NCBI Taxonomy: 326831

Pedicularis longiflora (ncbi_taxid: 326831)

found 116 associated metabolites at species taxonomy rank level.

Ancestor: Pedicularis

Child Taxonomies: Pedicularis longiflora var. tubiformis

Luteolin

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

C15H10O6 (286.047736)


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].

   

Loganic_acid

(1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

C16H24O10 (376.13694039999996)


Loganic acid is a cyclopentapyran that is 1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid substituted at positions 1, 6 and 7 by beta-D-glucosyloxy, hydroxy and methyl groups respectively It has a role as a plant metabolite. It is a cyclopentapyran, an alpha,beta-unsaturated monocarboxylic acid and a glucoside. It is a conjugate acid of a loganate. Loganic acid is a natural product found in Strychnos axillaris, Strychnos cocculoides, and other organisms with data available. A cyclopentapyran that is 1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid substituted at positions 1, 6 and 7 by beta-D-glucosyloxy, hydroxy and methyl groups respectively KEIO_ID L043 Loganic acid is an iridoid isolated from cornelian cherry fruits. Loganic acid can modulate diet-induced atherosclerosis and redox status. Loganic acid has strong free radical scavenging activity and remarkable cyto-protective effect against heavy metal mediated toxicity[1][2]. Loganic acid is an iridoid isolated from cornelian cherry fruits. Loganic acid can modulate diet-induced atherosclerosis and redox status. Loganic acid has strong free radical scavenging activity and remarkable cyto-protective effect against heavy metal mediated toxicity[1][2].

   

Aucubin

(2S,3R,4S,5S,6R)-2-(((1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

C15H22O9 (346.1263762)


Aucubin is found in common verbena. Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan-[C]-pyran skeleton. Iridoids can consist of ten, nine, or rarely eight carbons in which C11 is more frequently missing than C10. Aucubin has 10 carbons with the C11 carbon missing. The stereochemical configurations at C5 and C9 lead to cis fused rings, which are common to all iridoids containing carbocylclic- or seco-skeleton in non-rearranged form. Oxidative cleavage at C7-C8 bond affords secoiridoids. The last steps in the biosynthesis of iridoids usually consist of O-glycosylation and O-alkylation. Aucubin, a glycoside iridoid, has an O-linked glucose moiety. Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Irioids decrease the growth rates of many generalist herbivores. Aucubin is found in the leaves of Aucuba japonica (Cornaceae), Eucommia ulmoides (Eucommiaceae), and Plantago asiatic (Plantaginaceae), etc, plants used in traditional Chinese and folk medicine. Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally. Geranyl pyrophosphate is the precursor for iridoids. Geranyl phosphate is generated through the mevalonate pathway or the methylerythritol phosphate pathway. The initial steps of the pathway involve the fusion of three molecules of acetyl-CoA to produce the C6 compound 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA). HMG-CoA is then reduced in two steps by the enzyme HMG-CoA reductase. The resulting mevalonate is then sequentially phosphorylated by two separate kinases, mevalonate kinase and phosphomevalonate kinase, to form 5-pyrophosphomevalonate. Phosphosphomevalonate decarboxylase through a concerted decarboxylation reaction affords isopentenyl pyrophosphate (IPP). IPP is the basic C5 building block that is added to prenyl phosphate cosubstrates to form longer chains. IPP is isomerized to the allylic ester dimethylallyl pyrophosphate (DMAPP) by IPP isomerase. Through a multistep process, including the dephosphorylation DMAPP, IPP and DMAPP are combinded to from the C10 compound geranyl pyrophosphate (GPP). Geranyl pyrophosphate is a major branch point for terpenoid synthesis. The cyclizaton reaction to form the iridoid pyrane ring may result from one of two routes: route 1 - a hydride nucleophillic attack on C1 will lead to 1-O-carbonyl atom attack on C3, yielding the lactone ring; route 2 - loss of proton from carbon 4 leads to the formation of a double bond C3-C4; consequently the 3-0-carbonyl atom will attach to C1 Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan-[C]-pyran skeleton. Iridoids can consist of ten, nine, or rarely eight carbons in which C11 is more frequently missing than C10. Aucubin has 10 carbons with the C11 carbon missing. The stereochemical configurations at C5 and C9 lead to cis fused rings, which are common to all iridoids containing carbocylclic- or seco-skeleton in non-rearranged form. Oxidative cleavage at C7-C8 bond affords secoiridoids. The last steps in the biosynthesis of iridoids usually consist of O-glycosylation and O-alkylation. Aucubin, a glycoside iridoid, has an O-linked glucose moiety.; Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Irioids decrease the growth rates of many generalist herbivores. Aucubin is found in the leaves of Aucuba japonica (Cornaceae), Eucommia ulmoides (Eucommiaceae), and Plantago asiatic (Plantaginaceae), etc, plants used in traditional Chinese and folk medicine. Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally.; Geranyl pyrophosphate is the precursor for iridoids. Geranyl phosphate is generated through the mevalonate pathway or the methylerythritol phosphate pathway. The initial steps of the pathway involve the fusion of three molecules of acetyl-CoA to produce the C6 compound 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA). HMG-CoA is then reduced in two steps by the enzyme HMG-CoA reductase. The resulting mevalonate is then sequentially phosphorylated by two separate kinases, mevalonate kinase and phosphomevalonate kinase, to form 5-pyrophosphomevalonate. Phosphosphomevalonate decarboxylase through a concerted decarboxylation reaction affords isopentenyl pyrophosphate (IPP). IPP is the basic C5 building block that is added to prenyl phosphate cosubstrates to form longer chains. IPP is isomerized to the allylic ester dimethylallyl pyrophosphate (DMAPP) by IPP isomerase. Through a multistep process, including the dephosphorylation DMAPP, IPP and DMAPP are combinded to from the C10 compound geranyl pyrophosphate (GPP). Geranyl pyrophosphate is a major branch point for terpenoid synthesis.; The cyclizaton reaction to form the iridoid pyrane ring may result from one of two routes: route 1 - a hydride nucleophillic attack on C1 will lead to 1-O-carbonyl atom attack on C3, yielding the lactone ring; route 2 - loss of proton from carbon 4 leads to the formation of a double bond C3-C4; consequently the 3-0-carbonyl atom will attach to C1. Aucubin is an organic molecular entity. It has a role as a metabolite. Aucubin is a natural product found in Verbascum lychnitis, Plantago media, and other organisms with data available. See also: Chaste tree fruit (part of); Rehmannia glutinosa Root (part of); Plantago ovata seed (part of). Aucubin, an iridoid glucoside, is isolated from Plantago asiatica, Eucommia ulmoides, the leaves of Aucuba japonica and more recently from butterfly larva. Aucubin has many biological activities, such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective effects[1][2][3]. Aucubin, an iridoid glucoside, is isolated from Plantago asiatica, Eucommia ulmoides, the leaves of Aucuba japonica and more recently from butterfly larva. Aucubin has many biological activities, such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective effects[1][2][3].

   

Apigenin

5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

C15H10O5 (270.052821)


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.

   

Tricin

5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-1-benzopyran-4-one

C17H14O7 (330.0739494)


[Raw Data] CBA24_Tricin_neg_50eV_1-6_01_1424.txt [Raw Data] CBA24_Tricin_pos_50eV_1-6_01_1397.txt [Raw Data] CBA24_Tricin_neg_10eV_1-6_01_1368.txt [Raw Data] CBA24_Tricin_pos_40eV_1-6_01_1396.txt [Raw Data] CBA24_Tricin_pos_20eV_1-6_01_1394.txt [Raw Data] CBA24_Tricin_neg_30eV_1-6_01_1422.txt [Raw Data] CBA24_Tricin_neg_20eV_1-6_01_1421.txt [Raw Data] CBA24_Tricin_pos_10eV_1-6_01_1357.txt [Raw Data] CBA24_Tricin_pos_30eV_1-6_01_1488.txt [Raw Data] CBA24_Tricin_neg_40eV_1-6_01_1423.txt Tricin is a natural flavonoid present in large amounts in Triticum aestivum. Tricin can inhibit human cytomegalovirus (HCMV) replication by inhibiting CDK9. Tricin inhibits the proliferation and invasion of C6 glioma cells via the upregulation of focal-adhesion-finase (FAK)-targeting microRNA-7[1][2][3]. Tricin is a natural flavonoid present in large amounts in Triticum aestivum. Tricin can inhibit human cytomegalovirus (HCMV) replication by inhibiting CDK9. Tricin inhibits the proliferation and invasion of C6 glioma cells via the upregulation of focal-adhesion-finase (FAK)-targeting microRNA-7[1][2][3].

   

Geniposidic acid

7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid

C16H22O10 (374.1212912)


Geniposidic acid is found in beverages. Geniposidic acid is a constituent of Genipa americana (genipap) Constituent of Genipa americana (genipap). Geniposidic acid is found in beverages and fruits. Geniposidic acid has radiation protection and anti-cancer activity. Geniposidic acid has radiation protection and anti-cancer activity.

   

Apigenin

(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-((5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid

C21H18O11 (446.0849078)


Apigenin 7-glucuronide is a member of flavonoids and a glucosiduronic acid. Apigenin 7-glucuronide is a natural product found in Galeopsis tetrahit, Galeopsis ladanum, and other organisms with data available. Apigenin-7-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 12.87, 22.39, 17.52, 0.27 μM for MMP-3, MMP-8, MMP-9, MMP-13, respectively. Apigenin-7-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 12.87, 22.39, 17.52, 0.27 μM for MMP-3, MMP-8, MMP-9, MMP-13, respectively.

   

Luteolin 7-galactoside

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

C21H20O11 (448.100557)


Luteolin 7-galactoside is found in fruits. Luteolin 7-galactoside is isolated from Capsella bursa-pastoris (shepherds purse). Isolated from Capsella bursa-pastoris (shepherds purse). Luteolin 7-galactoside is found in herbs and spices and fruits.

   

Apigenin 7-glucuronide

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid

C21H18O11 (446.0849078)


Apigenin 7-o-glucuronide is a member of the class of compounds known as flavonoid-7-o-glucuronides. Flavonoid-7-o-glucuronides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. Apigenin 7-o-glucuronide is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Apigenin 7-o-glucuronide can be found in globe artichoke, which makes apigenin 7-o-glucuronide a potential biomarker for the consumption of this food product. Apigenin-7-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 12.87, 22.39, 17.52, 0.27 μM for MMP-3, MMP-8, MMP-9, MMP-13, respectively. Apigenin-7-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 12.87, 22.39, 17.52, 0.27 μM for MMP-3, MMP-8, MMP-9, MMP-13, respectively.

   

8-Epiloganic acid

6-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid

C16H24O10 (376.13694039999996)


   

Verbascoside

6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoic acid

C29H36O15 (624.2054106)


   

loganate

6-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid

C16H23O10 (375.1291158)


Loganate is also known as loganic acid. Loganate is soluble (in water) and a weakly acidic compound (based on its pKa). Loganate can be found in a number of food items such as hedge mustard, cinnamon, common sage, and welsh onion, which makes loganate a potential biomarker for the consumption of these food products. Loganic acid is an iridoid. Loganic acid is synthesized from 7-deoxyloganic acid by the enzyme 7-deoxyloganic acid hydroxylase (7-DLH). It is a substrate for the enzyme loganate O-methyltransferase for the production of loganin .

   

Geniposidic_acid

(1S,4aS,7aS)-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid

C16H22O10 (374.1212912)


Geniposidic acid is a terpene glycoside. Geniposidic acid is a natural product found in Avicennia officinalis, Gardenia jasminoides, and other organisms with data available. Geniposidic acid has radiation protection and anti-cancer activity. Geniposidic acid has radiation protection and anti-cancer activity.

   

Verbascoside

[(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C29H36O15 (624.2054106)


Acteoside is a glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid. It has a role as a neuroprotective agent, an antileishmanial agent, an anti-inflammatory agent, a plant metabolite and an antibacterial agent. It is a cinnamate ester, a disaccharide derivative, a member of catechols, a polyphenol and a glycoside. It is functionally related to a hydroxytyrosol and a trans-caffeic acid. Acteoside is under investigation in clinical trial NCT02662283 (Validity and Security of Reh-acteoside Therapy for Patients of IgA Nephropathy). Acteoside is a natural product found in Orobanche amethystea, Barleria lupulina, and other organisms with data available. See also: Harpagophytum zeyheri root (part of). A glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid. D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents D064449 - Sequestering Agents > D002614 - Chelating Agents D020011 - Protective Agents > D000975 - Antioxidants D000890 - Anti-Infective Agents D000970 - Antineoplastic Agents Verbascoside is isolated from Acanthus mollis, acts as an ATP-competitive inhibitor of PKC, with an IC50 of 25 μM, and has antitumor, anti-inflammatory and antineuropathic pain activity. Verbascoside is isolated from Acanthus mollis, acts as an ATP-competitive inhibitor of PKC, with an IC50 of 25 μM, and has antitumor, anti-inflammatory and antineuropathic pain activity.

   

Apigenin

5,7,4-Trihydroxyflavone

C15H10O5 (270.052821)


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

4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy- (9CI)

C15H10O6 (286.047736)


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].

   

Tricin

4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-2-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-

C17H14O7 (330.0739494)


3,5-di-O-methyltricetin is the 3,5-di-O-methyl ether of tricetin. Known commonly as tricin, it is a constituent of rice bran and has been found to potently inhibit colon cancer cell growth. It has a role as an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor and a metabolite. It is a trihydroxyflavone, a dimethoxyflavone and a member of 3-methoxyflavones. It is functionally related to a tricetin. It is a conjugate acid of a 3,5-di-O-methyltricetin(1-). Tricin is a natural product found in Carex fraseriana, Smilax bracteata, and other organisms with data available. See also: Arnica montana Flower (part of); Elymus repens root (part of). The 3,5-di-O-methyl ether of tricetin. Known commonly as tricin, it is a constituent of rice bran and has been found to potently inhibit colon cancer cell growth. Isolated from Triticum dicoccum (emmer). Tricin 5-diglucoside is found in wheat and cereals and cereal products. From leaves of Oryza sativa (rice). 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one, also known as 3,5-O-dimethyltricetin or 5,7,4-trihydroxy-3,5-dimethoxy-flavone, is a member of the class of compounds known as 3-o-methylated flavonoids. 3-o-methylated flavonoids are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. Thus, 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one is considered to be a flavonoid lipid molecule. 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one can be synthesized from tricetin. 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one is also a parent compound for other transformation products, including but not limited to, tricin 7-O-glucoside, 4-O-beta-glucosyl-7-O-(6-O-sinapoylglucosyl)tricin, and tricin 7-O-(6-O-malonyl)-beta-D-glucopyranoside. 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one can be found in barley, common wheat, oat, and rice, which makes 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one a potential biomarker for the consumption of these food products. Tricin is a natural flavonoid present in large amounts in Triticum aestivum. Tricin can inhibit human cytomegalovirus (HCMV) replication by inhibiting CDK9. Tricin inhibits the proliferation and invasion of C6 glioma cells via the upregulation of focal-adhesion-finase (FAK)-targeting microRNA-7[1][2][3]. Tricin is a natural flavonoid present in large amounts in Triticum aestivum. Tricin can inhibit human cytomegalovirus (HCMV) replication by inhibiting CDK9. Tricin inhibits the proliferation and invasion of C6 glioma cells via the upregulation of focal-adhesion-finase (FAK)-targeting microRNA-7[1][2][3].

   

Aucubin

(2S,3R,4S,5S,6R)-2-(((1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

C15H22O9 (346.1263762)


Aucubin is an organic molecular entity. It has a role as a metabolite. Aucubin is a natural product found in Verbascum lychnitis, Plantago media, and other organisms with data available. See also: Chaste tree fruit (part of); Rehmannia glutinosa Root (part of); Plantago ovata seed (part of). Origin: Plant; SubCategory_DNP: Monoterpenoids, Iridoid monoterpenoids SubCategory_DNP: Monoterpenoids, Iridoid monoterpenoids; Origin: Plant Aucubin, an iridoid glucoside, is isolated from Plantago asiatica, Eucommia ulmoides, the leaves of Aucuba japonica and more recently from butterfly larva. Aucubin has many biological activities, such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective effects[1][2][3]. Aucubin, an iridoid glucoside, is isolated from Plantago asiatica, Eucommia ulmoides, the leaves of Aucuba japonica and more recently from butterfly larva. Aucubin has many biological activities, such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective effects[1][2][3].

   

Loganic acid

(1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-1,4a,5,6,7,7a-hexahydrocyclopenta[d]pyran-4-carboxylic acid

C16H24O10 (376.13694039999996)


8-Epiloganic acid is a natural product found in Plantago atrata, Lonicera japonica, and other organisms with data available. 8-Epiloganic acid, an iridoid glucoside, can be found in Linaria cymbalaria (Scrophulariaceae)[1]. 8-Epiloganic acid, an iridoid glucoside, can be found in Linaria cymbalaria (Scrophulariaceae)[1]. Loganic acid is an iridoid isolated from cornelian cherry fruits. Loganic acid can modulate diet-induced atherosclerosis and redox status. Loganic acid has strong free radical scavenging activity and remarkable cyto-protective effect against heavy metal mediated toxicity[1][2]. Loganic acid is an iridoid isolated from cornelian cherry fruits. Loganic acid can modulate diet-induced atherosclerosis and redox status. Loganic acid has strong free radical scavenging activity and remarkable cyto-protective effect against heavy metal mediated toxicity[1][2].

   

Geniposidic acid

(1S,4aS,7aS)-7-(hydroxymethyl)-1-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-1,4a,5,7a-tetrahydrocyclopenta[d]pyran-4-carboxylic acid

C16H22O10 (374.1212912)


Geniposidic acid has radiation protection and anti-cancer activity. Geniposidic acid has radiation protection and anti-cancer activity.

   

Versulin

4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)- (9CI)

C15H10O5 (270.052821)


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.

   

threo-1-(4-hydroxy-3-methoxyphenyl)-2-{4-[-(E)-3-hydroxy-1-propenyl]-2-methoxyphenoxy}-1,3-propanediol

threo-1-(4-hydroxy-3-methoxyphenyl)-2-{4-[-(E)-3-hydroxy-1-propenyl]-2-methoxyphenoxy}-1,3-propanediol

C20H24O7 (376.1521954)


A member of the class of propane-1,3-diols that is propane-1,3-diol substituted at position 1 by a 4-hydroxy-3-methoxyphenyl and at position 2 by a 4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy group (the 1R,2R stereoisomer). It is isolated from the whole plant of Lepisorus contortus.

   

methyl (1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate

methyl (1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate

C17H26O10 (390.1525896)


   

(1s,4ar,7s)-1-{[(2s,3r,4r,5s,6r)-5-({5-[(5-{[(2r,3s,4r,5r,6s)-6-{[(1r,4ar,7as)-5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-2,5-dihydrofuran-2-yl)oxy]-2,5-dihydrofuran-2-yl}oxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7-dihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde

(1s,4ar,7s)-1-{[(2s,3r,4r,5s,6r)-5-({5-[(5-{[(2r,3s,4r,5r,6s)-6-{[(1r,4ar,7as)-5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-2,5-dihydrofuran-2-yl)oxy]-2,5-dihydrofuran-2-yl}oxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7-dihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde

C39H52O22 (872.2950092000001)


   

1-[(5-{[5-({5-[(4,5-dihydroxy-6-{[5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl)oxy]-2,5-dihydrofuran-2-yl}oxy)-2,5-dihydrofuran-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-4a,7-dihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde

1-[(5-{[5-({5-[(4,5-dihydroxy-6-{[5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl)oxy]-2,5-dihydrofuran-2-yl}oxy)-2,5-dihydrofuran-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-4a,7-dihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde

C39H52O22 (872.2950092000001)


   

3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

C21H18O11 (446.0849078)


   

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C21H20O11 (448.100557)


   

6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

C21H18O12 (462.0798228)


   

[(2r,3r,4r,5r,6r)-5-hydroxy-6-[2-(4-hydroxy-3-methoxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

[(2r,3r,4r,5r,6r)-5-hydroxy-6-[2-(4-hydroxy-3-methoxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C36H48O19 (784.2789657999999)


   

(2r,3r,4r,5r,6r)-5-hydroxy-6-[2-(4-hydroxy-3-methoxyphenyl)ethoxy]-2-(hydroxymethyl)-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

(2r,3r,4r,5r,6r)-5-hydroxy-6-[2-(4-hydroxy-3-methoxyphenyl)ethoxy]-2-(hydroxymethyl)-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C31H40O15 (652.236709)


   

(2r,3r,4r,5r,6r)-5-hydroxy-6-[2-(4-hydroxy-3-methoxyphenyl)ethoxy]-2-(hydroxymethyl)-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

(2r,3r,4r,5r,6r)-5-hydroxy-6-[2-(4-hydroxy-3-methoxyphenyl)ethoxy]-2-(hydroxymethyl)-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C30H38O15 (638.2210598)


   

(2s,3r,4s,5s,6r)-2-{4-[(1r,2r)-1,3-dihydroxy-2-{4-[(1e)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}propyl]-2,6-dimethoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5s,6r)-2-{4-[(1r,2r)-1,3-dihydroxy-2-{4-[(1e)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}propyl]-2,6-dimethoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C27H36O13 (568.2155806000001)


   

methyl 7-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate

methyl 7-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate

C17H26O10 (390.1525896)


   

{5-hydroxy-6-[2-(4-hydroxy-3-methoxyphenyl)ethoxy]-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

{5-hydroxy-6-[2-(4-hydroxy-3-methoxyphenyl)ethoxy]-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C36H48O19 (784.2789657999999)


   

(2s,3r,4s,5s,6r)-2-{4-[(1s,2s)-1,3-dihydroxy-2-{4-[(1e)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}propyl]-2,6-dimethoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5s,6r)-2-{4-[(1s,2s)-1,3-dihydroxy-2-{4-[(1e)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}propyl]-2,6-dimethoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C27H36O13 (568.2155806000001)


   

2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2-methoxyphenoxy]propyl}-2,6-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2-methoxyphenoxy]propyl}-2,6-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

C27H36O13 (568.2155806000001)


   

(2r,3r,4s,5s,6r)-2-{[(2e)-3-[(2r,3s)-2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(2e)-3-[(2r,3s)-2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C27H34O11 (534.2101014)


   

2-[4-(1,3-dihydroxy-2-{2-hydroxy-3-methoxy-5-[4-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenyl}propyl)-2,6-dimethoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

2-[4-(1,3-dihydroxy-2-{2-hydroxy-3-methoxy-5-[4-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenyl}propyl)-2,6-dimethoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C43H56O21 (908.3313926000001)


   

(1s,4ar,7s,7ar)-1-{[(2r,3s,4s,5r,6s)-5-{[(2s,5r)-5-{[(2r,5s)-5-{[(2r,3s,4r,5r,6s)-6-{[(1r,4as,5r,7ar)-5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-2,5-dihydrofuran-2-yl]oxy}-2,5-dihydrofuran-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7-dihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde

(1s,4ar,7s,7ar)-1-{[(2r,3s,4s,5r,6s)-5-{[(2s,5r)-5-{[(2r,5s)-5-{[(2r,3s,4r,5r,6s)-6-{[(1r,4as,5r,7ar)-5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-2,5-dihydrofuran-2-yl]oxy}-2,5-dihydrofuran-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7-dihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde

C39H52O22 (872.2950092000001)


   

2-(hydroxymethyl)-6-{4-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}oxane-3,4,5-triol

2-(hydroxymethyl)-6-{4-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}oxane-3,4,5-triol

C26H32O11 (520.1944522)


   

(3r,4r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2s,3s,5r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

(3r,4r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2s,3s,5r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C29H36O15 (624.2054106)


   

(2s,3s,4s,5r,6r)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

(2s,3s,4s,5r,6r)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

C21H18O12 (462.0798228)


   

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{4-[(2s,3s)-3-(hydroxymethyl)-5-[(1e)-3-hydroxyprop-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}oxane-3,4,5-triol

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{4-[(2s,3s)-3-(hydroxymethyl)-5-[(1e)-3-hydroxyprop-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}oxane-3,4,5-triol

C26H32O11 (520.1944522)