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
[H][C@]12CC[C@H](C)CN1[C@@]3([H])C[C@@]4([H])[C@]5([H])CC=C6C[C@H](CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@@]3([H])[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
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
| Molecular Formula | C45H73NO15 |
| Molecular Weight | 868.0588 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 25 / 26 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20930376https://www.ncbi.nlm.nih.gov/pubmed/26313911 | https://www.ncbi.nlm.nih.gov/pubmed/24051269 | https://www.ncbi.nlm.nih.gov/pubmed/10910502Curator'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/20930376https://www.ncbi.nlm.nih.gov/pubmed/26313911 | https://www.ncbi.nlm.nih.gov/pubmed/24051269 | https://www.ncbi.nlm.nih.gov/pubmed/10910502
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
α-Solanine is a glycoalkaloid found in species of the nightshade family including potato. The name is derived from the Latin for European black nightshade (Solanum nigrum), from which solanine was first isolated in 1820. It was primarily reported to have toxic effects in humans. However, there is a growing body of literature demonstrating in vitro and in vivo anticancer activity of α-solanine. Most of these studies have shown activation of apoptosis as the underlying mechanism in antitumor activity of α-solanine. Naturally occurring BuChE and AChE inhibitor.
Originator
Sources: Chemische Berichte Volume 88 Pages1492-1507 Journal 1955https://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. 39
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 |
14.0 µM [IC50] | ||
Target ID: CHEMBL5763 |
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 |
|---|---|---|
| Cholinesterase inhibition by potato glycoalkaloids slows mivacurium metabolism. | 2000 Aug |
|
| A 28-day repeat dose toxicity study of steroidal glycoalkaloids, alpha-solanine and alpha-chaconine in the Syrian Golden hamster. | 2009 Jun |
|
| The protective and therapeutic effects of alpha-solanine on mice breast cancer. | 2013 Oct 15 |
|
| α-Solanine induces ROS-mediated autophagy through activation of endoplasmic reticulum stress and inhibition of Akt/mTOR pathway. | 2015 Aug 27 |
|
| Inhibitory effect of α-solanine on esophageal carcinoma in vitro. | 2016 Sep |
Sample Use Guides
The Syrian Golden hamster was given daily doses of a-solanine and a-chaconine by gavage for 28 days. Doses of up to 33.3 mg total glycoalkaloids/ kg body weight were applied in ratios of 1:3.7 and 1:70 (a-solanine:a-chaconine). Administration of the highest doses of both ratios resulted in distended and fluid filled small intestines and stomach. Animals receiving the ratio with the reduced content of a-solanine were less affected compared to those receiving the other ratio.
Route of Administration:
Oral
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.
EC9706 and Eca109 cell lines were exposed to a range of concentrations of α solanine (10, 20, 40 and 60 μg/ml) for 24, 48 and 72 h. Cell proliferation was determined by measuring the absorbance at 450 nm. Compared with the control, (without α solanine), cell proliferation was markedly inhibited at different concen¬trations in the α solanine group in a dose and time dependent manner
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:44:46 GMT 2023
by
admin
on
Fri Dec 15 16:44:46 GMT 2023
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| Record UNII |
15XXN7Q45T
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| Record Status |
Validated (UNII)
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| Record Version |
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