Isoferulic Acid

CAS# 537-73-5

Isoferulic Acid

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Chemical structure

Isoferulic Acid

3D structure

Chemical Properties of Isoferulic Acid

Cas No. 537-73-5 SDF Download SDF
PubChem ID 736186.0 Appearance Powder
Formula C10H10O4 M.Wt 194.19
Type of Compound Phenylpropanoids Storage Desiccate at -20°C
Synonyms Hesperetic acid; Hesperetinic acid; Extra CAS No: 24276-84-4, 25522-33-2
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
SMILES COC1=C(C=C(C=C1)C=CC(=O)O)O
Standard InChIKey QURCVMIEKCOAJU-HWKANZROSA-N
Standard InChI InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Isoferulic Acid

Cimicifuga racemosa, Catalpa ovata, Ixora javanica and other plants Powder

Isoferulic Acid Dilution Calculator

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Isoferulic Acid Molarity Calculator

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Preparing Stock Solutions of Isoferulic Acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.1496 mL 25.748 mL 51.496 mL 102.9919 mL 128.7399 mL
5 mM 1.0299 mL 5.1496 mL 10.2992 mL 20.5984 mL 25.748 mL
10 mM 0.515 mL 2.5748 mL 5.1496 mL 10.2992 mL 12.874 mL
50 mM 0.103 mL 0.515 mL 1.0299 mL 2.0598 mL 2.5748 mL
100 mM 0.0515 mL 0.2575 mL 0.515 mL 1.0299 mL 1.2874 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Isoferulic Acid

Exploring the effective compounds and potential mechanisms of Shengxian Decoction against coronary heart disease by UPLC-Q-TOF/MS and network pharmacology analysis.[Pubmed:38681620]

Heliyon. 2024 Apr 16;10(8):e29558.

As a well-known classical Chinese medicine prescription, Shengxian Decoction (SXD) has been applied for a century to treat cardiovascular diseases, especially coronary heart disease (CHD), but the potentially effective compounds and underlying mechanisms remain unclear. With ultra-performance liquid chromatography-quadrupole-time of flight-mass spectrometry (UPLC-Q-TOF/MS) and network pharmacology analysis, the potential effective compounds of SXD and their pharmacological mechanisms against CHD were identified and revealed. 57 effective compounds with favorable pharmacokinetic characteristics and biological activities were screened through UPLC-Q-TOF/MS analysis, database and literature mining, interacting with 96 CHD-related targets to support potential synergistic therapeutic actions. Systematic analysis of the PPI network and microarray data further revealed six core targets, including TNF, IL-1beta, IL-6, TP53, VEGFA and PTGS2, which were mainly involved in fluid shear stress and atherosclerosis, lipid and atherosclerosis, PI3K-Akt signaling pathway et al. Moreover, the proposed contribution indexes of effective compounds indicated these compounds, including Isoferulic Acid, quercetin, calycosin, ferulic acid, kaempferol, calycosin 7-O-glycoside, formononetin, astragaloside IV and saikosaponin D, as the core compounds of SXD. The molecular docking results confirmed that those core compound-target pairs exhibited strong binding energy. Furthermore, we validated that SXD significantly alleviated myocardial tissue injury in CHD rats and reversed H/R-induced decreases in H9c2 cell viability by attenuating the production of TNF, IL-6 and IL-1beta, and reducing cardiomyocyte apoptosis via down-regulating the TP53, caspase3 and cytochrome C mRNA expression levels as well as caspase3, caspase9 and cytochrome C protein expression levels according to RT-qPCR and Western blot results. Our findings explained the pharmacological mechanisms underlying the effectiveness of SXD in the treatment of CHD, and laid a foundation for future basic and clinical research of SXD.

Anti-inflammatory effects of immature Citrus unshiu fruit extracts via suppression of NF-kappaB and MAPK signal pathways in LPS-induced RAW264.7 macrophage cells.[Pubmed:38371697]

Food Sci Biotechnol. 2023 Jul 24;33(4):903-911.

This study examined the anti-inflammatory effects of 70% ethanol crude extract of immature Citrus unshiu fruits (ICE) and its solvent fractions in LPS-stimulated RAW 264.7 cells. In addition, we analyzed the active compounds related to suppression of inflammation. It was found that the ethyl acetate (EtOAc) fraction showed the highest level of inhibition of NO production, and this inhibitory activity was concentration-dependent. Moreover, the EtOAc fraction not only inhibited TNF-alpha and IL-6 production but also inhibited iNOS and COX-2 protein expression. Furthermore, inhibition of NF-kappaB activity and MAPK phosphorylation was also observed. In addition, beta-sitosterol, campesterol and Isoferulic Acid were identified as major anti-inflammatory components in the EtOAc fraction. These results suggested that the EtOAc fraction of immature C. unshiu fruit extract exerts anti-inflammatory effects by inhibiting NF-kappaB and MAPK signaling pathways, and that this fruit could be used as a natural anti-inflammatory material.

Optimization of the Zhou Tian Formula extraction technology based on AHP-CRITIC method and analysis of transfer efficiency of key components based on HPLC fingerprinting.[Pubmed:38366710]

Phytochem Anal. 2024 Feb 17.

INTRODUCTION: Zhou Tian Formula (ZTF) is an antidepressant traditional Chinese medicine utilized widely in clinical settings for the treatment of patients with depression. However, shortcomings persist in its extraction technology and quality control. OBJECTIVE: This study aimed to propose a methodology for ZTF extraction technology based on the analytic hierarchy process (AHP)-criteria importance through intercriteria correlation (CRITIC) method and to establish a quality control framework for the efficient transfer of index components. METHOD: Firstly, we analyzed the chemical components of ZTF and determined the optimal extraction technology. Secondly, we calculated the transfer efficiency of the index components during the conversion of water decoction to extract powder and subsequently to granules. Thirdly, we established HPLC fingerprints for 15 batches of ZTF water decoction, extract powder, and granules. We employed SIMCA software to analyze the chemicals responsible for variations in quality among different batches of ZTF granules. RESULTS: We determined the optimal extraction process. The average transfer efficiency of ferulic acid, puerarin, mirificin, Isoferulic Acid, and calycosin during the conversion of water decoction to extract powder and subsequently to granules exceeded 41%. The HPLC fingerprints of ZTF exhibited a similarity exceeding 0.890. Variable importance in projection values indicated that calycosin, ferulic acid, and puerarin were the primary contributors to quality variations. CONCLUSIONS: The AHP-CRITIC method, coupled with an orthogonal array design, could be used for exploring extraction technology. In addition, the rules governing the transfer of index components from water decoction to extract powder, and subsequently to granules, could be applied for the evaluation and quality assessment of ZTF.

Chemical Composition of Methanol Extracts from Leaves and Flowers of Anemonopsis macrophylla (Ranunculaceae).[Pubmed:38256067]

Int J Mol Sci. 2024 Jan 12;25(2):989.

Anemonopsis Siebold et Zucc. is an unstudied single-species genus belonging to the tribe Cimicifugeae (Ranunculaceae). The only species of this genus-Anemonopsis macrophylla Siebold and Zucc.-is endemic to Japan. There are no data on its chemical composition. This work is the first to determine (with liquid chromatography-high-resolution mass spectrometry, LC-HRMS) the chemical composition of methanol extracts of leaves and flowers of A. macrophylla. More than 100 compounds were identified. In this plant, the classes of substances are coumarins (13 compounds), furocoumarins (3), furochromones (2), phenolic acids (21), flavonoids (27), and fatty acids and their derivatives (15 compounds). Isoferulic Acid (detected in extracts from this plant) brings this species closer to plants of the genus Cimicifuga, one of the few genera containing this acid and ferulic acid at the same time. Isoferulic Acid is regarded as a reference component of a quality indicator of Cimicifuga raw materials. The determined profiles of substances are identical between the leaf and flower methanol extracts. Differences in levels of some identified substances were revealed between the leaf and flower extracts of A. macrophylla; these differences may have a substantial impact on the manifestation of the biological and pharmacological effects of the extracts in question.

Cooking, Digestion, and In Vitro Colonic Fermentation of Nigerian Wholegrains Affect Phenolic Acid Metabolism and Gut Microbiota Composition.[Pubmed:37762412]

Int J Mol Sci. 2023 Sep 14;24(18):14111.

Wholegrains contain both fibre and phenolic acids (PAs), and their gastrointestinal modifications are critical for their bioavailability and bioactivity. We evaluated the modifications on the PA profile and gut microbiota composition of selected Nigerian wholegrains, following cooking and gastrointestinal digestion. Red fonio, red millet, red sorghum, and white corn were cooked, digested, and fermented using an in vitro colonic model. A total of 26 PA derivatives were quantified in soluble and bound fractions using Ultraperformance Liquid Chromatography-Tandem Mass Spectrometry (UPLC-MS/MS) analysis. DNA samples were analysed using 16S rRNA amplicon sequencing to profile the microbiota composition. The results show that cooking and digestion significantly affected the levels of PAs in all grains (p Isoferulic Acid levels correlated negatively with Oscillospira and Ruminococcus (p

Separation and purification of alkaloids and phenolic acids from Phellodendron chinense by pH-zone refining and online-storage inner-recycling counter-current chromatography.[Pubmed:37737621]

J Sep Sci. 2023 Nov;46(22):e2300497.

In this work, eight compounds from Phellodendron chinense were separated and purified by pH-zone refining counter-current chromatography and traditional counter-current chromatography coupled with online-storage inner-recycling counter-current chromatography (IRCCC). The pH-zone-refining mode was adopted for separating 2.0 g of crude extract with the solvent system of chloroform-methanol-water (4:3:3, v/v), in which 10 mM hydrochloric acid and 10 mM triethylamine were added in the stationary and mobile phases, respectively. Meanwhile, traditional counter-current chromatography coupled with online-storage IRCCC separation was performed by the solvent system of n-hexane-ethyl acetate-methanol-water (5:5:2:8, v/v). Finally, eight compounds, including six alkaloids as 6-methylpiperidin-2-one(1), isoplatydesmine(4), berlambine(5), epiberberine(6), palmatine(7), berberine(8) and two phenolic acids as ferulic acid(2), Isoferulic Acid(3), were successfully obtained using these three different CCC modes with the purities over 95.0%.

Scrophularia peyronii Post. from Jordan: Chemical Composition of Essential Oil and Phytochemical Profiling of Crude Extracts and Their In Vitro Antioxidant Activity.[Pubmed:37374186]

Life (Basel). 2023 Jun 16;13(6):1404.

The genus Scrophularia is one of the largest genera belonging to the Scrophulariaceae family. Different members of the genus exhibit an interesting, wide spectrum of bioactivities. Accordingly, the current study aimed to investigate, for the first time, the chemical composition of the essential oil of Scrophularia peyronii Post. from Jordan. Additionally, extracts obtained from the aerial parts with solvents of different polarities were assayed for their phytochemical constituents and in vitro antioxidant activities. The major constituents detected in the essential oil, as revealed by GC/MS analysis, contained mainly Z,Z-farnesyl acetone (11.04%), beta-elemene (6.36%), n-octanal (5.98%), and spathulenol (4.58%). Each of the aqueous methanol (Sp-M) and butanol (Sp-B) extracts contained flavonoids, saponins, anthraquinone, and glycosides. Both extracts were evaluated for their total phenolic content (TPC), total flavonoid content (TFC), and their in vitro antioxidant activity, which were assayed using the DPPH radical scavenging activity and ABTS radical scavenging methods. Additionally, the two extracts were then subjected to LC-ESI-MS/MS for the qualitative determination of their secondary metabolite content, especially in flavonoids and phenolic compounds. The results showed that the Sp-B extract of S. peyronii had the highest contents of both phenolic compounds and flavonoids and showed high radical scavenging activity, as determined by the two assay methods, when compared with the Sp-M extract. The LC-ESI-MS/MS analysis resulted in the detection of 21 compounds, including 8 flavonoids, 6 phenolic acids, 6 iridoids, and 2 acids. Although the majority of compounds were detected in both extracts, it was noticed that scropolioside B, 6'-O-cinnamoylharpagide, Isoferulic Acid, and 6-O-methylcatapol were only detected in the Sp-M fraction.

A Comprehensive Quality Evaluation of Cimicifugae Rhizoma Using UPLC-Q-Orbitrap-MS/MS Coupled with Multivariate Chemometric Methods.[Pubmed:37252833]

J AOAC Int. 2023 Sep 1;106(5):1313-1322.

BACKGROUND: Cimicifugae Rhizoma, known in Chinese as Shengma, is a common medicinal material in traditional Chinese medicine (TCM), mainly used for treating wind-heat headaches, sore throat, uterine prolapse, and other diseases. OBJECTIVES: An approach using a combination of ultra-performance liquid chromatography (UPLC), MS, and multivariate chemometric methods was designed to assess the quality of Cimicifugae Rhizoma. METHODS: All materials were crushed into powder and the powdered sample was dissolved in 70% aqueous methanol for sonication. Chemometric methods, including hierarchical cluster analysis (HCA), principal component analysis (PCA), and orthogonal partial least-squares discriminant analysis (OPLS-DA), were adopted to classify and perform a comprehensive visualization study of Cimicifugae Rhizoma. The unsupervised recognition models of HCA and PCA obtained a preliminary classification and provided a basis for classification. In addition, we constructed a supervised OPLS-DA model and established a prediction set to further validate the explanatory power of the model for the variables and unknown samples. RESULTS: Exploratory research found that the samples were divided into two groups, and the differences were related to appearance traits. The correct classification of the prediction set also demonstrated a strong predictive ability of the models for new samples. Subsequently, six chemical makers were characterized by UPLC-Q-Orbitrap-MS/MS, and the content of four components was determined. The results of the content determination revealed the distribution of representative chemical markers caffeic acid, ferulic acid, Isoferulic Acid, and cimifugin in two classes of samples. CONCLUSIONS: This strategy can provide a reference for assessing the quality of Cimicifugae Rhizoma, which is significant for the clinical practice and QC of Cimicifugae Rhizoma. HIGHLIGHTS: The HCA, PCA and OPLS-DA models visually classify Cimicifugae Rhizoma by appearance traits and obtain the chemical markers that influence the classification. The training and prediction sets were built to demonstrate the accuracy of the classification. Advanced UPLC-Q-Orbitrap-MS/MS technology provides powerful elucidation of critical chemical markers.

Simultaneous determination of multiple components in rat plasma by UHPLC-sMRM for pharmacokinetic studies after oral administration of Qingjin Yiqi Granules.[Pubmed:37124227]

Front Pharmacol. 2023 Apr 13;14:1155973.

As a Traditional Chinese Medicine prescription, Qingjin Yiqi Granules (QJYQ) provides an effective treatment for patients recovering from COVID-19. However, the pharmacokinetics characteristics of the main components of QJYQ in vivo are still unknown. An efficacious ultra-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) was developed and validated for the simultaneous determination of 33 components in rat plasma after oral administration of QJYQ. The plasma samples were precipitated with 400 microL methanol/acetonitrile (1/1, v/v) and analyzed in scheduled multiple reaction monitoring mode. The linear relationship of the 33 components was good (r > 0.9928). The lower limit of quantification for 33 components ranged from 0.4-60.5 ng/mL. The average recoveries and matrix effects of the analytes ranged from 72.9% to 115.0% with RSD of 1.4%-15.0%. All inter-day and intra-day RSDs were within 15.0%. After oral administration (3.15 g/kg), the validated approach was effectively applied to the pharmacokinetics of main components of QJYQ. Finally, fifteen main constituents of QJYQ with large plasma exposure were obtained, including baicalin, wogonoside, wogonin, apigenin-7-O-glucuronide, verbenalin, Isoferulic Acid, hesperidin, liquiritin, harpagide, protocatechuic acid, p-Coumaric acid, ferulic acid, sinapic acid, liquiritin apioside and glycyrrhizic acid. The present research lays a foundation for clarifying the therapeutic material basis of QJYQ and provides a reference for further scientific research and clinical application of QJYQ.

Dipicolinic acid enhances kiwifruit resistance to Botrytis cinerea by promoting phenolics accumulation.[Pubmed:37024430]

Pest Manag Sci. 2023 Sep;79(9):3177-3189.

BACKGROUND: Kiwifruit is highly susceptible to fungal pathogens, such as Botrytis cinerea, which reduce crop production and quality. In this study, dipicolinic acid (DPA), which is one of the main components of Bacillus spores, was evaluated as a new elicitor to enhance kiwifruit resistance to B. cinerea. RESULTS: DPA enhances antioxidant capacity and induces the accumulation of phenolics in B. cinerea-infected 'Xuxiang' kiwifruit. The contents of the main antifungal phenolics in kiwifruit, including caffeic acid, chlorogenic acid and Isoferulic Acid, increased after DPA treatment. DPA enhanced H(2) O(2) levels after 0 and 1 days, which promoted catalase (CAT) and superoxide dismutase (SOD) activities, reducing long-term H(2) O(2) levels. DPA promoted the up-regulation of several kiwifruit defense genes, including CERK1, MPK3, PR1-1, PR1-2, PR5-1 and PR5-2. Furthermore, DPA at 5 mM inhibited B. cinerea symptoms in kiwifruit (95.1% lesion length inhibition) more effectively than the commercial fungicides carbendazim, difenoconazole, prochloraz and thiram. CONCLUSIONS: The antioxidant properties of DPA and the main antifungal phenolics of kiwifruit were examined for the first time. This study uncovers new insights regarding the potential mechanisms used by Bacillus species to induce disease resistance. (c) 2023 Society of Chemical Industry.

Urinary Phenolic Metabolites Associated with Peanut Consumption May Have a Beneficial Impact on Vascular Health Biomarkers.[Pubmed:36978946]

Antioxidants (Basel). 2023 Mar 11;12(3):698.

Phenolic compounds in peanuts may moderate inflammation and endothelial function. Thus, the aim of this study was to evaluate the association of urinary phenolic metabolites (UPMs) with vascular biomarkers after peanut product consumption. A three-arm parallel-group randomized controlled trial was conducted in 63 healthy young adults who consumed 25 g/day of skin roasted peanuts (SRP), 32 g/day of peanut butter (PB), or 32 g/day of a control butter for six months. UPMs were analyzed by liquid chromatography coupled to mass spectrometry. Additionally, urinary eicosanoids, prostacyclin I2 (PGI(2)), and thromboxane A2 (TXA(2)) were determined using two competitive enzyme-linked immunosorbent assay kits. Consumers of SRP and PB presented significantly higher excretion of UPMs (enterodiol glucuronide (p = 0.018 and p = 0.031), 3-hydroxybenzoic acid (p = 0.002 and p < 0.001), vanillic acid sulfate (p = 0.048 and p = 0.006), p-coumaric acid (p = 0.046 and p = 0.016), coumaric acid glucuronide I (p = 0.001 and p = 0.030) and II (p = 0.003 and p = 0.036), and Isoferulic Acid (p = 0.013 and p = 0.015) in comparison with the control group. An improvement in PGI(2) (p = 0.037) levels and the TXA(2):PGI(2) ratio (p = 0.008) was also observed after the peanut interventions compared to the control. Interestingly, UPMs with significantly higher post-intervention levels were correlated with an improvement in vascular biomarkers, lower TXA(2) (r from -0.25 to -0.48, p < 0.050) and TXA(2):PGI(2) ratio (r from -0.25 to -0.43, p < 0.050) and higher PGI(2) (r from 0.24 to 0.36, p < 0.050). These findings suggest that the UPMs with higher excretion after peanut product consumption could have a positive impact on vascular health.

Allelopathic inhibition effects and mechanism of phenolic acids to Microcystis aeruginosa.[Pubmed:36705822]

Environ Sci Pollut Res Int. 2023 Mar;30(15):45388-45397.

Allelochemicals are essential agents for the biological control of harmful blooms. It is crucial to identify efficient algal suppressors and understand their mechanisms. This study reports the inhibition of Microcystis aeruginosa growth by 6 phenolic acids derived from plants' secondary metabolites. The inhibitory effect of phenolic acids was significantly influenced by exposure dose and phenolic acid species. Caffeic acid has the most efficient algal inhibition ability (96 h-EC(50) of 5.8 mg/L). In contrast, the other 5 analogs (cinnamic acid, p-coumaric acid, 3-hydroxycinnamic acid, ferulic acid, and Isoferulic Acid) showed a weak inhibition effect or promotion effect with the exposure dose of 5-100 mg/L. ROS and chlorophyll a content tests combined with metabolomics analysis revealed that caffeic acid could induce the ROS accumulation of M. aeruginosa. They mainly disturbed nucleotide, amino acid, and fatty acid metabolism, leading to the downregulation of most metabolites, including toxins of microcystin LR and cyanopeptolin A, and the precursors of some unpleasant terpenoids. It has been suggested that caffeic acid is an effective agent for controlling M. aeruginosa blooms.

High-Value Compounds and Bioactivity of Rice Bran, Rice Bran Protein: A review.[Pubmed:36578259]

Recent Adv Food Nutr Agric. 2022 Dec 27.

BACKGROUND: Rice bran and rice bran protein are important sources of minerals, energy, and vitamins. Other bioactive compounds are abundantly available to exert therapeutical activity. Health-promoting activities of high-value compounds of rice bran were significant, as observed in recent studies. INTRODUCTION: A variety of bioactive components present in rice bran and rice bran extract are responsible to exhibit therapeutical potential like chemopreventive, cardioprotective, hepatoprotective, immunomodulatory, neuroprotective, and lipid-lowering activity. Several bioactivity representative compounds like gamma-oryzanol, ferulic acid, caffeic acid, tricin, protocatechuic acid, vanillic acid, coumaric acid, phytic acid, Isoferulic Acid, gallic acid, gamma-amino butyric acid, sinapic acid, saturated and unsaturated fatty acids, vitamin E complexes, beta-sitosterol, stigmasterol, campesterol, cyanidin-3-glucoside, peonidin-3-glucoside, quercetin, rutin, kaemferol, beta-carotene, lutein, vitamin B and lycopene are known to display significant health benefits. The bioactive components produced therapeutical effects by regulation of different mechanisms like increasing faecal excretion, reducing oxidative stress, reducing the level of malondialdehyde (MDA), regulation of NF-kb activation, reduction of proinflammatory cytokines production, suppression of SREBP-1, reduction in the expression of anti-apoptotic protein Bcl-2, elevated the expression of pro-apoptotic protein Bax, up-regulating P53 expression and suppressing COX-2. METHODOLOGY: Several research engines like PubMed, google scholar, science direct, etc. were used to collect the data on the mentioned keywords. Recent scientific works were included in this article. CONCLUSION: In this review paper, we profiled the high-value compounds and focused on their antioxidant, anti-hyperlipidemic, antidiabetic, and anticancer activity with their possible mechanism of action.

New substances of Equisetum hyemale L. extracts and their in vivo antitumoral effect against oral squamous cell carcinoma.[Pubmed:36535330]

J Ethnopharmacol. 2023 Mar 1;303:116043.

ETHNOBOTANICAL RELEVANCE: Equisetum hyemale is used in traditional medicine as an anti-inflammatory, antioxidant, diuretic and anticancer agent. Recent studies have observed antiproliferative activity of this species in some tumor cell lines. AIM OF THE STUDY: The aim of this study was to evaluate the antiproliferative activity of the ethanol extract of E. hyemale and its partitions in oral squamous carcinoma cell lines, the death pathways induced by the most active partition, the acute toxicity and therapeutic activity, and the identification of the main compounds. MATERIALS AND METHODS: The ethanol crude extract was prepared from the stems of E. hyemale and partitions were obtained from this extract with n-hexane, dichloromethane and ethyl acetate. Cytotoxicity assays were performed using MTT on human oral tumor lines SCC-9, SCC4 and SCC-25, and normal primary fibroblasts. The main pathways of programmed cell death were analyzed. Acute toxicity in mice was performed using the most active partition, ethyl acetate. Antitumor activity was accessed in xenotransplants grafts of SCC-9 cells in Balb/nude mice. Phytochemical analysis was performed using UHPLC-MS/MS and dereplication was done using Global Natural Product Social Molecular Networking (GNPS) analysis. RESULTS: Ethanol extract, n-hexane and ethyl acetate partitions showed dose-dependent activity and selectivity towards oral tumor cells, with the ethyl acetate being the most bioactive. This medium polarity partition was shown to induce tumor cell death through apoptosis due to the presence of activated caspase 3/7, DNA fragmentation, chromatin condensation and phosphatidylserine exposure. The ethyl acetate partition also produced low toxicity in mice, provoking mild hepatic changes, but without causing necrosis and significantly reduced tumors volume and weight in xenotransplants of SCC-9 cells. Phytochemical analysis allowed identification of kaempferol glycosides and cinnamic acid derivatives previously described for E. hyemale. In addition it was possible to identify 6 new non-glycolyzed flavonoids 5-Hydroxy-3',4',7,8-tetramethoxyflavone (14), 5,4'-Dihydroxy-7,8,3'-trimethoxyflavone (15), 5,7-Dihydroxy-3',4'-dimethoxyflavone (16), 3',4,5,7-Tretramethoxyflavone (17), 5-Hydroxy-3'4',7-trimethoxyflavone (18), and 5,4'-Dihydroxy-3'-7'-dimethoxyflavone (19); besides 5 compounds already determined to be cytotoxic in other species, Isoferulic Acid (1), Ferulic acid (2), Atractylenolide III (6), Dihydroxy-3',4'-dimethoxyflavone (16), and 5-Hydroxy-3'4 ',7-trimethoxyflavone (18). CONCLUSION: The results indicate that the E. hyemale extract and partitions inhibited 3 different cell lines of OSCC in a highly selective nontoxic way by inducing apoptosis of the cells. We identified 6 new non-glycosylated flavonoids and 5 other substances in this species.

Analysis of 12 Chemical Compounds And Pattern Recognition of Different Parts of Angelicae Sinensis Radix by Liquid Chromatography-Tandem Mass Spectrometry And Chemometrics Methods.[Pubmed:36478174]

J Chromatogr Sci. 2023 Feb 3;61(2):103-109.

To evaluate the quality and quantify bioactive constituents in different parts of Angelicae Sinensis Radix, an efficient, high-speed, high-sensitivity high-performance liquid chromatography and triple quadrupole mass spectrometry method was used for simultaneous detection of 12 chemical compounds including L-tryptophan, chlorogenic acid, caffeic acid, ferulic acid, Isoferulic Acid, senkyunolide I, guanosine, proline, L-glutamine, gamma-aminobutyric acid, glutamic acid, and arginine in 52 batches of Angelicae Sinensis Radix from Gansu, China. The established methods were validated by good linearity (R2>/=0.9921), limits of detection (0.0001-0.0156 mug/mL), limits of quantitation (0.0006-0.0781 mug/mL), stability (RSD

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