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15 pages, 784 KiB

Open AccessArticle

Phytotoxic and Antimicrobial Activities of Teucrium polium and Thymus decussatus Essential Oils Extracted Using Hydrodistillation and Microwave-Assisted Techniques

by Ibrahim Saleh, Ahmed Abd-ElGawad, Abd El-Nasser El Gendy, Abeer Abd El Aty, Tarik Mohamed, Hazem Kassem, Fahd Aldosri, Abdelsamed Elshamy and Mohamed-Elamir F. Hegazy

Plants 2020, 9(6), 716; https://doi.org/10.3390/plants9060716 - 4 Jun 2020

Cited by 35 | Viewed by 4085

Abstract

Essential oils (EOs) have been described as promising eco-friendly secondary products of aromatic plants with several biological activities. The present study aimed to characterize the chemical composition and explore phytotoxic and antimicrobial activities of Teucrium polium and Thymus decussatus EOs extracted using hydrodistillation [...] Read more.

Essential oils (EOs) have been described as promising eco-friendly secondary products of aromatic plants with several biological activities. The present study aimed to characterize the chemical composition and explore phytotoxic and antimicrobial activities of Teucrium polium and Thymus decussatus EOs extracted using hydrodistillation (HD) and microwave-assisted extraction (MAE) methods. Twenty-seven and twenty-eight compounds were identified from HD and MAE extracted EOs of T. polium, respectively. The oxygenated sesquiterpenes (57.68%) were characterized as the main components of the hydrodistilled EO with a prominence of 6-epi-shyobunol (33.00%), while sesquiterpene hydrocarbons (54.48%) were the main components of the MAE method, with a prominence of delta-cadinene (25.13%). Eighteen and nineteen compounds, were characterized in T. decussatus EOs extracted using HD and MAE methods, respectively, and oxygenated monoterpenes represented the main components of both EOs with carvacrol (94.40% and 75.91%, respectively) as the main compound. The EOs extracted using the MAE method were slightly more phytotoxic than those extracted using the HD method. The T. decussatus EO extracted using the MAE method showed a higher inhibitory effect than T. polium by 16-, 32-, and 24-fold, regarding seed germination, shoot, and root growth of lettuce, respectively. Moreover, EOs extracted by HD method showed a similar pattern with 16-, 28-, and 14-fold effects. Both T. decussatus EOs exhibited potent inhibitory effect against all tested bacteria with an inhibition zone of 34–39 mm and the lowest minimum inhibitory concentration (MIC) of 0.49, 0.98, and 1.95 μg/mL against Aspergillus niger, Escherichia coli, and Staphylococcus aureus, respectively. However, the EOs of T. polium showed weak antibacterial activity and no antifungal effect. Further studies are needed for the characterization of bioactive major compounds, either singular or synergistic, at field scale and to determine their modes of action and safety. Full article

(This article belongs to the Special Issue Bioactive Compounds in Plants)

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31 pages, 3169 KiB

Open AccessEditor’s ChoiceArticle

Bioactive Compounds and Aroma Profile of Some Lamiaceae Edible Flowers

by Ilaria Marchioni, Basma Najar, Barbara Ruffoni, Andrea Copetta, Luisa Pistelli and Laura Pistelli

Plants 2020, 9(6), 691; https://doi.org/10.3390/plants9060691 - 28 May 2020

Cited by 51 | Viewed by 5999

Abstract

Edible flowers are consumed for their appearance, colours, nutritional and healthy properties, but the use is limited by the actual number of the species. Seven edible flowers of the Lamiaceae family (Ocimeae and Mentheae tribes) were investigated: Monarda didyma ‘Fireball’, Nepeta × faassenii [...] Read more.

Edible flowers are consumed for their appearance, colours, nutritional and healthy properties, but the use is limited by the actual number of the species. Seven edible flowers of the Lamiaceae family (Ocimeae and Mentheae tribes) were investigated: Monarda didyma ‘Fireball’, Nepeta × faassenii ‘Six Hills Giant’, Ocimum basilicum ‘Blue Spice’, O. basilicum ‘Cinnamon’, Ocimum × citriodorum, Salvia discolor, and Salvia microphylla ‘Hot Lips’. Total soluble sugars, proteins, polyphenols, carotenoids, ascorbic acid and antioxidant activity were detected. The species of the Mentheae tribe contained higher sugar content than Ocimeae flowers, the opposite with regard to protein content. Ocimeae tribe flowers showed high polyphenols and carotenoids content. The Ocimeae tribe together with two specie of the Mentheae tribe showed an aroma profile dominated by sesquiterpene hydrocarbons (58.0% in S. discolor to 77.9% in Ocimum × citriodorum). Oxygenated monoterpenes prevailed in Nepeta and Monarda, also present in the essential oil of this latter species (84.5%). By contrast, Nepeta and S. discolor evidenced non-terpenes as the principal class (41.2% and 77.5%, respectively), while the oxygenated sesquiterpene was the main one in S. microphylla. The two varieties of Ocimum spp. showed oxygenated monoterpenes as the main class of volatiles. Full article

(This article belongs to the Special Issue Bioactive Compounds in Plants)

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20 pages, 304 KiB

Open AccessArticle

Chemical Compositions, Mosquito Larvicidal and Antimicrobial Activities of Leaf Essential Oils of Eleven Species of Lauraceae from Vietnam

by Dao Thi Minh Chau, Nguyen Thanh Chung, Le Thi Huong, Nguyen Huy Hung, Isiaka A. Ogunwande, Do Ngoc Dai and William N. Setzer

Plants 2020, 9(5), 606; https://doi.org/10.3390/plants9050606 - 10 May 2020

Cited by 36 | Viewed by 5075

Abstract

The Lauraceae is a family rich in aromatic and medicinal plants. Likewise, essential oils derived from members of this family have demonstrated a myriad of biological activities. It is hypothesized that members of the Lauraceae from Vietnam will yield essential oils that may [...] Read more.

The Lauraceae is a family rich in aromatic and medicinal plants. Likewise, essential oils derived from members of this family have demonstrated a myriad of biological activities. It is hypothesized that members of the Lauraceae from Vietnam will yield essential oils that may be useful in controlling mosquito populations and treating microbial infections. In this work, the leaf essential oils of eleven species of Lauraceae (Beilschmiedia erythrophloia, B. robusta, B. yunnanensis, Cryptocarya concinna, C. impressa, C. infectoria, Litsea viridis, Machilus balansa, M. grandifolia, Neolitsea ellipsoidea, and Phoebe angustifolia) have been obtained by hydrodistillation and the chemical compositions analyzed by gas chromatography – mass spectrometry (GC-MS) and gas chromatography with flame ionization detection (GC-FID). The essential oils were screened for larvicidal activity against Aedes aegypti, Ae. albopictus, and Culex quinquefasciatus, and for antimicrobial activity against Enterococcus faecalis, Staphylococcus aureus, Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica, and Candida albicans. The leaf essential oil of N. ellipsoidea, rich in (E)-β-ocimene (87.6%), showed excellent larvicidal activity against Ae. aegypti with a 24 h LC₅₀ of 6.59 μg/mL. The leaf essential oil of C. infectoria, dominated by germacrene D (55.5%) and bicyclogermacrene (11.4%), exhibited remarkable larvicidal activity against Cx. quinquefasciatus (48 h LC₅₀ = 0.40 μg/mL). N. ellipsoidea leaf essential oil also demonstrated notable antibacterial activity against E. faecalis and B. cereus with minimum inhibitory concentration (MIC) values of 16 μg/mL, while the leaf essential oil of C. impressa showed excellent anticandidal with an MIC of 16 μg/mL. Leaf essential oils from the Lauraceae should be considered for utilization as alternative agents for controlling mosquito populations and as antimicrobial agents. Full article

(This article belongs to the Special Issue Bioactive Compounds in Plants)

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23 pages, 1597 KiB

Open AccessArticle

Phenolic Profile, Toxicity, Enzyme Inhibition, In Silico Studies, and Antioxidant Properties of Cakile maritima Scop. (Brassicaceae) from Southern Portugal

by Chloé Placines, Viana Castañeda-Loaiza, Maria João Rodrigues, Catarina G. Pereira, Azzurra Stefanucci, Adriano Mollica, Gokhan Zengin, Eulogio J. Llorent-Martínez, Paula C. Castilho and Luísa Custódio

Plants 2020, 9(2), 142; https://doi.org/10.3390/plants9020142 - 22 Jan 2020

Cited by 26 | Viewed by 4686

Abstract

Cakile maritima Scop. (sea rocket) is an edible halophyte plant with several ethnomedicinal uses. This work reports the chemical profile and bioactivities of food grade extracts from sea rocket organs. Toxicity was determined on mammalian cells, and phenolic profiling and the quantitation of [...] Read more.

Cakile maritima Scop. (sea rocket) is an edible halophyte plant with several ethnomedicinal uses. This work reports the chemical profile and bioactivities of food grade extracts from sea rocket organs. Toxicity was determined on mammalian cells, and phenolic profiling and the quantitation of the main metabolites were made by high-performance liquid chromatography coupled to mass spectrometry (HPLC-MS). Enzymatic inhibition was determined towards acetyl- and butyrylcholinesterase (AChE, BuChE), α-glucosidase, α-amylase, and tyrosinase. Docking studies were performed to tyrosinase, on the major metabolites, and samples were tested for antioxidant properties. Extracts were not toxic, were constituted mainly by flavonoids, and some compounds (roseoside and oleuropein) are here described for the first time in the species. The aerial organs’ ethanol extract had relevant activity towards 2,2-diphenyl-1-picrylhydrazyl [DPPH, half maximal inhibitory concentration (IC₅₀) = 0.59 mg/mL], and ferric-reducing activity power (FRAP, IC₅₀ = 0.99 mg/mL). All samples were more active towards AChE than on BuChE. The ethanol fruits’ extract inhibited α-glucosidase [2.19 mmol of equivalent of acarbose (ACAE)/g]. Samples were active against tyrosinase, especially the aerial organs’ ethanol extracts [25.9 mg of equivalent of kojic acid (KAE)/g]. Quercetin and kaempferol glycosides fit well into the enzymatic pocket of tyrosinase. Our results suggest sea rocket as a candidate to be further explored as a source of bioactive products. Full article

(This article belongs to the Special Issue Bioactive Compounds in Plants)

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15 pages, 1087 KiB

Open AccessArticle

Inhibition of Digestive Enzymes and Antioxidant Activity of Extracts from Fruits of Cornus alba, Cornus sanguinea subsp. hungarica and Cornus florida–A Comparative Study

by Joanna Truba, Iwona Stanisławska, Marta Walasek, Wioleta Wieczorkowska, Konrad Woliński, Tina Buchholz, Matthias F. Melzig and Monika E. Czerwińska

Plants 2020, 9(1), 122; https://doi.org/10.3390/plants9010122 - 18 Jan 2020

Cited by 9 | Viewed by 4490

Abstract

The fruits of some Cornus species (dogwoods) are used in traditional medicine and considered potential anti-diabetic and hypolipemic agents. The aim of the study was to determine the ability of extracts from Cornus alba (CA), Cornus florida (CF), and Cornus sanguinea (CS) to [...] Read more.

The fruits of some Cornus species (dogwoods) are used in traditional medicine and considered potential anti-diabetic and hypolipemic agents. The aim of the study was to determine the ability of extracts from Cornus alba (CA), Cornus florida (CF), and Cornus sanguinea (CS) to inhibit digestive enzymes namely α-amylase, pancreatic lipase, and α-glucosidase, as well as isolation of compounds from plant material with the strongest effect. In addition, the phytochemical profile and antioxidant activity of extracts from three dogwoods were compared with HPLC-DAD-MS/MS and DPPH scavenging assay, respectively. Among the aqueous-ethanolic extracts, the activity of α-amylase was the most strongly inhibited by the fruit extract of CA (IC₅₀ = 115.20 ± 14.31 μg/mL) and the activity of α-glucosidase by the fruit of CF (IC₅₀ = 38.87 ± 2.65 μg/mL). Some constituents of CA fruit extract, such as coumaroylquinic acid, kaempferol, and hydroxytyrosol derivatives, were isolated. Among the three species of dogwood studied, the greatest biological potential was demonstrated by CA extracts, which are sources of phenolic acids and flavonoid compounds. In contrast, iridoid compounds or flavonoid glycosides found in fruits of CF or CS extracts do not play a significant role in inhibiting digestive enzymes but exert antioxidant activity. Full article

(This article belongs to the Special Issue Bioactive Compounds in Plants)

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13 pages, 4526 KiB

Open AccessArticle

Simalikalactone D, a Potential Anticancer Compound from Simarouba tulae, an Endemic Plant of Puerto Rico

by Belmari Mendez, Jeyshka Reyes, Isabel Conde, Zulma Ramos, Eunice Lozada, Ailed M. Cruz, Gabriela Asencio, Augusto Carvajal, Suranganie Dharmawardhane, Dalice M. Piñero-Cruz, Eliud Hernández, Pablo Vivas and Claudia A. Ospina

Plants 2020, 9(1), 93; https://doi.org/10.3390/plants9010093 - 11 Jan 2020

Cited by 3 | Viewed by 4403

Abstract

Species of the genus Simarouba have been studied because of their antimalarial and antileukemic activities. A group of oxygenated terpenes called quassinoids have been isolated from species of the Simarouba genus, and are responsible for its therapeutic properties. We hypothesized that Simarouba tulae [...] Read more.

Species of the genus Simarouba have been studied because of their antimalarial and antileukemic activities. A group of oxygenated terpenes called quassinoids have been isolated from species of the Simarouba genus, and are responsible for its therapeutic properties. We hypothesized that Simarouba tulae, an endemic plant from Puerto Rico, is a natural source rich in quassinoid compounds with anticancer activity. The leaves were processed and extracted with solvents of different polarities. The extracts were screened for their antiproliferative activity, and it was shown that the chloroform extract was the most active extract. This extract was purified using different chromatographic techniques to afford the quassinoid simalikalactone D (SKD). This compound was further characterized using NMR and X-ray diffraction analysis. A reassessment of original structural assignments for SKD is proposed. SKD showed high cytotoxicity activity, with an IC₅₀ of 55, 58, and 65 nM in A2780CP20 (ovarian), MDA-MB-435 (breast), and MDA-MB-231 (breast) cell lines, respectively. Exposure to SKD led to 15% inhibition of the migration of MDA-MB-231 cells. Full article

(This article belongs to the Special Issue Bioactive Compounds in Plants)

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23 pages, 1937 KiB

Open AccessArticle

Antitumor Potential and Phytochemical Profile of Plants from Sardinia (Italy), a Hotspot for Biodiversity in the Mediterranean Basin

by Concettina Cappadone, Manuela Mandrone, Ilaria Chiocchio, Cinzia Sanna, Emil Malucelli, Vincenza Bassi, Giovanna Picone and Ferruccio Poli

Plants 2020, 9(1), 26; https://doi.org/10.3390/plants9010026 - 24 Dec 2019

Cited by 18 | Viewed by 4184

Abstract

Sardinia (Italy), with its wide range of habitats and high degree of endemism, is an important area for plant-based drug discovery studies. In this work, the antitumor activity of 35 samples from Sardinian plants was evaluated on human osteosarcoma cells U2OS. The results [...] Read more.

Sardinia (Italy), with its wide range of habitats and high degree of endemism, is an important area for plant-based drug discovery studies. In this work, the antitumor activity of 35 samples from Sardinian plants was evaluated on human osteosarcoma cells U2OS. The results showed that five plants were strongly antiproliferative: Arbutus unedo (AuL), Cynara cardunculus (CyaA), Centaurea calcitrapa (CcA), Smilax aspera (SaA), and Tanacetum audibertii (TaA), the latter endemic to Sardinia and Corsica. Thus, their ability to induce cell cycle arrest and apoptosis was tested. All extracts determined cell cycle block in G2/M phase. Nevertheless, the p53 expression levels were increased only by TaA. The effector caspases were activated mainly by CycA, TaA, and CcA, while AuL and SaA did not induce apoptosis. The antiproliferative effects were also tested on human umbilical vein endothelial cells (HUVEC). Except for AuL, all the extracts were able to reduce significantly cell population, suggesting a potential antiangiogenic activity. The phytochemical composition was first explored by ¹H NMR profiling, followed by further purifications to confirm the structure of the most abundant metabolites, such as phenolic compounds and sesquiterpene lactones, which might play a role in the measured bioactivity. Full article

(This article belongs to the Special Issue Bioactive Compounds in Plants)

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13 pages, 2844 KiB

Open AccessArticle

Nutritional Value, Mineral Composition, Secondary Metabolites, and Antioxidant Activity of Some Wild Geophyte Sedges and Grasses

by Saud L. Al-Rowaily, Ahmed M. Abd-ElGawad, Suliman M. Alghanem, Wafa’a A. Al-Taisan and Yasser A. El-Amier

Plants 2019, 8(12), 569; https://doi.org/10.3390/plants8120569 - 4 Dec 2019

Cited by 23 | Viewed by 4977

Abstract

Geophytes are plants with underground storage organs including bulbs, corms, tubers, and rhizomes, often physiologically active and able to survive during harsh environmental conditions. This study is conducted to assess the nutritive value, mineral composition, bioactive metabolites, and antioxidant activity of five wild [...] Read more.

Geophytes are plants with underground storage organs including bulbs, corms, tubers, and rhizomes, often physiologically active and able to survive during harsh environmental conditions. This study is conducted to assess the nutritive value, mineral composition, bioactive metabolites, and antioxidant activity of five wild geophytes (Cyperus capitatus, C. conglomeratus, Elymus farctus, Lasiurus scindicus, and Panicum turgidum) collected from the Nile Delta coast and inland desert. The proximate composition including dry matter, moisture content, ash content, fiber, fat, protein, sucrose, and glucose were determined. Also, total carbohydrates, total digestible nutrients (TDN), and nutritive values were calculated. Macro- and micro-minerals were also determined in the studied geophytes. Total phenolics, total flavonoids, alkaloids, saponins, and tannins were determined. Antioxidant activity was evaluated based on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicle scavenging. Based on the nutritive value, the studied geophytes are ranked as follows: E. farctus > C. conglomeratus > L. scindicus > P. turgidum > C. capitatus. The mineral analysis reveals a sufficient amount of macro- and micro-elements in the studied geophytes while the microelements levels in the studied wild plants exist as Fe > Mn > Zn > Cu. Cyperus conglomeratus attained the highest concentrations of all determined secondary metabolites. On the other hand, C. conglomeratus, C. capitatus, and P. turgidum extracts showed strong scavenging activity (EC₅₀ < 1 mg mL⁻¹), while extracts of E. farctus and L. scindicus exhibited moderate scavenging activity (1 ≤ EC₅₀ ≤ 2 mg mL⁻¹). The present data reveal that geophytes under investigation could be used as good forage plants, especially in arid habitats. In addition, C. conglomeratus could be a potentially important candidate for natural antioxidants as it attained high contents of the bioactive constituents. Full article

(This article belongs to the Special Issue Bioactive Compounds in Plants)

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12 pages, 1486 KiB

Open AccessArticle

Ginkgo biloba L. Leaf Extract Protects HepG2 Cells Against Paraquat-Induced Oxidative DNA Damage

by Amélia M. Silva, Sandra C. Silva, Jorge P. Soares, Carlos Martins-Gomes, João Paulo Teixeira, Fernanda Leal and Isabel Gaivão

Plants 2019, 8(12), 556; https://doi.org/10.3390/plants8120556 - 29 Nov 2019

Cited by 19 | Viewed by 4862

Abstract

Ginkgo biloba L. leaf extracts and herbal infusions are used worldwide due to the health benefits that are attributed to its use, including anti-neoplastic, anti-aging, neuro-protection, antioxidant and others. The aim of this study was to evaluate the effect of an aqueous Ginkgo [...] Read more.

Ginkgo biloba L. leaf extracts and herbal infusions are used worldwide due to the health benefits that are attributed to its use, including anti-neoplastic, anti-aging, neuro-protection, antioxidant and others. The aim of this study was to evaluate the effect of an aqueous Ginkgo biloba extract on HepG2 cell viability, genotoxicity and DNA protection against paraquat-induced oxidative damage. Exposure to paraquat (PQ), over 24 h incubation at 1.0 and 1.5 µM, did not significantly reduce cell viability but induced concentration and time-dependent oxidative DNA damage. Ginkgo biloba leaf extract produced dose-dependent cytotoxicity (IC₅₀ = 540.8 ± 40.5 µg/mL at 24 h exposure), and short incubations (1 h) produced basal and oxidative DNA damage (>750 and 1500 µg/mL, respectively). However, lower concentrations (e.g., 75 µg/mL) of Ginkgo biloba leaf extract were not cytotoxic and reduced basal DNA damage, indicating a protective effect at incubations up to 4 h. On the other hand, longer incubations (24 h) induced oxidative DNA damage. Co-incubation of HepG2 cells for 4 h, with G. biloba leaf extract (75 µg/mL) and PQ (1.0 or 1.5 µM) significantly reduced PQ-induced oxidative DNA damage. In conclusion, the consumption of Ginkgo biloba leaf extract for long periods at high doses/concentrations is potentially toxic; however, low doses protect the cells against basal oxidative damage and against environmentally derived toxicants that induce oxidative DNA damage. Full article

(This article belongs to the Special Issue Bioactive Compounds in Plants)

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20 pages, 2745 KiB

Open AccessArticle

Chemical and Antifungal Variability of Several Accessions of Azadirachta indica A. Juss. from Six Locations Across the Colombian Caribbean Coast: Identification of Antifungal Azadirone Limonoids

by Juan Manuel Álvarez-Caballero and Ericsson Coy-Barrera

Plants 2019, 8(12), 555; https://doi.org/10.3390/plants8120555 - 29 Nov 2019

Cited by 8 | Viewed by 3120

Abstract

Plant materials (i.e., leaves, fruits, and seeds) from 40 trees of Azadirachta indica A. Juss. were collected from six different locations across the Colombian Caribbean coast. Eighty-four ethanolic extracts were prepared and the total limonoid contents (TLiC) and the antifungal activity against Fusarium [...] Read more.

Plant materials (i.e., leaves, fruits, and seeds) from 40 trees of Azadirachta indica A. Juss. were collected from six different locations across the Colombian Caribbean coast. Eighty-four ethanolic extracts were prepared and the total limonoid contents (TLiC) and the antifungal activity against Fusarium oxysporum conidia were measured. Their chemical profiles were also recorded via liquid chromatography-electrospray ionization interface-mass spectrometry (LC-ESI-MS) analysis and the top-ranked features were then annotated after supervised multivariate statistics. Inter-location chemical variability within sample set was assessed by sparse partial least squares discriminant analysis (sPLS-DA) and the chemical profiles and biological activity datasets were integrated through single-Y orthogonal partial least squares (OPLS) to identify antifungal bioactives in test extracts. The TLiC and antifungal activity (IC₅₀ values) of the A. indica-derived extracts were found to be ranging from 4.5 to 48.5 mg limonin equivalent per g dry extract and 0.08–44.8 μg/mL, respectively. The presence/abundance of particular limonoids between collected samples influenced the variability among locations. In addition, the integration of chemical and antifungal activity datasets showed five features as markers probably contributing to the bioactivity, annotated as compounds with an azadirone-like moiety. To validate the information provided by the single-Y OPLS model, a high performance liquid chromatography (HPLC)-based microfractionation was then carried out on an active extract. The combined plot of chromatographic profile and microfraction bioactivity also evidenced five signals possessing the highest antifungal activity. The most active limonoid was identified as nimonol 1. Hence, this untargeted metabolite profiling was considered as a convenient tool for identifying metabolites as inter-location markers as well as antifungals against Fusarium oxysporum. Full article

(This article belongs to the Special Issue Bioactive Compounds in Plants)

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9 pages, 1375 KiB

Open AccessCommunication

Withaninsams A and B: Phenylpropanoid Esters from the Roots of Indian Ginseng (Withania somnifera)

by Su Cheol Baek, Seoyoung Lee, Sil Kim, Mun Seok Jo, Jae Sik Yu, Yoon-Joo Ko, Young-Chang Cho and Ki Hyun Kim

Plants 2019, 8(12), 527; https://doi.org/10.3390/plants8120527 - 20 Nov 2019

Cited by 13 | Viewed by 3832

Abstract

Withania somnifera (L.) Dunal (Solanaceae), known as Indian ginseng or ashwagandha, has been used in Indian Ayurveda for the treatment of a variety of disorders, such as diabetes and reproductive and nervous system disorders. It is particularly used as a general health tonic, [...] Read more.

Withania somnifera (L.) Dunal (Solanaceae), known as Indian ginseng or ashwagandha, has been used in Indian Ayurveda for the treatment of a variety of disorders, such as diabetes and reproductive and nervous system disorders. It is particularly used as a general health tonic, analgesic, and sedative. As part of continuing projects to discover unique bioactive natural products from medicinal plants, phytochemical investigation of the roots of W. somnifera combined with a liquid chromatography–mass spectrometry (LC/MS)-based analysis has led to the isolation of two novel phenylpropanoid esters, Withaninsams A (1) and B (2), as an inseparable mixture, along with three known phenolic compounds (3, 4, and 6) and a pyrazole alkaloid (5). The structures of the new compounds were elucidated using a combination of spectroscopic methods, including one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectroscopy (HR-ESIMS). Withaninsams A (1) and B (2) are phenylpropanoid esters that contain a side chain, 4-methyl-1,4-pentanediol unit. To the best of our knowledge, the present study is the first to report on phenylpropanoid esters with 4-methyl-1,4-pentanediol unit. The anti-inflammatory activity of the isolated compounds (1–6) was evaluated by determining their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages, where compound 3 inhibited LPS-induced NO production (IC₅₀ = 33.3 μM) and TNF-α production, a pro-inflammatory cytokine (IC₅₀ = 40.9 μM). The anti-inflammatory mechanism through the inhibition of transcriptional iNOS protein expression was confirmed by western blotting experiments for the active compound 3, which showed decreased iNOS protein expression. Full article

(This article belongs to the Special Issue Bioactive Compounds in Plants)

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14 pages, 14435 KiB

Open AccessArticle

Polyphenol Characterization and Skin-Preserving Properties of Hydroalcoholic Flower Extract from Himantoglossum robertianum (Orchidaceae)

by Miriam Bazzicalupo, Bruno Burlando, Marcella Denaro, Davide Barreca, Domenico Trombetta, Antonella Smeriglio and Laura Cornara

Plants 2019, 8(11), 502; https://doi.org/10.3390/plants8110502 - 14 Nov 2019

Cited by 24 | Viewed by 4455

Abstract

Himantoglossum robertianum (Loisel.) P. Delforge is a Mediterranean orchid whose propagation in vitro has been achieved, making it eligible as a source of bioactive substances. Flowers were analyzed by light and SEM microscopy and used to obtain a polyphenol-rich, hydroalcoholic flower extract (HFE). [...] Read more.

Himantoglossum robertianum (Loisel.) P. Delforge is a Mediterranean orchid whose propagation in vitro has been achieved, making it eligible as a source of bioactive substances. Flowers were analyzed by light and SEM microscopy and used to obtain a polyphenol-rich, hydroalcoholic flower extract (HFE). HFE was characterized for total phenols, flavonoids and proanthocyanidins, and for polyphenol profile by RP-LC-DAD. Antioxidant assays, in vitro collagenase and elastase inhibition, and MTT and cell motility assays on HaCaT keratinocytes were done. Microscopy showed epidermal cells containing anthocyanins in the flower labellum. Flavonoids (flavones and flavan-3-ols) represented the most abundant compounds (42.91%), followed by scopoletin (33.79%), and phenolic acids (23.3%). Antioxidant assays showed strong activities, rating ORAC > FRAP > TEAC > β-carotene bleaching > DPPH > iron-chelation. Biological assays showed elastase and collagenase inhibition (up to 42% and 78%, respectively), improvement of HaCaT cell viability after treatment with 500 μM H₂O₂ (from 30% to 84% of control), and stimulation of cell migration rate up to 210% of control. In summary, HFE counteracted different free radicals, while protective properties were shown by cell-free and cell-based bioassays, suggesting the possible use of H. robertianum flowers for skin-preserving, repair, and anti-aging applications. Full article

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14 pages, 2590 KiB

Open AccessArticle

Polyphenol Profile and Pharmaceutical Potential of Quercus spp. Bark Extracts

by Hosam O. Elansary, Agnieszka Szopa, Paweł Kubica, Halina Ekiert, Mohamed A. Mattar, Mohamed A. Al-Yafrasi, Diaa O. El-Ansary, Tarek K. Zin El-Abedin and Kowiyou Yessoufou

Plants 2019, 8(11), 486; https://doi.org/10.3390/plants8110486 - 9 Nov 2019

Cited by 58 | Viewed by 5570

Abstract

Targeted profiling of polyphenols in trees may reveal valuable sources of natural compounds with major applications in pharmacology and disease control. The current study targeted the profiling of polyphenols using HPLC-DAD in Quercus robur, Q. macrocarpa and Q. acutissima bark extracts. Free [...] Read more.

Targeted profiling of polyphenols in trees may reveal valuable sources of natural compounds with major applications in pharmacology and disease control. The current study targeted the profiling of polyphenols using HPLC-DAD in Quercus robur, Q. macrocarpa and Q. acutissima bark extracts. Free radical scavenging of each extract was investigated using antioxidant assays. Antimicrobial activities against a wide spectrum of bacteria and fungi were explored, as well as anticancer activities against different cancer cell lines. The HPLC-DAD analyses revealed the availability of several polyphenols in high amounts, including ellagic acid (in Q. robur) and caffeic acid (in Q. macrocarpa) in all three species. The bioactivity assay revealed high antioxidant activity in Q. robur compared to that of the other species, as well as phenolic standards. The three oak bark extracts showed clear antibacterial activities against most bacteria tested, with the highest antibacterial activities in the extracts of Q. robur. In addition, the three extracts showed higher antibacterial activities against Pseudomonas aeruginosa, Micrococcus flavus, and Escherichia coli compared to that of other bacteria. There were strong antifungal activities against some fungi, such as Aspergillus flavus, Penicillium funiculosum, and Penicillium ochrochloron. There were also noticeable anticancer activities against MCF-7, HeLa, Jurkat, and HT-29 cell lines, with the highest anticancer activity in the extracts of Q. robur. This is the first study that reveals not only novel sources of important polyphenols (e.g., ellagic acid) in Q. robur, Q. macrocarpa and Q. acutissima bark but also their anticancer activities against diverse cancer cell lines. Full article

(This article belongs to the Special Issue Bioactive Compounds in Plants)

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