Protopine
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| 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
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| 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)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.004.546 |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C20H19NO5 | |
| Molar mass | 353.369 g/mol |
| Appearance | white 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).
Infobox references
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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]
It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an analgesic.[5][6]
Biosynthesis
Protopine is derived in the plants such as the opium poppy, Papaver somniferum, 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.[7]
The final step is oxidation by the enzyme methyltetrahydroprotoberberine 14-monooxygenase:[8][9]
-cis-N-methylstylopine.svg.png)
Metabolism
The enzyme protopine 6-monooxygenase converts protopine into dihydrosanguinarine.[8][10] NADP+ and water are the by-products.
The enzyme uses reduced nicotinamide adenine dinucleotide phosphate (NADPH), and oxygen, with the initial product being 6-hydroxyprotopine, which spontaneously forms dihydrosanguinarine, found in plants such as Sanguinaria canadensis.[11]
See also
References
- ^ The Merck Index (9 ed.). New Jersey: Merck & Co. 1976. p. 1023.
- ^ The Free Dictionary: Protopine
- ^ 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.
- ^ Vrba, Jiri; Vrublova, Eva; Modriansky, Martin; Ulrichova, Jitka (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.
- ^ 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.
- ^ Protopine at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
- ^ 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.
- ^ a b Tian, Ya; Kong, Lingzhe; Li, Qi; Wang, Yifan; Wang, Yongmiao; An, Zhoujie; Ma, Yuwei; Tian, Lixia; Duan, Baozhong; Sun, Wei; Gao, Ranran; Chen, Shilin; Xu, Zhichao (2024). "Structural diversity, evolutionary origin, and metabolic engineering of plant specialized benzylisoquinoline alkaloids". Natural Product Reports. 41 (11): 1787–1810. doi:10.1039/d4np00029c. PMID 39360417.
- ^ Rueffer M, Zenk MH (1987). "Enzymatic formation of protopines by a microsomal cytochrome-P-450 system of Corydalis vaginans". Tetrahedron Lett. 28 (44): 5307–5310. doi:10.1016/S0040-4039(00)96715-7.
- ^ Tanahashi, Takao; Zenk, Meinhart H. (1990). "Elicitor induction and characterization of microsomal protopine-6-hydroxylase, the central enzyme in benzophenanthridine alkaloid biosynthesis". Phytochemistry. 29 (4): 1113–1122. doi:10.1016/0031-9422(90)85414-B.
- ^ Ignatov, Atanas; Clark, W.Gregg; Cline, Steven D.; Psenak, Mikulas; Krueger, Robert J.; Coscia, Carmine J. (1996). "Elicitation of dihydrobenzophenanthridine oxidase in Sanguinaria canadensis cell cultures". Phytochemistry. 43 (6): 1141–1144. doi:10.1016/S0031-9422(96)00540-7. PMID 8987906.