Solasonine

Solasonine
Identifiers
CAS Number	19121-58-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:9191;
ChEMBL	ChEMBL438956;
ECHA InfoCard	100.038.917
PubChem CID	119247;
UNII	TR60638HXL ;
CompTox Dashboard (EPA)	DTXSID801028790 ;
	InChI Key: QCTMYNGDIBTNSK-XEAAVONHSA-N;
	SMILES C[C@@H]1CC[C@@]2(NC1)O[C@H]3C[C@H]4[C@@H]5CC=C6C[C@H](CC[C@]6(C)[C@H]5CC[C@]4(C)[C@H]3[C@@H]2C)O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]9O[C@@H](C)[C@H](O)[C@@H](O)[C@H]9O;
Properties
Chemical formula	C; 45H; 73NO; 16
Molar mass	884.07 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Solasonine is a glycoalkaloid that is found in Solanum plants of the family Solanaceae.^[1] Solasonine is a poisonous chemical compound when used at high levels. It is a glycoside of solasodine. Glycoalkaloids such as Solasonine have various applications including pharmacology, cancer treatments and even a role as a pesticide.

High levels of glycoalkaloids are toxic to humans due to their ability to disrupt cell-membrane function.^[2] There is a loss of membrane integrity which puts the cell at risk for apoptosis (cell death) due to the ability of any chemical coming into contact with the cell.

Solasonine was one component of the unsuccessful experimental cancer drug candidate Coramsine.

Side Effects

Although, solasonine has anti-infection properties it has many adverse side effects as a steroidal glycoalkaloid.^[3] These side effects include low blood pressure, a decrease in respiratory activity, rapid heart beat etc.^[3] These side effects are the direct result of the cytotoxic properties of solasonine (at high levels) that lead to disrupted cell membranes.

References

^ Everist, S.L. (1981). Poisonous Plants of Australia. Angus & Robertson. ISBN 0-207-14228-9.
^ Al Sinani, S.S.S.; Eltayeb, E.A. (September 2017). "The steroidal glycoalkaloids solamargine and solasonine in Solanum plants". South African Journal of Botany. 112: 253–269. doi:10.1016/j.sajb.2017.06.002. ISSN 0254-6299.
^ ^a ^b Yang, Jun; Huang, Wenjing; Tan, Wenfu (2016). "Solasonine, A Natural Glycoalkaloid Compound, Inhibits Gli-Mediated Transcriptional Activity". Molecules. 21 (10): 1364. doi:10.3390/molecules21101364. PMC 6274431. PMID 27754442.

External links

Media related to Solasonine at Wikimedia Commons

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[1] Everist, S.L. (1981). Poisonous Plants of Australia. Angus & Robertson. ISBN 0-207-14228-9.

[2] Al Sinani, S.S.S.; Eltayeb, E.A. (September 2017). "The steroidal glycoalkaloids solamargine and solasonine in Solanum plants". South African Journal of Botany. 112: 253–269. doi:10.1016/j.sajb.2017.06.002. ISSN 0254-6299.

[:12-3] Yang, Jun; Huang, Wenjing; Tan, Wenfu (2016). "Solasonine, A Natural Glycoalkaloid Compound, Inhibits Gli-Mediated Transcriptional Activity". Molecules. 21 (10): 1364. doi:10.3390/molecules21101364. PMC 6274431. PMID 27754442.

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Solasonine

Contents

Side Effects

See also

References

External links

Identifiers

CAS Number	19121-58-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:9191
ChEMBL	ChEMBL438956
ECHA InfoCard	100.038.917
PubChem CID	119247
UNII	TR60638HXL^Y
CompTox Dashboard (EPA)	DTXSID801028790
InChI Key: QCTMYNGDIBTNSK-XEAAVONHSA-N
SMILES C[C@@H]1CC[C@@]2(NC1)O[C@H]3C[C@H]4[C@@H]5CC=C6C[C@H](CC[C@]6(C)[C@H]5CC[C@]4(C)[C@H]3[C@@H]2C)O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]9O[C@@H](C)[C@H](O)[C@@H](O)[C@H]9O
Properties
Chemical formula	C ₄₅H ₇₃NO ₁₆
Molar mass	884.07 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references