NCBI Taxonomy: 75629

Centaurea behen (ncbi_taxid: 75629)

found 20 associated metabolites at species taxonomy rank level.

Ancestor: Centaurea

Child Taxonomies: none taxonomy data.

Cynaropicrin

2-PROPENOIC ACID, 2-(HYDROXYMETHYL)-, DODECAHYDRO-8-HYDROXY-3,6,9-TRIS(METHYLENE)-2-OXOAZULENO(4,5-B)FURAN-4-YL ESTER, (3AR-(3A.ALPHA.,4.ALPHA.,6A.ALPHA.,8.BETA.,9A.ALPHA.,9B.BETA.))-

C19H22O6 (346.1416)


Constituent of Cynara scolymus (artichoke). Cynaropicrin is found in cardoon, globe artichoke, and root vegetables. Cynaropicrin is found in cardoon. Cynaropicrin is a constituent of Cynara scolymus (artichoke). Cynaropicrin is a sesquiterpene lactone. Cynaropicrin is a natural product found in Pleiotaxis rugosa, Pseudostifftia kingii, and other organisms with data available. See also: Cynara scolymus leaf (part of). D009676 - Noxae > D003603 - Cytotoxins Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor (TNF-α) release with IC50s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling. Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor (TNF-α) release with IC50s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling.

   

Grosheimin

(3aR,4S,6aR,9S,9aR,9bR)-Octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)azuleno[4,5-b]furan-2,8(3H,4H)-dione

C15H18O4 (262.1205)


Origin: Plant; SubCategory_DNP: Sesquiterpenoids (3aR,4S,6aR,9S,9aR,9bR)-Octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)azuleno[4,5-b]furan-2,8(3H,4H)-dione. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=22489-66-3 (retrieved 2024-07-09) (CAS RN: 22489-66-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

8-Deoxy-11,13-dihydroxygrosheimin

3-hydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2,8-dione

C15H20O5 (280.1311)


8-Deoxy-11,13-dihydroxygrosheimin is found in green vegetables. 8-Deoxy-11,13-dihydroxygrosheimin is a constituent of Cynara scolymus (globe artichoke). Constituent of Cynara scolymus (globe artichoke). 8-Deoxy-11,13-dihydroxygrosheimin is found in green vegetables.

   

Grosheimin

Azuleno[4,5-b]furan-2,8(3H,4H)-dione, octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, [3aR-(3aalpha,4alpha,6aalpha,9alpha,9aalpha,9bbeta)]-

C15H18O4 (262.1205)


Grosheimin belongs to guaianolides and derivatives class of compounds. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Grosheimin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Grosheimin is a bitter tasting compound found in globe artichoke, which makes grosheimin a potential biomarker for the consumption of this food product.

   

Cynaropicrin

2-PROPENOIC ACID, 2-(HYDROXYMETHYL)-, DODECAHYDRO-8-HYDROXY-3,6,9-TRIS(METHYLENE)-2-OXOAZULENO(4,5-B)FURAN-4-YL ESTER, (3AR-(3A.ALPHA.,4.ALPHA.,6A.ALPHA.,8.BETA.,9A.ALPHA.,9B.BETA.))-

C19H22O6 (346.1416)


Cynaropicrin is a sesquiterpene lactone. Cynaropicrin is a natural product found in Pleiotaxis rugosa, Pseudostifftia kingii, and other organisms with data available. See also: Cynara scolymus leaf (part of). D009676 - Noxae > D003603 - Cytotoxins Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor (TNF-α) release with IC50s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling. Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor (TNF-α) release with IC50s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling.

   

8-Deoxy-11,13-dihydroxygrosheimin

3-hydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2,8-dione

C15H20O5 (280.1311)


   
   

(3ar,4s,6ar,8s,9ar,9br)-4,8-dihydroxy-3,6,9-trimethylidene-octahydroazuleno[4,5-b]furan-2-one

(3ar,4s,6ar,8s,9ar,9br)-4,8-dihydroxy-3,6,9-trimethylidene-octahydroazuleno[4,5-b]furan-2-one

C15H18O4 (262.1205)


   

[(3r,3ar,6ar,9s,9ar,9br)-3-hydroxy-9-methyl-6-methylidene-2,8-dioxo-octahydroazuleno[4,5-b]furan-3-yl]methyl acetate

[(3r,3ar,6ar,9s,9ar,9br)-3-hydroxy-9-methyl-6-methylidene-2,8-dioxo-octahydroazuleno[4,5-b]furan-3-yl]methyl acetate

C17H22O6 (322.1416)


   

(3ar,4s,6ar,8s,9s,9ar,9br)-8-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

(3ar,4s,6ar,8s,9s,9ar,9br)-8-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

C19H24O6 (348.1573)


   

8-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

8-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

C19H22O5 (330.1467)


   

(3ar,4s,6ar,8s,9s,9ar,9br)-8-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

(3ar,4s,6ar,8s,9s,9ar,9br)-8-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

C19H24O5 (332.1624)


   

4,8-dihydroxy-9-methyl-3,6-dimethylidene-octahydro-3ah-azuleno[4,5-b]furan-2-one

4,8-dihydroxy-9-methyl-3,6-dimethylidene-octahydro-3ah-azuleno[4,5-b]furan-2-one

C15H20O4 (264.1362)


   

(3ar,4s,6ar,8s,9ar,9br)-8-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

(3ar,4s,6ar,8s,9ar,9br)-8-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

C19H22O5 (330.1467)


   

(3ar,4s,6ar,8s,9s,9ar,9br)-4,8-dihydroxy-9-methyl-3,6-dimethylidene-octahydro-3ah-azuleno[4,5-b]furan-2-one

(3ar,4s,6ar,8s,9s,9ar,9br)-4,8-dihydroxy-9-methyl-3,6-dimethylidene-octahydro-3ah-azuleno[4,5-b]furan-2-one

C15H20O4 (264.1362)


   

(3r,3ar,6ar,9s,9ar,9br)-3-hydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-octahydroazuleno[4,5-b]furan-2,8-dione

(3r,3ar,6ar,9s,9ar,9br)-3-hydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-octahydroazuleno[4,5-b]furan-2,8-dione

C15H20O5 (280.1311)


   

{3-hydroxy-9-methyl-6-methylidene-2,8-dioxo-octahydroazuleno[4,5-b]furan-3-yl}methyl acetate

{3-hydroxy-9-methyl-6-methylidene-2,8-dioxo-octahydroazuleno[4,5-b]furan-3-yl}methyl acetate

C17H22O6 (322.1416)


   

8-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

8-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

C19H24O6 (348.1573)


   

4,8-dihydroxy-3,6,9-trimethylidene-octahydroazuleno[4,5-b]furan-2-one

4,8-dihydroxy-3,6,9-trimethylidene-octahydroazuleno[4,5-b]furan-2-one

C15H18O4 (262.1205)


   

8-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

8-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

C19H24O5 (332.1624)