Classification Term: 1546

Eudesmanolides, secoeudesmanolides, and derivatives (ontology term: CHEMONTID:0001772)

Terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton." [DOI:10.3109/10408444.2013.813905]

found 36 associated metabolites at family metabolite taxonomy ontology rank level.

Ancestor: Sesquiterpene lactones

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

Isoalantolactone

Naphtho(2,3-b)furan-2(3H)-one, decahydro-8a-methyl-3,5-bis(methylene)-, (3aR-(3a alpha,4a alpha,8a beta,9a alpha))-

C15H20O2 (232.1463)


Isoalantolactone is a sesquiterpene lactone of the eudesmanolide group. It has been isolated from Inula helenium. It has a role as an apoptosis inducer, an antifungal agent and a plant metabolite. It is a sesquiterpene lactone and a eudesmane sesquiterpenoid. Isoalantolactone is a natural product found in Eupatorium cannabinum, Critonia quadrangularis, and other organisms with data available. Isoalantolactone is found in herbs and spices. Isoalantolactone is a constituent of the essential oil of Inula helenium (elecampane) Constituent of the essential oil of Inula helenium (elecampane). Isoalantolactone is found in herbs and spices. Isoalantolactone is an apoptosis inducer, which also acts as an alkylating agent. Isoalantolactone is an apoptosis inducer, which also acts as an alkylating agent.

   

Alantolactone

Naphtho(2,3-b)furan-2(3H)-one, 3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylene-, (3aR-(3a alpha,5beta,8a beta,9a alpha))-

C15H20O2 (232.1463)


Alantolactone is a sesquiterpene lactone that is 3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2-one bearing two methyl substituents at positions 5 and 8a as well as a methylidene substituent at position 3. It has a role as a plant metabolite, an apoptosis inducer and an antineoplastic agent. It is a sesquiterpene lactone, a naphthofuran and an olefinic compound. Alantolactone is a natural product found in Eupatorium cannabinum, Pentanema britannicum, and other organisms with data available. Alantolactone is found in herbs and spices. Alantolactone is a constituent of Inula helenium (elecampane) Constituent of Inula helenium (elecampane). Alantolactone is found in herbs and spices. Alantolactone is a selective STAT3 inhibitor, with potent anticancer activity. Alantolactone induces apoptosis in cancer[1][2][3]. Alantolactone is a selective STAT3 inhibitor, with potent anticancer activity. Alantolactone induces apoptosis in cancer[1][2][3].

   

Santamarin

NAPHTHO(1,2-B)FURAN-2(3H)-ONE, 3A,4,5,5A,6,7,9A,9B-OCTAHYDRO-6-HYDROXY-5A,9-DIMETHYL-3-METHYLENE-, (3AS-(3A.ALPHA.,5A.BETA.,6.BETA.,9A.ALPHA.,9B.BETA.))-

C15H20O3 (248.1412)


Santamarin, also known as (+)-santamarine or balchanin, belongs to eudesmanolides, secoeudesmanolides, and derivatives class of compounds. Those are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Santamarin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Santamarin can be found in sweet bay, which makes santamarin a potential biomarker for the consumption of this food product. Santamarin is a sesquiterpene lactone of the eudesmanolide group. Santamarine is a natural product found in Centaurea uniflora, Eupatorium capillifolium, and other organisms with data available.

   

Vulgarin

9-hydroxy-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,6H,9H,9aH,9bH-naphtho[1,2-b]furan-2,6-dione

C15H20O4 (264.1362)


Vulgarin is found in mugwort. Vulgarin is a constituent of Artemisia vulgaris (mugwort) Constituent of Artemisia vulgaris (mugwort). Vulgarin is found in mugwort.

   

Encelin

8a-methyl-3,5-dimethylidene-2H,3H,3aH,4H,4aH,5H,6H,8aH,9H,9aH-naphtho[2,3-b]furan-2,6-dione

C15H16O3 (244.1099)


Encelin is found in herbs and spices. Encelin is a constituent of Inula helenium (elecampane) Constituent of Inula helenium (elecampane). Encelin is found in herbs and spices.

   

2alpha-Hydroxyalantolactone

7-hydroxy-5,8a-dimethyl-3-methylidene-2H,3H,3aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

C15H20O3 (248.1412)


2alpha-Hydroxyalantolactone is found in herbs and spices. 2alpha-Hydroxyalantolactone is a constituent of Inula helenium (elecampane) Constituent of Inula helenium (elecampane). 2alpha-Hydroxyalantolactone is found in herbs and spices.

   

Artemin

[3S-(3alpha,3aalpha,5abeta,6beta,9aalpha,9bbeta)]-Decahydro-6,9a-dihydroxy-3,5a-dimethyl-9-methylenenaphtho[1,2-b]furan-2(3H)-one

C15H22O4 (266.1518)


Artemin is found in herbs and spices. Artemin is a constituent of Artemisia species Constituent of Artemisia subspecies Artemin is found in herbs and spices.

   

Alkhanin

[3S-(3alpha,3aalpha,5abeta,6alpha,9bbeta)]-3a,5,5a,6,7,9b-Hexahydro-6-hydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)-dione

C15H20O4 (264.1362)


Alkhanin is found in herbs and spices. Alkhanin is isolated from Balsamita major (costmary Isolated from Balsamita major (costmary). Alkhanin is found in tea and herbs and spices.

   

Dihydroisoalantolactone

3,8a-dimethyl-5-methylidene-octahydro-3H-naphtho[2,3-b]furan-2-one

C15H22O2 (234.162)


Dihydroisoalantolactone is found in herbs and spices. Dihydroisoalantolactone is isolated from roots of Inula helenium (elecampane Isolated from roots of Inula helenium (elecampane). Dihydroisoalantolactone is found in herbs and spices.

   

4,11,13,15-Tetrahydroridentin B

(3S,3aS,5aR,6R,8S,9R,9aS,9bS)-6,8-dihydroxy-3,5a,9-trimethyl-dodecahydronaphtho[1,2-b]furan-2-one

C15H24O4 (268.1675)


Constituent of Taraxacum officinale (dandelion). 4,11,13,15-Tetrahydroridentin B is found in many foods, some of which are alcoholic beverages, beverages, coffee and coffee products, and dandelion. 4,11,13,15-Tetrahydroridentin B is found in alcoholic beverages. 4,11,13,15-Tetrahydroridentin B is a constituent of Taraxacum officinale (dandelion)

   

Arabsin

[3R-(3alpha,3abeta,5aalpha,6alpha,9beta,9abeta,9balpha)]-Octahydro-6-hydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)-dione

C15H22O4 (266.1518)


Constituent of Artemisia absinthium (wormwood). Arabsin is found in alcoholic beverages and herbs and spices. Arabsin is found in alcoholic beverages. Arabsin is a constituent of Artemisia absinthium (wormwood)

   

3-Epiarmefolin

6,8-dihydroxy-5a,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9bH-naphtho[1,2-b]furan-2-one

C15H20O4 (264.1362)


3-Epiarmefolin is found in herbs and spices. 3-Epiarmefolin is a constituent of Tanacetum vulgare (tansy) Constituent of Tanacetum vulgare (tansy). 3-Epiarmefolin is found in herbs and spices.

   

Alkhanol

[3S-(3alpha,3aalpha,5abeta,6alpha,8alpha,9bbeta)]-3a,4,5,5a,6,7,8,9b-Octahydro-6,8-dihydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2(3H)-one

C15H22O4 (266.1518)


Alkhanol is found in herbs and spices. Alkhanol is a constituent of Balsamita major (costmary) Constituent of Balsamita major (costmary). Alkhanol is found in tea and herbs and spices.

   

Cadabicilone

3,5a,9-trimethyl-octahydro-3H-naphtho[1,2-b]furan-2,8-dione

C15H22O3 (250.1569)


Cadabicilone is found in fruits. Cadabicilone is a constituent of the famine food Cadaba farinosa (luqata sigmama). Constituent of the famine food Cadaba farinosa (luqata sigmama). Cadabicilone is found in fruits.

   

1beta-Hydroxyalantolactone

[3aR-(3aalpha,5beta,8beta,8abeta,9aalpha)]-3a,5,6,7,8,8a,9,9a-Octahydro-8-hydroxy-5,8a-dimethyl-3-methylenenaphtho[2,3-b]furan-2(3H)-one

C15H20O3 (248.1412)


1beta-Hydroxyalantolactone is found in herbs and spices. 1beta-Hydroxyalantolactone is a constituent of Inula helenium (elecampane) Constituent of Inula helenium (elecampane). 1beta-Hydroxyalantolactone is found in herbs and spices. 1beta-Hydroxyalantolactone modulate many processes that influence inflammatory reactions[1]. 1beta-Hydroxyalantolactone modulate many processes that influence inflammatory reactions[1].

   

8-Epiisoivangustin

8-hydroxy-5,8a-dimethyl-3-methylidene-2H,3H,3aH,4H,4aH,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

C15H20O3 (248.1412)


8-Epiisoivangustin is found in herbs and spices. 8-Epiisoivangustin is a constituent of Inula helenium (elecampane) Constituent of Inula helenium (elecampane). 8-Epiisoivangustin is found in herbs and spices.

   

Cabbage identification factor 2

[3S-(3alpha,3aalpha,5abeta,6alpha,8alpha,9bbeta)]-3a,4,5,5a,6,7,8,9b-Octahydro-6,8-dihydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2(3H)-one

C15H12N4O3S (328.063)


Cabbage identification factor 2 is found in brassicas. Cabbage identification factor 2 is an alkaloid found on the leaf surfaces of Brassica oleracea cv. botrytis (cauliflower).

   

Tanacetin

[3aS-(3aalpha,5abeta,6beta,9aalpha,9bbeta)]-Decahydro-6,9a-dihydroxy-5a-methyl-3,9-bis(methylene)-naphtho[1,2-b]furan-2(3H)-one

C15H20O4 (264.1362)


Tanacetin is found in herbs and spices. Tanacetin is a constituent of Tanacetum vulgare (tansy) Constituent of Tanacetum vulgare (tansy). Tanacetin is found in herbs and spices.

   

Taraxacolide 1-O-b-D-glucopyranoside

3,5a,9-trimethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3H-naphtho[1,2-b]furan-2,8-dione

C21H32O9 (428.2046)


*Constituent of Taraxacum officinale (dandelion). Taraxacolide 1-O-b-D-glucopyranoside is found in many foods, some of which are coffee and coffee products, beverages, alcoholic beverages, and tea. Taraxacolide 1-O-b-D-glucopyranoside is found in alcoholic beverages. *Taraxacolide 1-O-b-D-glucopyranoside is a constituent of Taraxacum officinale (dandelion

   

1alpha-Hydroxyarbusculin A

[3aS-(3aalpha,5abeta,6beta,9alpha,9aalpha,9bbeta)]-Decahydro-6,9-dihydroxy-5a,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2(3H)-one

C15H22O4 (266.1518)


1alpha-Hydroxyarbusculin A is found in herbs and spices. 1alpha-Hydroxyarbusculin A is isolated from Tanacetum vulgare (tansy). Isolated from Tanacetum vulgare (tansy). 1alpha-Hydroxyarbusculin A is found in herbs and spices.

   

Alloalantolactone

[3aR-(3aalpha,8abeta,9aalpha)]-3a,4,6,7,8,8a,9,9a-Octahydro-5,8a-dimethyl-3-methylenenaphtho[2,3-b]furan-2(3H)-one

C15H20O2 (232.1463)


Alloalantolactone is found in herbs and spices. Alloalantolactone is a constituent of Inula helenium (elecampane) Constituent of Inula helenium (elecampane). Alloalantolactone is found in herbs and spices.

   

2-Oxo-5,11(13)-eudesmadien-12,8-olide

[3aR-(3aalpha,5beta,8abeta,9aalpha)]-3,3a,5,6,8,8a,9,9a-Octahydro-5,8a-dimethyl-3-methylenenaphtho[2,3-b]furan-2,7-dione

C15H18O3 (246.1256)


2-Oxo-5,11(13)-eudesmadien-12,8-olide is found in herbs and spices. 2-Oxo-5,11(13)-eudesmadien-12,8-olide is a constituent of Inula helenium (elecampane) Constituent of Inula helenium (elecampane). 2-Oxo-5,11(13)-eudesmadien-12,8-olide is found in herbs and spices.

   

Armexifolin

[3aS-(3aalpha,5abeta,6beta,9bbeta)]-3a,5,5a,6,7,9b-Hexahydro-6-hydroxy-5a,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2,8(3H,4H)-dione

C15H18O4 (262.1205)


Armexifolin is found in herbs and spices. Armexifolin is isolated from Tanacetum vulgare (tansy Isolated from Tanacetum vulgare (tansy). Armexifolin is found in herbs and spices.

   

(1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide

8,9a-dihydroxy-3,5,8a-trimethyl-2H,4H,4aH,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

C15H20O4 (264.1362)


(1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide is found in green vegetables. (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide is a constituent of Smyrnium olusatrum (alexanders) Constituent of Smyrnium olusatrum (alexanders). (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide is found in green vegetables.

   

Cepagenin

5,7,9,13-tetramethyl-5-oxaspiro[oxane-2,6-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18-ene-4,14,16-triol

C27H42O5 (446.3032)


Cepagenin is found in onion-family vegetables. Genin isloated from Allium cepa (onion

   

Phyllanthusol A

N-{2-[(6-{[3,3a,4-trihydroxy-4-(4-hydroxybenzoyloxy)-5-methyl-hexahydro-3H-spiro[1-benzofuran-2,2-oxane]-6-yl]carbonyloxy}-2,3,4-trihydroxycyclohexyl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidate

C35H49NO19 (787.2899)


Phyllanthusol A is found in fruits. Phyllanthusol A is a constituent of Phyllanthus acidus (otaheite gooseberry) Constituent of Phyllanthus acidus (otaheite gooseberry). Phyllanthusol A is found in fruits.

   

Artemisin

4-hydroxy-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione

C15H18O4 (262.1205)


D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides

   

Atractylenolide II

3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

C15H20O2 (232.1463)


   

Atractylenolide III

9a-hydroxy-3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

C15H20O3 (248.1412)


   

Taurin

3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9bH-naphtho[1,2-b]furan-2,6-dione

C15H20O3 (248.1412)


   

Sesquiterpenes

(3R,3aS,5aR,9bR)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione

C15H18O3 (246.1256)


Sesquiterpenes belongs to eudesmanolides, secoeudesmanolides, and derivatives class of compounds. Those are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Sesquiterpenes is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Sesquiterpenes is a bitter tasting compound found in ceylon cinnamon, pepper (spice), and potato, which makes sesquiterpenes a potential biomarker for the consumption of these food products. Sesquiterpenes are a class of terpenes that consist of three isoprene units and have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be acyclic or contain rings, including many unique combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids . Santonin is an active principle of the plant Artemisia cina, which is formely used to treat worms[1]. Santonin is an active principle of the plant Artemisia cina, which is formely used to treat worms[1].

   

Reynosin

6-hydroxy-5a-methyl-3,9-dimethylidene-dodecahydronaphtho[1,2-b]furan-2-one

C15H20O3 (248.1412)


Reynosin belongs to eudesmanolides, secoeudesmanolides, and derivatives class of compounds. Those are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Reynosin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Reynosin can be found in sweet bay, which makes reynosin a potential biomarker for the consumption of this food product.

   

Ridentin B

6,8-Dihydroxy-5a-methyl-3,9-dimethylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one

C15H20O4 (264.1362)


Ridentin b belongs to eudesmanolides, secoeudesmanolides, and derivatives class of compounds. Those are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Ridentin b is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Ridentin b can be found in sweet bay, which makes ridentin b a potential biomarker for the consumption of this food product.

   

Rothin B

4,9a-dihydroxy-5a-methyl-3,9-dimethylidene-hexahydro-3aH-naphtho[1,2-b]furan-2-one

C15H20O4 (264.1362)


Rothin b belongs to eudesmanolides, secoeudesmanolides, and derivatives class of compounds. Those are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Rothin b is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Rothin b can be found in sweet bay, which makes rothin b a potential biomarker for the consumption of this food product.

   

Cichoriolide A

8-hydroxy-5a,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9bH-naphtho[1,2-b]furan-2-one

C15H20O3 (248.1412)


Cichoriolide a belongs to eudesmanolides, secoeudesmanolides, and derivatives class of compounds. Those are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Cichoriolide a is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cichoriolide a can be found in chicory, which makes cichoriolide a a potential biomarker for the consumption of this food product.

   

Sonchuside C

3,5a,9-trimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9bH-naphtho[1,2-b]furan-2-one

C21H32O8 (412.2097)


Sonchuside c belongs to eudesmanolides, secoeudesmanolides, and derivatives class of compounds. Those are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Sonchuside c is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Sonchuside c can be found in chicory, which makes sonchuside c a potential biomarker for the consumption of this food product.