Lycorine

Lycorine
Names
IUPAC name
3,12-Didehydro-2′H-[1,3]dioxolo[4′,5′:9,10]galanthan-1α,2β-diol
Systematic IUPAC name
(1S,2S,3a1S,12bS)-2,3a1,4,5,7,12b-Hexahydro-1H,10H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diol
Other names
Galanthidine, Amarylline, Narcissine, Licorine, Belamarine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.822
KEGG
UNII
  • InChI=1S/C16H17NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h3-5,11,14-16,18-19H,1-2,6-7H2/t11-,14-,15+,16+/m0/s1 checkY
    Key: XGVJWXAYKUHDOO-DANNLKNASA-N checkY
  • InChI=1/C16H17NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h3-5,11,14-16,18-19H,1-2,6-7H2/t11-,14-,15+,16+/m0/s1
    Key: XGVJWXAYKUHDOO-DANNLKNABD
  • O1c2c(OC1)cc3c(c2)[C@H]4[C@@H]/5N(C3)CCC\5=C/[C@H](O)[C@H]4O
Properties
C16H17NO4
Molar mass 287.315 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Lycorine is a toxic crystalline alkaloid found in various Amaryllidaceae species, such as the cultivated bush lily (Clivia miniata), surprise lilies (Lycoris), and daffodils (Narcissus). It may be highly poisonous, or even lethal, when ingested in certain quantities.[1] Regardless, it is sometimes used as a component in traditional medicines.

Source

Lycorine is found in different species of Amaryllidaceae which include flowers and bulbs of daffodil, snowdrop (Galanthus) or spider lily (Lycoris). Lycorine is the most frequent alkaloid of Amaryllidaceae.[2]

A 2014 research paper suggested that the earliest diversification of the Amaryllidaceae likely occurred in North Africa and the Iberian Peninsula. Furthermore, the study concluded that the biosynthetic pathway responsible for lycorine production is the oldest among the various toxin synthesis pathways found within the Amaryllidaceae.[3]

Mechanism of action

There is currently very little known about the mechanism of action of lycorine, although there have been some tentative hypotheses advanced concerning the metabolism of the alkaloid, based on experiments carried out upon beagle dogs.[4]

Lycorine inhibits protein synthesis,[5] and may inhibit ascorbic acid biosynthesis, although studies on the latter are controversial and inconclusive. Presently, it serves some interest in the study of certain yeasts, the principal organism on which lycorine is tested.[6]

It is known that lycorine weakly inhibits acetylcholinesterase (AChE) and ascorbic acid biosynthesis.[7] The IC50 of lycorine was found to vary between the different species it can be found in, but a common deduction from the experiments on lycorine was that it had some effect on inhibiting AChE.[8]

Lycorine is a potent inhibitor of multiple human cancer cell lines.[9][10]

Poisoning by lycorine most often occurs through the ingestion of daffodil bulbs. Daffodil bulbs are sometimes confused with onions or other Allium species, leading to accidental poisoning.[11]

In a study on beagle dogs, the first sign of nausea was observed at as little of a dose of 0.5 mg/kg and occurred within a 2.5 hour span. The effective dose to induce emesis in the dogs was seen to be 2.0 mg/kg and lasted no longer than 2.5 hours after administration.[12]

Symptoms of lycorine exposure include nausea,[13] vomiting with diarrhea, and convulsions.[14]

References

  1. ^ "T3DB: Lycorine". www.t3db.ca. Retrieved 2018-11-12.
  2. ^ Jahn, Sandra; Seiwert, Bettina; Kretzing, Sascha; Abraham, Getu; Regenthal, Ralf; Karst, Uwe (2012). "Metabolic studies of the Amaryllidaceous alkaloids galantamine and lycorine based on electrochemical simulation in addition to in vivo and in vitro models". Analytica Chimica Acta. 756 (756): 60–72. Bibcode:2012AcAC..756...60J. doi:10.1016/j.aca.2012.10.042. PMID 23176740. Retrieved 25 April 2017.
  3. ^ Berkov, Strahil; Martinez-Frances, Vanessa; Bastida, Jaume; Codina, Carles; Rios, Sequndo (2014). "Evolution of alkaloid biosynthesis in the genus Narcissus". Phytochemistry. 99 (99): 95–106. Bibcode:2014PChem..99...95B. doi:10.1016/j.phytochem.2013.11.002. PMID 24461780.
  4. ^ Kretzing, Sascha; Abraham, Getu; Seiwert, Bettina; Ungemach, Fritz Rupert; Krugel, Ute; Regenthal, Ralf (2011). "Dose-dependent emetic effects of the Amaryllidaceous alkaloid lycorine in beagle dogs". Toxicon. 57 (57): 117–124. Bibcode:2011Txcn...57..117K. doi:10.1016/j.toxicon.2010.10.012. PMID 21055413. Retrieved 25 April 2017.
  5. ^ Vrijsen R, Vanden Berghe DA, Vlietinck AJ, Boeyé A (1986). "Lycorine: a eukaryotic termination inhibitor?". J. Biol. Chem. 261 (2): 505–7. doi:10.1016/S0021-9258(17)36118-5. PMID 3001065.
  6. ^ Garuccio I, Arrigoni O (1989). "[Various sensitivities of yeasts to lycorine]". Boll. Soc. Ital. Biol. Sper. (in Italian). 65 (6): 501–8. PMID 2611011.
  7. ^ Jahn, Sandra; Seiwert, Bettina; Kretzing, Sascha; Abraham, Getu; Regenthal, Ralf; Karst, Uwe (2012). "Metabolic studies of the Amaryllidaceous alkaloids galantamine and lycorine based on electrochemical simulation in addition to in vivo and in vitro models". Analytica Chimica Acta. 756 (756): 60–72. Bibcode:2012AcAC..756...60J. doi:10.1016/j.aca.2012.10.042. PMID 23176740. Retrieved 25 April 2017.
  8. ^ Elisha, I.L.; Elgorashi, E.E.; Hussein, A.A.; Duncan, G.; Eloff, J.N. (2013). "Acetlycholinesterase inhibitory effects of the bulb of Ammocharis coranica (Amaryllidaceae) and its active constituent lycorine". South African Journal of Botany. 85 (85): 44–47. Bibcode:2013SAJB...85...44E. doi:10.1016/j.sajb.2012.11.008.
  9. ^ Wang, Peng; Yuan, Hui-Hui; Zhang, Xue; Li, Yun-Ping; Shang, Lu-Qing; Yin, Zheng (21 February 2014). "Novel Lycorine Derivatives as Anticancer Agents: Synthesis and In Vitro Biological Evaluation". Molecules. 19 (2): 2469–2480. doi:10.3390/molecules19022469. PMC 6271160. PMID 24566315.
  10. ^ Cao, Zhifei; Yu, Di; Fu, Shilong; Zhang, Gaochuan; Pan, Yanyan; Bao, Meimei; Tu, Jian; Shang, Bingxue; Guo, Pengda; Yang, Ping; Zhou, Quansheng (2013). "Lycorine hydrochloride selectively inhibits human ovarian cancer cell proliferation and tumor neovascularization with very low toxicity". Toxicology Letters. 218 (2): 174–185. doi:10.1016/j.toxlet.2013.01.018. PMID 23376478. Retrieved 25 April 2017.
  11. ^ Pupils ill after bulb put in soup, BBC News, 3 May 2009
  12. ^ Kretzing, Sascha; Abraham, Getu; Seiwert, Bettina; Ungemach, Fritz Rupert; Krugel, Ute; Regenthal, Ralf (2011). "Dose-dependent emetic effects of the Amaryllidaceous alkaloid lycorine in beagle dogs". Toxicon. 57 (57): 117–124. Bibcode:2011Txcn...57..117K. doi:10.1016/j.toxicon.2010.10.012. PMID 21055413. Retrieved 25 April 2017.
  13. ^ Kretzing, Sascha; Abraham, Getu; Seiwert, Bettina; Ungemach, Fritz Rupert; Krugel, Ute; Regenthal, Ralf (2011). "Dose-dependent emetic effects of the Amaryllidaceous alkaloid lycorine in beagle dogs". Toxicon. 57 (57): 117–124. Bibcode:2011Txcn...57..117K. doi:10.1016/j.toxicon.2010.10.012. PMID 21055413. Retrieved 25 April 2017.
  14. ^ Lycorine, definition at mercksource.com
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