Aqueous EtOH Extract Research Articles

Dammarane-type saponins from Gynostemma pentaphyllum and their anti-aging activities via up-regulating mitochondria related proteins

The importance of mitochondria in regulation of aging has been extensively recognized and confirmed. Gynostemma pentaphyllum (Thunb.) Makino, a homology of medicine and food, has been widely utilized as dietary supplement. In this study, the transcriptome of normal cells (wild type mouse embryo fibroblasts) regulated by the 30% aqueous EtOH extract of G. pentaphyllum was firstly evaluated by RNA sequencing and the results revealed that the G. pentaphyllum could up-regulate the genes involved in oxidative phosphorylation (OXPHOS) and sirtuin (SIRT) signaling pathways, indicating its effect in promoting cell viability might be attributed to the role of improving mitochondrial functions. To further discover the bioactive compounds, sixteen undescribed dammarane-type saponins along with twenty-eight known analogues were isolated from the active extract of G. pentaphyllum. Their structures were elucidated by means of comprehensive analysis of NMR and HRMS spectroscopic data. All isolates were evaluated for the regulatory effects on SIRT3 and translocase of the outer membrane 20 (TOM20), and thirteen of them exhibited satisfactory agonist activities on both SIRT3 and TOM20 at 5 μM. Furthermore, the preliminary structure-activity relationships analysis demonstrated the additional hydroxymethyl and carbonyl groups or less sugar residues in saponins could contribute positively to the up-regulatory effect on SIRT3 and TOM20. These findings encouraged the potential roles of G. pentaphyllum and its bioactive saponins in the development of natural drugs for the treatment of aging-related diseases.

Acylated sucroses and butenolide analog from the leaves of Tripterygium wilfordii Hook. f. and their potential anti-tyrosinase effects

Three undescribed acylated sucroses (1–3), one undescribed butenolide analog (4) along with three known compounds (5–7) were isolated from the aqueous EtOH extract of the dried leaves of Tripterygium wilfordii. Their structures were elucidated on the basis of spectroscopic analyses, electron circular dichroism (ECD) techniques, and saccharide hydrolysis. All the isolated compounds were tested for their anti-tyrosinase effects. Among them, 6 exhibited similar inhibitory effects on tyrosinase with IC50 values of 0.073 mM comparing to arbutin. Additionally, the possible mechanism of the interaction between 6 and the active site of tyrosinase was explored by molecular docking.

New compounds from Patrinia villosa Juss. and their anti-inflammatory activities

Five new iridoids, patriscabioins M-Q and a new monoterpene, eldanolide acid, together with three known iridoids, were isolated from the 95% aqueous EtOH extract whole plants of Patrinia villosa Juss. The structures were established by a variety of spectroscopic analysis, such as IR, 1 D and 2 D NMR spectra, MS, ECD and X-ray diffraction data. Bioactivity screening revealed the inhibitory effects on nitric oxide (NO) production of them in lipopolysaccharide-activated RAW264.7 cells with Aminoguanidine Hydrochloride as the positive control. Among them, patriscabioin M (1), patriscabioin N (2), patriscabioin P (4), patriscabioin Q (5), 8,9-didehydro-7-hydroxydolichodia (7) were found to markedly reduce LPS-induced NO production in murine macrophage cells with IC50 values of 18.14, 18.93, 22.00, 13.64, 26.48 μM, respectively.

Abietane diterpenoids from Dracocephalum moldavica L. and their anti-inflammatory activities in vitro

Five undescribed abietane diterpenoids, dracocephalumoids A–E, together with six known analogues were isolated from the aqueous EtOH extract of aerial parts of Dracocephalum moldavica L.. The structures were elucidated through extensive analysis of spectroscopic data, and their absolute configurations were established by Mosher's method and time-dependent density functional theory electronic circular dichroism (TDDFT ECD) calculation. Cell-based anti-inflammatory assays displayed that dracocephalumoid A, uncinatone, trichotomone F and caryopterisoid C showed potent suppressive effects against TNF-α, IL-1β or NO production in LPS-induced RAW 264.7 cells, with IC50 values ranging from 1.12 to 5.84 μM. The structure-activity relationship of these compounds was also discussed.

Development of a colorless Centella asiatica (L.) Urb. extract using a natural deep eutectic solvent (NADES) and microwave-assisted extraction (MAE) optimized by response surface methodology.

This study outlines a green process for Centella asiatica (L.) Urb. (CA) extraction. Natural deep eutectic solvents (NADESs) and microwave-assisted extraction (MAE) were combined to provide a high bioactive compound yield and high antioxidant activity. Among the NADESs evaluated, the combination of acetylcholine chloride : malic acid : water (1 : 2 : 2): water (40 : 60) was the best for extraction. These conditions provide high madecassoside (MS) (21.7 mg g−1 dry weight) and asiaticoside (AS) (12.7 mg g−1 dry weight) yields, with greater than 80% (v/v) EtOH (13.3 mg g−1 MS and 7.80 mg g−1 AS). In addition, the extracts from this process showed higher antioxidant activity (IC50 = 0.26 mg mL−1) than the CA aqueous EtOH and water extracts. Moreover, the color of the extract products was less green than that of the extracts prepared using EtOH and aqueous EtOH as solvents, which are suitable for cosmeceutical products. Response surface methodology (RSM) was used for MAE optimization. The ANOVA data from the central composition design (CCD) of RSM were fitted with quadratic models yielding acceptable R2 (>0.93), adjusted R2 (>0.87), predicted R2 (>0.81), and nonsignificant lack of fit (p > 0.05) values. The quadratic model was validated using optimal conditions (30 s, power 300 W, and a liquid to solid ratio 20 mL g−1), and the model validation showed more than 80% accuracy in both MS and AS yields. This research presented an effective green process for CA extraction, which resulted in an environmentally friendly CA extract requiring little energy consumption and no organic solvents.

A New Biflavonoid from Selaginella uncinata

One new robustaflavone, (2S,2′′S)-2,3,2′′ ,3′′-tetrahydrorobustaflavone 7,4′,4′′′ -trimethyl ether (1), was isolated from the 75% aqueous EtOH extract of Selaginella uncinata. The structure and absolute configuration of 1 was established by extensive spectroscopic and circular dichroism analyses.

Monoterpenoid coumarins and monoterpenoid phenylpropanoids from the root bark of Ailanthus altissima

Three new monoterpenoid coumarins, zantholin A (3), altissimacoumarin P-Q (5, 6), two new monoterpenoid phenylpropanoids, altissmaphenylpropanoids A-B (2, 4), along with two known compounds (7, 8), were obtained from aqueous EtOH extracts of the root bark of Ailanthus altissima.

Diterpenoids and triterpenoids from Triadica rotundifolia and their effects on microglial nitric oxide production

Four new diterpenoids (1–4), three new triterpenoids (12–14), and seven known diterpenoids (5–11) were obtained from an aqueous EtOH extract of the aerial parts of Triadica rotundifolia. The structures of new compounds were determined by spectroscopic techniques. Their absolute configurations were verified via single-crystal X-ray diffraction data, Mo2(OAc)4 induced electronic circular dichroism (ECD), and ECD calculations. The antineuroinflammatory effects of the isolates were assessed by inhibiting NO production in LPS-induced BV-2 microglial cells. Compared with the positive control minocycline (IC50 = 16.1 μM), compounds 3, 8, 11 showed moderate inhibitory activities with IC50 values of 35.9, 17.0, 31.5 μM, respectively.

Antioxidant Properties of Extracts of Leaves and Inflorescences of Spiraea Media Franz Schmidt from the Flora of Komi Republic

The antioxidant activity of aqueous and aqueous-EtOH extracts of Spirea media leaves and inflorescences collected from a natural population (Ust-Kulomsky District, Komi Republic) was determined. It was shown that the extracts were characterized by high contents of polyphenols (from 41.14 to 71.79 mg GAE/g dry weight), which are important natural antioxidants. It was found that the aqueous extracts of inflorescences and leaves had less radical-binding activity (RBA) than the aqueous-EtOH extracts. At the same time, the RBA of the aqueous-EtOH extract of leaves was greater than that of inflorescences. Astrong correlation between the RBA and the content of polyphenols in the extracts was found (r = –0.80, p < 0.05). Chelating activity (CA) that was highest in aqueous extracts of spirea leaves was found for all extracts. The aqueous-EtOH extract of inflorescences had greater CA than the aqueous extract.

Comparative Spectroscopic and HPLC Analyses of Phenolic Compounds in Extracts of Anthocyanin Maize Purple Saratov Variety Grown Under Various Wetting Conditions

The quercetin content in aqueous EtOH extracts of covering leaves of anthocyanin Purple Saratov diploid variety of Zea mays L. grown under dry conditions reached 39.36 ± 0.41 mg/100 g of dry extract and significantly exceeded the value (26.03 ± 0.36 mg/100 g of dry extract) for maize grown under normal wetting conditions. The large amounts of polyphenolic compounds in anthocyanin Purple Saratov diploid variety showed good prospects for using it as a source of them.

Viburnumfocesides A – D, 1-O-isovaleroylated iridoid 11-O-alloside derivatives from Viburnum foetidum var. ceanothoides

Viburnumfocesides A - D, four undescribed 1-O-isovaleroylated iridoid 11-O-allosides modified with (Z / E)-p-coumaric acid, were isolated from the aqueous EtOH extract of the twigs of Viburnum foetidum var. ceanothoides, together with seven known natural products. Their structures were identified on the basis of the spectroscopic data interpretation and chemical derivation studies. Cell-based estrogen biosynthesis assays indicated that viburnumfoceside D (4), (2S,3R)-2,3-dihydro-3-hydroxymethyl-7-methoxy-2-(4-hydroxy-3-methoxyphenyl)-5-benzofuranpropanol-3a-O-α-L-rhamnopyranoside (8), and (-)-eriodictyol (11) inhibit estrogen biosynthesis with IC50 values of 5.8, 1.5, and 1.1 μM, respectively, in human ovarian granulosa-like KGN cells via decreasing the expression level of aromatase.

Repair of Erythrocyte Membranes by the Lipid Fraction from Brown Seaweed Sargassum Pallidum after Experimental Ccl4-Induced Toxic Hepatitis

The influence of the lipid fraction from the aqueous EtOH extract of brown seaweed Sargassum pallidum thallus and the commercial reference drug Essentiale® on the physiological characteristics of rat erythrocytes and the lipid composition of erythrocyte membranes after CCl4-induced toxic injury was studied. CCl4 intoxication (50% solution in olive oil, s.c., 2 mL/kg for 4 d) was associated with changes of all studied physiological and biochemical erythrocyte parameters that did not return to normal after withdrawing the toxicant. Intragastric administration to rats through a probe of the lipid fraction from S. pallidum extract at a dose of 80 mg of total lipids per kg of mass for 7 d after CCl4 intoxication gave membrane protection that manifested as a restoration of the characteristic erythrocyte dimensions (average volume and diameter), extension of the threshold to their hemolysis stability, and retention of the lipid constituent ratio in the membrane. The lipid fraction from brown seaweed S. pallidum was comparable to Essentiale® for restoring erythrocyte physiological characteristics and the lipid composition of their membranes after CCl4-induced damage. The pronounced protective effect of the S. pallidum lipid fraction for repairing erythrocyte membranes was evidently determined by the combined action of the marine lipids in it.

An NMR-Based Chemometric Strategy to Identify Leishmania donovani Nucleoside Hydrolase Inhibitors from the Brazilian Tree Ormosia arborea.

Nucleoside hydrolases are a strategic target for the development of drugs to treat leishmaniasis, a neglected disease that affects 700 thousand to one million people annually. The present study aimed to identify Leishmania donovani nucleoside hydrolase (LdNH) inhibitors from the leaves of Ormosia arborea, a tree endemic to Brazilian ecosystems, through a strategy based on 1H NMR analyses and chemometrics. The aqueous EtOH extract of O. arborea leaves inhibited LdNH activity by 95%. The extract was fractionated in triplicate (13 in each step, making a total of 39 fractions). Partial least squares discriminant analysis (PLS-DA) was used to correlate the 1H NMR spectra of the fractions with their LdNH inhibitory activity and thus to identify the spectral regions associated with the bioactivity. The strategy aimed at isolating the probable bioactive substances and led to two new A-type proanthocyanidins, linked to a p-coumaroyl unit (1 and 2), which appeared as noncompetitive inhibitors of LdNH (IC50: 28.2 ± 3.0 μM and 25.6 ± 4.1 μM, respectively). This study confirms the usefulness of the NMR-based chemometric methods to accelerate the discovery of drugs from natural products.

Tripterfordins A-O, Dihydro-β-agarofuran Sesquiterpenoids from the Leaves of Tripterygium wilfordii.

Fifteen new dihydro-β-agarofuran-type sesquiterpenoids, tripterfordins A-O, were obtained from the aqueous EtOH extracts of the leaves of Tripterygium wilfordii. These constituted a class of highly oxygenated tricyclic sesquiterpenoid polyesters with a cinnamoyloxy group at C-1. The assignments of their structures were conducted via extensive analyses of the spectroscopic data and comparison of experimental and calculated ECD data. The absolute configurations of compounds 1, 4, 9, and 10 were established via single-crystal X-ray diffraction data. Additionally, compounds 1, 4, 9, 10, and 13 exhibited pronounced inhibitory effects on nitric oxide production in RAW 264.7 murine macrophages stimulated by lipopolysaccharide with IC50 values ranging from 11.9 to 31.0 μM.

Dihydro-β-agarofuran sesquiterpenoid derivatives with anti-inflammatory activity from the leaves of Tripterygium wilfordii

Triptersinoids A-E (1–5), five undescribed highly oxygenated dihydro-β-agarofuran type sesquiterpenoid polyesters, along with three known analogues were isolated from the aqueous EtOH extracts of the dried leaves of Tripterygium wilfordii. Spectroscopic techniques were used for the elucidation of their chemical structures, and the absolute configurations determined by means of electron circular dichroism (ECD) studies, including octant rule of saturated cyclohexanone and comparison between the experimental and calculated ECD data. These compounds were evaluated for the anti-inflammatory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 macrophages, and 1α,2α,8β,15-tetraacetoxy-9α-benzoyloxyl-15-nicotinoyloxy-β-dihydroagarofuran (7) and angulateoid B (8) showed potential inhibitory effects with IC50 values of 17.30 ± 1.07 μM and 20.79 ± 1.55 μM.

Isolation, Structural Elucidation, Optical Resolution, and Antineuroinflammatory Activity of Phenanthrene and 9,10-Dihydrophenanthrene Derivatives from Bletilla striata.

A phytochemical investigation of the aqueous EtOH extract of Bletilla striata tubers afforded 34 phenanthrene and 9,10-dihydrophenanthrene derivatives, including four new compounds, 1-4. These compounds were identified using physicochemical analyses and various spectroscopic methods. Twelve of these compounds were resolved into their enantiomers, and the absolute configurations were determined by comparison of experimental and calculated ECD spectra. The antineuroinflammatory activities were evaluated by measuring the inhibition of nitric oxide production in lipopolysaccharide-stimulated BV-2 microglial cells. Compounds 7, 32, and 33 displayed inhibitory activities, with IC50 values of 1.9, 5.0, and 1.0 μM, respectively, suggesting that they should be subjected to development as potential inhibitors of neuroinflammation.

Angionorm Complex Herbal Preparation Constituents Identified by High Performance Liquid Chromatography-Mass Spectrometry

Angionorm is an original Russian preparation based on the dried aqueous EtOH (25%) extract of a herbal mixture containing horse chestnuts (Aesculus hippocastanum L.), licorice roots (Glycyrrhiza glabra L.), hawthorn fruit (Crataegus), and dog-rose hips (Rosa canina). Areversed-phase HPLC-MS-MS procedure with gradient elution was developed to identify the main constituents in extracts of the mixture and each raw material type. Standards helped to identify 15 compounds of various classes (phenolic and hydroxycinnamic acids and their esters, flavonoids, flavonoid glycosides, triterpene saponins). Peaks of hyperoside, liquiritin, â-glycyrrhizic acid, and escin isomers were identified using MRM transitions, elution order, and literature data. Herbal sources of identified constituents were determined. Marker compounds characteristic of each raw-material type in the mixture extract were proposed.

Cytotoxic polyhydroxy serratene triterpenoids from Lycopodium complanatum

Phytochemical investigation of the 70% aqueous EtOH extract of Lycopodium complanatum led to six new polyhydroxy serratene triterpenoids (serrat A-F, 1–6), along with a known analogue (7). Their structures and configurations were elucidated by data analysis of HRESIMS, 1D and 2D NMR, in combination with comparisons of reported experimental spectroscopic data. All the isolates were evaluated cytotoxic activities against HepG2 cells, MCF-7 cells and series human lung cancer cell lines A549, Calu-6, NCI-H441, NCI-H226 and NCI-H1975. The results indicated that certain compounds inhibited proliferation of human cancer cells. Moreover, all compounds possessed selective cytotoxic activities on MCF-7 cells. Further, possible biosynthesis pathways of these compounds were proposed.

Chemical Constituents from Leaves of Hydrangea serrata and Their Anti-photoaging Effects on UVB-Irradiated Human Fibroblasts.

Hydrangea serrata (THUNB.) SER. (Hydrangeaceae) leaves have been used as herbal teas in Korea and Japan. The objective of this study was to identify anti-photoaging compounds in aqueous EtOH extract prepared from leaves of H. serrata and their effects on UVB-irradiated Hs68 human foreskin fibroblasts. Phytochemical study on H. serrata leaves led to the isolation and characterization of ten compounds: hydrangenol, thunberginol A, thunberginol C, hydrangenoside A, hydrangenoside C, cudrabibenzyl A, 2,3,4'-trihydroxystilbene, thunberginol F, quercetin 3-O-β-D-xylopyranosyl (1-2)-β-D-galactopyranoside, quercetin 3-O-β-D-xylopyranosyl (1-2)-β-D-glucopyranoside. Cudrabibenzyl A, 2,3,4'-trihydroxystilbene, quercetin 3-O-β-D-xylopyranosyl (1-2)-β-D-galactopyranoside, quercetin 3-O-β-D-xylopyranosyl (1-2)-β-D-glucopyranoside were firstly isolated from H. serrata. We estimated the effects of 10 compounds on cell viability and production of pro-collagen Type I, matrix metalloproteinase (MMP)-1, and hyaluronic acid (HA) after UVB irradiation. Of these compounds, hydrangenol showed potent preventive activities against reduced cell viability and degradation of pro-collagen Type I in UVB-irradiated Hs68 fibroblasts. Hydrangenol had outstanding inductive activities on HA production. It suppressed mRNA expression levels of MMP-1, MMP-3, hyaluronidase (HYAL)-1, HYAL-2, cyclooxygenase-2 (COX-2), interleukin (IL)-6, IL-8, and IL-1β in UVB-irradiated Hs68 fibroblasts. When Hs68 fibroblasts were exposed to hydrangenol after UVB irradiation, UVB-induced reactive oxygen species (ROS) production was suppressed. Hydrangenol also inhibited the activation of activator protein-1 (AP-1) and signal transduction and activation of transcription 1 (STAT-1) by downregulating phosphorylation of p38 and extracellular signal-regulated kinase (ERK). Our data indicate that hydrangenol isolated from H. serrata leaves has potential protective effects on UVB-induced skin photoaging.

Non-glycosidic iridoids from the roots of Patrinia scabra and their nitric oxide production inhibitory effects.

Phytochemical investigation on the 70% aqueous EtOH extract from the roots of Patrinia scabra led to the isolation and characterization of five new non-glycosidic iridoids, patriscabrins F-J (1-5), along with a known iridoid 11-ethoxyviburtinal (6). The structures of the new compounds 1-5 were determined by interpretation of spectroscopic data, particularly by 1D- and 2D-NMR and ECD studies. Thereafter, the isolates 1-6 were evaluated for their inhibitory effects on lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells. Of these, patriscabrin F (1) exhibited the most potent inhibitory effect with observed IC50 value of 14.1μM. In addition, patriscabrin G (2) and 11-ethoxyviburtinal (6) showed IC50 values 24.6 and 35.5μM, respectively.