Magnoflorine Explained

(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,[1] Sinomenium acutum,[2] and Cissampelos pareira.[3]  

It was identified among the verified anti-inflammatory components in an extract of Sinomenii caulis[4] and has been proposed to have other potential physiological effects, such as sedative and anxiolytic, reduction of erythrocyte hemolysis,[5] antifungal activity,[6] improvement of LPS-induced acute lung injury,[7] and protection against muscle atrophy.[8] Furthermore, magnoflorine has been identified to be an inhibitor of NF-κB activation and to be an agonist at the β2 -adrenergic receptor.[9]

(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.[10] [11]

Notes and 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. 10.1021/np50033a010. 6481360 .
  2. Oct 2013. The involvement of magnoflorine in the sedative and anxiolytic effects of Sinomeni Caulis et Rhizoma in mice. J Nat Med. 67. 814–21. 10.1007/s11418-013-0754-3. 23456265. de la Peña. June Bryan I.. Lee. Hye Lim. Yoon. Seo Young. Kim. Gun Hee. Lee. Yong Soo. Cheong. Jae Hoon. 4. 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. 10.1080/14786419.2017.1402319. 29126362. 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. 10.1016/j.jpba.2019.01.047. 30738242. 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. 10.1007/s11418-015-0907-7. 25840917. 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. 10.1007/s11274-018-2549-x. 30382403. 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. 10.3389/fphar.2018.00982. 30214410. 6125611. free.
  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. 10.1016/j.bmcl.2017.02.003. 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. 10.1002/bmc.3761. 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. 10.1074/jbc.M116.750893. 27634038. 5095398. free.
  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. 10.3389/fpls.2018.00731. 29915609. 5995273. free.

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