Magnoflorine
{{Chembox
| ImageFile = Magnoflorine Structural Formula V1.svg
| ImageClass = skin-invert-image
| ImageSize = 200px
| ImageAlt =
| IUPACName = 1,11-Dihydroxy-2,10-dimethoxy-6-methylaporphin-6-ium
| SystematicName = (6aS)-1,11-Dihydroxy-2,10-dimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-ium
| OtherNames = Magnoflorine; Thalictrin; Escholin; Escholine; Thalictrine
|Section1={{Chembox Identifiers
| CASNo = 2141-09-5
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 73337
| ChEBI = 6641
| KEGG = C09581
| UNII = NI8K6962K4
| UNII_Ref = {{fdacite|correct|FDA}}
| ChemSpiderID = 66066
| SMILES = C[N+]1(CCC2=CC(=C(C3=C2[C@@H]1CC4=C3C(=C(C=C4)OC)O)O)OC)C
| StdInChI = 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
| StdInChIKey = YLRXAIKMLINXQY-ZDUSSCGKSA-O}}
|Section2={{Chembox Properties
| Formula = C20H24NO4+
| MolarMass = 342.41 g/mol
| Appearance =
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|Section3={{Chembox Hazards
| MainHazards =
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(S)-Magnoflorine is a quaternary benzylisoquinoline alkaloid (BIA) of the aporphine structural subgroup which has been isolated from various species of the family Menispermaceae, such as Pachygone ovata,{{Cite journal|last1=El-Kawi|first1=M. A.|last2=Slatkin|first2=D. J.|last3=Schiff|first3=P. L.|last4=Dasgupta|first4=S|last5=Chattopadhyay|first5=S. K.|last6=Ray|first6=A. B.|date=1984|title=Additional alkaloids of Pachygone ovata|journal=J Nat Prod|volume=47|issue=3|pages=459–64|doi=10.1021/np50033a010|pmid=6481360 }} Sinomenium acutum,{{cite journal|date=Oct 2013|title=The involvement of magnoflorine in the sedative and anxiolytic effects of Sinomeni Caulis et Rhizoma in mice|journal=J Nat Med|volume=67|pages=814–21|doi=10.1007/s11418-013-0754-3|pmid=23456265|last1=de la Peña|first1=June Bryan I.|last2=Lee|first2=Hye Lim|last3=Yoon|first3=Seo Young|last4=Kim|first4=Gun Hee|last5=Lee|first5=Yong Soo|last6=Cheong|first6=Jae Hoon|issue=4|s2cid=14170353}} and Cissampelos pareira.{{Cite journal|last1=Bala|first1=M|last2=Kumar|first2=S|last3=Pratap|first3=K|last4=Verma|first4=P. K.|last5=Padwad|first5=Y|last6=Singh|first6=B|date=2019|title=Bioactive isoquinoline alkaloids from Cissampelos pareira|journal=Nat Prod Res|volume=33|issue=5|pages=622–627|doi=10.1080/14786419.2017.1402319|pmid=29126362|s2cid=9548987|url=https://figshare.com/articles/journal_contribution/5592778}}
It was identified among the verified anti-inflammatory components in an extract of Sinomenii caulis{{Cite journal|last1=Wang|first1=Lan-Jin|last2=Jiang|first2=Zhen-Meng|last3=Xiao|first3=Ping-Ting|last4=Sun|first4=Jian-Bo|last5=Bi|first5=Zhi-Ming|last6=Liu|first6=E-Hu|date=2019|title=Identification of anti-inflammatory components in Sinomenii Caulis based on spectrum-effect relationship and chemometric methods|journal=J Pharm Biomed Anal|volume=167|pages=38–48|doi=10.1016/j.jpba.2019.01.047|pmid=30738242|s2cid=73436808}} and has been proposed to have other potential physiological effects, such as sedative and anxiolytic, reduction of erythrocyte hemolysis,{{Cite journal|last1=Sakumoto|first1=Hitoshi|last2=Yokota|first2=Yumiko|last3=Ishibashi|first3=Gakushi|last4=Maeda|first4=Shouta|last5=Hoshi|first5=Chihiro|last6=Takano|first6=Haruyo|last7=Kobayashi|first7=Miki|last8=Yahagi|first8=Tadahiro|last9=Ijiri|first9=Soichiro|date=2015|title=Sinomenine and magnoflorine, major constituents of Sinomeni Caulis et Rhizoma, show potent protective effects against membrane damage induced by lysophosphatidylcholine in rat erythrocytes|journal=J Nat Med|volume=69|issue=3|pages=441–8|doi=10.1007/s11418-015-0907-7|pmid=25840917|s2cid=13871437}} antifungal activity,{{Cite journal|last1=Kim|first1=Jaegoo|last2=Ha Quang Bao|first2=Thinh|last3=Shin|first3=Yu-Kyong|last4=Kim|first4=Ki-Young|date=2018|title=Antifungal activity of magnoflorine against Candida strains|journal=World J Microbiol Biotechnol|volume=34|issue=11|pages=167|doi=10.1007/s11274-018-2549-x|pmid=30382403|s2cid=53195579}} improvement of LPS-induced acute lung injury,{{Cite journal|last1=Guo|first1=Shuai|last2=Jiang|first2=Kangfeng|last3=Wu|first3=Haichong|last4=Yang|first4=Chao|last5=Yang|first5=Yaping|last6=Yang|first6=Jing|last7=Zhao|first7=Gan|last8=Deng|first8=Ganzhen|date=2018|title=Magnoflorine Ameliorates Lipopolysaccharide-Induced Acute Lung Injury via Suppressing NF-κB and MAPK Activation|journal=Front. Pharmacol.|volume=9|pages=982|doi=10.3389/fphar.2018.00982|pmid=30214410|pmc=6125611|doi-access=free}} and protection against muscle atrophy.{{Cite journal|last1=Lee|first1=Heyjin|last2=Tuong|first2=Le Thi|last3=Jeong|first3=Ji Hye|last4=Lee|first4=Sang-Jin|last5=Bae|first5=Gyu-Un|last6=Ryu|first6=Jae-Ha|date=2017|title=Isoquinoline alkaloids from Coptis japonica stimulate the myoblast differentiation via p38 MAP-kinase and Akt signaling pathway|journal=Bioorg Med Chem Lett|volume=27|issue=6|pages=1401–1404|doi=10.1016/j.bmcl.2017.02.003|pmid=28228365}} Furthermore, magnoflorine has been identified to be an inhibitor of NF-κB activation and to be an agonist at the β2 -adrenergic receptor.{{Cite journal|last1=Sun|first1=Dan|last2=Han|first2=Yanqi|last3=Wang|first3=Weiya|last4=Wang|first4=Zengyong|last5=Ma|first5=Xiaoyao|last6=Hou|first6=Yuanyuan|last7=Bai|first7=Gang|date=2016|title=Screening and identification of Caulis Sinomenii bioactive ingredients with dual-target NF-κB inhibition and β2-AR agonizing activities|journal=Biomed Chromatogr|volume=30|issue=11|pages=1843–1853|doi=10.1002/bmc.3761|pmid=27187693}}
(S)-Magnoflorine is metabolically derived from (S)-reticuline, a pivotal intermediate in the biosynthesis of numerous BIA structural subgroups, through two enzymatic steps: first, (S)-corytuberine synthase/CYP80G2 to (S)-corytuberine, and secondly, (S)-corytuberine-N-methyltransferase to (S)-magnoflorine.{{Cite journal|last1=Morris|first1=Jeremy S|last2=Facchini|first2=Peter J|date=2016|title=Isolation and Characterization of Reticuline N-Methyltransferase Involved in Biosynthesis of the Aporphine Alkaloid Magnoflorine in Opium Poppy|journal=J Biol Chem|volume=291|issue=45|pages=23416–23427|doi=10.1074/jbc.M116.750893|pmid=27634038|pmc=5095398|doi-access=free}}{{Cite journal|last1=He|first1=Si-Mei|last2=Liang|first2=Yan-Li|last3=Cong|first3=Kun|last4=Chen|first4=Geng|last5=Zhao|first5=Xia|last6=Zhao|first6=Qi-Ming|last7=Zhang|first7=Jia-Jin|last8=Wang|first8=Xiao|last9=Dong|first9=Yang|date=2018|title=Identification and Characterization of Genes Involved in Benzylisoquinoline Alkaloid Biosynthesis in Coptis Species|journal=Front Plant Sci|volume=9|pages=731|doi=10.3389/fpls.2018.00731|pmid=29915609|pmc=5995273|doi-access=free}}