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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

Molecular Formula C45H73NO15
Molecular Weight 868.0588
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 26 / 26
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
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
Patents

Sample Use Guides

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
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:35:32 GMT 2025
Edited
by admin
on Mon Mar 31 18:35:32 GMT 2025
Record UNII
15XXN7Q45T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
.ALPHA.-SOLANINE [MI]
Preferred Name English
.ALPHA.-SOLANINE
MI  
Common Name English
.BETA.-D-GALACTOPYRANOSIDE, (3.BETA.)-SOLANID-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(.BETA.-D-GLUCOPYRANOSYL-(1->3))-
Common Name English
SOLANINE [HSDB]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
243-879-8
Created by admin on Mon Mar 31 18:35:32 GMT 2025 , Edited by admin on Mon Mar 31 18:35:32 GMT 2025
PRIMARY
CAS
20562-02-1
Created by admin on Mon Mar 31 18:35:32 GMT 2025 , Edited by admin on Mon Mar 31 18:35:32 GMT 2025
PRIMARY
EPA CompTox
DTXSID9030707
Created by admin on Mon Mar 31 18:35:32 GMT 2025 , Edited by admin on Mon Mar 31 18:35:32 GMT 2025
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MERCK INDEX
m10102
Created by admin on Mon Mar 31 18:35:32 GMT 2025 , Edited by admin on Mon Mar 31 18:35:32 GMT 2025
PRIMARY Merck Index
HSDB
3539
Created by admin on Mon Mar 31 18:35:32 GMT 2025 , Edited by admin on Mon Mar 31 18:35:32 GMT 2025
PRIMARY
PUBCHEM
30185
Created by admin on Mon Mar 31 18:35:32 GMT 2025 , Edited by admin on Mon Mar 31 18:35:32 GMT 2025
PRIMARY
FDA UNII
15XXN7Q45T
Created by admin on Mon Mar 31 18:35:32 GMT 2025 , Edited by admin on Mon Mar 31 18:35:32 GMT 2025
PRIMARY