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
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/26313911 | https://www.ncbi.nlm.nih.gov/pubmed/24051269 | https://www.ncbi.nlm.nih.gov/pubmed/10910502https://www.ncbi.nlm.nih.gov/pubmed/20930376Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27588073 | https://www.ncbi.nlm.nih.gov/pubmed/23062825 | https://www.ncbi.nlm.nih.gov/pubmed/19217925
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26313911 | https://www.ncbi.nlm.nih.gov/pubmed/24051269 | https://www.ncbi.nlm.nih.gov/pubmed/10910502https://www.ncbi.nlm.nih.gov/pubmed/20930376
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27588073 | https://www.ncbi.nlm.nih.gov/pubmed/23062825 | https://www.ncbi.nlm.nih.gov/pubmed/19217925
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.
Originator
Sources: https://books.google.ru/books?id=d42RCwAAQBAJ&pg=PA39&lpg=PA39&dq=a-SOLANINE retrieved from Edible Medicinal and Non-Medicinal Plants Volume 12 Modified Stems, Roots, Bulbs Authors: Lim, T. K., p. 39Chemische Berichte Volume 88 Pages1492-1507 Journal 1955
Curator's Comment: Solanine was first reported in potato by Baup (1826)
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1914 |
0.17 µM [IC50] | ||
Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10910502 |
14.0 µM [IC50] | ||
Target ID: CHEMBL5763 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23062825 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inhibitory effect of α-solanine on esophageal carcinoma in vitro. | 2016-09 |
|
| α-Solanine induces ROS-mediated autophagy through activation of endoplasmic reticulum stress and inhibition of Akt/mTOR pathway. | 2015-08-27 |
|
| The protective and therapeutic effects of alpha-solanine on mice breast cancer. | 2013-10-15 |
|
| A 28-day repeat dose toxicity study of steroidal glycoalkaloids, alpha-solanine and alpha-chaconine in the Syrian Golden hamster. | 2009-06 |
|
| Cholinesterase inhibition by potato glycoalkaloids slows mivacurium metabolism. | 2000-08 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24505326
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26313911
Curator's Comment: In vitro anti-proliferative activity of
α-solanine by sulforhodamine B (SRB) assay on
a panel of human cancer cell lines comprising A549, MCF-7,
DU145 and KB was assessed.
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.
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SUBSTANCE RECORD