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].

   

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].

   

Hesperetin

(2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one (Hesperetin)

C16H14O6 (302.0790344)


Hesperetin, also known as prestwick_908 or YSO2, belongs to the class of organic compounds known as 4-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4 atom of the flavonoid backbone. Thus, hesperetin is considered to be a flavonoid lipid molecule. Hesperetin also seems to upregulate the LDL receptor. Hesperetin, in the form of its glycoside , is the predominant flavonoid in lemons and oranges. Hesperetin is a drug which is used for lowering cholesterol and, possibly, otherwise favorably affecting lipids. In vitro research also suggests the possibility that hesperetin might have some anticancer effects and that it might have some anti-aromatase activity. Hesperetin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Hesperetin is a bitter tasting compound. Hesperetin is found, on average, in the highest concentration within a few different foods, such as limes, persian limes, and sweet oranges and in a lower concentration in pummelo, welsh onions, and lemons. Hesperetin has also been detected, but not quantified, in several different foods, such as yellow bell peppers, carrots, rapinis, hazelnuts, and beers. Hesperetin is a biomarker for the consumption of citrus fruits. Hesperetin reduces or inhibits the activity of acyl-coenzyme A:cholesterol acyltransferase genes (ACAT1 and ACAT2) and it reduces microsomal triglyceride transfer protein (MTP) activity. Hesperetin is a trihydroxyflavanone having the three hydroxy gropus located at the 3-, 5- and 7-positions and an additional methoxy substituent at the 4-position. It has a role as an antioxidant, an antineoplastic agent and a plant metabolite. It is a monomethoxyflavanone, a trihydroxyflavanone, a member of 3-hydroxyflavanones and a member of 4-methoxyflavanones. It is a conjugate acid of a hesperetin(1-). Hesperetin belongs to the flavanone class of flavonoids. Hesperetin, in the form of its glycoside [hesperidin], is the predominant flavonoid in lemons and oranges. Hesperetin is a natural product found in Brassica oleracea var. sabauda, Dalbergia parviflora, and other organisms with data available. Isolated from Mentha (peppermint) and numerous Citrussubspecies, with lemons, tangerines and oranges being especially good sources. Nutriceutical with anti-cancer props. Glycosides also widely distributed A trihydroxyflavanone having the three hydroxy gropus located at the 3-, 5- and 7-positions and an additional methoxy substituent at the 4-position. Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CB046_Hesperetin_pos_40eV_CB000021.txt [Raw Data] CB046_Hesperetin_pos_50eV_CB000021.txt [Raw Data] CB046_Hesperetin_pos_30eV_CB000021.txt [Raw Data] CB046_Hesperetin_pos_20eV_CB000021.txt [Raw Data] CB046_Hesperetin_pos_10eV_CB000021.txt [Raw Data] CB046_Hesperetin_neg_20eV_000014.txt [Raw Data] CB046_Hesperetin_neg_10eV_000014.txt [Raw Data] CB046_Hesperetin_neg_40eV_000014.txt [Raw Data] CB046_Hesperetin_neg_50eV_000014.txt [Raw Data] CB046_Hesperetin_neg_30eV_000014.txt Hesperetin is a natural flavanone, and acts as a potent and broad-spectrum inhibitor against human UGT activity. Hesperetin regulates apoptosis. Hesperetin is a natural flavanone, and acts as a potent and broad-spectrum inhibitor against human UGT activity. Hesperetin regulates apoptosis.

   

sesamin

1,3-Benzodioxole, 5,5-(tetrahydro-1H,3H-furo(3,4-c)furan-1,4-diyl)bis-, (1S-(1.alpha.,3a.alpha.,4.alpha.,6a.alpha.))-

C20H18O6 (354.1103328)


D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D020011 - Protective Agents > D000975 - Antioxidants D009676 - Noxae > D000963 - Antimetabolites relative retention time with respect to 9-anthracene Carboxylic Acid is 1.233 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.236 Asarinin is a natural product found in Piper mullesua, Machilus thunbergii, and other organisms with data available. (-)-Asarinin is a natural product found in Zanthoxylum austrosinense, Horsfieldia irya, and other organisms with data available. (-)-Asarinin is a extract lignan from Asarum sieboldii Miq., mainly produced in roots of this herb[1]. (-)-Asarinin is a extract lignan from Asarum sieboldii Miq., mainly produced in roots of this herb[1]. (-)-Asarinin is a extract lignan from Asarum sieboldii Miq., mainly produced in roots of this herb[1]. (-)-Asarinin is a extract lignan from Asarum sieboldii Miq., mainly produced in roots of this herb[1]. Sesamin, abundant lignan found in sesame oil, is a potent and selective delta 5 desaturase inhibitor in polyunsaturated fatty acid biosynthesis. Sesamin exerts effective neuroprotection against cerbral ischemia[1][2]. Sesamin, abundant lignan found in sesame oil, is a potent and selective delta 5 desaturase inhibitor in polyunsaturated fatty acid biosynthesis. Sesamin exerts effective neuroprotection against cerbral ischemia[1][2].

   

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].

   

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].

   

tomentodiplacone

tomentodiplacone

C26H30O7 (454.199143)


   

Hesperetin

4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)- (9CI)

C16H14O6 (302.0790344)


Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.958 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.957 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.955 (Rac)-Hesperetin is the racemate of Hesperetin. Hesperetin is a natural flavanone, and acts as a potent and broad-spectrum inhibitor against human UGT activity. Hesperetin induces apoptosis via p38 MAPK activation. (Rac)-Hesperetin is the racemate of Hesperetin. Hesperetin is a natural flavanone, and acts as a potent and broad-spectrum inhibitor against human UGT activity. Hesperetin induces apoptosis via p38 MAPK activation. Hesperetin is a natural flavanone, and acts as a potent and broad-spectrum inhibitor against human UGT activity. Hesperetin regulates apoptosis. Hesperetin is a natural flavanone, and acts as a potent and broad-spectrum inhibitor against human UGT activity. Hesperetin regulates apoptosis.

   

(2s)-2-(3,4-dihydroxy-5-methoxyphenyl)-6-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one

(2s)-2-(3,4-dihydroxy-5-methoxyphenyl)-6-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one

C27H32O7 (468.2147922)


   

(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one

(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one

C21H22O7 (386.1365462)


   

(2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,7r)-3,7-bis(acetyloxy)icosanoate

(2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,7r)-3,7-bis(acetyloxy)icosanoate

C29H52O9 (544.3611142)


   

(2s)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-[(3e,6e)-8-hydroxy-4,8-dimethylnona-3,6-dien-1-yl]-2,3-dihydro-1-benzopyran-4-one

(2s)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-[(3e,6e)-8-hydroxy-4,8-dimethylnona-3,6-dien-1-yl]-2,3-dihydro-1-benzopyran-4-one

C27H32O7 (468.2147922)


   

1,3-dihydroxypropan-2-yl 3,7-bis(acetyloxy)octadecanoate

1,3-dihydroxypropan-2-yl 3,7-bis(acetyloxy)octadecanoate

C25H46O8 (474.3192516)


   

1-(acetyloxy)-3-hydroxypropan-2-yl 3,8-bis(acetyloxy)icosanoate

1-(acetyloxy)-3-hydroxypropan-2-yl 3,8-bis(acetyloxy)icosanoate

C29H52O9 (544.3611142)


   

6-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

6-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

C27H32O7 (468.2147922)


   

(2s)-6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

(2s)-6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

C26H30O6 (438.204228)


   

5,6-dihydroxy-2-(hydroxymethyl)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

5,6-dihydroxy-2-(hydroxymethyl)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

C21H28O13 (488.1529838)


   

1,3-dihydroxypropan-2-yl 3-(acetyloxy)-9-hydroxyicosanoate

1,3-dihydroxypropan-2-yl 3-(acetyloxy)-9-hydroxyicosanoate

C25H48O7 (460.33998579999997)


   

(2s)-6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

(2s)-6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

C27H32O7 (468.2147922)


   

(2s)-6-(6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

(2s)-6-(6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

C25H30O7 (442.199143)


   

1,3-dihydroxypropan-2-yl (3r,6s)-3,6-dihydroxyicosanoate

1,3-dihydroxypropan-2-yl (3r,6s)-3,6-dihydroxyicosanoate

C23H46O6 (418.3294216)


   

1-(acetyloxy)-3-hydroxypropan-2-yl 3,7-bis(acetyloxy)icosanoate

1-(acetyloxy)-3-hydroxypropan-2-yl 3,7-bis(acetyloxy)icosanoate

C29H52O9 (544.3611142)


   

6-(4,8-dimethylnona-3,7-dien-1-yl)-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

6-(4,8-dimethylnona-3,7-dien-1-yl)-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

C28H34O7 (482.2304414)


   

(2r,3r)-2-(3,4-dihydroxyphenyl)-6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-3,5,7-trihydroxy-2,3-dihydro-1-benzopyran-4-one

(2r,3r)-2-(3,4-dihydroxyphenyl)-6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-3,5,7-trihydroxy-2,3-dihydro-1-benzopyran-4-one

C25H28O7 (440.1834938)


   

(5s)-9,12-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-13-methyl-13-(4-methylpent-3-en-1-yl)-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1,3(8),9-trien-7-one

(5s)-9,12-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-13-methyl-13-(4-methylpent-3-en-1-yl)-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1,3(8),9-trien-7-one

C26H30O7 (454.199143)


   

6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

C27H32O7 (468.2147922)


   

2-(3,4-dihydroxy-5-methoxyphenyl)-6-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one

2-(3,4-dihydroxy-5-methoxyphenyl)-6-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one

C26H30O7 (454.199143)


   

(2r,3r)-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methyl-8-(4-methylpent-3-en-1-yl)-2h,3h-pyrano[3,2-g]chromen-4-one

(2r,3r)-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methyl-8-(4-methylpent-3-en-1-yl)-2h,3h-pyrano[3,2-g]chromen-4-one

C26H28O7 (452.1834938)


   

(2r,3r,4r,5r,6r)-5-hydroxy-6-[2-(3-hydroxy-4-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-(3-hydroxy-4-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)-6-[2-(3,4-dihydroxyphenyl)-2-methoxyethoxy]-5-hydroxy-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)-6-[2-(3,4-dihydroxyphenyl)-2-methoxyethoxy]-5-hydroxy-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

C30H38O16 (654.2159748)


   

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl)-2,3-dihydro-1-benzopyran-4-one

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl)-2,3-dihydro-1-benzopyran-4-one

C25H28O7 (440.1834938)


   

(2s)-2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-6-[(2e,6r)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2,3-dihydro-1-benzopyran-4-one

(2s)-2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-6-[(2e,6r)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2,3-dihydro-1-benzopyran-4-one

C26H30O8 (470.194058)


   

(2s)-5,7-dihydroxy-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

(2s)-5,7-dihydroxy-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

C18H18O7 (346.10524780000003)


   

1,3-dihydroxypropan-2-yl 3,9-dihydroxyicosanoate

1,3-dihydroxypropan-2-yl 3,9-dihydroxyicosanoate

C23H46O6 (418.3294216)


   

1,3-dihydroxypropan-2-yl (3r,8r)-3-(acetyloxy)-8-hydroxyicosanoate

1,3-dihydroxypropan-2-yl (3r,8r)-3-(acetyloxy)-8-hydroxyicosanoate

C25H48O7 (460.33998579999997)


   

(2s)-6-[(2e)-6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

(2s)-6-[(2e)-6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

C25H30O7 (442.199143)


   

1-(acetyloxy)-3-hydroxypropan-2-yl 3-(acetyloxy)-9-hydroxyicosanoate

1-(acetyloxy)-3-hydroxypropan-2-yl 3-(acetyloxy)-9-hydroxyicosanoate

C27H50O8 (502.35055)


   

1-(acetyloxy)-3-hydroxypropan-2-yl 3-(acetyloxy)icosanoate

1-(acetyloxy)-3-hydroxypropan-2-yl 3-(acetyloxy)icosanoate

C27H50O7 (486.355635)


   

1,3-dihydroxypropan-2-yl (3r)-3-(acetyloxy)icosanoate

1,3-dihydroxypropan-2-yl (3r)-3-(acetyloxy)icosanoate

C25H48O6 (444.3450708)