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18 pages, 1660 KiB

Open AccessArticle

GC-MS and LC-DAD-MS Phytochemical Profiling for Characterization of Three Native Salvia Taxa from Eastern Mediterranean with Antiglycation Properties

by Maria D. Gkioni, Konstantina Zeliou, Virginia D. Dimaki, Panayiotis Trigas and Fotini N. Lamari

Molecules 2023, 28(1), 93; https://doi.org/10.3390/molecules28010093 - 22 Dec 2022

Cited by 6 | Viewed by 2302

Abstract

Salvia fruticosa and S. pomifera subsp. calycina are native to Eastern Mediterranean and S. pomifera subsp. pomifera is endemic to Greece. The primary aim of this study was to develop an analytical methodology for metabolomic profiling and to study their efficacy in combating [...] Read more.

Salvia fruticosa and S. pomifera subsp. calycina are native to Eastern Mediterranean and S. pomifera subsp. pomifera is endemic to Greece. The primary aim of this study was to develop an analytical methodology for metabolomic profiling and to study their efficacy in combating glycation, the major biochemical complication of diabetes. After sequential ultrasound-assisted extraction of 2 g of leaves with petroleum ether and 70% methanol, the volatile metabolites in the petroleum ether extracts were studied with GC-MS (Gas Chromatography-Mass Spectrometry), whereas the polar metabolites in the hydroalcoholic extracts were determined and quantified by UHPLC-DAD–ESI-MS (Ultra-High Performance Liquid Chromatography–Diode Array Detector–Mass Spectrometry). This methodology was applied to five populations belonging to the three native taxa. 1,8-Cineole was the predominant volatile (34.8–39.0%) in S. fruticosa, while S. pomifera had a greater content of α-thujone (19.7–41.0%) and β-thujone (6.0–39.1%). Principal Component Analysis (PCA) analysis of the volatiles could discriminate the different taxa. UHPLC-DAD-ESI-MS demonstrated the presence of 50 compounds, twenty of which were quantified. PCA revealed that not only the taxa but also the populations of S. pomifera subsp. pomifera could be differentiated. All Salvia samples inhibited advanced glycation end-product formation in a bovine serum albumin/2-deoxyribose assay; rosmarinic and carnosic acid shared this activity. This study demonstrates the antiglycation activity of S. fruticosa and S. pomifera extracts for the first time and presents a miniaturized methodology for their metabolomic profiling, which could aid chemotaxonomic studies and serve as a tool for their authentication and quality control. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Medicinal and Food Plants)

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20 pages, 2149 KiB

Open AccessArticle

Metabolite Profiling and Bioassay-Guided Fractionation of Zataria multiflora Boiss. Hydroethanolic Leaf Extracts for Identification of Broad-Spectrum Pre and Postharvest Antifungal Agents

by Ali Karimi, Torsten Meiners and Christoph Böttcher

Molecules 2022, 27(24), 8903; https://doi.org/10.3390/molecules27248903 - 14 Dec 2022

Viewed by 1853

Abstract

Hydroethanolic leaf extracts of 14 Iranian Zataria multiflora Boiss. populations were screened for their antifungal activity against five plant pathogenic fungi and metabolically profiled using a non-targeted workflow based on UHPLC/ESI-QTOFMS. Detailed tandem mass-spectrometric analyses of one of the most active hydroethanolic leaf [...] Read more.

Hydroethanolic leaf extracts of 14 Iranian Zataria multiflora Boiss. populations were screened for their antifungal activity against five plant pathogenic fungi and metabolically profiled using a non-targeted workflow based on UHPLC/ESI-QTOFMS. Detailed tandem mass-spectrometric analyses of one of the most active hydroethanolic leaf extracts led to the annotation of 68 non-volatile semi-polar secondary metabolites, including 33 flavonoids, 9 hydroxycinnamic acid derivatives, 14 terpenoids, and 12 other metabolites. Rank correlation analyses using the abundances of the annotated metabolites in crude leaf extracts and their antifungal activity revealed four O-methylated flavones, two flavanones, two dihydroflavonols, five thymohydroquinone glycoconjugates, and five putative phenolic diterpenoids as putative antifungal metabolites. After bioassay-guided fractionation, a number of mono-, di- and tri-O-methylated flavones, as well as three of unidentified phenolic diterpenoids, were found in the most active subfractions. These metabolites are promising candidates for the development of new natural fungicides for the protection of agro-food crops. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Medicinal and Food Plants)

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10 pages, 1079 KiB

Open AccessArticle

Preventive Effect of Nuciferine on H₂O₂-Induced Fibroblast Senescence and Pro-Inflammatory Cytokine Gene Expression

by Suphachai Charoensin and Wajaree Weera

Molecules 2022, 27(23), 8148; https://doi.org/10.3390/molecules27238148 - 23 Nov 2022

Cited by 7 | Viewed by 2378

Abstract

Human dermal fibroblasts play an important role in skin homeostasis by producing and degrading extracellular matrix components. They have more replicative senescence when exposed to environmental and oxidative insults, resulting in human skin aging. However, this phenomenon can be mitigated by antioxidant phytochemicals. [...] Read more.

Human dermal fibroblasts play an important role in skin homeostasis by producing and degrading extracellular matrix components. They have more replicative senescence when exposed to environmental and oxidative insults, resulting in human skin aging. However, this phenomenon can be mitigated by antioxidant phytochemicals. The aim of the present study was to investigate the potential of nuciferine (an alkaloid from Nelumbo nucifera leaf) in preventing stress-induced fibroblast senescence by using a hydrogen-peroxide (H₂O₂)-induced senescence model. We found that H₂O₂ treatment resulted in a significant increase in senescence-associated β-galactosidase (SA-β-gal)-positive cells. Nuciferine-treated cells, however, showed a reduction in senescent phenotype. Furthermore, we observed the key molecular markers including the senescence-associated secretory phenotype (SASP) and cell cycle regulators. The mRNA levels of CXCL1, CXCL2, IL-6, and IL-8 (pro-inflammatory cytokines) reduced significantly in nuciferine-treated cells. The extracellular IL-6 and IL-8 levels were also decreased in treated cells, whereas the key cell cycle regulators (p16 and p21) were markedly affected by nuciferine at the highest concentration. The results of the present study clearly show that the preventive activity of nuciferine against H₂O₂-induced senescence in dermal fibroblasts is fundamental and promising for further applications in anti-aging product research and development. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Medicinal and Food Plants)

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20 pages, 3176 KiB

Open AccessArticle

Autoxidation Products of the Methanolic Extract of the Leaves of Combretum micranthum Exert Antiviral Activity against Tomato Brown Rugose Fruit Virus (ToBRFV)

by Valeria Iobbi, Anna Paola Lanteri, Andrea Minuto, Valentina Santoro, Giuseppe Ferrea, Paola Fossa and Angela Bisio

Molecules 2022, 27(3), 760; https://doi.org/10.3390/molecules27030760 - 24 Jan 2022

Cited by 9 | Viewed by 4048

Abstract

Tomato brown rugose fruit virus (ToBRFV) is a new damaging plant virus of great interest from both an economical and research point of view. ToBRFV is transmitted by contact, remains infective for months, and to-date, no resistant cultivars have been developed. Due to [...] Read more.

Tomato brown rugose fruit virus (ToBRFV) is a new damaging plant virus of great interest from both an economical and research point of view. ToBRFV is transmitted by contact, remains infective for months, and to-date, no resistant cultivars have been developed. Due to the relevance of this virus, new effective, sustainable, and operator-safe antiviral agents are needed. Thus, 4-hydroxybenzoic acid was identified as the main product of the alkaline autoxidation at high temperature of the methanolic extract of the leaves of C. micranthum, known for antiviral activity. The autoxidized extract and 4-hydroxybenzoic acid were assayed in in vitro experiments, in combination with a mechanical inoculation test of tomato plants. Catechinic acid, a common product of rearrangement of catechins in hot alkaline solution, was also tested. Degradation of the viral particles, evidenced by the absence of detectable ToBRFV RNA and the loss of virus infectivity, as a possible consequence of disassembly of the virus coat protein (CP), were shown. Homology modeling was then applied to prepare the protein model of ToBRFV CP, and its structure was optimized. Molecular docking simulation showed the interactions of the two compounds, with the amino acid residues responsible for CP-CP interactions. Catechinic acid showed the best binding energy value in comparison with ribavirin, an anti-tobamovirus agent. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Medicinal and Food Plants)

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24 pages, 7009 KiB

Open AccessArticle

Co-Inhibition of P-gp and Hsp90 by an Isatin-Derived Compound Contributes to the Increase of the Chemosensitivity of MCF7/ADR-Resistant Cells to Doxorubicin

by Ashraf N. Abdalla, Miriana Di Stefano, Giulio Poli, Tiziano Tuccinardi, Ammar Bader, Antonio Vassallo, Mohamed E. Abdallah, Mahmoud Zaki El-Readi, Bassem Refaat, Alanood S. Algarni, Rizwan Ahmad, Hamad M. Alkahtani, Alaa A.-M. Abdel-Aziz, Adel S. El-Azab and Aljawharah Alqathama

Molecules 2022, 27(1), 90; https://doi.org/10.3390/molecules27010090 - 24 Dec 2021

Cited by 9 | Viewed by 4505

Abstract

Breast cancer is a complex and multi-drug resistant (MDR) disease, which could result in the failure of many chemotherapeutic clinical agents. Discovering effective molecules from natural products or by derivatization from known compounds is the interest of many research studies. The first objective [...] Read more.

Breast cancer is a complex and multi-drug resistant (MDR) disease, which could result in the failure of many chemotherapeutic clinical agents. Discovering effective molecules from natural products or by derivatization from known compounds is the interest of many research studies. The first objective of the present study is to investigate the cytotoxic combinatorial, chemosensitizing, and apoptotic effects of an isatin derived compound (5,5-diphenylimidazolidine-2,4-dione conjugated with 5-substituted isatin, named HAA₂₀₂₁ in the present study) against breast cancer cells (MCF7) and breast cancer cells resistant to doxorubicin (MCF7/ADR) when combined with doxorubicin. The second objective is to investigate the binding mode of HAA₂₀₂₁ withP-glycoprotein (P-gp) and heat shock protein 90 (Hsp90), and to determine whether their co-inhibition by HAA₂₀₂₁ contribute to the increase of the chemosensitization of MCF7/ADR cells to doxorubicin. The combination of HAA₂₀₂₁, at non-toxic doses, with doxorubicin synergistically inhibited the proliferation while inducing significant apoptosis in MCF7 cells. Moreover, HAA₂₀₂₁ increased the chemosensitization of MCF7/ADR cells to doxorubicin, resulting in increased cytotoxicity/selectivity and apoptosis-inducing efficiency compared with the effect of doxorubicin or HAA₂₀₂₁ alone against MCF7/ADR cells. Molecular modeling showed that two molecules of HAA₂₀₂₁ bind to P-gp at the same time, causing P-gp inhibitory effect of the MDR efflux pump, and accumulation of Rhodamine-123 (Rho123) in MCF7/ADR cells. Furthermore, HAA₂₀₂₁ stably interacted with Hsp90α more efficiently compared with 17-N-allylamino-17-demethoxygeldanamycin (17-AAG), which was confirmed with the surface plasmon resonance (SPR) and molecular modeling studies. Additionally, HAA₂₀₂₁ showed multi-target effects via the inhibition of Hsp90 and nuclear factor kappa B (NF-𝜅B) proteins in MCF7 and MCF7/ADR cells. Results of real time-PCR also confirmed the synergistic co-inhibition of P-gp/Hsp90α genes in MCF7/ADR cells. Further pharmacokinetic and in vivo studies are warranted for HAA₂₀₂₁ to confirm its anticancer capabilities. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Medicinal and Food Plants)

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15 pages, 1991 KiB

Open AccessArticle

Phytochemistry, Food Application, and Therapeutic Potential of the Medicinal Plant (Withania coagulans): A Review

by Muhammad Issa Khan, Maria Maqsood, Raakia Anam Saeed, Amna Alam, Amna Sahar, Marek Kieliszek, Antoni Miecznikowski, Hafiz Shehzad Muzammil and Rana Muhammad Aadil

Molecules 2021, 26(22), 6881; https://doi.org/10.3390/molecules26226881 - 15 Nov 2021

Cited by 38 | Viewed by 8522

Abstract

Herbal plants have been utilized to treat and cure various health-related problems since ancient times. The use of Ayurvedic medicine is very significant because of its least reported side effects and host of advantages. Withania coagulans (Family; Solanaceae), a valuable medicinal plant, has [...] Read more.

Herbal plants have been utilized to treat and cure various health-related problems since ancient times. The use of Ayurvedic medicine is very significant because of its least reported side effects and host of advantages. Withania coagulans (Family; Solanaceae), a valuable medicinal plant, has been used to cure abnormal cell growth, wasting disorders, neural as well as physical problems, diabetes mellitus, insomnia, acute and chronic hepatic ailments. This review provides critical insight regarding the phytochemistry, biological activities, and pharmacognostic properties of W. coagulans. It has been known to possess diuretic, anti-inflammatory, anti-bacterial, anti-fungal, cardio-protective, hepato-protective, hypoglycemic, anti-oxidative, and anti-mutagenic properties owing to the existence of withanolides, an active compound present in it. Apart from withanolides, W. coagulans also contains many phytochemicals such as flavonoids, tannins, and β-sterols. Several studies indicate that various parts of W. coagulans and their active constituents have numerous pharmacological and therapeutic properties and thus can be considered as a new drug therapy against multiple diseases. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Medicinal and Food Plants)

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17 pages, 7630 KiB

Open AccessArticle

Abietane Diterpenoids from the Hairy Roots of Salvia corrugata

by Roméo Arago Dougué Kentsop, Valeria Iobbi, Giuliana Donadio, Barbara Ruffoni, Nunziatina De Tommasi and Angela Bisio

Molecules 2021, 26(17), 5144; https://doi.org/10.3390/molecules26175144 - 25 Aug 2021

Cited by 6 | Viewed by 3361

Abstract

Salvia corrugata Vahl. is an interesting source of abietane and abeo-abietane compounds that showed antibacterial, antitumor, and cytotoxic activities. The aim of the study was to obtain transformed roots of S. corrugata and to evaluate the production of terpenoids in comparison with [...] Read more.

Salvia corrugata Vahl. is an interesting source of abietane and abeo-abietane compounds that showed antibacterial, antitumor, and cytotoxic activities. The aim of the study was to obtain transformed roots of S. corrugata and to evaluate the production of terpenoids in comparison with in vivo root production. Hairy roots were initiated from leaf explants by infection with ATCC 15834 Agrobacterium rhizogenes onto hormone-free Murashige and Skoog (MS) solid medium. Transformation was confirmed by polymerase chain reaction analysis of rolC and virC1 genes. The biomass production was obtained in hormone-free liquid MS medium using Temporary Immersion System bioreactor RITA^®. The chromatographic separation of the methanolic extract of the untransformed roots afforded horminone, ferruginol, 7-O-acetylhorminone and 7-O-methylhorminone. Agastol and ferruginol were isolated and quantified from the hairy roots. The amount of these metabolites indicated that the hairy roots of S. corrugata can be considered a source of these compounds. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Medicinal and Food Plants)

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17 pages, 3799 KiB

Open AccessArticle

The Modulation of PCSK9 and LDLR by Supercritical CO₂ Extracts of Mentha longifolia and Isolated Piperitone Oxide, an In Vitro Study

by Stefania Sut, Irene Ferrarese, Maria Giovanna Lupo, Nicola De Zordi, Elisa Tripicchio, Nicola Ferri and Stefano Dall’ Acqua

Molecules 2021, 26(13), 3886; https://doi.org/10.3390/molecules26133886 - 25 Jun 2021

Cited by 3 | Viewed by 2567

Abstract

In the present study the ability of supercritical carbon dioxide (SCO₂) extracts of M. longifolia L. leaves to modulate low-density lipoprotein receptor (LDLR) and proprotein convertase subtilisin/kexin type 9 (PCSK9) expression was evaluated in cultured human hepatoma cell lines Huh7 and [...] Read more.

In the present study the ability of supercritical carbon dioxide (SCO₂) extracts of M. longifolia L. leaves to modulate low-density lipoprotein receptor (LDLR) and proprotein convertase subtilisin/kexin type 9 (PCSK9) expression was evaluated in cultured human hepatoma cell lines Huh7 and HepG2. Two SCO₂ extracts, one oil (ML-SCO₂) and a semisolid (MW-SCO₂), were subjected to detailed chemical characterization by mono- and bidimensional nuclear magnetic resonance (1D, 2D-NMR), gas chromatography coupled with mass spectrometry (GC-MS) and liquid chromatography coupled with mass spectrometry (LC-MS). Chemical analysis revealed significant amounts of fatty acids, phytosterols and terpenoids. ML-SCO₂ was able to induce LDLR expression at a dose of 60 µg/mL in HuH7 and HepG2 cell lines. Furthermore, ML-SCO₂ reduced PCSK9 secretion in a concentration-dependent manner in both cell lines. Piperitone oxide, the most abundant compound of the volatile constituent of ML-SCO₂ (27% w/w), was isolated and tested for the same targets, showing a very effective reduction of PCSK9 expression. The overall results revealed the opportunity to obtain a new nutraceutical ingredient with a high amount of phytosterols and terpenoids using the SCO₂ extraction of M. longifolia L., a very well-known botanical species used as food. Furthermore, for the first time we report the high activity of piperitone oxide in the reduction of PCSK9 expression. Full article

(This article belongs to the Special Issue Bioactive Metabolites from Medicinal and Food Plants)

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