Solasodine is a poisonous alkaloid chemical compound that occurs in plants of the family Solanaceae such as potatoes and tomatoes.[1] Solasonine and solamargine are glycoalkaloid derivatives of solasodine.[1] Solasodine is teratogenic to hamster fetuses in a dose of 1200 to 1600 mg/kg.[2] A 2013 literature survey found that various studies have indicated that solasodine may have diuretic, anticancer, antifungal, cardiotonic, antispermatogenetic, antiandrogenic, immunomodulatory, antipyretic and/or various other effects on central nervous system.[3]
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| Names | |
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| IUPAC name
(22R,25R)-Spirosol-5α-en-3β-ol
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| Systematic IUPAC name
(2S,2′R,4aR,4bS,5′R,6aS,6bR,7S,9aS,10aS,10bS)-4a,5′,6a,7-Tetramethyl-1,2,3,4,4a,4b,5,6,6a,6b,7,9a,10,10a,10b,11-hexadecahydrospiro[naptho[2′,1′:4,5]indeno[2,1-b]furan-8,2′-piperidin]-2-ol | |
| Other names
Purapuridine; Solancarpidine; Solanearpidine; Solanidine-S
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.004.341 |
| EC Number |
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| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C27H43NO2 | |
| Molar mass | 413.646 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Uses
editIt is commercially used as a precursor for the production of complex steroidal compounds such as contraceptive pills, via a 16-DPA intermediate.[1]
See also
editReferences
edit- ^ a b c Everist, S.L. (1981). Poisonous Plants of Australia. Angus & Robertson. ISBN 978-0-207-14228-4.
- ^ Kinghorn, A.D. (2010). "Toxins and Teratogens of the Solanaceae and Liliaceae". Toxic plants. Society for Economic Botany, Columbia University Press. pp. 75–76. ISBN 978-0231515689.
- ^ Patel, Kanika; Singh, Ravi B.; Patel, Dinesh K. (2013). "Medicinal significance, pharmacological activities, and analytical aspects of solasodine: A concise report of current scientific literature". Journal of Acute Disease. 2 (2): 92–98. doi:10.1016/S2221-6189(13)60106-7.
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