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24 pages, 2755 KiB

Open AccessArticle

Antioxidant Activity, α-Glucosidase Inhibition and UHPLC–ESI–MS/MS Profile of Shmar (Arbutus pavarii Pamp)

by Nawal Buzgaia, Soo Yee Lee, Yaya Rukayadi, Faridah Abas and Khozirah Shaari

Plants 2021, 10(8), 1659; https://doi.org/10.3390/plants10081659 - 11 Aug 2021

Cited by 9 | Viewed by 2562

Abstract

The genus Arbutus (Ericaceae) has been traditionally used in folk medicine due to its phytomedicinal properties, especially Arbutus pavarii Pamp. However, this plant has not been evaluated for its efficacy, quality, and consistency to support the traditional uses, potentially in treating [...] Read more.

The genus Arbutus (Ericaceae) has been traditionally used in folk medicine due to its phytomedicinal properties, especially Arbutus pavarii Pamp. However, this plant has not been evaluated for its efficacy, quality, and consistency to support the traditional uses, potentially in treating diabetes. Despite previous studies that revealed the biological activities of A. pavarii as antioxidant and α-glucosidase inhibitory agents, scientific reports on the bioactive compounds that contribute to its health benefits are still scarce. Therefore, this research focused on the evaluation of antioxidant and α-glucosidase inhibitory activities of the methanol crude extracts and various fractions of the leaf and stem bark, as well as on metabolite profiling of the methanol crude extracts. The extracts and fractions were evaluated for total phenolic (TPC) and total flavonoid (TFC) contents, as well as the DPPH free radical scavenging, ferric reducing antioxidant power (FRAP), and α-glucosidase inhibitory activities. Methanol crude extracts of the leaf and stem bark were then subjected to UHPLC–ESI–MS/MS. To the best of our knowledge, the comparative evaluation of the antioxidant and α-glucosidase inhibitory activities of the leaf and stem bark of A. pavarii, as well as of the respective solvent fractions, is reported herein for the first time. Out of these extracts, the methanolic crude extracts and polar fractions (ethyl acetate and butanol fractions) showed significant bioactivities. The DPPH free radical and α-glucosidase inhibitions was highest in the leaf ethyl acetate fraction, with IC₅₀ of 6.39 and 4.93 µg/mL, respectively, while the leaf methanol crude extract and butanol fraction exhibited the highest FRAP with 82.95 and 82.17 mmol Fe (II)/g extract. The UHPLC–ESI–MS/MS analysis resulted in the putative identification of a total of 76 compounds from the leaf and stem bark, comprising a large proportion of plant phenolics (flavonoids and phenolic acids), terpenoids, and fatty acid derivatives. Results from the present study showed that the different parts of A. pavarii had potent antioxidant and α-glucosidase inhibitory activities, which could potentially prevent oxidative damage or diabetes-related problems. These findings may strengthen the traditional claim on the medicinal value of A. pavarii. Full article

(This article belongs to the Special Issue Composition and Biological Activities of Plant Secondary Metabolites)

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10 pages, 1822 KiB

Open AccessArticle

Ingol and Ingenol-Type Diterpenes from Euphorbia trigona Miller with Keratinocyte Inhibitory Activity

by Reham Hammadi, Norbert Kúsz, Csilla Zsuzsanna Dávid, Zoltán Behány, László Papp, Lajos Kemény, Judit Hohmann, Lóránt Lakatos and Andrea Vasas

Plants 2021, 10(6), 1206; https://doi.org/10.3390/plants10061206 - 14 Jun 2021

Cited by 9 | Viewed by 3132

Abstract

Ingenol mebutate, isolated from Euphorbia peplus, is an ingenane-type diterpenoid, primarily used for the topical treatment of actinic keratosis, a premalignant skin condition. The aim of our work was to investigate other Euphorbia species to find structurally similar diterpenes that can be [...] Read more.

Ingenol mebutate, isolated from Euphorbia peplus, is an ingenane-type diterpenoid, primarily used for the topical treatment of actinic keratosis, a premalignant skin condition. The aim of our work was to investigate other Euphorbia species to find structurally similar diterpenes that can be used as alternatives to ingenol mebutate. Pharmacological investigation of Euphorbia candelabrum, Euphorbia cotinifolia, Euphorbia ramipressa, and Euphorbia trigona revealed the potent keratinocyte (HPV-Ker cell line) inhibitory activity of these spurge species. From the methanolic extract of the aerial parts of Euphorbia trigona Miller, the most active species, five ingol (1–5) and four ingenane-type diterpenoids (6–9) were isolated by various chromatographic separation techniques, including open column chromatography, vacuum liquid chromatography, thin-layer chromatography, and high-performance liquid chromatography. The structures of the compounds were determined by NMR spectroscopic analysis and by comparison of the assignations with the literature data. The cytotoxic activity of the compounds against keratinocytes was tested in vitro by using ingenol mebutate as a positive control. Among the isolated compounds, two ingenane derivatives (6 and 7) exhibited remarkably stronger cytotoxic activity (IC₅₀ values 0.39 μM and 0.32 μM, respectively) on keratinocytes than ingenol mebutate (IC₅₀ value 0.84 μM). These compounds could serve as starting materials for further investigations to find alternatives to Picato^® (with active substance ingenol mebutate), which was withdrawn from marketing authorization in the European Union. Full article

(This article belongs to the Special Issue Composition and Biological Activities of Plant Secondary Metabolites)

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8 pages, 1310 KiB

Open AccessArticle

Anti-Inflammatory Effects of Berchemia floribunda in LPS-Stimulated RAW264.7 Cells through Regulation of NF-κB and MAPKs Signaling Pathway

by Hyun Ji Eo, Jun Hyuk Jang and Gwang Hun Park

Plants 2021, 10(3), 586; https://doi.org/10.3390/plants10030586 - 19 Mar 2021

Cited by 7 | Viewed by 2390

Abstract

Berchemia floribunda (Wall.) Brongn. (BF), which belongs to Rhamnaceae, is a special plant of Anmyeon Island in Korea. BF has been reported to have antioxidant and whitening effects. However, the anti-inflammatory activity of BR has not been elucidated. In this study, we evaluated [...] Read more.

Berchemia floribunda (Wall.) Brongn. (BF), which belongs to Rhamnaceae, is a special plant of Anmyeon Island in Korea. BF has been reported to have antioxidant and whitening effects. However, the anti-inflammatory activity of BR has not been elucidated. In this study, we evaluated the anti-inflammatory effect of leaves (BR-L), branches (BR-B) and fruit (BR-F) extracted with 70% ethanol of BR and elucidated the potential signaling pathway in LPS-induced RAW264.7 cells. BR-L showed a strong anti-inflammatory activity through the inhibition of NO production. BR-L significantly suppressed the production of the pro-inflammatory mediators such as iNOS, COX-2, IL-1β, IL-6 and TNF-α in LPS-stimulated RAW264.7 cells. BR-L suppressed the degradation and phosphorylation of IκB-α, which contributed to the inhibition of p65 nuclear accumulation and NF-κB activation. BR-L obstructed the phosphorylation of MAPKs (ERK1/2, p38 and JNK) in LPS-stimulated RAW264.7 cells. Consequently, these results suggest that BR-L may have great potential for the development of anti-inflammatory drugs to treat acute and chronic inflammatory disorders. Full article

(This article belongs to the Special Issue Composition and Biological Activities of Plant Secondary Metabolites)

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15 pages, 2823 KiB

Open AccessArticle

Effect of Seasonal Decrease in Temperature on the Content and Composition of Guayulins in Stems of Guayule (Parthenium argentatum, Gray)

by Juana Rozalén, M. Mercedes García-Martínez, Maria Engracia Carrión, Amaya Zalacain, Horacio López-Córcoles and Manuel Carmona

Plants 2021, 10(3), 537; https://doi.org/10.3390/plants10030537 - 12 Mar 2021

Cited by 9 | Viewed by 1762

Abstract

The guayulins are a family of sesquiterpene compounds that consist of an isoprenoid nucleus substituted either by trans-cinnamic or p-anisic acid, and are present only in the resinous fraction of the rubber plant guayule (Parthenium argentatum, Gray). While the [...] Read more.

The guayulins are a family of sesquiterpene compounds that consist of an isoprenoid nucleus substituted either by trans-cinnamic or p-anisic acid, and are present only in the resinous fraction of the rubber plant guayule (Parthenium argentatum, Gray). While the natural role of the guayulins remains enigmatic, they may serve as a defense function against other plants or herbivores by virtue of the accumulation of cinnamic acid. Prior research has suggested seasonal variation in guayulin content, which has been shown to decrease as winter arrives in two different varieties. In the present study, the effect of guayulins has been evaluated in 13 different accessions cultivated under the same conditions during autumn. A general reduction in guayulin content was found in the stems from all varieties between the September and November harvest, which was accompanied by an increase in the resin content. With respect to individual guayulins, while guayulin A was the most prominent member during most of the year, guayulin C had more prominence when temperature started to decrease. In this seasonal period, the production of each member of the guayulin family in the leaves was very balanced. Full article

(This article belongs to the Special Issue Composition and Biological Activities of Plant Secondary Metabolites)

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16 pages, 1369 KiB

Open AccessEditor’s ChoiceArticle

Endemic Veronica saturejoides Vis. ssp. saturejoides–Chemical Composition and Antioxidant Activity of Free Volatile Compounds

by Marija Nazlić, Dario Kremer, Renata Jurišić Grubešić, Barbara Soldo, Elma Vuko, Edith Stabentheiner, Dalibor Ballian, Faruk Bogunić and Valerija Dunkić

Plants 2020, 9(12), 1646; https://doi.org/10.3390/plants9121646 - 25 Nov 2020

Cited by 14 | Viewed by 2594

Abstract

Chemical profile and antioxidant activity of the species Veronica saturejoides Vis. ssp. saturejoides (Plantaginaceae)—which is endemic to Croatia, Bosnia and Herzegovina and Montenegro —were investigated. Volatile compounds produced by glandular trichomes (composed of one stalk cell and two elliptically formed head cells according [...] Read more.

Chemical profile and antioxidant activity of the species Veronica saturejoides Vis. ssp. saturejoides (Plantaginaceae)—which is endemic to Croatia, Bosnia and Herzegovina and Montenegro —were investigated. Volatile compounds produced by glandular trichomes (composed of one stalk cell and two elliptically formed head cells according to scanning electron microscope investigation) were isolated from the plants collected in two locations. Additionally, as a part of specialized metabolites, total polyphenols, total tannins, total flavonoids and total phenolic acids were determined spectrophotometrically. In the lipophilic volatile fractions-essential oils, the most abundant compounds identified were hexahydrofarnesyl acetone, caryophyllene oxide and hexadecanoic acid. In total, the class of oxygenated sesquiterpenes and the group of fatty aldehydes, acids and alcoholic compounds dominated in the essential oils. In the hydrophilic volatile fractions-hydrosols, the most abundant compounds identified were trans-p-mentha-1(7),8-dien-2-ol, allo-aromadendrene and (E)-caryophyllene. A group of oxygenated monoterpenes and the sesquiterpene hydrocarbons dominated in the hydrosols. Antioxidant activity of essential oils and hydrosols was tested with two methods: 2,2′-diphenyl-1-picrylhydrazyl (DPPH) and oxygen radical absorbance capacity (ORAC). Essential oils showed higher antioxidant activity than hydrosols and showed similar antioxidant activity to Rosmarinus officinalis essential oil. Obtained results demonstrate that this genus is a potential source of volatiles with antioxidant activity. Full article

(This article belongs to the Special Issue Composition and Biological Activities of Plant Secondary Metabolites)

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11 pages, 1325 KiB

Open AccessArticle

Medicinal Properties of Lilium candidum L. and Its Phytochemicals

by Michele Zaccai, Ludmila Yarmolinsky, Boris Khalfin, Arie Budovsky, Jonathan Gorelick, Arik Dahan and Shimon Ben-Shabat

Plants 2020, 9(8), 959; https://doi.org/10.3390/plants9080959 - 29 Jul 2020

Cited by 19 | Viewed by 7340

Abstract

Lilium candidum L., known as Madonna, meadow, or white lily, is a bulbous plant from the Liliaceae family, originating in the Middle East. L. candidum has been abundantly used in folk medicine since ancient times to relieve a variety of ailments, including age-related [...] Read more.

Lilium candidum L., known as Madonna, meadow, or white lily, is a bulbous plant from the Liliaceae family, originating in the Middle East. L. candidum has been abundantly used in folk medicine since ancient times to relieve a variety of ailments, including age-related diseases, burns, ulcers, and coughs. The aim of this article is to investigate the anti-inflammatory and anti-diabetic activities of L. candidum extracts and its active phytochemicals. Some active volatile phytochemicals were identified using gas chromatography–mass spectrometry (GC-MS) analysis. Significant (p < 0.001) anti-diabetic properties of the extracts kaempferol, linalool, citronellal, and humulene were demonstrated by an elevation in glucose uptake by adipocytes. The significant (p < 0.01) effect of the plant extracts kaempferol, citronellal, and humulene on the secretion of pro-inflammatory cytokines interleukin 6 (IL-6) and interleukin 8 (IL-8) was demonstrated using enzyme-linked immunosorbent assay. Altogether, L. candidum and its rich collection of phytochemicals hold promising medicinal potential, and further investigations of its therapeutic prospects are encouraged. Full article

(This article belongs to the Special Issue Composition and Biological Activities of Plant Secondary Metabolites)

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15 pages, 2043 KiB

Open AccessArticle

In Vitro Antimicrobial and Antiproliferative Activities of the Root Bark Extract and Isolated Chemical Constituents of Zanthoxylum paracanthum Kokwaro (Rutaceae)

by Magrate M. Kaigongi, Catherine W. Lukhoba, Souaibou Yaouba, Nokwanda P. Makunga, Joseph Githiomi and Abiy Yenesew

Plants 2020, 9(7), 920; https://doi.org/10.3390/plants9070920 - 21 Jul 2020

Cited by 37 | Viewed by 3802

Abstract

Zanthoxylum paracanthum Kokwaro (Rutaceae) is an endemic Kenyan and Tanzanian plant used in folk medicine by local populations. Although other Zanthoxylum species have been studied, only Z. paracantum stem extracts have been profiled, even though the roots are also used as herbal remedies. [...] Read more.

Zanthoxylum paracanthum Kokwaro (Rutaceae) is an endemic Kenyan and Tanzanian plant used in folk medicine by local populations. Although other Zanthoxylum species have been studied, only Z. paracantum stem extracts have been profiled, even though the roots are also used as herbal remedies. As root extracts may be another source of pharmaceutical compounds, the CH₂Cl₂/MeOH (1:1) root bark extract was studied in this report. Eight root bark compounds were isolated and their structural identities were confirmed by mass spectrometry (MS) and nuclear magnetic resonance (NMR) (using COSY, HSQC, NOESY and HMBC) analyses. The structural identities were determined as follows: the fatty acid—myristic acid (1); the sterol—stigmasterol (2); the lignan—sesamin (3); two β-carboline alkaloids—10-methoxycanthin-6-one (6) and canthin-6-one (7); and three phenanthridine alkaloids—8-acetonyldihydrochelerythrine (4), arnottianamide (5) and 8-oxochelerythrine (8). Some of these compounds were identified in the species for the first time. These compounds and the extract were then tested in vitro against methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli (ATCC 25922), Staphylococcus aureus (ATCC 29213) and Candida albicans (ATCC 10231) before tests for antiproliferative activity against the human breast cancer (HCC 1395), human prostate cancer (DU 145) and normal (Vero E6) cell lines were conducted. Minimum inhibition concentration values of 3.91, 1.95, 0.98 and 7.81 µg/mL against MRSA, S. aureus, E. coli and C. albicans, respectively, were recorded. Among the isolates, canthin-6-one was the most active, followed by 10-methoxycanthin-6-one. The root extract and some of the compounds also had antiproliferative activity against the HCC 1395 cell line. Stigmasterol and canthin-6-one had IC₅₀ values of 7.2 and 0.42. The root bark extract also showed activity, at 8.12 µg/mL, against the HCC 1395 cells. Out of the chemical isolates, 10-methoxycanthin-6-one and canthin-6-one showed the strongest inhibition of the DU 145 cells. The root extract had significant antimicrobial and antiproliferative activities, supporting the traditional use of this plant in treating microbial infections and cancer-related ailments. Full article

(This article belongs to the Special Issue Composition and Biological Activities of Plant Secondary Metabolites)

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Review

Jump to: Research

21 pages, 1968 KiB

Open AccessReview

The Genus Lagochilus (Lamiaceae): A Review of Its Diversity, Ethnobotany, Phytochemistry, and Pharmacology

by Nilufar Z. Mamadalieva, Davlat Kh. Akramov, Ludger A. Wessjohann, Hidayat Hussain, Chunlin Long, Komiljon Sh. Tojibaev, Elham Alshammari, Mohamed L. Ashour and Michael Wink

Plants 2021, 10(1), 132; https://doi.org/10.3390/plants10010132 - 11 Jan 2021

Cited by 7 | Viewed by 3817

Abstract

The genus Lagochilus (Lamiaceae) is native to Central, South-Central, and Eastern Asia. It comprises 44 species, which have been commonly used as herbal medicines for the treatments of various ailments for thousands of years, especially in Asian countries. This review aims to summarize [...] Read more.

The genus Lagochilus (Lamiaceae) is native to Central, South-Central, and Eastern Asia. It comprises 44 species, which have been commonly used as herbal medicines for the treatments of various ailments for thousands of years, especially in Asian countries. This review aims to summarize the chemical constituents and pharmacological activities of species from the genus Lagochilus to unveil opportunities for future research. In addition, we provide some information about their traditional uses, botany, and diversity. More than 150 secondary metabolites have been reported from Lagochilus, including diterpenes, flavonoids, phenolic compounds, triterpenoids, iridoid glycosides, lignans, steroids, alkaloids, polysaccharides, volatile, non-volatile and aromatic compounds, lipids, carbohydrates, minerals, vitamins, and other secondary metabolites. In vitro and in vivo pharmacological studies on the crude extracts, fractions, and isolated compounds from Lagochilus species showed hemostatic, antibacterial, anti-inflammatory, anti-allergic, cytotoxic, enzyme inhibitory, antispasmodic, hypotensive, sedative, psychoactive, and other activities. Full article

(This article belongs to the Special Issue Composition and Biological Activities of Plant Secondary Metabolites)

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19 pages, 591 KiB

Open AccessFeature PaperReview

Secondary Bioactive Metabolites from Plant-Derived Food Byproducts through Ecopharmacognostic Approaches: A Bound Phenolic Case Study

by Ilaria Burlini and Gianni Sacchetti

Plants 2020, 9(9), 1060; https://doi.org/10.3390/plants9091060 - 19 Aug 2020

Cited by 7 | Viewed by 2818

Abstract

The climate emergency and the risks to biodiversity that the planet is facing nowadays, have made the management of food resources increasingly complex but potentially interesting. According to FAO, one-third of the edible parts of food produced throughout the whole food supply chain [...] Read more.

The climate emergency and the risks to biodiversity that the planet is facing nowadays, have made the management of food resources increasingly complex but potentially interesting. According to FAO, one-third of the edible parts of food produced throughout the whole food supply chain gets lost or wasted globally every year. At the same time, demographic growth makes it necessary to change course toward sustainable economic development in order to satisfy market demands. The European Union supported the idea of a Circular Economy from 2015 and arranged annual Action Plans toward a greener, climate-neutral economy. Following the biorefinery concept, food waste becomes byproducts that can be recovered and exploited as high added-value materials for industrial applications. The use of sustainable extraction processes to manage food byproducts is a task that research has to support through the development of low environmental impact strategies. This review, therefore, aims to take stock of the possibilities of extracting molecules from food waste biomass following ecopharmacognostic approaches inspired by green chemistry guidelines. In particular, the use of innovative hybrid techniques to maximize yields and minimize the environmental impact of processes is reviewed, with a focus on bound phenolic extractions. Full article

(This article belongs to the Special Issue Composition and Biological Activities of Plant Secondary Metabolites)

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