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Protopine
Topic: Chemistry
From HandWiki - Reading time: 4 min
Protopine is an alkaloid occurring in opium poppy,[1] Corydalis tubers[2] and other plants of the family papaveraceae, like Fumaria officinalis.[3]
It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an analgesic.[4][5]
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.[6]
The final step is oxidation by the enzyme methyltetrahydroprotoberberine 14-monooxygenase:[7][8]
Metabolism
The enzyme protopine 6-monooxygenase converts protopine into dihydrosanguinarine.[7][9] 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.[10]
See also
- Cryptopine
- Bürgi-Dunitz angle
References
- ↑ 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 US 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 et al. (2015). "Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants". BMC Plant Biology 15: 227. doi:10.1186/s12870-015-0596-0. PMID 26384972. PMC 4575454. http://openlib.tugraz.at/download.php?id=564f2fa60a35b&location=browse.
- ↑ 7.0 7.1 Tian, Ya; Kong, Lingzhe; Li, Qi; Wang, Yifan; Wang, Yongmiao; An, Zhoujie; Ma, Yuwei; Tian, Lixia et al. (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.
- ↑ "Enzymatic formation of protopines by a microsomal cytochrome-P-450 system of Corydalis vaginans". Tetrahedron Lett. 28 (44): 5307–5310. 1987. doi:10.1016/S0040-4039(00)96715-7. http://nbn-resolving.de/urn:nbn:de:bvb:19-epub-3622-0.
- ↑ 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.
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