loline: RN given from CAS Index Guide (1982-1986), p.1019G [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
loline : A loline alkaloid with formula C8H14N2O. [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]
| ID Source | ID |
|---|---|
| PubMed CID | 716098 |
| CHEBI ID | 156448 |
| SCHEMBL ID | 395725 |
| MeSH ID | M0165440 |
| Synonym |
|---|
| 25161-91-5 |
| loline |
| 2,4-methano-4h-furo(3,2-b)pyrrol-3-amine, hexahydro-n-methyl-, (2r,3r,3as,4s,6as)- |
| festucine |
| 2,4-methano-4h-furo(3,2-b)pyrrole, hexahydro-3-(methylamino)- |
| 2,4-methano-4h-furo(3,2-b)pyrrol-3-amine, hexahydro-n-methyl-, (2r-(2-alpha,3-alpha,3a-beta,4-alpha,6a-beta))- |
| CHEBI:156448 |
| lolina |
| (1s,6r,7r,7as)-n-methylhexahydro-1h-1,6-epoxypyrrolizin-7-amine |
| AKOS006278760 |
| unii-ic997t2wz9 |
| ic997t2wz9 , |
| loline [mi] |
| methyl-n-depropionyldecorticasine |
| (+)-loline |
| (2r,3r,3as,4s,6as)-hexahydro-n-methyl-2,4-methano-4h-furo(3,2-b)pyrrol-3-amine |
| SCHEMBL395725 |
| (2r,3r,3as,4s,6as)-hexahydro-n-methyl-2,4-methano-4h-furo[3,2-b]pyrrol-3-amine |
| (1r,3s,7s,8r)-n-methyl-2-oxa-6-azatricyclo[4.2.1.0,3,7]nonan-8-amine |
| Q27280662 |
| XL175852 |
| (1r,3s,7s,8r)-n-methyl-2-oxa-6-azatricyclo[4.2.1.0?,?]nonan-8-amine |
| (1r,3s,7s,8r)-n-methyl-2-oxa-6-azatricyclo[4.2.1.03,7]nonan-8-amine |
Loline (1) is a small alkaloid that, in spite of its simple-looking structure, has posed surprising challenges to synthetic chemists. The lolines are a class of bioprotective alkaloids that are produced by Epichloë species.
| Excerpt | Reference | Relevance |
|---|---|---|
| "The lolines are a class of bioprotective alkaloids that are produced by Epichloë species, fungal endophytes of grasses. " | ( Enzymes from fungal and plant origin required for chemical diversification of insecticidal loline alkaloids in grass-Epichloë symbiota. Bhardwaj, M; Grossman, RB; Nagabhyru, P; Pan, J; Schardl, CL, 2014) | 1.18 |
| "Loline (1) is a small alkaloid that, in spite of its simple-looking structure, has posed surprising challenges to synthetic chemists. " | ( An efficient synthesis of loline alkaloids. Cakmak, M; Mayer, P; Trauner, D, 2011) | 2.11 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "The loline alkaloids have been identified as possible target metabolites as they are associated with potent effects on insects and low toxicity to grazing animals." | ( Short-term toxicity studies of loline alkaloids in mice. Finch, SC; Kerby, JW; Munday, JS; Munday, R, 2016) | 1.2 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "The loline treatment caused no statistically significant effect on gross pathology, histology, haematology, blood chemistry, heart rate, blood pressure or motor coordination." | ( Short-term toxicity studies of loline alkaloids in mice. Finch, SC; Kerby, JW; Munday, JS; Munday, R, 2016) | 1.2 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " The success of this approach is dependent on the selection of an appropriate secondary metabolite target which must not only be effective against insect pests but also be safe for grazing and monogastric animals." | ( Short-term toxicity studies of loline alkaloids in mice. Finch, SC; Kerby, JW; Munday, JS; Munday, R, 2016) | 0.72 |
The total quantity of lolines excreted in both urine and faeces was 10% and 4% of the amount dosed in Experiments 1 and 2, respectively.
| Excerpt | Relevance | Reference |
|---|---|---|
| "To determine the effect of oral dosing of sheep with loline alkaloids on their excretion in urine and faeces, and to monitor for any toxic effects." | ( Excretion of loline alkaloids in urine and faeces of sheep dosed with meadow fescue (Festuca pratensis) seed containing high concentrations of loline alkaloids. Fletcher, LR; Gooneratne, SR; Patchett, BJ; Wellby, M, 2012) | 1 |
| " The total quantity of lolines excreted in both urine and faeces was 10% and 4% of the amount dosed in Experiments 1 and 2, respectively." | ( Excretion of loline alkaloids in urine and faeces of sheep dosed with meadow fescue (Festuca pratensis) seed containing high concentrations of loline alkaloids. Fletcher, LR; Gooneratne, SR; Patchett, BJ; Wellby, M, 2012) | 1.06 |
| Class | Description |
|---|---|
| secondary amino compound | A compound formally derived from ammonia by replacing two hydrogen atoms by organyl groups. |
| loline alkaloid | A pyrrolizidine alkaloid that is hexahydro-1H-pyrrolizine carrying an exo-1-amino group at position 1 and an ether bridge between C-2 and C-7. It is a class of natural insecticides produced by fungal symbionts of Poaceae. |
| [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] | |
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 1 (2.17) | 18.7374 |
| 1990's | 8 (17.39) | 18.2507 |
| 2000's | 17 (36.96) | 29.6817 |
| 2010's | 17 (36.96) | 24.3611 |
| 2020's | 3 (6.52) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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 strong demand-to-supply ratio for research on this compound.
| This Compound (38.80) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 3 (6.25%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 45 (93.75%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||