U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C45H73NO15
Molecular Weight 868.0588
Optical Activity UNSPECIFIED
Defined Stereocenters 26 / 26
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .ALPHA.-SOLANINE

SMILES

C[C@@H]1[C@H]2CC[C@H](C)CN2[C@H]3C[C@H]4[C@@H]5CC=C6C[C@H](CC[C@]6(C)[C@H]5CC[C@]4(C)[C@@H]13)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

InChI

InChIKey=ZGVSETXHNHBTRK-OTYSSXIJSA-N
InChI=1S/C45H73NO15/c1-19-6-9-27-20(2)31-28(46(27)16-19)15-26-24-8-7-22-14-23(10-12-44(22,4)25(24)11-13-45(26,31)5)57-43-40(61-41-37(54)35(52)32(49)21(3)56-41)39(34(51)30(18-48)59-43)60-42-38(55)36(53)33(50)29(17-47)58-42/h7,19-21,23-43,47-55H,6,8-18H2,1-5H3/t19-,20+,21-,23-,24+,25-,26-,27+,28-,29+,30+,31-,32-,33+,34-,35+,36-,37+,38+,39-,40+,41+,42-,43+,44-,45-/m0/s1

HIDE SMILES / InChI

Description

alpha-Solanine, a naturally occurring steroidal glycoalkaloid in potato sprouts, was found to possess anti-carcinogenic properties, such as inhibiting proliferation and inducing apoptosis of tumor cells. Human intake of high doses of alpha-Solanine has led to acute intoxication, in severe cases coma and death. The ratio of a-solanine to a-chaconine may determine the degree and nature of the glycoalkaloid toxicity in potatoes, as the toxicity of the two alkaloids act synergistically. alpha-Solanine can inhibit cholinesterase, disrupt cell membranes, and cause birth defects. Some studies suggests that the toxic mechanism of solanine is caused by the chemical's interaction with mitochondrial membranes. Experiments show that solanine exposure opens the potassium channels of mitochondria, decreasing their membrane potential. This, in turn, leads to K+ being transported from the mitochondria into the cytoplasm, and this increased concentration of K+ in the cytoplasm triggers cell damage and apoptosis.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.17 µM [IC50]
14.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Administration of solanine to nude mice inhibited xenograft growth of PANC-1 tumor. 1 ul/g (weight of mice) solanine was injected into the abdominal cavity of each mouse. The concentration of solanine is 5 ug/ml. Solanine had a remarkable safety at the dose of 5 ug/g(weight of mice).
Route of Administration: Other
In Vitro Use Guide
Incubation of cells with α-solanine for 48 h resulted in reduction in viability with IC50 values ~ 10 uM in all cancer cell lines. A549 cells treated with 10 uM α-solanine for 24 h showed abundant autophagosomes, amphisomes and autolysosomes in various stages of maturation.