ContaminantDB: Lycorine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-08-29 05:00:45 UTC

Update Date

2016-11-09 01:09:02 UTC

Accession Number

CHEM003024

Identification

Common Name

Lycorine

Class

Small Molecule

Description

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. Symptoms of lycorine toxicity are vomiting, diarrhea, and convulsions. Lycorine, definition at mercksource.com Regardless, it is sometimes used medicinally, a reason why some groups may harvest the very popular Clivia miniata.

Contaminant Sources

T3DB toxins

Contaminant Type

Amine
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(-)-Lycorine	ChEBI
Amarylline	ChEBI
Galanthidine	ChEBI
Licorine	ChEBI
Narcissine	ChEBI
2,4,5,7,12b,12C-Hexahydro-1H-(1,3)dioxolo- (4,5-J)pyrrolo(3,2,1-de)phenanthridine-1,2-diol	MeSH
Lycorine hydrochloride, (1alpha,2beta)-isomer	MeSH
3,3a-Didehydrolycoran-1alpha,2beta-diol	PhytoBank
3,3a-Didehydrolycoran-1α,2β-diol	PhytoBank
3,4-Didehydro-11,12-[methylenebis(oxy)]galanthan-1alpha,2beta-diol	PhytoBank
3,4-Didehydro-11,12-[methylenebis(oxy)]galanthan-1α,2β-diol	PhytoBank
Narcissin	PhytoBank

Chemical Formula

C₁₆H₁₇NO₄

Average Molecular Mass

287.311 g/mol

Monoisotopic Mass

287.116 g/mol

CAS Registry Number

476-28-8

IUPAC Name

(1S,17S,18S,19S)-5,7-dioxa-12-azapentacyclo[10.6.1.0^{2,10}.0^{4,8}.0^{15,19}]nonadeca-2,4(8),9,15-tetraene-17,18-diol

Traditional Name

(1S,17S,18S,19S)-5,7-dioxa-12-azapentacyclo[10.6.1.0^{2,10}.0^{4,8}.0^{15,19}]nonadeca-2,4(8),9,15-tetraene-17,18-diol

SMILES

[H][C@@]12N3CCC1=C[C@]([H])(O)[C@@]([H])(O)[C@@]2([H])C1=CC2=C(OCO2)C=C1C3

InChI Identifier

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

InChI Key

XGVJWXAYKUHDOO-DANNLKNASA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as lycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the lycorine skeleton, made up of a pyrrolo[d,e]phenanthridine ring system.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Lycorine-type amaryllidaceae alkaloids

Direct Parent

Lycorine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Lycorine skeleton
Benzoquinoline
Phenanthridine
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Indole or derivatives
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
1,2-diol
Organoheterocyclic compound
Azacycle
Oxacycle
Acetal
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Amine
Alcohol
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indolizidine alkaloid (CHEBI:6601 )
Isoquinoline alkaloids (C08532 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Endoplasmic reticulum membrane
Extracellular
Mitochondrion
Ribosome

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Apoptosis	Not Available	map04210
Cell cycle	Not Available	map04110

Applications

Not Available

Biological Roles

Chemical Roles

protein synthesis inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	7.43 g/L	ALOGPS
logP	0.01	ALOGPS
logP	0.16	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	13.46	ChemAxon
pKa (Strongest Basic)	7.82	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.16 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	76.18 m³·mol⁻¹	ChemAxon
Polarizability	30.04 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-541d9e5ebce4884ee6f2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-0090000000-aab8ce149630f65d17dc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fkc-1190000000-c75a15b3ca7042751b59	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-b01b02205eecad1a2821	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-ca3318ca7ae80ee9797e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0229-1190000000-73ea3912a735adeaa744	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Lycorine is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Metabolism

Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

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). Lycorine, definition at mercksource.com Regardless, it is sometimes used medicinally, a reason why some groups may harvest the very popular Clivia miniata.

Minimum Risk Level

Not Available

Health Effects

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Symptoms

Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.

Treatment

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID