58812-37-6

Basic information

• Product Name: Toosendanin
• Synonyms: TOOSENDANIN;24-Norchola-20,22-diene-4-carboxaldehyde,3,12-bis(acetyloxy)-14,15:21,23-diepoxy-1,7,19-trihydroxy-4,8-dimethyl-11-oxo-,cyclic4,19-hemiacetal, [C(R),1α,3α,4β, 5α,7α,12α,13α,14β,15β,17α]-;Chuanliansu;28-Deacetylsendanin;12-AcetoxyaMoorastatin;Toosendanin, 98%, from Melia toosendan Sieb. et Zucc.
• CAS NO: 58812-37-6
• Molecular Formula: C₃₀H₃₈O₁₁
• Molecular Weight: 574.62
• Product Categories: Limonoids (Citrus, Bitter Compounds);chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 58812-37-6.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 555.97°C (rough estimate)
• Flash Point: 385.6 °C
• Appearance: /
• Density: 1.2084 (rough estimate)
• Vapor Pressure: 2.15E-21mmHg at 25°C
• Refractive Index: 1.5970 (estimate)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.15±0.70(Predicted)
• CAS DataBase Reference: Toosendanin(CAS DataBase Reference)
• NIST Chemistry Reference: Toosendanin(58812-37-6)
• EPA Substance Registry System: Toosendanin(58812-37-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 58812-37-6(Hazardous Substances Data)

Usage

Description

Toosendanin, a tetracyclic triterpene compound, is extracted from Fructus Meliae Toosendan (chuan lian zi), the fruit of Melia toosendan Sieb. Et Zucc. It is an ascaridole agent with a white acicular crystal appearance, colorless, bitter, and odorless. Toosendanin is soluble in ethanol, methanol, ethyl acetate, acetone, pyridine, and slightly soluble in hot water, chloroform, benzene, and ether, but insoluble in petroleum ether. It exhibits anti-botulinum, antibacterial, anticancer, and anti-inflammatory effects and is also known as a neuromuscular blocking agent.

Uses

Used in Pharmaceutical Applications:
Toosendanin is used as a novel agonist of L-type Ca2+ channels in neonatal rat ventricular cells for its potential therapeutic effects on various conditions related to cardiac function and muscle contraction.
Used in Anthelmintic Applications:
As an ascaridole agent, Toosendanin is used for its anthelmintic properties, helping to eliminate or reduce parasitic worm infections.
Used in Antimicrobial Applications:
Toosendanin is used as an antibacterial agent, leveraging its antimicrobial properties to combat bacterial infections.
Used in Anticancer Applications:
Toosendanin is used for its anticancer effects, potentially contributing to the development of novel cancer treatments.
Used in Anti-inflammatory Applications:
Toosendanin is used to reduce inflammation and alleviate symptoms associated with inflammatory conditions.
Used in Neuromuscular Blocking Applications:
As a neuromuscular blocking agent, Toosendanin is used in medical procedures where muscle relaxation is required, such as surgeries or certain diagnostic tests.

History

Toosendanin is the main chemical composition of the fructus toosendan. Researches on this compound could date back to 1953. Toosendanin has been named in 1955, while its structure was identified 20 years later by mass spectrometry. Toosendanin is a triterpenoid derivative containing a β-substituted furan ring . A new synthetic strategy is put forth allowing access to a 4-acetoxy CD fragment analogue of toosendanin, which was achieved from mesityl oxide and acetylacetone in 14 steps in 2009 . The anti-parasite of toosendanin was reported in 1971. In 1980, it was identified as a selective neuromuscular blocking agent that acts on neuromuscular junction . The anti-botulinum effect of toosendanin was discovered in 1982 . In recent years, it is also observed that toosendanin can induce differentiation and apoptosis . Toosendanin could inhibit the growth of feeding larvae and insects. It has been used as pollution-free, no residue of botanical insecticides for the production of fruits and vegetables in China .

Indications

Insecticide

Pharmacology

By interfering with neurotransmitter release and causing an initial facilitated diffusion toosendanin eventually blocks synaptic transmission at both the neuromuscular junction and central synapses. Toosendanin is sharing many similar actions with botulinum neurotoxin on blocking neuromuscular transmission, but it has very low biological activity compared with botulinum neurotoxin. Studies suggest that the anti-botulinum effect is achieved by preventing botulinum neurotoxin from approaching its enzymatic substrate, SNARE protein. Toosendanin can induce differentiation and apoptosis in several cell lines and suppress proliferation of various human cancer cells. It inhibits K+ channel and facilitates L-type Ca2+ channel, which is associated with parts of its biological activities . In a word, activities of toosendanin include selective neuromuscular blocking, effectively antagonizing botulism, inducing cell differentiation and apoptosis and inhibiting proliferation of various human cancer cells, inhibiting feeding and development in insects, and modifying K+ and Ca2+ channel activity.

Clinical Use

Fructus Meliae Toosendan is a traditional Chinese medicine which is still used in internal medicine.

InChI:InChI=1/C30H38O11/c1-13(31)39-20-10-19(34)29-12-38-25(36)26(20,3)17(29)9-18(33)28(5)23(29)22(35)24(40-14(2)32)27(4)16(15-6-7-37-11-15)8-21-30(27,28)41-21/h6-7,11,16-21,23-25,33-34,36H,8-10,12H2,1-5H3/t16-,17-,18+,19-,20?,21+,23-,24-,25?,26+,27+,28+,29+,30+/m0/s1