NCBI Taxonomy: 2528738

Baccharis tola (ncbi_taxid: 2528738)

found 58 associated metabolites at species taxonomy rank level.

Ancestor: Baccharis sect. Caespitosae

Child Taxonomies: none taxonomy data.

Scopoletin

7-hydroxy-6-methoxy-2H-chromen-2-one

C10H8O4 (192.0423)


Scopoletin is a hydroxycoumarin that is umbelliferone bearing a methoxy substituent at position 6. It has a role as a plant growth regulator and a plant metabolite. It is functionally related to an umbelliferone. Scopoletin is a natural product found in Ficus auriculata, Haplophyllum cappadocicum, and other organisms with data available. Scopoletin is a coumarin compound found in several plants including those in the genus Scopolia and the genus Brunfelsia, as well as chicory (Cichorium), redstem wormwood (Artemisia scoparia), stinging nettle (Urtica dioica), passion flower (Passiflora), noni (Morinda citrifolia fruit) and European black nightshade (Solanum nigrum) that is comprised of umbelliferone with a methoxy group substituent at position 6. Scopoletin is used to standardize and establish pharmacokinetic properties for products derived from the plants that produce it, such as noni extract. Although the mechanism(s) of action have not yet been established, this agent has potential antineoplastic, antidopaminergic, antioxidant, anti-inflammatory and anticholinesterase effects. Plant growth factor derived from the root of Scopolia carniolica or Scopolia japonica. See also: Arnica montana Flower (part of); Lycium barbarum fruit (part of); Viburnum opulus root (part of). Isolated from Angelica acutiloba (Dong Dang Gui). Scopoletin is found in many foods, some of which are lambsquarters, lemon, sunflower, and sherry. Scopoletin is found in anise. Scopoletin is isolated from Angelica acutiloba (Dong Dang Gui A hydroxycoumarin that is umbelliferone bearing a methoxy substituent at position 6. Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CBA72_Scopoletin_pos_20eV.txt [Raw Data] CBA72_Scopoletin_pos_40eV.txt [Raw Data] CBA72_Scopoletin_neg_30eV.txt [Raw Data] CBA72_Scopoletin_neg_50eV.txt [Raw Data] CBA72_Scopoletin_pos_50eV.txt [Raw Data] CBA72_Scopoletin_pos_10eV.txt [Raw Data] CBA72_Scopoletin_neg_40eV.txt [Raw Data] CBA72_Scopoletin_neg_10eV.txt [Raw Data] CBA72_Scopoletin_pos_30eV.txt [Raw Data] CBA72_Scopoletin_neg_20eV.txt Scopoletin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=92-61-5 (retrieved 2024-07-12) (CAS RN: 92-61-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Scopoletin is an inhibitor of acetylcholinesterase (AChE). Scopoletin is an inhibitor of acetylcholinesterase (AChE).

   

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 (456.3603)


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.

   

Beta-Amyrin

(3S,4aR,5R,6aR,6bR,8S,8aR,12aR,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-Octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-eicosahydro-picen-3-ol

C30H50O (426.3861)


Beta-amyrin is a pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants. It has a role as a plant metabolite and an Aspergillus metabolite. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of an oleanane. beta-Amyrin is a natural product found in Ficus pertusa, Ficus septica, and other organisms with data available. See also: Calendula Officinalis Flower (part of); Viburnum opulus bark (part of); Centaurium erythraea whole (part of). A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1]. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1].

   

Acetovanillone

1-(4-hydroxy-3-methoxyphenyl)ethan-1-one

C9H10O3 (166.063)


Acetovanillone, also known as 4-hydroxy-3-methoxyacetophenone or acetoguaiacon, is a member of the class of compounds known as alkyl-phenylketones. Alkyl-phenylketones are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Acetovanillone is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Acetovanillone is a faint, sweet, and vanillin tasting compound found in corn and garden onion, which makes acetovanillone a potential biomarker for the consumption of these food products. Acetovanillone may be a unique S.cerevisiae (yeast) metabolite. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D020011 - Protective Agents > D000975 - Antioxidants D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents D004791 - Enzyme Inhibitors Apocynin is a selective NADPH-oxidase inhibitor with an IC50 of 10 μM[1][2]. Apocynin improves acute lung inflammation in Carrageenan (HY-125474)-induced pleurisy mice model[3]. Apocynin can also be used for cancer research[4]. Apocynin reverses the aging process in mesenchymal stem cells to promote osteogenesis and increases bone mass[5]. Apocynin is a selective NADPH-oxidase inhibitor with an IC50 of 10 μM[1][2]. Apocynin improves acute lung inflammation in Carrageenan (HY-125474)-induced pleurisy mice model[3]. Apocynin can also be used for cancer research[4]. Apocynin reverses the aging process in mesenchymal stem cells to promote osteogenesis and increases bone mass[5]. Apocynin is a selective NADPH-oxidase inhibitor with an IC50 of 10 μM[1][2]. Apocynin improves acute lung inflammation in Carrageenan (HY-125474)-induced pleurisy mice model[3]. Apocynin can also be used for cancer research[4]. Apocynin reverses the aging process in mesenchymal stem cells to promote osteogenesis and increases bone mass[5].

   

Apigenin 7,4'-dimethyl ether

5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one

C17H14O5 (298.0841)


Apigenin 7,4-dimethyl ether, also known as apigenin dimethylether or 4,7-dimethylapigenin, belongs to the class of organic compounds known as 7-O-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, apigenin 7,4-dimethyl ether is considered to be a flavonoid lipid molecule. Apigenin 7,4-dimethyl ether is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, apigenin 7,4-dimethyl ether has been detected, but not quantified in, common sages and sweet basils. This could make apigenin 7,4-dimethyl ether a potential biomarker for the consumption of these foods. BioTransformer predicts that apigenin 7,4-dimethyl ether is a product of 4,5,7-trimethoxyflavone metabolism via an O-dealkylation reaction and catalyzed by CYP2C9 and CYP2C19 enzymes (PMID: 30612223). 4-methylgenkwanin, also known as apigenin dimethylether or 4,7-dimethylapigenin, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, 4-methylgenkwanin is considered to be a flavonoid lipid molecule. 4-methylgenkwanin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 4-methylgenkwanin can be found in common sage and sweet basil, which makes 4-methylgenkwanin a potential biomarker for the consumption of these food products. The compound 7,4'-Di-O-methylapigenin may be partly responsible for the reported antifungal activity of C. zeyheri, and may serve as a potential source of lead compounds that can be developed as antifungal phytomedicines.And it also showed inhibition of the drug efflux pumps (with IC50 = 51.64 μg/ml). IC50:51.64 μg/ml(Candida albicans drug efflux pumps)[2] In vitro: The isolated 7,4'-Di-O-methylapigenin was further investigated for its inhibitory activity on ABC drug efflux pumps in C. albicans by monitoring an increase in ciprofloxacin, assessing the level of its accumulation, in response to reserpine. There was a higher accumulation of ciprofloxacin in Candida cells in the presence of 7,4'-Di-O-methylapigenin than with reserpine. The compound 7,4'-Di-O-methylapigenine demonstrated the activity in a dose-dependent manner with IC50 value of 51.64 μg/ml. These results support those obtained from synergism assays where by the underlying synergistic antifungal mechanisms could be due to blockage of ABC efflux pumps and increasing the susceptibility of Candida to miconazole.[2] In vivo: In searching for natural products as potential anti-inflammatory agents, 7,4'-Di-O-methylapigenin wasn't evaluated in vivo for its ability to inhibit acute inflammation.[1] The compound 7,4'-Di-O-methylapigenin may be partly responsible for the reported antifungal activity of C. zeyheri, and may serve as a potential source of lead compounds that can be developed as antifungal phytomedicines.And it also showed inhibition of the drug efflux pumps (with IC50 = 51.64 μg/ml). IC50:51.64 μg/ml(Candida albicans drug efflux pumps)[2] In vitro: The isolated 7,4'-Di-O-methylapigenin was further investigated for its inhibitory activity on ABC drug efflux pumps in C. albicans by monitoring an increase in ciprofloxacin, assessing the level of its accumulation, in response to reserpine. There was a higher accumulation of ciprofloxacin in Candida cells in the presence of 7,4'-Di-O-methylapigenin than with reserpine. The compound 7,4'-Di-O-methylapigenine demonstrated the activity in a dose-dependent manner with IC50 value of 51.64 μg/ml. These results support those obtained from synergism assays where by the underlying synergistic antifungal mechanisms could be due to blockage of ABC efflux pumps and increasing the susceptibility of Candida to miconazole.[2] In vivo: In searching for natural products as potential anti-inflammatory agents, 7,4'-Di-O-methylapigenin wasn't evaluated in vivo for its ability to inhibit acute inflammation.[1]

   

Apocynin

InChI=1/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H

C9H10O3 (166.063)


Apocynin is an aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3. It has a role as a non-narcotic analgesic, a non-steroidal anti-inflammatory drug, an antirheumatic drug, a peripheral nervous system drug, an EC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor and a plant metabolite. It is a member of acetophenones, a methyl ketone and an aromatic ketone. Acetovanillone has been used in trials studying the treatment of Bronchial Asthma and Chronic Obstructive Pulmonary Disease. Acetovanillone is a natural product found in Iris tectorum, Apocynum cannabinum, and other organisms with data available. Acetovanillone is a metabolite found in or produced by Saccharomyces cerevisiae. An aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D020011 - Protective Agents > D000975 - Antioxidants D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents D004791 - Enzyme Inhibitors Apocynin is a selective NADPH-oxidase inhibitor with an IC50 of 10 μM[1][2]. Apocynin improves acute lung inflammation in Carrageenan (HY-125474)-induced pleurisy mice model[3]. Apocynin can also be used for cancer research[4]. Apocynin reverses the aging process in mesenchymal stem cells to promote osteogenesis and increases bone mass[5]. Apocynin is a selective NADPH-oxidase inhibitor with an IC50 of 10 μM[1][2]. Apocynin improves acute lung inflammation in Carrageenan (HY-125474)-induced pleurisy mice model[3]. Apocynin can also be used for cancer research[4]. Apocynin reverses the aging process in mesenchymal stem cells to promote osteogenesis and increases bone mass[5]. Apocynin is a selective NADPH-oxidase inhibitor with an IC50 of 10 μM[1][2]. Apocynin improves acute lung inflammation in Carrageenan (HY-125474)-induced pleurisy mice model[3]. Apocynin can also be used for cancer research[4]. Apocynin reverses the aging process in mesenchymal stem cells to promote osteogenesis and increases bone mass[5].

   

Spathulenol

1H-Cycloprop(e)azulen-7-ol, decahydro-1,1,7-trimethyl-4-methylene-, (1aR-(1aalpha,4aalpha,7beta,7abeta,7balpha))-

C15H24O (220.1827)


Spathulenol is a tricyclic sesquiterpenoid that is 4-methylidenedecahydro-1H-cyclopropa[e]azulene carrying three methyl substituents at positions 1, 1 and 7 as well as a hydroxy substituent at position 7. It has a role as a volatile oil component, a plant metabolite, an anaesthetic and a vasodilator agent. It is a sesquiterpenoid, a carbotricyclic compound, a tertiary alcohol and an olefinic compound. Spathulenol is a natural product found in Xylopia aromatica, Xylopia emarginata, and other organisms with data available. See also: Chamomile (part of). A tricyclic sesquiterpenoid that is 4-methylidenedecahydro-1H-cyclopropa[e]azulene carrying three methyl substituents at positions 1, 1 and 7 as well as a hydroxy substituent at position 7. Spathulenol is found in alcoholic beverages. Spathulenol is a constituent of Salvia sclarea (clary sage).

   

Apigenin 7,4'-dimethyl ether

4H-1-Benzopyran-4-one, 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-

C17H14O5 (298.0841)


Apigenin 7,4-dimethyl ether, also known as apigenin dimethylether or 4,7-dimethylapigenin, belongs to the class of organic compounds known as 7-O-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, apigenin 7,4-dimethyl ether is considered to be a flavonoid lipid molecule. Apigenin 7,4-dimethyl ether is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, apigenin 7,4-dimethyl ether has been detected, but not quantified in, common sages and sweet basils. This could make apigenin 7,4-dimethyl ether a potential biomarker for the consumption of these foods. BioTransformer predicts that apigenin 7,4-dimethyl ether is a product of 4,5,7-trimethoxyflavone metabolism via an O-dealkylation reaction and catalyzed by CYP2C9 and CYP2C19 enzymes (PMID: 30612223). 4-methylgenkwanin, also known as apigenin dimethylether or 4,7-dimethylapigenin, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, 4-methylgenkwanin is considered to be a flavonoid lipid molecule. 4-methylgenkwanin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 4-methylgenkwanin can be found in common sage and sweet basil, which makes 4-methylgenkwanin a potential biomarker for the consumption of these food products. Apigenin 7,4-dimethyl ether is a dimethoxyflavone that is the 7,4-dimethyl ether derivative of apigenin. It has a role as a plant metabolite. It is a dimethoxyflavone and a monohydroxyflavone. It is functionally related to an apigenin. Apigenin 7,4-dimethyl ether is a natural product found in Teucrium polium, Calea jamaicensis, and other organisms with data available. A dimethoxyflavone that is the 7,4-dimethyl ether derivative of apigenin. The compound 7,4'-Di-O-methylapigenin may be partly responsible for the reported antifungal activity of C. zeyheri, and may serve as a potential source of lead compounds that can be developed as antifungal phytomedicines.And it also showed inhibition of the drug efflux pumps (with IC50 = 51.64 μg/ml). IC50:51.64 μg/ml(Candida albicans drug efflux pumps)[2] In vitro: The isolated 7,4'-Di-O-methylapigenin was further investigated for its inhibitory activity on ABC drug efflux pumps in C. albicans by monitoring an increase in ciprofloxacin, assessing the level of its accumulation, in response to reserpine. There was a higher accumulation of ciprofloxacin in Candida cells in the presence of 7,4'-Di-O-methylapigenin than with reserpine. The compound 7,4'-Di-O-methylapigenine demonstrated the activity in a dose-dependent manner with IC50 value of 51.64 μg/ml. These results support those obtained from synergism assays where by the underlying synergistic antifungal mechanisms could be due to blockage of ABC efflux pumps and increasing the susceptibility of Candida to miconazole.[2] In vivo: In searching for natural products as potential anti-inflammatory agents, 7,4'-Di-O-methylapigenin wasn't evaluated in vivo for its ability to inhibit acute inflammation.[1] The compound 7,4'-Di-O-methylapigenin may be partly responsible for the reported antifungal activity of C. zeyheri, and may serve as a potential source of lead compounds that can be developed as antifungal phytomedicines.And it also showed inhibition of the drug efflux pumps (with IC50 = 51.64 μg/ml). IC50:51.64 μg/ml(Candida albicans drug efflux pumps)[2] In vitro: The isolated 7,4'-Di-O-methylapigenin was further investigated for its inhibitory activity on ABC drug efflux pumps in C. albicans by monitoring an increase in ciprofloxacin, assessing the level of its accumulation, in response to reserpine. There was a higher accumulation of ciprofloxacin in Candida cells in the presence of 7,4'-Di-O-methylapigenin than with reserpine. The compound 7,4'-Di-O-methylapigenine demonstrated the activity in a dose-dependent manner with IC50 value of 51.64 μg/ml. These results support those obtained from synergism assays where by the underlying synergistic antifungal mechanisms could be due to blockage of ABC efflux pumps and increasing the susceptibility of Candida to miconazole.[2] In vivo: In searching for natural products as potential anti-inflammatory agents, 7,4'-Di-O-methylapigenin wasn't evaluated in vivo for its ability to inhibit acute inflammation.[1]

   

3-Methoxycalycopterin

5-Hydroxy-2- (4-hydroxy-3-methoxyphenyl) -3,6,7,8-tetramethoxy-4H-1-benzopyran-4-one

C20H20O9 (404.1107)


   

5,4-Dihydroxy-3,6,7,8,3-pentamethoxyflavone

5,4-Dihydroxy-3,6,7,8,3-pentamethoxyflavone

C20H20O9 (404.1107)


   

8-Methoxycirsilineol

8-Methoxycirsilineol

C19H18O8 (374.1002)


   

Oleanolic Acid

Oleanolic Acid

C30H48O3 (456.3603)


   

Scopoletin

7-hydroxy-6-methoxychromen-2-one

C10H8O4 (192.0423)


relative retention time with respect to 9-anthracene Carboxylic Acid is 0.636 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.637 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.629 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.631 IPB_RECORD: 1582; CONFIDENCE confident structure Scopoletin is an inhibitor of acetylcholinesterase (AChE). Scopoletin is an inhibitor of acetylcholinesterase (AChE).

   

Spatulenol

1,7,7-trimethyl-4-methylidene-decahydro-1H-cyclopropa[e]azulen-1-ol

C15H24O (220.1827)


   

apocynin

InChI=1\C9H10O3\c1-6(10)7-3-4-8(11)9(5-7)12-2\h3-5,11H,1-2H

C9H10O3 (166.063)


D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D020011 - Protective Agents > D000975 - Antioxidants D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents D004791 - Enzyme Inhibitors Apocynin is a selective NADPH-oxidase inhibitor with an IC50 of 10 μM[1][2]. Apocynin improves acute lung inflammation in Carrageenan (HY-125474)-induced pleurisy mice model[3]. Apocynin can also be used for cancer research[4]. Apocynin reverses the aging process in mesenchymal stem cells to promote osteogenesis and increases bone mass[5]. Apocynin is a selective NADPH-oxidase inhibitor with an IC50 of 10 μM[1][2]. Apocynin improves acute lung inflammation in Carrageenan (HY-125474)-induced pleurisy mice model[3]. Apocynin can also be used for cancer research[4]. Apocynin reverses the aging process in mesenchymal stem cells to promote osteogenesis and increases bone mass[5]. Apocynin is a selective NADPH-oxidase inhibitor with an IC50 of 10 μM[1][2]. Apocynin improves acute lung inflammation in Carrageenan (HY-125474)-induced pleurisy mice model[3]. Apocynin can also be used for cancer research[4]. Apocynin reverses the aging process in mesenchymal stem cells to promote osteogenesis and increases bone mass[5].

   

Scopoletol

2H-1-Benzopyran-2-one, 7-hydroxy-6-methoxy- (9CI)

C10H8O4 (192.0423)


Scopoletin is an inhibitor of acetylcholinesterase (AChE). Scopoletin is an inhibitor of acetylcholinesterase (AChE).

   

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 (456.3603)


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.

   

AIDS-071717

4H-1-Benzopyran-4-one, 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)- (9CI)

C17H14O5 (298.0841)


The compound 7,4'-Di-O-methylapigenin may be partly responsible for the reported antifungal activity of C. zeyheri, and may serve as a potential source of lead compounds that can be developed as antifungal phytomedicines.And it also showed inhibition of the drug efflux pumps (with IC50 = 51.64 μg/ml). IC50:51.64 μg/ml(Candida albicans drug efflux pumps)[2] In vitro: The isolated 7,4'-Di-O-methylapigenin was further investigated for its inhibitory activity on ABC drug efflux pumps in C. albicans by monitoring an increase in ciprofloxacin, assessing the level of its accumulation, in response to reserpine. There was a higher accumulation of ciprofloxacin in Candida cells in the presence of 7,4'-Di-O-methylapigenin than with reserpine. The compound 7,4'-Di-O-methylapigenine demonstrated the activity in a dose-dependent manner with IC50 value of 51.64 μg/ml. These results support those obtained from synergism assays where by the underlying synergistic antifungal mechanisms could be due to blockage of ABC efflux pumps and increasing the susceptibility of Candida to miconazole.[2] In vivo: In searching for natural products as potential anti-inflammatory agents, 7,4'-Di-O-methylapigenin wasn't evaluated in vivo for its ability to inhibit acute inflammation.[1] The compound 7,4'-Di-O-methylapigenin may be partly responsible for the reported antifungal activity of C. zeyheri, and may serve as a potential source of lead compounds that can be developed as antifungal phytomedicines.And it also showed inhibition of the drug efflux pumps (with IC50 = 51.64 μg/ml). IC50:51.64 μg/ml(Candida albicans drug efflux pumps)[2] In vitro: The isolated 7,4'-Di-O-methylapigenin was further investigated for its inhibitory activity on ABC drug efflux pumps in C. albicans by monitoring an increase in ciprofloxacin, assessing the level of its accumulation, in response to reserpine. There was a higher accumulation of ciprofloxacin in Candida cells in the presence of 7,4'-Di-O-methylapigenin than with reserpine. The compound 7,4'-Di-O-methylapigenine demonstrated the activity in a dose-dependent manner with IC50 value of 51.64 μg/ml. These results support those obtained from synergism assays where by the underlying synergistic antifungal mechanisms could be due to blockage of ABC efflux pumps and increasing the susceptibility of Candida to miconazole.[2] In vivo: In searching for natural products as potential anti-inflammatory agents, 7,4'-Di-O-methylapigenin wasn't evaluated in vivo for its ability to inhibit acute inflammation.[1]

   

[(4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl acetate

[(4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl acetate

C22H32O3 (344.2351)


   

1-{8a-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,6-dimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl 3-{5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl propanedioate

1-{8a-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,6-dimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl 3-{5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl propanedioate

C45H62O8 (730.4444)


   

[(1r,4s,5s,9s,10s,13s)-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methanol

[(1r,4s,5s,9s,10s,13s)-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methanol

C20H32O (288.2453)


   

(7ar)-1,1,7-trimethyl-4-methylidene-octahydrocyclopropa[e]azulen-7-ol

(7ar)-1,1,7-trimethyl-4-methylidene-octahydrocyclopropa[e]azulen-7-ol

C15H24O (220.1827)


   

[(1r,4s,9s,10s,13s)-5-[(acetyloxy)methyl]-9,13-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate

[(1r,4s,9s,10s,13s)-5-[(acetyloxy)methyl]-9,13-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate

C24H36O4 (388.2613)


   

{1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl}methanol

{1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl}methanol

C20H30O3 (318.2195)


   

[(3s,4ar,6ar,7s,10as,10br)-3-ethenyl-3,4a,7,10a-tetramethyl-octahydro-1h-naphtho[2,1-b]pyran-7-yl]methanol

[(3s,4ar,6ar,7s,10as,10br)-3-ethenyl-3,4a,7,10a-tetramethyl-octahydro-1h-naphtho[2,1-b]pyran-7-yl]methanol

C20H34O2 (306.2559)


   

[(1s,2r,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methanol

[(1s,2r,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methanol

C20H30O3 (318.2195)


   

[(1r,4s,5r,9s,10s,13s)-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methanol

[(1r,4s,5r,9s,10s,13s)-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methanol

C20H32O (288.2453)


   

1-{5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl 3-methyl propanedioate

1-{5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl 3-methyl propanedioate

C24H34O5 (402.2406)


   

{5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methanol

{5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methanol

C20H30O2 (302.2246)


   

1-[(4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl 3-ethyl propanedioate

1-[(4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl 3-ethyl propanedioate

C25H36O5 (416.2563)


   

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,8-dimethoxychromen-4-one

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,8-dimethoxychromen-4-one

C18H16O8 (360.0845)


   

1-{5,6,8a-trimethyl-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl 3-{5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl propanedioate

1-{5,6,8a-trimethyl-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl 3-{5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl propanedioate

C43H60O7 (688.4339)


   

1,3-bis{[(4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl} propanedioate

1,3-bis{[(4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl} propanedioate

C43H60O6 (672.439)


   

[(4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methanol

[(4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methanol

C20H30O2 (302.2246)


   

[(1s,4s,5s,9r,10s,13s,14r,16s)-5,9,13-trimethyl-15-oxapentacyclo[11.3.1.0¹,¹⁰.0⁴,⁹.0¹⁴,¹⁶]heptadecan-5-yl]methanol

[(1s,4s,5s,9r,10s,13s,14r,16s)-5,9,13-trimethyl-15-oxapentacyclo[11.3.1.0¹,¹⁰.0⁴,⁹.0¹⁴,¹⁶]heptadecan-5-yl]methanol

C20H32O2 (304.2402)


   

{5-[(acetyloxy)methyl]-1-[2-(furan-3-yl)ethyl]-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl}methyl acetate

{5-[(acetyloxy)methyl]-1-[2-(furan-3-yl)ethyl]-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl}methyl acetate

C24H34O5 (402.2406)


   

{5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl}methanol

{5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl}methanol

C20H32O (288.2453)


   

1-[(4ar,5s,6r,8as)-8a-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,6-dimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl 3-methyl propanedioate

1-[(4ar,5s,6r,8as)-8a-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,6-dimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl 3-methyl propanedioate

C26H36O7 (460.2461)


   

1-{8a-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,6-dimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl 3-methyl propanedioate

1-{8a-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,6-dimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl 3-methyl propanedioate

C26H36O7 (460.2461)


   

3-({5,6,8a-trimethyl-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methoxy)-3-oxopropanoic acid

3-({5,6,8a-trimethyl-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methoxy)-3-oxopropanoic acid

C23H32O6 (404.2199)


   

1,3-bis({8a-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,6-dimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl) propanedioate

1,3-bis({8a-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,6-dimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl) propanedioate

C47H64O10 (788.4499)


   

1-[(4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl 3-[(4ar,5s,6r,8as)-8a-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,6-dimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl propanedioate

1-[(4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl 3-[(4ar,5s,6r,8as)-8a-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,6-dimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl propanedioate

C45H62O8 (730.4444)


   

3-{[(4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy}-3-oxopropanoic acid

3-{[(4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy}-3-oxopropanoic acid

C23H32O6 (404.2199)


   

1-[(4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl 3-methyl propanedioate

1-[(4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl 3-methyl propanedioate

C24H34O5 (402.2406)


   

{5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl acetate

{5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl acetate

C22H32O3 (344.2351)


   

(4as,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6-dimethyl-4,4a,6,7,8,8a-hexahydro-3h-naphthalene-1-carboxylic acid

(4as,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6-dimethyl-4,4a,6,7,8,8a-hexahydro-3h-naphthalene-1-carboxylic acid

C19H26O3 (302.1882)


   

1-[(4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl 3-[(4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl propanedioate

1-[(4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl 3-[(4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl propanedioate

C43H60O7 (688.4339)


   

[(1s,4s,5r,9r,10s,13s,14s,16r)-5,9,13-trimethyl-15-oxapentacyclo[11.3.1.0¹,¹⁰.0⁴,⁹.0¹⁴,¹⁶]heptadecan-5-yl]methanol

[(1s,4s,5r,9r,10s,13s,14s,16r)-5,9,13-trimethyl-15-oxapentacyclo[11.3.1.0¹,¹⁰.0⁴,⁹.0¹⁴,¹⁶]heptadecan-5-yl]methanol

C20H32O2 (304.2402)


   

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6,8-trimethoxychromen-4-one

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6,8-trimethoxychromen-4-one

C19H18O9 (390.0951)


   

{5,9,13-trimethyl-15-oxapentacyclo[11.3.1.0¹,¹⁰.0⁴,⁹.0¹⁴,¹⁶]heptadecan-5-yl}methanol

{5,9,13-trimethyl-15-oxapentacyclo[11.3.1.0¹,¹⁰.0⁴,⁹.0¹⁴,¹⁶]heptadecan-5-yl}methanol

C20H32O2 (304.2402)


   

(4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

(4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

C20H28O3 (316.2038)


   

[(1s,2r,4as,8ar)-5-[(acetyloxy)methyl]-1-[2-(furan-3-yl)ethyl]-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate

[(1s,2r,4as,8ar)-5-[(acetyloxy)methyl]-1-[2-(furan-3-yl)ethyl]-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate

C24H34O5 (402.2406)


   

1-ethyl 3-{5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl propanedioate

1-ethyl 3-{5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl propanedioate

C25H36O5 (416.2563)


   

1,3-bis{[(4ar,5s,6r,8as)-8a-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,6-dimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl} propanedioate

1,3-bis{[(4ar,5s,6r,8as)-8a-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,6-dimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl} propanedioate

C47H64O10 (788.4499)


   

(1as,4as,7s,7ar,7bs)-1,1,7-trimethyl-4-methylidene-octahydrocyclopropa[e]azulen-7-ol

(1as,4as,7s,7ar,7bs)-1,1,7-trimethyl-4-methylidene-octahydrocyclopropa[e]azulen-7-ol

C15H24O (220.1827)


   

{5-[(acetyloxy)methyl]-9,13-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl}methyl acetate

{5-[(acetyloxy)methyl]-9,13-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl}methyl acetate

C24H36O4 (388.2613)


   

1,3-bis({5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl) propanedioate

1,3-bis({5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl}methyl) propanedioate

C43H60O6 (672.439)


   

{3-ethenyl-3,4a,7,10a-tetramethyl-octahydro-1h-naphtho[2,1-b]pyran-7-yl}methanol

{3-ethenyl-3,4a,7,10a-tetramethyl-octahydro-1h-naphtho[2,1-b]pyran-7-yl}methanol

C20H34O2 (306.2559)