Protopine

Last updated
Protopine [1]
Protopine structure.svg
Protopine-from-xtal-Mercury-3D-balls.png
Names
IUPAC name
7-Methyl-2′H,2′′H-7,13a-secobis([1,3]dioxolo)[4′,5′:2,3;4′′,5′′:9,10]berbin-13a-one
Systematic IUPAC name
5-Methyl-4,6,7,14-tetrahydro-2H,10H-bis([1,3]benzodioxolo)[4,5-c:5′,6′-g]azecin-13(5H)-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.546 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-999-6
KEGG
PubChem CID
UNII
  • InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3 X mark.svgN
    Key: GPTFURBXHJWNHR-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3
    Key: GPTFURBXHJWNHR-UHFFFAOYAW
  • c15cc3OCOc3cc5CCN(C)Cc2c(CC1=O)ccc4c2OCO4
Properties
C20H19NO5
Molar mass 353.369 g/mol
Appearancewhite crystals
Density 1.399 g/cm3
Melting point 208 °C (406 °F; 481 K)
practically insoluble
Solubility in chloroform 1:15
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Protopine is an alkaloid occurring in opium poppy, [2] Corydalis tubers [3] and other plants of the family papaveraceae, like Fumaria officinalis . [4] Protopine is metabolically derived from the benzylisoquinoline alkaloid (S)-Reticuline through a progressive series of five enzymatic transformations: 1) berberine bridge enzyme to (S)-Scoulerine; 2) (S)-cheilanthifoline synthase/CYP719A25 to (S)-Cheilanthifoline; 3)  (S)-stylopine synthase/CYP719A20 to (S)-Stylopine; 4) (S)-tetrahydroprotoberberine N-methyltransferase to (S)-cis-N-Methylstylopine; and ultimately, 5) N-methylstylopine hydroxylase to protopine. [5]

It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an analgesic. [6] [7]

See also

References

  1. ↑ The Merck Index (9 ed.). New Jersey: Merck & Co. 1976. p. 1023.
  2. ↑ The Free Dictionary: Protopine
  3. ↑ Jiang, B; Cao, K; Wang, R (2004). "Inhibitory effect of protopine on K(ATP) channel subunits expressed in HEK-293 cells". European Journal of Pharmacology. 506 (2): 93–100. doi:10.1016/j.ejphar.2004.11.004. PMID   15588728.
  4. ↑ Vrba, J.; Vrublova, E.; Modriansky, M.; Ulrichova, J. (2011). "Protopine and allocryptopine increase mRNA levels of cytochromes P450 1A in human hepatocytes and HepG2 cells independently of AhR". Toxicology Letters. 203 (2): 135–141. doi:10.1016/j.toxlet.2011.03.015. PMID   21419197.
  5. ↑ Hagel, Jillian M; Morris, Jeremy S; Lee, Eun-Jeong; Desgagne-Penix, Isabel; Bross, Crystal D; Chang, Limei; Chen, Xue; Farrow, Scott C; Zhang, Ye (2015). "Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants". BMC Plant Biology. 15: 227. doi: 10.1186/s12870-015-0596-0 . PMC   4575454 . PMID   26384972.
  6. ↑ Saeed, SA; Gilani, AH; Majoo, RU; Shah, BH (1997). "Anti-thrombotic and anti-inflammatory activities of protopine". Pharmacological Research. 36 (1): 1–7. doi:10.1006/phrs.1997.0195. PMID   9368908.
  7. ↑ Protopine at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
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