Page last updated: 2024-12-06

laurolitsine

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

Description

laurolitsine: RN given for (S)-isomer; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

laurolistine : An aporphine alkaloid that is noraporphine substituted by hydroxy groups at positions 2 and 9 and methoxy groups at positions 1 and 10. Isolated from Litsea glutinosa and Lindera chunii, exhibits inhibitory activity against HIV-1 integrase. [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]

FloraRankFlora DefinitionFamilyFamily Definition
LitseagenusA plant genus of the family LAURACEAE. Members contain laurotetanine and other APORPHINES.[MeSH]LauraceaeA family of mainly aromatic evergreen plants in the order Laurales. The laurel family includes 2,200 species in 45 genera and from these are derived medicinal extracts, essential oils, camphor and other products.[MeSH]
Lindera chuniispecies[no description available]LauraceaeA family of mainly aromatic evergreen plants in the order Laurales. The laurel family includes 2,200 species in 45 genera and from these are derived medicinal extracts, essential oils, camphor and other products.[MeSH]
Litsea glutinosaspecies[no description available]LauraceaeA family of mainly aromatic evergreen plants in the order Laurales. The laurel family includes 2,200 species in 45 genera and from these are derived medicinal extracts, essential oils, camphor and other products.[MeSH]

Cross-References

ID SourceID
PubMed CID22179
CHEMBL ID487388
CHEBI ID66557
MeSH IDM0283307

Synonyms (37)

Synonym
4h-dibenzo[de,g]quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-, (6as)-
5890-18-6
laurolistine
laurolitsine
4h-dibenzo(de,g)quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-
1,10-dimethoxy-6a-alpha-noraporphine-2,9-diol
norboldine
6a-alpha-noraporphine-2,9-diol, 1,10-dimethoxy-
dimethoxy-1,10 dihydroxy-2,9 nor-aporphine [french]
568-39-8
C16984
chebi:66557 ,
(+)-norboldine
CHEMBL487388 ,
[(+)-norboldine]
bdbm50292446
(s)-1,10-dimethoxy-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-2,9-diol
(6as)-1,10-dimethoxy-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-2,9-diol
5mt88is14f ,
dimethoxy-1,10 dihydroxy-2,9 nor-aporphine
unii-5mt88is14f
4h-dibenzo(de,g)quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-, (6as)-
1,10-dimethoxy-6a-.alpha.-noraporphine-2,9-diol
laurolitsine, (+)-
(+)-laurolitsine
4h-dibenzo(de,g)quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-, (s)-
6a-.alpha.-noraporphine-2,9-diol, 1,10-dimethoxy-
2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylicacid
DTXSID30207641
AKOS037515021
Q27135167
HY-N2352
CS-0022440
norboldine; (s)-5,6,6a,7-tetrahydro-1,10-dimethoxy-4h-dibenzo[de,g]quinoline-2,9-diol
A869328
F82119
MS-24584

Research Excerpts

Overview

Laurolitsine is an aporphine alkaloid and exhibits potent antihyperglycemic and antihyperlipidemic effects.

ExcerptReferenceRelevance
"Laurolitsine is an aporphine alkaloid and exhibits potent antihyperglycemic and antihyperlipidemic effects in ob/ob mice."( Study on the pharmacokinetics, tissue distribution and excretion of laurolitsine from
Lu, WY; Ma, N; Tan, YF; Wang, RQ; Wang, WT; Wu, Y; Zhang, XP; Zhang, Y, 2021
)
2.3

Pharmacokinetics

ExcerptReferenceRelevance
"This study established a simple, rapid and accurate LC-MS/MS method to determine laurolitsine in different rat samples and successful application in a pharmacokinetic study."( Study on the pharmacokinetics, tissue distribution and excretion of laurolitsine from
Lu, WY; Ma, N; Tan, YF; Wang, RQ; Wang, WT; Wu, Y; Zhang, XP; Zhang, Y, 2021
)
1.08
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
HIV-1 integrase inhibitorAn inhibitor of HIV-1 integrase, an enzyme required for the integration of the genetic material of the retrovirus into the DNA of the infected cells.
[role 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]

Drug Classes (3)

ClassDescription
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
aporphine alkaloidAny benzylisoquinoline alkaloid that has a structure based on 4H-dibenzo[de,g]quinoline or its 3-methyl derivative.
[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]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DRattus norvegicus (Norway rat)IC50 (µMol)2.50000.00030.50267.7625AID313111
Sodium-dependent dopamine transporterRattus norvegicus (Norway rat)IC50 (µMol)16.50000.00070.97749.7000AID313113
D(2) dopamine receptorRattus norvegicus (Norway rat)IC50 (µMol)6.80000.00010.54948.4000AID313112
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID359909Inhibition of dopamine transporter-mediated [3H]dopamine uptake in Wistar rat striatal synaptosomes by liquid scintillation spectrometry1995Journal of natural products, Oct, Volume: 58, Issue:10
Effects of various isoquinoline alkaloids on in vitro 3H-dopamine uptake by rat striatal synaptosomes.
AID359911Ratio of IC50 for rat striatum dopamine D2 receptor to IC50 for Wistar rat striatal synaptosomes dopamine transporter-mediated [3H]dopamine uptake1995Journal of natural products, Oct, Volume: 58, Issue:10
Effects of various isoquinoline alkaloids on in vitro 3H-dopamine uptake by rat striatal synaptosomes.
AID378210Cytotoxicity against human HA59T cells upto 30 by MTS colorimetric assay2000Journal of natural products, Nov, Volume: 63, Issue:11
Cytotoxic constituents of Polyalthia longifolia var. pendula.
AID376470Antiviral activity against Poliovirus 2 Sabin 2 in african green monkey Vero cells assessed as log reduction in virus titers after at 0.1 multiple round of replication at their respective maximum tolerated concentration after 32 hrs1998Journal of natural products, Apr, Volume: 61, Issue:4
Antipoliovirus structure-activity relationships of some aporphine alkaloids.
AID313111Displacement of [3H]SCH-23390 from rat dopamine D1 receptor2007Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2
Advances in development of dopaminergic aporphinoids.
AID378208Cytotoxicity against human AGS cells upto 30 uM by MTS colorimetric assay2000Journal of natural products, Nov, Volume: 63, Issue:11
Cytotoxic constituents of Polyalthia longifolia var. pendula.
AID354688Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 as [3H]hypoxanthine uptake1996Journal of natural products, Jun, Volume: 59, Issue:6
Costaricine, a new antiplasmodial bisbenzylisoquinoline alkaloid from Nectandra salicifolia trunk bark.
AID376467Cytotoxicity against african green monkey Vero cells1998Journal of natural products, Apr, Volume: 61, Issue:4
Antipoliovirus structure-activity relationships of some aporphine alkaloids.
AID376475Antiviral activity against Poliovirus 2 Sabin 2 in african green monkey Vero cells assessed as log reduction in virus titers after at 0.001 multiple round of replication at their respective maximum tolerated concentration after 32 hrs1998Journal of natural products, Apr, Volume: 61, Issue:4
Antipoliovirus structure-activity relationships of some aporphine alkaloids.
AID376469Selectivity index, ratio of CC50 for african green monkey Vero cells to ED50 for Poliovirus 2 Sabin 21998Journal of natural products, Apr, Volume: 61, Issue:4
Antipoliovirus structure-activity relationships of some aporphine alkaloids.
AID313113Displacement of [3H]DA from rat DAT2007Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2
Advances in development of dopaminergic aporphinoids.
AID378209Cytotoxicity against human DLD1 cells upto 30 by MTS colorimetric assay2000Journal of natural products, Nov, Volume: 63, Issue:11
Cytotoxic constituents of Polyalthia longifolia var. pendula.
AID378211Cytotoxicity against human HepG2 cells upto 30 by MTS colorimetric assay2000Journal of natural products, Nov, Volume: 63, Issue:11
Cytotoxic constituents of Polyalthia longifolia var. pendula.
AID376473Antiviral activity against Poliovirus 2 Sabin 2 in african green monkey Vero cells assessed as log reduction in virus titers after at 0.01 multiple round of replication at their respective maximum tolerated concentration after 32 hrs1998Journal of natural products, Apr, Volume: 61, Issue:4
Antipoliovirus structure-activity relationships of some aporphine alkaloids.
AID313112Displacement of [3H]raclopride from rat dopamine D2 receptor2007Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2
Advances in development of dopaminergic aporphinoids.
AID359910Ratio of IC50 for rat striatum dopamine D1 receptor to IC50 for Wistar rat striatal synaptosomes dopamine transporter-mediated [3H]dopamine uptake1995Journal of natural products, Oct, Volume: 58, Issue:10
Effects of various isoquinoline alkaloids on in vitro 3H-dopamine uptake by rat striatal synaptosomes.
AID354687Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 as [3H]hypoxanthine uptake1996Journal of natural products, Jun, Volume: 59, Issue:6
Costaricine, a new antiplasmodial bisbenzylisoquinoline alkaloid from Nectandra salicifolia trunk bark.
AID376468Antiviral activity against Poliovirus 2 Sabin 2 infected in african green monkey Vero cells at 0.001 multiplicity of infection assessed as inhibition of virus-induced cytopathogenicity1998Journal of natural products, Apr, Volume: 61, Issue:4
Antipoliovirus structure-activity relationships of some aporphine alkaloids.
AID376471Cytotoxicity against african green monkey Vero cells assessed as drug concentration at which no cellular alteration was microscopically detected1998Journal of natural products, Apr, Volume: 61, Issue:4
Antipoliovirus structure-activity relationships of some aporphine alkaloids.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (40.00)18.2507
2000's2 (20.00)29.6817
2010's2 (20.00)24.3611
2020's2 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.12

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 Index20.12 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.88 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.12)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (10.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (90.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]