72741-87-8O[C@H]1[C@H]2[C@H](O)CCCN2C[C@H]1OFXUAIOOAOAVCGD-WCTZXXKLSA-NSwainsonine is an indolizidine alkaloid isolated from the plant Swainsona canescens with three hydroxy substituents at positions 1, 2 and 8. It has a role as an antineoplastic agent, an immunological adjuvant, an EC 3.2.1.114 (mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase) inhibitor and a plant metabolite.
72741-87-8DTXSID5046356Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
The presence of phytotoxins in plants constitutes a health risk for herbivores, particularly on ruminants who accidently consume them. Among the adverse effects produced by these exposures are reproductive alterations, represented by abortion, infertility, and morphological alterations in neonates, which are frequently attributed to other causes. While in some cases the plants that contain such metabolites are known, other times they are not, leading to alterations that are difficult to treat considering that their toxicodynamics are unknown.
Swainsonine causes a variety of neurological disorders, including locoism and "slobbers syndrome" in livestock. In man it causes a lysosomal storage disease, biochemically and morphologically similar to mannosidosis. It is also an appetite suppressant. (L1248, A3092, A3093)
Swainsonine inhibits the activity of glycoside hydrolases, especially N-linked glycosylation. Inhibition of Golgi mannosidase II and other alpha-mannosidases causes the accumulation of atypical hybrid glycoproteins and oligosaccarides because the proper processing cannot occur. This also results in intracellular vacuolization. (L1248, A3092, A3093)
Tridolgosir competitively inhibits the alpha manosidase II (alphaMII), which processes N linked carbohydrates of newly synthesized glycoproteins passing through the Golgi apparatus to the cell surface. Highly branched carbohydrate structures are created which bind to Lectin-phytohemagglutinin (L-PHA) and are subsequently expressed in different tumor types which results in metastatic phenotype, which is correlated with an increased aggressiveness in animals and causes other human malignancies. Inhibition of alphaMII reduces carbohydrates that bind to L-PHA, reducing aggressiveness, metastatic phenotype cells, slows tumor growth, and increases“hybrid type” carbohydrates on the cell surface. Hybrid type carbohydrates may increase cytokine activation of lymphocytes, increasing tumor susceptibility to lymphokine activated and natural killer cells.
Locoweed contains the indolizidine alkaloid swainsonine. Livestock that consume locoweed can suffer from locoism. The toxic component in locoweed has been identified as swainsonine. Swainsonine inhibits lysosomal a-mannosidase and mannosidase II, resulting in altered oligosaccharide degradation and incomplete glycoprotein processing. Endophytic fungi producing swainsonine have been isolated from a variety of locoweed, and these fungi and locoweed have a close relationship, e.g., endophytic fungi can promote the growth of locoweed and increase swainsonine production. Livestock that consume locoweed exhibit several symptoms, including dispirited behavior, staggering gait, chromatopsia, trembling, ataxia, and cellular vacuolar degeneration of most tissues.
Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity.
Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
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CHEMBL371197CHEBI:9367Several plants that contain indolizidine alkaloids, including swainsonine, are toxic to livestock, causing dysfunctional lysosomes and storage disease. Swainsonine induces a neurovisceral disease, known as locoism, in sheep, goats, and cattle. Locoism occurs in several parts of the world, e.g., the western United States, China, and parts of Australia. In South America, locoism has been described in the Andean region of Argentina affecting sheep, cattle, and llamas. This publication describes the clinical course in llamas, which was about 15 days, and included moderate ataxia, incoordination of hindlimbs, and progressive loss of body condition. Swainsonine was detected in stem and leaf samples of A. punae at a concentration of 0.06%. A diagnosis of swainsonine toxicosis caused by the consumption of A. punae was made based on clinical history and signs, histologic and ultrastructural changes, and plant analysis.
Symptoms of locoism include staggering gait, depression, muscular incoordination, staring, nervousness, hyperexcitability, loss of appetite, and reproductive alterations such as abortion and birth defects. The major symptom of "slobbers syndrome" is profuse salivation. Other symptoms include diarrhea, lacrimation, stiff joints, frequent urination, tremors, spontaneous abortion, labored breathing, loss of appetite, bloat, and possibly death. Swainsonine also causes vacuolation of most tissues. (L1819, A3092, A3093)
Swainsonine is the primary toxin in locoweeds. It causes intention tremors, reproductive dysfunction, emaciation, and death. In a mouse study, three generations were given a range of concentrations of swainsonine by intraperitoneal injection (2.50 mg/kg body weight (BW), 1.20 mg/kg BW, 0.60 mg/kg BW, and 0 mg/kg BW). The results results indicate that swainsonine may cause reproductive and developmental toxicities in mice in both parents and offspring.
Swainsonine is the principal agent in locoweed responsible for inducing locoism in animals. The toxicity of Embellisia fungi isolated from locoweed was compared with locoweed toxicity. Rats were fed diets containing locoweed, fungus and alfalfa, or alfalfa. Similar intracellular vacuolation was observed in renal, pancreatic, and hepatic tissues of rats that consumed either locoweed or fungus. Rats that ate locoweed or Embellisia fungi displayed indistinguishable toxicity symptoms. The Embellisia fungi from locoweed can induce toxicity without the plants.
Spontaneous intoxication by Astragalus arequipensis was diagnosed in a flock of 300 sheep that grazed an area heavily invaded by this plant. The main clinical signs were intention tremors, ataxia, and progressive loss of condition. The main microscopic changes were fine cytoplasmic vacuolation of cells in the cerebrum, cerebellum, thyroid and adrenal glands, kidney, liver, pancreas, urinary bladder, and lymph nodes, and swollen axons in the cerebellum. Composite leaf and stem samples of A. arequipensis analyzed by high-performance liquid chromatography contained 0.05% swainsonine. The diagnosis of intoxication by A. arequipensis was made based on the clinical history and signs, the gross, microscopic, and ultrastructural changes, and the detection of swainsonine in the plant.
Lysosomal storage diseases can causeimpaired cellular function and death. Many acquired lysosomal storage diseases are produced by toxic plants containing indolizidine alkaloids. This includes swainsonine, which inhibits lysosomal α-mannosidase and Golgi α-mannosidase II. Swainsonine-induced nervous disease associated with various plants has been reported, including species of the genus Astragalus, Sida, Oxitropis, Swainsona, and Ipomoea. The diagnosis of Astragalus spp. intoxication is established based on clinical signs, microscopic and ultrastructural findings, lectin histochemistry, the abundance of these plants in the grazing area, and the determination of swainsonine in plant specimens.
DescriptionSwainsonine (72741-87-8) is a naturally occurring alkaloidal toxin found in locoweed. Inhibits the biosynthesis of complex glycoproteins by inhibition of Golgi mannosidase II (IC50 = 0.2 mM).1 Inhibits growth and potentiates the cytotoxic effect of taxol in hepatocellular carcinoma in vivo.2 Induces apoptosis in a variety of cell types including cerebral cortical neurons.3 Impairs adult neurogenesis and spatial learning and memory.4 Abrogation of complex glycosylation by swainsonine results in strain-and cell-specific inhibition of prion replication.5 Induces lysosomal storage disease in farm animals.6
OccurrenceSwainsonia canescens yields this simple alkaloid.
UsesSwainsonine is an indolizidine alkaloid naturally found in certain plants including locoweed that inhibits N-linked glycoside hydrolases, preventing the processing of asparagine-linked glycoproteins. It reversibly inhibits lysosomal α-mannosidase and Golgi α-mannosidase II (IC50 = 0.2 μM). Swainsonine is used to study the role of N-linked glycosylation in cellular processes and has been shown to have antiproliferative and antimetastatic effects of cancer cells in culture and in mice. The inhibition of α-mannosidase activity in lysosomes produces an accumulation of partially-processed oligosaccharides and glycoproteins, giving rise to lysosomal storage disease. Swainsonine toxicity in herbivores results in a condition known as locoism, characterized by hyperactivity, aggression, stiff and clumsy gait, low head carriage, salivation, seizures, and apparent blindness, culminating in increased miscoordination, weakness and death.
UsesSwainsonine is a plant alkaloid derived from Swainsona canescens (a leguminous plant). It is a reversible, active-site directed inhibitor of a-mannosidase at concentrations of 5-10mM. At acid pH, swainsonine resembles an intermediate in the hydrolysis of mannosidases.Swainsonine completely inhibits mammalian Golgi a-mannosidase II (a-3/6-mannosidase in the glycoprotein processing pathway) and mammalian lysosomal a-mannosidase (acid mannosidase). At higher concentrations, swainsonine also inhibits mammalian cytosolic a-mannosidase. It has been shown to inhibit growth of transformed fibroblasts in soft agar and to enhance the antiproliferative effects of INF on murine lymphoreticular tumor cells in vitro. It also blocks the expression of b1-6 branched complex-type oligosaccharides and shun
General DescriptionSwainsonine is produced by endophytes, plant and insect pathogens. It is synthesized from the pipecolic acid and mevalonic acid. Swainsonine is a water-soluble indole alkaloid.
DefinitionChEBI: An indolizidine alkaloid isolated from the plant Swainsona canescens with three hydroxy substituents at positions 1, 2 and 8.