Magnoflorine

Magnoflorine
Names
IUPAC name
1,11-Dihydroxy-2,10-dimethoxy-6-methylaporphin-6-ium
Systematic IUPAC name
(6aS)-1,11-Dihydroxy-2,10-dimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-ium
Other names
Magnoflorine; Thalictrin; Escholin; Escholine; Thalictrine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.208.671 Edit this at Wikidata
KEGG
UNII
  • 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
    Key: YLRXAIKMLINXQY-ZDUSSCGKSA-O
  • C[N+]1(CCC2=CC(=C(C3=C2[C@@H]1CC4=C3C(=C(C=C4)OC)O)O)OC)C
Properties
C20H24NO4+
Molar mass 342.41 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(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, Sinomenium acutum, and Cissampelos pareira.  

It was identified among the verified anti-inflammatory components in an extract of Sinomenii caulis and has been proposed to have other potential physiological effects, such as sedative and anxiolytic, reduction of erythrocyte hemolysis, antifungal activity, improvement of LPS-induced acute lung injury, and protection against muscle atrophy. Furthermore, magnoflorine has been identified to be an inhibitor of NF-κB activation and to be an agonist at the β2 -adrenergic receptor.

(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.

References

  1. ↑ El-Kawi, M. A.; Slatkin, D. J.; Schiff, P. L.; Dasgupta, S; Chattopadhyay, S. K.; Ray, A. B. (1984). "Additional alkaloids of Pachygone ovata". J Nat Prod. 47 (3): 459–64. doi:10.1021/np50033a010. PMID 6481360.
  2. 1 2 de la Peña, June Bryan I.; Lee, Hye Lim; Yoon, Seo Young; Kim, Gun Hee; Lee, Yong Soo; Cheong, Jae Hoon (Oct 2013). "The involvement of magnoflorine in the sedative and anxiolytic effects of Sinomeni Caulis et Rhizoma in mice". J Nat Med. 67 (4): 814–21. doi:10.1007/s11418-013-0754-3. PMID 23456265. S2CID 14170353.
  3. ↑ Bala, M; Kumar, S; Pratap, K; Verma, P. K.; Padwad, Y; Singh, B (2019). "Bioactive isoquinoline alkaloids from Cissampelos pareira". Nat Prod Res. 33 (5): 622–627. doi:10.1080/14786419.2017.1402319. PMID 29126362. S2CID 9548987.
  4. ↑ Wang, Lan-Jin; Jiang, Zhen-Meng; Xiao, Ping-Ting; Sun, Jian-Bo; Bi, Zhi-Ming; Liu, E-Hu (2019). "Identification of anti-inflammatory components in Sinomenii Caulis based on spectrum-effect relationship and chemometric methods". J Pharm Biomed Anal. 167: 38–48. doi:10.1016/j.jpba.2019.01.047. PMID 30738242. S2CID 73436808.
  5. ↑ Sakumoto, Hitoshi; Yokota, Yumiko; Ishibashi, Gakushi; Maeda, Shouta; Hoshi, Chihiro; Takano, Haruyo; Kobayashi, Miki; Yahagi, Tadahiro; Ijiri, Soichiro (2015). "Sinomenine and magnoflorine, major constituents of Sinomeni Caulis et Rhizoma, show potent protective effects against membrane damage induced by lysophosphatidylcholine in rat erythrocytes". J Nat Med. 69 (3): 441–8. doi:10.1007/s11418-015-0907-7. PMID 25840917. S2CID 13871437.
  6. ↑ Kim, Jaegoo; Ha Quang Bao, Thinh; Shin, Yu-Kyong; Kim, Ki-Young (2018). "Antifungal activity of magnoflorine against Candida strains". World J Microbiol Biotechnol. 34 (11): 167. doi:10.1007/s11274-018-2549-x. PMID 30382403. S2CID 53195579.
  7. ↑ Guo, Shuai; Jiang, Kangfeng; Wu, Haichong; Yang, Chao; Yang, Yaping; Yang, Jing; Zhao, Gan; Deng, Ganzhen (2018). "Magnoflorine Ameliorates Lipopolysaccharide-Induced Acute Lung Injury via Suppressing NF-κB and MAPK Activation". Front. Pharmacol. 9: 982. doi:10.3389/fphar.2018.00982. PMC 6125611. PMID 30214410.
  8. ↑ Lee, Heyjin; Tuong, Le Thi; Jeong, Ji Hye; Lee, Sang-Jin; Bae, Gyu-Un; Ryu, Jae-Ha (2017). "Isoquinoline alkaloids from Coptis japonica stimulate the myoblast differentiation via p38 MAP-kinase and Akt signaling pathway". Bioorg Med Chem Lett. 27 (6): 1401–1404. doi:10.1016/j.bmcl.2017.02.003. PMID 28228365.
  9. ↑ Sun, Dan; Han, Yanqi; Wang, Weiya; Wang, Zengyong; Ma, Xiaoyao; Hou, Yuanyuan; Bai, Gang (2016). "Screening and identification of Caulis Sinomenii bioactive ingredients with dual-target NF-κB inhibition and β2-AR agonizing activities". Biomed Chromatogr. 30 (11): 1843–1853. doi:10.1002/bmc.3761. PMID 27187693.
  10. ↑ Morris, Jeremy S; Facchini, Peter J (2016). "Isolation and Characterization of Reticuline N-Methyltransferase Involved in Biosynthesis of the Aporphine Alkaloid Magnoflorine in Opium Poppy". J Biol Chem. 291 (45): 23416–23427. doi:10.1074/jbc.M116.750893. PMC 5095398. PMID 27634038.
  11. ↑ He, Si-Mei; Liang, Yan-Li; Cong, Kun; Chen, Geng; Zhao, Xia; Zhao, Qi-Ming; Zhang, Jia-Jin; Wang, Xiao; Dong, Yang (2018). "Identification and Characterization of Genes Involved in Benzylisoquinoline Alkaloid Biosynthesis in Coptis Species". Front Plant Sci. 9: 731. doi:10.3389/fpls.2018.00731. PMC 5995273. PMID 29915609.