis displayed monoterpenoid richness in both VOC-Fs and extracts. Monocots species’ VOC-Fs (Polianthes tuberosa, Tulbaghia cominsii) were esters-rich, replaced by monoterpenoids in VOC-Hyd. P. tuberosa EO maintained ester richness, while T. cominsii EOs contained a significant percentage of sulfur compounds (38.1%). Antibacterial assays indicated comparable minimum inhibitory concentration profiles across VOC-Hyd: B. calcullata and P. tuberosa against Staphylococcus aureus and Salmonella enterica ser. typhimurium, T. cominsii against Escherichia coli and S. enterica, A. majus and C. officinalis against S. aureus, and D. hortensis against S. enterica. Full article
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17 pages, 2559 KiB  
Article
Ozone Treatment as an Approach to Induce Specialized Compounds in Melissa officinalis Plants
by Giulia Scimone, Maria Giovanna Carucci, Samuele Risoli, Claudia Pisuttu, Lorenzo Cotrozzi, Giacomo Lorenzini, Cristina Nali, Elisa Pellegrini and Maike Petersen
Plants 2024, 13(7), 933; https://doi.org/10.3390/plants13070933 - 23 Mar 2024
Viewed by 564
Abstract
Plants are constantly subjected to environmental changes that deeply affect their metabolism, leading to the inhibition or synthesis of “specialized” compounds, small organic molecules that play a fundamental role in adaptative responses. In this work, Melissa officinalis L. (an aromatic plant broadly cultivated [...] Read more.
Plants are constantly subjected to environmental changes that deeply affect their metabolism, leading to the inhibition or synthesis of “specialized” compounds, small organic molecules that play a fundamental role in adaptative responses. In this work, Melissa officinalis L. (an aromatic plant broadly cultivated due to the large amounts of secondary metabolites) plants were exposed to realistic ozone (O3) dosages (80 ppb, 5 h day−1) for 35 consecutive days with the aim to evaluate its potential use as elicitor of specialized metabolite production. Ozone induced stomatal dysfunction throughout the whole experiment, associated with a low photosynthetic performance, a decrease in the potential energy conversion activity of PSII, and an alteration in the total chlorophyll content (−35, −36, −10, and −17% as average compared to the controls, respectively). The production of hydrogen peroxide at 7 days from the beginning of exposure (+47%) resulted in lipid peroxidation and visible injuries. This result suggests metabolic disturbance within the cell and a concomitant alteration in cell homeostasis, probably due to a limited activation of antioxidative mechanisms. Moderate accumulated doses of O3 triggered the accumulation of hydroxycinnamic acids and the up-regulation of the genes encoding enzymes involved in rosmarinic acid, phenylpropanoid, and flavonoid biosynthesis. While high accumulated doses of O3 significantly enhanced the content of hydroxybenzoic acid and flavanone glycosides. Our study shows that the application of O3 at the investigated concentration for a limited period (such as two/three weeks) may become a useful tool to stimulate bioactive compounds production in M. officinalis. Full article
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12 pages, 4355 KiB  
Article
The Impact of Harvesting Mechanization on Oolong Tea Quality
by Junling Zhou, Shuilian Gao, Zhenghua Du, Tongda Xu, Chao Zheng and Ying Liu
Plants 2024, 13(4), 552; https://doi.org/10.3390/plants13040552 - 18 Feb 2024
Viewed by 752
Abstract
Mechanization is the inevitable future of tea harvesting, but its impact on tea chemistry and quality remains uncertain. Our study examines untargeted metabolomic data from 185 oolong tea products (Tieguanyin) made from leaves harvested by hand or machine based on UPLC-QToF-MS analysis. The [...] Read more.
Mechanization is the inevitable future of tea harvesting, but its impact on tea chemistry and quality remains uncertain. Our study examines untargeted metabolomic data from 185 oolong tea products (Tieguanyin) made from leaves harvested by hand or machine based on UPLC-QToF-MS analysis. The data revealed a minimum 50% loss for over half of the chemicals in the machine-harvested group, including catechins, theaflavin, gallic acid, chlorogenic acid, and kaempferol-3-gluocside. Integrating sensory evaluation, OPLS-DA identified the six most important metabolites as significant contributors to sensory decline caused by harvesting mechanization. Furthermore, our research validates the possibility of using DD-SIMCA modelling with untargeted metabolomic data for distinguishing handpicked from machine-harvested tea products. The model was able to achieve 93% accuracy. This study provides crucial insights into the chemical and sensory shifts during mechanization, along with tools to manage and monitor these changes. Full article
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12 pages, 1265 KiB  
Article
Authentication of Fennel, Star Anise, and Anise Essential Oils by Gas Chromatography (GC/MS) and Stable Isotope Ratio (GC/IRMS) Analyses
by Brett J. Murphy, Tyler M. Wilson, Emma A. Ziebarth, Christopher R. Bowerbank and Richard E. Carlson
Plants 2024, 13(2), 214; https://doi.org/10.3390/plants13020214 - 12 Jan 2024
Viewed by 1387
Abstract
The aromatic compound (E)-anethol is widely used in the flavor, fragrance, and medicinal industries. This compound is commonly produced through steam distillation of fennel, star anise, and anise seed. Given the cost of production, these natural and authentic essential oils are [...] Read more.
The aromatic compound (E)-anethol is widely used in the flavor, fragrance, and medicinal industries. This compound is commonly produced through steam distillation of fennel, star anise, and anise seed. Given the cost of production, these natural and authentic essential oils are commonly adulterated with lower-cost natural materials or synthetic alternatives. The current study investigates essential oil profiles (gas chromatography/mass spectrometry) and stable isotope ratios (gas chromatography/isotope ratio mass spectrometry) of the abundant compound (E)-anethol in both authentic reference standards (n = 15) and commercially available samples (n = 30). This multifaceted analytical approach establishes techniques for ensuring the authenticity of essential oil sources of (E)-anethol and was then used to evaluate the current essential oil market sources of (E)-anethol. These findings report that adulteration of (E)-anethol-containing natural products takes various forms, and a multifaceted analytical approach is recommended for authentication. Of the commercial samples analyzed for this report, 27% were adulterated. Full article
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17 pages, 2877 KiB  
Article
Phytochemical Profiling and Biological Potential of Prunus dulcis Shell Extracts
by Talel Ben Khadher, Sameh Sassi-Aydi, Samir Aydi, Mohamed Mars and Jalloul Bouajila
Plants 2023, 12(14), 2733; https://doi.org/10.3390/plants12142733 - 23 Jul 2023
Cited by 1 | Viewed by 1391
Abstract
Prunus dulcis is one of the most widely cultivated species in the world. Its fruit (almond) is rich in various nutritious and bioactive compounds that exert several beneficial effects. The aim of this study was to determine the chemical profile and evaluate the [...] Read more.
Prunus dulcis is one of the most widely cultivated species in the world. Its fruit (almond) is rich in various nutritious and bioactive compounds that exert several beneficial effects. The aim of this study was to determine the chemical profile and evaluate the biological potential in vitro of almond shell extracts. The chemical analysis of shell extracts led to the identification of 15 compounds by HPLC-DAD, of which 11 were first detected in the almond plant. Twenty-six volatile compounds were identified by the GC-MS technique; among them, seven were firstly detected in the studied plant. For the biological activities, the extracts demonstrated moderate inhibition potential against the antioxidant, antidiabetic, and cytotoxic activities. The methanol extract at 50 µg/mL showed the highest antioxidant (45%) and antidiabetic activities (45% against alpha-glucosidase and 31% against alpha-amylase extracts), while the cyclohexane and dichloromethane at 50 µg/mL showed the highest cytotoxic activity towards Hela (32.2% with cyclohexane) and RAW 264-7 (45% with dichloromethane). Overall, these findings demonstrate the potential of almond shell extracts as a source of bioactive compounds that could be applied in the pharmaceutical and medical fields. Full article
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15 pages, 3568 KiB  
Article
Antibacterial Activity of the Essential Oil of Piper tuberculatum Jacq. Fruits against Multidrug-Resistant Strains: Inhibition of Efflux Pumps and β-Lactamase
by Lucas Yure Santos da Silva, Cicera Laura Roque Paulo, Talysson Felismino Moura, Daniel Sampaio Alves, Renata Torres Pessoa, Isaac Moura Araújo, Cícera Datiane de Morais Oliveira-Tintino, Saulo Relison Tintino, Carla de Fatima Alves Nonato, José Galberto Martins da Costa, Jaime Ribeiro-Filho, Henrique Douglas Melo Coutinho, Grażyna Kowalska, Przemysław Mitura, Marek Bar, Radosław Kowalski and Irwin Rose Alencar de Menezes
Plants 2023, 12(12), 2377; https://doi.org/10.3390/plants12122377 - 19 Jun 2023
Cited by 5 | Viewed by 1413
Abstract
Antimicrobial resistance has become a growing public health concern in recent decades, demanding a search for new effective treatments. Therefore, this study aimed to elucidate the phytochemical composition and evaluate the antibacterial activity of the essential oil obtained from the fruits of Piper [...] Read more.
Antimicrobial resistance has become a growing public health concern in recent decades, demanding a search for new effective treatments. Therefore, this study aimed to elucidate the phytochemical composition and evaluate the antibacterial activity of the essential oil obtained from the fruits of Piper tuberculatum Jacq. (EOPT) against strains carrying different mechanisms of antibiotic resistance. Phytochemical analysis was performed using gas chromatography–mass spectrometry (GC/MS). The antibacterial activity of EOPT and its ability to inhibit antibiotic resistance was evaluated through the broth microdilution method. The GC-MS analysis identified 99.59% of the constituents, with β-pinene (31.51%), α-pinene (28.38%), and β-cis-ocimene (20.22%) being identified as major constituents. The minimum inhibitory concentration (MIC) of EOPT was determined to assess its antibacterial activity against multidrug-resistant strains of Staphylococcus aureus (IS-58, 1199B, K2068, and K4100). The compound showed a MIC of ≥ 1024 μg/mL, suggesting a lack of intrinsic antibacterial activity. However, when the EOPT was associated with antibiotics and EtBr, a significant decrease in antibiotic resistance was observed, indicating the modulation of efflux pump activity. This evidence was corroborated with the observation of increased fluorescent light emission by the bacterial strains, indicating the involvement of the NorA and MepA efflux pumps. Additionally, the significant potentiation of ampicillin activity against the S. aureus strain K4414 suggests the β-lactamase inhibitory activity of EOPT. These results suggest that the essential oil from P. tuberculatum fruits has antibiotic-enhancing properties, with a mechanism involving the inhibition of efflux pumps and β-lactamase in MDR S. aureus strains. These findings provide new perspectives on the potential use of EOPT against antibiotic resistance and highlight the importance of Piper species as sources of bioactive compounds with promising therapeutic activities against MDR bacteria. Nevertheless, further preclinical (in vivo) studies remain necessary to confirm these in vitro-observed results. Full article
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Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Title: Authentication of natural (E)-anethol sources by gas chromatography (GC/MS) and stable isotope (GC/IRMS) analysis
Authors: Brett J. Murphy*, Tyler M. Wilson, Emma A. Ziebarth, Chris Bowerbank, and Richard E. Carlson
Affiliation: D. Gary Young Research Institute
Abstract: The aromatic compound (E)-anethol is widely used in the flavor, fragrance, and medicinal industries. The compound is commonly produced through steam distillation of fennel, star anise, and anise seed. Given the cost of production, these natural and authentic essential oils are commonly adulterated with lower cost naturals or synthetic alternatives. The current study investigates essential oil profiles (GC/MS) and stable isotope ratios (GC/IRMS) of the abundant compound (E)-anethol in both authentic reference standards (n = 15) and commercially available samples (n = 30) to establish multifaceted techniques of ensuring authenticity and to evaluate the current essential oil market for sources of (E)-anethol. Findings suggest that adulteration of natural products takes various forms, occurs in 27% of analyzed commercial samples, and that an analytical approach with both GC/MS and GC/IRMS is best for authentication.

Title: Ozone sensitivity of Melissa officinalis plants to chronic exposure: the role of antioxidant mechanisms
Authors: Pisuttu, C.; Carucci, M.G.; Cotrozzi, L., Lorenzini, G., Nali, C., Pellegrini, E., Risoli, S., Scimone, G.
Affiliation: Department of Agriculture, Food and Environment, University of Pisa, Via del Borghetto 80, Pisa 56124, Italy
Abstract: Ozone (O3) represents a widespread tropospheric pollutant in industrialized countries, predicted to rise up to 42-84 ppb in 2100, and it provokes severe threats to animal and plant health, due to its strong oxidation potential. In this study, lemon balm (Melissa officinalis L.), a common aromatic plant widely cultivated as culinary and pharmaceutical herb, was exposed to realistic O3 dosages (80 ppb, 5 h day-1) for 5 consecutive weeks. Ecophysiological, biometric and biochemical parameters were investigated in order to assess the responses induced by predicted concentrations of this pollutant. Photosynthetic performance resulted significantly affected: net photosynthesis decreased already after 7 days from the beginning of the exposure (FBE) together with stomatal conductance (-48 and -36% if compared to controls, respectively). The presence of roundish and dark-blackish necrosis located in the interveinal adaxial areas of the leaves was observed simultaneously with the increase of hydrogen peroxide content already at 7 days FBE (+47%), reaching a peak at 35 days FBE (+62%), and malondialdehyde (a fundamental lipid peroxidation marker) accumulation at 14 days FBE (more than 3 fold-higher in comparison to controls), confirming the presence of oxidative burst. Simultaneously, treated plants showed the activation of the antioxidant activity systems, measured through oxygen radical absorption capacity, at 14 days FBE (+81%). At 14 and 28 days FBE an increase of phenylalanine ammonia lyase activity was observed (+ 100% and more than 1 fold-higher in comparison to controls, respectively). Consequently, all three phenolic acids analyzed (Rosmarinic, trans-Cinnamic and Protocatechuic acids) showed remarkable increases starting at 14 days FBE (+74%, 2 and 3 fold-higher in comparison to controls, respectively) and continuing until the end of the exposure. Similarly, flavonoids content also increased between 7 and 14 days FBE (as demonstrated by the high values of apigenin, esperidin and esperitin, more than 1 fold-higher on the average). Although the activation of antioxidant machinery, O3-exposed plants showed a drastically reduction in all biometric parameters evaluated, resulted as severely affected by the exposition to realistic O3 concentrations.

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