Classification Term: 1539

Diterpene lactones (ontology term: CHEMONTID:0001538)

Diterpenoids containing a lactone moiety." []

found 37 associated metabolites at category metabolite taxonomy ontology rank level.

Ancestor: Terpene lactones

Child Taxonomies: Ginkgolides and bilobalides, Cembranolides

Carnosol

2H-9,4A-(EPOXYMETHANO)PHENANTHREN-12-ONE, 1,3,4,9,10,10A-HEXAHYDRO-5,6-DIHYDROXY-1,1-DIMETHYL-7-(1-METHYLETHYL)-, (4AR-(4A.ALPHA.,9.ALPHA.,10A.BETA.))-

C20H26O4 (330.18309960000005)


Carnosol is a naturally occurring phenolic diterpene found in rosemary (Rosemarinus officinalis, Labiatae). It has been known that an extract of rosemary leaves contains high antioxidative activity. Ninety percent of this antioxidative activity can be attributed to carnosol and carnosic acid. Carnosic acid is easily converted to carnosol by oxidation. Carnosol has multiple beneficial medicinal effects including anti-inflammatory, anti-microbial and anti-cancer activities in various disease models. Carnosol may possess important neuroprotective effects against rotenone-induced DA neuronal damage. Naturally occurring antioxidants reduce the risk of neurodegenerative diseases. In addition, carnosol and carnosic acid promoted the synthesis of nerve growth factor in glial cells. Carnosol-mediated neuroprotection in DA neurons is involved in the attenuation of caspase-3 activity, which was induced by rotenone. Furthermore, carnosol-mediated tyrosine hydroxylase (TH) increase, which is dependent on the Raf-mitogen-activated protein kinase (MEK)-extracellular signal-regulated kinase (ERK)1/2 signaling pathway, is responsible for the neuroprotection in SN4741 DA cells. (PMID: 17047462). Carnosol, a phenolic diterpene compound of the labiate herbs rosemary and sage, is an activator of the human peroxisome proliferator-activated receptor gamma (PPARgamma), a ligand activated transcription factor, belonging to the metazoan family of nuclear hormone receptors. Activation of PPARgamma increases the transcription of enzymes involved in primary metabolism, leading to lower blood levels of fatty acids and glucose. Hence, PPARgamma represents the major target for the glitazone type of drugs currently being used clinically for the treatment of type 2 diabetes. (PMID: 16858665). Bitter principle in Salvia carnosa, Salvia officinalis (sage), Salvia triloba (Greek sage) and Rosmarinus officinalis (rosemary). Nutriceutical with anticancer props. Carnosol is a diterpenoid. Carnosol is a natural product found in Podocarpus rumphii, Lepechinia salviae, and other organisms with data available.

   

ent-7alpha,12beta-Dihydroxy-16-kauren-19,6beta-olide

4,9-dihydroxy-1,13-dimethyl-6-methylidene-11-oxapentacyclo[8.6.1.1⁵,⁸.0²,⁸.0¹³,¹⁷]octadecan-12-one

C20H28O4 (332.19874880000003)


ent-7alpha,12beta-Dihydroxy-16-kauren-19,6beta-olide is found in fruits. ent-7alpha,12beta-Dihydroxy-16-kauren-19,6beta-olide is a constituent of the seeds of Cucurbita pepo and Cucurbita maxima. Constituent of the seeds of Cucurbita pepo and Cucurbita maxima. ent-7alpha,12beta-Dihydroxy-16-kauren-19,6beta-olide is found in fruits and japanese pumpkin.

   

Tanabalin

2-{7,8-dimethyl-3-oxo-1H,3H,5H,6H,6ah,7H,8H,9H,10H-naphtho[4,4a-c]furan-7-yl}-1-(furan-3-yl)ethyl acetic acid

C22H28O5 (372.1936638)


Tanabalin is found in herbs and spices. Tanabalin is a constituent of Tanacetum balsamita (costmary). Constituent of Tanacetum balsamita (costmary). Tanabalin is found in tea and herbs and spices.

   

7-Methylrosmanol

(1R,8S,9S,10S)-3,4-dihydroxy-8-methoxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[7.5.2.0^{1,10.0^{2,7]hexadeca-2,4,6-trien-15-one

C21H28O5 (360.1936638)


7-Methylrosmanol is a diterpene lactone. 7-Methylrosmanol is a natural product found in Salvia officinalis and Salvia canariensis with data available. From aerial parts of rosemary (Rosmarinus officinalis). 7-Methylrosmanol is found in herbs and spices, rosemary, and common sage. 7-Methylrosmanol is found in common sage. 7-Methylrosmanol is from aerial parts of rosemary (Rosmarinus officinalis 7-Methoxyrosmanol (7-O-Methoxyrosmanol), a phenolic diterpene isolated from rosemary, suppresses the cAMP responsiveness of PEPCK and G6Pase promoters[1]. 7-Methoxyrosmanol (7-O-Methoxyrosmanol), a phenolic diterpene isolated from rosemary, suppresses the cAMP responsiveness of PEPCK and G6Pase promoters[1].

   

Pinusolide

1-Naphthalenecarboxylic acid, 5-[2-(2,5-dihydro-2-oxo-3-furanyl)ethyl]decahydro-1,4a-dimethyl-6-methylene-, methyl ester, [1S-(1,4a,5,8a)]-; Labda-8(20),13-diene-16,19-dioic acid, 15-hydroxy-, -lactone, methyl ester

C21H30O4 (346.214398)


Pinusolide is a diterpene lactone. It has a role as a metabolite. Pinusolide is a natural product found in Agathis macrophylla, Platycladus orientalis, and other organisms with data available. Pinusolide is found in fruits. Pinusolide is a constituent of the oleorosin of Pinus koraiensis (Korean pine) A natural product found in Biota orientalis.

   

Isorosmanol

3,4,9-trihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one

C20H26O5 (346.17801460000004)


Constituent of Rosmarinus officinalis (rosemary). Isorosmanol is found in herbs and spices, rosemary, and common sage. Isorosmanol is found in common sage. Isorosmanol is a constituent of Rosmarinus officinalis (rosemary)

   

Epirosmanol

3,4,8-trihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one

C20H26O5 (346.17801460000004)


From rosemary leaves (Rosmarinus officinalis). Epirosmanol is found in many foods, some of which are cloves, pepper (spice), sweet bay, and caraway. Rosmanol is found in common sage. Rosmanol is isolated from rosemary leaves (Rosmarinus officinalis Epirosmanol is a nature diterpene lactone from S. officinalis. Epirosmanol shows anti-cancer activity and inhibits melanin biosynthesis against melanoma cells. Epirosmanol also exhibits DPPH radical scavenging activity[1][2].

   

Oryzalide A

5H-1b,10-Methanooxireno[6,7]cyclohepta[1,2-h][2]benzopyran-5-one, dodecahydro-7-hydroxy-4,4,7a,10a-tetramethyl-, (1aS,1bS,3aR,7S,7aR,7bS,10S,10aR)-

C19H28O4 (320.19874880000003)


Oryzalide A is found in cereals and cereal products. Oryzalide A is isolated from rice leaves. Isolated from rice leaves. Oryzalide A is found in cereals and cereal products.

   

11,12-Dimethylrosmanol

8-hydroxy-3,4-dimethoxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one

C22H30O5 (374.209313)


11,12-Dimethylrosmanol is found in beverages. 11,12-Dimethylrosmanol is a constituent of Salvia columbariae (California chia). Constituent of Salvia columbariae (California chia). 11,12-Dimethylrosmanol is found in herbs and spices and beverages.

   

Sagequinone methide A

3-hydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,5,7-triene-4,15-dione

C20H24O4 (328.1674504)


Constituent of Salvia officinalis (sage). Sagequinone methide A is found in tea, herbs and spices, and common sage. Sagequinone methide A is found in common sage. Sagequinone methide A is a constituent of Salvia officinalis (sage)

   

Momilactone C

5-ethenyl-14-hydroxy-1,5,12-trimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-7-en-11-one

C20H28O3 (316.2038338)


Momilactone C is found in cereals and cereal products. Momilactone C is a constituent of Oryza sativa (rice). Constituent of Oryza sativa (rice). Momilactone C is found in cereals and cereal products and rice.

   

Columbaridione

4-hydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),4-diene-3,6,15-trione

C20H24O5 (344.1623654)


Constituent of Salvia columbariae (California chia). Columbaridione is found in herbs and spices, beverages, and common sage. Columbaridione is found in beverages. Columbaridione is a constituent of Salvia columbariae (California chia).

   

Oryzalide B

8,15-dihydroxy-5,5,9-trimethyl-14-methylidene-7-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-one

C19H28O4 (320.19874880000003)


Oryzalide B is found in cereals and cereal products. Oryzalide B is isolated from rice leaves. Isolated from rice leaves. Oryzalide B is found in cereals and cereal products.

   

11,12,14-Trihydroxy-7-methoxy-8,11,13-abietatrien-20,6-olide

3,4,6-trihydroxy-8-methoxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one

C21H28O6 (376.1885788)


11,12,14-Trihydroxy-7-methoxy-8,11,13-abietatrien-20,6-olide is found in herbs and spices. 11,12,14-Trihydroxy-7-methoxy-8,11,13-abietatrien-20,6-olide is a constituent of leaves of rosemary (Rosmarinus officinalis) Constituent of leaves of rosemary (Rosmarinus officinalis). 14-Hydroxy-7-methylrosmanol is found in herbs and spices.

   

Diosbulbin F

Methyl 2-(furan-3-yl)-9-hydroxy-10b-methyl-4,6-dioxo-dodecahydro-1H-naphtho[2,1-c]pyran-7-carboxylic acid

C20H24O7 (376.1521954)


Diosbulbin F is found in root vegetables. Diosbulbin F is isolated from Dioscorea bulbifera (air potato). Isolated from Dioscorea bulbifera (air potato). Diosbulbin F is found in root vegetables.

   

11,12-Dihydroxy-7,14-dimethoxy-8,11,13-abietatrien-20,6-olide

3,4-dihydroxy-6,8-dimethoxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one

C22H30O6 (390.204228)


11,12-Dihydroxy-7,14-dimethoxy-8,11,13-abietatrien-20,6-olide is found in herbs and spices. 11,12-Dihydroxy-7,14-dimethoxy-8,11,13-abietatrien-20,6-olide is a constituent of leaves of rosemary (Rosmarinus officinalis) Constituent of leaves of rosemary (Rosmarinus officinalis). 14-Methoxy-7-methylrosmanol is found in herbs and spices.

   

7,18-Dihydroxykaurenolide

9-hydroxy-13-(hydroxymethyl)-1-methyl-6-methylidene-11-oxapentacyclo[8.6.1.1⁵,⁸.0²,⁸.0¹³,¹⁷]octadecan-12-one

C20H28O4 (332.19874880000003)


7,18-Dihydroxykaurenolide is found in cereals and cereal products. 7,18-Dihydroxykaurenolide is produced by Gibberella fujikuroi, present in barley during germination. Production by Gibberella fujikuroi, present in barley during germination. 7,18-Dihydroxykaurenolide is found in cereals and cereal products.

   

6,7-Dimethoxy-7-epirosmanol

3,4-dihydroxy-8,9-dimethoxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one

C22H30O6 (390.204228)


6,7-Dimethoxy-7-epirosmanol is found in herbs and spices. 6,7-Dimethoxy-7-epirosmanol is a constituent of Salvia officinalis (sage) Constituent of Salvia officinalis (sage). 6,7-Dimethoxy-7-epirosmanol is found in tea and herbs and spices.

   

Diosbulbin H

Butyl 2-(furan-3-yl)-9-hydroxy-10b-methyl-4,6-dioxo-dodecahydro-1H-naphtho[2,1-c]pyran-7-carboxylic acid

C23H30O7 (418.199143)


Diosbulbin H is found in root vegetables. Diosbulbin H is isolated from Dioscorea bulbifera (air potato). Isolated from Dioscorea bulbifera (air potato). Diosbulbin H is found in root vegetables.

   

Rosmaricine

8-amino-3,4-dihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one

C20H27NO4 (345.19399820000007)


Rosmaricine is found in herbs and spices. Rosmaricine is isolated from rosemary (Rosmarinus officinalis) using NH3 during extraction. Isolated from rosemary (Rosmarinus officinalis) using NH3 during extraction. Rosmaricine is found in herbs and spices and rosemary.

   

Hovenidulcigenin A

3-{7-hydroxy-4b,8,8,10a-tetramethyl-5-oxo-dodecahydro-2H-spiro[oxolane-3,1-phenanthrene]-2-yl}-1-(4-methyl-5-oxo-2,5-dihydrofuran-2-yl)butan-2-yl acetic acid

C32H48O7 (544.3399858)


Sapogenin from Hovenia dulcis (raisin tree). Sapogenin from Hovenia dulcis (raisin tree)

   

Hovenidulcigenin B

3-{7-hydroxy-4b,8,8,10a-tetramethyl-5-oxo-dodecahydro-2H-spiro[oxolane-3,1-phenanthrene]-2-yl}-1-(4-methyl-5-oxooxolan-2-yl)butan-2-yl acetic acid

C32H50O7 (546.355635)


Sapogenin from Hovenia dulcis (raisin tree). Sapogenin from Hovenia dulcis (raisin tree)

   

Pseudolaric acid-B

5-[7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-9-yl]-2-methylpenta-2,4-dienoic acid

C23H28O8 (432.1784088)


   

12-Epi-Salvinorin A

2-(3-Furyl)-4,10-dioxo-6a,10b-dimethyl-9-acetoxydodecahydro-4H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

C23H28O8 (432.1784088)


   

14-Deoxy-11,12-didehydroandrographolide

3-{2-[6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethenyl}-2,5-dihydrofuran-2-one

C20H28O4 (332.19874880000003)


   

14-Deoxyandrographolide

3-{2-[6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethyl}-2,5-dihydrofuran-2-one

C20H30O4 (334.214398)


   

1-Deoxo-1,10-dehydrosalvinorin A

methyl 9-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4-oxo-1H,2H,4H,4aH,5H,6H,6aH,7H,8H,9H,10bH-naphtho[2,1-c]pyran-7-carboxylate

C23H28O7 (416.1834938)


   

Dehydroandrographolide succinate

4-[(1-{[(3-carboxypropanoyl)oxy]methyl}-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-2,5-dihydrofuran-3-yl)ethenyl]-decahydronaphthalen-2-yl)oxy]-4-oxobutanoic acid

C28H36O10 (532.2308356)


   

Dehydrocrotonin

5-(furan-3-yl)-2,5-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-spiro[naphthalene-1,3-oxolane]-2,7-dione

C19H22O4 (314.1518012)


   

manoalide

5-hydroxy-4-{6-hydroxy-5-[4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl}-2,5-dihydrofuran-2-one

C25H36O5 (416.2562606)


   

Gibberellin A4 methyl ester

Gibbane-1,10-dicarboxylic acid, 2,4a-dihydroxy-1-methyl-8-methylene-, 1,4a-lactone, 10-methyl ester, (1alpha,2beta,4aalpha,4bbeta,10beta)-

C20H26O5 (346.17801460000004)


   

Mycolactone

12-(7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl)-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl 12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate

C44H70O9 (742.5019570000001)


   

Nodosin

9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione

C20H26O6 (362.17292960000003)


   

Petrosaspongiolide m

[3-(2-hydroxy-5-oxo-2H-furan-3-yl)-4b,7,7,10a-tetramethyl-1,3,4,4a,5,6,6a,8,9,10,10b,11,12,12a-tetradecahydronaphtho[2,1-f]isochromen-1-yl] acetate

C27H40O6 (460.28247400000004)


   

5

3-propyl-6-[(4E,7E,10E,12E,18E)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]-2H-pyran-2-one

C34H52O5 (540.3814542)


5 is a member of the class of compounds known as diterpene lactones. Diterpene lactones are diterpenoids containing a lactone moiety. 5 is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 5 can be found in roman camomile, which makes 5 a potential biomarker for the consumption of this food product. 5 is a non-carcinogenic (not listed by IARC) potentially toxic compound. 5 (five ) is a number, numeral, and glyph. It is the natural number following 4 and preceding 6 . Manganese mainly affects the nervous system and may cause behavioral changes and other nervous system effects, which include movements that may become slow and clumsy. This combination of symptoms when sufficiently severe is referred to as ‚Äúmanganism‚Äù (L228) (T3DB). 5 is a member of the class of compounds known as diterpene lactones. Diterpene lactones are diterpenoids containing a lactone moiety. 5 is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 5 can be found in roman camomile, which makes 5 a potential biomarker for the consumption of this food product. 5 is a non-carcinogenic (not listed by IARC) potentially toxic compound. 5 (five ) is a number, numeral, and glyph. It is the natural number following 4 and preceding 6 . Manganese mainly affects the nervous system and may cause behavioral changes and other nervous system effects, which include movements that may become slow and clumsy. This combination of symptoms when sufficiently severe is referred to as “manganism” (L228) (T3DB).

   

N-Methylrosmaricine

3,4-dihydroxy-11,11-dimethyl-8-(methylamino)-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one

C21H29NO4 (359.20964740000005)


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

   

7-Ethylrosmanol

8-ethoxy-3,4-dihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one

C22H30O5 (374.209313)


7-ethylrosmanol is a member of the class of compounds known as diterpene lactones. Diterpene lactones are diterpenoids containing a lactone moiety. 7-ethylrosmanol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 7-ethylrosmanol can be found in common sage and rosemary, which makes 7-ethylrosmanol a potential biomarker for the consumption of these food products.