Identifiers | |
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3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ECHA InfoCard | 100.038.917 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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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.
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]
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]
A tumor suppressor gene (TSG), or anti-oncogene, is a gene that regulates a cell during cell division and replication. If the cell grows uncontrollably, it will result in cancer. When a tumor suppressor gene is mutated, it results in a loss or reduction in its function. In combination with other genetic mutations, this could allow the cell to grow abnormally. The loss of function for these genes may be even more significant in the development of human cancers, compared to the activation of oncogenes.
Karyorrhexis is the destructive fragmentation of the nucleus of a dying cell whereby its chromatin is distributed irregularly throughout the cytoplasm. It is usually preceded by pyknosis and can occur as a result of either programmed cell death (apoptosis), cellular senescence, or necrosis.
Solanine is a glycoalkaloid poison found in species of the nightshade family within the genus Solanum, such as the potato. It can occur naturally in any part of the plant, including the leaves, fruit, and tubers. Solanine has pesticidal properties, and it is one of the plant's natural defenses. Solanine was first isolated in 1820 from the berries of the European black nightshade, after which it was named. It belongs to the chemical family of saponins.
Bufagin is a toxic steroid C24H34O5 obtained from toad's milk, the poisonous secretion of a skin gland on the back of the neck of a large toad (Rhinella marina, synonym Bufo marinus, the cane toad). The toad produces this secretion when it is injured, scared or provoked. Bufagin resembles chemical substances from digitalis in physiological activity and chemical structure.
Solanum americanum, commonly known as American black nightshade, small-flowered nightshade or glossy nightshade, is a herbaceous flowering plant of wide though uncertain native range. The certain native range encompasses the tropics and subtropics of the Americas, Melanesia, New Guinea, and Australia.
Solanum nigrum, the European black nightshade or simply black nightshade or blackberry nightshade, is a species of flowering plant in the family Solanaceae, native to Eurasia and introduced in the Americas, Australasia, and South Africa. Ripe berries and cooked leaves of edible strains are used as food in some locales, and plant parts are used as a traditional medicine. Some other species may also be referred to as "black nightshade".
Oleocanthal is a phenylethanoid, or a type of natural phenolic compound found in extra-virgin olive oil. It appears to be responsible for the burning sensation that occurs in the back of the throat when consuming such oil. Oleocanthal is a tyrosol ester and its chemical structure is related to oleuropein, also found in olive oil.
Chelerythrine is a benzophenanthridine alkaloid present in the plant Chelidonium majus. It is a potent, selective, and cell-permeable protein kinase C inhibitor in vitro. And an efficacious antagonist of G-protein-coupled CB1 receptors. This molecule also exhibits anticancer qualities and it has served as a base for many potential novel drugs against cancer. Structurally, this molecule has two distinct conformations, one being a positively charged iminium form, and the other being an uncharged form, a pseudo-base.
Betulinic acid is a naturally occurring pentacyclic triterpenoid which has antiretroviral, antimalarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch from which it gets its name, same as the bracket fungus Fomitopsis betulina, but also the ber tree, selfheal, the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas, a member of the persimmon family, Tetracera boiviniana, the jambul, flowering quince, rosemary, and Pulsatilla chinensis.
Coramsine (SBP002) was an experimental cancer drug that was evaluated in preliminary clinical trials, but was abandoned by Solbec Pharmaceuticals Ltd after the results were insufficient for them to raise investment capital to continue its development.
Arenobufagin is a cardiotoxic bufanolide steroid secreted by the Argentine toad Bufo arenarum. It has effects similar to digitalis, blocking the Na+/K+ pump in heart tissue.
Tomatine is a glycoalkaloid, found in the stems and leaves of tomato plants, and in the fruits at much lower concentrations. Chemically pure tomatine is a white crystalline solid at standard temperature and pressure.
Tetrandrine, a bis-benzylisoquinoline alkaloid, is a calcium channel blocker. It is isolated from the plant Stephania tetrandra, and other Chinese and Japanese herbs.
Cecropins are antimicrobial peptides. They were first isolated from the hemolymph of Hyalophora cecropia, whence the term cecropin was derived. Cecropins lyse bacterial cell membranes; they also inhibit proline uptake and cause leaky membranes.
Solasodine is a poisonous alkaloid chemical compound that occurs in plants of the family Solanaceae such as potatoes and tomatoes. Solasonine and solamargine are glycoalkaloid derivatives of solasodine. Solasodine is teratogenic to hamster fetuses in a dose of 1200 to 1600 mg/kg. A 2013 literature survey found that various studies have indicated that solasodine may have diuretic, anticancer, antifungal, cardiotonic, antispermatogenetic, antiandrogenic, immunomodulatory, antipyretic and/or various other effects on central nervous system.
Solamargine is a cytotoxic chemical compound that occurs in plants of the family Solanaceae, such as potatoes, tomatoes, and eggplants. It has been also isolated from Solanum nigrum fungal endophyte Aspergillus flavus. It is a glycoalkaloid derived from the steroidal alkaloid solasodine.
Sonodynamic therapy (SDT) is a noninvasive treatment, often used for tumor irradiation, that utilizes a sonosensitizer and the deep penetration of ultrasound to treat lesions of varying depths by reducing target cell number and preventing future tumor growth. Many existing cancer treatment strategies cause systemic toxicity or cannot penetrate tissue deep enough to reach the entire tumor; however, emerging ultrasound stimulated therapies could offer an alternative to these treatments with their increased efficiency, greater penetration depth, and reduced side effects. Sonodynamic therapy could be used to treat cancers and other diseases, such as atherosclerosis, and diminish the risk associated with other treatment strategies since it induces cytotoxic effects only when externally stimulated by ultrasound and only at the cancerous region, as opposed to the systemic administration of chemotherapy drugs.
The tumor microenvironment is a complex ecosystem surrounding a tumor, composed of cancer cells, stromal tissue and the extracellular matrix. Mutual interaction between cancer cells and the different components of the tumor microenvironment support its growth and invasion in healthy tissues which correlates with tumor resistance to current treatments and poor prognosis. The tumor microenvironment is in constant change because of the tumor's ability to influence the microenvironment by releasing extracellular signals, promoting tumor angiogenesis and inducing peripheral immune tolerance, while the immune cells in the microenvironment can affect the growth and evolution of cancerous cells.
Immunogenic cell death is any type of cell death eliciting an immune response. Both accidental cell death and regulated cell death can result in immune response. Immunogenic cell death contrasts to forms of cell death that do not elicit any response or even mediate immune tolerance.
Oxytosis/ferroptosis is a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides, and is genetically and biochemically distinct from other forms of regulated cell death such as apoptosis. Oxytosis/ferroptosis is initiated by the failure of the glutathione-dependent antioxidant defenses, resulting in unchecked lipid peroxidation and eventual cell death. Lipophilic antioxidants and iron chelators can prevent ferroptotic cell death. Although the connection between iron and lipid peroxidation has been appreciated for years, it was not until 2012 that Brent Stockwell and Scott J. Dixon coined the term ferroptosis and described several of its key features. Pamela Maher and David Schubert discovered the process in 2001 and called it oxytosis. While they did not describe the involvement of iron at the time, oxytosis and ferroptosis are today thought to be the same cell death mechanism.