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Solasonine

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Solasonine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ECHA InfoCard 100.038.917 Edit this at Wikidata
UNII
  • Key: QCTMYNGDIBTNSK-XEAAVONHSA-N
  • 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
C45H73NO16
Molar mass 884.070 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

Anticancer Potential

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Solasonine is one of the main components in the plant Solanum nigrum Linn.. The plant has been used in traditional Chinese medicine due to its anti-inflammatory and anti-viral properties. Recent studies highlight the effects of solasonine and its anticancer potential by the suppression of tumor growth, inducing apoptosis, and activating ferroptosis.[3][4]

Solasonine enhances anticancer potential by inducing apoptosis, or programmed cell death, through the regulation of key pathways, such as the mitochondrial membrane permeability.[3] Ferroptosis, a process that promotes cancer cell death, can be activated with solasonine by increasing and catalyzing reactive oxygen species (ROS) production.[4]

Side Effects

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Although, solasonine has anti-infection properties it has many adverse side effects as a steroidal glycoalkaloid.[5] These side effects include low blood pressure, a decrease in respiratory activity, rapid heart beat etc.[5] These side effects are the direct result of the cytotoxic properties of solasonine (at high levels) that lead to disrupted cell membranes. Not only do high doses of solasonine disrupt cellular DNA synthesis, but they also suggest the presence of genotoxic and mutagenic effects.[3] Toxic symptoms such as headache, gastrointestinal irritation, vomiting, diarrhea, etc. can be the result of an overdose on Solanum nigrum Linn..[6]

See also

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References

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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.
  3. ^ a b c Pei, Hongyu; Yang, Jing; Li, Wang; Luo, Xing; Xu, Yi; Sun, Xueying; Chen, Qian; Zhao, Qi; Hou, Li; Tan, Gang; Ji, Daolin (2023-09-29). "Solanum nigrum Linn.: Advances in anti-cancer activity and mechanism in digestive system tumors". Medical Oncology. 40 (11): 311. doi:10.1007/s12032-023-02167-7. ISSN 1559-131X. PMID 37775552.
  4. ^ a b Liang, Xiaoqiang; Hu, Cheng; Han, Mian; Liu, Congying; Sun, Xun; Yu, Kui; Gu, Honggang; Zhang, Jingzhe (2022-04-12). "Solasonine Inhibits Pancreatic Cancer Progression With Involvement of Ferroptosis Induction". Frontiers in Oncology. 12. doi:10.3389/fonc.2022.834729. ISSN 2234-943X. PMC 9039314. PMID 35494004.
  5. ^ 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.
  6. ^ Wang, YingZheng; Wang, Tong; Liu, WeiDong; Luo, GuangZhi; Lu, GuangYing; Zhang, YaNan; Wang, HuaXin (2024-02-01). "Anticancer effects of solasonine: Evidence and possible mechanisms". Biomedicine & Pharmacotherapy. 171: 116146. doi:10.1016/j.biopha.2024.116146. ISSN 0753-3322.
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