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15 pages, 1058 KiB

Open AccessArticle

Assessment of the Nutritional Value of Stems and Leaves of Australian Adzuki Bean

by Joel B. Johnson, Ryan J. Batley, Pasmita Neupane, Surya P. Bhattarai, Tieneke Trotter, Diogo Fleury Azevedo Costa and Mani Naiker

Metabolites 2023, 13(10), 1062; https://doi.org/10.3390/metabo13101062 - 9 Oct 2023

Viewed by 1178

Abstract

Adzuki bean has recently been proposed as a viable dual-purpose (grain-and-graze) crop for the Northern regions of Australia because of its successful use in semi-arid regions and its nitrogen fixation capacity to improve soil fertility and animal nutrition. However, there are very few [...] Read more.

Adzuki bean has recently been proposed as a viable dual-purpose (grain-and-graze) crop for the Northern regions of Australia because of its successful use in semi-arid regions and its nitrogen fixation capacity to improve soil fertility and animal nutrition. However, there are very few studies on the phytochemical composition and nutritional value of the non-seed material. This study investigated the phenolic composition of the parts grown in the vegetative phase (leaves and stems) of nine Australian adzuki bean varieties for the first time. The total phenolic content (TPC) of the stem material (157–406 mg GAE/100 g) was 23–217% higher than that of commercial livestock feed, while the TPC of the leaf material (1158–1420 mg GAE/100 g) was 9–11 times higher. Using tandem liquid chromatography mass spectrometry (LC-MS), the major phenolic compounds identified were rutin, luteolin, salicylic acid, and quercetin-3-glucoside. The leaf and stem materials showed high levels of apparent in vitro dry matter digestibility, with no significant difference in total gas or methane production compared to lucerne hay. The results suggest that adzuki bean vegetative materials could be a high-value livestock fodder and support pursuing further in-depth studies into their nutritional value for livestock. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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10 pages, 1019 KiB

Open AccessArticle

Clarifying the Configuration of Pandamine by an Extensive Spectroscopic Reinvestigation of the Authentic 1964 Sample

by Pascal Retailleau, Evodie Numbi Wa Ilunga, Véronique Fontaine, Jean-François Gallard and Pierre Le Pogam

Metabolites 2023, 13(4), 470; https://doi.org/10.3390/metabo13040470 - 24 Mar 2023

Cited by 3 | Viewed by 1554

Abstract

Since its partial configurational assignment in 1964, pandamine has not been isolated or obtained by total synthesis. For decades, different works representing the structure of pandamine for illustrative purposes have lent different configurations to this molecule, causing tenacious confusion about the structure of [...] Read more.

Since its partial configurational assignment in 1964, pandamine has not been isolated or obtained by total synthesis. For decades, different works representing the structure of pandamine for illustrative purposes have lent different configurations to this molecule, causing tenacious confusion about the structure of this ansapeptide. A comprehensive spectroscopic analysis of the authentic pandamine sample led to the complete and unambiguous assignment of its configuration, 59 years after its isolation. In addition to ascertaining and completing the initial structural deductions by a state-of-the-art set of analytical techniques, the purpose of this study is also to clarify the literature in a context in which various erroneous structures have been attributed to pandamine for half a century. While fully in agreement with Goutarel’s conclusions, the specific example of pandamine should serve as a cautionary tale to any chemist interested in natural products, encouraging access to initial structural assignments rather than relying solely on subsequent, possibly erroneous, structure depictions of a natural product. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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15 pages, 4471 KiB

Open AccessArticle

Probing Serum Albumins and Cyclodextrins as Binders of the Mycotoxin Metabolites Alternariol-3-Glucoside, Alternariol-9-Monomethylether-3-Glucoside, and Zearalenone-14-Glucuronide

by Miklós Poór, Beáta Lemli, Péter Vilmányi, Ágnes Dombi, Zoltán Nagymihály, Eszter Borbála Both, Nándor Lambert, Tamás Czömpöly and Lajos Szente

Metabolites 2023, 13(3), 446; https://doi.org/10.3390/metabo13030446 - 18 Mar 2023

Cited by 2 | Viewed by 1730

Abstract

Mycotoxins are toxic metabolites of molds. Chronic exposure to alternariol, zearalenone, and their metabolites may cause the development of endocrine-disrupting and carcinogenic effects. Alternariol-3-glucoside (AG) and alternariol-9-monomethylether-3-glucoside (AMG) are masked derivatives of alternariol. Furthermore, in mammals, zearalenone-14-glucuronide (Z14Glr) is one of the most [...] Read more.

Mycotoxins are toxic metabolites of molds. Chronic exposure to alternariol, zearalenone, and their metabolites may cause the development of endocrine-disrupting and carcinogenic effects. Alternariol-3-glucoside (AG) and alternariol-9-monomethylether-3-glucoside (AMG) are masked derivatives of alternariol. Furthermore, in mammals, zearalenone-14-glucuronide (Z14Glr) is one of the most dominant metabolites of zearalenone. In this study, we examined serum albumins and cyclodextrins (CDs) as potential binders of AG, AMG, and Z14Glr. The most important results/conclusions were as follows: AG and AMG formed moderately strong complexes with human, bovine, porcine, and rat albumins. Rat albumin bound Z14Glr approximately 4.5-fold stronger than human albumin. AG–albumin and Z14Glr–albumin interactions were barely influenced by the environmental pH, while the formation of AMG–albumin complexes was strongly favored by alkaline conditions. Among the mycotoxin–CD complexes examined, AMG–sugammadex interaction proved to be the most stable. CD bead polymers decreased the mycotoxin content of aqueous solutions, with moderate removal of AG and AMG, while weak extraction of Z14Glr was observed. In conclusion, rat albumin is a relatively strong binder of Z14Glr, and albumin can form highly stable complexes with AMG at pH 8.5. Therefore, albumins can be considered as affinity proteins with regard to the latter mycotoxin metabolites. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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23 pages, 3257 KiB

Open AccessArticle

Corinthian Currants Supplementation Restores Serum Polar Phenolic Compounds, Reduces IL-1beta, and Exerts Beneficial Effects on Gut Microbiota in the Streptozotocin-Induced Type-1 Diabetic Rat

by Vasiliki Kompoura, Ioanna Prapa, Paraskevi B. Vasilakopoulou, Gregoria Mitropoulou, Grigorios Nelios, Evangelos Balafas, Nikolaos Kostomitsopoulos, Antonia Chiou, Vaios T. Karathanos, Eugenia Bezirtzoglou, Yiannis Kourkoutas and Amalia E. Yanni

Metabolites 2023, 13(3), 415; https://doi.org/10.3390/metabo13030415 - 11 Mar 2023

Cited by 5 | Viewed by 2632

Abstract

The present study aimed at investigating the possible benefits of a dietary intervention with Corinthian currants, a rich source of phenolic compounds, on type 1 diabetes (T1D) using the animal model of the streptozotocin-(STZ)-induced diabetic rat. Male Wistar rats were randomly assigned into [...] Read more.

The present study aimed at investigating the possible benefits of a dietary intervention with Corinthian currants, a rich source of phenolic compounds, on type 1 diabetes (T1D) using the animal model of the streptozotocin-(STZ)-induced diabetic rat. Male Wistar rats were randomly assigned into four groups: control animals, which received a control diet (CD) or a diet supplemented with 10% w/w Corinthian currants (CCD), and diabetic animals, which received a control diet (DCD) or a currant diet (DCCD) for 4 weeks. Plasma biochemical parameters, insulin, polar phenolic compounds, and inflammatory factors were determined. Microbiota populations in tissue and intestinal fluid of the caecum, as well as fecal microbiota populations and short-chain fatty acids (SCFAs), were measured. Fecal microbiota was further analyzed by 16S rRNA sequencing. The results of the study showed that a Corinthian currant-supplemented diet restored serum polar phenolic compounds and decreased interleukin-1b (IL-1b) (p < 0.05) both in control and diabetic animals. Increased caecal lactobacilli counts (p < 0.05) and maintenance of enterococci levels within normal range were observed in the intestinal fluid of the DCCD group (p < 0.05 compared to DCD). Higher acetic acid levels were detected in the feces of diabetic rats that received the currant diet compared to the animals that received the control diet (p < 0.05). Corinthian currant could serve as a beneficial dietary component in the condition of T1D based on the results coming from the animal model of the STZ-induced T1D rat. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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28 pages, 4585 KiB

Open AccessArticle

Betaxanthin Profiling in Relation to the Biological Activities of Red and Yellow Beta vulgaris L. Extracts

by Aneta Spórna-Kucab, Anna Tekieli, Agnieszka Grzegorczyk, Łukasz Świątek, Anastazja Boguszewska and Krystyna Skalicka-Woźniak

Metabolites 2023, 13(3), 408; https://doi.org/10.3390/metabo13030408 - 9 Mar 2023

Cited by 5 | Viewed by 2451

Abstract

Beta vulgaris L. is an edible plant with health-beneficial activities. The profile of betaxanthins is more complex than previously described in beetroot cultivars. Twenty-four betaxanthins were detected in extracts of the peel and flesh of five cultivars by HPLC-DAD-ESI-MS, of which two new [...] Read more.

Beta vulgaris L. is an edible plant with health-beneficial activities. The profile of betaxanthins is more complex than previously described in beetroot cultivars. Twenty-four betaxanthins were detected in extracts of the peel and flesh of five cultivars by HPLC-DAD-ESI-MS, of which two new betaxanthins (arginine-Bx and ornithine-Bx) were detected for the first time in B. vulgaris cultivars. The content of betaxanthins in the studied cultivars decreased in the Tytus > Ceryl > Chrobry > Forono > Boldor sequence. The highest content of compounds (1231 mg/100 g DE) was observed in the Tytus cultivar (peel). The peel of B. vulgaris, which is often considered a waste, appeared to be a richer source of betaxanthins compared to its flesh. Antibacterial and antifungal activities were determined against twenty-three microorganisms. Tytus (peel) showed a moderate or good bactericidal effect, especially against the majority of Gram-positive bacteria as well as against most of the tested fungi (MIC = 0.125–0.5 mg/mL) and additionally characterized by low cytotoxicity towards non-cancerous cells (CC₅₀ = 405 μg/mL, CC₅₀—50% cytotoxic concentration). Tytus flesh also showed a high cytotoxicity value against human cervical adenocarcinoma (HeLa), with CC₅₀ of 282 μg/mL. Correlation analysis was used to determine the relationship between the betaxanthin profiles and antimicrobial and anticancer activities. Arginine-Bx, proline-Bx, and tryptophan-Bx were indicated as active against HeLa and the colon cancer cell line (RKO), while asparagine-Bx and phenylalanine-Bx was responsible for activity against all tested bacterial and yeast species. The significant effectiveness and safety of these beetroots make indicated compounds promising applicants as antimicrobial and anticancer agents. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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19 pages, 4061 KiB

Open AccessArticle

Antioxidant, Antibacterial, Anti-Inflammatory, and Antiproliferative Activity of Sorghum Lignin (Sorghum bicolor) Treated with Ultrasonic Pulses

by Linda Yareth Reyna-Reyna, Beatriz Montaño-Leyva, Dora Valencia, Francisco Javier Cinco-Moroyoqui, Ricardo Iván González-Vega, Ariadna Thalía Bernal-Mercado, Manuel G. Ballesteros-Monrreal, Mayra A. Mendez-Encinas and Carmen Lizette Del-Toro-Sánchez

Metabolites 2023, 13(3), 394; https://doi.org/10.3390/metabo13030394 - 8 Mar 2023

Cited by 7 | Viewed by 1839

Abstract

This investigation aimed to determine the effect of high-power ultrasonic pulses on the antioxidant, antibacterial, and antiproliferative activity of sorghum (Sorghum bicolor) lignin. A lignin yield of 7.35% was obtained using the organosolv method. Additionally, the best conditions of the ultrasonic [...] Read more.

This investigation aimed to determine the effect of high-power ultrasonic pulses on the antioxidant, antibacterial, and antiproliferative activity of sorghum (Sorghum bicolor) lignin. A lignin yield of 7.35% was obtained using the organosolv method. Additionally, the best conditions of the ultrasonic pulses were optimized to obtain a more significant increase in antioxidant capacity, resulting in 10 min for all treatments, with amplitudes of 20% for DPPH and FRAP, 18% for ABTS, and 14% for total phenols. The effect of ultrasonic pulses was mainly observed with FRAP (1694.88 µmol TE/g), indicating that the main antioxidant mechanism of lignin is through electron transport. Sorghum lignin with and without ultrasonic pulses showed high percentages of hemolysis inhibition (>80%) at concentrations of 0.003 to 0.33 mg/mL. The AB blood group and, in general, all Rh- groups are the most susceptible to hemolysis. Lignin showed high anti-inflammatory potential due to heat and hypotonicity (>82%). A higher antimicrobial activity of lignin on Escherichia coli bacteria was observed. The lignins evaluated without sonication and sonication presented higher activity in the cell line PC-3. No effect was observed on the lignin structure with the FT-IR technique between sonication and non-sonication; however, the organosolv method helped extract pure lignin according to HPLC. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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24 pages, 11515 KiB

Open AccessArticle

NMR Metabolomics and DNA Sequencing of Escherichia coli and Staphylococcus aureus Cultures Treated with Hydrolyzable Tannins

by Valtteri Virtanen, Elina Puljula, Gemma Walton, Martin J. Woodward and Maarit Karonen

Metabolites 2023, 13(3), 320; https://doi.org/10.3390/metabo13030320 - 21 Feb 2023

Cited by 3 | Viewed by 1942

Abstract

Escherichia coli and Staphylococcus aureus are globally among the most prominent bacterial strains associated with antibacterial resistance-caused deaths. Naturally occurring polyphenols, such as hydrolyzable tannins, have been shown to potently inhibit E. coli and S. aureus. The current study investigated the metabolome [...] Read more.

Escherichia coli and Staphylococcus aureus are globally among the most prominent bacterial strains associated with antibacterial resistance-caused deaths. Naturally occurring polyphenols, such as hydrolyzable tannins, have been shown to potently inhibit E. coli and S. aureus. The current study investigated the metabolome changes of E. coli and S. aureus cultures after treatments with different hydrolyzable tannins using an NMR metabolomics approach. Additionally, the effect of these tannin treatments influencing a more complex bacterial system was studied in a biomimetic setting with fecal samples inoculated into the growth medium. Metabolite concentration changes were observed in all three scenarios: E. coli, S. aureus, and fecal batch culture. The metabolome of E. coli was more altered by the tannin treatments than S. aureus when compared to control cultures. A dimeric hydrolyzable tannin, rugosin D, was found to be the most effective of the studied compounds in influencing bacterial metabolome changes and in inhibiting E. coli and S. aureus growth. It was also observed that the tannin structure should have both hydrophobic and hydrophilic regions to efficiently influence E. coli and S. aureus growth. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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15 pages, 8144 KiB

Open AccessArticle

Metabolites That Confirm Induction and Release of Dormancy Phases in Sweet Cherry Buds

by Klaus-P. Götz and Frank-M. Chmielewski

Metabolites 2023, 13(2), 231; https://doi.org/10.3390/metabo13020231 - 3 Feb 2023

Cited by 5 | Viewed by 1567

Abstract

Here we report on metabolites found in a targeted profiling of ‘Summit’ flower buds for nine years, which could be indicators for the timing of endodormancy release (t₁) and beginning of ontogenetic development (t₁*). Investigated metabolites included chrysin, arabonic [...] Read more.

Here we report on metabolites found in a targeted profiling of ‘Summit’ flower buds for nine years, which could be indicators for the timing of endodormancy release (t₁) and beginning of ontogenetic development (t₁*). Investigated metabolites included chrysin, arabonic acid, pentose acid, sucrose, abscisic acid (ABA), and abscisic acid glucose ester (ABA-GE). Chrysin and water content showed an almost parallel course between leaf fall and t₁*. After ‘swollen bud’, water content raised from ~60 to ~80% at open cluster, while chrysin content decreased and lost its function as an acetylcholinesterase inhibitor. Both parameters can be suitable indicators for t₁*. Arabonic acid showed a clear increase after t₁*. Pentose acid would be a suitable metabolite to identify t₁ and t₁*, but would not allow describing the ecodormancy phase, because of its continuously low value during this time. Sucrose reached a maximum during ecodormancy and showed a significant correlation with air temperature, which confirms its cryoprotective role in this phase. The ABA content showed maximum values during endodormancy and decreased during ecodormancy, reaching 50% of its content t₁ at t₁*. It appears to be the key metabolite to define the ecodormancy phase. The ABA-GE was present at all stages and phases and was much higher than the ABA content and is a readily available storage pool in cherry buds. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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21 pages, 3468 KiB

Open AccessArticle

Antihyperalgesic and Antiallodynic Effects of Amarisolide A and Salvia amarissima Ortega in Experimental Fibromyalgia-Type Pain

by Gabriel Fernando Moreno-Pérez, María Eva González-Trujano, Alberto Hernandez-Leon, María Guadalupe Valle-Dorado, Alejandro Valdés-Cruz, Noé Alvarado-Vásquez, Eva Aguirre-Hernández, Hermelinda Salgado-Ceballos and Francisco Pellicer

Metabolites 2023, 13(1), 59; https://doi.org/10.3390/metabo13010059 - 30 Dec 2022

Cited by 4 | Viewed by 2262

Abstract

Salvia amarissima Ortega is an endemic species of Mexico used in folk medicine to alleviate pain and as a nervous tranquilizer. The S. amarissima extract and one of its abundant metabolites, identified and isolated through chromatographic techniques, were investigated to obtain scientific evidence [...] Read more.

Salvia amarissima Ortega is an endemic species of Mexico used in folk medicine to alleviate pain and as a nervous tranquilizer. The S. amarissima extract and one of its abundant metabolites, identified and isolated through chromatographic techniques, were investigated to obtain scientific evidence of its potential effects to relieve nociplastic pain such as fibromyalgia. Then, the extract and amarisolide A (3–300 mg/kg, i.p.) were pharmacologically evaluated in reserpine-induced fibromyalgia-type chronic pain and in depressive-like behavior (as a common comorbidity) by using the forced swimming test in rats. The 5-HT_1A serotonin receptor (selective antagonist WAY100635, 1 mg/kg, i.p.) was explored after the prediction of a chemical interaction using in silico analysis to look for a possible mechanism of action of amarisolide A. Both the extract and amarisolide A produced significant and dose-dependent antihyperalgesic and antiallodynic effects in rats, as well as significant antidepressive behavior without sedative effects when the antinociceptive dosages were used. The 5-HT_1A serotonin receptor participation was predicted by the in silico descriptors and was corroborated in the presence of WAY100635. In conclusion, S. amarissima possesses antihyperalgesic, antiallodynic, and anti-depressive activities, partially due to the presence of amarisolide A, which involves the 5-HT_1A serotonin receptor. This pharmacological evidence suggests that S. amarissima and amarisolide A are both potential alternatives to relieve pain-like fibromyalgia. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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11 pages, 1821 KiB

Open AccessArticle

Interactions of Mycotoxin Alternariol with Cytochrome P450 Enzymes and OATP Transporters

by Eszter Fliszár-Nyúl, Orsolya Ungvári, Ágnes Dombi, Csilla Özvegy-Laczka and Miklós Poór

Metabolites 2023, 13(1), 45; https://doi.org/10.3390/metabo13010045 - 28 Dec 2022

Cited by 5 | Viewed by 2154

Abstract

Alternariol (AOH) is an emerging mycotoxin produced by Alternaria strains. The acute toxicity of the mycotoxin is low; however, chronic exposure to AOH may result in the development of endocrine disruptor and/or carcinogenic effects. The toxicokinetic properties of AOH have barely been characterized. [...] Read more.

Alternariol (AOH) is an emerging mycotoxin produced by Alternaria strains. The acute toxicity of the mycotoxin is low; however, chronic exposure to AOH may result in the development of endocrine disruptor and/or carcinogenic effects. The toxicokinetic properties of AOH have barely been characterized. Therefore, in this study, we aimed to investigate its interactions with CYP (1A2, 2C9, 2C19, 2D6, and 3A4) enzymes and OATP (1A2, 1B1, 1B3, and 2B1) transporters employing in vitro enzyme assays and OATP overexpressing cells, respectively. Our results demonstrated that AOH is a strong inhibitor of CYP1A2 (IC₅₀ = 0.15 μM) and CYP2C9 (IC₅₀ = 7.4 μM). Based on the AOH depletion assays in the presence of CYP enzymes, CYP1A2 is mainly involved, while CYP2C19 is moderately involved in the CYP-catalyzed biotransformation of the mycotoxin. AOH proved to be a strong inhibitor of each OATP transporter examined (IC₅₀ = 1.9 to 5.4 μM). In addition, both direct and indirect assays suggest the involvement of OATP1B1 in the cellular uptake of the mycotoxin. These findings promote the deeper understanding of certain toxicokinetic interactions of AOH. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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14 pages, 1239 KiB

Open AccessArticle

Coumarins of Lovage Roots (Levisticum officinale W.D.J.Koch): LC-MS Profile, Quantification, and Stability during Postharvest Storage

by Daniil N. Olennikov

Metabolites 2023, 13(1), 3; https://doi.org/10.3390/metabo13010003 - 20 Dec 2022

Cited by 9 | Viewed by 2169

Abstract

Lovage (Levisticum officinale W.D.J. Koch) is a known aromatic apiaceous species that is widely used as a culinary and medicinal plant. Traditionally, more scientific attention has been paid to lovage volatiles, while other groups of compounds have been underutilized. In this study, [...] Read more.

Lovage (Levisticum officinale W.D.J. Koch) is a known aromatic apiaceous species that is widely used as a culinary and medicinal plant. Traditionally, more scientific attention has been paid to lovage volatiles, while other groups of compounds have been underutilized. In this study, metabolites of fresh lovage roots were investigated by liquid chromatography–mass spectrometry, and 25 compounds were identified, including coumarins as basic components and minor hydroxycinnamates; most were detected for the first time in the plant. Four major coumarins (including apterin, xanthotoxin, isopimpinellin, and pimpinellin) were successfully separated by a validated HPLC–PDA method, and the fresh roots of seven lovage cultivars as well as the dry roots of commercial lovage were quantified. The coumarin content deviation was 1.7–2.9 mg/g in the fresh roots and 15–24 mg/g in the dry roots. A variation in the coumarin level was found during storage of the fresh lovage roots at chill and room temperatures, while storage of the dried roots at room temperature showed the lowest loss of target compounds. This new information about the metabolites of lovage indicates the prospects of the plant roots as a source of dietary coumarins. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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14 pages, 2632 KiB

Open AccessArticle

Proteomic and Metabolomic Evaluation of Insect- and Herbicide-Resistant Maize Seeds

by Weixiao Liu, Lixia Meng, Weiling Zhao, Zhanchao Wang, Chaohua Miao, Yusong Wan and Wujun Jin

Metabolites 2022, 12(11), 1078; https://doi.org/10.3390/metabo12111078 - 7 Nov 2022

Cited by 2 | Viewed by 1627

Abstract

Label-free quantitative proteomic (LFQ) and widely targeted metabolomic analyses were applied in the safety evaluation of three genetically modified (GM) maize varieties, BBL, BFL-1, and BFL-2, in addition to their corresponding non-GM parent maize. A total of 76, 40, and 25 differentially expressed [...] Read more.

Label-free quantitative proteomic (LFQ) and widely targeted metabolomic analyses were applied in the safety evaluation of three genetically modified (GM) maize varieties, BBL, BFL-1, and BFL-2, in addition to their corresponding non-GM parent maize. A total of 76, 40, and 25 differentially expressed proteins (DEPs) were screened out in BBL, BFL-1, and BFL-2, respectively, and their abundance compared was with that in their non-GM parents. Kyoto Encyclopedia of Genes and Genomes (KEGG) pathway enrichment analysis showed that most of the DEPs participate in biosynthesis of secondary metabolites, biosynthesis of amino acids, and metabolic pathways. Metabolomic analyses revealed 145, 178, and 88 differentially accumulated metabolites (DAMs) in the BBL/ZH58, BFL-1/ZH58, and BFL-2/ZH58×CH72 comparisons, respectively. KEGG pathway enrichment analysis showed that most of the DAMs are involved in biosynthesis of amino acids, and in arginine and proline metabolism. Three co-DEPs and 11 co-DAMs were identified in the seeds of these GM maize lines. The proteomic profiling of seeds showed that the GM maize varieties were not dramatically different from their non-GM control. Similarly, the metabolomic profiling of seeds showed no dramatic changes in the GM/non-GM maize varieties compared with the GM/GM and non-GM/non-GM maize varieties. The genetic background of the transgenic maize was found to have some influence on its proteomic and metabolomic profiles. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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15 pages, 3657 KiB

Open AccessArticle

Assessment of Tissue Specific Distribution and Seasonal Variation of Alkaloids in Alstonia scholaris

by Rohit Mahar, Nagarajan Manivel, Sanjeev Kanojiya, Dipak K. Mishra and Sanjeev K. Shukla

Metabolites 2022, 12(7), 607; https://doi.org/10.3390/metabo12070607 - 30 Jun 2022

Cited by 4 | Viewed by 2238

Abstract

Alstonia scholaris is a well-known source of alkaloids and widely recognized for therapeutic purposes to treat the ailments in human and livestock. However, the composition and production of alkaloids vary due to tissue specific metabolism and seasonal variation. This study investigated alkaloids in [...] Read more.

Alstonia scholaris is a well-known source of alkaloids and widely recognized for therapeutic purposes to treat the ailments in human and livestock. However, the composition and production of alkaloids vary due to tissue specific metabolism and seasonal variation. This study investigated alkaloids in leaves, stems, trunk barks, fruits, and flowers of A. scholaris. The impact of seasonal changes on the production of alkaloids in the leaves of A. scholaris was also investigated. One and two-dimensional Nuclear Magnetic Resonance (NMR) experiments were utilized for the characterization of alkaloids and total eight alkaloids (picrinine, picralinal, akuammidine, 19 S scholaricine, 19,20 E vallesamine, Nb-demethylalstogustine N-Oxide, Nb-demethylalstogustine, and echitamine) were characterized and quantified. Quantitative and multivariate analysis suggested that the alkaloids content is tissue specific, illustrating the effect of plant tissue organization on alkaloidal production in A. scholaris. The results suggest that the best part to obtain alkaloids is trunk barks, since it contains 7 alkaloids. However, the best part for isolating picrinine, picralinal, akuammidine, 19 S scholaricine, and 19,20 E vallesamine is fruit, since it shows highest amount of these alkaloids. Undoubtedly, NMR and statistical methods are very helpful to differentiate the profile of alkaloids in A. scholaris. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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11 pages, 3829 KiB

Open AccessArticle

Identification and Quantification of Flavonoids in Okra (Abelmoschus esculentus L. Moench) and Antiproliferative Activity In Vitro of Four Main Components Identified

by Jing Yang, Xiaoqi Chen, Shuaiqi Rao, Yaochen Li, Yunxiang Zang and Biao Zhu

Metabolites 2022, 12(6), 483; https://doi.org/10.3390/metabo12060483 - 26 May 2022

Cited by 8 | Viewed by 2847

Abstract

Okra is a kind of flavonoid-rich food which was reported to have a variety of health functions. Flavonoids are the major polyphenolic compounds in okra and are thought to play a role in reducing the risk of disease. The aim of this study [...] Read more.

Okra is a kind of flavonoid-rich food which was reported to have a variety of health functions. Flavonoids are the major polyphenolic compounds in okra and are thought to play a role in reducing the risk of disease. The aim of this study was to isolate and identify the flavonoids composition in okra pods and explore the activity of the main flavonoids components identified on inhibiting tumor cell proliferation in vitro. Six individual flavonoids were identified by HPLC-MS/MS: quercetin-3-gentiobioside (Q3G), quercetin-3-sambubioside (Q3S), rutin, quercetin-7-glucoside (Q7G), isoquercitrin (ISO) and quercetin-3-malonylglucoside (Q3M), which were all separated well within 30 min. The analytical method was validated by the recovery of spiked samples and so on. Moreover, four main flavonoids components, namely Q3G, Q3S, ISO and Q3M, exhibited significant (p < 0.05) inhibition of NCI-N87, A375, A549 cells proliferation (25−100 μmol/L) and of HFLS-RA (200−300 μmol/L) in different levels, according to MTT method, respectively. It is demonstrated that the flavonoids components of okra exhibited a noteworthy development prospect as a possible nutraceutical dietary supplement. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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15 pages, 2471 KiB

Open AccessArticle

Protective Effect of Butanolic Fraction of Delphinium brunonianum on Fructose-Mediated Metabolic Alterations in Rats

by Syed Nasir Abbas Bukhari, Hira Asif, Alamgeer, Mulazim Hussain Asim, Hafiz Muhammad Irfan, Hasan Ejaz, Mervat A. Elsherif and Kashaf Junaid

Metabolites 2022, 12(6), 481; https://doi.org/10.3390/metabo12060481 - 26 May 2022

Cited by 3 | Viewed by 2284

Abstract

The present study was conducted with an intent to evaluate the protective effect of butanolic fraction of Delphinium brunonianum on fructose mediated metabolic abnormalities in rats. Rats in all groups except control group were fed on 10% fructose for 6 weeks; however, rats [...] Read more.

The present study was conducted with an intent to evaluate the protective effect of butanolic fraction of Delphinium brunonianum on fructose mediated metabolic abnormalities in rats. Rats in all groups except control group were fed on 10% fructose for 6 weeks; however, rats in the treated group also received butanolic fraction for the last 3 weeks, along with the fructose. Moreover, phytoconstituents present in butanolic fraction were analyzed using LC-MS. All doses of butanolic fraction profoundly reduce the fructose-induced blood pressure, sympathetic over-activity, and weight gain. Furthermore, butanolic fraction prominently reduces the glucose intolerance and hyperinsulinemia in fructose-fed rats. On treatment with butanolic fraction, oxidative enzymes and the functionality of the aorta was also restored. Phytochemical analysis revealed the presence of several active constituents including bergenin, scopolin, rutinoside, kaempferol, coumaric acid, apigenin, and gingerol. In conclusion, butanolic fraction of Delphinium brunonianum has the potential to prevent and recover the fructose-induced metabolic perturbations. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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29 pages, 1613 KiB

Open AccessArticle

Characterization of Constituents with Potential Anti-Inflammatory Activity in Chinese Lonicera Species by UHPLC-HRMS Based Metabolite Profiling

by Eva-Maria Pferschy-Wenzig, Sabine Ortmann, Atanas G. Atanasov, Klara Hellauer, Jürgen Hartler, Olaf Kunert, Markus Gold-Binder, Angela Ladurner, Elke H. Heiß, Simone Latkolik, Yi-Min Zhao, Pia Raab, Marlene Monschein, Nina Trummer, Bola Samuel, Sara Crockett, Jian-Hua Miao, Gerhard G. Thallinger, Valery Bochkov, Verena M. Dirsch and Rudolf Bauer Show full author list Hide full author list

Metabolites 2022, 12(4), 288; https://doi.org/10.3390/metabo12040288 - 25 Mar 2022

Cited by 5 | Viewed by 3185

Abstract

This study centered on detecting potentially anti-inflammatory active constituents in ethanolic extracts of Chinese Lonicera species by taking an UHPLC-HRMS-based metabolite profiling approach. Extracts from eight different Lonicera species were subjected to both UHPLC-HRMS analysis and to pharmacological testing in three different cellular [...] Read more.

This study centered on detecting potentially anti-inflammatory active constituents in ethanolic extracts of Chinese Lonicera species by taking an UHPLC-HRMS-based metabolite profiling approach. Extracts from eight different Lonicera species were subjected to both UHPLC-HRMS analysis and to pharmacological testing in three different cellular inflammation-related assays. Compounds exhibiting high correlations in orthogonal projections to latent structures discriminant analysis (OPLS-DA) of pharmacological and MS data served as potentially activity-related candidates. Of these candidates, 65 were tentatively or unambiguously annotated. 7-Hydroxy-5,3′,4′,5′-tetramethoxyflavone and three bioflavonoids, as well as three C₃₂- and one C₃₄-acetylated polyhydroxy fatty acid, were isolated from Lonicera hypoglauca leaves for the first time, and their structures were fully or partially elucidated. Of the potentially active candidate compounds, 15 were subsequently subjected to pharmacological testing. Their activities could be experimentally verified in part, emphasizing the relevance of Lonicera species as a source of anti-inflammatory active constituents. However, some compounds also impaired the cell viability. Overall, the approach was found useful to narrow down the number of potentially bioactive constituents in the complex extracts investigated. In the future, the application of more refined concepts, such as extract prefractionation combined with bio-chemometrics, may help to further enhance the reliability of candidate selection. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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13 pages, 1939 KiB

Open AccessArticle

Biological Activity and NMR-Fingerprinting of Balkan Endemic Species Stachys thracica Davidov

by Desislava I. Mantovska, Miroslava K. Zhiponova, Milen I. Georgiev, Kalina Alipieva, Ivanka Tsacheva, Svetlana Simova and Zhenya P. Yordanova

Metabolites 2022, 12(3), 251; https://doi.org/10.3390/metabo12030251 - 16 Mar 2022

Cited by 7 | Viewed by 2855

Abstract

Stachys thracica Davidov is a Balkan endemic species distributed in Bulgaria, Greece, and Turkey. In Bulgaria, it is classified as “rare” and is under the protection of the Bulgarian biodiversity law. The aim of our study was to develop an efficient protocol for [...] Read more.

Stachys thracica Davidov is a Balkan endemic species distributed in Bulgaria, Greece, and Turkey. In Bulgaria, it is classified as “rare” and is under the protection of the Bulgarian biodiversity law. The aim of our study was to develop an efficient protocol for ex situ conservation of S. thracica and to perform comparative NMR-based metabolite profiling and bioactivity assays of extracts from in situ grown, in vitro cultivated, and ex vitro acclimated plants. Micropropagation of S. thracica was achieved by in vitro cultivation of mono-nodal segments on basal MS medium. Ex vitro adaptation was accomplished in the experimental field with 83% survival while conserved genetic identity between in vitro and ex vitro plants as shown by the overall sequence-related amplified polymorphism marker patterns was established. Verbascoside, chlorogenic acid, and trigonelline appeared the main secondary metabolites in in situ, in vitro cultivated, and ex vitro acclimated S. thracica. High total phenolic and flavonoid content as well as antioxidant and radical scavenging activity were observed in in situ and ex vitro plants. Further, the anti-inflammatory activity of S. thracica was tested by hemolytic assay and a high inhibition of the complement system was observed. Initiated in vitro and ex vitro cultures offer an effective tool for the management and better exploitation of the Stachys secondary metabolism and the selection of lines with high content of bioactive molecules and nutraceuticals. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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Review

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35 pages, 1349 KiB

Open AccessReview

Bioactive Lichen Secondary Metabolites and Their Presence in Species from Chile

by Erick Poulsen-Silva, Felipe Gordillo-Fuenzalida, Cristian Atala, Adrián A. Moreno and María Carolina Otero

Metabolites 2023, 13(7), 805; https://doi.org/10.3390/metabo13070805 - 28 Jun 2023

Cited by 10 | Viewed by 2735

Abstract

Lichens are symbiotic organisms composed of at least one fungal and one algal species. They are found in different environments around the world, even in the poles and deserts. Some species can withstand extreme abiotic conditions, including radiation and the vacuum of space. [...] Read more.

Lichens are symbiotic organisms composed of at least one fungal and one algal species. They are found in different environments around the world, even in the poles and deserts. Some species can withstand extreme abiotic conditions, including radiation and the vacuum of space. Their chemistry is mainly due to the fungal metabolism and the production of several secondary metabolites with biological activity, which have been isolated due to an increasing interest from the pharmaceutical community. However, beyond the experimental data, little is known about their mechanisms of action and the potential pharmaceutical use of these kinds of molecules, especially the ones isolated from lesser-known species and/or lesser-studied countries. The main objective of this review is to analyze the bibliographical data of the biological activity of secondary metabolites from lichens, identifying the possible mechanisms of action and lichen species from Chile. We carried out a bibliographic revision of different scientific articles in order to collect all necessary information on the biological activity of the metabolites of these lichen species. For this, validated databases were used. We found the most recent reports where in vitro and in vivo studies have demonstrated the biological properties of these metabolites. The biological activity, namely anticancer, antioxidant, and anti-inflammatory activity, of 26 secondary metabolites are described, as well as their reported molecular mechanisms. The most notable metabolites found in this review were usnic acid, atranorin, protolichesterinic acid, and lobaric acid. Usnic acid was the most investigated metabolite, in addition to undergoing toxicological and pharmacological studies, where a hepatotoxicity effect was reported due to uncoupling oxidative phosphorylation. Additionally, no major studies have been made to validate the pharmacological application of these metabolites, and few advancements have been made in their artificial growth in bioreactors. Despite the described biological activities, there is little support to consider these metabolites in pharmaceutical formulations or to evaluate them in clinical trials. Nevertheless, it is important to carry out further studies regarding their possible human health effects. These lichen secondary metabolites present a promising research opportunity to find new pharmaceutical molecules due to their bioactive properties. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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12 pages, 959 KiB

Open AccessReview

Modes of Action of 1,8-Cineol in Infections and Inflammation

by Ralph Pries, Stephanie Jeschke, Anke Leichtle and Karl-Ludwig Bruchhage

Metabolites 2023, 13(6), 751; https://doi.org/10.3390/metabo13060751 - 13 Jun 2023

Cited by 9 | Viewed by 4322

Abstract

The monoterpene 1,8-Cineol is a natural plant-based therapeutic agent that is commonly applied to treat different inflammatory diseases due to its mucolytic, anti-microbial and anti-inflammatory properties. It has become increasingly clear in the recent years that 1,8-Cineol spreads almost everywhere in the human [...] Read more.

The monoterpene 1,8-Cineol is a natural plant-based therapeutic agent that is commonly applied to treat different inflammatory diseases due to its mucolytic, anti-microbial and anti-inflammatory properties. It has become increasingly clear in the recent years that 1,8-Cineol spreads almost everywhere in the human body after its oral administration, from the gut to the blood to the brain. Its anti-microbial potential and even its anti-viral effects have been observed to include numerous bacteria and fungi species. Many recent studies help to better understand the cellular and molecular immunological consequences of 1,8-Cineol treatment in inflammatory diseases and further provide information concerning the mechanistic modes of action in the regulation of distinct inflammatory biosynthetic pathways. This review aims to present a holistic and understandable overview of the different aspects of 1,8-Cineol in infections and inflammation. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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19 pages, 998 KiB

Open AccessReview

The Role of Quorum Sensing Molecules in Bacterial–Plant Interactions

by Jan Majdura, Urszula Jankiewicz, Agnieszka Gałązka and Sławomir Orzechowski

Metabolites 2023, 13(1), 114; https://doi.org/10.3390/metabo13010114 - 10 Jan 2023

Cited by 18 | Viewed by 4623

Abstract

Quorum sensing (QS) is a system of communication of bacterial cells by means of chemical signals called autoinducers, which modulate the behavior of entire populations of Gram-negative and Gram-positive bacteria. Three classes of signaling molecules have been recognized, Al-1, Al-2, Al-3, whose functions [...] Read more.

Quorum sensing (QS) is a system of communication of bacterial cells by means of chemical signals called autoinducers, which modulate the behavior of entire populations of Gram-negative and Gram-positive bacteria. Three classes of signaling molecules have been recognized, Al-1, Al-2, Al-3, whose functions are slightly different. However, the phenomenon of quorum sensing is not only concerned with the interactions between bacteria, but the whole spectrum of interspecies interactions. A growing number of research results confirm the important role of QS molecules in the growth stimulation and defense responses in plants. Although many of the details concerning the signaling metabolites of the rhizosphere microflora and plant host are still unknown, Al-1 compounds should be considered as important components of bacterial–plant interactions, leading to the stimulation of plant growth and the biological control of phytopathogens. The use of class 1 autoinducers in plants to induce beneficial activity may be a practical solution to improve plant productivity under field conditions. In addition, researchers are also interested in tools that offer the possibility of regulating the activity of autoinducers by means of degrading enzymes or specific inhibitors (QSI). Current knowledge of QS and QSI provides an excellent foundation for the application of research to biopreparations in agriculture, containing a consortia of AHL-producing bacteria and QS inhibitors and limiting the growth of phytopathogenic organisms. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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16 pages, 1680 KiB

Open AccessReview

Melatonin from Microorganisms, Algae, and Plants as Possible Alternatives to Synthetic Melatonin

by Marino B. Arnao, Manuela Giraldo-Acosta, Ana Castejón-Castillejo, Marta Losada-Lorán, Pablo Sánchez-Herrerías, Amina El Mihyaoui, Antonio Cano and Josefa Hernández-Ruiz

Metabolites 2023, 13(1), 72; https://doi.org/10.3390/metabo13010072 - 2 Jan 2023

Cited by 16 | Viewed by 5622

Abstract

Melatonin dietary supplements are widely consumed worldwide, with developed countries as the largest consumers, with an estimated annual growth rate of approximately 10% until 2027, mainly in developing countries. The wide use of melatonin against sleep disorders and particular problems, such as jet [...] Read more.

Melatonin dietary supplements are widely consumed worldwide, with developed countries as the largest consumers, with an estimated annual growth rate of approximately 10% until 2027, mainly in developing countries. The wide use of melatonin against sleep disorders and particular problems, such as jet lag, has been added to other applications, such as anti-aging, anti-stress, immune system activation, anticancer, and others, which have triggered its use, normally without a prescription. The chemical industry currently covers 100% of the needs of the melatonin market. Motivated by sectors with more natural consumption habits, a few years ago, the possibility of obtaining melatonin from plants, called phytomelatonin, arose. More recently, the pharmaceutical industry has developed genetically modified microorganisms whose ability to produce biological melatonin in bioreactors has been enhanced. This paper reviews the aspects of the chemical and biological synthesis of melatonin for human consumption, mainly as dietary supplements. The pros and cons of obtaining melatonin from microorganisms and phytomelatonin from plants and algae are analyzed, as well as the advantages of natural melatonin, avoiding unwanted chemical by-products from the chemical synthesis of melatonin. Finally, the economic and quality aspects of these new products, some of which are already marketed, are analyzed. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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28 pages, 2047 KiB

Open AccessReview

Interactions between Natural Products—A Review

by Nemanja Rajčević, Danka Bukvički, Tanja Dodoš and Petar D. Marin

Metabolites 2022, 12(12), 1256; https://doi.org/10.3390/metabo12121256 - 14 Dec 2022

Cited by 13 | Viewed by 3215

Abstract

Plant-based natural products have been used as a source for therapeutics since the dawn of civilization. According to the World Health Organization (WHO), more than 80% of the world’s population relies on traditional medicine for their primary healthcare. Numerous natural extracts, widely known [...] Read more.

Plant-based natural products have been used as a source for therapeutics since the dawn of civilization. According to the World Health Organization (WHO), more than 80% of the world’s population relies on traditional medicine for their primary healthcare. Numerous natural extracts, widely known in Traditional Chinese Medicine, Indian Ayurveda medicine and other practices, have led to the modern discovery and development of new drugs. Plants continuously interact with their environment, producing new compounds and ever-changing combinations of existing ones. Interestingly, some of the compounds have shown lower therapeutic activity in comparison to the extract they were isolated from. These findings suggest that the higher therapeutic activity of the source extract was due to the synergistic effect of several compounds. In other words, the total therapeutic potential of the extract cannot be explained only by the sum of its parts alone. In traditional medicine, most herbal remedies are based on a mixture of plants, and it is the interaction between different constituents that amplifies their therapeutic potential. Considering the significant influence traditional medicine has on human healthcare, knowing and studying the synergistic effect of compounds is paramount in designing smart therapeutic agents. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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13 pages, 1739 KiB

Open AccessReview

The Radioprotective Activity of Resveratrol—Metabolomic Point of View

by Michalina Gramatyka

Metabolites 2022, 12(6), 478; https://doi.org/10.3390/metabo12060478 - 25 May 2022

Cited by 3 | Viewed by 2245

Abstract

Resveratrol, a plant-derived polyphenol, is an intensively studied compound with widely documented positive effects on health. Antioxidant activity is the property most often mentioned as responsible for its beneficial effects. Therefore, since the adverse effect of ionizing radiation is primarily related to the [...] Read more.

Resveratrol, a plant-derived polyphenol, is an intensively studied compound with widely documented positive effects on health. Antioxidant activity is the property most often mentioned as responsible for its beneficial effects. Therefore, since the adverse effect of ionizing radiation is primarily related to the induction of oxidative stress, the question arises of whether the use of resveratrol could have a radioprotective effect. This paper summarizes the data on the cytoprotective activity of resveratrol and pieces of evidence for the potential interplay between response to radiation and resveratrol activity. The paper focuses on changes in the metabolic profile of cells and organisms induced by ionizing radiation and exposure to resveratrol. The comparison of metabolic changes induced by both factors provides a rationale for the potential mechanism of the radioprotective effects of resveratrol. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Natural Sources)

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