U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H17NO4
Molecular Weight 287.3105
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LYCORINE

SMILES

O[C@H]1C=C2CCN3CC4=CC5=C(OCO5)C=C4[C@@H]([C@@H]23)[C@@H]1O

InChI

InChIKey=XGVJWXAYKUHDOO-DANNLKNASA-N
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

HIDE SMILES / InChI
Molecular Formula C16H17NO4
Molecular Weight 287.3105
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Lycorine is a natural pyrrolo[de]phenanthridine ring-type alkaloid extracted from Amaryllidaceae. It has been reported to exhibit a wide range of physiological effects, including anti-viral, anti-malarial, anti-cancer and anti-inflammatory. Although a defined target or mechanism of action of lycorine is still unknown, it is a candidate anti-inflammatory and anti-cancer drug.

CNS Activity

CNS Penetrant
2588
Curator's Comment: Lycorine was shown to cross the blood-brain barrier in mice. It is potentially CNS-active.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Acetylcholinesterase
209
Target ID: P22303|||Q53F46
Gene ID: 43.0
Gene Symbol: ACHE
Target Organism: Homo sapiens (Human)
Inhibitor
8504
 213.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Lycorine hydrochloride selectively inhibits human ovarian cancer cell proliferation and tumor neovascularization with very low toxicity.
2013-04-12
Lycorine inhibits lipopolysaccharide-induced iNOS and COX-2 up-regulation in RAW264.7 cells through suppressing P38 and STATs activation and increases the survival rate of mice after LPS challenge.
2012-01
In vivo assessment of antiemetic drugs and mechanism of lycorine-induced nausea and emesis.
2011-12
[Study on the chemical constituents from the bulbs of Zephyranthes candida].
2010-11
Lycorine sensitizes CD40 ligand-protected chronic lymphocytic leukemia cells to bezafibrate- and medroxyprogesterone acetate-induced apoptosis but dasatanib does not overcome reported CD40-mediated drug resistance.
2010-11
Structure-activity studies on acetylcholinesterase inhibition in the lycorine series of Amaryllidaceae alkaloids.
2010-09-01
A survey of phytotoxic microbial and plant metabolites as potential natural products for pest management.
2010-09
Alkaloid accumulation in different parts and ages of Lycoris chinensis.
2010-08-27
Up-regulation of p21 and TNF-alpha is mediated in lycorine-induced death of HL-60 cells.
2010-08-04
Cytochrome P450 3A4 inhibitory activity studies within the lycorine series of alkaloids.
2010-08
Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells.
2010-07-23
Synthesis and antiplasmodial activity of lycorine derivatives.
2010-07-01
HPLC - DAD analysis of lycorine in Amaryllidaceae species.
2010-06
Trichomonas vaginalis nucleoside triphosphate diphosphohydrolase and ecto-5'-nucleotidase activities are inhibited by lycorine and candimine.
2010-06
Total synthesis of the lycorenine-type amaryllidaceae alkaloid (+/-)-clivonine via a biomimetic ring-switch from a lycorine-type progenitor.
2010-04-14
Pancratistatin induces apoptosis in clinical leukemia samples with minimal effect on non-cancerous peripheral blood mononuclear cells.
2010-03-06
Quantitative determination of Amaryllidaceae alkaloids from Galanthus reginae-olgae subsp. vernalis and in vitro activities relevant for neurodegenerative diseases.
2010-01
Lycorine and its derivatives for anticancer drug design.
2010-01
The first phytochemical report of Galanthus transcaucasicus Fomin.
2010
Galanthamine production by Leucojum aestivum cultures in vitro.
2010
New method for the study of Amaryllidaceae alkaloid biosynthesis using biotransformation of deuterium-labeled precursor in tissue cultures.
2010
Lycorine, the main phenanthridine Amaryllidaceae alkaloid, exhibits significant antitumor activity in cancer cells that display resistance to proapoptotic stimuli: an investigation of structure-activity relationship and mechanistic insight.
2009-10-22
In situ metabolic profiling of single cells by laser ablation electrospray ionization mass spectrometry.
2009-10-15
Effect of abiotic and biotic elicitors on growth and alkaloid accumulation of Lycoris chinensis seedlings.
2009-10-02
Three new alkaloids from Galanthus nivalis and Galanthus elwesii.
2009-10
Alkaloids from Sternbergia colchiciflora.
2009-08-15
Rapid and enantioselective assembly of the lycorine framework using chemoenzymatic techniques.
2009-08-06
Selective cytochrome P450 3A4 inhibitory activity of Amaryllidaceae alkaloids.
2009-06-15
Structure-activity studies on the lycorine pharmacophore: A potent inducer of apoptosis in human leukemia cells.
2009-05
Total synthesis of (-)-lycorine and (-)-2-epi-lycorine by asymmetric conjugate addition cascade.
2009-04-02
Biological evaluation of structurally diverse amaryllidaceae alkaloids and their synthetic derivatives: discovery of novel leads for anticancer drug design.
2009-04
Alkaloid synthesis and accumulation in Leucojum aestivum in vitro cultures.
2009-03
Pressurized liquid extraction and anticholinesterase activity-based thin-layer chromatography with bioautography of Amaryllidaceae alkaloids.
2009-02-09
Lycorine induces apoptosis and down-regulation of Mcl-1 in human leukemia cells.
2009-02-08
A single-amino acid substitution in West Nile virus 2K peptide between NS4A and NS4B confers resistance to lycorine, a flavivirus inhibitor.
2009-02-05
Strategy for adapting wine yeasts for bioethanol production.
2009-01
LCMS and GCMS for the screening of alkaloids in natural and in vitro extracts of Leucojum aestivum.
2009-01
Two novel ceramides with a phytosphingolipid and a tertiary amide structure from Zephyranthes candida.
2009-01
Harnessing gene expression to identify the genetic basis of drug resistance.
2009
New lycorine-type alkaloid from Lycoris traubii and evaluation of antitrypanosomal and antimalarial activities of lycorine derivatives.
2008-12-15
Screening for cytotoxic activity of extracts and isolated alkaloids from bulbs of Hippeastrum vittatum.
2008-10
Anti-inflammatory activity of Crinum asiaticum Linne var. japonicum extract and its application as a cosmeceutical ingredient.
2008-04-09
N-Alkylated galanthamine derivatives: Potent acetylcholinesterase inhibitors from Leucojum aestivum.
2008-04-01
Rapid identification of inhibitors that interfere with poliovirus replication using a cell-based assay.
2008-03
Phytochemical and biological investigation of Hymenocallis littoralis SALISB.
2008-02
Alkaloid variability in Leucojum aestivum from wild populations.
2007-12-12
Revised NMR data for incartine: an alkaloid from Galanthus elwesii.
2007-07-12
Alkaloids from Galanthus nivalis.
2007-07
Alkaloids of Crinum x powellii "Album" (Amaryllidaceae) and their topoisomerase inhibitory activity.
2007-06-05
Cellular ascorbic acid regulates the activity of major peroxidases in the apical poles of germinating white spruce (Picea glauca) somatic embryos.
2006-09-12
Patents

Patents

JPH1179992A
3
US4699912
3
WO2013010274A1
3

Sample Use Guides

In Vivo Use Guide
In a preclinical study, mice were given lycorine at 5 mg/kg/day or 10 mg/kg/day.
Route of Administration: Intraperitoneal
In Vitro Use Guide
In a cell viability assay, PC-3M, LNCaP, 22RV1, DU145 and PNT1A cells were treated with various concentrations of lycorine (0, 0.05, 0.1, 1, 5, 10, 20, 50 and 100 uM) for 48 hours.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:03:06 GMT 2025
Edited
by admin
on Mon Mar 31 19:03:06 GMT 2025
Record UNII
I9Q105R5BU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-401360
Preferred Name English
LYCORINE
MI  
Common Name English
LYCORINE [MI]
Common Name English
(-)-LYCORINE
Common Name English
GALANTHIDINE
Common Name English
BELAMARINE
Common Name English
NSC-683873
Code English
(1S,2S,12BS,12CS)-2,4,5,7,12B,12C-HEXAHYDRO-1H-(1,3)DIOXOLO(4,5-J)PYRROLO(3,2,1-DE)PHENANTHRIDINE-1,2-DIOL
Common Name English
LYCORAN-1.ALPHA.,2.BETA.-DIOL, 3,3A-DIDEHYDRO-
Common Name English
AMARYLLINE
Common Name English
Code System Code Type Description
MERCK INDEX
m6957
Created by admin on Mon Mar 31 19:03:06 GMT 2025 , Edited by admin on Mon Mar 31 19:03:06 GMT 2025
PRIMARY Merck Index
FDA UNII
I9Q105R5BU
Created by admin on Mon Mar 31 19:03:06 GMT 2025 , Edited by admin on Mon Mar 31 19:03:06 GMT 2025
PRIMARY
EPA CompTox
DTXSID60197208
Created by admin on Mon Mar 31 19:03:06 GMT 2025 , Edited by admin on Mon Mar 31 19:03:06 GMT 2025
PRIMARY
CHEBI
2415
Created by admin on Mon Mar 31 19:03:06 GMT 2025 , Edited by admin on Mon Mar 31 19:03:06 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-503-6
Created by admin on Mon Mar 31 19:03:06 GMT 2025 , Edited by admin on Mon Mar 31 19:03:06 GMT 2025
PRIMARY
CAS
476-28-8
Created by admin on Mon Mar 31 19:03:06 GMT 2025 , Edited by admin on Mon Mar 31 19:03:06 GMT 2025
PRIMARY
NSC
683873
Created by admin on Mon Mar 31 19:03:06 GMT 2025 , Edited by admin on Mon Mar 31 19:03:06 GMT 2025
PRIMARY
SMS_ID
100000155488
Created by admin on Mon Mar 31 19:03:06 GMT 2025 , Edited by admin on Mon Mar 31 19:03:06 GMT 2025
PRIMARY
MESH
C015330
Created by admin on Mon Mar 31 19:03:06 GMT 2025 , Edited by admin on Mon Mar 31 19:03:06 GMT 2025
PRIMARY
WIKIPEDIA
LYCORINE
Created by admin on Mon Mar 31 19:03:06 GMT 2025 , Edited by admin on Mon Mar 31 19:03:06 GMT 2025
PRIMARY
EVMPD
SUB129582
Created by admin on Mon Mar 31 19:03:06 GMT 2025 , Edited by admin on Mon Mar 31 19:03:06 GMT 2025
PRIMARY
CHEBI
6601
Created by admin on Mon Mar 31 19:03:06 GMT 2025 , Edited by admin on Mon Mar 31 19:03:06 GMT 2025
PRIMARY
PUBCHEM
72378
Created by admin on Mon Mar 31 19:03:06 GMT 2025 , Edited by admin on Mon Mar 31 19:03:06 GMT 2025
PRIMARY
NSC
401360
Created by admin on Mon Mar 31 19:03:06 GMT 2025 , Edited by admin on Mon Mar 31 19:03:06 GMT 2025
PRIMARY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966