NCBI Taxonomy: 411249

Luteolin

C15H10O6 (286.0477)

Luteolin is a naturally occurring flavonoid. (PMID:17168665). The flavonoids are polyphenolic compounds found as integral components of the human diet. They are universally present as constituents of flowering plants, particularly of food plants. The flavonoids are phenyl substituted chromones (benzopyran derivatives) consisting of a 15-carbon basic skeleton (C6-C3-C6), composed of a chroman (C6-C3) nucleus (the benzo ring A and the heterocyclic ring C), also shared by the tocopherols, with a phenyl (the aromatic ring B) substitution usually at the 2-position. Different substitutions can typically occur in the rings, A and B. Several plants and spices containing flavonoid derivatives have found application as disease preventive and therapeutic agents in traditional medicine in Asia for thousands of years. The selection of a particular food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. The much lower risk of colon, prostate and breast cancers in Asians, who consume more vegetables, fruits and tea than populations in the Western hemisphere do, raises the question of whether flavonoid components mediate the protective effects of diets rich in these foodstuffs by acting as natural chemopreventive and anticancer agents. An impressive body of information exists on the antitumoral action of plant flavonoids. In vitro work has concentrated on the direct and indirect actions of flavonoids on tumor cells, and has found a variety of anticancer effects such as cell growth and kinase activity inhibition, apoptosis induction, suppression of the secretion of matrix metalloproteinases and of tumor invasive behavior. Furthermore, some studies have reported the impairment of in vivo angiogenesis by dietary flavonoids. Experimental animal studies indicate that certain dietary flavonoids possess antitumoral activity. The hydroxylation pattern of the B ring of the flavones and flavonols, such as luteolin seems to critically influence their activities, especially the inhibition of protein kinase activity and antiproliferation. The different mechanisms underlying the potential anticancer action of plant flavonoids await further elucidation. Certain dietary flavonols and flavones targeting cell surface signal transduction enzymes, such as protein tyrosine and focal adhesion kinases, and the processes of angiogenesis appear to be promising candidates as anticancer agents. Further in vivo studies of these bioactive constituents is deemed necessary in order to develop flavonoid-based anticancer strategies. In view of the increasing interest in the association between dietary flavonoids and cancer initiation and progression, this important field is likely to witness expanded effort and to attract and stimulate further vigorous investigations (PMID:16097445). Luteolin is a tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 4, 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. It has a role as an EC 2.3.1.85 (fatty acid synthase) inhibitor, an antineoplastic agent, a vascular endothelial growth factor receptor antagonist, a plant metabolite, a nephroprotective agent, an angiogenesis inhibitor, a c-Jun N-terminal kinase inhibitor, an anti-inflammatory agent, an apoptosis inducer, a radical scavenger and an immunomodulator. It is a 3-hydroxyflavonoid and a tetrahydroxyflavone. It is a conjugate acid of a luteolin-7-olate. Luteolin is a natural product found in Verbascum lychnitis, Carex fraseriana, and other organisms with data available. Luteolin is a naturally-occurring flavonoid, with potential anti-oxidant, anti-inflammatory, apoptosis-inducing and chemopreventive activities. Upon administration, luteolin scavenges free radicals, protects cells from reactive oxygen species (ROS)-induced damage and induces direct cell cycle arrest and apoptosis in tumor cells. This inhibits tumor cell proliferation and suppresses metastasis. 5,7,3,4-tetrahydroxy-flavone, one of the FLAVONES. See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of). A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 4, 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. Flavone v. widespread in plant world; found especies in celery, peppermint, rosemary, thyme and Queen Annes Lace leaves (wild carrot). Potential nutriceutical. Luteolin is found in many foods, some of which are soy bean, ginger, abalone, and swiss chard. Acquisition and generation of the data is financially supported in part by CREST/JST. IPB_RECORD: 361; CONFIDENCE confident structure CONFIDENCE standard compound; INTERNAL_ID 48 Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3]. Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3].

Cosmosiin

C21H20O10 (432.1056)

Cosmosiin, also known as apigenin 7-O-glucoside or apigetrin, is a member of the class of compounds known as flavonoid-7-O-glycosides. Flavonoid-7-O-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Cosmosiin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cosmosiin can be found in a number of food items, such as common thyme, white lupine, common oregano, and orange mint. Cosmosiin can also be found in dandelion coffee and in Teucrium gnaphalodes (Wikipedia). Cosmosiin can also be found plants such as wild celery and anise. Cosmosiin has been shown to exhibit anti-platelet function (PMID: 21834233). Apigenin 7-O-beta-D-glucoside is a glycosyloxyflavone that is apigenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as a non-steroidal anti-inflammatory drug, a metabolite and an antibacterial agent. It is a beta-D-glucoside, a dihydroxyflavone, a glycosyloxyflavone and a monosaccharide derivative. It is functionally related to an apigenin. It is a conjugate acid of an apigenin 7-O-beta-D-glucoside(1-). It is an enantiomer of an apigenin 7-O-beta-L-glucoside. Cosmosiin is a natural product found in Galeopsis tetrahit, Carex fraseriana, and other organisms with data available. See also: Chamomile (part of). Apiumetrin, also known as 7-O-beta-D-glucosyl-5,7,4-trihydroxyflavone or cosmosiin, is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Apiumetrin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Apiumetrin can be found in wild celery, which makes apiumetrin a potential biomarker for the consumption of this food product. Acquisition and generation of the data is financially supported in part by CREST/JST. Annotation level-1 Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2]. Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2].

Apigenin

C15H10O5 (270.0528)

Apigenin is a trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4, 5 and 7. It induces autophagy in leukaemia cells. It has a role as a metabolite and an antineoplastic agent. It is a conjugate acid of an apigenin-7-olate. Apigenin is a natural product found in Verbascum lychnitis, Carex fraseriana, and other organisms with data available. Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter and the increase in hINV promoter activity. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes. (A7924). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin. (A7925). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis. (A7926). 5,7,4-trihydroxy-flavone, one of the FLAVONES. See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of). Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, and MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes (PMID: 16982614). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin (PMID: 16844095). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis (PMID: 16648565). Flavone found in a wide variety of foodstuffs; buckwheat, cabbage, celeriac, celery, lettuce, oregano, parsley, peppermint, perilla, pummelo juice, thyme, sweet potatoes, green tea and wild carrot [DFC] A trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4, 5 and 7. It induces autophagy in leukaemia cells. CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8558; ORIGINAL_PRECURSOR_SCAN_NO 8556 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5097; ORIGINAL_PRECURSOR_SCAN_NO 5094 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5096; ORIGINAL_PRECURSOR_SCAN_NO 5093 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8561; ORIGINAL_PRECURSOR_SCAN_NO 8559 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5082; ORIGINAL_PRECURSOR_SCAN_NO 5079 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5104; ORIGINAL_PRECURSOR_SCAN_NO 5099 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8572; ORIGINAL_PRECURSOR_SCAN_NO 8570 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8556; ORIGINAL_PRECURSOR_SCAN_NO 8554 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5085; ORIGINAL_PRECURSOR_SCAN_NO 5082 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8554; ORIGINAL_PRECURSOR_SCAN_NO 8550 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8540; ORIGINAL_PRECURSOR_SCAN_NO 8539 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5090; ORIGINAL_PRECURSOR_SCAN_NO 5089 Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CB002_Apigenin_pos_10eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_40eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_20eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_30eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_50eV_CB000005.txt [Raw Data] CB002_Apigenin_neg_40eV_000005.txt [Raw Data] CB002_Apigenin_neg_20eV_000005.txt [Raw Data] CB002_Apigenin_neg_10eV_000005.txt [Raw Data] CB002_Apigenin_neg_50eV_000005.txt CONFIDENCE standard compound; INTERNAL_ID 151 [Raw Data] CB002_Apigenin_neg_30eV_000005.txt CONFIDENCE standard compound; ML_ID 26 Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

Benzoic acid

C7H6O2 (122.0368)

Benzoic acid appears as a white crystalline solid. Slightly soluble in water. The primary hazard is the potential for environmental damage if released. Immediate steps should be taken to limit spread to the environment. Used to make other chemicals, as a food preservative, and for other uses. Benzoic acid is a compound comprising a benzene ring core carrying a carboxylic acid substituent. It has a role as an antimicrobial food preservative, an EC 3.1.1.3 (triacylglycerol lipase) inhibitor, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, a plant metabolite, a human xenobiotic metabolite, an algal metabolite and a drug allergen. It is a conjugate acid of a benzoate. A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid. As the sodium salt form, sodium benzoate is used as a treatment for urea cycle disorders due to its ability to bind amino acids. This leads to excretion of these amino acids and a decrease in ammonia levels. Recent research shows that sodium benzoate may be beneficial as an add-on therapy (1 gram/day) in schizophrenia. Total Positive and Negative Syndrome Scale scores dropped by 21\\\\\% compared to placebo. Benzoic acid is a Nitrogen Binding Agent. The mechanism of action of benzoic acid is as an Ammonium Ion Binding Activity. Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Appreciable amounts have been found in most berries (around 0.05\\\\\%). Cranberries contain as much as 300-1300 mg free benzoic acid per kg fruit. Benzoic acid is a fungistatic compound that is widely used as a food preservative. It often is conjugated to glycine in the liver and excreted as hippuric acid. Benzoic acid is a byproduct of phenylalanine metabolism in bacteria. It is also produced when gut bacteria process polyphenols (from ingested fruits or beverages). A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid. See also: Salicylic Acid (active moiety of); Benzoyl Peroxide (active moiety of); Sodium Benzoate (active moiety of) ... View More ... Widespread in plants especies in essential oils and fruits, mostly in esterified formand is also present in butter, cooked meats, pork fat, white wine, black and green tea, mushroom and Bourbon vanilla. It is used in foodstuffs as antimicrobial and flavouring agent and as preservative. In practical food preservation, the Na salt of benzoic acid is the most widely used form (see MDQ71-S). The antimicrobial activity comprises a wide range of microorganisms, particularly yeasts and moulds. Undissociated benzoic acid is more effective than dissociated, thus the preservative action is more efficient in acidic foodstuffs. Typical usage levels are 500-2000 ppm. Benzoic acid is found in many foods, some of which are animal foods, common grape, lovage, and fruits. Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Appreciable amounts have been found in most berries (around 0.05\\\\\%). Cranberries contain as much as 300-1300 mg free benzoic acid per kg fruit. Benzoic acid is a fungistatic compound that is widely used as a food preservative. It often is conjugated to glycine in the liver and excreted as hippuric acid. Benzoic acid is a byproduct of phenylalanine metabolism in bacteria. It is also produced when gut bacteria process polyphenols (from ingested fruits or beverages). It can be found in Serratia (PMID:23061754). Benzoic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=65-85-0 (retrieved 2024-06-28) (CAS RN: 65-85-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Benzoic acid is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products. It acts as preservatives through inhibiting both bacteria and fungi. Benzoic acid is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products. It acts as preservatives through inhibiting both bacteria and fungi.

4-Hydroxybenzoic acid

C7H6O3 (138.0317)

4-Hydroxybenzoic acid, also known as p-hydroxybenzoate or 4-carboxyphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 4-Hydroxybenzoic acid is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. It is a nutty and phenolic tasting compound. 4-Hydroxybenzoic acid exists in all living species, ranging from bacteria to plants to humans. 4-Hydroxybenzoic acid can be found naturally in coconut. It is one of the main catechins metabolites found in humans after consumption of green tea infusions. It is also found in wine, in vanilla, in A√ßa√≠ oil, obtained from the fruit of the a√ßa√≠ palm (Euterpe oleracea), at relatively high concetrations (892¬±52 mg/kg). It is also found in cloudy olive oil and in the edible mushroom Russula virescens. It has been detected in red huckleberries, rabbiteye blueberries, and corianders and in a lower concentration in olives, red raspberries, and almonds. In humans, 4-hydroxybenzoic acid is involved in ubiquinone biosynthesis. In particular, the enzyme 4-hydroxybenzoate polyprenyltransferase uses a polyprenyl diphosphate and 4-hydroxybenzoate to produce diphosphate and 4-hydroxy-3-polyprenylbenzoate. This enzyme participates in ubiquinone biosynthesis. 4-Hydroxybenzoic acid can be biosynthesized by the enzyme Chorismate lyase. Chorismate lyase is an enzyme that transforms chorismate into 4-hydroxybenzoate and pyruvate. This enzyme catalyses the first step in ubiquinone biosynthesis in Escherichia coli and other Gram-negative bacteria. 4-Hydroxybenzoate is an intermediate in many enzyme-mediated reactions in microbes. For instance, the enzyme 4-hydroxybenzaldehyde dehydrogenase uses 4-hydroxybenzaldehyde, NAD+ and H2O to produce 4-hydroxybenzoate, NADH and H+. This enzyme participates in toluene and xylene degradation in bacteria such as Pseudomonas mendocina. 4-hydroxybenzaldehyde dehydrogenase is also found in carrots. The enzyme 4-hydroxybenzoate 1-hydroxylase transforms 4-hydroxybenzoate, NAD(P)H, 2 H+ and O2 into hydroquinone, NAD(P)+, H2O and CO2. This enzyme participates in 2,4-dichlorobenzoate degradation and is found in Candida parapsilosis. The enzyme 4-hydroxybenzoate 3-monooxygenase transforms 4-hydroxybenzoate, NADPH, H+ and O2 into protocatechuate, NADP+ and H2O. This enzyme participates in benzoate degradation via hydroxylation and 2,4-dichlorobenzoate degradation and is found in Pseudomonas putida and Pseudomonas fluorescens. 4-Hydroxybenzoic acid is a popular antioxidant in part because of its low toxicity. 4-Hydroxybenzoic acid has estrogenic activity both in vitro and in vivo (PMID 9417843). Isolated from many plants, free and combined. Alkyl esters of 4-hydroxybenzoic acid (see below) are used as food and cosmetic preservatives, mainly in their Na salt form, which makes them more water soluble. They are active at low concentrations and more pH-independent than the commonly used Benzoic acid DVN38-Z and 2,4-Hexadienoic acid GMZ10-P. The taste is more detectable than for those preservatives. Effectiveness increases with chain length of the alcohol, but for some microorganisms this reduces cell permeability and thus counteracts the increased efficiency. 4-Hydroxybenzoic acid is found in many foods, some of which are chicory, corn, rye, and black huckleberry. 4-hydroxybenzoic acid is a monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. It has a role as a plant metabolite and an algal metabolite. It is a conjugate acid of a 4-hydroxybenzoate. 4-Hydroxybenzoic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). See also: Vaccinium myrtillus Leaf (part of); Galium aparine whole (part of); Menyanthes trifoliata leaf (part of) ... View More ... A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. 4-Hydroxybenzoic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=99-96-7 (retrieved 2024-07-01) (CAS RN: 99-96-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

Quercetin

C15H10O7 (302.0427)

Quercetin appears as yellow needles or yellow powder. Converts to anhydrous form at 203-207 °F. Alcoholic solutions taste very bitter. (NTP, 1992) Quercetin is a pentahydroxyflavone having the five hydroxy groups placed at the 3-, 3-, 4-, 5- and 7-positions. It is one of the most abundant flavonoids in edible vegetables, fruit and wine. It has a role as an antibacterial agent, an antioxidant, a protein kinase inhibitor, an antineoplastic agent, an EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor, a plant metabolite, a phytoestrogen, a radical scavenger, a chelator, an Aurora kinase inhibitor and a geroprotector. It is a pentahydroxyflavone and a 7-hydroxyflavonol. It is a conjugate acid of a quercetin-7-olate. Quercetin is a flavonol widely distributed in plants. It is an antioxidant, like many other phenolic heterocyclic compounds. Glycosylated forms include RUTIN and quercetrin. Quercetin is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Quercetin is a flavonoid found in many foods and herbs and is a regular component of a normal diet. Extracts of quercetin have been used to treat or prevent diverse conditions including cardiovascular disease, hypercholesterolemia, rheumatic diseases, infections and cancer but have not been shown to be effective in clinical trials for any medical condition. Quercetin as a nutritional supplement is well tolerated and has not been linked to serum enzyme elevations or to episodes of clinically apparent liver injury. Quercetin is a natural product found in Lotus ucrainicus, Visnea mocanera, and other organisms with data available. Quercetin is a polyphenolic flavonoid with potential chemopreventive activity. Quercetin, ubiquitous in plant food sources and a major bioflavonoid in the human diet, may produce antiproliferative effects resulting from the modulation of either EGFR or estrogen-receptor mediated signal transduction pathways. Although the mechanism of action of action is not fully known, the following effects have been described with this agent in vitro: decreased expression of mutant p53 protein and p21-ras oncogene, induction of cell cycle arrest at the G1 phase and inhibition of heat shock protein synthesis. This compound also demonstrates synergy and reversal of the multidrug resistance phenotype, when combined with chemotherapeutic drugs, in vitro. Quercetin also produces anti-inflammatory and anti-allergy effects mediated through the inhibition of the lipoxygenase and cyclooxygenase pathways, thereby preventing the production of pro-inflammatory mediators. Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. Quercetin itself (aglycone quercetin), as opposed to quercetin glycosides, is not a normal dietary component. Quercitin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. Quercetin has neither been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, the interest in dietary flavonoids has grown after the publication of several epidemiological studies showing an inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adju... Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. Quercetin itself (aglycone quercetin), as opposed to quercetin glycosides, is not a normal dietary component. Quercetin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. Quercetin has neither been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, the interest in dietary flavonoids has grown after the publication of several epidemiological studies showing an inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adjustment for known risk factors and other dietary components. A limited number of intervention studies with flavonoids and flavonoid containing foods and extracts has been performed in several pathological conditions (PMID:17015250). Quercetin is isolated from many plants, especially fruits, such as Helichrysum, Euphorbia and Karwinskia spp. Present in the Solanaceae, Rhamnaceae, Passifloraceae and many other families. For example detected in almost all studied Umbelliferae. Nutriceutical with antiinflammatory props. and a positive influence on the blood lipid profile. Found in a wide variety of foods especially apples, bee pollen, blackcurrants, capers, cocoa, cranberries, dock leaves, elderberries, fennel, lovage, red onions, ancho peppers, dill weed and tarragon. A pentahydroxyflavone having the five hydroxy groups placed at the 3-, 3-, 4-, 5- and 7-positions. It is one of the most abundant flavonoids in edible vegetables, fruit and wine. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4014; ORIGINAL_PRECURSOR_SCAN_NO 4012 INTERNAL_ID 298; CONFIDENCE standard compound; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4011; ORIGINAL_PRECURSOR_SCAN_NO 4010 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4019; ORIGINAL_PRECURSOR_SCAN_NO 4018 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4017; ORIGINAL_PRECURSOR_SCAN_NO 4016 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4011; ORIGINAL_PRECURSOR_SCAN_NO 4010 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4096; ORIGINAL_PRECURSOR_SCAN_NO 4094 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4024; ORIGINAL_PRECURSOR_SCAN_NO 4023 Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CB109_Quercetin_pos_30eV_CB000041.txt IPB_RECORD: 1761; CONFIDENCE confident structure [Raw Data] CB109_Quercetin_pos_10eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_20eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_40eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_50eV_CB000041.txt IPB_RECORD: 161; CONFIDENCE confident structure [Raw Data] CB109_Quercetin_neg_40eV_000027.txt [Raw Data] CB109_Quercetin_neg_50eV_000027.txt [Raw Data] CB109_Quercetin_neg_20eV_000027.txt [Raw Data] CB109_Quercetin_neg_30eV_000027.txt [Raw Data] CB109_Quercetin_neg_10eV_000027.txt CONFIDENCE standard compound; INTERNAL_ID 124 CONFIDENCE standard compound; ML_ID 54 Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1]. Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1].

Shikonin

C16H16O5 (288.0998)

Shikonin is a hydroxy-1,4-naphthoquinone. Shikonin is a natural product found in Echium plantagineum, Arnebia hispidissima, and other organisms with data available. See also: Arnebia guttata root (part of); Arnebia euchroma root (part of); Lithospermum erythrorhizon root (part of). D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents Shikonin is a major component of a Chinese herbal medicine named zicao. Shikonin is a potent TMEM16A chloride channel inhibitor with an IC50 of 6.5 μM[1]. Shikonin is a specific pyruvate kinase M2 (PKM2) inhibitor[2] and can also inhibit TNF-α and NF-κB pathway[3]. Shikonin decreases exosome secretion through the inhibition of glycolysis[4]. Shikonin inhibits AIM2 inflammasome activation[7]. Shikonin is a major component of a Chinese herbal medicine named zicao. Shikonin is a potent TMEM16A chloride channel inhibitor with an IC50 of 6.5 μM[1]. Shikonin is a specific pyruvate kinase M2 (PKM2) inhibitor[2] and can also inhibit TNF-α and NF-κB pathway[3]. Shikonin decreases exosome secretion through the inhibition of glycolysis[4]. Shikonin inhibits AIM2 inflammasome activation[7].

Acetylshikonin

C18H18O6 (330.1103)

Acetylshikonin is an acetate ester and a hydroxy-1,4-naphthoquinone. Acetylshikonin is a natural product found in Echium plantagineum, Lithospermum erythrorhizon, and other organisms with data available. Acetylshikonin, derived from the root of Lithospermum erythrorhizon, has anti-cancer and antiinflammation activity. Acetylshikonin is a non-selective cytochrome P450 inhibitor against all P450s (IC50 values range from 1.4-4.0 μM). Acetylshikonin is an AChE inhibitor and exhibits potent antiapoptosis activity[1][2][3]. Acetylshikonin, derived from the root of Lithospermum erythrorhizon, has anti-cancer and antiinflammation activity. Acetylshikonin is a non-selective cytochrome P450 inhibitor against all P450s (IC50 values range from 1.4-4.0 μM). Acetylshikonin is an AChE inhibitor and exhibits potent antiapoptosis activity[1][2][3].

beta,beta-Dimethylacrylshikonin

C21H22O6 (370.1416)

Dmask is a natural product found in Arnebia hispidissima with data available. Beta,beta-Dimethylacrylshikonin is a hydroxy-1,4-naphthoquinone. beta,beta-Dimethylacrylshikonin is a natural product found in Alkanna cappadocica, Lithospermum erythrorhizon, and other organisms with data available. (Rac)-Arnebin 1 ((Rac)-β,β-Dimethylacrylalkannin) is the racemate of β,β-Dimethylacrylalkannin and/or β,β-Dimethylacrylshikonin. β,β-Dimethylacrylalkannin and β,β-Dimethylacrylshikonin are napthoquinones isolated from Arnebia nobilis. β,β-Dimethylacrylshikonin has anti-tumor activity[1]. (Rac)-Arnebin 1 ((Rac)-β,β-Dimethylacrylalkannin) is the racemate of β,β-Dimethylacrylalkannin and/or β,β-Dimethylacrylshikonin. β,β-Dimethylacrylalkannin and β,β-Dimethylacrylshikonin are napthoquinones isolated from Arnebia nobilis. β,β-Dimethylacrylshikonin has anti-tumor activity[1]. (Rac)-Arnebin 1 ((Rac)-β,β-Dimethylacrylalkannin) is the racemate of β,β-Dimethylacrylalkannin and/or β,β-Dimethylacrylshikonin. β,β-Dimethylacrylalkannin and β,β-Dimethylacrylshikonin are napthoquinones isolated from Arnebia nobilis. β,β-Dimethylacrylshikonin has anti-tumor activity[1]. β,β-Dimethylacrylalkannin (Arnebin 1) is a napthoquinone isolated from Alkanna cappadocica , increases collagen and involucrin content in skin cells[1]. β,β-Dimethylacrylalkannin (Arnebin 1) is a napthoquinone isolated from Alkanna cappadocica , increases collagen and involucrin content in skin cells[1]. β,β-Dimethylacrylalkannin (Arnebin 1) is a napthoquinone isolated from Alkanna cappadocica , increases collagen and involucrin content in skin cells[1]. β,β-Dimethylacrylshikonin (Isoarnebin I) is a naphthoquinone derivative isolated from Lithospermum erythrorhizon Sieb. et Zucc. , promotes angiogenesis by inducing eNOS, VEGF and HIF-1α expression through the PI3K-dependent pathway.β,β-Dimethylacrylshikonin has anti-tumor activity[1]. β,β-Dimethylacrylshikonin (Isoarnebin I) is a naphthoquinone derivative isolated from Lithospermum erythrorhizon Sieb. et Zucc. , promotes angiogenesis by inducing eNOS, VEGF and HIF-1α expression through the PI3K-dependent pathway.β,β-Dimethylacrylshikonin has anti-tumor activity[1]. β,β-Dimethylacrylshikonin (Isoarnebin I) is a naphthoquinone derivative isolated from Lithospermum erythrorhizon Sieb. et Zucc. , promotes angiogenesis by inducing eNOS, VEGF and HIF-1α expression through the PI3K-dependent pathway.β,β-Dimethylacrylshikonin has anti-tumor activity[1].

Chrysoeriol

C16H12O6 (300.0634)

Chrysoeriol, also known as 3-O-methylluteolin, belongs to the class of organic compounds known as 3-O-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. Thus, chrysoeriol is considered to be a flavonoid lipid molecule. Chrysoeriol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Chrysoeriol is a bitter-tasting compound. Outside of the human body, chrysoeriol has been detected, but not quantified in, several different foods, such as wild celeries, ryes, hard wheat, alfalfa, and triticales. This could make chrysoeriol a potential biomarker for the consumption of these foods. 4,5,7-trihydroxy-3-methoxyflavone is the 3-O-methyl derivative of luteolin. It has a role as an antineoplastic agent, an antioxidant and a metabolite. It is a trihydroxyflavone and a monomethoxyflavone. It is functionally related to a luteolin. It is a conjugate acid of a 4,5-dihydroxy-3-methoxyflavon-7-olate(1-). Chrysoeriol is a natural product found in Haplophyllum ramosissimum, Myoporum tenuifolium, and other organisms with data available. See also: Acai (part of); Acai fruit pulp (part of). Widespread flavone. Chrysoeriol is found in many foods, some of which are peanut, german camomile, tarragon, and alfalfa. The 3-O-methyl derivative of luteolin. Chrysoeriol, a natural flavonoid extracted from the tropical plant Coronopus didymus, exhibits potent antioxidant activity. Chrysoeriol shows significant inhibition of lipid peroxidation[1]. Chrysoeriol, a natural flavonoid extracted from the tropical plant Coronopus didymus, exhibits potent antioxidant activity. Chrysoeriol shows significant inhibition of lipid peroxidation[1].

Uplandicine

C17H27NO7 (357.1787)

7-Acetyllycopsamine

C17H27NO6 (341.1838)

7-acetyllycopsamine is soluble (in water) and a very weakly acidic compound (based on its pKa). 7-acetyllycopsamine can be found in borage, which makes 7-acetyllycopsamine a potential biomarker for the consumption of this food product. CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2277

Acetyllycopsamine

C17H27NO6 (341.1838)

Acetyllycopsamine is soluble (in water) and a very weakly acidic compound (based on its pKa). Acetyllycopsamine can be found in borage, which makes acetyllycopsamine a potential biomarker for the consumption of this food product.

Anthemoside

C21H20O10 (432.1056)

Constituent of Anthemis nobilis (Roman chamomile). Anthemoside is found in herbs and spices.

betuletol

C17H14O7 (330.0739)

Apigenin

C15H10O5 (270.0528)

Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.061 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.062 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.058 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.059 Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

Luteolin

C15H10O6 (286.0477)

Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.976 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.975 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.968 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.971 Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3]. Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3].

Quercetin

C15H10O7 (302.0427)

Annotation level-1 COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials relative retention time with respect to 9-anthracene Carboxylic Acid is 0.898 D020011 - Protective Agents > D000975 - Antioxidants Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 0.902 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 1981; CONFIDENCE confident structure IPB_RECORD: 3301; CONFIDENCE confident structure IPB_RECORD: 3283; CONFIDENCE confident structure Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1]. Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1].

Onosmin A

C15H15NO2 (241.1103)

An aminobenzoic acid that is anthranilic acid in which one of the hydrogens of the amino group is replaced by a 4-methylbenzyl group. Isolated from Onosma hispida, it exhibits inhibitory activity against lipoxygenase.

Eupalitin

C17H14O7 (330.0739)

Onosmin B

C16H17NO2 (255.1259)

A benzoate ester obtained by the fromal condensation of the carboxy group of onosmin A with methanol. Isolated from Onosma hispida, it exhibits inhibitory activity against lipoxygenase.

Acetyllycopsamine

C17H27NO6 (341.1838)

Acetyllycopsamine is a member of pyrrolizines. 7-Acetyllycopsamine is a natural product found in Echium horridum, Amsinckia menziesii, and other organisms with data available. See also: Comfrey Leaf (part of).

Chrysoeriol

C16H12O6 (300.0634)

Chrysoeriol, a natural flavonoid extracted from the tropical plant Coronopus didymus, exhibits potent antioxidant activity. Chrysoeriol shows significant inhibition of lipid peroxidation[1]. Chrysoeriol, a natural flavonoid extracted from the tropical plant Coronopus didymus, exhibits potent antioxidant activity. Chrysoeriol shows significant inhibition of lipid peroxidation[1].

Chryseriol

C16H12O6 (300.0634)

relative retention time with respect to 9-anthracene Carboxylic Acid is 1.094 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.096 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.093 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.091 Chrysoeriol, a natural flavonoid extracted from the tropical plant Coronopus didymus, exhibits potent antioxidant activity. Chrysoeriol shows significant inhibition of lipid peroxidation[1]. Chrysoeriol, a natural flavonoid extracted from the tropical plant Coronopus didymus, exhibits potent antioxidant activity. Chrysoeriol shows significant inhibition of lipid peroxidation[1].

4-hydroxybenzoate

C7H6O3 (138.0317)

4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

Apigetrin

C21H20O10 (432.1056)

Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2]. Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2].

Benzoic Acid

C7H6O2 (122.0368)

Benzoic acid is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products. It acts as preservatives through inhibiting both bacteria and fungi. Benzoic acid is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products. It acts as preservatives through inhibiting both bacteria and fungi.

p-Hydroxybenzoic acid

C7H6O3 (138.0317)

4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

2-[(4-methylphenyl)methylamino]benzoic Acid

C15H15NO2 (241.1103)

cosmetin

C21H20O10 (432.1056)

Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2]. Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2].

Versulin

C15H10O5 (270.0528)

Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

Quertin

C15H10O7 (302.0427)

COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1]. Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1].

Isoarnebin I

C21H22O6 (370.1416)

Beta,beta-Dimethylacrylshikonin is a hydroxy-1,4-naphthoquinone. beta,beta-Dimethylacrylshikonin is a natural product found in Alkanna cappadocica, Lithospermum erythrorhizon, and other organisms with data available. β,β-Dimethylacrylshikonin (Isoarnebin I) is a naphthoquinone derivative isolated from Lithospermum erythrorhizon Sieb. et Zucc. , promotes angiogenesis by inducing eNOS, VEGF and HIF-1α expression through the PI3K-dependent pathway.β,β-Dimethylacrylshikonin has anti-tumor activity[1]. β,β-Dimethylacrylshikonin (Isoarnebin I) is a naphthoquinone derivative isolated from Lithospermum erythrorhizon Sieb. et Zucc. , promotes angiogenesis by inducing eNOS, VEGF and HIF-1α expression through the PI3K-dependent pathway.β,β-Dimethylacrylshikonin has anti-tumor activity[1]. β,β-Dimethylacrylshikonin (Isoarnebin I) is a naphthoquinone derivative isolated from Lithospermum erythrorhizon Sieb. et Zucc. , promotes angiogenesis by inducing eNOS, VEGF and HIF-1α expression through the PI3K-dependent pathway.β,β-Dimethylacrylshikonin has anti-tumor activity[1].

(2s)-5-hydroxy-2-(2-hydroxy-4,5-dimethoxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one

C18H18O7 (346.1052)

8-hydroxy-6-(1-hydroxy-4-methylpent-3-en-1-yl)-5-methoxynaphthalene-1,4-dione

C17H18O5 (302.1154)

5-hydroxy-2-(2-hydroxy-5-methoxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one

C17H16O6 (316.0947)

apigetrin

C21H20O10 (432.1056)

{"Ingredient_id": "HBIN016480","Ingredient_name": "apigetrin","Alias": "CHEMBL487995; SR-05000002285; Galactosyl-7-apigenin; EINECS 209-430-5; 5-Hydroxy-2-(4-hydroxyphenyl)-7-(4,5,6-trihydroxy-3-(hydroxymethyl)(2-oxanyloxy))-4H-chromen-4-one; Cosemetin; 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one; COSMOSIIN; 4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)- (9CI); Apigenin, 7-beta-D-glucopyranoside; Apigenin 7-O-beta-D-glucopyranoside; 7-(beta-D-Glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; Cosmosiine; 7-O-(beta-D-Glucosyl)apigenin; Thalictiin; SR-05000002285-3; A831652; Cosmosioside; 23598-21-2; NSC 407303; Apigetrin; NCGC00163513-01; CCG-208379; 62532-75-6; 5-hydroxy-2-(4-hydroxyphenyl)-7-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-1-benzopyran-4-one; UNII-7OF2S66PCH; SR-05000002285-2; 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one; AC1NUZ8G; Apigenin, 7-beta-D-galactopyranoside; 7-[(2S,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-2-(4-hydroxyphenyl)-5-oxidanyl-chromen-4-one; 7OF2S66PCH; Cosmosiin (8CI)","Ingredient_formula": "C21H20O10","Ingredient_Smile": "C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O","Ingredient_weight": "432.4 g/mol","OB_score": "NA","CAS_id": "NA","SymMap_id": "SMIT19095","TCMID_id": "30618","TCMSP_id": "NA","TCM_ID_id": "21625","PubChem_id": "12304093","DrugBank_id": "NA"}

(2e)-3-[4,5-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)cyclohexa-1,3-dien-1-yl]prop-2-enoic acid

C16H16O6 (304.0947)

(1r)-7-(hydroxymethyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl acetate

C10H15NO3 (197.1052)

[(7r,7ar)-7-hydroxy-5,6,7,7a-tetrahydro-3h-pyrrolizin-1-yl]methyl 2-[(1r)-1-(acetyloxy)ethyl]-2-hydroxy-3-methylbutanoate

C17H27NO6 (341.1838)

(1r,7ar)-7-({[(2r)-2,3-dihydroxy-2-(1-hydroxyethyl)-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl 3-methylbut-2-enoate

C20H31NO7 (397.21)

(1s,3as,5ar,9ar,9br,11as)-1-[(3s,5r,6s)-5,6-dihydroxy-7,7-dimethyloxepan-3-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one

C30H48O4 (472.3552)

(2s)-5-hydroxy-2-(2-hydroxy-5-methoxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one

C17H16O6 (316.0947)

(1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbut-2-enoate

C21H22O6 (370.1416)

(7as)-5,6,7,7a-tetrahydro-3h-pyrrolizin-1-ylmethyl (2e)-but-2-enoate

C12H17NO2 (207.1259)

1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-hydroxy-3-methylbutanoate

C21H24O7 (388.1522)

[(7r,7ar)-7-hydroxy-5,6,7,7a-tetrahydro-3h-pyrrolizin-1-yl]methyl (2r)-2,3-dihydroxy-2-[(1r)-1-hydroxyethyl]-3-methylbutanoate

C15H25NO6 (315.1682)

(1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-hydroxy-3-methylbutanoate

C21H24O7 (388.1522)

1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbutanoate

C21H24O6 (372.1573)

(1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl acetate

C18H18O6 (330.1103)

5-hydroxy-2-(2-hydroxy-4,5-dimethoxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one

C18H18O7 (346.1052)