corynoline : A benzophenanthridine alkaloid that is chelidonine substituted by a methyl group at position 13. Isolated from the aerial parts of Corydalis incisa, it acts as an acetylcholinesterase inhibitor and also exhibits antineoplastic and hepatoprotective activity. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| Flora | Rank | Flora Definition | Family | Family Definition |
|---|---|---|---|---|
| Corydalis | genus | A plant genus of the family FUMARIACEAE (classified by some in PAPAVERACEAE) that contains isoquinoline alkaloids.[MeSH] | Papaveraceae | The poppy plant family of the order Papaverales, subclass Magnoliidae, class Magnoliopsida. These have bisexual, regular, cup-shaped flowers with one superior pistil and many stamens; 2 or 3 conspicuous, separate sepals and a number of separate petals. The fruit is a capsule. Leaves are usually deeply cut or divided into leaflets.[MeSH] |
| Corydalis incisa | species | [no description available] | Papaveraceae | The poppy plant family of the order Papaverales, subclass Magnoliidae, class Magnoliopsida. These have bisexual, regular, cup-shaped flowers with one superior pistil and many stamens; 2 or 3 conspicuous, separate sepals and a number of separate petals. The fruit is a capsule. Leaves are usually deeply cut or divided into leaflets.[MeSH] |
| ID Source | ID |
|---|---|
| PubMed CID | 177014 |
| CHEMBL ID | 4126384 |
| CHEBI ID | 65660 |
| SCHEMBL ID | 3127828 |
| MeSH ID | M0468824 |
| Synonym |
|---|
| corynoline |
| chelidonine, 13-methyl- |
| zq9w3ju6n3 , |
| (+)-corynoline |
| unii-zq9w3ju6n3 |
| 18797-79-0 |
| S9085 |
| AKOS015896713 |
| 13-methylchelidonine |
| CHEBI:65660 |
| (11s,13r,14r)-corynoline |
| (5br,6s,12br)-5b,13-dimethyl-5b,6,7,12b,13,14-hexahydro[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol |
| SCHEMBL3127828 |
| AC-35078 |
| Q-100225 |
| corynoline, >=98% (hplc) |
| 68035-45-0 |
| HY-N0826 |
| ( inverted exclamation marka)-corynoline |
| DTXSID20940272 |
| bdbm50276146 |
| chembl4126384 , |
| Q15410919 |
| CCG-268252 |
| [1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol, 5b,6,7,12b,13,14-hexahydro-5b,13-dimethyl-, (5br,6s,12br)- |
| CS-0009858 |
| 13,24-dimethyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol |
| (1r,12s,13r)-13,24-dimethyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol |
| AS-75490 |
| (5br,6s,12br)-5b,6,7,12b,13,14-hexahydro-5b,13-dimethyl(1,3)benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridin-6-ol |
| (invertedexclamationmarka)-corynoline |
Corynoline is a 1,3-benzodioxole-containing isoquinoline alkaloid isolated from Corydalis bugeana Turcz., a traditional herbal medicine.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Corynoline is an active substance extracted from " | ( Corynoline ameliorates dextran sulfate sodium-induced colitis in mice by modulating Nrf2/NF-κB pathway. Feng, M; Lang, W; Li, S; Li, Y; Wang, X; Wu, T; Xu, C; Zhang, H; Zhang, Z, 2023) | 3.8 |
| "Corynoline is a 1,3-benzodioxole-containing isoquinoline alkaloid isolated from Corydalis bugeana Turcz., a traditional herbal medicine. " | ( In Vitro and In Vivo Characterization of Reactive Intermediates of Corynoline. Mao, X; Peng, Y; Zheng, J, 2015) | 2.1 |
Corynoline has been reported to have anti-inflammatory and antioxidative effects. It has reportedly demonstrated multiple pharmacologic properties.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Corynoline has been reported to have anti-inflammatory and antioxidative effects. " | ( Corynoline protects against zearalenone-induced liver injury by activating the SIRT1/Nrf2 signaling pathway. He, D; Liu, Y; Sun, L; Wang, L; Wei, Y, 2023) | 3.8 |
| "Corynoline has reportedly demonstrated multiple pharmacologic properties." | ( In Vitro and In Vivo Characterization of Reactive Intermediates of Corynoline. Mao, X; Peng, Y; Zheng, J, 2015) | 1.37 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "Corynoline could inhibit the centrosome clustering required for pseudo-bipolar spindle formation in these cells." | ( The phytochemical, corynoline, diminishes Aurora kinase B activity to induce mitotic defect and polyploidy. Ahire, V; Allen, TD; Li, J; Liu, X; Shi, Q; Yan, Z; Yang, D; Zhang, J; Zhang, S, 2022) | 1.77 |
Corynoline treatment significantly suppressed the paw licking, writhing in the abdominal region, and displayed high nociceptive inhibitory reaction in a dose-related manner. Treatment also significantly increased the expression of Nrf2, quinone oxidoreductase 1 (NQO1) and hemeoxygenase-1 (HO-1) at the mRNA and protein levels.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Corynoline treatment significantly suppressed the paw licking, writhing in the abdominal region, and displayed high nociceptive inhibitory reaction in a dose-related manner." | ( Antinociceptive and Anti-inflammatory Effect of Corynoline in Different Nociceptive and Inflammatory Experimental Models. Lei, F; Yan, Z, 2022) | 1.7 |
| "Treatment with corynoline reduced production of nitric oxide (NO) and the protein and mRNA levels of inducible nitric oxide (iNOS) and cyclooxygenase-2 (COX-2) Treatment also significantly increased the expression of Nrf2, quinone oxidoreductase 1 (NQO1) and hemeoxygenase-1 (HO-1) at the mRNA and protein levels, which demonstrated that corynoline may protect cells from inflammation through the Nrf2/ARE pathway In addition, corynoline suppressed the expression of inflammatory cytokines, such as tumor necrosis factor-α (TNF-α) and interleukin-1β (IL-1β), at the mRNA and protein levels." | ( Corynoline Isolated from Corydalis bungeana Turcz. Exhibits Anti-Inflammatory Effects via Modulation of Nfr2 and MAPKs. Kong, AN; Kuang, H; Tang, Z; Wang, Z; Yang, C; Zhang, C, 2016) | 2.22 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " The method was fully validated and successfully applied in a pharmacokinetic study of corynoline in rats, in which the rats were treated with corynoline, corynoline combined with berberine and the traditional Chinese medicine formula Shuanghua Baihe tablets (SBT, containing corynoline, berberine and other ingredients), respectively." | ( Study on the pharmacokinetic profiles of corynoline and its potential interaction in traditional Chinese medicine formula Shuanghua Baihe tablets in rats by LC-MS/MS. Cheng, M; Ding, L; Gu, P; Liu, R; Liu, Y; Wang, L; Wu, Y; Zheng, L, 2016) | 0.92 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " This study was designed to screen for the anti-inflammatory components from CB based on macrophage binding combined with HPLC." | ( Screening for anti-inflammatory components from Corydalis bungeana Turcz. based on macrophage binding combined with HPLC. Dong, ZB; Feng, L; Li, C; Niu, B; Qi, H; Shao, JG; Tian, G; Zhang, YH; Zhao, BJ, 2015) | 0.42 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " Corynoline showed low bioavailability and a high elimination rate." | ( Study on the pharmacokinetic profiles of corynoline and its potential interaction in traditional Chinese medicine formula Shuanghua Baihe tablets in rats by LC-MS/MS. Cheng, M; Ding, L; Gu, P; Liu, R; Liu, Y; Wang, L; Wu, Y; Zheng, L, 2016) | 1.61 |
| Excerpt | Relevance | Reference |
|---|---|---|
| "2%, respectively, when the same dosage of corynoline was administered in SBT." | ( Study on the pharmacokinetic profiles of corynoline and its potential interaction in traditional Chinese medicine formula Shuanghua Baihe tablets in rats by LC-MS/MS. Cheng, M; Ding, L; Gu, P; Liu, R; Liu, Y; Wang, L; Wu, Y; Zheng, L, 2016) | 0.96 |
| Role | Description |
|---|---|
| metabolite | Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. |
| EC 3.1.1.7 (acetylcholinesterase) inhibitor | An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid. |
| antineoplastic agent | A substance that inhibits or prevents the proliferation of neoplasms. |
| hepatoprotective agent | Any compound that is able to prevent damage to the liver. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| isoquinolines | A class of organic heteropolycyclic compound consisting of isoquinoline and its substitution derivatives. |
| organic heterohexacyclic compound | |
| secondary alcohol | A secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it. |
| cyclic acetal | An acetal in the molecule of which the acetal carbon and one or both oxygen atoms thereon are members of a ring. |
| benzophenanthridine alkaloid | A specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Amine oxidase [flavin-containing] A | Homo sapiens (human) | IC50 (µMol) | 20.0000 | 0.0000 | 2.3789 | 9.7700 | AID1498689 |
| Amine oxidase [flavin-containing] B | Homo sapiens (human) | IC50 (µMol) | 20.0000 | 0.0000 | 1.8914 | 9.5700 | AID1498690 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| mitochondrion | Amine oxidase [flavin-containing] A | Homo sapiens (human) |
| mitochondrial outer membrane | Amine oxidase [flavin-containing] A | Homo sapiens (human) |
| cytosol | Amine oxidase [flavin-containing] A | Homo sapiens (human) |
| mitochondrion | Amine oxidase [flavin-containing] A | Homo sapiens (human) |
| mitochondrion | Amine oxidase [flavin-containing] B | Homo sapiens (human) |
| mitochondrial envelope | Amine oxidase [flavin-containing] B | Homo sapiens (human) |
| mitochondrial outer membrane | Amine oxidase [flavin-containing] B | Homo sapiens (human) |
| dendrite | Amine oxidase [flavin-containing] B | Homo sapiens (human) |
| neuronal cell body | Amine oxidase [flavin-containing] B | Homo sapiens (human) |
| mitochondrion | Amine oxidase [flavin-containing] B | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1497528 | Antiinflammatory activity against mouse RAW264.7 cells assessed as inhibition of LPS induced nitric oxide production preincubated for 2 hrs followed by LPS challenge measured after 24 hrs by Griess reagent based assay | 2018 | Bioorganic & medicinal chemistry letters, 07-15, Volume: 28, Issue:13 | Hexahydrobenzophenanthridine alkaloids from Corydalis bungeana Turcz. and their anti-inflammatory activity. |
| AID1498688 | Inhibition of recombinant human MAO-B assessed as residual activity at 20 uM using benzylamine as substrate incubated for 30 mins by spectrophotometric method relative to control | 2018 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14 | Selective inhibition of monoamine oxidase A by chelerythrine, an isoquinoline alkaloid. |
| AID1498689 | Inhibition of recombinant human MAO-A using kynuramine as substrate incubated for 20 mins by spectrophotometric method | 2018 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14 | Selective inhibition of monoamine oxidase A by chelerythrine, an isoquinoline alkaloid. |
| AID1498690 | Inhibition of recombinant human MAO-B using benzylamine as substrate incubated for 30 mins by spectrophotometric method | 2018 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14 | Selective inhibition of monoamine oxidase A by chelerythrine, an isoquinoline alkaloid. |
| AID1498687 | Inhibition of recombinant human MAO-A assessed as residual activity at 20 uM using kynuramine as substrate incubated for 20 mins by spectrophotometric method relative to control | 2018 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14 | Selective inhibition of monoamine oxidase A by chelerythrine, an isoquinoline alkaloid. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 2 (8.00) | 29.6817 |
| 2010's | 11 (44.00) | 24.3611 |
| 2020's | 12 (48.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (21.53) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 25 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||