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

Deadline for manuscript submissions: closed (20 July 2022) | Viewed by 20975

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Dr. Ioan Grozescu

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Guest Editor

CAICON Department, University Politehnica Timisoara, 300006 Timisoara, Romania
Interests: nanomaterials; natural compounds; structure of materials
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Prof. Dr. Maria Iorizzi

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Department of Biosciences and Territory, University of Molise, Contrada Fonte Lappone, 86090 Pesche, IS, Italy
Interests: natural products chemistry; NMR spectroscopy; mass spectrometry and GC-MS; medicinal plants; antioxidant activity; metabolomics
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Special Issue Information

Dear Colleagues,

This Special Issue is to highlight recent advances in spectral technique combinations in the investigation of natural compounds.

Structural elucidation of bioactive compounds is performed using different spectroscopic techniques, such as UV–Vis spectroscopy, FT-IR spectroscopy, or mass spectroscopy. The molecular structure of a specific compound can be identified based on its spectral information. For instance, in an FT-IR spectrum, absorbances from the functional group region correspond only to a certain class of compounds.

UV–Vis spectroscopy is extremely useful especially for colored natural organic compounds, or chromophores, quantitative measurements of a specific compound, food adulteration, food chemistry, etc.

Nuclear magnetic resonance (NMR) spectroscopy, through 1D-NMR and 2D-NMR experiments, is a central analytical technique in the identification of small molecules within natural products, but it also benefits numerous other downstream research fields, such as biology, chemical ecology, drug discovery and development, pharmacology, and the total chemical synthesis of natural products.

Today, NMR spectroscopy, with the use of chemometric data analysis of NMR spectra, has evolved to become a powerful complementary technique for the structural and functional characterization of the metabolome (metabolomic analysis), enabling the definition of complex mixtures of animal or plant origin.

The understanding of many biological processes is now possible through several other important techniques, including hyphenated methods, which combine NMR spectroscopy with mass spectrometry and chromatography.

Modern mass spectroscopy offers more information than nuclear magnetic resonance spectroscopy (NMR). Moreover, mass spectroscopy recently overcame one major limitation of NMR: the possibility to analyze a complex mixture of metabolites, as is the case with natural compounds. On the other hand, peaks in mass spectra correspond to a specific component with a unique m/z ratio and the heights of the peaks provide information on the relative abundance of that compound.

XRD spectroscopy is a modern technique used to characterize natural compounds from a molecular structure point of view. X-rays provide valuable detailed information on molecule stereochemistry and structure.

Energy-dispersive spectrometry provides information on element determination, endogenous or exogenous, in plants or animal tissue, cells, etc. Other methods, such as scanning electron microscopy (SEM), are also used to investigate plant surface topography and Raman spectroscopy.

We look forward to your contributions to this Special Issue, which may focus on but need not be limited to any of the topics outlined above.

Dr. Ioan Grozescu
Prof. Dr. Maria Iorizzi
Guest Editors

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. Plants 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

plant spectral information
UV–Vis spectroscopy
FT-IR spectroscopy
NMR spectroscopy
MS spectroscopy
XRD spectroscopy
Energy-dispersive spectrometry
Scanning electron microscope (SEM)

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Related Special Issue

Spectra Analysis and Plants Research 2.0 in Plants (13 articles)

Published Papers (9 papers)

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10 pages, 2690 KiB

Open AccessArticle

Chemical Composition and Histochemical Localization of Essential Oil from Wild and Cultivated Rhaponticum carthamoides Roots and Rhizomes

by Velislava Todorova, Stanislava Ivanova, Yoana Georgieva, Vanya Nalbantova, Diana Karcheva-Bahchevanska, Niko Benbassat, Martina S. Savova, Milen I. Georgiev and Kalin Ivanov

Plants 2022, 11(15), 2061; https://doi.org/10.3390/plants11152061 - 6 Aug 2022

Cited by 1 | Viewed by 2085

Abstract

Rhaponticum carthamoides (Willd.) Iljin is not only a source of phytosteroids and flavonoids, but is also source of essential oil (EO). This study evaluated the volatile metabolic constituents and histochemical localization of root and rhizome essential oils (EOs) from R. carthamoides populations wild-grown in Russia and cultivated in Bulgaria. The performed histochemical analysis confirmed the presence of lipophilic substances in the secretory ducts of the examined roots and rhizomes. Both EOs were obtained by hydrodistillation and further analyzed by gas chromatography with mass detection. The results showed differences between the chemical compositions of both EOs. Forty-six components were tentatively identified in R. carthamoides oil from the wild population, with β-selinene (4.77%), estragole (6.32%), D-carvone (6.37%), cyperene (8.78%), and ledene oxide (11.52%) being the major constituents. In the EO isolated from cultivated R. carthamoides, twenty-three compounds were tentatively identified, with humulene (7.68%), β-elemene (10.76%), humulene-1,2-epoxide (11.55%), ledene oxide (13.50%), and δ-elemene (19.08%) predominating. This is the first report describing the histolocalization and chemical profile of EO from R. carthamoides cultivated in Bulgaria. Further research on the cultivation of R. carthamoides in Bulgaria would affect the relationship between its chemical composition and pharmacological effects. Full article

(This article belongs to the Special Issue Spectra Analysis and Plants Research)

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17 pages, 6690 KiB

Open AccessArticle

4-Hydroxybenzoic Acid as an Antiviral Product from Alkaline Autoxidation of Catechinic Acid: A Fact to Be Reviewed

by Silvana Alfei, Debora Caviglia, Susanna Penco, Guendalina Zuccari and Fabio Gosetti

Plants 2022, 11(14), 1822; https://doi.org/10.3390/plants11141822 - 11 Jul 2022

Cited by 2 | Viewed by 2386 | Correction

Abstract

The dark brown mixture resulting from the autooxidation of catechinic acid (CA) (AOCA) has been reported to possess antiviral activity against Herpes Simplex Virus 1 and 2 (HSV-1 and HSV-2). Unfortunately, the constituents of AOCA were not separated or identified and the compound(s) responsible for AOCA’s antiviral activity remained unknown until recently. Colorless 4-hydroxy benzoic acid (4-HBA) has been reported as the main constituent (75%) of AOCA, and as being responsible for its antiviral activity. The findings seemed not to be reliable because of the existence in the literature of very different findings, because of the high concentration that was attributed to the supposed 4-HBA in the dark mixture, and because of the absence of essential analytical experiments to confirm 4-HBA in AOCA. Particularly, the AOCA chromatograms highlighting a peak attributable to 4-HBA, using commercial 4-HBA as a standard, is missing, as well as investigations concerning the antiviral activity of marketed 4-HBA. Therefore, in this study, to verify the exactness of the recent reports, we prepared CA from catechin and AOCA from CA, and the absence of 4-HBA in the mixture was first established by thin-layer chromatography (TLC), and then was confirmed by UHPLC–MS/MS, UV–Vis, and ATR–FTIR analyses. For further confirmation, the ATR–FTIR spectral data were processed by principal components analysis (PCA), which unequivocally established strong structural differences between 4-HBA and AOCA. Finally, while the antiviral effects of AOCA against HSV-2 were confirmed, a commercial sample of 4-HBA was completely inactive. Full article

(This article belongs to the Special Issue Spectra Analysis and Plants Research)

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23 pages, 8214 KiB

Open AccessEditor’s ChoiceArticle

Romanian Viscum album L.—Untargeted Low-Molecular Metabolomic Approach to Engineered Viscum–AuNPs Carrier Assembly

by Adina-Elena Segneanu, Catalin Nicolae Marin, Dumitru Daniel Herea, Ionut Stanusoiu, Cornelia Muntean and Ioan Grozescu

Plants 2022, 11(14), 1820; https://doi.org/10.3390/plants11141820 - 11 Jul 2022

Cited by 14 | Viewed by 2640

Abstract

Viscum is one of the most famous and appreciated medicinal plants in Europe and beyond. The symbiotic relationship with the host tree and various endogenous and ecological aspects are the main factors on which the viscum metabolites’ profiles depend. In addition, European traditional medicine mentions that only in two periods of the year (summer solstice and winter solstice) the therapeutic potential of the plant is at its maximum. Many studies have investigated the phytotherapeutic properties of viscum grown on different species of trees. However, studies on Romanian viscum are relatively few and refer mainly to the antioxidant and antiproliferative activity of mistletoe grown on Acer campestre, Fraxinus excelsior, Populus nigra, Malus domestica, or Robinia pseudoacacia. This study reports the first complete low-molecular-weight metabolite profile of Romanian wild-grown European viscum. A total of 140 metabolites were identified under mass spectra (MS) positive mode from 15 secondary metabolite categories: flavonoids, amino acids and peptides, terpenoids, phenolic acids, fatty acids, organic acids, nucleosides, alcohols and esters, amines, coumarins, alkaloids, lignans, steroids, aldehydes, and miscellaneous. In addition, the biological activity of each class of metabolite is discussed. The development of a simple and selective phyto-engineered AuNPs carrier assembly is reported and an evaluation of the nanocarrier system’s morpho-structure is performed, to capitalize on the beneficial properties of viscum and AuNPs. Full article

(This article belongs to the Special Issue Spectra Analysis and Plants Research)

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13 pages, 2260 KiB

Open AccessArticle

Spectroscopic Evidence of Thermal Changes in Plant Oils during Deep-Frying—Chemical and Infrared Studies

by Lucyna Dymińska, Abduladhim Moamer Moftah Albegar, Wojciech Sąsiadek, Edyta Kucharska, Adam Zając and Jerzy Hanuza

Plants 2022, 11(14), 1813; https://doi.org/10.3390/plants11141813 - 9 Jul 2022

Cited by 7 | Viewed by 1713

Abstract

For this study, the thermal degradation of palm, coconut, rice bran, and rapeseed (canola) oils was studied. Products formed during deep-frying were identified using chemical methods and these results were verified with those derived from FT-IR (Fourier-transform infrared spectroscopy) studies. Mathematically processed spectral data were analyzed in terms of the breaking of double bonds, the decomposition of the carotenoids, and the reduction of the C=O carbonyl group. Clearly visible changes in the position and intensity of some bands were used for explaining the structural changes in the studied oils. These changes prove that during the heating of the oils, decomposition of the plant fat into fatty acids appears, together with the reduction of the number of certain bonds (e.g., C=C, =C-H, and C=O) and cracking of the acylglycerol chains. The iodine values of the heated oils, determined from the FT-IR spectra measurements, show a significant decrease in their degree of unsaturation level. These effects, visible in the FT-IR spectra, confirm the chemical and structural changes derived from the chemical and physicochemical studies of the plant oils. The influence of heating time on the band intensity of proteins was also studied. Full article

(This article belongs to the Special Issue Spectra Analysis and Plants Research)

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21 pages, 1838 KiB

Open AccessArticle

Phytochemical Analysis of the Methanolic Extract and Essential Oil from Leaves of Industrial Hemp Futura 75 Cultivar: Isolation of a New Cannabinoid Derivative and Biological Profile Using Computational Approaches

by Simona De Vita, Claudia Finamore, Maria Giovanna Chini, Gabriella Saviano, Vincenzo De Felice, Simona De Marino, Gianluigi Lauro, Agostino Casapullo, Francesca Fantasma, Federico Trombetta, Giuseppe Bifulco and Maria Iorizzi

Plants 2022, 11(13), 1671; https://doi.org/10.3390/plants11131671 - 24 Jun 2022

Cited by 17 | Viewed by 3921

Abstract

Cannabis sativa L. is a plant belonging to the Cannabaceae family, cultivated for its psychoactive cannabinoid (Δ⁹-THC) concentration or for its fiber and nutrient content in industrial use. Industrial hemp shows a low Δ⁹-THC level and is a valuable source of phytochemicals, mainly represented by cannabinoids, flavones, terpenes, and alkaloids, with health-promoting effects. In the present study, we investigated the phytochemical composition of leaves of the industrial hemp cultivar Futura 75, a monoecious cultivar commercially used for food preparations or cosmetic purposes. Leaves are generally discarded, and represent waste products. We analyzed the methanol extract of Futura 75 leaves by HPLC and NMR spectroscopy and the essential oil by GC-MS. In addition, in order to compare the chemical constituents, we prepared the water infusion. One new cannabinoid derivative (1) and seven known components, namely, cannabidiol (2), cannabidiolic acid (3), β-cannabispirol (4), β-cannabispirol (5), canniprene (6), cannabiripsol (7), and cannflavin B (8) were identified. The content of CBD was highest in all preparations. In addition, we present the outcomes of a computational study focused on elucidating the role of 2α-hydroxy-Δ^3,7-cannabitriol (1), CBD (2), and CBDA (3) in inflammation and thrombogenesis. Full article

(This article belongs to the Special Issue Spectra Analysis and Plants Research)

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11 pages, 11017 KiB

Open AccessArticle

Prediction and Comparisons of Turpentine Content in Slash Pine at Different Slope Positions Using Near-Infrared Spectroscopy

by Qifu Luan, Shu Diao, Honggang Sun, Xianyin Ding and Jingmin Jiang

Plants 2022, 11(7), 914; https://doi.org/10.3390/plants11070914 - 29 Mar 2022

Cited by 5 | Viewed by 1848

Abstract

Pine resin is one of the best known and most exploited non-wood products. Resin is a complex mixture of terpenes produced by specialized cells that are dedicated to tree defense. Chemical defenses are plastic properties, and concentrations of chemical defenses can be adjusted based on environmental factors, such as resource availability. The slope orientation (south/sunny or north/shady) and the altitude of the plantation site have significant effects on the soil nutrient and the plant performance, whereas little is known about how the slope affects the pine resin yield and its components. In total, 1180 slash pines in 18 plots at different slope positions were established to determine the effects on the α- and β-pinene content and resin production of the slash pine. The near-infrared spectroscopy (NIR) technique was developed to rapidly and economically predict the turpentine content for each sample. The results showed that the best partial least squares regression (PLS) models for α- and β-pinene content prediction were established via the combined treatment of multiplicative scatter correction–significant multivariate correlation (MSC–sMC). The prediction models based on sMC spectra for α- and β-pinene content have an R² of 0.82 and 0.85 and an RMSE of 0.96 and 0.82, respectively, and they were successfully implemented in turpentine prediction in this research. The results also showed that a barren slope position (especially mid-slope) could improve the α-pinene and β-pinene content and resin productivity of slash pine, and the β-pinene content in the resin had more variances in this research. Full article

(This article belongs to the Special Issue Spectra Analysis and Plants Research)

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21 pages, 9727 KiB

Open AccessArticle

Comparative Determination of Phenolic Compounds in Arabidopsis thaliana Leaf Powder under Distinct Stress Conditions Using Fourier-Transform Infrared (FT-IR) and Near-Infrared (FT-NIR) Spectroscopy

by Rahul Joshi, Ramaraj Sathasivam, Praveen Kumar Jayapal, Ajay Kumar Patel, Bao Van Nguyen, Mohammad Akbar Faqeerzada, Sang Un Park, Seung Hyun Lee, Moon S. Kim, Insuck Baek and Byoung-Kwan Cho

Plants 2022, 11(7), 836; https://doi.org/10.3390/plants11070836 - 22 Mar 2022

Cited by 18 | Viewed by 2470

Abstract

The increasing interest in plant phenolic compounds in the past few years has become necessary because of their several important physicochemical properties. Thus, their identification through non-destructive methods has become crucial. This study carried out comparative non-destructive measurements of Arabidopsis thaliana leaf powder sample phenolic compounds using Fourier-transform infrared and near-infrared spectroscopic techniques under six distinct stress conditions. The prediction analysis of 600 leaf powder samples under different stress conditions (LED lights and drought) was performed using PLSR, PCR, and NAS-based HLA/GO regression analysis methods. The results obtained through FT-NIR spectroscopy yielded the highest correlation coefficient (

R_{p}^{2}

) value of 0.999, with a minimum error (RMSEP) value of 0.003 mg/g, based on the PLSR model using the MSC preprocessing method, which was slightly better than the correlation coefficient (

R_{p}^{2}

) value of 0.980 with an error (RMSEP) value of 0.055 mg/g for FT-IR spectroscopy. Additionally, beta coefficient plots present spectral differences and the identification of important spectral signatures sensitive to the phenolic compounds in the measured powdered samples. Thus, the obtained results demonstrated that FT-NIR spectroscopy combined with partial least squares regression (PLSR) and suitable preprocessing method has a solid potential for non-destructively predicting phenolic compounds in Arabidopsis thaliana leaf powder samples. Full article

(This article belongs to the Special Issue Spectra Analysis and Plants Research)

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13 pages, 4378 KiB

Open AccessArticle

Investigation of Calcium Forms in Lichens from Travertine Sites

by Dajana Ručová, Tamara Đorđević, Matej Baláž, Marieluise Weidinger, Ingeborg Lang, Andrej Gajdoš and Michal Goga

Plants 2022, 11(5), 620; https://doi.org/10.3390/plants11050620 - 25 Feb 2022

Cited by 4 | Viewed by 2005

Abstract

Lichens are symbiotic organisms with an extraordinary capability to colonise areas of extreme climate and heavily contaminated sites, such as metal-rich habitats. Lichens have developed several mechanisms to overcome the toxicity of metals, including the ability to bind metal cations to extracellular sites of symbiotic partners and to subsequently form oxalates. Calcium is an essential alkaline earth element that is important in various cell processes. Calcium can serve as a metal ligand but can be toxic at elevated concentrations. This study investigated calcium-rich and calcium-poor sites and the lichen species that inhabit them (Cladonia sp.). The calcium content of these lichen species were analyzed, along with localized calcium oxalate formed in thalli collected from each site. The highest concentration of calcium was found in the lichen squamules, which can serve as a final deposit for detoxification. Interestingly, the highest content of calcium in Cladonia furcata was localized to the upper part of the thallus, which is the youngest. The produced calcium oxalates were species-specific. Whewellite (CaC₂O₄∙H₂O) was formed in the case of C. furcata and weddellite (CaC₂O₄∙2H₂O) was identified in C. foliacea. Full article

(This article belongs to the Special Issue Spectra Analysis and Plants Research)

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4 pages, 550 KiB

Open AccessCorrection

Correction: Alfei et al. 4-Hydroxybenzoic Acid as an Antiviral Product from Alkaline Autoxidation of Catechinic Acid: A Fact to Be Reviewed. Plants 2022, 11, 1822

by Silvana Alfei, Debora Caviglia, Susanna Penco, Guendalina Zuccari and Fabio Gosetti

Plants 2023, 12(8), 1635; https://doi.org/10.3390/plants12081635 - 13 Apr 2023

Viewed by 706

Abstract

In the original publication [...] Full article

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