Classification Term: 1544

Guaianolides and derivatives (ontology term: CHEMONTID:0001770)

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." [DOI:10.1007/BF02919190, DOI:10.3109/10408444.2013.813905]

found 33 associated metabolites at family metabolite taxonomy ontology rank level.

Ancestor: Sesquiterpene lactones

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

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 (346.1416312)


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.

   

Eremanthin

(3aS,6aR,9aR,9bS)-6-methyl-3,9-dimethylidene-2H,3H,3aH,4H,6aH,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-2-one

C15H18O2 (230.1306728)


Eremanthin 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. Eremanthin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Eremanthin can be found in sweet bay, which makes eremanthin a potential biomarker for the consumption of this food product.

   

Artecanin

(1R,2R,5S,9S,10S,11S,13R,14S)-2-hydroxy-2,11-dimethyl-6-methylidene-8,12,15-trioxapentacyclo[8.5.0.0¹,¹⁴.0⁵,⁹.0¹¹,¹³]pentadecan-7-one

C15H18O5 (278.1154178)


Artecanin 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. Artecanin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Artecanin can be found in sweet bay, which makes artecanin a potential biomarker for the consumption of this food product.

   

4-Epiisoinuviscolide

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

C15H20O3 (248.14123700000002)


4-Epiisoinuviscolide is found in herbs and spices. 4-Epiisoinuviscolide is a constituent of Inula helenium (elecampane) Constituent of Inula helenium (elecampane). 4-Epiisoinuviscolide is found in herbs and spices.

   

Arlatin

6,6a-dihydroxy-3,6,9-trimethyl-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

C15H22O4 (266.1518012)


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

   

Annuolide G

6-Hydroxy-6,9-dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,6H,6ah,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl (2E)-2-methylbut-2-enoic acid

C20H26O5 (346.17801460000004)


Annuolide G is found in fats and oils. Annuolide G is a constituent of Helianthus annuus (sunflower) Constituent of Helianthus annuus (sunflower). Annuolide G is found in fats and oils.

   

Isoamberboin

4-hydroxy-3,9-dimethyl-6-methylidene-octahydro-3H-azuleno[4,5-b]furan-2,8-dione

C15H20O4 (264.13615200000004)


Constituent of Cynara scolymus (artichoke). Isoamberboin is found in globe artichoke and green vegetables. Isoamberboin is found in globe artichoke. Isoamberboin is a constituent of Cynara scolymus (artichoke)

   

3beta-20(29)-Lupene-3,27-diol

2-(hydroxymethyl)-1,5,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol

C30H50O2 (442.38106)


3beta-20(29)-Lupene-3,27-diol is found in fats and oils. 3beta-20(29)-Lupene-3,27-diol is a constituent of Sapium sebiferum (Chinese tallowtree)

   

4,5-Epoxy-11(13)-guaien-12,8-olide

9,13-dimethyl-4-methylidene-6,14-dioxatetracyclo[8.4.0.0¹,¹³.0³,⁷]tetradecan-5-one

C15H20O3 (248.14123700000002)


4,5-Epoxy-11(13)-guaien-12,8-olide is found in herbs and spices. 4,5-Epoxy-11(13)-guaien-12,8-olide is a constituent of Inula helenium (elecampane) Constituent of Inula helenium (elecampane). 4,5-Epoxy-11(13)-guaien-12,8-olide is found in herbs and spices.

   

8-Deoxy-11,13-dihydroxygrosheimin

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

C15H20O5 (280.13106700000003)


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.

   

Cichoralexin

3,6,9-trimethyl-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

C15H20O3 (248.14123700000002)


Constituent of Cichorium intybus (chicory) inoculated with Pseudomonas cichorii. Cichoralexin is found in chicory, herbs and spices, and green vegetables. Cichoralexin is found in chicory. Cichoralexin is a constituent of Cichorium intybus (chicory) inoculated with Pseudomonas cichorii.

   

Scorzoside

3-methyl-6,9-dimethylidene-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

C21H30O8 (410.194058)


Constituent of Scorzonera hispanica (scorzonera). Scorzoside is found in coffee and coffee products and root vegetables. Scorzoside is found in coffee and coffee products. Scorzoside is a constituent of Scorzonera hispanica (scorzonera).

   

alpha-Peroxyachifolide

3-Hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8,12,13-trioxatetracyclo[9.2.2.0¹,¹⁰.0⁵,⁹]pentadec-14-en-2-yl (2E)-2-methylbut-2-enoic acid

C20H24O7 (376.1521954)


alpha-Peroxyachifolide is found in herbs and spices. alpha-Peroxyachifolide is a constituent of Achillea millefolium (yarrow). Constituent of Achillea millefolium (yarrow). alpha-Peroxyachifolide is found in herbs and spices.

   

Cynaroside A

3-hydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3aH-azuleno[4,5-b]furan-2-one

C21H32O10 (444.1995372)


Cynaroside A is found in herbs and spices. Cynaroside A is a constituent of Cynara cardunculus (cardoon). Constituent of Cynara cardunculus (cardoon). Cynaroside A is found in herbs and spices.

   

Dehydrocyanaropicrin

3,6,9-Trimethylidene-2,8-dioxo-dodecahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoic acid

C19H20O6 (344.125982)


Dehydrocyanaropicrin is found in globe artichoke. Dehydrocyanaropicrin is a constituent of Cynara scolymus (artichoke) Constituent of Cynara scolymus (artichoke). Dehydrocyanaropicrin is found in globe artichoke and root vegetables.

   

Annuolide E

5-hydroxy-3-methyl-6,9-dimethylidene-octahydro-3H-azuleno[4,5-b]furan-2-one

C15H20O3 (248.14123700000002)


Annuolide D is found in fats and oils. Annuolide D is a constituent of Helianthus annuus (sunflower). Constituent of Helianthus annuus (sunflower). Annuolide D is found in fats and oils.

   

Annuolide A

9-(hydroxymethyl)-3,6-dimethylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

C15H18O3 (246.1255878)


Annuolide A is found in fats and oils. Annuolide A is a constituent of Helianthus annuus (sunflower). Constituent of Helianthus annuus (sunflower). Annuolide A is found in fats and oils.

   

Cynaratriol

3,8-dihydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-octahydro-3aH-azuleno[4,5-b]furan-2-one

C15H22O5 (282.1467162)


Constituent of Cynara cardunculus (cardoon) and Cynara scolymus (globe artichoke). Cynaratriol is found in many foods, some of which are cardoon, globe artichoke, green vegetables, and herbs and spices. Cynaratriol is found in cardoon. Cynaratriol is a constituent of Cynara cardunculus (cardoon) and Cynara scolymus (globe artichoke)

   

8-Deoxy-11-hydroxy-13-chlorogrosheimin

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

C15H19ClO4 (298.0971804)


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

   

Absindiol

4,8-dihydroxy-3,6-dimethyl-9-methylidene-dodecahydroazuleno[4,5-b]furan-2-one

C15H22O4 (266.1518012)


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

   

Dihydrocumambrin A

6-Hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3ah,4H,5H,6H,6ah,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl acetic acid

C17H24O5 (308.1623654)


Dihydrocumambrin A is found in garland chrysanthemum. Dihydrocumambrin A is from Chrysanthemum coronarium (chop-suey greens). From Chrysanthemum coronarium (chop-suey greens). Dihydrocumambrin A is found in garland chrysanthemum and herbs and spices.

   

Annuolide C

5-hydroxy-3,6,9-trimethylidene-dodecahydroazuleno[4,5-b]furan-2-one

C15H18O3 (246.1255878)


Annuolide C is found in fats and oils. Annuolide C is a constituent of Helianthus annuus (sunflower). Constituent of Helianthus annuus (sunflower). Annuolide C is found in fats and oils.

   

Annuolide B

9-(hydroxymethyl)-3-methyl-6-methylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

C15H20O3 (248.14123700000002)


Annuolide B is found in fats and oils. Annuolide B is a constituent of Helianthus annuus (sunflower). Constituent of Helianthus annuus (sunflower). Annuolide B is found in fats and oils.

   

3,12-Dimethyl-7-methylidene-2,9-dioxatetracyclo[9.3.0.01,3.06,10]tetradec-12-en-8-one

3,12-Dimethyl-7-methylidene-2,9-dioxatetracyclo[9.3.0.01,3.06,10]tetradec-12-en-8-one

C15H18O3 (246.1255878)


   

Canin

2-hydroxy-2,11-dimethyl-6-methylidene-8,12,15-trioxapentacyclo[8.5.0.0¹,¹⁴.0⁵,⁹.0¹¹,¹³]pentadecan-7-one

C15H18O5 (278.1154178)


   

Dehydrocostus lactone

3,6,9-trimethylidene-dodecahydroazuleno[4,5-b]furan-2-one

C15H18O2 (230.1306728)


Dehydrocostus lactone, also known as dehydro-alpha-curcumene, 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. Dehydrocostus lactone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dehydrocostus lactone can be found in burdock and sweet bay, which makes dehydrocostus lactone a potential biomarker for the consumption of these food products.

   

3beta-Chlorodehydrocostuslactone

(3Abeta,6abeta,9abeta,9balpha)-3,6,9-trismethylene-8a-chlorododecahydroazuleno[4,5-b]furan-2-one

C15H17ClO2 (264.0917012)


3beta-chlorodehydrocostuslactone 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. 3beta-chlorodehydrocostuslactone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3beta-chlorodehydrocostuslactone can be found in sweet bay, which makes 3beta-chlorodehydrocostuslactone a potential biomarker for the consumption of this food product.

   

Dehydrodihydrocostus lactone

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

C15H20O2 (232.14632200000003)


Dehydrodihydrocostus lactone 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. Dehydrodihydrocostus lactone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dehydrodihydrocostus lactone can be found in burdock, which makes dehydrodihydrocostus lactone a potential biomarker for the consumption of this food product.

   

Lappaphen A

3-hydroxy-6,9-dimethylidene-3-(2-oxo-2-{5-[5-(prop-1-yn-1-yl)thiophen-2-yl]thiophen-2-yl}ethyl)-dodecahydroazuleno[4,5-b]furan-2-one

C27H26O4S2 (478.12724360000004)


Lappaphen b 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. Lappaphen b is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Lappaphen b can be found in burdock, which makes lappaphen b a potential biomarker for the consumption of this food product.

   

Viscidulin C

7-hydroxy-5,14-dimethyl-9-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-4-one

C15H20O4 (264.13615200000004)


Viscidulin c 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. Viscidulin c is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Viscidulin c can be found in sweet bay, which makes viscidulin c a potential biomarker for the consumption of this food product.

   

Zaluzanin D

[(3aS,6aS,8S,9aR,9bS)-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl] acetate

C17H20O4 (288.13615200000004)


Zaluzanin d 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. Zaluzanin d is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Zaluzanin d can be found in sweet bay, which makes zaluzanin d a potential biomarker for the consumption of this food product.

   

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 (262.1205028)


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.

   

Cumambrin A

6-Hydroxy-6,9-dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,6H,6ah,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl acetic acid

C17H22O5 (306.1467162)


Cumambrin a 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. Cumambrin a is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Cumambrin a can be found in sweet bay, which makes cumambrin a a potential biomarker for the consumption of this food product.