Browse
Submit Data
Databases
API
Help

Dataset Information

21 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

New Anti-inflammatory Flavonol Glycosides from Lindera akoensis Hayata.

ABSTRACT: Inflammation is related to many diseases. Lindera akoensis Hayata was often used in folktherapy in Taiwan for inflammation. In this study, three new flavonol acyl glycosides, namelykaempferol-3-O--D-4",6"-di-(E)-p-coumaroylglucoside (1), 3"-(E)-p-coumaroylafzelin (2) and 40-Omethyl-2",4"-di-(E)-p-coumaroylquercitrin (3), and three components, 3-dodecyl-4-hydroxy-5-methyldihydrofuran-2-one (4), 2-acetoxyclovan-9-ol (5), (1,4,6)-trihydroxyeudesmane(6) that were isolated from the natural product for the first time were obtained along with 25 knowncompounds from L. akoensis. Their structures were determined by comprehensive spectroscopicanalyses (1D and 2D NMR, EI-, ESI- and HRESI-MS). The ability of 1 to decrease the LPS-stimulatedproduction of nitrite in RAW264.7 cell was evaluated, showing an IC50 value of 36.3 ± 3.2 ?M.This result supports the value of L. akoensis as a traditional medicine resource.

SUBMITTER: Yang CP

PROVIDER: S-EPMC6384965 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

New Anti-inflammatory Flavonol Glycosides from Lindera akoensis Hayata.

Yang Chung-Ping CP Shie Pei-Hsin PH Huang Guan-Jhong GJ Chien Shih-Chang SC Kuo Yueh-Hsiung YH

Molecules (Basel, Switzerland) 20190204 3

Inflammation is related to many diseases. Lindera akoensis Hayata was often used in folktherapy in Taiwan for inflammation. In this study, three new flavonol acyl glycosides, namelykaempferol-3-O--D-4",6"-di-(E)-p-coumaroylglucoside (1), 3"-(E)-p-coumaroylafzelin (2) and 40-Omethyl-2",4"-di-(E)-p-coumaroylquercitrin (3), and three components, 3-dodecyl-4-hydroxy-5-methyldihydrofuran-2-one (4), 2-acetoxyclovan-9-ol (5), (1,4,6)-trihydroxyeudesmane(6) that were isolated from the natural product fo ...[more]

PMID: 30720720

Similar Datasets

Antioxidative, Anti-Inflammatory, and Anticancer Effects of Purified Flavonol Glycosides and Aglycones in Green Tea.

Project description:(1) Background: Extensive research has focused on flavan-3-ols, but information about the bioactivities of green tea flavonols is limited. (2) Methods: In this study, we investigated the antioxidative, anti-inflammatory, and anticancer effects of flavonol glycosides and aglycones from green tea using in vitro cell models. The fractions rich in flavonol glycoside (FLG) and flavonol aglycone (FLA) were obtained from green tea extract after treatment with tannase and cellulase, respectively. (3) Results: FLG and FLA contained 16 and 13 derivatives, respectively, including apigenin, kaempferol, myricetin, and quercetin, determined by mass spectrometry. FLA exhibited higher radical-scavenging activity than that of FLG. FLG and FLA attenuated the levels of intracellular oxidative stress in neuron-like PC-12 cells. The treatment of RAW 264.7 murine macrophages with FLG and FLA significantly reduced the mRNA expression of inflammation-related genes in a dose-dependent manner. Furthermore, FLG and FLA treatments decreased the viability of the colon adenoma cell line DLD-1 and breast cancer cell line E0771. Moreover, the treatment with FLG or FLA combined with paclitaxel had synergistic anticancer effects on the DLD-1 cell line. (4) Conclusions: Flavonols from green tea exerted beneficial effects on health and may be superior to flavan-3-ols.

| S-EPMC6719943 | biostudies-literature

Four new flavonol glycosides from the leaves of Brugmansia suaveolens.

Project description:Four new flavonol glycosides were isolated from the leaves of Brugmansia suaveolens: kaempferol 3-O-?-D-glucopyranosyl-(1'''?2'')-O-?-L-arabinopyranoside (1), kaempferol 3-O-?-D-glucopyranosyl-(1'''?2'')-O-?-L-arabinopyranoside-7-O-?-D-gluco-pyranoside (2), kaempferol 3-O-?-D-[6'''-O-(E-caffeoyl)]-glucopyranosyl-(1'''?2'')-O-?-l-arabinopyranoside-7-O-?-D-glucopyranoside (3), and kaempferol 3-O-?-D-[2'''-O-(E-caffeoyl)]-glucopyranosyl-(1'''?2'')-O-?-l-arabinopyranoside-7-O-?-D-glucopyranoside (4). The structure elucidation was performed by MS, 1D and 2D NMR analyses.

| S-EPMC6271595 | biostudies-literature

Two new acylated flavonol glycosides from the seeds of Lepidium sativum.

Project description:Two new acylated flavonol glycosides named kaempferol-3-O-(2-O-sinapoyl)-?-D-galactopyranosyl-(1 ? 2)-?-D-glucopyranoside-7-O-?-L-rhamnopyranoside (1) and quercetin-3-O-(6-O-benzoyl)-?-D-glucopyranosyl-(1 ? 3)-?-D-galactopyranoside-7-O-?-L-rhamnopyranoside (2), were isolated together with six known compounds from the seeds of L. sativum. Their structures were elucidated on the basis of spectroscopic analysis and chemical methods. In vitro 1 and 2 inhibited nitric oxide production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells, with IC50 values of 25.36 and 25.08 µM, respectively.

| S-EPMC6271768 | biostudies-literature

Novel flavonol glycosides from the aerial parts of lentil (Lens culinaris).

Project description:While the phytochemical composition of lentil (Lens culinaris) seeds is well described in scientific literature, there is very little available data about secondary metabolites from lentil leaves and stems. Our research reveals that the aerial parts of lentil are a rich source of flavonoids. Six kaempferol and twelve quercetin glycosides were isolated, their structures were elucidated using NMR spectroscopy and chemical methods. This group includes 16 compounds which have not been previously described in the scientific literature: quercetin 3-O-?-D-glucopyranosyl(1?2)-?-D-galactopyranoside-7-O-?-D-glucuropyranoside (1), kaempferol 3-O-?-D-glucopyranosyl(1?2)-?-D-galacto-pyranoside-7-O-?-D-glucuropyranoside (3), their derivatives 4-10,12-15,17,18 acylated with caffeic, p-coumaric, ferulic, or 3,4,5-trihydroxycinnamic acid and kaempferol 3-O-{[(6-O-E-p-coumaroyl)-?-D-glucopyranosyl(1?2)]-?-L-rhamnopyranosyl(1?6)}-?-D-galactopyranoside-7-O-?-L-rhamnopyranoside (11). Their DPPH scavenging activity was also evaluated. This is probably the first detailed description of flavonoids from the aerial parts of lentil.

| S-EPMC6270693 | biostudies-literature

Anti-Inflammatory Triterpene Glycosides from the Roots of Ilex dunniana Levl.

Project description:A new triterpene glycoside ilexdunnoside A (1) and a new sulfated triterpene derivative ilexdunnoside B (2), together with five known analogues 3-7 were isolated from the roots of Ilex dunniana Levl. The structures were established by NMR spectroscopic analysis and acid hydrolysis. Results of an in vivo study of the biological activity showed that 75% ethanol and n-butanol extracts of the plant displayed anti-inflammatory activities against ear edema in mice, with inhibition rates of 23.5% and 37.5%, respectively, at a dose of 50 mg/kg. Furthermore, Compounds 1, 2 and 3 exhibited moderate indirect inhibitory effects on lipopolysaccharide-induced NO production in BV2 microglial cells in vitro, with IC50 values of 11.60, 12.30 and 9.70 ?M, respectively.

| S-EPMC6152231 | biostudies-literature

Tripterygium wilfordii Glycosides Upregulate the New Anti-Inflammatory Cytokine IL-37 through ERK1/2 and p38 MAPK Signal Pathways.

Project description:As a Chinese traditional patent medicine, Tripterygium wilfordii glycosides (TWG) have been approved by the China State Food and Drug Administration (Z32021007) for autoimmune and inflammatory diseases. Application of TWG leads to significant decrease of the inflammatory cytokines, such as IL-6, IL-1?, and TNF-?. However, little is known whether TWG could regulate the anti-inflammatory cytokines and what the mechanism is. Here, we found that TWG could induce the upregulation of IL-37 which is a new anti-inflammatory cytokine. Furthermore, the inhibitors of ERK1/2 and/or p38 MAPK pathways suppressed IL-37 expression induced by TWG, indicating that the two pathways took part in this process. In conclusion, TWG could upregulate the anti-inflammatory cytokine IL-37 and ERK1/2 and p38 MAPK signal pathways were involved in the upregulation of IL-37 induced by TWG. The results showed that TWG had a potent activity on promoting the expression of IL-37, a new anti-inflammatory cytokine, which help further understanding the anti-inflammatory mechanism for the clinical application of TWG in therapy of diseases.

| S-EPMC5748296 | biostudies-literature

Terpene Glycosides from <i>Sanguisorba officinalis</i> and Their Anti-Inflammatory Effects.

Project description:Two new terpene glycosides (1-2) along with two known analogs (3-4) were obtained from the root of Sanguisorba officinalis, which is a common traditional Chinese medicine (TCM). Their structures were elucidated by nuclear magnetic resonance (NMR), electrospray ionization high resolution mass spectrometry (HRESIMS), and a hydrolysis reaction, as well as comparison of these data with the literature data. Compounds 1-4 exhibited anti-inflammatory properties in vitro by attenuating the production of inflammatory mediators, such as nitric oxide (NO) as well as tumor necrosis factor-? (TNF-?) and interleukin-6 (IL-6). An anti-inflammatory assay based on the zebrafish experimental platform indicated that compound 1 had good anti-inflammatory activity in vivo by not only regulating the distribution, but also by reducing the amount of the macrophages of the zebrafish exposed to copper sulfate.

| S-EPMC6720167 | biostudies-literature

Topical anti-inflammatory effects of isorhamnetin glycosides isolated from Opuntia ficus-indica.

Project description:Opuntia ficus-indica (OFI) has been widely used in Mexico as a food and for the treatment of different health disorders such as inflammation and skin aging. Its biological properties have been attributed to different phytochemicals such as the isorhamnetin glycosides which are the most abundant flavonoids. Moreover, these compounds are considered a chemotaxonomic characteristic of OFI species. The aim of this study was to evaluate the effect of OFI extract and its isorhamnetin glycosides on different inflammatory markers in vitro and in vivo. OFI extract was obtained by alkaline hydrolysis of OFI cladodes powder and pure compounds were obtained by preparative chromatography. Nitric oxide (NO), cyclooxygenase-2 (COX-2), tumor necrosis factor- (TNF-) ?, and interleukin- (IL-) 6 production were measured. NO production was tested in lipopolysaccharide-stimulated RAW 264.7 cells while in vivo studies were carried on croton oil-induced ear edema model. OFI extract and diglycoside isorhamnetin-glucosyl-rhamnoside (IGR) at 125?ng/mL suppressed the NO production in vitro (73.5 ± 4.8% and 68.7 ± 5.0%, resp.) without affecting cell viability. Likewise, IGR inhibited the ear edema (77.4 ± 5.7%) equating the indomethacin effects (69.5 ± 5.3%). Both IGR and OFI extract significantly inhibited the COX-2, TNF-?, and IL-6 production. IGR seems to be a suitable natural compound for development of new anti-inflammatory ingredient.

| S-EPMC4363586 | biostudies-literature

The flavonol glycosides in the fruit of Pyrus communis L. cultivar Bon Chretien.

Project description:1. Two new flavonol glycosides were isolated from the fruit of Pyrus communis L. cultivar Bon Chrétien. These were identified as isorhamnetin 3-rhamnogalactoside and a derivative of isorhamnetin 3-glucoside which was associated (possibly acylated) with an unknown aliphatic organic acid. 2. The melting point of isorhamnetin 3-glucoside isolated from Bon Chrétien pears is different from that of isorhamnetin 3-glucoside previously isolated from Argemone mexicana and Calendula officinalis. 3. Isorhamnetin 3-rhamnoglucoside was isolated from the fruit of Pyrus communis L. cultivar Bon Chrétien. This glycoside appears to be identical with narcissin, previously isolated from Narcissus tazetta and Lilium auratum. 4. Isoquercitrin, previously reported to be present in pear leaves, was isolated from the fruit of Bon Chrétien pears. 5. The isolated glycosides were present in the peels and flesh of the fruit, but were absent from the cores.

| S-EPMC1264563 | biostudies-other

Anti-Inflammatory Principles from the Needles of <i>Pinus taiwanensis</i> Hayata and In Silico Studies of Their Potential Anti-Aging Effects.

Project description:Pinus needle tea are very popular in Eastern countries such as Japan, Russia, Korea, and China. Pine needle tea is claimed to have significant anti-aging effects, but no clear evidence has supported this until now. In the present study, five undescribed compounds (1-5) as well as seventy-two known compounds were purified and characterized from the bioactive fraction of methanol extracts of P. taiwanensis needles. Most of the isolates were examined for their anti-inflammatory bioactivity by cellular neutrophil model and six compounds (45, 47, 48, 49, 50, and 51) exhibited a significant inhibition on superoxide anion generation and elastase release with IC50 values ranging from 3.3 ± 0.9 to 8.3 ± 0.8 μM. These anti-inflammatory ingredients were subjected to docking computing to evaluate their binding affinity on the ghrelin receptor, which played an important role in regulating metabolism, with anti-aging effects. Compounds 49, 50, and 51 formed a stable complex with the ghrelin receptor via hydrogen bonds and different types of interactions. These results suggest the flavonoids are responsible for the potential anti-aging effects of pine needle tea.

| S-EPMC8069155 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data