Classification Term: 1668

Kaurane diterpenoids (ontology term: CHEMONTID:0003782)

Diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D." [ASIN:B001D4CV7M, DOI:10.1039/b604174d, ISBN:9780124695597, ISBN:9780412466205]

found 59 associated metabolites at category metabolite taxonomy ontology rank level.

Ancestor: Diterpenoids

Child Taxonomies: Veatchine-type diterpenoid alkaloids, Napelline-type diterpenoid alkaloids

Steviol

(4R,4aS,6aR,9S,11aR,11bS)-9-hydroxy-4,11b-dimethyl-8-methylenetetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid

C20H30O3 (318.21948299999997)


Steviol is an ent-kaurane diterpenoid that is 5beta,8alpha,9beta,10alpha-kaur-16-en-18-oic acid in which the hydrogen at position 13 has been replaced by a hydroxy group. It has a role as an antineoplastic agent. It is a tetracyclic diterpenoid, a tertiary allylic alcohol, a monocarboxylic acid, a bridged compound and an ent-kaurane diterpenoid. It is a conjugate acid of a steviol(1-). Steviol is a natural product found in Ceriops decandra, Cucurbita, and other organisms with data available. Steviol is found in fruits. Steviol is isolated from Cucurbita maxima Rebaudioside B, D, and E may also be present in minute quantities; however, it is suspected that rebaudioside B is a byproduct of the isolation technique. The two majority compounds stevioside and rebaudioside, primarily responsible for the sweet taste of stevia leaves, were first isolated by two French chemists in 1931. Isolated from Cucurbita maxima Steviol is a major metabolite of the sweetening compound stevioside. Steviol slows renal cyst growth by reducing AQP2 expression and promoting AQP2 degradation[1]. Steviol is a major metabolite of the sweetening compound stevioside. Steviol slows renal cyst growth by reducing AQP2 expression and promoting AQP2 degradation[1].

   

(-)-Kaur-16-en-19-oic acid

(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

C20H30O2 (302.224568)


(-)-kaur-16-en-19-oic acid, also known as ent-kaurenoic acid or ent-kaur-16-en-19-oate, is a member of the class of compounds known as kaurane diterpenoids. Kaurane diterpenoids are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D (-)-kaur-16-en-19-oic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (-)-kaur-16-en-19-oic acid can be found in sugar apple and sunflower, which makes (-)-kaur-16-en-19-oic acid a potential biomarker for the consumption of these food products. Kaurenoic acid is a diterpene from Sphagneticola trilobata, inhibits Inflammatory Pain by the inhibition of cytokine production and activation of the NO–cyclic GMP–PKG–ATP-sensitive potassium channel signaling pathway[1]. Kaurenoic acid is a diterpene from Sphagneticola trilobata, inhibits Inflammatory Pain by the inhibition of cytokine production and activation of the NO–cyclic GMP–PKG–ATP-sensitive potassium channel signaling pathway[1].

   

dTDP-4-dehydro-6-deoxy-beta-L-mannose

{[(2R,3R,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy}({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphinic acid

C16H24N2O15P2 (546.0651894)


Dtdp-4-dehydro-6-deoxy-beta-l-mannose, also known as dtdp-4-oxo-L-rhamnose or dtdp-6-deoxy-beta-L-lyxo-hex-4-ulose, is a member of the class of compounds known as pyrimidine nucleotide sugars. Pyrimidine nucleotide sugars are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Dtdp-4-dehydro-6-deoxy-beta-l-mannose is soluble (in water) and a moderately acidic compound (based on its pKa). Dtdp-4-dehydro-6-deoxy-beta-l-mannose can be found in a number of food items such as rose hip, white cabbage, fennel, and shallot, which makes dtdp-4-dehydro-6-deoxy-beta-l-mannose a potential biomarker for the consumption of these food products. Dtdp-4-dehydro-6-deoxy-β-l-mannose, also known as dtdp-4-oxo-L-rhamnose or dtdp-6-deoxy-beta-L-lyxo-hex-4-ulose, is a member of the class of compounds known as pyrimidine nucleotide sugars. Pyrimidine nucleotide sugars are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Dtdp-4-dehydro-6-deoxy-β-l-mannose is soluble (in water) and a moderately acidic compound (based on its pKa). Dtdp-4-dehydro-6-deoxy-β-l-mannose can be found in a number of food items such as rose hip, white cabbage, fennel, and shallot, which makes dtdp-4-dehydro-6-deoxy-β-l-mannose a potential biomarker for the consumption of these food products.

   

ent-16-Kaurene

(4R,9R,10R,13R)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane

C20H32 (272.2503872)


Phyllocladene is found in fats and oils. Phyllocladene is a constituent of sunflower oil.

   

Candol B

[(1S,4S,5S,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-5-yl]methanol

C20H32O (288.24530219999997)


Candol B, also known as 4beta-kaur-16-en-19-ol, belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by the cyclization of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Candol B is an extremely weak basic (essentially neutral) compound (based on its pKa). Candol B is found in cereals and cereal products. Candol B is a constituent of barley. Constituent of barley. Candol B is found in cereals and cereal products.

   

ent-Kaur-16-en-19-al

(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carbaldehyde

C20H30O (286.229653)


ent-16-Kauren-19-al is found in fruits. ent-16-Kauren-19-al is a constituent of the root of Annona squamosa (sugar apple).

   

(ent-6alpha,7alpha)-6,7-Dihydroxy-16-kauren-19-oic acid

2,3-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

C20H30O4 (334.214398)


(ent-6alpha,7alpha)-6,7-Dihydroxy-16-kauren-19-oic acid is found in fruits. (ent-6alpha,7alpha)-6,7-Dihydroxy-16-kauren-19-oic acid is produced by Cucurbita maxima and in cell-free systems of other plants. Production by Cucurbita maxima and in cell-free systems of other plants. 6beta,7beta-Dihydroxykaurenoic acid is found in fruits and japanese pumpkin.

   

(ent-16alpha)-16-Kauranol

(1S,4S,9S,10S,14R)-5,5,9,14-tetramethyltetracyclo[11.2.1.01,10.04,9]hexadecan-14-ol

C20H34O (290.2609514)


(ent-16alpha)-16-Kauranol is found in fats and oils. (ent-16alpha)-16-Kauranol is isolated from sunflowers. Isolated from sunflowers. ent-16a-Kauranol is found in fats and oils.

   

ent-17-Hydroxy-15-kauren-19-oic acid

14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid

C20H30O3 (318.21948299999997)


ent-17-Hydroxy-15-kauren-19-oic acid is found in corn. ent-17-Hydroxy-15-kauren-19-oic acid is isolated from Aralia cordata (udo). Isolated from Aralia cordata (udo). ent-17-Hydroxy-15-kauren-19-oic acid is found in green vegetables and corn.

   

ent-17-Hydroxy-16beta-kauran-19-al

14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carbaldehyde

C20H32O2 (304.24021719999996)


ent-17-Hydroxy-16beta-kauran-19-al is found in fruits. ent-17-Hydroxy-16beta-kauran-19-al is isolated from Annona squamosa (sugar apple). Isolated from Annona squamosa (sugar apple). ent-17-Hydroxy-16b-kauran-19-al is found in fruits.

   

Kaurenoic acid methyl ester

Methyl 5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

C21H32O2 (316.24021719999996)


Kaurenoic acid methyl ester is found in fats and oils. Kaurenoic acid methyl ester is isolated from Helianthus annuus (sunflower). Isolated from Helianthus annuus (sunflower). Kaurenoic acid methyl ester is found in fats and oils.

   

Siderol

5-(Hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-yl acetic acid

C22H34O3 (346.25078140000005)


Siderol is a constituent of Sideritis species Constituent of Sideritis subspecies

   

ent-16beta-Methoxy-19-kauranoic acid

14-methoxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

C21H34O3 (334.25078140000005)


ent-16beta-Methoxy-19-kauranoic acid is found in alcoholic beverages. ent-16beta-Methoxy-19-kauranoic acid is a constituent of Annona glabra (pond apple) Constituent of Annona glabra (pond apple). ent-16b-Methoxy-19-kauranoic acid is found in alcoholic beverages and fruits.

   

(ent-15beta,16beta)-15,16-Epoxy-3-kauranone

5,5,9,14-tetramethyl-15-oxapentacyclo[11.3.1.0¹,¹⁰.0⁴,⁹.0¹⁴,¹⁶]heptadecan-6-one

C20H30O2 (302.224568)


(ent-15beta,16beta)-15,16-Epoxy-3-kauranone is found in cereals and cereal products. (ent-15beta,16beta)-15,16-Epoxy-3-kauranone is isolated from leaves of a blight-resistant rice cultivar. Isolated from leaves of a blight-resistant rice cultivariety ent-15b,16b-Epoxy-3-kauranone is found in cereals and cereal products.

   

ent-15-Oxo-16-kauren-19-oic acid

5,9-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

C20H28O3 (316.2038338)


ent-15-Oxo-16-kauren-19-oic acid is found in fruits. ent-15-Oxo-16-kauren-19-oic acid is isolated from Chrysobalanus icaco. Isolated from Chrysobalanus icaco. ent-15-Oxo-16-kauren-19-oic acid is found in fruits.

   

Annoglabasin C

14-(acetyloxy)-14-(methoxycarbonyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

C23H34O6 (406.2355264)


Annoglabasin C is found in alcoholic beverages. Annoglabasin C is a constituent of Annona glabra (pond apple) Constituent of Annona glabra (pond apple). Annoglabasin C is found in alcoholic beverages and fruits.

   

ent-17-Acetoxy-16b-kauran-19-al

{5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetic acid

C22H34O3 (346.25078140000005)


ent-17-Acetoxy-16b-kauran-19-al is found in fruits. ent-17-Acetoxy-16b-kauran-19-al is isolated from Annona squamosa (sugar apple). Isolated from Annona squamosa (sugar apple). ent-17-Acetoxy-16b-kauran-19-al is found in fruits.

   

ent-16-Kauren-19-ol acetate

{5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl}methyl acetic acid

C22H34O2 (330.2558664)


ent-16-Kauren-19-ol acetate is found in fruits. ent-16-Kauren-19-ol acetate is a constituent of Annona squamosa (sugar apple) Constituent of Annona squamosa (sugar apple). ent-16-Kauren-19-ol acetate is found in fruits.

   

(ent-15beta)-15-Hydroxy-19-trachylobanoic acid

16-hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid

C20H30O3 (318.21948299999997)


(ent-15beta)-15-Hydroxy-19-trachylobanoic acid is found in fats and oils. (ent-15beta)-15-Hydroxy-19-trachylobanoic acid occurs in sunflowers.

   

(ent-2alpha,3beta,15beta)-16-Kaurene-2,3,15-triol

5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-6,7,15-triol

C20H32O3 (320.23513219999995)


(ent-2alpha,3beta,15beta)-16-Kaurene-2,3,15-triol is found in cereals and cereal products. (ent-2alpha,3beta,15beta)-16-Kaurene-2,3,15-triol is isolated from leaves of a blight-resistant rice cultivar. Isolated from leaves of a blight-resistant rice cultivariety (ent-2alpha,3beta,15beta)-16-Kaurene-2,3,15-triol is found in cereals and cereal products.

   

Epoxysiderol

5-(Hydroxymethyl)-5,9,14-trimethyl-15-oxapentacyclo[11.3.1.0¹,¹⁰.0⁴,⁹.0¹⁴,¹⁶]heptadecan-2-yl acetic acid

C22H34O4 (362.24569640000004)


Epoxysiderol is isolated from Sideritis species. Isolated from Sideritis subspecies

   

Annoglabasin B

5-[(acetyloxy)methyl]-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carboxylic acid

C22H34O4 (362.24569640000004)


Annoglabasin B is found in alcoholic beverages. Annoglabasin B is a constituent of Annona glabra (pond apple). Constituent of Annona glabra (pond apple). Annoglabasin B is found in alcoholic beverages and fruits.

   

ent-16b,19-Kauranediol 19-acetate

{14-hydroxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl}methyl acetic acid

C22H36O3 (348.26643060000004)


ent-16b,19-Kauranediol 19-acetate is found in fats and oils. ent-16b,19-Kauranediol 19-acetate is isolated from sunflowers. Isolated from sunflowers. ent-16b,19-Kauranediol 19-acetate is found in fats and oils.

   

Annosquamosin B

14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,14-diol

C19H32O3 (308.23513219999995)


Annosquamosin B is found in fruits. Annosquamosin B is a constituent of Annona squamosa (sugar apple) Constituent of Annona squamosa (sugar apple). Annosquamosin B is found in fruits.

   

ent-17-Oxo-15-kauren-19-oic acid

14-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid

C20H28O3 (316.2038338)


ent-17-Oxo-15-kauren-19-oic acid is a constituent of Helianthus species. Constituent of Helianthus subspecies

   

(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid

2,3,12-trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

C20H30O5 (350.209313)


(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid is found in fruits. (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid is a constituent of Cucurbita maxima. Constituent of Cucurbita maxima. 6alpha,7alpha,12alpha-Trihydroxykaurenoic acid is found in fruits and japanese pumpkin.

   

Sideridiol

5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-ol

C20H32O2 (304.24021719999996)


Sideridiol is a constituent of Sideritis species. Constituent of Sideritis subspecies

   

(ent-2alpha,3beta,15beta,16beta)-15,16-Epoxy-2,3-kauranediol

5,5,9,14-tetramethyl-15-oxapentacyclo[11.3.1.0¹,¹⁰.0⁴,⁹.0¹⁴,¹⁶]heptadecane-6,7-diol

C20H32O3 (320.23513219999995)


(ent-2alpha,3beta,15beta,16beta)-15,16-Epoxy-2,3-kauranediol is found in cereals and cereal products. (ent-2alpha,3beta,15beta,16beta)-15,16-Epoxy-2,3-kauranediol is isolated from leaves of a blight-resistant rice cultivar. Isolated from leaves of a blight-resistant rice cultivariety ent-15b,16b-Epoxy-2a,3b-kauranediol is found in cereals and cereal products.

   

Annoglabasin E

5-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carboxylic acid

C20H32O3 (320.23513219999995)


Annoglabasin E is found in alcoholic beverages. Annoglabasin E is a constituent of Annona glabra (pond apple) Constituent of Annona glabra (pond apple). Annoglabasin E is found in alcoholic beverages and fruits.

   

ent-15-Kaurene-17,19-dioic acid

5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5,14-dicarboxylic acid

C20H28O4 (332.19874880000003)


ent-15-Kaurene-17,19-dioic acid is isolated from Helianthus species. Isolated from Helianthus subspecies

   

(ent-15beta)-15,19-Dihydroxy-7-trachylobanone

16-hydroxy-5-(hydroxymethyl)-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecan-2-one

C20H30O3 (318.21948299999997)


(ent-15beta)-15,19-Dihydroxy-7-trachylobanone is found in fats and oils. (ent-15beta)-15,19-Dihydroxy-7-trachylobanone is a constituent of Helianthus annuus (sunflower). Constituent of Helianthus annuus (sunflower). 15beta,19-ent-Dihydroxy-7-trachylobanone is found in fats and oils.

   

Dimethyl ent-16alpha-kaurane-17,19-dioate

5,14-Dimethyl 5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,14-dicarboxylic acid

C22H34O4 (362.24569640000004)


Dimethyl ent-16alpha-kaurane-17,19-dioate is found in alcoholic beverages. Dimethyl ent-16alpha-kaurane-17,19-dioate is a constituent of Annona glabra (pond apple)

   

Annoglabasin A

Methyl 14-(acetyloxy)-5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carboxylic acid

C23H34O5 (390.24061140000003)


Annoglabasin D is found in alcoholic beverages. Annoglabasin D is a constituent of Annona glabra (pond apple) Constituent of Annona glabra (pond apple). Annoglabasin A is found in alcoholic beverages and fruits.

   

Siderone

5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-one

C20H30O2 (302.224568)


Siderone is found in tea. Siderone is isolated from Sideritis syriaca (Greek mountain tea). Isolated from Sideritis syriaca (Greek mountain tea). Siderone is found in tea.

   

Annosquamosin A

[(5R,9S,13S,14S)-5-Formyl-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl]methyl acetic acid

C22H34O4 (362.24569640000004)


Annosquamosin A is found in fruits. Annosquamosin A is a constituent of the seeds of Annona squamosa (sugar apple) Constituent of the seeds of Annona squamosa (sugar apple). Annosquamosin A is found in fruits.

   

Annoglabasin F

Methyl 14-(acetyloxy)-5-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carboxylic acid

C22H34O5 (378.24061140000003)


Annoglabasin F is found in alcoholic beverages. Annoglabasin F is a constituent of Annona glabra (pond apple) Constituent of Annona glabra (pond apple). Annoglabasin F is found in alcoholic beverages and fruits.

   

ent-6,16-Kauradien-19-oic acid

5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-2-ene-5-carboxylic acid

C20H28O2 (300.2089188)


ent-6,16-Kauradien-19-oic acid is found in fruits. ent-6,16-Kauradien-19-oic acid is produced by seed extracts of Cucurbita maxima. Production by seed extracts of Cucurbita maxima. ent-6,16-Kauradien-19-oic acid is found in fruits and japanese pumpkin.

   

Thujyl 19-trachylobanoate

2-Methyl-5-(propan-2-yl)bicyclo[3.1.0]hexan-2-yl 5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid

C30H46O2 (438.34976159999997)


Thujyl 19-trachylobanoate is found in fats and oils. Thujyl 19-trachylobanoate is isolated from sunflowers. Isolated from sunflowers. Thujyl 19-trachylobanoate is found in sunflower and fats and oils.

   

ent-19-Trachylobanal

5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carbaldehyde

C20H30O (286.229653)


ent-19-Trachylobanal is found in fats and oils. ent-19-Trachylobanal is isolated from sunflowers. Isolated from sunflowers. 19-Trachylobanal is found in sunflower and fats and oils.

   

ent-16a-Hydroxy-17-acetoxy-19-kauranal

{5-formyl-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetic acid

C22H34O4 (362.24569640000004)


ent-16a-Hydroxy-17-acetoxy-19-kauranal is found in fruits. ent-16a-Hydroxy-17-acetoxy-19-kauranal is a constituent of Annona squamosa (sugar apple). Constituent of Annona squamosa (sugar apple). ent-16a-Hydroxy-17-acetoxy-19-kauranal is found in fruits.

   

Atractyligenin

(5R,7R,9R,15S)-7-hydroxy-9,15-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

C20H30O3 (318.21948299999997)


Atractyligenin is a diterpene that is found in many coffees and is largely excreted, unchanged, in urine. It is thought to be a good marker for coffee consumption. About 70\\% of the total atractyligenin in roast coffee is extracted during the brewing process. Robusta coffees tend to have only 10\\% of the atractyligenin content of Arabica coffees.

   

(1R,9S,14S,15R,19S)-13,14,19-Trihydroxy-16,16-dimethyl-6-methylidene-10,12-dioxahexacyclo[9.8.0.01,15.02,8.05,9.08,13]nonadecan-7-one

(1R,9S,14S,15R,19S)-13,14,19-Trihydroxy-16,16-dimethyl-6-methylidene-10,12-dioxahexacyclo[9.8.0.01,15.02,8.05,9.08,13]nonadecan-7-one

C20H26O6 (362.17292960000003)


Ponicidin (Rubescensine B) is a diterpenoid derived from Rabdosia rubescens, and exhibits immunoregulatory, anti-inflammatory, anti-viral and anti-cancer activity. Ponicidin (Rubescensine B) induces apoptosis of gastric carcinoma cell, decreases the phosphorylation of JAK2 and STAT3, and shows no effect on protein levels of JAK2 and STAT3[1]. Ponicidin (Rubescensine B) is a diterpenoid derived from Rabdosia rubescens, and exhibits immunoregulatory, anti-inflammatory, anti-viral and anti-cancer activity. Ponicidin (Rubescensine B) induces apoptosis of gastric carcinoma cell, decreases the phosphorylation of JAK2 and STAT3, and shows no effect on protein levels of JAK2 and STAT3[1].

   

(1S,22S,23S,25R,26R,28S,31S,33S)-22-Hydroxy-1,10,10,12,12,30,30,36-octamethyl-28-(2-methylprop-1-enyl)-11,24,27,29,32-pentaoxa-3-azadecacyclo[17.17.0.02,17.04,16.07,15.09,13.022,36.023,25.023,33.026,31]hexatriaconta-2(17),4(16),5,7(15)-tetraen-8-one

(1S,22S,23S,25R,26R,28S,31S,33S)-22-Hydroxy-1,10,10,12,12,30,30,36-octamethyl-28-(2-methylprop-1-enyl)-11,24,27,29,32-pentaoxa-3-azadecacyclo[17.17.0.02,17.04,16.07,15.09,13.022,36.023,25.023,33.026,31]hexatriaconta-2(17),4(16),5,7(15)-tetraen-8-one

C42H55NO7 (685.3978319999999)


   

Oridonin

9,10,15,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one

C20H28O6 (364.1885788)


   

(1R,4R,5S,9R,10S,13R)-5,9-Dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid

(1R,4R,5S,9R,10S,13R)-5,9-Dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid

C20H30O2 (302.224568)


Kaurenoic acid, also known as kaur-16-en-18-oic acid or kaurenoate, is a member of the class of compounds known as kaurane diterpenoids. Kaurane diterpenoids are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Kaurenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Kaurenoic acid can be found in sunflower, which makes kaurenoic acid a potential biomarker for the consumption of this food product. Kaurenoic acid is a diterpene from Sphagneticola trilobata, inhibits Inflammatory Pain by the inhibition of cytokine production and activation of the NO–cyclic GMP–PKG–ATP-sensitive potassium channel signaling pathway[1]. Kaurenoic acid is a diterpene from Sphagneticola trilobata, inhibits Inflammatory Pain by the inhibition of cytokine production and activation of the NO–cyclic GMP–PKG–ATP-sensitive potassium channel signaling pathway[1].

   

ent-kaurane

5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane

C20H34 (274.2660364)


   

Glaucocalyxin A

2,16-dihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-6,15-dione

C20H28O4 (332.19874880000003)


   

Kakkalide

5-hydroxy-6-methoxy-3-(4-methoxyphenyl)-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-4-one

C28H32O15 (608.1741122)


   

(1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene

(1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene

C20H32 (272.2503872)


   

Kaurenoic acid thujanol ester

4-methyl-1-(propan-2-yl)cyclohex-3-en-1-yl (1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

C30H46O2 (438.34976159999997)


Kaurenoic acid thujanol ester is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Kaurenoic acid thujanol ester can be found in sunflower, which makes kaurenoic acid thujanol ester a potential biomarker for the consumption of this food product.

   

ent-16b-Kauran-16,19-diol

(1S,4S,5R,9S,10R,13R,14R)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-ol

C20H34O2 (306.2558664)


Ent-16b-kauran-16,19-diol is a member of the class of compounds known as kaurane diterpenoids. Kaurane diterpenoids are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Ent-16b-kauran-16,19-diol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Ent-16b-kauran-16,19-diol can be found in sunflower, which makes ent-16b-kauran-16,19-diol a potential biomarker for the consumption of this food product.

   

ent-Kauran-16-beta-ol

(1S,4R,9R,10R,13R,14R)-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-ol

C20H34O (290.2609514)


Ent-kauran-16-beta-ol is a member of the class of compounds known as kaurane diterpenoids. Kaurane diterpenoids are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Ent-kauran-16-beta-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Ent-kauran-16-beta-ol can be found in sunflower, which makes ent-kauran-16-beta-ol a potential biomarker for the consumption of this food product.

   

Ciliaric acid

2-Hydroxy-5,9,13-trimethylpentacyclo[11.2.1.01,10.04,9.012,14]hexadecane-5-carboxylic acid

C20H30O3 (318.21948299999997)


Ciliaric acid, also known as ciliarate, is a member of the class of compounds known as kaurane diterpenoids. Kaurane diterpenoids are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Ciliaric acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Ciliaric acid can be found in sunflower, which makes ciliaric acid a potential biomarker for the consumption of this food product.

   

ent-16-Kauren-19-ol

{5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-5-yl}methanol

C20H32O (288.24530219999997)


ent-16-Kauren-19-ol, also known as ent-kaurenol or kaur-16-en-18-ol, belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. ent-16-Kauren-19-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

   

19-Trachylobanoic acid

5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid

C20H30O2 (302.224568)


19-trachylobanoic acid is a member of the class of compounds known as kaurane diterpenoids. Kaurane diterpenoids are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. 19-trachylobanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 19-trachylobanoic acid can be found in sunflower, which makes 19-trachylobanoic acid a potential biomarker for the consumption of this food product.

   

Patuletin 7-glucoside

2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-6-methoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

C22H22O13 (494.1060362)


Patuletin 7-glucoside is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Patuletin 7-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Patuletin 7-glucoside can be found in german camomile, which makes patuletin 7-glucoside a potential biomarker for the consumption of this food product.

   

ent-7alpha-hydroxykaur-16-en-19-oate

2-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

C20H30O3 (318.21948299999997)


Ent-7alpha-hydroxykaur-16-en-19-oate is a member of the class of compounds known as kaurane diterpenoids. Kaurane diterpenoids are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Ent-7alpha-hydroxykaur-16-en-19-oate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Ent-7alpha-hydroxykaur-16-en-19-oate can be found in a number of food items such as greenthread tea, cardamom, agave, and hickory nut, which makes ent-7alpha-hydroxykaur-16-en-19-oate a potential biomarker for the consumption of these food products.

   

ent-kaur-16-en-19-oate

5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

C20H29O2 (301.2167434)


Ent-kaur-16-en-19-oate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Ent-kaur-16-en-19-oate can be found in a number of food items such as tronchuda cabbage, garden rhubarb, quince, and spelt, which makes ent-kaur-16-en-19-oate a potential biomarker for the consumption of these food products.

   

ent-kaurenal

5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carbaldehyde

C20H30O (286.229653)


Ent-16-kauren-19-al is a member of the class of compounds known as kaurane diterpenoids. Kaurane diterpenoids are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Ent-16-kauren-19-al is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Ent-16-kauren-19-al can be found in fruits and sunflower, which makes ent-16-kauren-19-al a potential biomarker for the consumption of these food products.