Compounds > pronuciferine
Page last updated: 2024-12-08

pronuciferine

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

Description

pronuciferine: alkaloid; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

(+)-pronuciferine : An isoquinoline alkaloid isolated from Berberis coletioides. [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
BerberisgenusA plant genus in the family BERBERIDACEAE. The common names of Barberry or Oregon Grape are also used for MAHONIA. The similar-named Bayberry is the unrelated MYRICA. Oregon Grape was classified by Pursh as a Berberis but Nuttall claimed it is different enough to call it a new genus, MAHONIA. Botanists insist on this name while horticulturists stay with Mahonia. They are shrubs with yellow wood and usually three-branched spines at the base of leafstalks. Flowers are yellow, six-petaled and fruit is a berry with one to several seeds. Members contain BERBERINE.[MeSH]BerberidaceaeThe Barberry plant family of the order Ranunculales, subclass Magnoliidae, class Magnoliopsida. The shrubs have spiny leaves.[MeSH]

Cross-References

ID SourceID
PubMed CID200480
CHEMBL ID237766
CHEBI ID42
MeSH IDM0503211

Synonyms (27)

Synonym
pronuciferine
spiro(2,5-cyclohexadiene-1,7'-1'h-cyclopent(ij)isoquinolin)-4-one, 2',3',8',8'a-tetrahydro-5',6'-dimethoxy-1'-methyl-, (r)-
NCI60_009013
nsc628007
nsc-628007
(+)-pronuciferine
2128-60-1
C09611
milthanthine
n-methylstepharine
pronuciferin
CHEBI:42 ,
(8a'r)-5',6'-dimethoxy-1'-methyl-2',3',8',8a'-tetrahydro-1'h,4h-spiro[cyclohexa-2,5-diene-1,7'-cyclopenta[ij]isoquinolin]-4-one
n,o-dimethylcrotonosine
CHEMBL237766
unii-860x46gii1
860x46gii1 ,
spiro(2,5-cyclohexadiene-1,7'(1'h)-cyclopent(ij)isoquinolin)-4-one, 2',3',8',8'a-tetrahydro-5',6'-dimethoxy-1'-methyl-, (8'ar)-
spiro(2,5-cyclohexadiene-1,7'(1'h)-cyclopent(ij)isoquinolin)-4-one, 2',3',8',8'a-tetrahydro-5',6'-dimethoxy-1'-methyl-, (r)-
pronuciferine, (+)-
spiro[2,5-cyclohexadiene-1,7'(1'h)-cyclopent[ij]isoquinolin]-4-one, 2',3',8',8'a-tetrahydro-5',6'-dimethoxy-1'-methyl-, (r)-
WUYQEGNOQLRQAQ-CQSZACIVSA-N
5',6'-dimethoxy-1'-methyl-2',3',8',8'a-tetrahydro-1'h-spiro[cyclohexa-2,5-diene-1,7'-cyclopenta[ij]isoquinolin]-4-one
DTXSID60943782
Q27105211
(4r)-10,11-dimethoxy-5-methylspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohexa-2,5-diene]-1'-one
AKOS040753619

Research Excerpts

Overview

Pronuciferine is a naturally occurring proaporphine alkaloid. It belongs to isoquinoline alkaloids.

ExcerptReferenceRelevance
"Pronuciferine is a naturally occurring proaporphine alkaloid that belongs to isoquinoline alkaloids. "( Neuroactivity of naturally occurring proaporphine alkaloid, pronuciferine.
Bayazeid, O; Eylem, CC; Nemutlu, E; Yalçın, FN, 2020)		2.24
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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 (5)

ClassDescription
isoquinoline alkaloidAny alkaloid that has a structure based on an isoquinoline nucleus. They are derived from the amino acids like tyrosine and phenylalanine.
isoquinolinesA class of organic heteropolycyclic compound consisting of isoquinoline and its substitution derivatives.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
cyclic ketone
organic heterotetracyclic compound
[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 (14)

Assay IDTitleYearJournalArticle
AID301054Selectivity index, ratio of CC50 for human Hep G2.2.15 cells to IC50 for HBV e antigen secretion in HBV transfected Hep G2.2.15 cells2007Bioorganic & medicinal chemistry letters, Oct-01, Volume: 17, Issue:19
Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida.
AID721320Inhibition of melanogenesis in mouse B16-4A5 cells at 100 uM after 72 hrs by spectrophotometry2013Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3
Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells.
AID721318Cytotoxicity against mouse B16-4A5 cells assessed as cell viability at 30 uM after 70 hrs by WST-8 assay2013Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3
Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells.
AID301052Antiviral activity against HBV transfected Hep G2.2.15 cells assessed as inhibition of e antigen HBsAg secretion2007Bioorganic & medicinal chemistry letters, Oct-01, Volume: 17, Issue:19
Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida.
AID301050Cytotoxicity against human Hep G2.2.15 cells2007Bioorganic & medicinal chemistry letters, Oct-01, Volume: 17, Issue:19
Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida.
AID301051Antiviral activity against HBV transfected Hep G2.2.15 cells assessed as inhibition of surface antigen HBsAg secretion2007Bioorganic & medicinal chemistry letters, Oct-01, Volume: 17, Issue:19
Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida.
AID721322Inhibition of melanogenesis in mouse B16-4A5 cells at 10 uM after 72 hrs by spectrophotometry2013Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3
Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells.
AID301053Selectivity index, ratio of CC50 for human Hep G2.2.15 cells to IC50 for surface antigen HBsAg secretion in HBV transfected Hep G2.2.15 cells2007Bioorganic & medicinal chemistry letters, Oct-01, Volume: 17, Issue:19
Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida.
AID722233Inhibition of melanogenesis in mouse B16-4A5 cells at 1 uM after 72 hrs by spectrophotometry2013Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3
Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells.
AID722232Inhibition of melanogenesis in mouse B16-4A5 cells at 3 uM after 72 hrs by spectrophotometry2013Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3
Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells.
AID721317Cytotoxicity against mouse B16-4A5 cells assessed as cell viability at 100 uM after 70 hrs by WST-8 assay2013Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3
Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells.
AID752787Inhibition of porcine pancreatic lipase using para-nitrophenyl butyrate as substrate at 100 uM by ELISA2013Bioorganic & medicinal chemistry letters, Jun-15, Volume: 23, Issue:12
Chemical constituents from Nelumbo nucifera leaves and their anti-obesity effects.
AID721319Inhibition of melanogenesis in mouse B16-4A5 cells after 72 hrs by spectrophotometry2013Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3
Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells.
AID721321Inhibition of melanogenesis in mouse B16-4A5 cells at 30 uM after 72 hrs by spectrophotometry2013Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3
Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (41.67)29.6817
2010's4 (33.33)24.3611
2020's3 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.68

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 Index19.68 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.61 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.68)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other12 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
methanol
Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.		2.2510alkyl alcohol;
one-carbon compound;
primary alcohol;
volatile organic compound		amphiprotic solvent;
Escherichia coli metabolite;
fuel;
human metabolite;
mouse metabolite;
Mycoplasma genitalium metabolite
1,2,3,4-tetrahydroisoquinoline
1,2,3,4-tetrahydroisoquinoline: RN given refers to cpd with locants as specified		2.0810isoquinolines
liriodenine
liriodenine: structure given in first source. liriodenine : An oxoaporphine alkaloid that is 4,5,6,6a-tetradehydronoraporphin-7-one substituted by a methylenedioxy group across positions 1 and 2. It is isolated from Annona glabra and has been shown to exhibit antimicrobial and cytotoxic activities.		2.0810alkaloid antibiotic;
cyclic ketone;
organic heteropentacyclic compound;
oxacycle;
oxoaporphine alkaloid		antifungal agent;
antimicrobial agent;
antineoplastic agent;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
metabolite
nuciferine
nuciferine: CNS depressant; glutamic acid antagonist; RN given refers to (R)-isomer; structure		2.7730
2-methyl-1,2,3,4-tetrahydroisoquinoline
[no description available]		2.0810
lirinidine
lirinidine: from Nelumbro nucifera; RN given refers to (S)-isomer		2.2510
lamivudine
[no description available]		2.0310monothioacetal;
nucleoside analogue;
oxacycle;
primary alcohol		allergen;
anti-HBV agent;
antiviral drug;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor;
HIV-1 reverse transcriptase inhibitor;
prodrug
glaziovine
glaziovine: a proaporphine alkaloid isolated from Ocotea glaziovii (Lauraceae) found to be similar in activity as an anxiolitic drug to diazepam; structure; RN given refers to (S)-isomer		2.0310
(-)-catechin
(-)-catechin : The (-)-enantiomer of catechin.		2.0810catechinmetabolite
magnoflorine
magnoflorine: opium alkaloid having the aporphine configuration; RN given refers to parent cpd(S)-isomer; structure. (S)-magnoflorine : An aporphine alkaloid that is (S)-corytuberine in which the nitrogen has been quaternised by an additional methyl group.		2.0310aporphine alkaloid;
quaternary ammonium ion		plant metabolite
armepavine
[no description available]		2.0810
stepharine
stepharine: RN given refers to (R)-isomer. stepharine : An isoquinoline alkaloid with formula C18H19NO3 that is isolated from several species of Stephania.		7.0310
aporphine
aporphine: RN given refers to parent cpd without isomeric designation. aporphine : An isoquinoline alkaloid that is the N-methyl derivative of 5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline.		7.0410aporphine alkaloid;
isoquinoline alkaloid fundamental parent;
tertiary amino compound
roemerine
roemerine: from root tubers of Stephania kwangsiensis H.S. Lo; RN given refers to (R)-isomer; synonym aporeine refers to (S)-isomer; structure in Merck Index, 9th ed, #779		2.4920isoquinoline alkaloid
lysicamine
lysicamine: oxoaporphine alkaloid; structure in first source		2.0810alkaloid antibiotic;
oxoaporphine alkaloid		metabolite
asimilobine
asimilobine: from Nelumbro nucifera; RN given refers to (R)-isomer		2.2510aporphine alkaloidmetabolite
taxifolin
(+)-taxifolin : A taxifolin that has (2R,3R)-configuration.		2.0810taxifolinmetabolite
reticuline
reticuline: opium alkaloid; dopamine receptor blocker; RN given refers to (S)-isomer; structure. (S)-reticuline : The (S)-enantiomer of reticuline.		2.0310reticulineEC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor
arbutin
hydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.		2.0810beta-D-glucoside;
monosaccharide derivative		Escherichia coli metabolite;
plant metabolite
dehydrovomifoliol
dehydrovomifoliol: isolated from Litsea sessilis; structure in first source. (6S)-dehydrovomifoliol : A dehydrovomifoliol that has S-configuration at the chiral centre.. dehydrovomifoliol : A fenchane monoterpenoid that is substituted by methyl groups at positions 3, 5, and 5, and by both a hydroxy group and a 3-oxobut-1-en-1-yl group at position 4.		2.0810dehydrovomifoliolplant metabolite
quercetin
[no description available]		2.08107-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
luteolin
[no description available]		2.08103'-hydroxyflavonoid;
tetrahydroxyflavone		angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
apoptosis inducer;
c-Jun N-terminal kinase inhibitor;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
immunomodulator;
nephroprotective agent;
plant metabolite;
radical scavenger;
vascular endothelial growth factor receptor antagonist
vomifoliol
blumenol A: a phytotoxin isolated from Oryza sativa Awaakamai; structure in first source. vomifoliol : A fenchane monoterpenoid that is 3,5,5-trimethylcyclohex-2-en-1-one substituted by a hydroxy and a (1E)-3-hydroxybut-1-en-1-yl group at position 4.. (6S,9R)-vomifoliol : A (6S)-vomifoliol with a R configuration for the hydroxy group at position 9.		2.0810(6S)-vomifoliolmetabolite;
phytotoxin
feruloyltyramine
feruloyltyramine: structure given in first source; isolated from Cannabis sativa seeds, roots, leaves, and resin; induces hypothermia and motor incoordination in mice; moupinamide is (E)-isomer		2.0810tyraminesmetabolite
quercetin 3-o-glucopyranoside
quercetin 3-O-glucopyranoside: structure in first source. quercetin 3-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells		2.0810beta-D-glucoside;
monosaccharide derivative;
quercetin O-glucoside;
tetrahydroxyflavone		antineoplastic agent;
antioxidant;
antipruritic drug;
bone density conservation agent;
geroprotector;
histamine antagonist;
osteogenesis regulator;
plant metabolite
kaempferol
[no description available]		2.08107-hydroxyflavonol;
flavonols;
tetrahydroxyflavone		antibacterial agent;
geroprotector;
human blood serum metabolite;
human urinary metabolite;
human xenobiotic metabolite;
plant metabolite
astragalin
kaempferol-3-O-glucoside: isolated from the pit of Mahkota dewa; structure in first source. kaempferol 3-O-beta-D-glucoside : A kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage.		2.0810beta-D-glucoside;
kaempferol O-glucoside;
monosaccharide derivative;
trihydroxyflavone		plant metabolite;
trypanocidal drug
n-(4-hydroxy-beta-phenethyl)-4-hydroxycinnamide
trans-N-p-coumaroyl tyramine: from the twigs of Celtis chinensis; structure in first source		2.0810hydroxycinnamic acidmetabolite
feruloyltyramine, (z)-isomer
[no description available]		2.0810hydroxycinnamic acid
acutumine
acutumine: dechloroacutumine is the dechloro derivative of acutumine		2.0310alkaloid
grasshopper ketone
grasshopper ketone: a phytotoxin isolated from Oryza sativa Awaakamai; structure in first source. grasshopper ketone : A member of the class of allenes that is cyclohexane substituted by 3-oxobut-1-en-1-ylidene, methyl, hydroxy, hydroxy, methyl and methyl groups at positions 1, 2, 2, 4, 6 and 6, respectively (the 2R,3R,4S-stereoisomer). It is isolated from the grasshopper, Romalea microptera.		2.0810
ConditionIndicatedRelationship StrengthStudiesTrials
B16 Melanoma
[description not available]		02.0810
Obesity
A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).		02.0810
Acute Confusional Senile Dementia
[description not available]		02.2510
Alzheimer Disease
A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)		02.2510