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Metabolites
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Secondary Metabolites from Plant Sources
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Secondary Metabolites from Plant Sources

A special issue of Metabolites (ISSN 2218-1989). This special issue belongs to the section "Plant Metabolism".

Deadline for manuscript submissions: closed (31 July 2023) | Viewed by 13864

Special Issue Editors

Dr. Howaida I. Abd-Alla

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Guest Editor
Department of Chemistry of Natural Compounds, National Research Center, Cairo, Egypt
Interests: natural products chemistry; aroma compounds and essential oils in plants; functional food ingredients; marine plants; biological activities
Dr. Mohamed Osman Radwan

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Guest Editor
Graduate School of Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan
Interests: organic chemistry; medicinal chemistry; drug design
Dr. Hari Prasad Devkota

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Guest Editor
Graduate School of Pharmaceutical Sciences, Kumamoto University, Kumamoto 860-8555, Japan
Interests: bioactive natural products; phytochemistry; inflammation; flavonoids; functional foods
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Research on plant secondary metabolites has significantly increased over the last century. These molecules represent an important source of active pharmaceuticals, flavors, and nutraceuticals. Various secondary metabolites are used as bioactive components of drugs and may significantly and beneficially impact animal and human health. Secondary metabolites from plant sources have been an abundant area of chemical investigation for many years, driving the development of both analytical chemistry and new synthetic reactions and methodologies. Interestingly, along with their effect on animal and human health, secondary metabolites could have a hand in the development of gene technology that permits modulation of certain components’ content. This multi-disciplinary field of research involves chemists, biochemists, and plant scientists, all of whom have contributed to our current understanding of these materials. This Special Issue of Metabolites, “Secondary Metabolites from Plant Sources,” is dedicated to studies exploring the latest discoveries and innovations in this field.

We are calling for manuscripts that address the following topics:

1) Chemistry of plant secondary metabolites;

2)  Various classes of secondary metabolites as the key drivers of the pharmacological actions of plants and their important uses;

3) Nature-based synthetic molecules using secondary metabolites and their activities;

4) Plant secondary metabolites with nutraceutical, cosmetic, agro, flavors, pharmaceutical, food additives, and other industrial values;

5) Biotechnological approaches to enhancing the production of plant secondary metabolites (induced mutation, salinity stress, endophytes impact, plant tissue culture approaches, hydroponics system of cultivation, etc.);

6) Advances and technical obstacles in the production of secondary metabolites from medicinal plants;

7) Microbial-mediated enhancement of bioactive secondary metabolites of plants;

8) Marine plants with unique and diverse secondary metabolites: chemistry and application of seagrasses and algae, the main types of marine plants;

9) Molecular mechanisms and physiological for the production of secondary metabolites in plants;

10) Application of bioinformatics for production of plant secondary metabolites;

11) Transcriptomics approaches for large-scale identification of genes involved in plant secondary metabolism;

12) Plant secondary metabolite content and metabolites’ impact on animal performance, health and welfare;

13) Approaches to enhancing agricultural sustainability by growing crops and forages with a diverse range of plant secondary metabolites.

Dr. Howaida I. Abd-Alla
Dr. Mohamed Osman Radwan
Dr. Hari Prasad Devkota
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. Metabolites is an international peer-reviewed open access monthly 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.

Published Papers (7 papers)

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Research

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19 pages, 2887 KiB  
Article
Improving the Production of Secondary Metabolites via the Application of Biogenic Zinc Oxide Nanoparticles in the Calli of Delonix elata: A Potential Medicinal Plant
by Mohamed Tarroum, Norah S. Alfarraj, Fahad Al-Qurainy, Abdulrahman Al-Hashimi, Salim Khan, Mohammad Nadeem, Abdalrhaman M. Salih and Hassan O. Shaikhaldein
Metabolites 2023, 13(8), 905; https://doi.org/10.3390/metabo13080905 - 02 Aug 2023
Cited by 2 | Viewed by 1265
Abstract
The implementation of nanotechnology in the field of plant tissue culture has demonstrated an interesting impact on in vitro plant growth and development. Furthermore, the plant tissue culture accompanying nanoparticles has been showed to be a reliable alternative for the biosynthesis of secondary [...] Read more.
The implementation of nanotechnology in the field of plant tissue culture has demonstrated an interesting impact on in vitro plant growth and development. Furthermore, the plant tissue culture accompanying nanoparticles has been showed to be a reliable alternative for the biosynthesis of secondary metabolites. Herein, the effectiveness of zinc oxide nanoparticles (ZnONPs) on the growth of Delonix elata calli, as well as their phytochemical profiles, were investigated. Delonix elata seeds were collected and germinated, and then the plant species was determined based on the PCR product sequence of ITS1 and ITS4 primers. Afterward, the calli derived from Delonix elata seedlings were subjected to 0, 10, 20, 30, 40, and 50 mg/L of ZnONPs. The ZnONPs were biologically synthesized using the Ricinus communis aqueous leaf extract, which acts as a capping and reducing agent, and zinc nitrate solution. The nanostructures of the biogenic ZnONPs were confirmed using different techniques like UV–visible spectroscopy (UV), zeta potential measurement, Fourier transform infrared spectra (FTIR), X-ray diffraction (XRD), and scanning electron microscopy (SEM). Adding 30 mg/L of ZnONPs to the MS media (containing 2.5 µM 2,4-D and 1 µM BAP) resulted in the highest callus fresh weight (5.65 g) compared to the control and other ZnONP treatments. Similarly, more phenolic accumulation (358.85 µg/g DW) and flavonoid (112.88 µg/g DW) contents were achieved at 30 mg/L. Furthermore, the high-performance liquid chromatography (HPLC) analysis showed significant increments in gallic acid, quercetin, hesperidin, and rutin in all treated ZnONP calli compared to the control. On the other hand, the gas chromatography and mass spectroscopy (GC-MS) analysis of the calli extracts revealed that nine phytochemical compounds were common among all extracts. Moreover, the most predominant compound found in calli treated with 20, 30, 40, and 50 mg/L of ZnONPs was bis(2-ethylhexyl) phthalate, with percentage areas of 27.33, 38.68, 22.66, and 17.98%, respectively. The predominant compounds in the control and in calli treated with 10 mg/L of ZnONPs were octadecanoic acid, 2-propenyl ester and heptanoic acid. In conclusion, in this study, green ZnONPs exerted beneficial effects on Delonix elata calli and improved their production of bioactive compounds, especially at a dose of 30 mg/L. Full article
(This article belongs to the Special Issue Secondary Metabolites from Plant Sources)
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24 pages, 3972 KiB  
Article
Protective Action Mechanisms of Launaea mucronata Extract and Its Nano-Formulation against Nephrotoxicity in Rats as Revealed via Biochemical, Histopathological, and UPLC-QTOF–MS/MS Analyses
by Amany A. El-Fadaly, Inas Y. Younis, Mohamed F. Abdelhameed, Yasmine H. Ahmed, Tamer I. M. Ragab, Abd El-Nasser G. El Gendy, Mohamed A. Farag, Abdelsamed I. Elshamy and Abdelbaset M. Elgamal
Metabolites 2023, 13(7), 786; https://doi.org/10.3390/metabo13070786 - 23 Jun 2023
Cited by 4 | Viewed by 1500
Abstract
Plants belonging to the Launaea genus have been extensively utilized ethnopharmacologically to treat a variety of diseases, including kidney disorders. Chromium is a common industrial pollutant that has been linked to kidney disease. The present work was designed for the investigation of the [...] Read more.
Plants belonging to the Launaea genus have been extensively utilized ethnopharmacologically to treat a variety of diseases, including kidney disorders. Chromium is a common industrial pollutant that has been linked to kidney disease. The present work was designed for the investigation of the UPLC-QTOF–MS/MS metabolite profile of the L. mucronate ethanolic extract (LME), along with assessing the mechanistic protective actions of LME and its nano-silver formulation (LMNS) against K2Cr2O7-induced nephrotoxicity in rats. LMNE was successfully biosynthesized and confirmed using UV–Visible (UV–Vis) spectroscopy and transmission electron microscopy (TEM). The nephroprotective effects of LME and LMNE was assessed in rats exposed to potassium dichromate (K2Cr2O7, 15 mg/kg BW) to cause nephrotoxicity. LME and LMNS, separately, were administered twice daily for 14 days at doses of 200 and 400 mg/kg BW, respectively. The kidney function, catalase, UGT, Nrf2, PGE2, Cox-2, ERK, and MAPK levels in renal tissue were all assessed, along with histopathological examinations for exploring their ameliorative effects. Forty-five bioactive metabolites were annotated belonging to flavonoids, phenolic and organic acids, coumarins, and fatty acids. Metabolite profiling revealed that chlorogenic acid, apigenin, and luteolin glycosides were the main phenolics, with chlorogenic acid-O-hexoside reported for the first time in LME. The findings revealed that the serum kidney function indicators (urea and creatinine) were markedly elevated in K2Cr2O7-intoxicated rats. Furthermore, inflammatory indicators (COX-2 and PGE2), MAPK, and ERK were all markedly elevated in kidney tissue, whereas catalase, UGT, and Nrf2 levels were downregulated. Histological and immunohistochemical assays confirmed the toxic effects of K2Cr2O7 in the kidneys. In contrast, the administration of LME and LMNS prior to K2Cr2O7 considerably improved the architecture of the renal tissue, while also restoring levels of most biochemical markers. Functioning via the inhibition of the MAPK/ERK pathway, activating Nrf2, and modifying the antioxidant and metabolic enzymes, LME and LMNS exerted their nephroprotective effects against K2Cr2O7-induced toxicity. Full article
(This article belongs to the Special Issue Secondary Metabolites from Plant Sources)
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19 pages, 15482 KiB  
Article
A Comprehensive Analysis to Elucidate the Effects of Spraying Mineral Elements on the Accumulation of Flavonoids in Epimedium sagittatum during the Harvesting Period
by Linlin Yang, Fei Zhang, Yueci Yan, Xupeng Gu, Shengwei Zhou, Xiuhong Su, Baoyu Ji, Hua Zhong and Chengming Dong
Metabolites 2023, 13(2), 294; https://doi.org/10.3390/metabo13020294 - 16 Feb 2023
Viewed by 1286
Abstract
The harvesting period is a critical period for the accumulation of flavonoids in the leaves of the important medicinal plant Epimedium sagittatum. In this study, we conducted an experiment on E. sagittatum leaves sprayed with mineral elements with the aim of improving [...] Read more.
The harvesting period is a critical period for the accumulation of flavonoids in the leaves of the important medicinal plant Epimedium sagittatum. In this study, we conducted an experiment on E. sagittatum leaves sprayed with mineral elements with the aim of improving the quality of the herbal leafage during the harvesting period. We elucidated the changes in flavonoids (icariin, epimedin A, epimedin B, and epimedin C) in E. sagittatum leaves. The sum of main flavonoids content reached a maximum (11.74%) at 20 days after the high-concentration Fe2+ (2500 mg·L−1) treatment. We analyzed the FT-IR spectra characteristics of E. sagittatum leaf samples using the FT-IR technique, and constructed an OPLS-DA model and identified characteristic peaks to achieve differentiated identification of E. sagittatum. Further, widely untargeted metabolomic analysis identified different classes of metabolites. As the most important characteristic flavonoids, the relative contents of icariin, icaritin, icariside I, and icariside II were found to be up-regulated by high-Fe2+ treatment. Our experimental results demonstrate that high-concentration Fe2+ treatment is an effective measure to increase the flavonoids content in E. sagittatum leaves during the harvesting period, which can provide a scientific basis for the improvement of E. sagittatum leaf cultivation agronomic measures. Full article
(This article belongs to the Special Issue Secondary Metabolites from Plant Sources)
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18 pages, 3906 KiB  
Article
Bark Beetles Utilize Ophiostomatoid Fungi to Circumvent Host Tree Defenses
by Rashaduz Zaman, Courtney May, Aziz Ullah and Nadir Erbilgin
Metabolites 2023, 13(2), 239; https://doi.org/10.3390/metabo13020239 - 06 Feb 2023
Cited by 7 | Viewed by 2022
Abstract
Bark beetles maintain symbiotic associations with a diversity of microbial organisms, including ophiostomatoid fungi. Studies have frequently reported the role of ophiostomatoid fungi in bark beetle biology, but how fungal symbionts interact with host chemical defenses over time is needed. We first investigated [...] Read more.
Bark beetles maintain symbiotic associations with a diversity of microbial organisms, including ophiostomatoid fungi. Studies have frequently reported the role of ophiostomatoid fungi in bark beetle biology, but how fungal symbionts interact with host chemical defenses over time is needed. We first investigated how inoculations by three fungal symbionts of mountain pine beetle affect the terpene chemistry of live lodgepole pine trees. We then conducted a complimentary laboratory experiment specifically measuring the host metabolite degradation by fungi and collected the fungal organic volatiles following inoculations with the same fungal species on lodgepole pine logs. In both experiments, we analyzed the infected tissues for their terpene chemistry. Additionally, we conducted an olfactometer assay to determine whether adult beetles respond to the volatile organic chemicals emitted from each of the three fungal species. We found that all fungi upregulated terpenes as early as two weeks after inoculations. Similarly, oxygenated monoterpene concentrations also increased by several folds (only in logs). A large majority of beetles tested showed a strong attraction to two fungal species, whereas the other fungus repelled the beetles. Together this study shows that fungal symbionts can alter host defense chemistry, assist beetles in overcoming metabolite toxicity, and provide possible chemical cues for bark beetle attraction. Full article
(This article belongs to the Special Issue Secondary Metabolites from Plant Sources)
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18 pages, 9736 KiB  
Article
Targeted Metabolome Profiling of Indonesian Shallots and Japanese Long-Day/Short-Day Bulb Onions
by Kanako Matsuse, Mostafa Abdelrahman, Nur Aeni Ariyanti, Fumitada Tsuji, Sho Hirata, Tetsuya Nakajima, Muneo Sato, Masami Yokota Hirai, Benya Manochai and Masayoshi Shigyo
Metabolites 2022, 12(12), 1260; https://doi.org/10.3390/metabo12121260 - 14 Dec 2022
Cited by 2 | Viewed by 2174
Abstract
In this study, targeted metabolome analysis was applied to identify the discriminative metabolites between Indonesian shallot landraces, Japanese long-day onion (LDO) varieties, and Japanese short-day onion (SDO) varieties. In total, 172 metabolite signal intensities were subjected to multivariate PLS-DA, VIP, and random forest [...] Read more.
In this study, targeted metabolome analysis was applied to identify the discriminative metabolites between Indonesian shallot landraces, Japanese long-day onion (LDO) varieties, and Japanese short-day onion (SDO) varieties. In total, 172 metabolite signal intensities were subjected to multivariate PLS-DA, VIP, and random forest modeling to gain further insight into genotype-specific metabolites. PLS-DA divides the examined genotypes into three different clusters, implying that shallot landraces exhibited a distinct metabolite profile compared with Japanese LDO and SDO varieties. The PLS-DA, VIP, and random forest results indicated that the shallot and LDO are richer in metabolite constituents in comparison with the SDO. Specifically, amino acids and organosulfur compounds were the key characteristic metabolites in shallot and LDO genotypes. The analysis of S-alk(en)yl-L-cysteine sulfoxide (ACSO) compounds showed higher accumulation in the shallot landraces relative to LDO and SDO varieties, which explains the stronger pungency and odor in shallots. In addition, the LDO showed higher ACSO content compared with the SDO, implying that long-day cultivation might enhance sulfur assimilation in the Japanese onion. The LDO ‘Super Kitamomiji’ and the shallots ‘Probolinggo’ and ‘Thailand’ showed higher ACSO content than other varieties, making it useful for Allium breeding to improve the flavor and stress tolerance of onions. Full article
(This article belongs to the Special Issue Secondary Metabolites from Plant Sources)
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18 pages, 10890 KiB  
Article
Study on the Regulation of Exogenous Hormones on the Absorption of Elements and the Accumulation of Secondary Metabolites in the Medicinal Plant Artemisia argyi Leaves
by Linlin Yang, Yueci Yan, Boyu Zhao, Huaming Xu, Xiuhong Su and Chengming Dong
Metabolites 2022, 12(10), 984; https://doi.org/10.3390/metabo12100984 - 17 Oct 2022
Cited by 5 | Viewed by 1785
Abstract
As an important medicinal plant, we still do not know the effect of exogenous hormones on absorption of elements and accumulation of secondary metabolites in Artemisia argyi leaves. In this work, we analyzed the difference in 21 elements absorbed by A. argyi leaves [...] Read more.
As an important medicinal plant, we still do not know the effect of exogenous hormones on absorption of elements and accumulation of secondary metabolites in Artemisia argyi leaves. In this work, we analyzed the difference in 21 elements absorbed by A. argyi leaves under three exogenous hormone (MeJA, SA and ABA) treatments, and also clarified the correlation between 21 elements and eight bioactive components. Different hormone treatments changed the absorption and enrichment of elements, and the composition also changed significantly. The contents of eight bioactive components changed significantly under different hormone treatments. When A. argyi was stimulated by exogenous hormones, the content of secondary metabolites was adjusted in the leaves through changes in the absorption and enrichment of elements. The widely untargeted metabolomic analysis further confirmed that ABA changes the metabolic direction of secondary metabolites in A. argyi leaves and stimulates the biosynthesis of multiple secondary metabolites including phenylpropanoids, flavonoids, terpenoids, alkaloids and others. These results provide a new perspective for the changes in element absorption and the mechanism of secondary metabolic components in A. argyi leaves under exogenous hormone treatments, and also deepen people’s understanding of the interaction mechanism between medicinal plants and hormones. Full article
(This article belongs to the Special Issue Secondary Metabolites from Plant Sources)
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Review

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21 pages, 4433 KiB  
Review
Chemical and Biological Properties of Three Poorly Studied Species of Lycium Genus—Short Review
by Maria da Graça Miguel
Metabolites 2022, 12(12), 1265; https://doi.org/10.3390/metabo12121265 - 15 Dec 2022
Cited by 6 | Viewed by 2038
Abstract
The genus Lycium belongs to the Solanaceae family and comprises more than 90 species distributed by diverse continents. Lycium barbarum is by far the most studied and has been advertised as a “superfood” with healthy properties. In contrast, there are some Lycium species [...] Read more.
The genus Lycium belongs to the Solanaceae family and comprises more than 90 species distributed by diverse continents. Lycium barbarum is by far the most studied and has been advertised as a “superfood” with healthy properties. In contrast, there are some Lycium species which have been poorly studied, although used by native populations. L. europaeum, L. intricatum and L. schweinfurthii, found particularly in the Mediterranean region, are examples of scarcely investigated species. The chemical composition and the biological properties of these species were reviewed. The biological properties of L. barbarum fruits are mainly attributed to polysaccharides, particularly complex glycoproteins with different compositions. Studies regarding these metabolites are practically absent in L. europaeum, L. intricatum and L. schweinfurthii. The metabolites isolated and identified belong mainly to polyphenols, fatty acids, polysaccharides, carotenoids, sterols, terpenoids, tocopherols, and alkaloids (L. europaeum); phenolic acids, lignans, flavonoids, polyketides, glycosides, terpenoids, tyramine derivatives among other few compounds (L. schweinfurthii), and esters of phenolic acids, glycosides, fatty acids, terpenoids/phytosterols, among other few compounds (L. intricatum). The biological properties (antioxidant, anti-inflammatory and cytotoxic against some cancer cell lines) found for these species were attributed to some metabolites belonging to those compound groups. Results of the study concluded that investigations concerning L. europaeum, L. intricatum and L. schweinfurthii are scarce, in contrast to L. barbarum. Full article
(This article belongs to the Special Issue Secondary Metabolites from Plant Sources)
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