Protopine

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]

## Contents

* 1 Biosynthesis
* 2 Metabolism
* 3 See also
* 4 References

## 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]

Template:Chemrxn

## Metabolism

The enzyme protopine 6-monooxygenase converts protopine into dihydrosanguinarine.[7][9] NADP+ and water are the by-products.

Template:Chemrxn

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

1. ↑ The Free Dictionary: Protopine
2. ↑ 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.
3. ↑ 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.
4. ↑ 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.
5. ↑ Protopine at the US National Library of Medicine Medical Subject Headings (MeSH)
6. ↑ 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. ↑ 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.
8. ↑ "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.
9. ↑ 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.
10. ↑ 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.

* v
* t
* e

Opium components

Alkaloids|

* 16-Hydroxythebaine
* Berberine
* Canadine
* Codamine
* Coptisine
* Coreximine
* Cycloartenol
* Cycloartenone
* Cyclolaudenol
* Dehydroreticuline
* Dihydrosanguinarine
* Glaucine
* Isoboldine
* Isocorypalmine
* Laudanidine
* Magnoflorine
* Narceine
* Narceinone
* Norlaudanosoline
* Norsanguinarine
* Oripavine
* Oxysanguinarine
* Palaudine
* Papaverrubine B (O-methyl-porphyroxine)
* Papaverrubine C (epiporphyroxine)
* Reticuline
* Salutaridine (sinoacutine)
* Sanguinarine
* Scoulerine
* Somniferine
* Stepholidine

Morphine group
(Phenanthrenes. Includes opioids)|

* Codeine
* Morphine
* Narcotoline
* Neopine
* Perparin
* Papaverrubine D (porphyroxine)
* Pseudocodeine
* Pseudomorphine
* Thebaine

Isoquinolines|

* Cotarnine
* Eupaverine
* Hydrocotarnine
* Laudanosine
* Laudanine
* Noscapine (narcotine)
* Papaverine
* Papaveraldine
* Xanthaline

Protopine group|

* α-Allocryptopine
* α-Fagarine
* Corycavamine
* Corycavine
* Cryptopine
* Protopine

Tetrahydroprotoberberine group|

* Corydaline
* Corybulbine
* Isocorybulbine
* Capaurine

Aporphine group|

* Dicentrine
* Glaucine
* Corytuberine
* Cularine
* Corydine
* Isocorydine
* Bulbocapnine

Phtalide-isoquinolines|

* Adulmine
* Bicuculline
* Bicucine
* Corlumine

α-Naphthaphenanthridines|

* Chelidonine
* β-Homochelidonoine
* Chelerythrine
* Sanguinarine

Other components|

* Meconic acid

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