NCBI Taxonomy: 53584

Lindheimera (ncbi_taxid: 53584)

found 91 associated metabolites at genus taxonomy rank level.

Ancestor: Heliantheae

Child Taxonomies: Lindheimera texana

Oleanolic acid

(4aS,5S,6aS,6bR,8R,8aR,10S,12aR,12bR,14bS)-10-Hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid

C30H48O3 (456.36032579999994)


Oleanolic acid is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Oleanolic acid exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. Oleanolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. (PMID:17292619, 15522132, 15994040). Oleanolic acid is a pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It is a conjugate acid of an oleanolate. It derives from a hydride of an oleanane. Oleanolic acid is a natural product found in Ophiopogon japonicus, Freziera, and other organisms with data available. A pentacyclic triterpene that occurs widely in many PLANTS as the free acid or the aglycone for many SAPONINS. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin. See also: Holy basil leaf (part of); Jujube fruit (part of); Paeonia lactiflora root (part of) ... View More ... Occurs as glycosides in cloves (Syzygium aromaticum), sugar beet (Beta vulgaris), olive leaves, etc. Very widely distributed aglycone A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. [Raw Data] CBA90_Oleanolic-acid_neg_50eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_20eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_10eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_30eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_40eV.txt Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.

   

Sclareolide

Naphtho(2,1-b)furan-2(1H)-one, 3a,4,5,5aalpha,6,7,8,9,9a,9balpha-decahydro-3abeta,6,6,9abeta-tetramethyl-

C16H26O2 (250.1932696)


Norambreinolide is a naphthofuran. Sclareolide is a natural product found in Cistus creticus, Arnica angustifolia, and other organisms with data available. Sclareolide is isolated from the flower of Perilla frutescens with antibacterial and cytotoxic activities[1]. Sclareolide is isolated from the flower of Perilla frutescens with antibacterial and cytotoxic activities[1].

   
   

sclareolide

(3aR)-(+)-Sclareolide

C16H26O2 (250.1932696)


relative retention time with respect to 9-anthracene Carboxylic Acid is 1.365 Sclareolide is isolated from the flower of Perilla frutescens with antibacterial and cytotoxic activities[1]. Sclareolide is isolated from the flower of Perilla frutescens with antibacterial and cytotoxic activities[1].

   

Caryophyllin

(4aS,5S,6aS,6bR,8R,8aR,10S,12aR,12bR,14bS)-10-Hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid

C30H48O3 (456.36032579999994)


Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.

   

(1s,3r,8r,11s,12s,14s,15r,16r)-14-hydroxy-7,7,12,16-tetramethyl-15-[(2r,4s,5s)-4,5,6-trihydroxy-6-methylheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one

(1s,3r,8r,11s,12s,14s,15r,16r)-14-hydroxy-7,7,12,16-tetramethyl-15-[(2r,4s,5s)-4,5,6-trihydroxy-6-methylheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one

C30H50O5 (490.365805)


   

(1's,2r,4'r,5'r,6'r,10's,12's,13's,16'r,21'r)-4,4,4',6',12',17',17'-heptamethyl-9'-oxaspiro[1,5-dioxolane-2,8'-hexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan]-18'-one

(1's,2r,4'r,5'r,6'r,10's,12's,13's,16'r,21'r)-4,4,4',6',12',17',17'-heptamethyl-9'-oxaspiro[1,5-dioxolane-2,8'-hexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan]-18'-one

C30H46O4 (470.3395916)


   

2-{3a,6,6,9a-tetramethyl-octahydronaphtho[2,1-b]furan-2-ylidene}butane-1,4-diol

2-{3a,6,6,9a-tetramethyl-octahydronaphtho[2,1-b]furan-2-ylidene}butane-1,4-diol

C20H34O3 (322.25078140000005)


   

14-hydroxy-7,7,12,16-tetramethyl-15-(4,5,6-trihydroxy-6-methylheptan-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one

14-hydroxy-7,7,12,16-tetramethyl-15-(4,5,6-trihydroxy-6-methylheptan-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one

C30H50O5 (490.365805)


   

4,6,12,17,17-pentamethyl-8-(2-methylprop-1-en-1-yl)-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-18-ol

4,6,12,17,17-pentamethyl-8-(2-methylprop-1-en-1-yl)-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-18-ol

C30H48O2 (440.36541079999995)


   

(2z)-2-[(2s,3ar,5as,9as,9br)-3a,6,6,9a-tetramethyl-octahydro-1h-naphtho[2,1-b]furan-2-yl]but-2-ene-1,4-diol

(2z)-2-[(2s,3ar,5as,9as,9br)-3a,6,6,9a-tetramethyl-octahydro-1h-naphtho[2,1-b]furan-2-yl]but-2-ene-1,4-diol

C20H34O3 (322.25078140000005)


   

4,6,12,17,17-pentamethyl-8-(2-methylprop-1-en-1-yl)-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-18-one

4,6,12,17,17-pentamethyl-8-(2-methylprop-1-en-1-yl)-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-18-one

C30H46O2 (438.34976159999997)


   

2-{3a,6,6,9a-tetramethyl-octahydro-1h-naphtho[2,1-b]furan-2-yl}-4-hydroxybut-2-en-1-yl acetate

2-{3a,6,6,9a-tetramethyl-octahydro-1h-naphtho[2,1-b]furan-2-yl}-4-hydroxybut-2-en-1-yl acetate

C22H36O4 (364.2613456)


   

(1s,4r,5r,6r,8s,10s,12s,13s,16r,21r)-4,6,12,17,17-pentamethyl-8-(2-methylprop-1-en-1-yl)-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-18-one

(1s,4r,5r,6r,8s,10s,12s,13s,16r,21r)-4,6,12,17,17-pentamethyl-8-(2-methylprop-1-en-1-yl)-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-18-one

C30H46O2 (438.34976159999997)


   

(1s,3r,8r,11s,12s,14s,15r,16r)-14-hydroxy-15-[(2r)-1-[(2s,3s)-3-isopropyloxiran-2-yl]propan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one

(1s,3r,8r,11s,12s,14s,15r,16r)-14-hydroxy-15-[(2r)-1-[(2s,3s)-3-isopropyloxiran-2-yl]propan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one

C30H48O3 (456.36032579999994)


   

(3ar,9as,9br)-3a,6,6,9a-tetramethyl-octahydronaphtho[2,1-b]furan-2-one

(3ar,9as,9br)-3a,6,6,9a-tetramethyl-octahydronaphtho[2,1-b]furan-2-one

C16H26O2 (250.1932696)


   

(3e)-4-[(1r,2r,4as,8as)-2-hydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl]but-3-en-2-one

(3e)-4-[(1r,2r,4as,8as)-2-hydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl]but-3-en-2-one

C18H30O2 (278.224568)


   

(1s,4r,5r,6s,9s,11s,12s,15r,20r)-4,6,11,16,16-pentamethyl-8-oxahexacyclo[10.9.0.0¹,²⁰.0⁴,¹¹.0⁵,⁹.0¹⁵,²⁰]henicosane-7,17-dione

(1s,4r,5r,6s,9s,11s,12s,15r,20r)-4,6,11,16,16-pentamethyl-8-oxahexacyclo[10.9.0.0¹,²⁰.0⁴,¹¹.0⁵,⁹.0¹⁵,²⁰]henicosane-7,17-dione

C25H36O3 (384.26643060000004)


   

(1s,4r,5r,6r,8r,10s,12s,13s,16r,18s,21r)-4,6,12,17,17-pentamethyl-8-(2-methylprop-1-en-1-yl)-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-18-ol

(1s,4r,5r,6r,8r,10s,12s,13s,16r,18s,21r)-4,6,12,17,17-pentamethyl-8-(2-methylprop-1-en-1-yl)-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-18-ol

C30H48O2 (440.36541079999995)


   

(2z)-2-[(2s,3ar,5as,9as,9br)-3a,6,6,9a-tetramethyl-octahydro-1h-naphtho[2,1-b]furan-2-yl]-4-hydroxybut-2-en-1-yl acetate

(2z)-2-[(2s,3ar,5as,9as,9br)-3a,6,6,9a-tetramethyl-octahydro-1h-naphtho[2,1-b]furan-2-yl]-4-hydroxybut-2-en-1-yl acetate

C22H36O4 (364.2613456)


   

2-{3a,6,6,9a-tetramethyl-octahydro-1h-naphtho[2,1-b]furan-2-yl}but-2-ene-1,4-diol

2-{3a,6,6,9a-tetramethyl-octahydro-1h-naphtho[2,1-b]furan-2-yl}but-2-ene-1,4-diol

C20H34O3 (322.25078140000005)


   

4,6,11,16,16-pentamethyl-8-oxahexacyclo[10.9.0.0¹,²⁰.0⁴,¹¹.0⁵,⁹.0¹⁵,²⁰]henicosane-7,17-dione

4,6,11,16,16-pentamethyl-8-oxahexacyclo[10.9.0.0¹,²⁰.0⁴,¹¹.0⁵,⁹.0¹⁵,²⁰]henicosane-7,17-dione

C25H36O3 (384.26643060000004)


   

14-hydroxy-15-[1-(3-isopropyloxiran-2-yl)propan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one

14-hydroxy-15-[1-(3-isopropyloxiran-2-yl)propan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one

C30H48O3 (456.36032579999994)


   

4,4,4',6',12',17',17'-heptamethyl-9'-oxaspiro[1,5-dioxolane-2,8'-hexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan]-18'-one

4,4,4',6',12',17',17'-heptamethyl-9'-oxaspiro[1,5-dioxolane-2,8'-hexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan]-18'-one

C30H46O4 (470.3395916)


   

4-(2-hydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)but-3-en-2-one

4-(2-hydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)but-3-en-2-one

C18H30O2 (278.224568)


   

(1s,4r,5r,6r,8s,10s,12s,13s,16r,18s,21r)-4,6,12,17,17-pentamethyl-8-(2-methylprop-1-en-1-yl)-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-18-ol

(1s,4r,5r,6r,8s,10s,12s,13s,16r,18s,21r)-4,6,12,17,17-pentamethyl-8-(2-methylprop-1-en-1-yl)-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-18-ol

C30H48O2 (440.36541079999995)