Magnoflorine is a naturally occurring aporphine alkaloid found in several plants of the family Annonaceae. It exhibits various pharmacological activities, including anti-inflammatory, analgesic, anticonvulsant, and anticancer effects. Its synthesis has been achieved through various methods, including the Pictet-Spengler reaction and the Bischler-Napieralski reaction. The diverse biological activities of magnoflorine have garnered interest in its potential therapeutic applications. Research focuses on understanding its mechanisms of action, optimizing its synthesis, and evaluating its efficacy in preclinical and clinical studies.'
magnoflorine: opium alkaloid having the aporphine configuration; RN given refers to parent cpd(S)-isomer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
(S)-magnoflorine : An aporphine alkaloid that is (S)-corytuberine in which the nitrogen has been quaternised by an additional methyl group. [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]
| ID Source | ID |
|---|---|
| PubMed CID | 73337 |
| CHEMBL ID | 235428 |
| CHEBI ID | 6641 |
| MeSH ID | M0041941 |
| Synonym |
|---|
| 4h-dibenzo(de,g)quinolinium, 5,6,6a,7-tetrahydro-1,11-dihydroxy-2,10-dimethoxy-6,6-dimethyl-,(6as)- |
| thalictrine |
| thalictrin |
| 6a-alpha-aporphinium, 1,11-dihydroxy-2,10-dimethoxy-6-methyl- |
| escholin |
| escholine |
| 5,6,6a(s),7-tetrahydro-1,11-dihydroxy-2,10-dimethoxy-6,6-dimethyl-4h-dibenzo[de,g]quinolinium chloride |
| (s)-magnoflorine |
| C09581 |
| 2141-09-5 |
| magnoflorine |
| (6as)-1,11-dihydroxy-2,10-dimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinolinium |
| chebi:6641 , |
| CHEMBL235428 |
| S9089 |
| (+)-magnoflorine |
| ni8k6962k4 , |
| unii-ni8k6962k4 |
| (6as)-5,6,6a,7-tetrahydro-1,11-dihydroxy-2,10-dimethoxy-6,6-dimethyl-4h-dibenzo(de,g)quinolinium |
| magnoflorine [mi] |
| .alpha.-magnoflorine |
| esholine |
| corytuberine methosalt |
| magnoflorine, >=98% (hplc) |
| AKOS032948336 |
| mfcd09031380 |
| DTXSID90943972 , |
| HY-N0334 |
| Q15426208 |
| 5,6,6as,7-tetrahydro-1,11-dihydroxy-2,10-dimethoxy-6,6-dimethyl-4h-dibenzo[de,g]quinolinium |
| (6as)-2,10-dimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinolin-6-ium-1,11-diol |
| CS-0008895 |
| CCG-267949 |
| magnoflorine (iodide);-magnoflorine (iodide);thalictrine (iodide) |
| dtxcid601372329 |
| (6as)-1,11-dihydroxy-2,10-dimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4h-dibenzo(de,g)quinolinium |
| alpha-magnoflorine |
Magnoflorine is an aporphine alkaloid present in plant species belonging to the Berberidaceae, Magnoliaceae, Menispermaceae, or Papaveraceae botanical families. It has good anti-inflammatory and antioxidant effects.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Magnoflorine was found to inhibit the copper-mediated (Cu2+) oxidation of LDL, as well as of glycated and glycoxidated LDL by increasing the lag time of conjugated diene formation and preventing the generation of thiobarbituric acid reactive substances (TBARS)." | ( Protective effect of magnoflorine isolated from coptidis rhizoma on Cu2+-induced oxidation of human low density lipoprotein. Bae, K; Hung, TM; Lee, I; Min, BS; Na, M; Ngoc, TM; Sok, DE; Thuong, PT; Zhang, X, 2007) | 1.38 |
The validated method was successfully used for pharmacokinetic studies of magnoflorine in rat plasma after intravenous administration. This review provides the first comprehensive summary of the plant sources, pharmacological effects, toxicity, and pharmacokinetics characteristics of magnflorine. The selective, sensitive and accurate high-performance liquid chromatography-electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS) method was developed and validated.
ine has low bioavailability and high absorption and elimination rates. Studies showed that magnoflorine possessed lower bioavailability.
| Excerpt | Reference | Relevance |
|---|---|---|
| " Studies showed that magnoflorine possessed lower bioavailability and faster absorption and elimination." | ( In vitro and in vivo identification of metabolites of magnoflorine by LC LTQ-Orbitrap MS and its potential pharmacokinetic interaction in Coptidis Rhizoma decoction in rat. Miao, P; Miao, Q; Su, J; Sun, G; Wei, B; Xue, B; Yang, X; Ye, J; Zhang, Y; Zhao, Y, 2015) | 0.98 |
| " Pharmacokinetic studies have shown that magnoflorine has low bioavailability and high absorption and elimination rates." | ( Magnoflorine: A review of its pharmacology, pharmacokinetics and toxicity. Du, H; Fan, G; Feng, T; Kuang, T; Li, Q; Xu, T; Zhang, Y, 2020) | 2.27 |
The excretion of magnoflorine in rat bile, urine, and feces in 24 h was observed. The rats were given Coptidis Rhizoma decoction (equivalent to 30 mg kg(-1) of magnflorine) by intragastric administration.
| Excerpt | Relevance | Reference |
|---|---|---|
| " In a pharmacokinetic study, rats were not only dosed with magnoflorine via oral (15, 30 and 60 mg kg(-1) ) and intravenous administration (10 mg kg(-1) ) but also dosed with Coptidis Rhizoma decoction (equivalent to 30 mg kg(-1) of magnoflorine) by intragastric administration to investigate the interaction of magnoflorine with the rest of compounds in Coptidis Rhizoma." | ( In vitro and in vivo identification of metabolites of magnoflorine by LC LTQ-Orbitrap MS and its potential pharmacokinetic interaction in Coptidis Rhizoma decoction in rat. Miao, P; Miao, Q; Su, J; Sun, G; Wei, B; Xue, B; Yang, X; Ye, J; Zhang, Y; Zhao, Y, 2015) | 0.91 |
| " The rats were dosed with magnoflorine(30 mg·kg~(-1)) and water decoction of Coptidis Rhizoma(equivalent to 30 mg·kg~(-1) magnoflorine) via intragastric administration, and magnoflorine(10 mg·kg~(-1)) by intravenous administration, respectively, and the excretion of magnoflorine in rat bile, urine, and feces in 24 h was observed." | ( [Influence of coexisting components in Coptidis Rhizoma on excretion of magnoflorine in rat bile, urine, and feces]. Chen, JH; Sun, XR; Xue, BJ; Zhang, YJ; Zhang, Z; Zhao, WW, 2022) | 1.25 |
| Role | Description |
|---|---|
| plant metabolite | Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| [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 |
|---|---|
| aporphine alkaloid | Any benzylisoquinoline alkaloid that has a structure based on 4H-dibenzo[de,g]quinoline or its 3-methyl derivative. |
| quaternary ammonium ion | A derivative of ammonium, NH4(+), in which all four of the hydrogens bonded to nitrogen have been replaced with univalent (usually organyl) groups. |
| [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] | |
| Pathway | Proteins | Compounds |
|---|---|---|
| magnoflorine biosynthesis | 0 | 8 |
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID377158 | Teratogenic activity in rat embryo assessed as incidence of major malformation at 5 ug/mL after 45 hrs relative to control | 1999 | Journal of natural products, Oct, Volume: 62, Issue:10 | Detecting potential teratogenic alkaloids from blue cohosh rhizomes using an in vitro rat embryo culture. |
| AID1653975 | Protection against DNCB-induced skin inflammation in BALB/c mouse model of atopic dermatitis assessed as reduction in spleen index at 0.1 g/ml administered topically once daily for 16 days measured post last dose | |||
| AID1432744 | Induction of myoblast differentiation in mouse C2C12 cells assessed as increase in MHC protein expression after 2 days by Western blot analysis | 2017 | Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6 | Isoquinoline alkaloids from Coptis japonica stimulate the myoblast differentiation via p38 MAP-kinase and Akt signaling pathway. |
| AID1653958 | Protection against DNCB-induced skin inflammation in BALB/c mouse model of atopic dermatitis assessed as reduction in skin erosion at 0.1 g/ml administered topically once daily for 16 days measured post last dose | |||
| AID399826 | Toxicity in ip dosed mouse assessed as labored breathing and depression at LD50 | |||
| AID1653963 | Inhibition of TNFalpha/IFN-gamma-induced apoptosis in human HaCaT cells assessed as rounded nuclei with sharp edges at 500 to 1500 ug/ml after 24 hrs by Hoechst staining based fluorescence microscopic analysis | |||
| AID1653956 | Inhibition of TNF-alpha/IFN-gamma-induced apoptosis in human HaCaT cells assessed as apoptotic rate at 1500 ug/ml after 24 hrs by Annexin V-FITC/propidium iodide double staining-based flow cytometry (Rvb = 42.9%) | |||
| AID1653978 | Induction of apoptosis in human HaCaT cells at 500 to 1500 ug/ml after 24 hrs by Hoechst staining based fluorescence microscopic analysis | |||
| AID1432743 | Induction of myoblast differentiation in mouse C2C12 cells expressing MyoD-responsive 4RTK-Luc assessed as increase in MHC protein expression at 10 nM after 2 days by Western blot analysis | 2017 | Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6 | Isoquinoline alkaloids from Coptis japonica stimulate the myoblast differentiation via p38 MAP-kinase and Akt signaling pathway. |
| AID1653977 | Protection against DNCB-induced skin inflammation in BALB/c mouse model of atopic dermatitis assessed as reduction in hair follicle disappearance at 0.1 g/ml administered topically once daily for 16 days measured post last dose | |||
| AID1653973 | Protection against DNCB-induced skin inflammation in BALB/c mouse model of atopic dermatitis assessed as reduction in IgE level at 0.1 g/ml administered topically once daily for 16 days measured post last dose by ELISA | |||
| AID1653966 | Inhibition of TNFalpha/IFN-gamma-induced apoptosis in human HaCaT cells assessed as increase in caspase 3 expression at 500 ug/ml after 24 hrs by Western blot analysis | |||
| AID1432747 | Induction of myoblast differentiation in mouse C2C12 cells assessed as cylinder shaped multinucleated myotubes after 2 days by DAPI staining based immunofluorescence assay | 2017 | Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6 | Isoquinoline alkaloids from Coptis japonica stimulate the myoblast differentiation via p38 MAP-kinase and Akt signaling pathway. |
| AID1653957 | Protection against DNCB-induced skin inflammation in BALB/c mouse model of atopic dermatitis assessed as reduction in skin erythema at 0.1 g/ml administered topically once daily for 16 days measured post last dose | |||
| AID399827 | Toxicity in ip dosed mouse assessed as death at LD50 | |||
| AID1653976 | Protection against DNCB-induced skin inflammation in BALB/c mouse model of atopic dermatitis assessed as reduction in dermal edema at 0.1 g/ml administered topically once daily for 16 days measured post last dose | |||
| AID377151 | Effect on growth and morphogenesis of organogenesis-staged rat embryo at 1.25 ug/mL after 45 hrs relative to control | 1999 | Journal of natural products, Oct, Volume: 62, Issue:10 | Detecting potential teratogenic alkaloids from blue cohosh rhizomes using an in vitro rat embryo culture. |
| AID377157 | Effect on growth and morphogenesis of organogenesis-staged rat embryo at 250 ug/mL after 45 hrs relative to control | 1999 | Journal of natural products, Oct, Volume: 62, Issue:10 | Detecting potential teratogenic alkaloids from blue cohosh rhizomes using an in vitro rat embryo culture. |
| AID1653960 | Protection against DNCB-induced skin inflammation in BALB/c mouse model of atopic dermatitis assessed as number of caspase-3 positive cells at 0.1 g/ml administered topically once daily for 16 days measured post last dose by hematoxylin staining based lig | |||
| AID399824 | Toxicity in ip dosed mouse | |||
| AID1653972 | Toxicity in DNCB-induced skin inflammation in BALB/c mouse model of atopic dermatitis assessed as effect on organs at 0.1 g/ml administered topically once daily for 16 days | |||
| AID1653959 | Protection against DNCB-induced skin inflammation in BALB/c mouse model of atopic dermatitis assessed as reduction in skin dryness at 0.1 g/ml administered topically once daily for 16 days measured post last dose | |||
| AID301052 | Antiviral activity against HBV transfected Hep G2.2.15 cells assessed as inhibition of e antigen HBsAg secretion | 2007 | Bioorganic & medicinal chemistry letters, Oct-01, Volume: 17, Issue:19 | Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida. |
| AID377154 | Effect on growth and morphogenesis of organogenesis-staged rat embryo at 50 ug/mL after 45 hrs relative to control | 1999 | Journal of natural products, Oct, Volume: 62, Issue:10 | Detecting potential teratogenic alkaloids from blue cohosh rhizomes using an in vitro rat embryo culture. |
| AID377149 | Teratogenic activity in rat embryo assessed as incidence of major malformation at 1.25 ug/mL after 45 hrs relative to control | 1999 | Journal of natural products, Oct, Volume: 62, Issue:10 | Detecting potential teratogenic alkaloids from blue cohosh rhizomes using an in vitro rat embryo culture. |
| AID1653969 | Inhibition of TNFalpha/IFN-gamma-induced apoptosis in human HaCaT cells assessed as increase in caspase 9 expression at 500 ug/ml after 24 hrs by Western blot analysis | |||
| AID377159 | Teratogenic activity in rat embryo assessed as incidence of major malformation at 20 ug/mL after 45 hrs relative to control | 1999 | Journal of natural products, Oct, Volume: 62, Issue:10 | Detecting potential teratogenic alkaloids from blue cohosh rhizomes using an in vitro rat embryo culture. |
| AID377153 | Effect on growth and morphogenesis of organogenesis-staged rat embryo at 20 ug/mL after 45 hrs relative to control | 1999 | Journal of natural products, Oct, Volume: 62, Issue:10 | Detecting potential teratogenic alkaloids from blue cohosh rhizomes using an in vitro rat embryo culture. |
| AID1432741 | Induction of MyoD transcriptional activity in mouse C2C12 cells expressing MyoD-responsive 4RTK-Luc at 10 nM after 24 hrs by luciferase reporter gene assay | 2017 | Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6 | Isoquinoline alkaloids from Coptis japonica stimulate the myoblast differentiation via p38 MAP-kinase and Akt signaling pathway. |
| AID1653970 | Inhibition of TNFalpha/IFN-gamma-induced apoptosis in human HaCaT cells assessed as increase in cathepsin B expression at 500 ug/ml after 24 hrs by Western blot analysis | |||
| AID1432746 | Induction of myoblast differentiation in mouse C2C12 cells assessed as increase in MHC expression after 2 days by DAPI staining based immunofluorescence assay | 2017 | Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6 | Isoquinoline alkaloids from Coptis japonica stimulate the myoblast differentiation via p38 MAP-kinase and Akt signaling pathway. |
| AID1653967 | Inhibition of TNFalpha/IFN-gamma-induced apoptosis in human HaCaT cells assessed as increase in caspase 7 expression at 500 ug/ml after 24 hrs by Western blot analysis | |||
| AID301051 | Antiviral activity against HBV transfected Hep G2.2.15 cells assessed as inhibition of surface antigen HBsAg secretion | 2007 | Bioorganic & medicinal chemistry letters, Oct-01, Volume: 17, Issue:19 | Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida. |
| AID1432742 | Cytotoxicity against mouse C2C12 cells at 10 nM up to 24 hrs | 2017 | Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6 | Isoquinoline alkaloids from Coptis japonica stimulate the myoblast differentiation via p38 MAP-kinase and Akt signaling pathway. |
| AID399825 | Effect on behavioral activity in ip dosed mouse assessed as occurrence of mydriasis for 30 mins | |||
| AID301050 | Cytotoxicity against human Hep G2.2.15 cells | 2007 | Bioorganic & medicinal chemistry letters, Oct-01, Volume: 17, Issue:19 | Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida. |
| AID1653955 | Inhibition of TNF-alpha/IFN-gamma-induced apoptosis in human HaCaT cells after 24 hrs by Annexin V-FITC/propidium iodide double staining-based flow cytometry | |||
| AID377152 | Effect on growth and morphogenesis of organogenesis-staged rat embryo at 5 ug/mL after 45 hrs relative to control | 1999 | Journal of natural products, Oct, Volume: 62, Issue:10 | Detecting potential teratogenic alkaloids from blue cohosh rhizomes using an in vitro rat embryo culture. |
| AID377156 | Effect on growth and morphogenesis of organogenesis-staged rat embryo at 80 ug/mL after 45 hrs relative to control | 1999 | Journal of natural products, Oct, Volume: 62, Issue:10 | Detecting potential teratogenic alkaloids from blue cohosh rhizomes using an in vitro rat embryo culture. |
| AID1653961 | Inhibition of TNFalpha/IFN-gamma-induced apoptosis in human HaCaT cells assessed as change in mitochondrial membrane potential at 500 ug/ml after 24 hrs by DiOC6 probe based flow cytometric analysis (Rvb = 15.36 +/- 0.76 No_unit) | |||
| AID1653974 | Protection against DNCB-induced skin inflammation in BALB/c mouse model of atopic dermatitis assessed as reduction in IL4 level at 0.1 g/ml administered topically once daily for 16 days measured post last dose by ELISA | |||
| AID1432749 | Induction of Akt phosphorylation in mouse C2C12 cells up to 10 nM after 2 days by Western blot analysis | 2017 | Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6 | Isoquinoline alkaloids from Coptis japonica stimulate the myoblast differentiation via p38 MAP-kinase and Akt signaling pathway. |
| AID1653968 | Inhibition of TNFalpha/IFN-gamma-induced apoptosis in human HaCaT cells assessed as increase in caspase 8 expression at 500 ug/ml after 24 hrs by Western blot analysis | |||
| AID1653971 | Cytotoxicity against human HaCaT cells assessed as reduction in cell viability after 24 hrs by MTT assay | |||
| AID1653962 | Inhibition of TNFalpha/IFN-gamma-induced apoptosis in human HaCaT cells assessed as increase in mitochondrial membrane potential after 24 hrs by DiOC6 probe based flow cytometric analysis | |||
| AID335152 | Antimalarial activity after 24 hrs against chloroquine-resistant Plasmodium falciparum W2 infected type A+ human erythrocytes by [3H]hypoxanthine uptake | 1993 | Journal of natural products, Sep, Volume: 56, Issue:9 | Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei. |
| AID1653965 | Inhibition of TNFalpha/IFN-gamma-induced apoptosis in human HaCaT cells assessed as increase in cytochrome C expression at 500 ug/ml after 24 hrs by Western blot analysis | |||
| AID1653964 | Inhibition of TNFalpha/IFN-gamma-induced apoptosis in human HaCaT cells assessed as increase in Bid expression at 500 ug/ml after 24 hrs by Western blot analysis | |||
| AID335151 | Antimalarial activity after 24 hrs against chloroquine-sensitive Plasmodium falciparum D6 infected type A+ human erythrocytes by [3H]hypoxanthine uptake | 1993 | Journal of natural products, Sep, Volume: 56, Issue:9 | Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei. |
| AID377161 | Teratogenic activity in rat embryo assessed as incidence of major malformation at 80 ug/mL after 45 hrs relative to control | 1999 | Journal of natural products, Oct, Volume: 62, Issue:10 | Detecting potential teratogenic alkaloids from blue cohosh rhizomes using an in vitro rat embryo culture. |
| AID1432745 | Induction of myoblast differentiation in mouse C2C12 cells assessed as increase in MyoD protein expression after 2 days by Western blot analysis | 2017 | Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6 | Isoquinoline alkaloids from Coptis japonica stimulate the myoblast differentiation via p38 MAP-kinase and Akt signaling pathway. |
| AID1432748 | Induction of p38 MAPK phosphorylation in mouse C2C12 cells at 0.1 nM after 2 days by Western blot analysis relative to control | 2017 | Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6 | Isoquinoline alkaloids from Coptis japonica stimulate the myoblast differentiation via p38 MAP-kinase and Akt signaling pathway. |
| AID377150 | Effect on growth and morphogenesis of organogenesis-staged rat embryo at 0.1 ug/mL after 45 hrs relative to control | 1999 | Journal of natural products, Oct, Volume: 62, Issue:10 | Detecting potential teratogenic alkaloids from blue cohosh rhizomes using an in vitro rat embryo culture. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 7 (8.14) | 18.7374 |
| 1990's | 8 (9.30) | 18.2507 |
| 2000's | 13 (15.12) | 29.6817 |
| 2010's | 38 (44.19) | 24.3611 |
| 2020's | 20 (23.26) | 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 (32.85) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 3 (3.41%) | 6.00% |
| Case Studies | 1 (1.14%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 84 (95.45%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||