Epilupinine
| Names | |
|---|---|
| IUPAC name
[(1S,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]methanol
| |
Other names
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C10H19NO | |
| Molar mass | 169.26 |
| Hazards | |
| GHS labelling: | |
| Warning | |
| H302, H303 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
| |
Epilupinine is a naturally occurring quinolizidine alkaloid. Epilupinine serves as a key model compound in the study of quinolizidine biosynthesis, chemical ecology, and asymmetric synthesis.
Structure
It is the C-1 epimer of the more common alkaloid lupinine. It is a stereoisomer of a fundamental lupin alkaloid. It possesses a fused bicyclic structure comprising a piperidine and a pyridine ring, with a hydroxymethyl group at the ring junction.
Epilupinins and lupinine themselves are the simplest of a large group of alkaloid metabolites from legumes (Fabaceae).
biological sources
Natural occurrence of epilupinine in the Fabaceae family, epilupinine was found in Maackia tenuifolia[1], Virgilia oroboides[2], Thinicola incana [3], Retama sphaerocarpa[1], in other representatives of the genus Maackia, Lamprolobium[4], Anarthrophyllum, Plagiocarpus[5], it was discovered as a new one in the genus Calpurnia, in the species Calpurnia aurea[6].
The highest and most widespread content of epilupinine is found in the genus Lupinus, with the highest content occurring in Lupinus luteus[7].
Synthesis and biosynthesis
It was first isolated from various species within the plant genus Lupinus (lupins). They were synthesized via an intermediate enaminone.[8][1]
Asymmetric total synthesis (Enantioselective synthesis) of (+)-. So far, 17 asymmetric total syntheses of epilupinine. The total synthesis involved alkylations of N-nosylamide, ozone oxidation, and sequential reactions of the removal of the nosyl group, intramolecular dehydrative condensation, intramolecular Mannich reaction catalyzed by l-proline, and a reduction.[9]
The biosynthetic pathway of 1 is proposed to begin with the dimerization of l-lysine to dialdehyde. The intramolecular dehydrative condensation leading to iminium cation followed by an intramolecular Mannich reaction forms aldehyde. Finally, the aldehyde is reduced.[10]
Dementia models
Studies have reported that 1-epilupinine may have therapeutic potential for improving cognitive function and neuroprotection.
To improve dementia symptoms and neuroinflammation in a mouse model of scopolamine-induced dementia, a model was created using scopolamine hydrobromide, with donepezil used as a positive control. After five days of treatment, cognitive function was assessed using the Morris water maze test. An inflammatory marker array was used to measure inflammatory markers in the prefrontal cortex. The Morris water maze test revealed that the model group receiving scopolamine hydrobromide (1 mg/kg) demonstrated significantly fewer platform crossings and longer latencies (P < 0.001), while mice treated with epilupinine at a dose of (5 mg/kg) demonstrated improved performance, a higher number of crossings and reduced latency (P < 0.01).[11]
References
- ^ a b c Epilupinine from PubChem
- ^ Veen, Gerhard; Greinwald, Roland; Witte, Ludger; Wray, Victor; Czygan, Franz-Christian (1991-01-01). "Alkaloids of Virgilia divaricata and V. oroboides". Phytochemistry. 30 (6): 1891–1895. doi:10.1016/0031-9422(91)85034-W. ISSN 0031-9422.
- ^ Greinwald, Roland; Ross, James H.; Witte, Ludger; Czygan, F. -C. (1996-07-01). "Alkaloids of Templetonia incana". Biochemical Systematics and Ecology. 24 (5): 423–426. doi:10.1016/0305-1978(96)00024-5. ISSN 0305-1978.
- ^ Greinwald, Roland; Ross, James H.; Witte, Ludger; Czygan, F. -C. (1993-04-01). "A survey of alkaloids in the genus Lamprolobium Benth. (Fabaceae: Brongniartieae)". Biochemical Systematics and Ecology. 21 (3): 405–411. doi:10.1016/0305-1978(93)90032-M. ISSN 0305-1978.
- ^ Greinwald, Roland; Ross, James H.; Witte, Ludger; Czygan, F. -C. (1995-09-01). "The alkaloid pattern of Plagiocarpus axillaris (Fabaceae: Brongniartieae)". Biochemical Systematics and Ecology. 23 (6): 645–648. doi:10.1016/0305-1978(95)00059-3. ISSN 0305-1978.
- ^ Asres, Kaleab; Gibbons, William A.; Phillipson, J. David; Mascagni, Paolo (1986-05-22). "Alkaloids of ethiopian Calpurnia aurea subsp. aurea". Phytochemistry. 25 (6): 1443–1447. doi:10.1016/S0031-9422(00)81306-0. ISSN 0031-9422.
- ^ Czepiel, Katarzyna; Kroc, Magdalena; Burdzińska, Aleksandra; Krajewski, Paweł; Barzyk, Paweł; Święcicki, Wojciech (2023-11-01). "Evaluation of alkaloids in yellow lupin (Lupinus luteus L.): New insight to genetic resources diversity and future breeding perspectives". Scientia Horticulturae. 321 112279. doi:10.1016/j.scienta.2023.112279. ISSN 0304-4238.
- ^ Hussaini, Syed Raziullah; Chamala, Raghu Ram; Wang, Zhiguo (September 2015). "The Eschenmoser sulfide contraction method and its application in the synthesis of natural products". Tetrahedron. 71 (36): 6017–6086. doi:10.1016/j.tet.2015.06.026.
- ^ Tsutsumi, Tomohiro; Karanjit, Sangita; Nakayama, Atsushi; Namba, Kosuke (19 April 2019). "A Concise Asymmetric Total Synthesis of (+)-Epilupinine". Organic Letters. 21 (8): 2620–2624. doi:10.1021/acs.orglett.9b00607. PMID 30963767.
- ^ Tsutsumi, Tomohiro; Namba, Kosuke (5 August 2020). "Total Synthesis of Epilupinine: Synthetic Strategy of Fused Bicyclic Skeleton Containing Nitrogen". Chemistry Letters. 49 (8): 963–969. doi:10.1246/cl.200340.
- ^ Zhang, Chenhui; Xu, Jiyi; Xu, Fang; Xie, Xiaomeng; Ji, Tengfei; Wang, Chuanyue; Du, Jing (March 2025). "1-Epilupinine enhances cognition and reduces inflammation in scopolamine-induced dementia model mice". Neuroscience Letters. 852 138184. doi:10.1016/j.neulet.2025.138184. PMID 40057172.