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20 pages, 3118 KiB

Open AccessArticle

Diterpene Resin Acids and Olefins in Calabrian Pine (Pinus nigra subsp. laricio (Poiret) Maire) Oleoresin: GC-MS Profiling of Major Diterpenoids in Different Plant Organs, Molecular Identification and Expression Analysis of Diterpene Synthase Genes

by Enrica Alicandri, Stefano Covino, Bartolomeo Sebastiani, Anna Rita Paolacci, Maurizio Badiani, Francesco Manti, Carmelo Peter Bonsignore, Agostino Sorgonà and Mario Ciaffi

Plants 2021, 10(11), 2391; https://doi.org/10.3390/plants10112391 - 5 Nov 2021

Cited by 6 | Viewed by 2811

Abstract

A quali-quantitative analysis of diterpenoid composition in tissues obtained from different organs of Pinus nigra subsp. laricio (Poiret) Maire (Calabrian pine) was carried out. Diterpene resin acids were the most abundant diterpenoids across all the examined tissues. The same nine diterpene resin acids [...] Read more.

A quali-quantitative analysis of diterpenoid composition in tissues obtained from different organs of Pinus nigra subsp. laricio (Poiret) Maire (Calabrian pine) was carried out. Diterpene resin acids were the most abundant diterpenoids across all the examined tissues. The same nine diterpene resin acids were always found, with the abietane type prevailing on the pimarane type, although their quantitative distribution was found to be remarkably tissue-specific. The scrutiny of the available literature revealed species specificity as well. A phylogeny-based approach allowed us to isolate four cDNAs coding for diterpene synthases in Calabrian pine, each of which belonging to one of the four groups into which the d3 clade of the plants’ terpene synthases family can be divided. The deduced amino acid sequences allowed predicting that both monofunctional and bifunctional diterpene synthases are involved in the biosynthesis of diterpene resin acids in Calabrian pine. Transcript profiling revealed differential expression across the different tissues and was found to be consistent with the corresponding diterpenoid profiles. The isolation of the complete genomic sequences and the determination of their exon/intron structures allowed us to place the diterpene synthase genes from Calabrian pine on the background of current ideas on the functional evolution of diterpene synthases in Gymnosperms. Full article

(This article belongs to the Special Issue Plant Analytical Chemistry)

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21 pages, 5770 KiB

Open AccessArticle

Chemical Profiling, Pharmacological Insights and In Silico Studies of Methanol Seed Extract of Sterculia foetida

by Najmul Alam, Naureen Banu, Md. Arfin Ibn Aziz, Niloy Barua, Umme Ruman, Israt Jahan, Farhana Jahan Chy, Susmita Denath, Arkajyoti Paul, Md. Nazim Uddin Chy, Mohammed Aktar Sayeed, Talha Bin Emran and Jesus Simal-Gandara

Plants 2021, 10(6), 1135; https://doi.org/10.3390/plants10061135 - 3 Jun 2021

Cited by 13 | Viewed by 4605

Abstract

Sterculia foetida, also known as jangli badam in Bangladesh, is a traditionally used plant that has pharmacological activities. A qualitative phytochemical analysis was performed to assess the metabolites in a methanolic extract of S. foetida seeds (MESF), and the cytotoxic, thrombolytic, anti-arthritics, [...] Read more.

Sterculia foetida, also known as jangli badam in Bangladesh, is a traditionally used plant that has pharmacological activities. A qualitative phytochemical analysis was performed to assess the metabolites in a methanolic extract of S. foetida seeds (MESF), and the cytotoxic, thrombolytic, anti-arthritics, analgesic, and antipyretic activities were examined using in vitro, in vivo, and in silico experiments. Quantitative studies were performed through gas chromatography-mass spectroscopy (GC-MS) analysis. The brine shrimp lethality bioassays and clot lysis were performed to investigate the cytotoxic and thrombolytic activities, respectively. The anti-arthritics activity was assessed using the albumin denaturation assay. Analgesic activity was determined using the acetic acid-induced writhing test and the formalin-induced paw-licking test. A molecular docking study was performed, and an online tool was used to perform ADME/T (absorption, distribution, metabolism, and excretion/toxicity) and PASS (Prediction of Activity Spectra for Substances). GC-MS analysis identified 29 compounds in MESF, consisting primarily of phenols, terpenoids, esters, and other organic compounds. MESF showed moderate cytotoxic activity against brine shrimp and significant thrombolytic and anti-arthritics activities compared with the relative standards. The extract also showed a dose-dependent and significant analgesic and antipyretic activities. Docking studies showed that 1-azuleneethanol, acetate returned the best scores for the tested enzymes. These findings suggested that MESF represents a potent source of thrombolytic, anti-arthritic, analgesic, antipyretic agents with moderate cytotoxic effects. Full article

(This article belongs to the Special Issue Plant Analytical Chemistry)

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14 pages, 1482 KiB

Open AccessEditor’s ChoiceArticle

Metabolomic Analysis of Cannabinoid and Essential Oil Profiles in Different Hemp (Cannabis sativa L.) Phenotypes

by Marjeta Eržen, Iztok J. Košir, Miha Ocvirk, Samo Kreft and Andreja Čerenak

Plants 2021, 10(5), 966; https://doi.org/10.3390/plants10050966 - 12 May 2021

Cited by 27 | Viewed by 4929

Abstract

Hemp (Cannabis sativa L.) cannabinoids and terpenoids have therapeutic effects on human and animal health. Cannabis plants can often have a relatively high heterogeneity, which leads to different phenotypes that have different chemical profiles despite being from the same variety. Little information [...] Read more.

Hemp (Cannabis sativa L.) cannabinoids and terpenoids have therapeutic effects on human and animal health. Cannabis plants can often have a relatively high heterogeneity, which leads to different phenotypes that have different chemical profiles despite being from the same variety. Little information exists about cannabinoid and terpenoid profiles in different hemp phenotypes within the same variety. For this study, 11 phenotypes from three different varieties (“Carmagnola” selected (CS), “Tiborszallasi” (TS), and “Finola” selection (FS)) were analyzed. The components of essential oil (29) were analyzed using gas chromatography with flame ionization detection (GC/FID), and 10 different cannabinoids of each phenotype were determined using high-performance liquid chromatography (HPLC). Principal component analysis (PCA) and analysis of variance (ANOVA) showed that according to the components of essential oil, FS and TS plants were more uniform than CS plants, where there were great differences between CI and CII phenotypes. The content of cannabinoid CBD-A was the highest in all four FS phenotypes. By comparing cannabinoid profiles, FS was clearly separated from TS and CS, while these two varieties were not clearly distinguishable. Phenotypes TV and CI had the highest total content of Δ-9-THC, while all phenotypes of FS had the highest total content of CBD. The highest total content of CBG was determined in phenotype CI. Obtained results are useful for the development of new supplementary ingredients, for different pharmacy treatments, and for further breeding purposes. Full article

(This article belongs to the Special Issue Plant Analytical Chemistry)

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15 pages, 1206 KiB

Open AccessArticle

The Distribution of Minerals in Crucial Plant Parts of Various Elderberry (Sambucus spp.) Interspecific Hybrids

by Nataša Imenšek, Vilma Sem, Mitja Kolar, Anton Ivančič and Janja Kristl

Plants 2021, 10(4), 653; https://doi.org/10.3390/plants10040653 - 30 Mar 2021

Cited by 14 | Viewed by 3571

Abstract

In view of growing requirements of the food industry regarding elderberries (genus Sambucus), a need to increase their productivity and improve their chemical composition has emerged. With this purpose in mind, numerous elderberry interspecific hybrids have been created. In the present work, [...] Read more.

In view of growing requirements of the food industry regarding elderberries (genus Sambucus), a need to increase their productivity and improve their chemical composition has emerged. With this purpose in mind, numerous elderberry interspecific hybrids have been created. In the present work, the content of minerals in their crucial plant parts was studied. It was also investigated whether superior genotypes regarding the mineral composition of berries and inflorescences could be predicted at early stages of plant development. The results showed that elderberry leaves contained the highest amounts of Ca, Mg, Mn, Zn, and Sr, while K and P were predominant in fruit stalks. Fe and Al prevailed in roots and Cu in bark. Although berries showed lower mineral content compared to other plant parts, their mineral content is not negligible and could be comparable to other commonly consumed berries. Genotypes with a favorable mineral content of inflorescences and berries could be predicted on the basis of known mineral composition of their shoots and leaves. The study also indicates that S. nigra genotypes and the majority of interspecific hybrids analyzed are suitable for further genetic breeding or cultivation. Full article

(This article belongs to the Special Issue Plant Analytical Chemistry)

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15 pages, 21974 KiB

Open AccessArticle

Spectroscopic and Molecular Methods to Differentiate Gender in Immature Date Palm (Phoenix dactylifera L.)

by Abdul Latif Khan, Ahmed Al-Harrasi, Muhammad Numan, Noor Mazin AbdulKareem, Fazal Mabood and Ahmed Al-Rawahi

Plants 2021, 10(3), 536; https://doi.org/10.3390/plants10030536 - 12 Mar 2021

Cited by 7 | Viewed by 4514

Abstract

Phoenix dactylifera (date palm) is a well-known nutritious and economically important fruit tree found in arid regions of the Middle East and North Africa. Being diploid, it has extremely high divergence in gender, where sex differentiation in immature date palms (Phoenix dactylifera [...] Read more.

Phoenix dactylifera (date palm) is a well-known nutritious and economically important fruit tree found in arid regions of the Middle East and North Africa. Being diploid, it has extremely high divergence in gender, where sex differentiation in immature date palms (Phoenix dactylifera L.) has remained an enigma in recent years. Herein, new robust infrared (near-infrared reflectance spectroscopy (NIRS) and Fourier transform infrared attenuated total reflectance (FTIR/ATR)) and nuclear magnetic resonance (NMR) spectroscopy methods coupled with extensive chemometric analysis were used to identify the sex differentiation in immature date palm leaves. NIRS/FTIR reflectance and ¹H-NMR profiling suggested that the signals of monosaccharides (glucose and fructose) and/or disaccharides (maltose and sucrose) play key roles in sex differentiation. The three kinds of spectroscopic data were clearly differentiated among known and unknown male and female leaves via principal component and partial least square discriminant analyses. Furthermore, sex-specific genes and molecular markers obtained from the lower halves of LG12 chromosomes showed enhanced transcript accumulation of mPdIRDP52, mPdIRDP50, and PDK101 in females compared with in males. The phylogeny showed that the mPdIRD033, mPdIRD031, and mPdCIR032 markers formed distinctive clades with more than 70% similarity in gender differentiation. The three robust analyses provide an alternative tool to differentiate sex in date palm trees, which offers a solution to the long-standing challenge of dioecism and could enhance in situ tree propagation programs. Full article

(This article belongs to the Special Issue Plant Analytical Chemistry)

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18 pages, 1763 KiB

Open AccessEditor’s ChoiceArticle

Comparative Study of Chemical Composition and Antioxidant Activity of Essential Oils and Crude Extracts of Four Characteristic Zingiberaceae Herbs

by Milena Ivanović, Kaja Makoter and Maša Islamčević Razboršek

Plants 2021, 10(3), 501; https://doi.org/10.3390/plants10030501 - 8 Mar 2021

Cited by 48 | Viewed by 6549

Abstract

The ginger family (Zingiberaceae) includes plants that are known worldwide to have a distinctive smell and taste, which are often used as spices in the kitchen, but also in various industries (pharmaceutical, medical, and cosmetic) due to their proven biological activity. [...] Read more.

The ginger family (Zingiberaceae) includes plants that are known worldwide to have a distinctive smell and taste, which are often used as spices in the kitchen, but also in various industries (pharmaceutical, medical, and cosmetic) due to their proven biological activity. The aim of this study was to investigate and compare the chemical composition and antioxidant activity (AA) of essential oils (EOs) of four characteristic ginger species: Elettaria cardamomum L. Maton (cardamom), Curcuma Longa L. (turmeric), Zingiber Officinale Roscoe (ginger), and Alpinia Officinarum Hance (galangal). Furthermore, the total phenolic content (TPC) and AA of crude extracts obtained after using ultrasound-assisted extraction (UAE) and different extraction solvents (80% ethanol, 80% methanol and water) were evaluated. A total of 87 different chemical components were determined by GC-MS/MS in the EOs obtained after hydrodistillation, 14 of which were identified in varying amounts in all EOs. The major compounds found in cardamom, turmeric, ginger, and galangal were α-terpinyl acetate (40.70%), β-turmerone (25.77%), α-zingiberene (22.69%) and 1,8-cineol (42.71%), respectively. In general, 80% ethanol was found to be the most effective extracting solvent for the bioactivities of the investigated species from the Zingiberaceae family. Among the crude extracts, ethanolic extract of galangal showed the highest TPC value (63.01 ± 1.06 mg GA g⁻¹ DW), while the lowest TPC content was found in cardamom water extract (1.04 ± 0.29 mg GA g⁻¹ DW). The AA evaluated by two different assays (ferric-reducing antioxidant power-FRAP and the scavenging activity of the cationic ABTS radical) proved that galangal rhizome is the plant with the highest antioxidant potential. In addition, no statistical difference was found between the AA of turmeric and ginger extracts, while cardamom rhizome was again inferior. In contrast to the crude extracts, the EOs resulted in significantly lower ABTS and FRAP values, with turmeric EO showing the highest AA. Full article

(This article belongs to the Special Issue Plant Analytical Chemistry)

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14 pages, 1450 KiB

Open AccessArticle

Plukenetia huayllabambana Fruits: Analysis of Bioactive Compounds, Antibacterial Activity and Relative Action Mechanisms

by Armel Jackson Seukep, Minxia Fan, Satyajit Dey Sarker, Victor Kuete and Ming-Quan Guo

Plants 2020, 9(9), 1111; https://doi.org/10.3390/plants9091111 - 28 Aug 2020

Cited by 7 | Viewed by 3247

Abstract

Plukenetia huayllabambana is an edible plant traditionally used to cure wounds and various infections. The present work assessed, for the first time, the antibacterial efficacy of solvent fractions from P. huayllabambana fruits. The crude methanol extract was obtained applying ultrasound-assisted extraction, followed by [...] Read more.

Plukenetia huayllabambana is an edible plant traditionally used to cure wounds and various infections. The present work assessed, for the first time, the antibacterial efficacy of solvent fractions from P. huayllabambana fruits. The crude methanol extract was obtained applying ultrasound-assisted extraction, followed by partitioning through successive depletion among solvents of increasing polarity to yield fractions (n-hexane, dichloromethane, ethyl acetate, and n-butanol). The minimal inhibitory concentration (MIC) was determined following antibacterial testing, using the broth microdilution technique against a panel of drug-resistant Gram-negative and Gram-positive bacteria. Possible modes of action of the most active fraction were also investigated. Gas chromatography–mass spectrometry (GC–MS) was used to identify phytocompounds that may account for the recorded activities. Methanol, n-hexane (PH-n-Hex), and ethyl acetate extracts inhibited 100% of studied bacteria, with the recorded MIC ranging from 0.125–1 mg/mL. PH-n-Hex appeared as the most active partition, exerting a bacteriostatic effect. PH-n-Hex probably acts by interfering with bacterial biofilm formation, proton pumps, and bacterial cell membrane integrity. The GC–MS analysis of PH-n-Hex led to the identification of 11 potentially bioactive components, including fatty acids, phytosterol, and diterpene alcohol as major ones. P. huayllabambana can be considered as a plant of pharmacological value—a source of potent anti-infective drug entities. Full article

(This article belongs to the Special Issue Plant Analytical Chemistry)

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Review

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29 pages, 1076 KiB

Open AccessEditor’s ChoiceReview

Innovative Extraction Techniques Using Deep Eutectic Solvents and Analytical Methods for the Isolation and Characterization of Natural Bioactive Compounds from Plant Material

by Milena Ivanović, Maša Islamčević Razboršek and Mitja Kolar

Plants 2020, 9(11), 1428; https://doi.org/10.3390/plants9111428 - 24 Oct 2020

Cited by 115 | Viewed by 16250

Abstract

The growing interest of the food, pharmaceutical and cosmetics industries in naturally occurring bioactive compounds or secondary plant metabolites also leads to a growing demand for the development of new and more effective analysis and isolation techniques. The extraction of bioactive compounds from [...] Read more.

The growing interest of the food, pharmaceutical and cosmetics industries in naturally occurring bioactive compounds or secondary plant metabolites also leads to a growing demand for the development of new and more effective analysis and isolation techniques. The extraction of bioactive compounds from plant material has always been a challenge, accompanied by increasingly strict control requirements for the final products and a growing interest in environmental protection. However, great efforts have been made in this direction and today a considerable number of innovative extraction techniques have been developed using green, environmentally friendly solvents. These solvents include the deep eutectic solvents (DES) and their natural equivalents, the natural deep eutectic solvents (NADES). Due to their adjustable physical-chemical properties and their green character, it is expected that DES/NADES could be the most widely used solvents in the future, not only in extraction processes but also in other research areas such as catalysis, electrochemistry or organic synthesis. Consequently, this review provided an up-to-date systematic overview of the use of DES/NADES in combination with innovative extraction techniques for the isolation of bioactive compounds from various plant materials. The topicality of the field was confirmed by a detailed search on the platform WoS (Web of Science), which resulted in more than 100 original research papers on DES/NADES for bioactive compounds in the last three years. Besides the isolation of bioactive compounds from plants, different analytical methods are presented and discussed. Full article

(This article belongs to the Special Issue Plant Analytical Chemistry)

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