LYCORINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H17NO4.ClH
Molecular Weight	323.771
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.[H][C@@]12N3CCC1=C[C@H](O)[C@@H](O)[C@@]2([H])C4=CC5=C(OCO5)C=C4C3

InChI

InChIKey=VUVNTYCHKZBOMV-NVJKKXITSA-N

InChI=1S/C16H17NO4.ClH/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;1H/t11-,14-,15+,16+;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25915156

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetylcholinesterase 207 Target ID: P22303\|\|\|Q53F46 Gene ID: 43.0 Gene Symbol: ACHE Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23058055	Inhibitor 8297		213.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25915156	Primary		Preclinical	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23058055	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Alkaloids from Galanthus nivalis.	2007 Jul	17475295
Revised NMR data for incartine: an alkaloid from Galanthus elwesii.	2007 Jul 12	17909498
Alkaloids of Crinum x powellii "Album" (Amaryllidaceae) and their topoisomerase inhibitory activity.	2007 Mar-Apr	17542488
Cellular ascorbic acid regulates the activity of major peroxidases in the apical poles of germinating white spruce (Picea glauca) somatic embryos.	2007 Mar-Apr	17400467
Alkaloid variability in Leucojum aestivum from wild populations.	2007 Sep-Oct	18069233
N-Alkylated galanthamine derivatives: Potent acetylcholinesterase inhibitors from Leucojum aestivum.	2008 Apr 1	18356045
New lycorine-type alkaloid from Lycoris traubii and evaluation of antitrypanosomal and antimalarial activities of lycorine derivatives.	2008 Dec 15	19013823
Phytochemical and biological investigation of Hymenocallis littoralis SALISB.	2008 Feb	18293433
Rapid identification of inhibitors that interfere with poliovirus replication using a cell-based assay.	2008 Mar	18243348
Screening for cytotoxic activity of extracts and isolated alkaloids from bulbs of Hippeastrum vittatum.	2008 Oct	18304791
Anti-inflammatory activity of Crinum asiaticum Linne var. japonicum extract and its application as a cosmeceutical ingredient.	2008 Sep-Oct	18841306
Harnessing gene expression to identify the genetic basis of drug resistance.	2009	19888205
Biological evaluation of structurally diverse amaryllidaceae alkaloids and their synthetic derivatives: discovery of novel leads for anticancer drug design.	2009 Apr	19235683
Total synthesis of (-)-lycorine and (-)-2-epi-lycorine by asymmetric conjugate addition cascade.	2009 Apr 2	19243131
Rapid and enantioselective assembly of the lycorine framework using chemoenzymatic techniques.	2009 Aug 6	19591492
A single-amino acid substitution in West Nile virus 2K peptide between NS4A and NS4B confers resistance to lycorine, a flavivirus inhibitor.	2009 Feb 5	19062063
Lycorine induces apoptosis and down-regulation of Mcl-1 in human leukemia cells.	2009 Feb 8	18829157
Pressurized liquid extraction and anticholinesterase activity-based thin-layer chromatography with bioautography of Amaryllidaceae alkaloids.	2009 Feb 9	19166722
Strategy for adapting wine yeasts for bioethanol production.	2009 Jan	19333452
LCMS and GCMS for the screening of alkaloids in natural and in vitro extracts of Leucojum aestivum.	2009 Jan	19117485
Two novel ceramides with a phytosphingolipid and a tertiary amide structure from Zephyranthes candida.	2009 Jan	18941821
Effect of abiotic and biotic elicitors on growth and alkaloid accumulation of Lycoris chinensis seedlings.	2009 Jul-Aug	19791507
Selective cytochrome P450 3A4 inhibitory activity of Amaryllidaceae alkaloids.	2009 Jun 15	19428250
Alkaloid synthesis and accumulation in Leucojum aestivum in vitro cultures.	2009 Mar	19413113
Structure-activity studies on the lycorine pharmacophore: A potent inducer of apoptosis in human leukemia cells.	2009 May	19464034
Alkaloids from Sternbergia colchiciflora.	2009 May-Jun	19678530
Three new alkaloids from Galanthus nivalis and Galanthus elwesii.	2009 Oct	19382060
In situ metabolic profiling of single cells by laser ablation electrospray ionization mass spectrometry.	2009 Oct 15	19824712
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 Oct 22	19788245
The first phytochemical report of Galanthus transcaucasicus Fomin.	2010	22615606
Galanthamine production by Leucojum aestivum cultures in vitro.	2010	20334039
New method for the study of Amaryllidaceae alkaloid biosynthesis using biotransformation of deuterium-labeled precursor in tissue cultures.	2010	20066175
Total synthesis of the lycorenine-type amaryllidaceae alkaloid (+/-)-clivonine via a biomimetic ring-switch from a lycorine-type progenitor.	2010 Apr 14	20235577
Cytochrome P450 3A4 inhibitory activity studies within the lycorine series of alkaloids.	2010 Aug	20839617
Up-regulation of p21 and TNF-alpha is mediated in lycorine-induced death of HL-60 cells.	2010 Aug 4	20682078
Quantitative determination of Amaryllidaceae alkaloids from Galanthus reginae-olgae subsp. vernalis and in vitro activities relevant for neurodegenerative diseases.	2010 Jan	20645749
Lycorine and its derivatives for anticancer drug design.	2010 Jan	20105122
Synthesis and antiplasmodial activity of lycorine derivatives.	2010 Jul 1	20627737
Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells.	2010 Jul 23	20550100
Alkaloid accumulation in different parts and ages of Lycoris chinensis.	2010 Jul-Aug	20737914
HPLC - DAD analysis of lycorine in Amaryllidaceae species.	2010 Jun	20614813
Trichomonas vaginalis nucleoside triphosphate diphosphohydrolase and ecto-5'-nucleotidase activities are inhibited by lycorine and candimine.	2010 Jun	20176129
Pancratistatin induces apoptosis in clinical leukemia samples with minimal effect on non-cancerous peripheral blood mononuclear cells.	2010 Mar 6	20205924
[Study on the chemical constituents from the bulbs of Zephyranthes candida].	2010 Nov	21434434
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 Nov	20634492
A survey of phytotoxic microbial and plant metabolites as potential natural products for pest management.	2010 Sep	20860028
Structure-activity studies on acetylcholinesterase inhibition in the lycorine series of Amaryllidaceae alkaloids.	2010 Sep 1	20655219
In vivo assessment of antiemetic drugs and mechanism of lycorine-induced nausea and emesis.	2011 Dec	21626407
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 Jan	22155741
Lycorine hydrochloride selectively inhibits human ovarian cancer cell proliferation and tumor neovascularization with very low toxicity.	2013 Apr 12	23376478

Patents

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 `Sat Dec 16 08:54:11 GMT 2023` Edited by `admin` on `Sat Dec 16 08:54:11 GMT 2023`
Record UNII	58F70VH0HS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LYCORINE HYDROCHLORIDE

Common Name

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 HYDROCHLORIDE

Systematic Name

English

LYCORINE HYDROCHLORIDE [MI]

Common Name

English

LYCORINE HYDROCHLORIDE, (+)-

Common Name

English

1H-(1,3)DIOXOLO(4,5-J)PYRROLO(3,2,1-DE)PHENANTHRIDINE-1,2-DIOL, 2,4,5,7,12B,12C-HEXAHYDRO-, HYDROCHLORIDE (1:1), (1S,2S,12BS,12CS)-

Systematic Name

English

LICORIN HYDROCHLORIDE

Common Name

English

Code System Code Type Description

MERCK INDEX

m6957