CHEBI:6641 - (S)-magnoflorine

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ChEBI Name (S)-magnoflorine
ChEBI ID CHEBI:6641
ChEBI ASCII Name (S)-magnoflorine
Definition An aporphine alkaloid that is (S)-corytuberine in which the nitrogen has been quaternised by an additional methyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB0350572, ZINC000000519823
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Formula C20H24NO4
Net Charge +1
Average Mass 342.410
Monoisotopic Mass 342.16998
InChI InChI=1S/C20H23NO4/c1-21(2)8-7-12-10-15(25-4)20(23)18-16(12)13(21)9-11-5-6-14(24-3)19(22)17(11)18/h5-6,10,13H,7-9H2,1-4H3,(H-,22,23)/p+1/t13-/m0/s1
InChIKey YLRXAIKMLINXQY-ZDUSSCGKSA-O
SMILES C12=C3C4=C(C=CC(=C4O)OC)C[C@@]1([N+](CCC2=CC(=C3O)OC)(C)C)[H]
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (S)-magnoflorine (CHEBI:6641) has functional parent (S)-corytuberine (CHEBI:81200)
(S)-magnoflorine (CHEBI:6641) has role plant metabolite (CHEBI:76924)
(S)-magnoflorine (CHEBI:6641) is a aporphine alkaloid (CHEBI:134209)
(S)-magnoflorine (CHEBI:6641) is a quaternary ammonium ion (CHEBI:35267)
IUPAC Name
(6aS)-1,11-dihydroxy-2,10-dimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolinium
Synonyms Sources
(+)-magnoflorine ChemIDplus
magnoflorine UniProt
magnoflorine ChemIDplus
Manual Xrefs Databases
C00001885 KNApSAcK
C09581 KEGG COMPOUND
CPD-9936 MetaCyc
Magnoflorine Wikipedia
View more database links
Registry Numbers Types Sources
1553619 Reaxys Registry Number Reaxys
2141-09-5 CAS Registry Number ChemIDplus
Citations
Xue B, Zhao Y, Su J, Miao Q, Miao P, Chen N, Wang Z, Zhang Y, Ma S (2017)
In Vitro Intestinal Absorption and Metabolism of Magnoflorine and its Potential Interaction in Coptidis Rhizoma Decoction in Rat.
European journal of drug metabolism and pharmacokinetics 42, 281-293 [PubMed:27209587]
[show Abstract]
Tian X, Zhang Y, Li Z, Hu P, Chen M, Sun Z, Lin Y, Pan G, Huang C (2016)
Systematic and comprehensive strategy for metabolite profiling in bioanalysis using software-assisted HPLC-Q-TOF: magnoflorine as an example.
Analytical and bioanalytical chemistry 408, 2239-2254 [PubMed:26873213]
[show Abstract]
Morris JS, Facchini PJ (2016)
Isolation and Characterization of Reticuline N-Methyltransferase Involved in Biosynthesis of the Aporphine Alkaloid Magnoflorine in Opium Poppy.
The Journal of biological chemistry 291, 23416-23427 [PubMed:27634038]
[show Abstract]
Xue B, Zhao Y, Miao Q, Miao P, Yang X, Sun G, Su J, Ye J, Wei B, Zhang Y, Zhang Y (2015)
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.
Biomedical chromatography : BMC 29, 1235-1248 [PubMed:25611590]
[show Abstract]
Bao S, Geng P, Wang S, Zhou Y, Hu L, Yang X (2015)
Pharmacokinetics in rats and tissue distribution in mouse of magnoflorine by ultra performance liquid chromatography-tandem mass spectrometry.
International journal of clinical and experimental medicine 8, 20168-20177 [PubMed:26884929]
[show Abstract]
Sakumoto H, Yokota Y, Ishibashi G, Maeda S, Hoshi C, Takano H, Kobayashi M, Yahagi T, Ijiri S, Sakakibara I, Hara A (2015)
Sinomenine and magnoflorine, major constituents of Sinomeni caulis et rhizoma, show potent protective effects against membrane damage induced by lysophosphatidylcholine in rat erythrocytes.
Journal of natural medicines 69, 441-448 [PubMed:25840917]
[show Abstract]
Tian X, Li Z, Lin Y, Chen M, Pan G, Huang C (2014)
Study on the PK profiles of magnoflorine and its potential interaction in Cortex phellodendri decoction by LC-MS/MS.
Analytical and bioanalytical chemistry 406, 841-849 [PubMed:24337185]
[show Abstract]
Kim WI, Zhao BT, Zhang HY, Lee JH, Son JK, Woo MH (2014)
Quantitative and pattern recognition analyses of magnoflorine, spinosin, 6'''-feruloyl spinosin and jujuboside A by HPLC in Zizyphi Semen.
Archives of pharmacal research 37, 1139-1147 [PubMed:24310099]
[show Abstract]
de la Peña JB, Lee HL, Yoon SY, Kim GH, Lee YS, Cheong JH (2013)
The involvement of magnoflorine in the sedative and anxiolytic effects of Sinomeni Caulis et Rhizoma in mice.
Journal of natural medicines 67, 814-821 [PubMed:23456265]
[show Abstract]
Gao M, Liu J, Sun X, Huang W, Guo B, Xiao P (2011)
[The HPLC determination of the content of magnoflorine in main species of Epimedii Herba].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 36, 16-18 [PubMed:21473145]
[show Abstract]
Arevalo C, Lotti C, Piccinelli AL, Russo M, Ruiz I, Rastrelli L (2009)
Magnoflorine and phenolic derivatives from the leaves of Croton xalapensis L. (Euphorbiaceae).
Natural product communications 4, 1697-1700 [PubMed:20120110]
[show Abstract]
Hung TM, Na M, Min BS, Zhang X, Lee I, Ngoc TM, Thuong PT, Sok DE, Bae K (2007)
Protective effect of magnoflorine isolated from coptidis rhizoma on Cu2+-induced oxidation of human low density lipoprotein.
Planta medica 73, 1281-1284 [PubMed:17973202]
[show Abstract]
Last Modified
04 January 2017