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14 pages, 448 KiB  
Article
Comparison in Antioxidant Potential and Concentrations of Selected Bioactive Ingredients in Fruits of Lesser-Known Species
by Barbara Łata, Piotr Latocha, Radosław Łaźny and Anna Gutfeld
Foods 2024, 13(18), 2926; https://doi.org/10.3390/foods13182926 - 15 Sep 2024
Viewed by 672
Abstract
Fruits with a high content of biologically active compounds are essential in preventing many diseases. Therefore, the interest in searching for and testing new plant sources for bioactive constituents remains strong. Although many publications on individual species exist, their results are difficult to [...] Read more.
Fruits with a high content of biologically active compounds are essential in preventing many diseases. Therefore, the interest in searching for and testing new plant sources for bioactive constituents remains strong. Although many publications on individual species exist, their results are difficult to compare directly due to varying methods and conditions of analysis. Only a few studies have investigated many different species in a single analysis. Therefore, we examined and compared 21 different genotypes, using various measurement methods for total phenolic content (TPC) (Folin–Ciocalteu, FBBB), total antioxidant capacity (ABTS, FRAP, DPPH), and the HPLC technique for the total ascorbate concentration in freshly harvested fruits. One-way ANOVA, Principal Component Analysis, and Pearson Correlation were used to analyse and compare the results. The tested samples showed significant differences in TPC, ascorbate content, and antioxidant capacity. The correlation between the content of bioactive compounds and antioxidant capacity depended on the analytical methods, with results obtained using the FRAP test being the most strongly correlated. Due to higher levels of polyphenols, ascorbate, and antioxidant potential, the most promising species for further evaluation appear to be Chaenomeles × californica, Actinidia kolomikta, Mespilus germanica, and ×Sorboaronia fallax. Full article
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<p>PCA biplot (PC1 vs. PC2) for 21 cultivars examined and their chemical and antioxidant properties.</p>
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21 pages, 1205 KiB  
Article
Sea Buckthorn Leaves as a Potential Source of Antioxidant Substances
by Paulina Bośko, Wioletta Biel, Iryna Smetanska, Robert Witkowicz and Ewa Piątkowska
Appl. Sci. 2024, 14(12), 5038; https://doi.org/10.3390/app14125038 - 10 Jun 2024
Cited by 1 | Viewed by 1144
Abstract
Each year, agro-foods produce thousands of tonnes of by-products that contain high-value, unique nutrients. The application of plant by-products enables agro-food corporations to obtain value from them and avoid using natural resources. The idea of the bio economy protects against environmental pollution and [...] Read more.
Each year, agro-foods produce thousands of tonnes of by-products that contain high-value, unique nutrients. The application of plant by-products enables agro-food corporations to obtain value from them and avoid using natural resources. The idea of the bio economy protects against environmental pollution and leads to a cheap source of bioactive components, which can be transformed into value-added products for other industries. The numerous publications on the positive impact of sea buckthorn (SBT, Hippophae rhamnoides L., Elaeagnaceae family) and its products on human health mainly concern its fruits and seeds. However, there are few data relating to the properties of SBT leaves. The leaves of SBT can be a rich source of nutrients and biologically active substances. In this investigation, we report the study of the leaves of four SBT cultivars. We determined their antioxidant capacities, measured total polyphenols and total flavonoids, and quantified their major polyphenols and alkaloids. The results show that SBT leaves are a source of antioxidants and alkaloids. Additionally, in this raw material, we identified the presence of individual flavonols (rutoside and quercetin), individual anthocyanidins (cyaniding, delphinidin, and peonidin), and chelerythrine by high-performance thin-layer chromatography (HPTLC) for the first time. Through these types of studies, we aim to revalue this raw material, which is not well known in the world. Considering its nutritional properties, we seek to increase the use of its high-value, unique nutrients in food processing, medicine, and animal nutrition, in accordance with the goals of a closed-loop bioeconomy. Full article
(This article belongs to the Special Issue New Insights into Natural Antioxidants in Foods: 2nd Edition)
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<p>The map of the collection region and <span class="html-italic">Hippophae rhamnoides</span> L. leaves.</p>
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<p>The first two principal component axes for polyphenol content and antioxidant activity in SBT leaves for the variables (<b>A</b>) and for the scores (<b>B</b>), (ABTS—2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid; DPPH—1,1-diphenyl-2-picrylhydrazyl; PCL—photochemiluminescence assay; TP—Total Polyphenol; A—cv. Ascola; HA—cv. Habego; HE—cv. Hergo; L—cv. Leikora).</p>
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<p>The first two principal component axes for bioactive compound content in SBT leaves for variables (<b>A</b>) and for the scores (<b>B</b>), (C—Cyanidin; CHE—Chelerythrine; DE—Delphinidin; P—Peonidin; PAC—Proanthocyanidin; QE—Quercetin; R—Rutoside; TA—Total Anthocyanin; TF—Total Flavonoid; TFL—Total Flavonol; TT—Total Tannin; A—cv. Ascola; HA—cv. Habego; HE—cv. Hergo; L—cv. Leikora).</p>
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16 pages, 6849 KiB  
Article
Sea Buckthorn Flavonoid Extracted by High Hydrostatic Pressure Inhibited IgE-Stimulated Mast Cell Activation through the Mitogen-Activated Protein Kinase Signaling Pathway
by Zhuomin Yan, Xiaoping Feng, Xinian Li, Zhenpeng Gao, Zhouli Wang, Guangxu Ren and Fangyu Long
Foods 2024, 13(4), 560; https://doi.org/10.3390/foods13040560 - 12 Feb 2024
Cited by 2 | Viewed by 1654
Abstract
Sea buckthorn (Hippophaë rhamnoides L.), as one of the Elaeagnaceae family, has the significant function of anti-tumor, anti-inflammation, anti-oxidation, and other physiological activities. High hydrostatic pressure (HHP) extraction has the advantages of being easy and efficient, while maintaining biological activity. In this [...] Read more.
Sea buckthorn (Hippophaë rhamnoides L.), as one of the Elaeagnaceae family, has the significant function of anti-tumor, anti-inflammation, anti-oxidation, and other physiological activities. High hydrostatic pressure (HHP) extraction has the advantages of being easy and efficient, while maintaining biological activity. In this study, sea buckthorn flavonoid (SBF) was extracted with HHP and purified sea buckthorn flavonoid (PSBF) was isolated by AB-8 macroporous resin column. HPLC analysis was used to quantified them. In addition, the effect of anti-allergy in RBL-2H3 cells by SBF, PSBF, and their flavonoid compounds was evaluated. The results demonstrate the conditions for obtaining the maximum flavonoid amount of SBF: 415 MPa for 10 min, 72% ethanol concentration, and a liquid to solid ratio of 40 mL/g, which increased the purity from 1.46% to 13.26%. Both SBF and PSBF included rutin, quercitrin, quercetin, isorhamnetin, and kaempferol. In addition, quercitrin, kaempferol, and SBF could regulate Th1/Th2 cytokine balance. Moreover, extracellular Ca2+ influx was reduced by quercitrin and PSBF. Furthermore, rutin, quercetin, iso-rhamnetin, and SBF could also inhibit P-p38 and P-JNK expression, thereby suppressing the phosphorylation of the MAPK signaling pathways. Overall, SBF is effective for relieving food allergy and might be a promising anti-allergic therapeutic agent. Full article
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<p>Effect of pressure (<b>A</b>), pressure−holding time (<b>B</b>), ethanol concentration (<b>C</b>), ratio of liquid−to−solid (<b>D</b>) on high hydrostatics pressure extraction (HHP) amount of flavonoid from sea buckthorn. Different letters represent significant differences (<span class="html-italic">p</span> &lt; 0.05).</p>
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<p>The plots for 3D response surface reveal the effect of (<b>A</b>) pressure and pressure-holding time; (<b>B</b>) pressure and ethanol concentration; (<b>C</b>) pressure-holding time and ratio of liquid-to-solid; (<b>D</b>) pressure-holding time and ethanol concentration; (<b>E</b>) pressure and ratio of liquid-to-solid; (<b>F</b>) ethanol concentration and ratio of liquid-to-solid on the extraction amount of flavonoid.</p>
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<p>The chemical structures of flavonoids components and HPLC chromatogram of SBF (<b>A</b>) and PSBF (<b>B</b>) obtained by HHP under optimum conditions (415 MPa, ethanol concentration 72%, liquid-to-solid ratio 40 mL/g, time 10 min, and temperature 20 °C). Peaks 1, 2, 3, 4, and 5 represent rutin, quercitrin, quercetin, kaempferol, and isorhamnetin, respectively.</p>
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<p>Effect of SBF, PSBF, and five compounds on β-hexosaminidase and histamine release in RBL-2H3 cells. The positive control is ketotifen fumarate at 100 μmol/L. The β-hexosaminidase (<b>A</b>–<b>E</b>) and histamine (<b>G</b>–<b>K</b>) release in RBL-2H3 cells treated with 10, 20, and 40 μmol/L of rutin, quercitrin, quercetin, isorhamnetin, and kaempferol. The β-hexosaminidase (<b>F</b>) and histamine (<b>L</b>) release in RBL-2H3 cells treated with 25, 50, and 100 μg/mL of SBF and PSBF. Results are expressed as the mean ± SD of three independent experiments. * <span class="html-italic">p</span> &lt; 0.05 and ** <span class="html-italic">p</span> &lt; 0.01, in comparison with allergy model group; ## <span class="html-italic">p</span> &lt; 0.01 in comparison with the control group.</p>
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<p>Effects of SBF, PSBF, and five compounds on the morphology of RBL-2H3 cells degranulation under an inverted microscope. (<b>A</b>) Control; (<b>B</b>) allergy model; (<b>C</b>) positive control; (<b>D</b>) 40 μmol/L of quercitrin; (<b>E</b>) 100 μg/mL of SBF; (<b>F</b>) 25 μg/mL of PSBF.</p>
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<p>Effect of SBF, PSBF, and five compounds on IL-4, IFN-<span class="html-italic">γ</span> release, and Th1/Th2 balance in RBL-2H3 cells. The positive control is ketotifen fumarate at 100 μmol/L. The IL-4 (<b>A</b>–<b>E</b>) and IFN-<span class="html-italic">γ</span> (<b>G</b>–<b>K</b>) release in RBL-2H3 cells treated with 10, 20, and 40 μmol/L of rutin, quercitrin, quercetin, isorhamnetin, and kaempferol. The IL-4 (<b>F</b>) and histamine (<b>L</b>) IFN-<span class="html-italic">γ</span> in RBL-2H3 cells treated with 25, 50, and 100 μg/mL of SBF and PSBF. The ratio of IL-4 and IFN-<span class="html-italic">γ</span> (<b>M</b>) in RBL-2H3 cells treated with 40 μmol/L of quercitrin and 100 μg/mL of SBF. Results are expressed as the mean ± SD of three independent experiments. (## <span class="html-italic">p</span> &lt; 0.01, * <span class="html-italic">p</span> &lt; 0.05, and ** <span class="html-italic">p</span> &lt; 0.01).</p>
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<p>Effect of SBF, PSBF cellular Ca<sup>2+</sup> in RBL-2H3 cell. (<b>A</b>) Rutin; (<b>B</b>) quercitrin; (<b>C</b>) quercetin; (<b>D</b>) isorhamnetin; (<b>E</b>) kaempferol; (<b>F</b>) SBF; (<b>G</b>) PSBF. Effect of five compounds (<b>H</b>–<b>L</b>) and SBF, PSBF (<b>M</b>) on average intracellular Ca<sup>2+</sup> in RBL-2H3 cells. The positive control is ketotifen fumarate at 100 μmol/L. Results are expressed as the mean ± SD of three independent experiments. (## <span class="html-italic">p</span> &lt; 0.01, * <span class="html-italic">p</span> &lt; 0.05 and ** <span class="html-italic">p</span> &lt; 0.01).</p>
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<p>Effect of SBF, PSBF, and quercetin on intracellular Ca<sup>2+</sup> in RBL-2H3 cells was observed on an inverted fluorescence microscope. The positive control is ketotifen fumarate at 100 μmol/L. (<b>A</b>) Control; (<b>B</b>) allergy model; (<b>C</b>) positive control; (<b>D</b>) 40 μmol/L of quercetin; (<b>E</b>) 100 μg/mL of SBF; (<b>F</b>) 100 μg/mL of PSBF.</p>
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<p>Effect of SBF, PSBF, and five compounds on MAPK signaling in RBL-2H3 cells. The positive control is ketotifen fumarate. (<b>A</b>) p38, ERK, JNK, and phosphorylation of p38, ERK, JNK were determined with Western blot. Number 1 represents ketotifen fumarate at 100 μmol/L, and 2, 3 represent SBF and PSBF at 100 μg/mL. Number 4, 5, 6, 7, and 8 represent rutin, quercitrin, quercetin, isorhamnetin, and kaempferol at 40 μmol/L, respectively. (<b>B</b>) Densitometric analysis. Results are expressed as the mean ± SD of three independent experiments. * <span class="html-italic">p</span> &lt; 0.05 and ** <span class="html-italic">p</span> &lt; 0.01, in comparison with allergy model group; # <span class="html-italic">p</span> &lt; 0.05, ## <span class="html-italic">p</span> &lt; 0.01 in comparison with the control group.</p>
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16 pages, 2632 KiB  
Article
Chemical Constituents with Anti-Lipid Droplet Accumulation and Anti-Inflammatory Activity from Elaeagnus glabra
by Ju-Hsin Cheng, Ho-Cheng Wu, Chia-Hung Yen, Tsong-Long Hwang, Horng-Huey Ko and Hsun-Shuo Chang
Plants 2023, 12(16), 2943; https://doi.org/10.3390/plants12162943 - 14 Aug 2023
Cited by 1 | Viewed by 1519
Abstract
Non-alcoholic fatty liver disease (NAFLD) is a type of steatosis caused by excess lipids accumulating in the liver. The prevalence of NAFLD has increased annually due to modern lifestyles and a lack of adequate medical treatment. Thus, we were motivated to investigate the [...] Read more.
Non-alcoholic fatty liver disease (NAFLD) is a type of steatosis caused by excess lipids accumulating in the liver. The prevalence of NAFLD has increased annually due to modern lifestyles and a lack of adequate medical treatment. Thus, we were motivated to investigate the bioactive components of Formosan plants that could attenuate lipid droplet (LD) accumulation. In a series of screenings of 3000 methanolic extracts from the Formosan plant extract bank for anti-LD accumulation activity, the methanolic extract of aerial parts of Elaeagnus glabra Thunb. showed excellent anti-LD accumulation activity. E. glabra is an evergreen shrub on which only a few phytochemical and biological studies have been conducted. Here, one new flavonoid (1), two new triterpenoids (2 and 3), and 35 known compounds (438) were isolated from the ethyl acetate layer of aerial parts of E. glabra via a bioassay-guided fractionation process. Their structures were characterized by 1D and 2D NMR, UV, IR, and MS data. Among the isolated compounds, methyl pheophorbide a (37) efficiently reduced the normalized LD content to 0.3% with a concentration of 20 μM in AML12 cell lines without significant cytotoxic effects. 3-O-(E)-Caffeoyloleanolic acid (13) and methyl pheophorbide a (37) showed inhibitory effects on superoxide anion generation or elastase release in fMLP/CB-treated human neutrophils (IC50 < 3.0 μM); they displayed effects similar to those of the positive control, namely, LY294002. These findings indicate that E. glabra can be used for developing a new botanical drug for managing LD accumulation and against inflammation-related diseases. Full article
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<p>Use of the high-throughput screening platform for anti-LD candidate discovery from the Formosan methanolic extract bank and the results.</p>
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<p>Structures of compounds <b>1</b>−<b>3</b>.</p>
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<p>Key HMBC and COSY correlations of compounds <b>1</b>−<b>3</b>.</p>
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<p>Key NOESY correlations of compounds <b>2</b> and <b>3</b>.</p>
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<p>Effect of methyl pheophorbide a (<b>37</b>) on LD accumulation. (<b>A</b>) Representative images of the anti-LD formation activity of methyl pheophorbide a (<b>37</b>). (<b>B</b>) Quantification results of the LD assay and cell viability. AML12 cells were treated with BSA or OA (125 µM) with 20 µM methyl pheophorbide a (<b>37</b>) for 24 h. AML12 cells were used as a cell model for lipid accumulation—they were treated with 125 μM oleic acid (OA) for 24 h. Nuclei and LD were stained with Hoechst 33342 (blue) and BODIPY<sup>®</sup> 493/503 (green), respectively. The asterisk indicates a significant difference from the solvent control cells (*** <span class="html-italic">p</span> &lt; 0.001, one-way ANOVA).</p>
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<p>Preliminary screening of the inhibitory activities toward superoxide anion and elastase release of isolates from aerial parts of <span class="html-italic">E. glabra</span>. Percentage of inhibition (Inh%) at 10 μM. The results are presented as the mean ± S.E.M. (<span class="html-italic">n</span> = 3–5). * <span class="html-italic">p</span> &lt; 0.05, ** <span class="html-italic">p</span> &lt; 0.01, and *** <span class="html-italic">p</span> &lt; 0.001 compared with the control (DMSO).</p>
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11 pages, 1657 KiB  
Article
The Chromosome-Level Genome of Elaeagnus moorcroftii Wall., an Economically and Ecologically Important Tree Species in Drylands
by Xinxing Fu, Jingjing Wu, Xiaohui Ma, Kunpeng Li, Hui Zhang, Shengdan Wu and Kun Sun
Diversity 2022, 14(6), 468; https://doi.org/10.3390/d14060468 - 11 Jun 2022
Cited by 7 | Viewed by 3130
Abstract
Elaeagnus moorcroftii Wall. (Elaeagnaceae) is an important tree species naturally growing in arid Northwest China that has great economic and ecological values in drylands. In this study, we de novo assembled a chromosome-level genome for E. moorcroftii by using PacBio’s high-fidelity (HiFi) sequencing [...] Read more.
Elaeagnus moorcroftii Wall. (Elaeagnaceae) is an important tree species naturally growing in arid Northwest China that has great economic and ecological values in drylands. In this study, we de novo assembled a chromosome-level genome for E. moorcroftii by using PacBio’s high-fidelity (HiFi) sequencing and Hi-C-assisted assembly technology. The assembled genome size was 529.56 Mb, of which 94.56% was anchored to 14 pseudochromosomes with a contig N50 up to 28.21 Mb. In total, 29,243 protein-coding genes were annotated, and 98.5% of the Benchmarking Universal Single-Copy Orthologs (BUSCOs) were captured in the genome. Evolutionary genomic analysis showed that E. moorcroftii split with Elaeagnus mollis 9.38 million years ago (Ma), and contrasted evolutionary trajectories of gene family expansion and contraction were observed for these two closely related species. Furthermore, we identified two successive whole genome duplication (WGD) events occurred in the genome of E. moorcroftii, in addition to the ancient gamma hexaploidization event shared by core eudicots. Together, the chromosome-level genome assembly for E. moorcroftii decoded here provides valuable genomic information for the further genetic improvement and molecular breeding of this indigenous species in drylands. Full article
(This article belongs to the Special Issue Ecology, Evolution and Diversity of Plants)
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<p>The genome features of <span class="html-italic">E. moorcroftii</span>. (<b>a</b>) Heatmap of Hi-C interactions for 14 pseudochromosomes. (<b>b</b>) Circos plot showing the genomic landscape of <span class="html-italic">E. moorcroftii</span>. The tracks from outer to inner circles indicate the following: a: 4 pseudochromosomes in megabases; b: GC content; c: gene density; d: density of <span class="html-italic">Gypsy</span> LTR retrotransposons; e: density of <span class="html-italic">Copia</span> LTR retrotransposons; f: LTR retrotransposons density. The center of the circos plot shows the fruits of <span class="html-italic">E. moorcroftii</span> (photo by X.F.).</p>
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<p>Comparative and evolutionary genomic analysis of <span class="html-italic">E. moorcroftii</span> and 10 other plant species. A phylogenetic tree among 11 species was reconstructed based on 175 single-copy genes, and their divergence times were also estimated. The numbers of expansion (blue) and contraction (red) gene families are shown above the branches.</p>
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<p>Integrating <span class="html-italic">K</span>s and synteny analyses reveal two successive WGD events in <span class="html-italic">E. moorcroftii</span>. (<b>a</b>) The distributions of <span class="html-italic">K</span><sub>S</sub> of paralogous gene pairs of <span class="html-italic">E. mollis</span> (pink line), <span class="html-italic">E. moorcroftii</span> (green line), <span class="html-italic">H. rhamnoides</span> (blue line), and <span class="html-italic">V. vinifera</span> (purple line). The dashed lines represent <span class="html-italic">K</span><sub>S</sub> distributions related to the species divergence of the corresponding species pairs. (<b>b</b>) Macro-syntenic comparisons among three Elaeagnaceae species and <span class="html-italic">V. vinifera</span>.</p>
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10 pages, 924 KiB  
Technical Note
The Development of New Species-Specific Molecular Markers Based on 5S rDNA in Elaeagnus L. Species
by Oleg S. Alexandrov and Gennady I. Karlov
Plants 2021, 10(12), 2713; https://doi.org/10.3390/plants10122713 - 10 Dec 2021
Cited by 3 | Viewed by 2684
Abstract
The Elaeagnus L. species are trees and bushes that mainly grow in temperate zones of Western Europe; Minor, Central, and Southeast Asia; the Far East; and North America. Some species are used as fruit or ornamental plants and have economic value. Problems with [...] Read more.
The Elaeagnus L. species are trees and bushes that mainly grow in temperate zones of Western Europe; Minor, Central, and Southeast Asia; the Far East; and North America. Some species are used as fruit or ornamental plants and have economic value. Problems with the identification of species in the Elaeagnus genus by molecular genetical methods arise in the study of populations, systematics, breeding, and other areas of plant science and practice. Recently, the polymorphism of 5S ribosomal DNA non-transcribed spacers (5S rDNA NTSs) in Elaeagnaceae Adans. has been described. The results were used in our study as a basis for development of new species-specific molecular markers for some members of the Elaeagnus genus. The author’s method was applied for finding regions that were potentially applicable for species-specific primer design. As a result, some species-specific molecular markers were developed for Elaeagnus angustifolia L., E. commutata Bernh., E. pungens Thunb., and E. multiflora Thunb. These markers were tested in a range of samples and showed the presence of amplified fragments in lanes of the marked species only. Samples of other species showed no amplifications. Thus, the developed markers may be useful for the species identification of the studied Elaeagnus plants in botanical, dendrological, and genetic research (especially in a leafless period of year), as well as in breeding and hybridization experiments. Full article
(This article belongs to the Special Issue Plant Molecular Breeding)
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<p>Detection of PCR products by electrophoresis (<b>A</b>) with Elang1-f/Elang1-r primers, (<b>B</b>) with Elcom1-f/Elcom1-r primers, (<b>C</b>) with Elpung1-f/Elpung1-r primers, and (<b>D</b>) with Elmult1-f/Elmult2-r primers. Numbers of lanes correspond to numbers of samples in <a href="#app1-plants-10-02713" class="html-app">Supplementary Materials</a> <a href="#app1-plants-10-02713" class="html-app">Table S13</a>. M, marker of molecular weight with 100 bp stepFinally, different combinations of Elmult1-f and Elmult2-f, as well as Elmult1-r, Elmult2-r, and Elmult3-r, were tested by using a PCR experiment (the tests were carried out among a limited number of samples selected according to the principle “one species–one sample” for <span class="html-italic">Elaeagnus</span> spp. and <span class="html-italic">H. rhamnoides</span> as a control). The Elmult1-f/Emult3-r pair did not show the amplified fragments in all samples and was dismissed as a very unfortunate pair (<a href="#app1-plants-10-02713" class="html-app">Figure S1</a>). All remaining pairs showed target amplification in the <span class="html-italic">E. multiflora</span> and <span class="html-italic">E. umbellata</span> samples (the NTSs of these species look similar to NTSs of one species). However, the Emult2-f/Emult1-r and Emult2-f/Emult2-r pairs also demonstrated the amplified fragments in <span class="html-italic">E. pungens</span> sample. Thus, the best pairs were Elmult1-f/Elmult1-r, Elmult1-f/Elmult2-r, and Elmult2-f/Elmult3-r, because they did not have a non-specific amplification in any other <span class="html-italic">Elaeagnus</span> species and <span class="html-italic">H. rhamnoides</span>. The amplifications with the Elmult1-f/Elmult2-r pair were the brightest among all <span class="html-italic">E. multiflora</span> primer combinations (<a href="#app1-plants-10-02713" class="html-app">Figure S1</a>). It is likely that the PCR conditions for this pair turned out to be the most optimal. This pair should be recommended first. It was used to check all Elaeagnaceae samples collected for this study (<a href="#plants-10-02713-f001" class="html-fig">Figure 1</a>D).</p>
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11 pages, 3681 KiB  
Communication
Phytochemical Analysis of the Fruits of Sea Buckthorn (Hippophae rhamnoides): Identification of Organic Acid Derivatives
by Yong Hoon Lee, Hee Joo Jang, Kun Hee Park, Seon-Hee Kim, Jung Kyu Kim, Jin-Chul Kim, Tae Su Jang and Ki Hyun Kim
Plants 2021, 10(5), 860; https://doi.org/10.3390/plants10050860 - 24 Apr 2021
Cited by 14 | Viewed by 3228
Abstract
Hippophae rhamnoides L. (Elaeagnaceae), commonly known as “Sea buckthorn” and “Vitamin tree”, is a spiny deciduous shrub whose fruit is known for its nutritional composition, such as vitamin C, and is consumed as a dietary supplement worldwide. As part of our ongoing efforts [...] Read more.
Hippophae rhamnoides L. (Elaeagnaceae), commonly known as “Sea buckthorn” and “Vitamin tree”, is a spiny deciduous shrub whose fruit is known for its nutritional composition, such as vitamin C, and is consumed as a dietary supplement worldwide. As part of our ongoing efforts to identify structurally new and bioactive constituents from natural resources, the phytochemical investigation of the extract of H. rhamnoides fruits led to the isolation of one malate derivative (1), five citrate derivatives (2–6), and one quinate derivative (7). The structures of the isolated compounds were elucidated by analysis of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data and high-resolution electrospray ionization (HR-ESI) liquid chromatography–mass spectrometry (LC/MS) data. Three of the citrate derivatives were identified as new compounds: (S)-1-butyl-5-methyl citrate (3), (S)-1-butyl-1′-methyl citrate (4), and (S)-1-methyl-1′-butyl citrate (6), which turned out to be isolation artifacts. The absolute configurations of the new compounds were established by quantum chemical electronic circular dichroism (ECD) calculation, which is an informative tool for verifying the absolute configuration of organic acid derivatives. The isolated compounds 1–7 were evaluated for their stimulatory effects on osteogenesis. Compounds 1, 3, 4, 6, and 7 stimulated osteogenic differentiation up to 1.4 fold, compared to the negative control. These findings provide experimental evidence that active compounds 1, 3, 4, 6, and 7 induce the osteogenesis of mesenchymal stem cells and activate bone formation. Full article
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<p>Chemical structure of compounds <b>1–7</b>.</p>
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<p>Key <sup>1</sup>H-<sup>1</sup>H COSY (<span class="html-fig-inline" id="plants-10-00860-i001"> <img alt="Plants 10 00860 i001" src="/plants/plants-10-00860/article_deploy/html/images/plants-10-00860-i001.png"/></span>) and HMBC (<span class="html-fig-inline" id="plants-10-00860-i002"> <img alt="Plants 10 00860 i002" src="/plants/plants-10-00860/article_deploy/html/images/plants-10-00860-i002.png"/></span>) correlations of compounds <b>3</b>, <b>4</b>, and <b>6</b>.</p>
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<p>Experimental and calculated ECD spectra of <b>3</b>.</p>
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<p>Experimental and calculated ECD spectra of <b>4</b>.</p>
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<p>Experimental and calculated ECD spectra of <b>6</b>.</p>
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<p>The effects of compounds <b>1–7</b> on the differentiation of mesenchymal stem cells (MSCs) toward osteoblasts. (<b>A</b>) Stimulatory effect of compounds <b>1–7</b> on osteogenic differentiation of MSC. Fully-differentiated C3H10T1/2 cells were stained with alkaline phosphatase (ALP) at 9 d after osteogenic differentiation with 20 µM of compounds <b>1–7</b>. (<b>B</b>) ALP enzyme activity was measured in osteogenically differentiated C3H10T1/2 cells treated with compounds <b>1–7</b>. The values were calculated relatively by setting the untreated negative control to 1. Oryzativol A (5 μM) was added to the experimental set as a positive control and marked as OryA. * denotes <span class="html-italic">p</span> &lt; 0.05 and *** denotes <span class="html-italic">p</span> &lt; 0.001.</p>
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11 pages, 778 KiB  
Article
A Comparative Study of 5S rDNA Non-Transcribed Spacers in Elaeagnaceae Species
by Oleg S. Alexandrov, Olga V. Razumova and Gennady I. Karlov
Plants 2021, 10(1), 4; https://doi.org/10.3390/plants10010004 - 23 Dec 2020
Cited by 6 | Viewed by 2129
Abstract
5S rDNA is organized as a cluster of tandemly repeated monomers that consist of the conservative 120 bp coding part and non-transcribed spacers (NTSs) with different lengths and sequences among different species. The polymorphism in the 5S rDNA NTSs of closely related species [...] Read more.
5S rDNA is organized as a cluster of tandemly repeated monomers that consist of the conservative 120 bp coding part and non-transcribed spacers (NTSs) with different lengths and sequences among different species. The polymorphism in the 5S rDNA NTSs of closely related species is interesting for phylogenetic and evolutional investigations, as well as for the development of molecular markers. In this study, the 5S rDNA NTSs were amplified with universal 5S1/5S2 primers in some species of the Elaeagnaceae Adans. family. The polymerase chain reaction (PCR) products of five Elaeagnus species had similar lengths near 310 bp and were different from Shepherdia canadensis (L.) Nutt. and Sh. argentea (Pusch.) Nutt. samples (260 bp and 215 bp, respectively). The PCR products were cloned and sequenced. An analysis of the sequences revealed that intraspecific levels of NTS identity are high (approximately 95–96%) and similar in the Elaeagnus L. species. In Sh. argentea, this level was slightly lower due to the differences in the poly-T region. Moreover, the intergeneric and intervarietal NTS identity levels were studied and compared. Significant differences between species (except E. multiflora Thunb. and E. umbellata Thunb.) and genera were found. Herein, a range of the NTS features is discussed. This study is another step in the investigation of the molecular evolution of Elaeagnaceae and may be useful for the development of species-specific DNA markers in this family. Full article
(This article belongs to the Section Plant Genetics, Genomics and Biotechnology)
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<p>The results of the polymerase chain reaction (PCR) experiments with 5S1/5S2 in the <span class="html-italic">Elaeagnus</span> and <span class="html-italic">Shepherdia</span> species. The lines correspond to the samples in the follow order: (1) <span class="html-italic">E. angustifolia</span>, (2) <span class="html-italic">E. commutata</span>, (3) <span class="html-italic">E. multiflora</span>, (4) <span class="html-italic">E. pungens</span>, (5) <span class="html-italic">E. umbellata</span>, (6) <span class="html-italic">Sh. canadensis</span>, and (7) <span class="html-italic">Sh. argentea</span>. The molecular weight marker is 100 bp.</p>
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<p>The alignment of <span class="html-italic">Shepherdia argentea</span> (<b>a</b>) and <span class="html-italic">Sh. canadensis</span> (<b>b</b>) non-transcribed spacers (NTSs). The poly-T regions are indicated by red. The poly-A region is indicated by pink. The TATA-like motifs are indicated by green.</p>
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<p>The alignment of the <span class="html-italic">Elaeagnus angustifolia</span> (<b>a</b>), <span class="html-italic">E. commutata</span> (<b>b</b>), <span class="html-italic">E. multiflora</span> (<b>c</b>), <span class="html-italic">E. pungens</span> (<b>d</b>), <span class="html-italic">E. umbellata</span> var. ‘‘Fortunella’’ (<b>e</b>), <span class="html-italic">E. umbellata</span> var. ‘‘Brilliant Rose’’ (<b>f</b>), <span class="html-italic">E. umbellata</span> without variety (<b>g</b>), and <span class="html-italic">E. umbellata</span> var. ‘‘Sweet’n’Sour’’ (<b>h</b>) NTSs. The poly-T regions are indicated by red. The poly-A region is indicated by pink. The TATA-like motifs are indicated by green.</p>
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15 pages, 4796 KiB  
Article
Catechol-Type Flavonoids from the Branches of Elaeagnus glabra f. oxyphylla Exert Antioxidant Activity and an Inhibitory Effect on Amyloid-β Aggregation
by Yu Jin Kim, Eunjin Sohn, Joo-Hwan Kim, MinKyun Na and Soo-Jin Jeong
Molecules 2020, 25(21), 4917; https://doi.org/10.3390/molecules25214917 - 23 Oct 2020
Cited by 17 | Viewed by 2581
Abstract
Elaeagnus glabra f. oxyphylla (Elaeagnaceae) is a small evergreen tree with narrow lanceolate leaves that is native to Korea. In this work, we studied the chemical composition of E. glabra f. oxyphylla branches (EGFOB) for the first time. Additionally, we evaluated the effects [...] Read more.
Elaeagnus glabra f. oxyphylla (Elaeagnaceae) is a small evergreen tree with narrow lanceolate leaves that is native to Korea. In this work, we studied the chemical composition of E. glabra f. oxyphylla branches (EGFOB) for the first time. Additionally, we evaluated the effects of the ethanol extract of EGFOB and each of its chemical components on key mediators of Alzheimer’s disease (AD), namely, amyloid-β (Aβ) aggregation and oxidative stress. The ethanol extract of EGFOB decreased Aβ aggregation (IC50 = 32.01 µg/mL) and the levels of the oxidative free radicals 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) (IC50 = 11.35 and 12.32 µg/mL, respectively). Sixteen compounds were isolated from EGFOB. Among them, procyanidin B3 (8), procyanidin B4 (9), and helichrysoside (13) significantly inhibited Aβ aggregation (IC50 = 14.59, 32.64, and 44.45 μM, respectively), indicating their potential as bioactive compounds to control Aβ aggregation. Furthermore, these compounds markedly enhanced in vitro scavenging activity against ABTS (IC50 = 3.21–4.61 µM). In the DPPH test, they showed lower scavenging activity than in the ABTS test (IC50 ≥ 54.88 µM). Thus, these results suggest that EGFOB and specifically compounds 8, 9, and 13 may be beneficial in AD prevention and treatment through their antioxidant and anti-Aβ aggregation activities. Full article
(This article belongs to the Section Natural Products Chemistry)
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<p>Inhibitory effects of <span class="html-italic">E. glabra</span> f. <span class="html-italic">oxyphylla</span> branches (EGFOB) and leaves (EGFOL) extracts on amyloid-β (Aβ) aggregation. Various concentrations (6.25, 12.5, 25, 50, or 100 μg/mL) of (<b>A</b>) EGFOB and (<b>B</b>) EGFOL were prepared and reacted with Aβ<sub>1–42</sub> peptides, followed by the addition of Thioflavin (ThT). Fluorescence intensity was measured at 440 nm (excitation) and 485 nm (emission). Each value is expressed as the mean ± SEM (<span class="html-italic">n</span> = 3). <sup>*</sup><span class="html-italic">p</span> &lt; 0.05, <sup>**</sup><span class="html-italic">p</span> &lt; 0.01, or <sup>***</sup><span class="html-italic">p</span> &lt; 0.001 vs. control.</p>
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<p>Antioxidant effects of <span class="html-italic">E. glabra</span> f. <span class="html-italic">oxyphylla</span> branches (EGFOB) and leaves (EGFOL). Antioxidant activity was measured by free radical scavenging assay for 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) (<b>A</b>,<b>B</b>) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) (<b>C</b>,<b>D</b>). Each value is presented as the mean ± SEM (<span class="html-italic">n</span> = 3). Ascorbic acid (AA) was used as a positive control. <sup>**</sup><span class="html-italic">p</span> &lt; 0.01 or <sup>***</sup><span class="html-italic">p</span> &lt; 0.001 vs. control.</p>
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<p>Extraction and fractionation of <span class="html-italic">E. glabra</span> f. <span class="html-italic">oxyphylla</span> branches (EGFOB).</p>
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<p>Inhibitory effects of solvent fractions of EGFOB on amyloid-β (Aβ) aggregation. Various concentrations (6.25, 12.5, 25, 50, or 100 μg/mL) of (<b>A</b>) <span class="html-italic">n</span>-hexane, (<b>B</b>) EtOAc, (<b>C</b>) <span class="html-italic">n</span>-BuOH, and (<b>D</b>) water fractions were prepared and reacted with Aβ<sub>1–42</sub> peptides, followed by the addition of ThT. Fluorescence intensity was measured at 440 nm (excitation) and 485 nm (emission). Each value is expressed as the mean ± SEM (<span class="html-italic">n</span> = 3). <sup>*</sup><span class="html-italic">p</span> &lt; 0.05, <sup>**</sup><span class="html-italic">p</span> &lt; 0.01, or <sup>***</sup><span class="html-italic">p</span> &lt; 0.001 vs. control.</p>
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<p>Structures of compounds <b>1</b>–<b>16</b> constituting EGFOB. 4-hydroxybenzoic acid (<b>1</b>), salicylic acid (<b>2</b>), vanillic acid (<b>3</b>), (+)-catechin (<b>4</b>), (–)-epicatechin (<b>5</b>), (+)-gallocatechin (<b>6</b>), (–)-epigallocatechin (<b>7</b>), procyanidin B3 (<b>8</b>), procyanidin B4 (<b>9</b>), kaempferol (<b>10</b>), astragalin (<b>11</b>), <span class="html-italic">trans</span>-tiliroside (<b>12</b>), helichrysoside (<b>13</b>), betulinic acid-3-<span class="html-italic">O</span>-<span class="html-italic">trans</span>-caffeate (<b>14</b>), ursolic acid-3-<span class="html-italic">O</span>-<span class="html-italic">trans</span>-caffeate (<b>15</b>), and 1-mono(22-<span class="html-italic">O</span>-feruloyl-oxydocosanoyl)glycerol (<b>16</b>).</p>
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<p>HPLC chromatograms of the ethanol extract of (<b>A</b>) EGFOB and (<b>B</b>) isolated compound mixture at 240 nm.</p>
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<p>Inhibitory effects of compounds <b>1</b>–<b>16</b> from EGFOB on amyloid-β (Aβ) aggregation. Compounds <b>1</b>–<b>16</b> (100 μM) isolated from EGFOB (<b>A</b>) and various concentrations (6.25, 12.5, 25, 50, or 100 μM) of procyanidin B3 (<b>8</b>) (<b>B</b>), procyanidin B4 (<b>9</b>) (<b>C</b>), and helichrysoside (<b>13</b>) (<b>D</b>) were reacted with Aβ<sub>1–42</sub> peptides, followed by the addition of ThT. Fluorescence was measured at 440 nm (excitation) and 485 nm (emission). Morin (100 μM) was used as a positive control. Each value is shown as the mean ± SEM (<span class="html-italic">n</span> = 3). <sup>*</sup><span class="html-italic">p</span> &lt; 0.05, <sup>**</sup><span class="html-italic">p</span> &lt; 0.01, or <sup>***</sup><span class="html-italic">p</span> &lt; 0.001 vs. control.</p>
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<p>Antioxidant effects of compounds <b>1</b>–<b>16</b> from EGFOB. Antioxidant activities of compounds <b>1</b>–<b>16</b> (100 μM) (<b>A</b>,<b>B</b>), procyanidin B3 (<b>8</b>) (<b>C</b>), procyanidin B4 (<b>9</b>) (<b>D</b>), and helichrysoside (<b>13</b>) (<b>E</b>) (1.5625–100 μM) were measured using ABTS and DPPH radical scavenging assays. Ascorbic acid (AA) (50 μM) was used as a positive control. Each value is presented as the mean ± SEM (<span class="html-italic">n</span> = 3). <sup>*</sup><span class="html-italic">p</span> &lt; 0.05, <sup>***</sup><span class="html-italic">p</span> &lt; 0.001, or <sup>****</sup><span class="html-italic">p</span> &lt; 0.0001 vs. control.</p>
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12 pages, 2368 KiB  
Communication
Inhibitory Effect of 1,5-Dimethyl Citrate from Sea Buckthorn (Hippophae rhamnoides) on Lipopolysaccharide-Induced Inflammatory Response in RAW 264.7 Mouse Macrophages
by Su Cheol Baek, Dahae Lee, Mun Seok Jo, Kwang Ho Lee, Yong Hoon Lee, Ki Sung Kang, Noriko Yamabe and Ki Hyun Kim
Foods 2020, 9(3), 269; https://doi.org/10.3390/foods9030269 - 2 Mar 2020
Cited by 13 | Viewed by 3914
Abstract
Hippophae rhamnoides L. (Elaeagnaceae; commonly known as “sea buckthorn” and “vitamin tree”), is a spiny deciduous shrub whose fruit is used in foods and traditional medicines. The H. rhamnoides fruit (berry) is rich in vitamin C, with a level exceeding that found in [...] Read more.
Hippophae rhamnoides L. (Elaeagnaceae; commonly known as “sea buckthorn” and “vitamin tree”), is a spiny deciduous shrub whose fruit is used in foods and traditional medicines. The H. rhamnoides fruit (berry) is rich in vitamin C, with a level exceeding that found in lemons and oranges. H. rhamnoides berries are usually washed and pressed to create pomace and juice. Today, the powder of the aqueous extract of H. rhamnoides berries are sold as a functional food in many countries. As part of our ongoing effort to identify bioactive constituents from natural resources, we aimed to isolate and identify those from the fruits of H. rhamnoides. Phytochemical analysis of the extract of H. rhamnoides fruits led to the isolation and identification of six compounds, namely, a citric acid derivative (1), a phenolic (2), flavonoids (3 and 4), and megastigmane compounds (5 and 6). Treatment with compounds 16 did not have any impact on the cell viability of RAW 264.7 mouse macrophages. However, pretreatment with these compounds suppressed lipopolysaccharide (LPS)-induced NO production in RAW 264.7 mouse macrophages in a concentration-dependent manner. Among the isolated compounds, compound 1 was identified as the most active, with an IC50 of 39.76 ± 0.16 μM. This value was comparable to that of the NG-methyl-L-arginine acetate salt, a nitric oxide synthase inhibitor with an IC50 of 28.48 ± 0.05 μM. Western blot analysis demonstrated that compound 1 inhibited the LPS-induced expression of IKKα/β (IκB kinase alpha/beta), I-κBα (inhibitor of kappa B alpha), nuclear factor kappa-B (NF-κB) p65, iNOS (inducible nitric oxide synthase), and COX-2 (cyclooxygenase-2) in RAW 264.7 cells. Furthermore, LPS-stimulated cytokine production was detected using a sandwich enzyme-linked immunosorbent assay. Compound 1 decreased interleukin 6 (IL-6) and tumor necrosis factor alpha (TNF-α) production in LPS-stimulated RAW 264.7 cells. In summary, the mechanism of action of 1 included the suppression of LPS-induced NO production in RAW 264.7 cells by inhibiting IKKα/β, I-κBα, NF-κB p65, iNOS, and COX-2, and the activities of IL-6 and TNF-α. Full article
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<p>Chemical structures of compounds <b>1–6</b>. 1,5-Dimethyl citrate (<b>1</b>), 5-methoxysalicylic acid (<b>2</b>), syringetin-3-<span class="html-italic">O</span>-glucoside (<b>3</b>), isorhmanetin-3-<span class="html-italic">O</span>-glucoside (<b>4</b>), (+)-dehydrovomifoliol (<b>5</b>), and (+)-vomifoliol (<b>6</b>).</p>
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<p>Effect of compounds <b>1</b>–<b>6</b> on the viability of RAW 264.7 mouse macrophages. (<b>A</b>–<b>F</b>) The viability of RAW 264.7 cells incubated with compounds <b>1–6</b> for 24 h was measured using an Ez-Cytox cell viability assay (mean ± SD, * <span class="html-italic">p</span> &lt; 0.05 compared to the lipopolysaccharide (LPS)-treated group). C: control group treated with 0.5% DMSO. 1,5-dimethyl citrate (<b>1</b>), 5-methoxysalicylic acid (<b>2</b>), syringetin-3-<span class="html-italic">O</span>-glucoside (<b>3</b>), isorhmanetin-3-<span class="html-italic">O</span>-glucoside (<b>4</b>), (+)-dehydrovomifoliol (<b>5</b>), and (+)-vomifoliol (<b>6</b>).</p>
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<p>Effect of compounds <b>1</b>–<b>6</b> on the LPS-stimulated NO production in RAW 264.7 mouse macrophages. The effect of (<b>A</b>–<b>F</b>) the compounds and (<b>G</b>) <span class="html-italic">N</span><sup>G</sup>-methyl-L-arginine acetate salt (L-NMMA) in LPS-treated RAW 264.7 macrophages was detected using the Griess reagent (mean ± SD, * <span class="html-italic">p</span> &lt; 0.05 compared to the LPS-treated group). C: control group treated with 0.5% DMSO. 1,5-Dimethyl citrate (<b>1</b>), 5-methoxysalicylic acid (<b>2</b>), syringetin-3-<span class="html-italic">O</span>-glucoside (<b>3</b>), isorhmanetin-3-<span class="html-italic">O</span>-glucoside (<b>4</b>), (+)-dehydrovomifoliol (<b>5</b>), and (+)-vomifoliol (<b>6</b>).</p>
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<p>Effects of compound <b>1</b> on the LPS-induced expression of the IKKα/β (IκB kinase alpha/beta), I-κBα (inhibitor of kappa B alpha), and NF-κB p65 proteins in RAW 264.7 mouse macrophages. (<b>A</b>) Representative Western blots of IKKα/β, I-κBα, NF-κB p65, and glyceraldehyde 3-phosphate dehydrogenase (GAPDH) protein expression. Quantitative graph of (<b>B</b>) p-IKKα/β, (<b>C</b>) p-I-κBα, and (<b>D</b>) p-p65 (mean ± SD, * <span class="html-italic">p</span> &lt; 0.05 compared to the LPS-treated group). C: control group treated with 0.5% DMSO. 1,5-dimethyl citrate (<b>1</b>).</p>
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<p>Effects of compound <b>1</b> on the LPS-induced expression of iNOS and COX-2 in RAW 264.7 mouse macrophages. (<b>A</b>) Representative Western blots of iNOS, COX-2, and GAPDH protein expression. Quantitative graph of (<b>B</b>) iNOS and (<b>C</b>) COX-2 (mean ± SD, * <span class="html-italic">p</span> &lt; 0.05 compared to the LPS-treated group). C: control group treated with 0.5% DMSO. 1,5-dimethyl citrate (<b>1</b>).</p>
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<p>Effects of compound <b>1</b> on the LPS-induced cytokine release in RAW 264.7 mouse macrophages. (<b>A</b>) Effect of compound <b>1</b> on LPS-induced IL-6 production. (<b>B</b>) Effects of compound <b>1</b> on LPS-induced TNF-α production (mean ± SD, * <span class="html-italic">p</span> &lt; 0.05 compared to the LPS-treated group). C: control group treated with 0.5% DMSO. 1,5-dimethyl citrate (<b>1</b>).</p>
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<p>Schematic model showing the inhibitory effects of compound <b>1</b> on lipopolysaccharide-induced inflammatory response in RAW 264.7 mouse macrophages through the inhibition of IKKα/β, I-κBα, NF-κB p65, inducible nitric oxide synthase (iNOS), and cyclooxygenase-2 (COX-2), and the activities of IL-6 and TNF-α. 1,5-dimethyl citrate (<b>1</b>).</p>
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9 pages, 1344 KiB  
Article
Triterpenoid Saponin and Lignan Glycosides from the Traditional Medicine Elaeagnus angustifolia Flowers and Their Cytotoxic Activities
by Jianxin Han, Xiaoyu Chen, Wei Liu, Hao Cui and Tao Yuan
Molecules 2020, 25(3), 462; https://doi.org/10.3390/molecules25030462 - 22 Jan 2020
Cited by 11 | Viewed by 2572
Abstract
A new triterpenoid saponin, named terpengustifol A (1), and two new lignan glucosides, phengustifols A and B (2 and 3), were isolated from the flowers of Elaeagnus angustifolia. Their structures were determined by the extensive analysis of the [...] Read more.
A new triterpenoid saponin, named terpengustifol A (1), and two new lignan glucosides, phengustifols A and B (2 and 3), were isolated from the flowers of Elaeagnus angustifolia. Their structures were determined by the extensive analysis of the spectroscopic data (including NMR and HRMS) and ECD calculations. Compound 1 possesses an unusual monoterpene (Z)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl unit at C-21. Compounds 2 and 3 are a pair of diastereoisomers, while their aglycones are a pair of enantiomers. Compounds 1 and 2 exhibited moderate cytotoxic activities against A375 cell lines with IC50 values at 12.1 and 15.6 μM, respectively. This is firstly reported the triterpenoid saponin and lignans isolated from the Elaeagnus angustifolia flowers. Full article
(This article belongs to the Section Natural Products Chemistry)
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<p>Chemical structures of compounds <b>1</b>–<b>3</b>.</p>
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<p>(<b>a</b>) Key <sup>1</sup>H-<sup>1</sup>H COSY (−) and selected HMBC correlations (H→C) of <b>1</b>; (<b>b</b>) Key NOESY (↔) correlations of <b>1</b>.</p>
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<p>Key <sup>1</sup>H-<sup>1</sup>H COSY (−) and selected HMBC correlations (H→C) of <b>2</b>.</p>
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<p>(<b>a</b>) Chemical structure of model compound <b>4</b>; (<b>b</b>) Experimental ECD spectra of <b>2</b> and <b>3</b>, and calculated ECD spectra for <b>4</b>.</p>
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15 pages, 822 KiB  
Article
Direct and Indirect Effects of Overstory Canopy and Sex-Biased Density Dependence on Reproduction in the Dioecious Shrub Shepherdia canadensis (Elaeagnaceae)
by Tyler J. Bateman and Scott E. Nielsen
Diversity 2020, 12(1), 37; https://doi.org/10.3390/d12010037 - 19 Jan 2020
Cited by 1 | Viewed by 3343
Abstract
This study assessed the reproductive success of a temperate dioecious shrub, Canada buffaloberry, Shepherdia canadensis (L.) Nutt., in central Alberta, Canada, by examining the effects of spatial patterns and overstory canopy on flower and fruit production. S. canadensis is more abundant and productive [...] Read more.
This study assessed the reproductive success of a temperate dioecious shrub, Canada buffaloberry, Shepherdia canadensis (L.) Nutt., in central Alberta, Canada, by examining the effects of spatial patterns and overstory canopy on flower and fruit production. S. canadensis is more abundant and productive (more fruit) at forest edges and in forest gaps, suggesting a dependence on higher light conditions than is typical of late-seral forests. We used path analysis to demonstrate that flower and fruit production exhibited density-dependent effects at a scale of 50 m2 around focal female plants. Fruit production was positively affected by male intraspecific density (pollen supply) and negatively affected by female intraspecific density (pollen competition), but not correlated with overall intraspecific density. The effects of sex-differentiated density are partly due to pollinator responses to male plant density. Flower production was positively affected by overall intraspecific density. A pollen supplementation trial doubled fruit production relative to a control, demonstrating that local male density (pollen availability) and pollinator activity can limit fruit production in S. canadensis. Canopy cover was negatively related to both flower and total fruit production, with approximately one-third (34%) of the total effect of canopy on fruit production due to the effect of canopy on flower production. The commonly observed negative association between canopy cover and fruit production in buffaloberry, therefore, is partly a result of the reduction first in flower number and second in fruit set. This study clarifies the mechanisms associated with the often-noted observation, but not previously assessed at the level of individuals, that reproductive output in S. canadensis is density dependent, limited by canopy cover through reductions in both flowering and fruit set, and pollinator limited. These findings hold implications for managing animal species that depend on the fruit of S. canadensis and suggest future directions for research on dioecious and actinorhizal species. Full article
(This article belongs to the Section Plant Diversity)
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<p>The small and densely packed red fruit of <span class="html-italic">Shepherdia canadensis</span> (Photo by S. E. Nielsen, 31 July 2009).</p>
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<p>Model describing the effect of light availability (% canopy cover), plant (male, female, and total) density, shrub size (m), and flower production (#/cm of branch) on total fruit production of <span class="html-italic">Shepherdia canadensis</span> in Central Alberta, Canada. Figures beside each path indicate direct effects reported as standardized coefficients. Dashed paths indicate negative coefficients. Indirect effects are not displayed (see <a href="#diversity-12-00037-t002" class="html-table">Table 2</a>). Dashed rectangles indicate endogenous variables. “Density (F)” and “Density (M)” represent density of female and male plants surrounding the focal female shrub, respectively. “Density (D)” indicates the aggregate (total) male and female density surrounding the focal female shrub. Grey paths and rectangle surrounding flower bud formation indicate theorized phenological paths [<a href="#B22-diversity-12-00037" class="html-bibr">22</a>], while all black arrows and rectangles indicate measured variables and estimated path weights.</p>
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17 pages, 1945 KiB  
Article
Anti-Platelet Properties of Phenolic Extracts from the Leaves and Twigs of Elaeagnus rhamnoides (L.) A. Nelson
by Bartosz Skalski, Bogdan Kontek, Agata Rolnik, Beata Olas, Anna Stochmal and Jerzy Żuchowski
Molecules 2019, 24(19), 3620; https://doi.org/10.3390/molecules24193620 - 8 Oct 2019
Cited by 12 | Viewed by 3571
Abstract
Sea buckthorn (Elaeagnus rhamnoides (L.) A. Nelson) is a small tree or bush. It belongs to the Elaeagnaceae family, and has been used for many years in traditional medicine in both Europe and Asia. However, there is no data on the effect [...] Read more.
Sea buckthorn (Elaeagnus rhamnoides (L.) A. Nelson) is a small tree or bush. It belongs to the Elaeagnaceae family, and has been used for many years in traditional medicine in both Europe and Asia. However, there is no data on the effect of sea buckthorn leaves and twigs on the properties of blood platelets. The aim of the study was to analyze the biological activity of phenolic extracts from leaves and twigs of sea buckthorn in blood platelets in vitro. Two sets of extracts were used: (1) phenolic compounds from twigs and (2) phenolic compounds from leaves. Their biological effects on human blood platelets were studied by blood platelet adhesion, platelet aggregation, arachidonic acid metabolism and the generation of superoxide anion. Cytotoxicity was also evaluated against platelets. The action of extracts from sea buckthorn twigs and leaves was compared to activities of the phenolic extract (a commercial product from the berries of Aronia melanocarpa (Aronox®) with antioxidative and antiplatelet properties. This study is the first to demonstrate that extracts from sea buckthorn leaves and twigs are a source of bioactive compounds which may be used for the prophylaxis and treatment of cardiovascular pathologies associated with blood platelet hyperactivity. Both leaf and twig extracts were found to display anti-platelet activity in vitro. Moreover, the twig extract (rich in proanthocyanidins) displayed better anti-platelet potential than the leaf extract or aronia extract. Full article
(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)
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Graphical abstract

Graphical abstract
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<p>Twig (<b>A</b>) and leaf extract (<b>B</b>) (0.5–50 µg/mL; 30 min) on adhesion of resting blood platelets and thrombin-activated platelets to collagen. The inhibition of platelet adhesion by the plant extracts is expressed as the percentage of that recorded for control blood platelets (without the plant extract)–positive control. Data represent mean ± standard error (SE) of 5 (for resting platelets) and 9 (for thrombin-activated platelets) healthy volunteers (each experiment performed in triplicate). * <span class="html-italic">p</span> &lt; 0.05, ** <span class="html-italic">p</span> &lt; 0.02 (vs. control platelets).</p>
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<p>Twig (<b>A</b>) and leaf extract (<b>B</b>) (0.5–50 µg/mL; 30 min) on adhesion of thrombin/adenosine diphosphate (ADP)-activated platelets to fibrinogen. Inhibition of platelet adhesion by the plant extract is expressed as the percentage of that recorded for control blood platelets (without the plant extract)–positive control. Data represent mean ± SE of 5 (for ADP-activated platelets) and (for thrombin-activated platelets) healthy volunteers (each experiment performed in triplicate). * <span class="html-italic">p</span> &lt; 0.05, ** <span class="html-italic">p</span> &lt; 0.02 (vs. control platelets).</p>
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<p>Effects of twig and leaf extract (10 and 50 µg/mL; 30 min) on blood platelet aggregation stimulated by different agonists: 10 µM ADP, 2 μg/mL collagen and 1 Unit/mL thrombin. Data represent mean ± SE of 5 (for thrombin-activated platelets) and 9 (for ADP or collagen-activated platelets) healthy volunteers (each experiment performed in triplicate). Neither concentration of the tested extract (10 and 50 µg/mL) had a statistically significant effect on aggregation stimulated by ADP and collagen compared to control platelets (<span class="html-italic">p</span> &gt; 0.05 (n.s.)). However both concentrations of the tested extract (10 and 50 µg/mL) had a statistically significant effect on aggregation stimulated by thrombin compared to controls (* <span class="html-italic">p</span> &lt; 0.05).</p>
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<p>Twig and leaf extract (1, 5 and 50 µg/mL; 30 min) on the level of thiol groups in glutathione (GSH) fraction (<b>A</b>) and protein fraction (<b>B</b>) isolated from blood platelets. Data represent mean ± SE of 3 (for GSH) and 4 (for protein fraction) healthy volunteers (each experiment done in triplicate). In these experiments, the level of GSH fraction in control sample (positive control–blood platelets not treated with plant extract) was 5.7 ± 0.8 nmol GSH/mL of platelets, and was expressed as 100% (<b>A</b>); the level of thiol groups in protein fraction in control sample (positive control–blood platelets not treated with plant extract) was 112.4 ± 17.4 nmol GSH/mL of platelets, and was expressed as 100% (<b>B</b>). None of three different concentrations of the tested extract (1, 5 and 50 µg/mL) had a statistically significant effect compared to controls (<span class="html-italic">p</span> &gt; 0.05 (n.s.)).</p>
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<p>Twig and leaf extract (1, 5 and 50 µg/mL; 30 min) on the level of thiol groups in glutathione (GSH) fraction (<b>A</b>) and protein fraction (<b>B</b>) isolated from blood platelets. Data represent mean ± SE of 3 (for GSH) and 4 (for protein fraction) healthy volunteers (each experiment done in triplicate). In these experiments, the level of GSH fraction in control sample (positive control–blood platelets not treated with plant extract) was 5.7 ± 0.8 nmol GSH/mL of platelets, and was expressed as 100% (<b>A</b>); the level of thiol groups in protein fraction in control sample (positive control–blood platelets not treated with plant extract) was 112.4 ± 17.4 nmol GSH/mL of platelets, and was expressed as 100% (<b>B</b>). None of three different concentrations of the tested extract (1, 5 and 50 µg/mL) had a statistically significant effect compared to controls (<span class="html-italic">p</span> &gt; 0.05 (n.s.)).</p>
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<p>Twig and leaf extract (0.5, 5 and 50 µg/mL; 30 min) on lipid peroxidation in resting platelets (<b>A</b>) and in blood platelets activated by thrombin (<b>B</b>). In these experiments, blood platelets not treated with plant extract were used as control samples (positive control). Data represent mean ± SE of 6 healthy volunteers (each experiment done in triplicate). The three different concentrations of the twig extract (0.5, 5 and 50 µg/mL) had a statistically significant compared to controls (* <span class="html-italic">p</span> &lt; 0.05). However, none of the three different concentrations of the leaf extract (0.5, 5 and 50 µg/mL) had any statistically significant effect compared to controls (<span class="html-italic">p</span> &gt; 0.05 (n.s.)).</p>
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<p>Twig and leaf extract (0.5, 5 and 50 µg/mL; 30 min) on lipid peroxidation in resting platelets (<b>A</b>) and in blood platelets activated by thrombin (<b>B</b>). In these experiments, blood platelets not treated with plant extract were used as control samples (positive control). Data represent mean ± SE of 6 healthy volunteers (each experiment done in triplicate). The three different concentrations of the twig extract (0.5, 5 and 50 µg/mL) had a statistically significant compared to controls (* <span class="html-italic">p</span> &lt; 0.05). However, none of the three different concentrations of the leaf extract (0.5, 5 and 50 µg/mL) had any statistically significant effect compared to controls (<span class="html-italic">p</span> &gt; 0.05 (n.s.)).</p>
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<p>Effects of twig and leaf extract (0.5 and 5 µg/mL; 30 min) on O<sub>2</sub><sup>−</sup> production in resting platelets (<b>A</b>) and in blood platelets activated by thrombin (<b>B</b>). Data represent mean ± SE of 5 healthy volunteers (each experiment done in triplicate). In these experiments, the O<sub>2</sub><sup>−</sup> level in control samples (positive control – blood platelets not treated with plant extract) was 0.592 ± 0.321 nmol/10<sup>8</sup> platelets (for resting platelets) and 1.222 ± 0.434 nmol/10<sup>8</sup> platelets (for thrombin-activated platelets). Inhibition of O<sub>2</sub><sup>−</sup> production was expressed as a percentage of that recorded for positive control (platelets without tested extracts). The effects of the two different concentrations of twig extract (0.5 and 5 µg/mL) were significantly different to controls (* <span class="html-italic">p</span> &lt; 0.05; ** <span class="html-italic">p</span> &lt; 0.02). The two different concentrations of leaf extract (0.5 and 5 µg/mL) demonstrated no statistically significant effect compared to control platelets (<span class="html-italic">p</span> &gt; 0.05 (n.s.)).</p>
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<p>The toxic effects of twig and leaf extract (0.5–50 µg/mL; 30 min) against human blood platelets. In these experiments, blood platelets not treated with plant extract were used as control samples (positive control). Data represent mean ± SE of 6 healthy volunteers (each experiment performed in triplicate). None of the five different concentrations of the tested extract (0.5, 1, 5, 10 and 50 µg/mL) had any statistically significant effect compared to controls (<span class="html-italic">p</span> &gt; 0.05 (n.s.)).</p>
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Article
Comparative Analysis of the Complete Chloroplast Genome of Four Known Ziziphus Species
by Jian Huang, Ruihong Chen and Xingang Li
Genes 2017, 8(12), 340; https://doi.org/10.3390/genes8120340 - 24 Nov 2017
Cited by 38 | Viewed by 6181
Abstract
Ziziphus Mill. (Rhamnaceae) is comprised of about 170 species that are mainly distributed in tropical to subtropical regions, with few in the temperate zone. Several Ziziphus fruit tree species are important energy, nutrient, and medicinal resources for human populations, particularly for those living [...] Read more.
Ziziphus Mill. (Rhamnaceae) is comprised of about 170 species that are mainly distributed in tropical to subtropical regions, with few in the temperate zone. Several Ziziphus fruit tree species are important energy, nutrient, and medicinal resources for human populations, particularly for those living in rural regions. To date, limited genomic information is available for this genus. Here, we assembled the complete chloroplast genomes of four best known Ziziphus species, i.e., Ziziphus jujuba, Ziziphus acidojujuba, Ziziphus mauritiana, and Ziziphus spina-christi, based on the Illumina Paired-end sequencing method. The chloroplast genomes of the four Ziziphus species are all very similar to one another, and exhibit structural, gene content, and order characteristics that are similar to other flowering plants. The entire chloroplast genome encodes 113 predicted unique genes (85 protein-coding genes, 8 rRNA, and 37 tRNA), 17 of which are duplicated in the inverted repeat regions. Rich single sequence repeats loci (217) were detected in Z. jujuba and 106 SSR loci, composed of A/T, displayed polymorphism across the four species by comparative genomic analysis. We found only four genes under positive selection between Z. jujuba and Z. acidojujuba, and two genes for Z. mauritiana vs. Z. spina-christi, respectively, while half of the 78 protein-coding genes experienced positive selection between the two groups. Phylogenetic analyses revealed that Ziziphus (Rhamnaceae) was sister to Elaeagnaceae, and the four species of Ziziphus were clustered into two groups (Z. jujuba and Z. acidojujuba, Z. mauritiana and Z. spina-christi). Our results provide genomic resources for intrageneric classifications of Ziziphus, and valuable genetic markers for investigating the population genetics and biogeography of closely related Ziziphus species. Full article
(This article belongs to the Special Issue Evolution and Biodiversity of the Plant Genome Architecture)
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<p>Chloroplast genome assembly, size and features of four <span class="html-italic">Ziziphus</span> species. Genes lying outside of the outer layer circle are transcribed in the counter clockwise direction, whereas genes inside are transcribed in the clockwise direction. The colored bars indicate different functional groups. The darker gray area in the inner circle denotes GC content while the lighter gray corresponds to AT content of the genome. LSC: large single copy, SSC: small-single-copy, IR: inverted repeat.</p>
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<p>Comparisons of LSC, SSC, and IR border regions among the four <span class="html-italic">Ziziphus</span> chloroplast genomes.</p>
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<p>Frequency of different simple sequence repeat (SSR) types in the chloroplast genome of <span class="html-italic">Z. jujuba</span>.</p>
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<p>Nucleotide variability (%) values compared among four <span class="html-italic">Ziziphus</span> species. (<b>A</b>) non-coding regions; (<b>B</b>) coding regions.</p>
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<p>Phylogenetic tree reconstruction of the 31 species inferred from maximum likelihood (ML), maximum parsimony (MP) and Bayesian inference (BI), based on 78 protein-coding genes using a non-partitioning scheme. Numbers above the lines represent: ML/MP bootstrap values/BI posterior probability.</p>
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388 KiB  
Review
Sea Buckthorn Oil—A Valuable Source for Cosmeceuticals
by Marijana Koskovac, Snezana Cupara, Mihailo Kipic, Ana Barjaktarevic, Olivera Milovanovic, Ksenija Kojicic and Marija Markovic
Cosmetics 2017, 4(4), 40; https://doi.org/10.3390/cosmetics4040040 - 16 Oct 2017
Cited by 35 | Viewed by 24077
Abstract
Sea buckthorn (Hippophae rhamnoides L., Elaeagnaceae.) is a thorny shrub that has small, yellow to dark orange, soft, juicy berries. Due to hydrophilic and lipophilic ingredients, berries have been used as food and medicine. Sea buckthorn (SB) oil derived from berries [...] Read more.
Sea buckthorn (Hippophae rhamnoides L., Elaeagnaceae.) is a thorny shrub that has small, yellow to dark orange, soft, juicy berries. Due to hydrophilic and lipophilic ingredients, berries have been used as food and medicine. Sea buckthorn (SB) oil derived from berries is a source of valuable ingredients for cosmeceuticals. The unique combination of SB oil ingredients, in qualitative and quantitative aspects, provides multiple benefits of SB oil for internal and external use. Externally, SB oil can be applied in both healthy and damaged skin (burns or skin damage of different etiology), as it has good wound healing properties. Due to the well-balanced content of fatty acids, carotenoids, and vitamins, SB oil may be incorporated in cosmeceuticals for dry, flaky, burned, irritated, or rapidly ageing skin. There have been more than 100 ingredients identified in SB oil, some of which are rare in the plant kingdom (e.g., the ratio of palmitoleic to γ-linolenic acid). This review discusses facts related to the origin and properties of SB oil that make it suitable for cosmeceutical formulation. Full article
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<p>Method for processing SB berries.</p>
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