Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H17NO4.ClH.H2O |
| Molecular Weight | 341.787 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.Cl.[H][C@@]12N3CCC1=C[C@H](O)[C@@H](O)[C@@]2([H])C4=CC5=C(OCO5)C=C4C3
InChI
InChIKey=ZOERACVSGIQXBP-CANOEZFNSA-N
InChI=1S/C16H17NO4.ClH.H2O/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;1H2/t11-,14-,15+,16+;;/m0../s1
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P22303|||Q53F46 Gene ID: 43.0 Gene Symbol: ACHE Target Organism: Homo sapiens (Human) |
213.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Localization of ascorbic acid, ascorbic acid oxidase, and glutathione in roots of Cucurbita maxima L. | 2004 Dec |
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| Effects of lycorine on HL-60 cells via arresting cell cycle and inducing apoptosis. | 2004 Dec 17 |
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| New crinine-type alkaloids with inhibitory effect on induction of inducible nitric oxide synthase from Crinum yemense. | 2004 Jul |
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| Acetylcholinesterase enzyme inhibitory effects of amaryllidaceae alkaloids. | 2004 Mar |
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| Choline esterase inhibitory properties of alkaloids from two Nigerian Crinum species. | 2004 Nov |
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| Alkaloids from Leucojum vernum and antiretroviral activity of Amaryllidaceae alkaloids. | 2004 Sep |
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| Identification of natural compounds with antiviral activities against SARS-associated coronavirus. | 2005 Jul |
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| Interaction between yeast mitochondrial and nuclear genomes: null alleles of RTG genes affect resistance to the alkaloid lycorine in rho0 petites of Saccharomyces cerevisiae. | 2005 Jul 18 |
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| Quantitative and cytotoxic activity determinations on Galanthus nivalis subsp. cilicicus. | 2005 Jun |
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| CGC-MS of alkaloids in Leucojum aestivum plants and their in vitro cultures. | 2005 Mar-Apr |
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| Crinamine from Crinum asiaticum var. japonicum inhibits hypoxia inducible factor-1 activity but not activity of hypoxia inducible factor-2. | 2006 Oct |
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| Endogenous ascorbic acid modulates meristem reactivation in white spruce somatic embryos and affects thymidine and uridine metabolism. | 2006 Sep |
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| Synthesis of the tetracyclic framework of the erythrina alkaloids using a [4 + 2]-cycloaddition/Rh(I)-catalyzed cascade of 2-imidofurans. | 2006 Sep 15 |
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| Apoptosis induced by lycorine in KM3 cells is associated with the G0/G1 cell cycle arrest. | 2007 Feb |
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| Preparation of secolycorines against acetylcholinesterase. | 2007 Jan 15 |
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| Alkaloids from Galanthus nivalis. | 2007 Jul |
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| Revised NMR data for incartine: an alkaloid from Galanthus elwesii. | 2007 Jul 12 |
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| Cellular ascorbic acid regulates the activity of major peroxidases in the apical poles of germinating white spruce (Picea glauca) somatic embryos. | 2007 Mar-Apr |
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| Treatment of lycorine on SCID mice model with human APL cells. | 2007 May |
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| N-Alkylated galanthamine derivatives: Potent acetylcholinesterase inhibitors from Leucojum aestivum. | 2008 Apr 1 |
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| Phytochemical and biological investigation of Hymenocallis littoralis SALISB. | 2008 Feb |
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| Rapid identification of inhibitors that interfere with poliovirus replication using a cell-based assay. | 2008 Mar |
|
| Screening for cytotoxic activity of extracts and isolated alkaloids from bulbs of Hippeastrum vittatum. | 2008 Oct |
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| Anti-inflammatory activity of Crinum asiaticum Linne var. japonicum extract and its application as a cosmeceutical ingredient. | 2008 Sep-Oct |
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| Biological evaluation of structurally diverse amaryllidaceae alkaloids and their synthetic derivatives: discovery of novel leads for anticancer drug design. | 2009 Apr |
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| Rapid and enantioselective assembly of the lycorine framework using chemoenzymatic techniques. | 2009 Aug 6 |
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| Lycorine induces apoptosis and down-regulation of Mcl-1 in human leukemia cells. | 2009 Feb 8 |
|
| Pressurized liquid extraction and anticholinesterase activity-based thin-layer chromatography with bioautography of Amaryllidaceae alkaloids. | 2009 Feb 9 |
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| Strategy for adapting wine yeasts for bioethanol production. | 2009 Jan |
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| LCMS and GCMS for the screening of alkaloids in natural and in vitro extracts of Leucojum aestivum. | 2009 Jan |
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| Effect of abiotic and biotic elicitors on growth and alkaloid accumulation of Lycoris chinensis seedlings. | 2009 Jul-Aug |
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| Three new alkaloids from Galanthus nivalis and Galanthus elwesii. | 2009 Oct |
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| In situ metabolic profiling of single cells by laser ablation electrospray ionization mass spectrometry. | 2009 Oct 15 |
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| 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 |
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| The first phytochemical report of Galanthus transcaucasicus Fomin. | 2010 |
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| Galanthamine production by Leucojum aestivum cultures in vitro. | 2010 |
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| New method for the study of Amaryllidaceae alkaloid biosynthesis using biotransformation of deuterium-labeled precursor in tissue cultures. | 2010 |
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| Total synthesis of the lycorenine-type amaryllidaceae alkaloid (+/-)-clivonine via a biomimetic ring-switch from a lycorine-type progenitor. | 2010 Apr 14 |
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| Cytochrome P450 3A4 inhibitory activity studies within the lycorine series of alkaloids. | 2010 Aug |
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| Up-regulation of p21 and TNF-alpha is mediated in lycorine-induced death of HL-60 cells. | 2010 Aug 4 |
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| Quantitative determination of Amaryllidaceae alkaloids from Galanthus reginae-olgae subsp. vernalis and in vitro activities relevant for neurodegenerative diseases. | 2010 Jan |
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| Synthesis and antiplasmodial activity of lycorine derivatives. | 2010 Jul 1 |
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| Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells. | 2010 Jul 23 |
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| HPLC - DAD analysis of lycorine in Amaryllidaceae species. | 2010 Jun |
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| 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 |
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| A survey of phytotoxic microbial and plant metabolites as potential natural products for pest management. | 2010 Sep |
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| Structure-activity studies on acetylcholinesterase inhibition in the lycorine series of Amaryllidaceae alkaloids. | 2010 Sep 1 |
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| In vivo assessment of antiemetic drugs and mechanism of lycorine-induced nausea and emesis. | 2011 Dec |
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| 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 |
|
| Lycorine hydrochloride selectively inhibits human ovarian cancer cell proliferation and tumor neovascularization with very low toxicity. | 2013 Apr 12 |
Patents
Sample Use Guides
In a preclinical study, mice were given lycorine at 5 mg/kg/day or 10 mg/kg/day.
Route of Administration:
Intraperitoneal
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300000017204
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70446239
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SUBSTANCE RECORD
