Classification Term: 168658

Coumestan flavonoids [PK1209] (ontology term: 9ab3d1f86e517fdf8f5d1fb3b9d3a0e2)

Coumestan flavonoids [PK1209]

found 53 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Flavonoids [PK12]

Child Taxonomies: There is no child term of current ontology term.

Coumesterol

3,9-dihydroxy-[1]benzofuro[3,2-c]chromen-6-one

C15H8O5 (268.0372)


Cumoesterol (or coumestrol), a coumestan isoflavone, has estrogenic properties (phytoestrogens are compounds structurally and functionally similar to 17-estradiol) and is an isoflavonoid phytoalexin produced by soybeans, a low molecular weight antimicrobial compound that is synthesized de novo and accumulates in plants after exposure to microorganisms (i.e.: phytoalexin induction and accumulation in soybean cotyledon tissue is observed with four species of Aspergillus: A. sojae, A. oryzae, A. niger, and A. flavus) (PMID: 10888516). Coumestrol is a naturally occurring plant coumarin that displays high affinity for the hormone-binding site of the human estrogen receptor (hER), for which it serves as a potent non-steroidal agonist. Coumestrol emits intense blue fluorescence when bound to this protein, making it ideally suited for use as a cytological stain to detect ER in fixed and intact cells. Such observations illustrate the potential for using coumestrol to investigate real-time effects of a variety of physiological stimuli on the subcellular distribution of hER in living cells (PMID: 8315272). Coumestrol is a member of the class of coumestans that is coumestan with hydroxy substituents at positions 3 and 9. It has a role as an anti-inflammatory agent, an antioxidant and a plant metabolite. It is a member of coumestans, a delta-lactone and a polyphenol. It is functionally related to a coumestan. Coumestrol is a natural product found in Campylotropis hirtella, Melilotus messanensis, and other organisms with data available. A daidzein derivative occurring naturally in forage crops which has some estrogenic activity. See also: Medicago sativa whole (part of). Isolated from Medicago subspecies, Glycine max (soybean), Pisum sativum (pea), Spinacia oleracea (spinach), Brassica oleracea (cabbage), Dolichos biflorus (papadi), Melilotus alba (white melilot), Phaseolus subspecies (inc. lima beans, pinto beans) and Vigna unguiculata (all Leguminosae). Potential nutriceutical D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens A member of the class of coumestans that is coumestan with hydroxy substituents at positions 3 and 9. Coumestrol, a phytoestrogen present in soybean products, exhibits activities against cancers, neurological disorders, and autoimmune diseases. It suppresses proliferation of ES2 cells with an IC50 of 50 μM. Coumestrol, a phytoestrogen present in soybean products, exhibits activities against cancers, neurological disorders, and autoimmune diseases. It suppresses proliferation of ES2 cells with an IC50 of 50 μM.

   

Psoralidin

3,9-dihydroxy-2-(3-methylbut-2-enyl)-[1]benzofuro[3,2-c]chromen-6-one

C20H16O5 (336.0998)


Psoralidin is a member of the class of coumestans that is coumestan substituted by hydroxy groups at positions 3 and 9 and a prenyl group at position 2 respectively. It has a role as a plant metabolite and an estrogen receptor agonist. It is a member of coumestans, a polyphenol and a delta-lactone. It is functionally related to a coumestan. Psoralidin is a natural product found in Dolichos trilobus, Phaseolus lunatus, and other organisms with data available. See also: Cullen corylifolium fruit (part of). A member of the class of coumestans that is coumestan substituted by hydroxy groups at positions 3 and 9 and a prenyl group at position 2 respectively. D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D020847 - Estrogen Receptor Modulators Constituent of papadi (Dolichos biflorus) and the butter bean (Phaseolus lunatus). Psoralidin is found in pulses, lima bean, and fruits. Psoralidin is found in fruits. Psoralidin is a constituent of papadi (Dolichos biflorus) and the butter bean (Phaseolus lunatus). Psoralidin is a dual inhibitor of COX-2 and 5-LOX, regulates ionizing radiation (IR)-induced pulmonary inflammation.Anti-cancer, anti-bacterial, and anti-inflammatory properties[1]. Psoralidin significantly downregulates NOTCH1 signaling. Psoralidin also greatly induces ROS generation[2]. Psoralidin is a dual inhibitor of COX-2 and 5-LOX, regulates ionizing radiation (IR)-induced pulmonary inflammation.Anti-cancer, anti-bacterial, and anti-inflammatory properties[1]. Psoralidin significantly downregulates NOTCH1 signaling. Psoralidin also greatly induces ROS generation[2]. Psoralidin is a dual inhibitor of COX-2 and 5-LOX, regulates ionizing radiation (IR)-induced pulmonary inflammation.Anti-cancer, anti-bacterial, and anti-inflammatory properties[1]. Psoralidin significantly downregulates NOTCH1 signaling. Psoralidin also greatly induces ROS generation[2].

   

Sojagol

7-hydroxy-17,17-dimethyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-1(13),2(11),5(10),6,8,14(19),20-heptaen-3-one

C20H16O5 (336.0998)


Sojagol is found in pulses. Sojagol is isolated from soya (leaves and hypocotyls) and from mung beans (Phaseolus aureus). Isol. from soya (leaves and hypocotyls) and from mung beans (Phaseolus aureus). Sojagol is found in soy bean and pulses.

   

Wedelolactone

3,13,14-trihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11,13,15-heptaen-9-one

C16H10O7 (314.0427)


Wedelolactone suppresses LPS-induced caspase-11 expression by directly inhibits the IKK Complex. Wedelolactone also inhibits 5-lipoxygenase (5-Lox) with an IC50 of 2.5 μM. Wedelolactone induces caspase-dependent apoptosis in prostate cancer cells via downregulation of PKCε without inhibiting Akt. Wedelolactone can extract from Eclipta alba, and it can be used for the research of cancer[1][2][3]. Wedelolactone suppresses LPS-induced caspase-11 expression by directly inhibits the IKK Complex. Wedelolactone also inhibits 5-lipoxygenase (5-Lox) with an IC50 of 2.5 μM. Wedelolactone induces caspase-dependent apoptosis in prostate cancer cells via downregulation of PKCε without inhibiting Akt. Wedelolactone can extract from Eclipta alba, and it can be used for the research of cancer[1][2][3]. Wedelolactone suppresses LPS-induced caspase-11 expression by directly inhibits the IKK Complex. Wedelolactone also inhibits 5-lipoxygenase (5-Lox) with an IC50 of 2.5 μM. Wedelolactone induces caspase-dependent apoptosis in prostate cancer cells via downregulation of PKCε without inhibiting Akt. Wedelolactone can extract from Eclipta alba, and it can be used for the research of cancer[1][2][3].

   

Medicagol

16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2,4(8),9,13(18),14,16-heptaen-20-one

C16H8O6 (296.0321)


Medicagol is a member of coumestans. Medicagol is a natural product found in Cicer chorassanicum, Sophora moorcroftiana, and other organisms with data available. See also: Trifolium pratense flower (part of). Medicagol is found in alfalfa. Medicagol is found in alfalfa (Medicago sativa) having viral leaf spot infections. Also from Cicer arietinum (chick pea) and Trifolium pratense (red clover). Found in alfalfa (Medicago sativa) having viral leaf spot infectionsand is also from Cicer arietinum (chick pea) and Trifolium pratense (red clover).

   

UXN2KXV8BB

6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 1,3,8,9-tetrahydroxy-

C15H8O7 (300.027)


Demethylwedelolactone is a member of coumestans. Demethylwedelolactone is a natural product found in Sphagneticola calendulacea, Eclipta alba, and other organisms with data available. Demethylwedelolactone is a naturally occurring coumestan isolated from Eclipta alba. Demethylwedelolactone is a potent trypsin inhibitor with an IC50 of 3.0 μM. Demethylwedelolactone suppresses cell motility and cell invasion of breast cancer cell[1][2]. Demethylwedelolactone is a naturally occurring coumestan isolated from Eclipta alba. Demethylwedelolactone is a potent trypsin inhibitor with an IC50 of 3.0 μM. Demethylwedelolactone suppresses cell motility and cell invasion of breast cancer cell[1][2].

   

Wedelolactone

6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 1,8,9-trihydroxy-3-methoxy-

C16H10O7 (314.0427)


Wedelolactone is a member of the class of coumestans that is coumestan with hydroxy substituents as positions 1, 8 and 9 and a methoxy substituent at position 3. It has a role as an antineoplastic agent, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an apoptosis inducer, a hepatoprotective agent and a metabolite. It is a member of coumestans, a delta-lactone, an aromatic ether and a polyphenol. It is functionally related to a coumestan. Wedelolactone is a natural product found in Sphagneticola calendulacea, Eclipta alba, and other organisms with data available. A member of the class of coumestans that is coumestan with hydroxy substituents as positions 1, 8 and 9 and a methoxy substituent at position 3. Wedelolactone suppresses LPS-induced caspase-11 expression by directly inhibits the IKK Complex. Wedelolactone also inhibits 5-lipoxygenase (5-Lox) with an IC50 of 2.5 μM. Wedelolactone induces caspase-dependent apoptosis in prostate cancer cells via downregulation of PKCε without inhibiting Akt. Wedelolactone can extract from Eclipta alba, and it can be used for the research of cancer[1][2][3]. Wedelolactone suppresses LPS-induced caspase-11 expression by directly inhibits the IKK Complex. Wedelolactone also inhibits 5-lipoxygenase (5-Lox) with an IC50 of 2.5 μM. Wedelolactone induces caspase-dependent apoptosis in prostate cancer cells via downregulation of PKCε without inhibiting Akt. Wedelolactone can extract from Eclipta alba, and it can be used for the research of cancer[1][2][3]. Wedelolactone suppresses LPS-induced caspase-11 expression by directly inhibits the IKK Complex. Wedelolactone also inhibits 5-lipoxygenase (5-Lox) with an IC50 of 2.5 μM. Wedelolactone induces caspase-dependent apoptosis in prostate cancer cells via downregulation of PKCε without inhibiting Akt. Wedelolactone can extract from Eclipta alba, and it can be used for the research of cancer[1][2][3].

   

Tephcalostan B

Tephcalostan B

C20H12O6 (348.0634)


   

Mirificoumestan glycol

3,9-Dihydroxy-8-methoxy-7- (2,3-dihydroxy-3-methylbutyl) coumestan

C21H20O8 (400.1158)


   

Psoralidin oxide

Psoralidin oxide

C20H16O6 (352.0947)


   

Bavacoumestan A

Bavacoumestan A

C20H16O6 (352.0947)


   

Demethylwedelolactone 3-O-glucoside

5,7,11,12-Tetrahydroxycoumestan 3-O-glucoside

C21H18O12 (462.0798)


   

Corylidin

1,2,10-Trihydroxy-3,3-dimethyl-2,3-dihydro-1H,7H-benzofuro [ 3,2-c ] pyrano [ 3,2-g ] [ 1 ] benzopyran-7-one

C20H16O7 (368.0896)


   

Tephcalostan

8,9-Methylenedioxy-5-(1-methylethenyl)-4,5-dihydrofurano[2,3:3,2]-coumestan

C21H14O6 (362.079)


   

Bavacoumestan B

Bavacoumestan B

C20H16O6 (352.0947)


   

Mirificoumestan hydrate

3,9-Dihydroxy-8-methoxy-7-(3-hydroxy-3-methylbutyl)coumestan

C21H20O7 (384.1209)


   

Sativol

8,12-Dihydroxy-7-methoxycoumestan

C16H10O6 (298.0477)


   

Mirificoumestan

3,9-Dihydroxy-8-methoxy-7-prenylcoumestan

C21H18O6 (366.1103)


   

3,9-Dihydroxy-1-methoxy-8-prenylcoumestan

3,9-Dihydroxy-1-methoxy-8-prenylcoumestan

C21H18O6 (366.1103)


   

Puerarostan

3,9-Dihydroxy-4-methoxy-8-prenylcoumestan

C21H18O6 (366.1103)


   

Mutisifurocoumarin

3-Hydroxy-4-methoxy-8,9-methylenedioxycoumestan

C16H10O5 (282.0528)


   

Puerarol

3,9-Dihydroxy-2-geranylcoumestan

C25H24O5 (404.1624)


   

Coumestrol dimethyl ether

3,9-Dimethoxy-6-oxopterocarpene

C17H12O5 (296.0685)


   

9-O-Methylcoumestrol

3-hydroxy-9-methoxycoumestan

C16H10O5 (282.0528)


   

Flemichapparin C

3-Methoxy-8,9-methylenedioxycoumestan

C17H10O6 (310.0477)


   

2-Hydroxyflemichapparin C

2-Hydroxy-3-methoxy-8,9-methylenedioxycoumestan

C17H10O7 (326.0427)


   

Tephrosol

3-Hydroxy-2-methoxy-8,9-methylenedioxycoumestan

C17H10O7 (326.0427)


   

Sophoracoumestan B

3-Hydroxy-4-methoxy-8,9-methylenedioxycoumestan

C17H10O7 (326.0427)


   

2-Hydroxy-1,3-dimethoxy-8,9-methylenedioxycoumestan

2-Hydroxy-1,3-dimethoxy-8,9-methylenedioxycoumestan

C18H12O8 (356.0532)


   

Lucernol

2,3,9-Trihydroxycoumestan

C15H8O6 (284.0321)


   

Isopsoralidin

10-Hydroxy-3,3-dimethyl-2,3-dihydro-1H,7H-benzofuro [ 3,2-c ] pyrano [ 3,2-g ] [ 1 ] benzopyran-7-one

C20H16O5 (336.0998)


   

Isoglycyrol

3,4-Dihydro-2,2-dimethyl-11-hydroxy-5-methoxy-2H,8H-benzofuro [ 3,2-c ] pyrano [ 2,3-f ] [ 1 ] benzopyran-8-one

C21H18O6 (366.1103)


   

Sophoracoumestan A

3-Hydroxy-10,10-dimethyl-6H,10H-furo [ 3,2-c:4,5-g ] bis [ 1 ] benzopyran-6-one

C20H14O5 (334.0841)


   
   

Aureol

1,3,9-Trihydroxycoumestan

C15H8O6 (284.0321)


   

Coumestrin

14-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11,13,15-heptaen-9-one

C21H18O10 (430.09)


   

Phaseol

3,9-Dihydroxy-4-prenylcoumestan

C20H16O5 (336.0998)


   

Trifoliol

7,10-Dihydroxy-12-methoxycoumestan

C16H10O6 (298.0477)


   

5-O-Methylglycyrol

9-Hydroxy-1,3-dimethoxy-2-prenylcoumestan

C22H20O6 (380.126)


   

3-Hydroxy-8,9-dimethoxycoumestan

3-Hydroxy-8,9-dimethoxycoumestan

C17H12O6 (312.0634)


   

Wairol

7-Hydroxy-10,12-dimethoxycoumestan

C17H12O6 (312.0634)


   

Sojagol

2,3-Dihydro-10-hydroxy-3,3-dimethyl-1H,7H-furo [ 3,2-c:5,4-f ] bis [ 1 ] benzopyran-7-one

C20H16O5 (336.0998)


A member of the class of coumestans that is coumestan substituted by a hydroxy group at position 3 and a 2,2-dimethylpyran group across positions 9 and 10.

   

Erosnin

6H- [ 1,3 ] Dioxolo [ 5,6 ] benzofuro [ 3,2-c ] furo [ 3,2-g ] [ 1 ] benzopyran-6-one

C18H8O6 (320.0321)


   

Glycyrol

3,9-Dihydroxy-1-methoxy-2- (3-methyl-2-buten-1-yl) -6H-benzofuro [3,2-c] [1] benzopyran-6-one

C21H18O6 (366.1103)


Neoglycyrol is isolated from the root of Glycyrrhiza uralensis Fisch[1]. Neoglycyrol is a potential myocardial protection active compound screened from traditional patent medicine Tongmai Yangxin pill (TMYXP)[2]. Neoglycyrol is isolated from the root of Glycyrrhiza uralensis Fisch[1]. Neoglycyrol is a potential myocardial protection active compound screened from traditional patent medicine Tongmai Yangxin pill (TMYXP)[2].

   

Isosojagol

3,9-Dihydroxy-10-(3-methyl-2-buten-1-yl)-6H-benzofuro[3,2-c][1]benzopyran-6-one

C20H16O5 (336.0998)


A member of the class of coumestans that is coumestrol with a prenyl substituent at position 10.

   

3-Methoxycoumestrol

7,12-Dihydroxy-11-methoxycoumestan

C16H10O6 (298.0477)


   

7,10,12-Trihydroxycoumestan

Repensol3,7,9-Trihydroxycoumestan

C15H8O6 (284.0321)


   

Gancaonin F

Gancaonin F

C21H16O6 (364.0947)


   

Tephcalostan C

Tephcalostan C

C21H16O7 (380.0896)


   

Tephcalostan C

Tephcalostan C

C21H14O7 (378.0739)


   

Campylohirtin A

1,3-dimethoxy-8,9-dihydroxy-2-prenylcoumestan

C22H22O7 (398.1365)


   

1-methoxy-3,8,9-trihydroxy-2-prenylcoumestan

7,4,5-trihydroxy-5-methoxy-2-[3-methyl-2-butenyl]-coumestan

C21H20O7 (384.1209)


   

HIRTELLANINE B

1-methoxy-8,9-dihydroxy-6,6-dimethylpyrano-[2,3:2,3]-coumestan

C21H18O7 (382.1052)