NCBI Taxonomy: 176551

Loxothysanus sinuatus (ncbi_taxid: 176551)

found 54 associated metabolites at species taxonomy rank level.

Ancestor: Loxothysanus

Child Taxonomies: none taxonomy data.

Helenalin

{Azuleno[6,} 5-b]furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a, 8-dimethyl-3-methylene-, {[3aS-(3a.alpha.,4.alpha.,4a.beta.,} 7a.alpha.,8.alpha.,9a.alpha.)]-

C15H18O4 (262.1205)


Helenalin is a sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer). It has a role as an anti-inflammatory agent, an antineoplastic agent, a plant metabolite and a metabolite. It is a gamma-lactone, a cyclic ketone, an organic heterotricyclic compound, a sesquiterpene lactone and a secondary alcohol. Helenalin is a natural product found in Pentanema britannicum, Psilostrophe cooperi, and other organisms with data available. A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer). D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors D002491 - Central Nervous System Agents > D000700 - Analgesics D020011 - Protective Agents > D002316 - Cardiotonic Agents D000893 - Anti-Inflammatory Agents D000970 - Antineoplastic Agents D002317 - Cardiovascular Agents D018501 - Antirheumatic Agents

   

DivK1c_000746

alpha-Cyclocostunolide

C15H20O2 (232.1463)


   

beta-cyclocostunolide

[3aR-(3aalpha,5aalpha,9abeta,9balpha)]-Decahydro-5a-methyl-3,9-bis(methylene)naphtho[1,2-b]furan-2(3H)-one

C15H20O2 (232.1463)


   

Plenolin

(1S,3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-1,5,8a-trimethyl-3a,4,5,5a,9,9a-hexahydro-1H-azuleno[7,6-d]furan-2,8-quinone

C15H20O4 (264.1362)


   

beta-Caryophyllene

trans-(1R,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene

C15H24 (204.1878)


beta-Caryophyllene, also known as caryophyllene or (−)-β-caryophyllene, is a natural bicyclic sesquiterpene that is a constituent of many essential oils including that of Syzygium aromaticum (cloves), Cannabis sativa, rosemary, and hops. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. beta-Caryophyllene is notable for having both a cyclobutane ring and a trans-double bond in a nine-membered ring, both rarities in nature (Wikipedia). beta-Caryophyllene is a sweet and dry tasting compound that can be found in a number of food items such as allspice, fig, pot marjoram, and roman camomile, which makes beta-caryophyllene a potential biomarker for the consumption of these food products. beta-Caryophyllene can be found in feces and saliva. (-)-Caryophyllene. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=87-44-5 (retrieved 2024-08-07) (CAS RN: 87-44-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). β-Caryophyllene is a CB2 receptor agonist. β-Caryophyllene is a CB2 receptor agonist.

   

Germacrene D

(1E,6E,8S)-1-methyl-8-(1-methylethyl)-5-methylidenecyclodeca-1,6-diene

C15H24 (204.1878)


Germacrene d, also known as germacrene d, (s-(e,e))-isomer, is a member of the class of compounds known as germacrane sesquiterpenoids. Germacrane sesquiterpenoids are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. Germacrene d can be found in a number of food items such as peppermint, roman camomile, hyssop, and common walnut, which makes germacrene d a potential biomarker for the consumption of these food products.

   

(+)-beta-Caryophyllene

(+)-beta-Caryophyllene

C15H24 (204.1878)


A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has R configuration while the remaining stereocentre has S configuration. It is the enantiomer of (-)-beta-caryophyllene, which occurs much more widely than the (+)-form.

   

Helenalin

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

C15H18O4 (262.1205)


   

Germacrene D

1,6-Cyclodecadiene, 1-methyl-5-methylene-8-(1-methylethyl)-, [s-(E,E)]-

C15H24 (204.1878)


(-)-germacrene D is a germacrene D. It is an enantiomer of a (+)-germacrene D. (-)-Germacrene D is a natural product found in Teucrium montanum, Stachys obliqua, and other organisms with data available. See also: Clary Sage Oil (part of).

   
   

caryophyllene

(-)-beta-Caryophyllene

C15H24 (204.1878)


A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents β-Caryophyllene is a CB2 receptor agonist. β-Caryophyllene is a CB2 receptor agonist.

   

8-Epihelenalin

8-Epihelenalin

C15H18O4 (262.1205)


A sesquiterpene lactone that is the C-8 epimer of helenalin. Isolated from the aerial parts of Inula hupehensis, it exhibits anti-inflammatory activity.

   

alpha-Cyclocostunolide

alpha-Cyclocostunolide

C15H20O2 (232.1463)


   

beta-cyclocostunolide

beta-cyclocostunolide

C15H20O2 (232.1463)


   

[(1r,3s,4s,5s,7r)-10-methylidene-9-oxo-4-(3-oxobutyl)-8-oxatricyclo[5.3.0.0³,⁵]decan-5-yl]methyl acetate

[(1r,3s,4s,5s,7r)-10-methylidene-9-oxo-4-(3-oxobutyl)-8-oxatricyclo[5.3.0.0³,⁵]decan-5-yl]methyl acetate

C17H22O5 (306.1467)


   

(3ar,4ar,5r,7s,7as,9ar)-5-hydroxy-5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-7-yl acetate

(3ar,4ar,5r,7s,7as,9ar)-5-hydroxy-5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-7-yl acetate

C17H22O5 (306.1467)


   

β-cyclocostunolide

β-cyclocostunolide

C15H20O2 (232.1463)


   

(3r,3as,4s,4ar,7ar,8r,9as)-4-hydroxy-3,4a,8-trimethyl-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-2,5-dione

(3r,3as,4s,4ar,7ar,8r,9as)-4-hydroxy-3,4a,8-trimethyl-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-2,5-dione

C15H20O4 (264.1362)


   

5a,9-dimethyl-3-methylidene-3ah,4h,5h,6h,7h,9ah,9bh-naphtho[1,2-b]furan-2-one

5a,9-dimethyl-3-methylidene-3ah,4h,5h,6h,7h,9ah,9bh-naphtho[1,2-b]furan-2-one

C15H20O2 (232.1463)


   

[9-hydroxy-4-(3-hydroxybutyl)-10-methylidene-8-oxatricyclo[5.3.0.0³,⁵]decan-5-yl]methyl acetate

[9-hydroxy-4-(3-hydroxybutyl)-10-methylidene-8-oxatricyclo[5.3.0.0³,⁵]decan-5-yl]methyl acetate

C17H26O5 (310.178)


   

(3ar,4as,5r,7s,7as,8r,9as)-5-(acetyloxy)-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate

(3ar,4as,5r,7s,7as,8r,9as)-5-(acetyloxy)-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate

C19H26O6 (350.1729)


   

4,5-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

4,5-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

C20H30O6 (366.2042)


   

(+)-caryophyllene

(+)-caryophyllene

C15H24 (204.1878)


   

4-(3-hydroxybutyl)-5-(hydroxymethyl)-10-methylidene-8-oxatricyclo[5.3.0.0³,⁵]decan-9-ol

4-(3-hydroxybutyl)-5-(hydroxymethyl)-10-methylidene-8-oxatricyclo[5.3.0.0³,⁵]decan-9-ol

C15H24O4 (268.1675)


   

(1r,2r,3s,7s,9r,10s,11r,13s,14r)-2,14-dihydroxy-1,9-dimethyl-4-methylidene-6,12-dioxatetracyclo[8.4.0.0³,⁷.0¹¹,¹³]tetradecan-5-one

(1r,2r,3s,7s,9r,10s,11r,13s,14r)-2,14-dihydroxy-1,9-dimethyl-4-methylidene-6,12-dioxatetracyclo[8.4.0.0³,⁷.0¹¹,¹³]tetradecan-5-one

C15H20O5 (280.1311)


   

(3r,3ar,4s,4ar,7ar,8r,9as)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl (2e)-2-methylbut-2-enoate

(3r,3ar,4s,4ar,7ar,8r,9as)-3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl (2e)-2-methylbut-2-enoate

C20H26O5 (346.178)


   

5-hydroxy-5,8-dimethyl-3-methylidene-2-oxo-3ah,4h,6h,7h,8h,9h,9ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

5-hydroxy-5,8-dimethyl-3-methylidene-2-oxo-3ah,4h,6h,7h,8h,9h,9ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

C20H28O5 (348.1937)


   

(1z,6z,8s)-8-isopropyl-1-methyl-5-methylidenecyclodeca-1,6-diene

(1z,6z,8s)-8-isopropyl-1-methyl-5-methylidenecyclodeca-1,6-diene

C15H24 (204.1878)


   

5-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 2-methylbut-2-enoate

5-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 2-methylbut-2-enoate

C20H28O5 (348.1937)


   

5-(acetyloxy)-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate

5-(acetyloxy)-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate

C19H26O6 (350.1729)


   

2,14-dihydroxy-1,9-dimethyl-4-methylidene-6,12-dioxatetracyclo[8.4.0.0³,⁷.0¹¹,¹³]tetradecan-5-one

2,14-dihydroxy-1,9-dimethyl-4-methylidene-6,12-dioxatetracyclo[8.4.0.0³,⁷.0¹¹,¹³]tetradecan-5-one

C15H20O5 (280.1311)


   

5-(acetyloxy)-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

5-(acetyloxy)-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

C22H32O6 (392.2199)


   

4a,8-dimethyl-3-methylidene-2,5-dioxo-3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylbut-2-enoate

4a,8-dimethyl-3-methylidene-2,5-dioxo-3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylbut-2-enoate

C20H24O5 (344.1624)


   

(3ar,4s,4ar,7ar,8r,9as)-4a,8-dimethyl-3-methylidene-2,5-dioxo-3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl (2e)-2-methylbut-2-enoate

(3ar,4s,4ar,7ar,8r,9as)-4a,8-dimethyl-3-methylidene-2,5-dioxo-3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl (2e)-2-methylbut-2-enoate

C20H24O5 (344.1624)


   

[10-methylidene-9-oxo-4-(3-oxobutyl)-8-oxatricyclo[5.3.0.0³,⁵]decan-5-yl]methyl acetate

[10-methylidene-9-oxo-4-(3-oxobutyl)-8-oxatricyclo[5.3.0.0³,⁵]decan-5-yl]methyl acetate

C17H22O5 (306.1467)


   

5-hydroxy-5,8-dimethyl-3-methylidene-2-oxo-3ah,6h,7h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

5-hydroxy-5,8-dimethyl-3-methylidene-2-oxo-3ah,6h,7h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

C20H28O5 (348.1937)


   

[(1r,3s,4s,5s,7r,9r)-9-hydroxy-4-[(3s)-3-hydroxybutyl]-10-methylidene-8-oxatricyclo[5.3.0.0³,⁵]decan-5-yl]methyl acetate

[(1r,3s,4s,5s,7r,9r)-9-hydroxy-4-[(3s)-3-hydroxybutyl]-10-methylidene-8-oxatricyclo[5.3.0.0³,⁵]decan-5-yl]methyl acetate

C17H26O5 (310.178)


   

(5r,9s,13s)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

(5r,9s,13s)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

C20H30O2 (302.2246)


   

(3as,4r,4as,5r,7s,7as,8r,9as)-4,5-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

(3as,4r,4as,5r,7s,7as,8r,9as)-4,5-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

C20H30O6 (366.2042)


   

4,5-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate

4,5-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate

C17H24O6 (324.1573)


   

(1s,2r,3r,7s,9r,10s,11r,13s,14r)-14-hydroxy-1,9-dimethyl-4-methylidene-5-oxo-6,12-dioxatetracyclo[8.4.0.0³,⁷.0¹¹,¹³]tetradecan-2-yl acetate

(1s,2r,3r,7s,9r,10s,11r,13s,14r)-14-hydroxy-1,9-dimethyl-4-methylidene-5-oxo-6,12-dioxatetracyclo[8.4.0.0³,⁷.0¹¹,¹³]tetradecan-2-yl acetate

C17H22O6 (322.1416)


   

(3as,4r,4as,5r,7s,7as,8r,9as)-4,5-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate

(3as,4r,4as,5r,7s,7as,8r,9as)-4,5-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate

C17H24O6 (324.1573)


   

5-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

5-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

C20H30O5 (350.2093)


   

14-hydroxy-1,9-dimethyl-4-methylidene-5-oxo-6,12-dioxatetracyclo[8.4.0.0³,⁷.0¹¹,¹³]tetradecan-2-yl acetate

14-hydroxy-1,9-dimethyl-4-methylidene-5-oxo-6,12-dioxatetracyclo[8.4.0.0³,⁷.0¹¹,¹³]tetradecan-2-yl acetate

C17H22O6 (322.1416)


   

(3ar,4as,5r,7s,7as,8r,9as)-5-(acetyloxy)-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

(3ar,4as,5r,7s,7as,8r,9as)-5-(acetyloxy)-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

C22H32O6 (392.2199)


   

(3ar,5r,7s,7as,8r,9as)-5-hydroxy-5,8-dimethyl-3-methylidene-2-oxo-3ah,6h,7h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

(3ar,5r,7s,7as,8r,9as)-5-hydroxy-5,8-dimethyl-3-methylidene-2-oxo-3ah,6h,7h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

C20H28O5 (348.1937)


   

(3ar,5r,7s,8r,9as)-5-hydroxy-5,8-dimethyl-3-methylidene-2-oxo-3ah,4h,6h,7h,8h,9h,9ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

(3ar,5r,7s,8r,9as)-5-hydroxy-5,8-dimethyl-3-methylidene-2-oxo-3ah,4h,6h,7h,8h,9h,9ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

C20H28O5 (348.1937)


   

(1r,3s,4s,5s,7r,9s)-4-[(3s)-3-hydroxybutyl]-5-(hydroxymethyl)-10-methylidene-8-oxatricyclo[5.3.0.0³,⁵]decan-9-ol

(1r,3s,4s,5s,7r,9s)-4-[(3s)-3-hydroxybutyl]-5-(hydroxymethyl)-10-methylidene-8-oxatricyclo[5.3.0.0³,⁵]decan-9-ol

C15H24O4 (268.1675)


   

5-hydroxy-5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-7-yl acetate

5-hydroxy-5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-7-yl acetate

C17H22O5 (306.1467)


   

8-isopropyl-1-methyl-5-methylidenecyclodeca-1,6-diene

8-isopropyl-1-methyl-5-methylidenecyclodeca-1,6-diene

C15H24 (204.1878)


   

(3ar,4as,5r,7s,7as,8r,9as)-5-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

(3ar,4as,5r,7s,7as,8r,9as)-5-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate

C20H30O5 (350.2093)


   

α-cyclocostunolide

α-cyclocostunolide

C15H20O2 (232.1463)


   

3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylbut-2-enoate

3,4a,8-trimethyl-2,5-dioxo-3h,3ah,4h,7ah,8h,9h,9ah-azuleno[6,5-b]furan-4-yl 2-methylbut-2-enoate

C20H26O5 (346.178)


   

(3ar,4as,5r,7s,7as,8r,9as)-5-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl (2e)-2-methylbut-2-enoate

(3ar,4as,5r,7s,7as,8r,9as)-5-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl (2e)-2-methylbut-2-enoate

C20H28O5 (348.1937)