Research

18 pages, 2617 KiB

Open AccessArticle

Phenolic Compounds and Organic Acid Composition of Syringa vulgaris L. Flowers and Infusions

by Monika Gąsecka, Agnieszka Krzymińska-Bródka, Zuzanna Magdziak, Piotr Czuchaj and Joanna Bykowska

Molecules 2023, 28(13), 5159; https://doi.org/10.3390/molecules28135159 - 01 Jul 2023

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The study aimed to determine the content of phenolic compounds (phenolic acids and flavonoids) and organic acids in dried flowers and water infusions of non-oxidised and oxidised flowers from four lilac cultivars. The diversity in the total phenolic and flavonoid content was in [...] Read more.

The study aimed to determine the content of phenolic compounds (phenolic acids and flavonoids) and organic acids in dried flowers and water infusions of non-oxidised and oxidised flowers from four lilac cultivars. The diversity in the total phenolic and flavonoid content was in the flowers (18.35–67.14 and 2.03–2.65 mg g⁻¹ DW, respectively) and infusions (14.72–47.78 and 0.20–1.84 mg per 100 mL infusion, respectively) depending the flower colour and form (oxidised and non-oxidised). Phenolic compounds and organic acids were susceptible to oxidation. Compared to infusions, flowers had more phenolic compounds and organic acids. The highest content of most phenolic compounds was confirmed for non-oxidised purple flowers (up to 7825.9 µg g⁻¹ DW for chlorogenic acid) while in infusions for non-oxidised white flowers (up to 667.1 µg per 100 mL infusions for vanillic acid). The phenolic profile of the infusions was less diverse than that of flowers. The scavenging ability ranged from 52 to 87%. The highest organic acid content in flowers was for oxidised blue and purple flowers (2528.1 and 2479.0 µg g⁻¹ DW, respectively) while in infusions the highest organic acid content was for oxidised purple flowers (550.1 µg per 100 mL infusions). Full article

(This article belongs to the Special Issue Phenolic/Polyphenolic Profile and Biological Activities of Natural Products)

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25 pages, 10078 KiB

Open AccessArticle

Rindera graeca (A. DC.) Boiss. & Heldr. (Boraginaceae) In Vitro Cultures Targeting Lithospermic Acid B and Rosmarinic Acid Production

by Katarzyna Sykłowska-Baranek, Małgorzata Gaweł, Łukasz Kuźma, Beata Wileńska, Mateusz Kawka, Małgorzata Jeziorek, Konstantia Graikou, Ioanna Chinou, Ewa Szyszko, Piotr Stępień, Patryk Zakrzewski and Agnieszka Pietrosiuk

Molecules 2023, 28(12), 4880; https://doi.org/10.3390/molecules28124880 - 20 Jun 2023

Cited by 1 | Viewed by 1091

Abstract

The in vitro cultures of Rindera graeca, a rare endemic plant, were developed as a sustainable source of phenolic acids. Various shoot and root cultures were established and scaled up in a sprinkle bioreactor. A multiplication rate of 7.2 shoots per explant [...] Read more.

The in vitro cultures of Rindera graeca, a rare endemic plant, were developed as a sustainable source of phenolic acids. Various shoot and root cultures were established and scaled up in a sprinkle bioreactor. A multiplication rate of 7.2 shoots per explant was achieved. HPLC–PDA–ESI–HRMS analysis revealed the presence of rosmarinic acid (RA) and lithospermic acid B (LAB) as the main secondary metabolites in both the shoot and root cultures. The maximum RA (30.0 ± 3.2 mg/g DW) and LAB (49.3 ± 15.5 mg/g DW) yields were determined in root-regenerated shoots. The strongest free radical scavenging activity (87.4 ± 1.1%), according to 2,2-diphenyl-1-picrylhydrazyl-hydrate assay, was noted for roots cultivated in a DCR medium. The highest reducing power (2.3 µM ± 0.4 TE/g DW), determined by the ferric-reducing antioxidant power assay, was noted for shoots cultivated on an SH medium containing 0.5 mg/L 6-benzylaminopurine. A genetic analysis performed using random amplified polymorphic DNA and start codon targeted markers revealed genetic variation of 62.8% to 96.5% among the investigated shoots and roots. This variability reflects the capacity of cultivated shoots and roots to produce phenolic compounds. Full article

(This article belongs to the Special Issue Phenolic/Polyphenolic Profile and Biological Activities of Natural Products)

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14 pages, 1871 KiB

Open AccessArticle

Effect of Light Conditions on Polyphenol Production in Transformed Shoot Culture of Salvia bulleyana Diels

by Marta Krzemińska, Katarzyna Hnatuszko-Konka, Izabela Weremczuk-Jeżyna, Aleksandra Owczarek-Januszkiewicz, Wiktoria Ejsmont, Monika A. Olszewska and Izabela Grzegorczyk-Karolak

Molecules 2023, 28(12), 4603; https://doi.org/10.3390/molecules28124603 - 07 Jun 2023

Cited by 2 | Viewed by 992

Abstract

Various strategies have been used to increase the efficiency of secondary metabolite production in Salvia plants. This report is the first to examine the spontaneous development of Salvia bulleyana shoots transformed by Agrobacterium rhizogenes on hairy roots and the influence of light conditions [...] Read more.

Various strategies have been used to increase the efficiency of secondary metabolite production in Salvia plants. This report is the first to examine the spontaneous development of Salvia bulleyana shoots transformed by Agrobacterium rhizogenes on hairy roots and the influence of light conditions on the phytochemical profile of this shoot culture. The transformed shoots were cultivated on solid MS medium with 0.1 mg/L of IAA (indole-3-acetic acid) and 1 mg/L of m-Top (meta-topolin), and their transgenic characteristic was confirmed by PCR-based detection of the rolB and rolC genes in the target plant genome. This study assessed the phytochemical, morphological, and physiological responses of the shoot culture under stimulation by light-emitting diodes (LEDs) with different wavelengths (white, WL; blue, B; red, RL; and red/blue, ML) and under fluorescent lamps (FL, control). Eleven polyphenols identified as phenolic acids and their derivatives were detected via ultrahigh-performance liquid chromatography with diode-array detection coupled to electrospray ionization tandem mass spectrometry (UPLC-DAD/ESI-MS) in the plant material, and their content was determined using high-performance liquid chromatography (HPLC). Rosmarinic acid was the predominant compound in the analyzed extracts. The mixed red and blue LEDs gave the highest levels of polyphenol and rosmarinic acid accumulation (respectively, 24.3 mg/g of DW and 20.0 mg/g of DW), reaching two times greater concentrations of polyphenols and three times greater rosmarinic acid levels compared to the aerial parts of two-year-old intact plants. Similar to WL, ML also stimulated regeneration ability and biomass accumulation effectively. However, the highest total photosynthetic pigment production (1.13 mg/g of DW for total chlorophyll and 0.231 mg/g of DW for carotenoids) was found in the shoots cultivated under RL followed by BL, while the culture exposed to BL was characterized as having the highest antioxidant enzyme activities. Full article

(This article belongs to the Special Issue Phenolic/Polyphenolic Profile and Biological Activities of Natural Products)

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17 pages, 2039 KiB

Open AccessArticle

Phenolic Acids and Amaryllidaceae Alkaloids Profiles in Leucojum aestivum L. In Vitro Plants Grown under Different Light Conditions

by Emilia Morańska, Magdalena Simlat, Marzena Warchoł, Edyta Skrzypek, Piotr Waligórski, Dominique Laurain-Mattar, Rosella Spina and Agata Ptak

Molecules 2023, 28(4), 1525; https://doi.org/10.3390/molecules28041525 - 04 Feb 2023

Cited by 5 | Viewed by 1583

Abstract

Light-emitting diodes (LEDs) have emerged as efficient light sources for promoting in vitro plant growth and primary and secondary metabolite biosynthesis. This study investigated the effects of blue, red, and white-red LED lights on plant biomass growth, photosynthetic pigments, soluble sugars, phenolic compounds, [...] Read more.

Light-emitting diodes (LEDs) have emerged as efficient light sources for promoting in vitro plant growth and primary and secondary metabolite biosynthesis. This study investigated the effects of blue, red, and white-red LED lights on plant biomass growth, photosynthetic pigments, soluble sugars, phenolic compounds, the production of Amaryllidaceae alkaloids, and the activities of antioxidant enzymes in Leucojum aestivum L. cultures. A white fluorescent light was used as a control. The plants that were grown under white-red and red light showed the highest fresh biomass increments. The blue light stimulated chlorophyll a, carotenoid, and flavonoid production. The white-red and blue lights were favourable for phenolic acid biosynthesis. Chlorogenic, p-hydroxybenzoic, caffeic, syringic, p-coumaric, ferulic, sinapic, and benzoic acids were identified in plant materials, with ferulic acid dominating. The blue light had a significant beneficial effect both on galanthamine (4.67 µg/g of dry weight (DW)) and lycorine (115 µg/g DW) biosynthesis. Red light treatment increased catalase and superoxide dismutase activities, and high catalase activity was also observed in plants treated with white-red and blue light. This is the first report to provide evidence of the effects of LED light on the biosynthesis of phenolic acid and Amaryllidaceae alkaloids in L. aestivum cultures, which is of pharmacological importance and can propose new strategies for their production. Full article

(This article belongs to the Special Issue Phenolic/Polyphenolic Profile and Biological Activities of Natural Products)

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17 pages, 2872 KiB

Open AccessArticle

Chemical, Antioxidant and Biological Studies of Brassica incana subsp. raimondoi (Brassicaceae) Leaf Extract

by Giuseppe Antonio Malfa, Francesco Pappalardo, Natalizia Miceli, Maria Fernanda Taviano, Simone Ronsisvalle, Barbara Tomasello, Simone Bianchi, Federica Davì, Vivienne Spadaro and Rosaria Acquaviva

Molecules 2023, 28(3), 1254; https://doi.org/10.3390/molecules28031254 - 27 Jan 2023

Cited by 1 | Viewed by 1761

Abstract

Brassica incana subsp. raimondoi is an endemic taxon present in a restricted area located on steep limestone cliffs at an altitude of about 500 m a.s.l. in eastern Sicily. In this research, for the first time, studies on the phytochemical profile, the antioxidant [...] Read more.

Brassica incana subsp. raimondoi is an endemic taxon present in a restricted area located on steep limestone cliffs at an altitude of about 500 m a.s.l. in eastern Sicily. In this research, for the first time, studies on the phytochemical profile, the antioxidant properties in cell-free and cell-based systems, the cytotoxicity on normal and cancer cells by 3-(4,5-Dimethylthiazol-2-yl)-2,5-Diphenyltetrazolium Bromide (MTT) assay, and on Artemia salina Leach, were performed. The total phenolic, flavonoid, and condensed tannin contents of the leaf hydroalcoholic extract were spectrophotometrically determined. Ultra-performance liquid chromatography—tandem mass spectrometer (UPLC-MS/MS) analysis highlighted the presence of several phenolic acids, flavonoids, and carotenoids, while High-Performance Liquid Chromatography with Diode-Array Detection (HPLC-DAD) identified various kaempferol and isorhamnetin derivatives. The extract exhibited different antioxidant properties according to the five in vitro methods used. Cytotoxicity by MTT assay evidenced no impact on normal human fibroblasts (HFF-1) and prostate cancer cells (DU145), and cytotoxicity accompanied by necrotic cell death for colon cancer cells (CaCo-2) and hepatoma cells (HepG2), starting from 100 μg/mL and 500 μg/mL, respectively. No cytotoxic effects were detected by the A. salina lethality bioassay. In the H₂O₂-induced oxidative stress cell model, the extract counteracted cellular reactive oxygen species (ROS) production and preserved non-protein thiol groups (RSH) affected by H₂O₂ exposure in HepG2 cells. Results suggest the potential of B. incana subsp. raimondoi as a source of bioactive molecules. Full article

(This article belongs to the Special Issue Phenolic/Polyphenolic Profile and Biological Activities of Natural Products)

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17 pages, 848 KiB

Open AccessFeature PaperArticle

Antihyaluronidase and Antioxidant Potential of Atriplex sagittata Borkh. in Relation to Phenolic Compounds and Triterpene Saponins

by Karolina Grabowska, Wioleta Pietrzak, Paweł Paśko, Agnieszka Sołtys, Agnieszka Galanty, Paweł Żmudzki, Renata Nowak and Irma Podolak

Molecules 2023, 28(3), 982; https://doi.org/10.3390/molecules28030982 - 18 Jan 2023

Cited by 2 | Viewed by 1668

Abstract

The genus Atriplex provides species that are used as food and natural remedies. In this work, the levels of soluble phenolic acids (free and conjugated) and flavonoids in extracts from roots, stems, leaves and flowers of the unexplored Atriplex sagittata Borkh were investigated [...] Read more.

The genus Atriplex provides species that are used as food and natural remedies. In this work, the levels of soluble phenolic acids (free and conjugated) and flavonoids in extracts from roots, stems, leaves and flowers of the unexplored Atriplex sagittata Borkh were investigated by LC-ESI-MS/MS, together with their antioxidant and antihyaluronidase activity. Phenolic acids were present in all parts of A. sagittata; and were most abundant in the leaves (225.24 μg/g dw.), whereas the highest content of flavonoids were found in the flowers (242.71 μg/g dw.). The most common phenolics were 4-hydroxybenzoic and salicylic acids, kaempferol-3-glucoside-7-rhamnoside, kaempferol-3-rutinoside and the rare narcissoside, which was present in almost all morphotic parts. The stem extract had the highest antioxidant activity and total phenolic content (611.86 mg/100 g dw.), whereas flower extract exerted the most potent antihyaluronidase effect (IC₅₀ = 84.67 µg/mL; control—quercetin: IC₅₀ = 514.28 μg/mL). Phytochemical analysis of the flower extract led to the isolation of two triterpene saponins that were shown to be strong hyaluronidase inhibitors (IC₅₀ = 33.77 and 168.15 µg/mL; control—escin: IC₅₀ = 307.38 µg/mL). This is the first report on the presence of phenolics and saponins in A. sagittata. The results suggest that both groups of metabolites may contribute to the overall activity of this plant species. Full article

(This article belongs to the Special Issue Phenolic/Polyphenolic Profile and Biological Activities of Natural Products)

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18 pages, 1188 KiB

Open AccessArticle

The Influence of Exogenous Phenylalanine on the Accumulation of Secondary Metabolites in Agitated Shoot Cultures of Ruta graveolens L.

by Agnieszka Szewczyk, Wojciech Paździora and Halina Ekiert

Molecules 2023, 28(2), 727; https://doi.org/10.3390/molecules28020727 - 11 Jan 2023

Cited by 6 | Viewed by 1269

Abstract

This study aimed to examine the influence of the addition of a precursor (phenylalanine) on the accumulation of secondary metabolites in agitated shoot cultures of Ruta graveolens. Cultures were grown on Linsmaier and Skoog (LS) medium, with plant growth regulators (0.1 mg/L α-naphthaleneacetic [...] Read more.

This study aimed to examine the influence of the addition of a precursor (phenylalanine) on the accumulation of secondary metabolites in agitated shoot cultures of Ruta graveolens. Cultures were grown on Linsmaier and Skoog (LS) medium, with plant growth regulators (0.1 mg/L α-naphthaleneacetic acid—NAA—and 0.1 mg/L 6-benzylaminopurine—BAP). Phenylalanine was added to the cultures at a concentration of 1.25 g/L after 4 and 5 weeks of growth cycles. Biomass was collected after 2, 4, and 7 days of precursor addition. Both control and experimental cultures had the same secondary metabolites accumulated. Using the HPLC method, linear furanocoumarins (bergapten, isoimperatorin, isopimpinellin, psoralen, and xanthotoxin), furoquinoline alkaloids (γ-fagarine, 7-isopentenyloxy-γ-fagarine, and skimmianine), and catechin were detected and quantified in the methanolic extracts. In turn, phenolic acids, such as gallic acid, protocatechuic acid, p-hydroxybenzoic acid, syringic acid, p-coumaric acid, and ferulic acid were detected in hydrolysates. The production of phenolic acids and catechin (1.5-fold) was significantly increased by the addition of precursor, while there was no significant effect on the production of coumarins and alkaloids. The highest total content of phenolic acids (109 mg/100 g DW) was obtained on the second day of phenylalanine addition (the fourth week of growth cycles). The dominant phenolic compounds were p-coumaric acid (maximum content 64.3 mg/100 g DW) and ferulic acid (maximum content 35.6 mg/100 g DW). In the case of catechins, the highest total content (66 mg/100 g DW) was obtained on the third day of precursor addition (the fourth week of growth cycles). This study is the first to document the effect of feeding the culture medium with phenylalanine on the accumulation of bioactive metabolites in in vitro cultures of R. graveolens. Full article

(This article belongs to the Special Issue Phenolic/Polyphenolic Profile and Biological Activities of Natural Products)

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14 pages, 1341 KiB

Open AccessArticle

Constituents of Pulicaria inuloides and Cytotoxic Activities of Two Methoxylated Flavonols

by Janusz Malarz, Klaudia Michalska, Agnieszka Galanty, Anna Karolina Kiss and Anna Stojakowska

Molecules 2023, 28(2), 480; https://doi.org/10.3390/molecules28020480 - 04 Jan 2023

Cited by 3 | Viewed by 1692

Abstract

Plants of the genus Pulicaria are known for providing traditional medicines, spices, herbal teas, and insect deterrents. Pulicaria inuloides (Poir.). DC. is one of the less chemically studied species within the genus. Hydroalcoholic extracts from roots and aerial parts of P. inuloides were [...] Read more.

Plants of the genus Pulicaria are known for providing traditional medicines, spices, herbal teas, and insect deterrents. Pulicaria inuloides (Poir.). DC. is one of the less chemically studied species within the genus. Hydroalcoholic extracts from roots and aerial parts of P. inuloides were analyzed using the UHPLC-PAD-MSⁿ technique and revealed the presence of six caffeoylquinic and eleven caffeoylhexaric conjugates together with hydroxykaempferol dimethyl ether and quercetagetin trimethyl ether. Moreover, constituents of chloroform extract from the whole P. inuloides plants were isolated and identified by spectroscopic methods. One new and four known caryophyllene derivatives, three thymol derivatives, and four polymethoxylated flavonols were found in the analyzed extract. The structure of the new compound was established by spectroscopic methods (HRESIMS, ¹H NMR, ¹³C NMR, COSY, HSQC, HMBC, NOESY). The cytotoxicity of 6-Hydroxykaempferol 3,7-dimethyl ether and quercetagetin 3,7,3’-trimethyl ether (chrysosplenol C), which are major flavonols isolated from the plant, were tested on prostate epithelial cells (PNT2), prostate cancer cells (DU145 and PC3), human keratinocytes (HaCaT), and melanoma cells (HTB140 and A375). Both flavonols demonstrated moderate cytotoxic activity against PC3 cells (IC₅₀ = 59.5 µM and 46.6 µM, respectively). The remaining cell lines were less affected (IC₅₀ > 150 µM). Full article

(This article belongs to the Special Issue Phenolic/Polyphenolic Profile and Biological Activities of Natural Products)

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17 pages, 1761 KiB

Open AccessArticle

Evaluation of the Antioxidant, Cytoprotective and Antityrosinase Effects of Schisandra chinensis Extracts and Their Applicability in Skin Care Product

by Martyna Zagórska-Dziok, Magdalena Wójciak, Aleksandra Ziemlewska, Zofia Nizioł-Łukaszewska, Uliana Hoian, Katarzyna Klimczak, Dariusz Szczepanek and Ireneusz Sowa

Molecules 2022, 27(24), 8877; https://doi.org/10.3390/molecules27248877 - 14 Dec 2022

Cited by 8 | Viewed by 1603

Abstract

Plant extracts have been widely used for skin care for many centuries, and nowadays, they are commonly applied for the development and enrichment of new cosmetic preparations. The present study aimed the assessment of the biological activity of aqueous Schisandra chinensis extracts as [...] Read more.

Plant extracts have been widely used for skin care for many centuries, and nowadays, they are commonly applied for the development and enrichment of new cosmetic preparations. The present study aimed the assessment of the biological activity of aqueous Schisandra chinensis extracts as a potential ingredient of skin care products. The aspects studied involved the ability to neutralize free radicals, impact on viability and metabolism of keratinocytes, as well as tyrosinase inhibitory potential. Our study showed that aqueous S. chinensis extracts have a positive effect on keratinocyte growth and have high antioxidant potential and strong tyrosinase inhibitory activity. UPLC-MS analysis revealed that three groups of phenolic compounds were predominant in the analyzed extract, including lignans, phenolic acids and flavonoids and protocatechiuc and p-coumaryl quinic acids were predominant. Moreover, microwave-assisted extraction, followed by heat reflux extraction, was the most effective for extracting polyphenols. Furthermore, a prototypical natural body washes gel formulation containing the previously prepared extracts was developed. The irritation potential and viscosity were assessed for each of the formulations. The study demonstrated that the addition of these extracts to body wash gel formulations has a positive effect on their quality and may contribute to a decrease in skin irritation. In summary, S. chinensis aqueous extracts can be seen as an innovative ingredient useful in the cosmetic and pharmaceutical industry. Full article

(This article belongs to the Special Issue Phenolic/Polyphenolic Profile and Biological Activities of Natural Products)

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15 pages, 1035 KiB

Open AccessArticle

The Inhibition of α-Glucosidase, α-Amylase and Protein Glycation by Phenolic Extracts of Cotoneaster bullatus, Cotoneaster zabelii, and Cotoneaster integerrimus Leaves and Fruits: Focus on Anti-Hyperglycemic Activity and Kinetic Parameters

by Agnieszka Kicel, Anna Magiera, Marta Skrzywanek, Mariola Malczuk and Monika Anna Olszewska

Molecules 2022, 27(20), 7081; https://doi.org/10.3390/molecules27207081 - 20 Oct 2022

Cited by 8 | Viewed by 2431

Abstract

Cotoneaster species have gained significant importance in traditional Asian medicine for their ability to prevent and treat hyperglycemia and diabetes. Therefore, in this study, some aspects of the beneficial health effects of hydromethanolic extracts of C. bullatus, C. zabelii, and C. integerrimus [...] Read more.

Cotoneaster species have gained significant importance in traditional Asian medicine for their ability to prevent and treat hyperglycemia and diabetes. Therefore, in this study, some aspects of the beneficial health effects of hydromethanolic extracts of C. bullatus, C. zabelii, and C. integerrimus leaves and fruits were evaluated, including their influence on α-glucosidase, α-amylase, and nonenzymatic protein glycation. The activity was investigated in relation to the polyphenolic profile of the extracts determined by UV-spectrophotometric and HPLC-PDA-fingerprint methods. It was revealed that all leaf and fruit extracts are a promising source of biological components (caffeic acid pseudodepsides, proanthocyanidins, and flavonols), and the leaf extracts of C. bullatus and C. zabelii contain the highest levels of polyphenols (316.3 and 337.6 mg/g in total, respectively). The leaf extracts were also the most effective inhibitors of digestive enzymes and nonenzymatic protein glycation. IC₅₀ values of 8.6, 41.8, and 32.6 µg/mL were obtained for the most active leaf extract of C. bullatus (MBL) in the α-glucosidase, α-amylase, and glycation inhibition tests, respectively. In the kinetic study, MBL was displayed as a mixed-type inhibitor of both enzymes. The correlations between the polyphenol profiles and activity parameters (|r| > 0.72, p < 0.05) indicate a significant contribution of proanthocyanidins to the tested activity. These results support the traditional use of Cotoneaster leaves and fruits in diabetes and suggest their hydrophilic extracts be promising in functional applications. Full article

(This article belongs to the Special Issue Phenolic/Polyphenolic Profile and Biological Activities of Natural Products)

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13 pages, 1280 KiB

Open AccessArticle

Nutritional Profiling and Antioxidant Property of Three Wild Edible Mushrooms from North East India

by Joshua Khumlianlal, K. Chandradev Sharma, Leichombam Mohindro Singh, Pulok K. Mukherjee and Sarangthem Indira

Molecules 2022, 27(17), 5423; https://doi.org/10.3390/molecules27175423 - 25 Aug 2022

Cited by 5 | Viewed by 2259

Abstract

The mushroom is an important food for the rural tribal populations in Manipur, because of its high nutritional contents. In this study, we report on the nutritional profile of three wild edible mushrooms consumed by the tribal populations of Manipur viz.: Macrocybe gigantea [...] Read more.

The mushroom is an important food for the rural tribal populations in Manipur, because of its high nutritional contents. In this study, we report on the nutritional profile of three wild edible mushrooms consumed by the tribal populations of Manipur viz.: Macrocybe gigantea J124; Lactifluus leptomerus J201 and Ramaria thindii J470. The studied mushrooms possess a high protein content of 37.6%, 20.8% and 16.4%, respectively. They have a high vitamin C content with low vitamin B1, B2 and folic acid. Among the three mushrooms, M. gigantea J124 possesses the highest mineral content, followed by R. thindii J470 and L. leptomerus J201. The total phenolic content of L. leptomerus J201, M. gigantea J124 and R. thindii J470 were 26.206, 29.23 and 30.99 mg GAE/g, with flavonoid content of 6.646, 6.854 and 9.187 mg quercetin/g, respectively. R. thindii J470 has the highest TPC and TFC content, which correlates with its DPPH radical scavenging activity. The IC50 values for R. thindii J470, M. gigantea J124 and L. leptomerus J201 are 242.0 µg/mL, 550.4 µg/mL and 689.0 µg/mL, respectively, which suggest that the higher content of phenolic compounds in R. thindii J470 contributes to its radical scavenging properties. Full article

(This article belongs to the Special Issue Phenolic/Polyphenolic Profile and Biological Activities of Natural Products)

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14 pages, 1764 KiB

Open AccessArticle

Phenolic Profile and Fingerprint Analysis of Akebia quinata Leaves Extract with Endothelial Protective Activity

by Dan Gao, Chong-Woon Cho, Jin-Hyeok Kim, Haiying Bao, Hyung-Min Kim, Xiwen Li and Jong-Seong Kang

Molecules 2022, 27(14), 4636; https://doi.org/10.3390/molecules27144636 - 20 Jul 2022

Cited by 2 | Viewed by 1437

Abstract

In contrast to the stem and fruit of Akebia quinata, A. quinata leaves as a source rich in phenolic compounds with potentially beneficial pharmacological activities have been largely overlooked. To develop and use A. quinata leaves as a resource, we evaluated its [...] Read more.

In contrast to the stem and fruit of Akebia quinata, A. quinata leaves as a source rich in phenolic compounds with potentially beneficial pharmacological activities have been largely overlooked. To develop and use A. quinata leaves as a resource, we evaluated its potential as a cardiovascular-protective agent. Herein, we investigated the effects and potential mechanisms of A. quinata leaves extract on lipopolysaccharide (LPS)-induced inflammatory responses in human umbilical vein endothelial cells. We found that A. quinata leaves extract pretreatment of 10 μg/mL significantly attenuated LPS-induced protein expression of intercellular adhesion molecule-1, vascular cell adhesion molecule-1. Furthermore, this extract also suppressed LPS-induced phosphorylation of nuclear factor-κB p65. In order to elucidate the chemical profiles of the samples, the HPLC fingerprint was established, and prominent peaks were identified via HPLC–electrospray ionization–mass spectrometry. Multivariate statistical analyses, including hierarchical cluster analysis, principal component analysis, and partial least-squares discriminant analysis, were performed to evaluate the clustering of the samples. It was found that isochlorogenic acid C was a key marker for the classification of A. quinata leaves from the Gongju and Muju city in Korea. Collectively, this study not only suggested the potential of A. quinata leaves as a novel therapeutic candidate for inflammatory cardiovascular disease but also developed a quality control method for A. quinata leaves, which could help to expand the application of A. quinata. Full article

(This article belongs to the Special Issue Phenolic/Polyphenolic Profile and Biological Activities of Natural Products)

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19 pages, 1825 KiB

Open AccessArticle

Extra Virgin Olive Oil Secoiridoids Modulate the Metabolic Activity of Dacarbazine Pre-Treated and Treatment-Naive Melanoma Cells

by Azra Kugić, Sanja Dabelić, Cvijeta Jakobušić Brala, Nina Dabelić and Monika Barbarić

Molecules 2022, 27(10), 3310; https://doi.org/10.3390/molecules27103310 - 21 May 2022

Cited by 3 | Viewed by 2527

Abstract

Nowadays, many individuals, whether healthy or diagnosed with disease, tend to expose themselves to various easily accessible natural products in hopes of benefiting their health and well-being. Mediterranean populations have traditionally used olive oil not only in nutrition but also in cosmetics, including [...] Read more.

Nowadays, many individuals, whether healthy or diagnosed with disease, tend to expose themselves to various easily accessible natural products in hopes of benefiting their health and well-being. Mediterranean populations have traditionally used olive oil not only in nutrition but also in cosmetics, including skincare. In this study, the phenolic profile—composed of twelve compounds altogether, including the secoiridoids oleocanthal (OCAL) and oleacein (OCEIN)—of extra virgin olive oil (EVOO) from autochthonous cultivars from Croatia was determined using ¹H qNMR spectroscopy and HPLC-DAD analysis, and its biological activity was investigated in melanoma cell lines. The EVOO with the highest OCEIN content had the strongest anti-cancer activity in A375 melanoma cells and the least toxic effect on the non-cancerous keratocyte cell line (HaCaT). On the other hand, pure OCAL was shown to be more effective and safer than pure OCEIN. Post-treatment with any of the EVOO phenolic extracts (EVOO-PEs) enhanced the anti-cancer effect of the anti-cancerous drug dacarbazine (DTIC) applied in pre-treatment, while they did not compromise the viability of non-cancerous cells. The metastatic melanoma A375M cell line was almost unresponsive to the EVOO-PEs themselves, as well as to pure OCEIN and OCAL. Our results demonstrate that olive oils and/or their compounds may have a potentially beneficial effect on melanoma treatment. However, their usage can be detrimental or futile, especially in healthy cells, due to inadequately applied concentrations/combinations or the presence of resistant cells. Full article

(This article belongs to the Special Issue Phenolic/Polyphenolic Profile and Biological Activities of Natural Products)

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19 pages, 1838 KiB

Open AccessArticle

Polyphenol-Enriched Extracts of Prunus spinosa Fruits: Anti-Inflammatory and Antioxidant Effects in Human Immune Cells Ex Vivo in Relation to Phytochemical Profile

by Anna Magiera, Monika Ewa Czerwińska, Aleksandra Owczarek, Anna Marchelak, Sebastian Granica and Monika Anna Olszewska

Molecules 2022, 27(5), 1691; https://doi.org/10.3390/molecules27051691 - 04 Mar 2022

Cited by 16 | Viewed by 2792

Abstract

The fresh fruits of Prunus spinosa L., a wild plum species, are traditionally used for dietary purposes and medicinal applications in disorders related to inflammation and oxidative stress. This study aimed to investigate the phytochemical composition of the fruits in the function of [...] Read more.

The fresh fruits of Prunus spinosa L., a wild plum species, are traditionally used for dietary purposes and medicinal applications in disorders related to inflammation and oxidative stress. This study aimed to investigate the phytochemical composition of the fruits in the function of fractionated extraction and evaluate the biological potential of the extracts as functional products in two models of human immune cells ex vivo. Fifty-seven phenolic components were identified in the extracts by UHPLC-PDA-ESI-MS³, including twenty-eight new for the analysed fruits. Fractionation enabled the enrichment of polyphenols in the extracts up to 126.5 mg gallic acid equivalents/g dw total contents, 91.3 mg/g phenolic acids (caffeoyl-, coumaroyl-, and feruloylquinic acids), 41.1 mg/g flavonoids (mostly quercetin mono-, di- and triglycosides), 44.5 mg/g condensed proanthocyanidins, and 9.2 mg/g anthocyanins (cyanidin and peonidin glycosides). The hydroalcoholic extract and phenolic-enriched fractions of the fruits revealed significant ability to modulate pro-oxidant, pro-inflammatory, and anti-inflammatory functions of human neutrophils and peripheral blood mononuclear cells (PBMCs): they strongly downregulated the release of reactive oxygen species, TNF-α, and neutrophils elastase, upregulated the secretion of IL-10, and slightly inhibited the production of IL-8 and IL-6 in the cells stimulated by fMLP, fMLP+cytochalasin B, and LPS, depending on the test. Correlation studies and experiments on the pure compounds indicated a significant contribution of polyphenols to these effects. Moreover, cellular safety was confirmed for the extracts by flow cytometry in a wide range of concentrations. The results support the traditional use of fresh blackthorn fruits in inflammatory disorders and indicate extracts that are most promising for functional applications. Full article

(This article belongs to the Special Issue Phenolic/Polyphenolic Profile and Biological Activities of Natural Products)

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