Solasonine

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(Redirected from Solasodamine)

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Solasonine
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Identifiers
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3D model (JSmol)
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  • InChI=1S/C45H73NO16/c1-19-8-13-45(46-16-19)20(2)30-27(62-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)57-42-39(61-40-36(54)34(52)31(49)21(3)56-40)38(33(51)29(18-48)59-42)60-41-37(55)35(53)32(50)28(17-47)58-41/h6,19-21,23-42,46-55H,7-18H2,1-5H3/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-/m1/s1
  • 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
Hazards
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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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

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

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

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.Everist, S.L. (1981). Poisonous Plants of Australia. Angus & Robertson. ISBN 0-207-14228-9.
  2. ^ Page Module:Citation/CS1/styles.css has no content.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. Bibcode:2017SAJB..112..253A. doi:10.1016/j.sajb.2017.06.002. ISSN 0254-6299.
  3. ^ a b c Page Module:Citation/CS1/styles.css has no content.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 Page Module:Citation/CS1/styles.css has no content.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 834729. doi:10.3389/fonc.2022.834729. ISSN 2234-943X. PMC 9039314. PMID 35494004.
  5. ^ a b Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. PMID 38198952.
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