{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 462094850 | ImageFile=Lycorine.svg | ImageClass = skin-invert-image | ImageSize=200px | IUPACName=3,12-Didehydro-2′''H''-[1,3]dioxolo[4′,5′:9,10]galanthan-1α,2β-diol | SystematicName=(1''S'',2''S'',3a<sup>1</sup>''S'',12b''S'')-2,3a<sup>1</sup>,4,5,7,12b-Hexahydro-1''H'',10''H''-[1,3]dioxolo[4,5-''j'']pyrrolo[3,2,1-''de'']phenanthridine-1,2-diol | OtherNames=Galanthidine, Amarylline, Narcissine, Licorine, Belamarine |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 65312 | 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 | InChIKey = XGVJWXAYKUHDOO-DANNLKNABD | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = XGVJWXAYKUHDOO-DANNLKNASA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo=476-28-8 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = I9Q105R5BU | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 400092 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C08532 | PubChem=72378 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 6601 | SMILES = O1c2c(OC1)cc3c(c2)[C@H]4[C@@H]/5N(C3)CCC\5=C/[C@H](O)[C@H]4O }} |Section2={{Chembox Properties | C=16 | H=17 | N=1 | O=4 | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= }} |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }} }}

'''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.<ref>{{Cite web|url=http://www.t3db.ca/toxins/T3D4064|title=T3DB: Lycorine|website=www.t3db.ca|access-date=2018-11-12}}</ref> 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.<ref>{{cite journal|last1=Jahn|first1=Sandra|last2=Seiwert|first2=Bettina|last3=Kretzing|first3=Sascha|last4=Abraham|first4=Getu|last5=Regenthal|first5=Ralf|last6=Karst|first6=Uwe|title=Metabolic studies of the Amaryllidaceous alkaloids galantamine and lycorine based on electrochemical simulation in addition to in vivo and in vitro models|journal=Analytica Chimica Acta|volume=756|date=2012|issue=756|pages=60–72|url=http://www.elsevier.com/locate/aca|access-date=25 April 2017|doi=10.1016/j.aca.2012.10.042|pmid=23176740|bibcode=2012AcAC..756...60J |url-access=subscription}}</ref>

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.''<ref>{{cite journal|last1=Berkov|first1=Strahil|last2=Martinez-Frances|first2=Vanessa|last3=Bastida|first3=Jaume|last4=Codina|first4=Carles|last5=Rios|first5=Sequndo|title=Evolution of alkaloid biosynthesis in the genus Narcissus|journal=Phytochemistry|volume=99|date=2014|issue=99|pages=95–106|url=https://www.journals.elsevier.com/phytochemistry|doi=10.1016/j.phytochem.2013.11.002|pmid=24461780|bibcode=2014PChem..99...95B |url-access=subscription}}</ref>

==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.<ref>{{cite journal|last1=Kretzing|first1=Sascha|last2=Abraham|first2=Getu|last3=Seiwert|first3=Bettina|last4=Ungemach|first4=Fritz Rupert|last5=Krugel|first5=Ute|last6=Regenthal|first6=Ralf|title=Dose-dependent emetic effects of the Amaryllidaceous alkaloid lycorine in beagle dogs|journal=Toxicon|volume=57|date=2011|issue=57|pages=117–124|url=https://www.journals.elsevier.com/toxicon|access-date=25 April 2017|doi=10.1016/j.toxicon.2010.10.012|pmid=21055413|bibcode=2011Txcn...57..117K |url-access=subscription}}</ref>

Lycorine inhibits protein synthesis,<ref>{{cite journal |vauthors=Vrijsen R, Vanden Berghe DA, Vlietinck AJ, Boeyé A |title=Lycorine: a eukaryotic termination inhibitor? |journal=J. Biol. Chem. |volume=261 |issue=2 |pages=505–7 |year=1986 |doi=10.1016/S0021-9258(17)36118-5 |pmid=3001065 |doi-access=free }}</ref> 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.<ref>{{cite journal |vauthors=Garuccio I, Arrigoni O |title=[Various sensitivities of yeasts to lycorine] |language=it |journal=Boll. Soc. Ital. Biol. Sper. |volume=65 |issue=6 |pages=501–8 |year=1989 |pmid=2611011 }}</ref>

It is known that lycorine weakly inhibits acetylcholinesterase (AChE) and ascorbic acid biosynthesis.<ref>{{cite journal|last1=Jahn|first1=Sandra|last2=Seiwert|first2=Bettina|last3=Kretzing|first3=Sascha|last4=Abraham|first4=Getu|last5=Regenthal|first5=Ralf|last6=Karst|first6=Uwe|title=Metabolic studies of the Amaryllidaceous alkaloids galantamine and lycorine based on electrochemical simulation in addition to in vivo and in vitro models|journal=Analytica Chimica Acta|volume=756|date=2012|issue=756|pages=60–72|url=http://www.elsevier.com/locate/aca|access-date=25 April 2017|doi=10.1016/j.aca.2012.10.042|pmid=23176740|bibcode=2012AcAC..756...60J |url-access=subscription}}</ref> 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.<ref>{{cite journal|last1=Elisha|first1=I.L.|last2=Elgorashi|first2=E.E.|last3=Hussein|first3=A.A.|last4=Duncan|first4=G.|last5=Eloff|first5=J.N.|title=Acetlycholinesterase inhibitory effects of the bulb of Ammocharis coranica (Amaryllidaceae) and its active constituent lycorine|journal=South African Journal of Botany|date=2013|volume=85|issue=85|pages=44–47|doi=10.1016/j.sajb.2012.11.008|doi-access=free|bibcode=2013SAJB...85...44E }}</ref>

Lycorine is a potent inhibitor of multiple human cancer cell lines.<ref>{{cite journal|last1=Wang|first1=Peng|last2=Yuan|first2=Hui-Hui|last3=Zhang|first3=Xue|last4=Li|first4=Yun-Ping|last5=Shang|first5=Lu-Qing|last6=Yin|first6=Zheng|title=Novel Lycorine Derivatives as Anticancer Agents: Synthesis and In Vitro Biological Evaluation|journal=Molecules|volume=19|date=21 February 2014|issue=2|pages=2469–2480|doi=10.3390/molecules19022469|pmid=24566315|pmc=6271160|doi-access=free}}</ref><ref>{{cite journal|last1=Cao|first1=Zhifei|last2=Yu|first2=Di|last3=Fu|first3=Shilong|last4=Zhang|first4=Gaochuan|last5=Pan|first5=Yanyan|last6=Bao|first6=Meimei|last7=Tu|first7=Jian|last8=Shang|first8=Bingxue|last9=Guo|first9=Pengda|last10=Yang|first10=Ping|last11=Zhou|first11=Quansheng|title=Lycorine hydrochloride selectively inhibits human ovarian cancer cell proliferation and tumor neovascularization with very low toxicity|journal=Toxicology Letters|volume=218|date=2013|issue=2|pages=174–185|url=https://www.journals.elsevier.com/toxicology-letters|access-date=25 April 2017|doi=10.1016/j.toxlet.2013.01.018|pmid=23376478|url-access=subscription}}</ref>

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.<ref>[https://news.bbc.co.uk/1/hi/england/suffolk/8031344.stm Pupils ill after bulb put in soup], ''BBC News'', 3 May 2009</ref>

In a study on beagle dogs, the first sign of nausea was observed at as little of a dose of 0.5&nbsp;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&nbsp;mg/kg and lasted no longer than 2.5 hours after administration.<ref>{{cite journal|last1=Kretzing|first1=Sascha|last2=Abraham|first2=Getu|last3=Seiwert|first3=Bettina|last4=Ungemach|first4=Fritz Rupert|last5=Krugel|first5=Ute|last6=Regenthal|first6=Ralf|title=Dose-dependent emetic effects of the Amaryllidaceous alkaloid lycorine in beagle dogs|journal=Toxicon|volume=57|date=2011|issue=57|pages=117–124|url=https://www.journals.elsevier.com/toxicon|access-date=25 April 2017|doi=10.1016/j.toxicon.2010.10.012|pmid=21055413|bibcode=2011Txcn...57..117K |url-access=subscription}}</ref>

Symptoms of lycorine exposure include nausea,<ref>{{cite journal|last1=Kretzing|first1=Sascha|last2=Abraham|first2=Getu|last3=Seiwert|first3=Bettina|last4=Ungemach|first4=Fritz Rupert|last5=Krugel|first5=Ute|last6=Regenthal|first6=Ralf|title=Dose-dependent emetic effects of the Amaryllidaceous alkaloid lycorine in beagle dogs|journal=Toxicon|volume=57|date=2011|issue=57|pages=117–124|url=https://www.journals.elsevier.com/toxicon|access-date=25 April 2017|doi=10.1016/j.toxicon.2010.10.012|pmid=21055413|bibcode=2011Txcn...57..117K |url-access=subscription}}</ref> vomiting with diarrhea, and convulsions.<ref>[http://www.mercksource.com/pp/us/cns/cns_hl_dorlands.jspzQzpgzEzzSzppdocszSzuszSzcommonzSzdorlandszSzdorlandzSzdmd_l_16zPzhtm Lycorine], definition at mercksource.com</ref>

== References == <references/>

== External links == * {{Cite journal| year = 1962| pages = 4951–4956| doi = 10.1021/ja00883a064| last2 = Joule| last3 = Loeffler| first1 = R. K.| volume = 84| first2 = J. A.| last1 = Hill| first3 = L. J.| journal = Journal of the American Chemical Society| title = Stereoselective Syntheses of d,l-α- and β-Lycoranes| issue = 24| bibcode = 1962JAChS..84.4951H}} * {{cite journal | doi = 10.1021/ja00086a060 | url = http://www.ch.ic.ac.uk/spivey/publicationpdfs/jacs19941163139.pdf | title = Suprafaciality of Thermal N-4-Alkenylhydroxylamine Cyclizations: Syntheses of (±)-α-Lycorane and (+)-Tianthine | author1 = Wolfgang Oppolzer | author2 = Alan C. Spivey | author3 = Christian G. Bochet | name-list-style = amp | journal = J. Am. Chem. Soc. | year = 1994 | volume = 116 | pages = 3139–3140 | issue = 7 | access-date = 2009-11-04 | archive-url = https://web.archive.org/web/20110614104657/http://www.ch.ic.ac.uk/spivey/publicationpdfs/jacs19941163139.pdf | archive-date = 2011-06-14 | url-status = dead }}

{{Acetylcholine metabolism and transport modulators}}

Category:Quinoline alkaloids Category:Diols Category:Phenanthridines Category:Plant toxins Category:Acetylcholinesterase inhibitors Category:Neurotoxins Category:Protein synthesis inhibitors Category:Heterocyclic compounds with 5 rings Category:Methylenedioxyphenethylamines Category:Tetrahydroisoquinoline alkaloids Category:Experimental cancer drugs