Page last updated: 2024-12-07
lupanine
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]
| Flora | Rank | Flora Definition | Family | Family Definition |
|---|
| Lupinus | genus | A plant genus of the family FABACEAE that is a source of SPARTEINE, lupanine and other lupin alkaloids.[MeSH] | Fabaceae | The 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 exaltatus | species | [no description available] | Fabaceae | The 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 Source | ID |
|---|
| PubMed CID | 91471 |
| CHEMBL ID | 459396 |
| CHEBI ID | 28193 |
| SCHEMBL ID | 564463 |
| MeSH ID | M0052022 |
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.
| Excerpt | Reference | Relevance |
|---|
| "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 |
Drug Classes (3)
| Class | Description |
|---|
| quinolizidine alkaloid | |
| tertiary amine | A compound formally derived from ammonia by replacing three hydrogen atoms by hydrocarbyl groups. |
| delta-lactam | A 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] |
Research
Studies (34)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|
| pre-1990 | 11 (32.35) | 18.7374 |
| 1990's | 8 (23.53) | 18.2507 |
| 2000's | 6 (17.65) | 29.6817 |
| 2010's | 7 (20.59) | 24.3611 |
| 2020's | 2 (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.
| Metric | This Compound (vs All) |
|---|
| Research Demand Index | 30.57 (24.57) | | Research Supply Index | 3.69 (2.92) | | Research Growth Index | 4.59 (4.65) | | Search Engine Demand Index | 39.34 (26.88) | | Search Engine Supply Index | 2.00 (0.95) |
| |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 2 (5.13%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 37 (94.87%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |