Compounds > lupanine
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lupanine

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

Description

Lupanine is a quinolizidine alkaloid found in various species of lupin plants, particularly Lupinus luteus. It exhibits a wide range of biological activities, including insecticidal, antimicrobial, and anti-inflammatory properties. Its synthesis is complex and involves several steps, including cyclization reactions and reduction. The compound's importance lies in its potential applications in medicine, agriculture, and other fields. Researchers study lupanine to understand its mechanisms of action, explore its potential therapeutic benefits, and develop new agrochemicals for pest control. Lupanine is also being investigated for its potential role in plant defense mechanisms and its effects on the environment.'

lupanine: formed by coupling of lupinine with pyridine; lupinine is also available; RN given refers to parent cpd(7S-(7alpha,7abeta,14alpha,14aalpha))-isomer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

lupanine : The delta-lactam obtained by formal oxidation at the 2-position of sparteine. The major alkaloid from the seeds of Lupinus exaltatus, L. mexicanus and L. rotundiflorus, it is among the most important of the tetracyclic quinolizidine alkaloids. [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
LupinusgenusA plant genus of the family FABACEAE that is a source of SPARTEINE, lupanine and other lupin alkaloids.[MeSH]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]
Lupinus exaltatusspecies[no description available]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]

Cross-References

ID SourceID
PubMed CID91471
CHEMBL ID459396
CHEBI ID28193
SCHEMBL ID564463
MeSH IDM0052022

Synonyms (39)

Synonym
(7alpha,7aalpha,14alpha,14abeta)-dodecahydro-7,14-methano-2h,11h-dipyridol[1,2-a:1',2'-e][1,5]diazocin-11-one
chebi:28193 ,
(+)-2-oxosparteine
lupanin
2-oxosparteine
lupanine d-form
d-lupanine
lupanine, d-
550-90-3
lupanine
(+)-lupanine
spartein-2-one
CHEMBL459396
unii-183ku7535a
183ku7535a ,
9k48888n9p ,
4356-43-8
unii-9k48888n9p
lupanine, (+/-)-
7,14-methano-2h,11h-dipyrido(1,2-a:1',2'-e)(1,5)diazocin-11-one, dodecahydro-, (7r,7as,14r,14ar)-rel-
lupanine dl-form [mi]
(+/-)-lupanine
(+/-)-2-oxosparteine
dl-lupanine
(rac)-2-oxosparteine
SCHEMBL564463
7,14-methano-2h,11h-dipyrido(1,2-a:1',2'-e)(1,5)diazocin-11-one, dodecahydro-, (7s,7ar,14s,14as)-
lupanine, (+)-
lupanine d-form [mi]
JYIJIIVLEOETIQ-XDQVBPFNSA-N
(1s,2r,9s,10s)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecan-6-one
Q27103558
AT20203
(1s,2r,9s,10s)-7,15-diazatetracyclo[7.7.1.0?,?.0??,??]heptadecan-6-one
DTXSID001023908
HY-N3359
CS-0023989
(7alpha,7aalpha,14alpha,14abeta)-dodecahydro-7,14-methano-2h,11h-dipyridol(1,2-a:1',2'-e)(1,5)diazocin-11-one
AKOS040760061

Research Excerpts

Overview

Lupanine is an alkaloid used in the pharma industry as a building block or precursor in the synthesis of sparteine. Lupanine could be used for semi-synthesis of various novel high added-value compounds.

ExcerptReferenceRelevance
"Lupanine is an alkaloid used in the pharma industry as a building block or precursor in the synthesis of sparteine and also explored for drug synthesis in the pharma industry as a chiral selector. "( Greener Strategy for Lupanine Purification from Lupin Bean Wastewaters Using a Molecularly Imprinted Polymer.
Afonso, CAM; Andrade, KHS; Esteves, T; Ferreira, FA; Ferreira, FC; Gil, A; Mota, AT; Sánchez-González, Á, 2022)		2.48
"Lupanine is a plant toxin contained in the wastewater of lupine bean processing industries, which could be used for semi-synthesis of various novel high added-value compounds. "( Resolution of alkaloid racemate: a novel microbial approach for the production of enantiopure lupanine via industrial wastewater valorization.
Afonso, CAM; Drouza, C; Ferreira, FC; Gonçalves, JMJ; Hadjiadamou, I; Koutinas, M; Parmaki, S; Tsipa, A; Vasquez, MI, 2020)		2.22
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
quinolizidine alkaloid
tertiary amineA compound formally derived from ammonia by replacing three hydrogen atoms by hydrocarbyl groups.
delta-lactamA lactam in which the amide bond is contained within a six-membered ring, which includes the amide nitrogen and the carbonyl carbon.
[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 (2)

Assay IDTitleYearJournalArticle
AID337605Displacement of [3H]quinuclidinyl benzilate from muscarinic ACh receptor1994Journal of natural products, Sep, Volume: 57, Issue:9
Binding of quinolizidine alkaloids to nicotinic and muscarinic acetylcholine receptors.
AID337604Displacement of [3H]nicotin from nicotinic ACh receptor1994Journal of natural products, Sep, Volume: 57, Issue:9
Binding of quinolizidine alkaloids to nicotinic and muscarinic acetylcholine receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (34)

TimeframeStudies, This Drug (%)All Drugs %
pre-199011 (32.35)18.7374
1990's8 (23.53)18.2507
2000's6 (17.65)29.6817
2010's7 (20.59)24.3611
2020's2 (5.88)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.57

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 Index30.57 (24.57)
Research Supply Index3.69 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index39.34 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (30.57)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies2 (5.13%)4.05%
Observational0 (0.00%)0.25%
Other37 (94.87%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
disulfiram
[no description available]		1.9710organic disulfide;
organosulfur acaricide		angiogenesis inhibitor;
antineoplastic agent;
apoptosis inducer;
EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor;
EC 3.1.1.1 (carboxylesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
ferroptosis inducer;
fungicide;
NF-kappaB inhibitor
phenobarbital
Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.		1.9710barbituratesanticonvulsant;
drug allergen;
excitatory amino acid antagonist;
sedative
lysine
Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.		6.9310aspartate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
lysine;
organic molecular entity;
proteinogenic amino acid		algal metabolite;
anticonvulsant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
arginine
Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.		2.1110arginine;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		biomarker;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical
sparteine, (7r-(7alpha,7aalpha,14alpha,14abeta))-isomer
[no description available]		1.9810
cytisine
[no description available]		1.9810alkaloid;
bridged compound;
lactam;
organic heterotricyclic compound;
secondary amino compound		nicotinic acetylcholine receptor agonist;
phytotoxin;
plant metabolite
anagyrine
anagyrine: RN given refers to (7R-(7alpha,7abeta,14alpha))-isomer; structure		2.4620alkaloid
lupinine
lupinine: RN given refers to parent cpd(1R-trans)-isomer; structure		1.9810quinolizidine alkaloid
stachyose
stachyose: RN given refers to parent cpd. stachyose : A tetrasaccharide consisting of sucrose having an alpha-D-galactosyl-(1->6)-alpha-D-galactosyl moiety attached at the 6-position of the glucose.		1.9910raffinose family oligosaccharide;
tetrasaccharide		mouse metabolite;
plant metabolite
quinidine
Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.		1.9910cinchona alkaloidalpha-adrenergic antagonist;
anti-arrhythmia drug;
antimalarial;
drug allergen;
EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor;
EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor;
muscarinic antagonist;
P450 inhibitor;
potassium channel blocker;
sodium channel blocker
ammodendrine
ammodendrine: structure given in first source; RN given refers to (R)-isomer. ammodendrine : A piperidine alkaloid that is piperidine substituted by a 1-acetyl-1,4,5,6-tetrahydropyridin-3-yl group at position 2 (the 2R-stereoisomer).		2.1310acetamides;
N-acylpiperidine;
piperidine alkaloid		plant metabolite;
teratogenic agent
thermospine
thermospine: structure given in first source		6.9710
ajmaline
Ajmaline: An alkaloid found in the root of RAUWOLFIA SERPENTINA, among other plant sources. It is a class 1-A antiarrhythmic agent that apparently acts by changing the shape and threshold of cardiac action potentials.. ajmaline : A monoterpenoid indole alkaloid that consists of ajmalan substituted at positions 17 and 21 by hydroxy groups.		1.9910
beta-escin
[no description available]		1.9910
acebutolol
alpha-D-glucosyl-(1->4)-alpha-D-mannose : An alpha-D-glucosyl-(1->4)-D-mannopyranose in which the anomeric hydroxy group has alpha configuration.		1.9910alpha-D-glucosyl-(1->4)-D-mannopyranose
tannins
Tannins: Polyphenolic compounds with molecular weights of around 500-3000 daltons and containing enough hydroxyl groups (1-2 per 100 MW) for effective cross linking of other compounds (ASTRINGENTS). The two main types are HYDROLYZABLE TANNINS and CONDENSED TANNINS. Historically, the term has applied to many compounds and plant extracts able to render skin COLLAGEN impervious to degradation. The word tannin derives from the Celtic word for OAK TREE which was used for leather processing.		1.9910
piperidines
Piperidines: A family of hexahydropyridines.		2.1310
maltodextrin
maltodextrin : A dextrin in which the D-glucose units are linked by alpha-(1->4) glycosidic bonds.		1.9910
ConditionIndicatedRelationship StrengthStudiesTrials
Teratogenesis
The formation of CONGENITAL ABNORMALITIES.		02.1510
Bovine Diseases
[description not available]		02.1510
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.1510
Alloxan Diabetes
[description not available]		02.4720
Amyoplasia Congenita
[description not available]		02.0210
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		01.9910
Experimental Neoplasms
[description not available]		01.9910
Acute Disease
Disease having a short and relatively severe course.		01.9710
Plant Poisoning
Poisoning by the ingestion of plants or its leaves, berries, roots or stalks. The manifestations in both humans and animals vary in severity from mild to life threatening. In animals, especially domestic animals, it is usually the result of ingesting moldy or fermented forage.		01.9710