Compounds > lycoricidine
Page last updated: 2024-11-06

lycoricidine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Lycoricidine is a natural product isolated from the Amaryllidaceae family of plants, known for its unique structure and potential biological activities. It possesses a complex polycyclic framework with an unusual spiro[cyclohexane-1,2'-pyrrolidine] ring system. Research efforts have focused on elucidating its synthesis and exploring its pharmacological properties. While its precise mechanism of action remains under investigation, studies suggest that lycoricidine may exhibit anti-inflammatory and anticancer activities. The compound has been found to inhibit the production of pro-inflammatory cytokines and induce apoptosis in cancer cells. Its potential as a therapeutic agent for inflammatory and neoplastic diseases continues to be explored. The unique structural features and potential medicinal properties make lycoricidine a fascinating target for synthetic and medicinal chemistry research.'

lycoricidine: antineoplastic from daffodil (Narcissus) bulbs; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID73065
CHEMBL ID487798
CHEBI ID6600
SCHEMBL ID13271851
MeSH IDM0484503

Synonyms (15)

Synonym
(2s,3r,4s,4ar)-2,3,4-trihydroxy-3,4,4a,5-tetrahydro-2h-[1,3]dioxolo[4,5-j]phenanthridin-6-one
[1,3]dioxolo[4,5-j]phenanthridin-6(2h)-one, 3,4,4a,5-tetrahydro-2,3,4-trihydroxy-, (2s,3r,4s,4ar)-
C08531
lycoricidine
inchi=1/c14h13no6/c16-8-1-6-5-2-9-10(21-4-20-9)3-7(5)14(19)15-11(6)13(18)12(8)17/h1-3,8,11-13,16-18h,4h2,(h,15,19)/t8-,11+,12+,13-/m0/s1
yydlfvzoidogso-kkbfjbposa-
chebi:6600 ,
CHEMBL487798
nsc 349155
(1,3)dioxolo(4,5-j)phenanthridin-6(2h)-one, 3,4,4a,5-tetrahydro-2,3,4-trihydroxy-, (2s-(2alpha,3beta,4beta,4abeta))-
SCHEMBL13271851
DTXSID10173299
Q27107264
7-deoxy-narciclasine
YYDLFVZOIDOGSO-KKBFJBPOSA-N
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phenanthridinesAny dibenzopyridine based on the skeleton of phenanthridine and its substituted derivatives thereof.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (41)

Assay IDTitleYearJournalArticle
AID377102Cytotoxicity against human MCF7 cells2005Journal of natural products, Feb, Volume: 68, Issue:2
Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1(1).
AID336612Antiviral activity against Japanese encephalitis virus Nakayama infected in african green monkey Vero cells assessed as inhibition of virus-induced cytopathic effect by MTT assay1992Journal of natural products, Nov, Volume: 55, Issue:11
Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances.
AID336624Therapeutic index, ratio of TC50 for african green monkey Vero cells to IC50 for Rift valley fever virus1992Journal of natural products, Nov, Volume: 55, Issue:11
Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances.
AID336625Antiviral activity against Sandfly fever sicilian virus infected in african green monkey Vero cells assessed as inhibition of virus-induced cytopathic effect by MTT assay1992Journal of natural products, Nov, Volume: 55, Issue:11
Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances.
AID1366137Antibacterial activity against Escherichia coli assessed as diameter of inhibition zone at 1 mg/ml2017Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22
Antibacterial constituents of the plant family Amaryllidaceae.
AID336626Therapeutic index, ratio of TC50 for african green monkey Vero cells to IC50 for Sandfly fever sicilian virus1992Journal of natural products, Nov, Volume: 55, Issue:11
Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances.
AID377101Cytotoxicity against human sBxPC-3 cells2005Journal of natural products, Feb, Volume: 68, Issue:2
Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1(1).
AID744400Selectivity index, ratio of CC50 for human Huh7.5 cells to EC50 for Hepatitis C virus2013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Evaluation of anti-HCV activity and SAR study of (+)-lycoricidine through targeting of host heat-stress cognate 70 (Hsc70).
AID336614Antiviral activity against Yellow fever virus Ashibi infected in african green monkey Vero cells assessed as inhibition of virus-induced cytopathic effect by MTT assay1992Journal of natural products, Nov, Volume: 55, Issue:11
Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances.
AID744398Down regulation of Hsc70 protein expression in Hepatitis C virus-infected human Huh7.5 cells assessed as reduction in viral RNA level at 0.1 ug/mL after 24 hrs by Western blotting analysis relative to control2013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Evaluation of anti-HCV activity and SAR study of (+)-lycoricidine through targeting of host heat-stress cognate 70 (Hsc70).
AID336622Therapeutic index, ratio of TC50 for african green monkey Vero cells to IC50 for Punta toro virus Adames1992Journal of natural products, Nov, Volume: 55, Issue:11
Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances.
AID378666Growth inhibition of human KM20L2 cells2006Journal of natural products, Jan, Volume: 69, Issue:1
Isolation and structural modification of 7-deoxynarciclasine and 7-deoxy-trans-dihydronarciclasine.
AID744409Inhibition of Hsc70 mRNA expression in Hepatitis C virus-infected human Huh7.5 cells at 10 ug/mL after 24 hrs by RT-PCR analysis relative to control2013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Evaluation of anti-HCV activity and SAR study of (+)-lycoricidine through targeting of host heat-stress cognate 70 (Hsc70).
AID1366138Antibacterial activity against Staphylococcus aureus assessed as diameter of inhibition zone at 1 mg/ml2017Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22
Antibacterial constituents of the plant family Amaryllidaceae.
AID378667Growth inhibition of human DU145 cells2006Journal of natural products, Jan, Volume: 69, Issue:1
Isolation and structural modification of 7-deoxynarciclasine and 7-deoxy-trans-dihydronarciclasine.
AID377103Cytotoxicity against human SF-268 cells2005Journal of natural products, Feb, Volume: 68, Issue:2
Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1(1).
AID377100Cytotoxicity against mouse P388 cells2005Journal of natural products, Feb, Volume: 68, Issue:2
Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1(1).
AID377099Aqueous solubility at 25 degC2005Journal of natural products, Feb, Volume: 68, Issue:2
Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1(1).
AID378661Growth inhibition of mouse P388 cells2006Journal of natural products, Jan, Volume: 69, Issue:1
Isolation and structural modification of 7-deoxynarciclasine and 7-deoxy-trans-dihydronarciclasine.
AID377105Cytotoxicity against human KM20L2 cells2005Journal of natural products, Feb, Volume: 68, Issue:2
Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1(1).
AID378664Growth inhibition of human SF269 cells2006Journal of natural products, Jan, Volume: 69, Issue:1
Isolation and structural modification of 7-deoxynarciclasine and 7-deoxy-trans-dihydronarciclasine.
AID744411Down regulation of Hsc70 protein expression in Hepatitis C virus-infected human Huh7.5 cells at 0.1 ug/mL after 24 hrs by Western blotting analysis relative to actin expression2013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Evaluation of anti-HCV activity and SAR study of (+)-lycoricidine through targeting of host heat-stress cognate 70 (Hsc70).
AID332888In vivo cytotoxicity against mouse P388 cells at 12.5 mg/kg relative to control
AID744401Antiviral activity against Hepatitis C virus infected in human Huh7.5 cells after 96 hrs by fluorescence microscopic analysis2013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Evaluation of anti-HCV activity and SAR study of (+)-lycoricidine through targeting of host heat-stress cognate 70 (Hsc70).
AID378665Growth inhibition of human NCI-H460 cells2006Journal of natural products, Jan, Volume: 69, Issue:1
Isolation and structural modification of 7-deoxynarciclasine and 7-deoxy-trans-dihydronarciclasine.
AID378662Growth inhibition of human BXPC3 cells2006Journal of natural products, Jan, Volume: 69, Issue:1
Isolation and structural modification of 7-deoxynarciclasine and 7-deoxy-trans-dihydronarciclasine.
AID377106Cytotoxicity against human DU145 cells2005Journal of natural products, Feb, Volume: 68, Issue:2
Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1(1).
AID336615Therapeutic index, ratio of TC50 for african green monkey Vero cells to IC50 for Yellow fever virus Ashibi1992Journal of natural products, Nov, Volume: 55, Issue:11
Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances.
AID332893In vivo cytotoxicity against mouse P388 cells at 25 mg/kg relative to control
AID336623Antiviral activity against Rift Valley fever virus infected in african green monkey Vero cells after 6 days by plaque reduction assay1992Journal of natural products, Nov, Volume: 55, Issue:11
Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances.
AID336617Therapeutic index, ratio of TC50 for african green monkey Vero cells to IC50 for Dengue type 4 virus1992Journal of natural products, Nov, Volume: 55, Issue:11
Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances.
AID336613Therapeutic index, ratio of TC50 for african green monkey Vero cells to IC50 for Japanese encephalitis virus Nakayama1992Journal of natural products, Nov, Volume: 55, Issue:11
Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances.
AID744399Down regulation of Hsc70 protein expression in Hepatitis C virus-infected human Huh7.5 cells at 0.1 ug/mL after 24 hrs by Western blotting analysis relative to control2013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Evaluation of anti-HCV activity and SAR study of (+)-lycoricidine through targeting of host heat-stress cognate 70 (Hsc70).
AID744408Inhibition of Hsc70 mRNA expression in Hepatitis C virus-infected human Huh7.5 cells at 100 ug/mL after 24 hrs by RT-PCR analysis relative to control2013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Evaluation of anti-HCV activity and SAR study of (+)-lycoricidine through targeting of host heat-stress cognate 70 (Hsc70).
AID744412Cytotoxicity against human Huh7.5 cells treated after 96 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Evaluation of anti-HCV activity and SAR study of (+)-lycoricidine through targeting of host heat-stress cognate 70 (Hsc70).
AID377104Cytotoxicity against human NCI-H460 cells2005Journal of natural products, Feb, Volume: 68, Issue:2
Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1(1).
AID378663Growth inhibition of human MCF7 cells2006Journal of natural products, Jan, Volume: 69, Issue:1
Isolation and structural modification of 7-deoxynarciclasine and 7-deoxy-trans-dihydronarciclasine.
AID744410Down regulation of Hsc70 protein expression in Hepatitis C virus-infected human Huh7.5 cells assessed as reduction in viral RNA level at 0.1 ug/mL after 24 hrs by Western blotting analysis relative to actin expression2013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Evaluation of anti-HCV activity and SAR study of (+)-lycoricidine through targeting of host heat-stress cognate 70 (Hsc70).
AID336616Antiviral activity against Dengue virus type 4 infected in african green monkey Vero cells after 6 days by plaque reduction assay1992Journal of natural products, Nov, Volume: 55, Issue:11
Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances.
AID332887Cytotoxicity against mouse 9PS cells
AID336621Antiviral activity against Punta Toro virus Adames infected in african green monkey Vero cells assessed as inhibition of virus-induced cytopathic effect by MTT assay1992Journal of natural products, Nov, Volume: 55, Issue:11
Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (7.14)18.2507
2000's7 (50.00)29.6817
2010's6 (42.86)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.10

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index20.10 (24.57)
Research Supply Index2.77 (2.92)
Research Growth Index5.25 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.10)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (13.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (86.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
inositol
Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.		2.2110cyclitol;
hexol
phenanthridone
phenanthridone: coal tar derivative; structure given in first source. phenanthridone : A member of the class of phenanthridines that is phenanthridine with an oxo substituent at position 6. A poly(ADP-ribose) polymerase (PARP) inhibitor, it has been shown to exhibit immunosuppressive activity.		2.0310lactam;
phenanthridines		EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor;
immunosuppressive agent;
mutagen
penicillin g
Penicillin G: A penicillin derivative commonly used in the form of its sodium or potassium salts in the treatment of a variety of infections. It is effective against most gram-positive bacteria and against gram-negative cocci. It has also been used as an experimental convulsant because of its actions on GAMMA-AMINOBUTYRIC ACID mediated synaptic transmission.. benzylpenicillin : A penicillin in which the substituent at position 6 of the penam ring is a phenylacetamido group.		3.2510penicillin allergen;
penicillin		antibacterial drug;
drug allergen;
epitope
bromobenzene
[no description available]		7.1510bromoarene;
bromobenzenes;
volatile organic compound		hepatotoxic agent;
mouse metabolite;
non-polar solvent
galantamine
Galantamine: A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.. galanthamine : A benzazepine alkaloid isolated from certain species of daffodils.		3.2510benzazepine alkaloid fundamental parent;
benzazepine alkaloid;
organic heterotetracyclic compound;
tertiary amino compound		antidote to curare poisoning;
cholinergic drug;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
plant metabolite
narciclasine
narciclasine: antitumor alkaloid from bulbs of Narcissus species		5.0470phenanthridinesmetabolite
lycorine
lycorine: from bulbs of LYCORIS & other plants; RN given refers to (1 alpha,2 beta)-isomer; structure in Merck Index, 9th ed, #5444. lycorine : An indolizidine alkaloid that is 3,12-didehydrogalanthan substituted by hydroxy groups at positions and 2 and a methylenedioxy group across positions 9 and 10. Isolated from Crinum asiaticum, it has been shown to exhibit antimalarial activity.		4.3430indolizidine alkaloidanticoronaviral agent;
antimalarial;
plant metabolite;
protein synthesis inhibitor
hippadine
hippadine: isolated from Crinum bulbs		3.2510
trans-dihydronarciclasine
[no description available]		3.8130
lycorenine
lycorenine: from Lycoris radiata Herb. (Liliaceae); has vasodepressor effect; RN from 9th CI; RN given refers to (7alpha)-isomer		3.2510alkaloid
sitosterol, (3beta)-isomer
Sobatum: tradename; active fraction of Solanum trilobatum; reduces side-effects of radiation-induced toxicity. sitosterol : A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3.		3.25103beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
C29-steroid;
phytosterols;
stigmastane sterol		anticholesteremic drug;
antioxidant;
mouse metabolite;
plant metabolite;
sterol methyltransferase inhibitor
anhydrolycorinone
anhydrolycorinone: structure in first source		3.2510phenanthridines
pancratistatin
pancratistatin: an isocarbostyril from Amaryllidaceae		3.8130citraconoyl group
farrerol
farrerol: expectorant principle isolated from leaves of Rhododendron dauricum L; structure		3.2510organic molecular entitymetabolite
1-O-Acetyllycorine
1-acetyllycorine: has antiviral activity; structure in first source		3.2510alkaloid
pancracine
pancracine: structure in first source		3.2510isoquinoline alkaloid fundamental parent;
isoquinoline alkaloid
pseudolycorine
pseudolycorine: alkaloid isolated from Narcissus tazetta var. chinensis Roem, N. papyraceus or Lycoris radiata Herb; structure in first source		1.9810phenanthridines
7-deoxypancratistatin
7-deoxypancratistatin: a phytogenic antineoplastic agent; structure in first source		1.9810phenanthridines
7-deoxy-trans-dihydronarciclasine
7-deoxy-trans-dihydronarciclasine: structure in first source		2.9340
sideroxylin
sideroxylin: from Hydrastis canadensis; structure in first source. sideroxylin : A monomethoxyflavone that is flavone substituted by a methoxy group at position 7, hydroxy groups at positions 5 and 4' and methyl groups at positions 6 and 8. It has been isolated from Hydrastis canadensis and Eucalyptus species.		3.2510dihydroxyflavone;
monomethoxyflavone		plant metabolite
ungeremine
[no description available]		3.2510organic molecular entitymetabolite
lyoniside
daucosterol : A steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa.		3.2510beta-D-glucoside;
monosaccharide derivative;
steroid saponin		plant metabolite
amarbellisine
amarbellisine: structure in first source		3.2510
montanine
montanine: has anxiolytic, antidepressant, and anticonvulsant activities		3.2510
tetracycline
Tetracycline: A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.. tetracycline : A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.		3.2510
phenanthrenes
Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.		2.0310
ConditionIndicatedRelationship StrengthStudiesTrials
Encephalitis, Japanese B
[description not available]		01.9810
Encephalitis, Japanese
A mosquito-borne encephalitis caused by the Japanese B encephalitis virus (ENCEPHALITIS VIRUS, JAPANESE) occurring throughout Eastern Asia and Australia. The majority of infections occur in children and are subclinical or have features limited to transient fever and gastrointestinal symptoms. Inflammation of the brain, spinal cord, and meninges may occur and lead to transient or permanent neurologic deficits (including a POLIOMYELITIS-like presentation); SEIZURES; COMA; and death. (From Adams et al., Principles of Neurology, 6th ed, p751; Lancet 1998 Apr 11;351(9109):1094-7)		01.9810
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		02.0310