Toosendanin Chemical Properties

Melting point:

170-175°C

Boiling point:

555.97°C (rough estimate)

Density 

1.2084 (rough estimate)

refractive index 

1.5970 (estimate)

storage temp. 

Refrigerator

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

12.15±0.70(Predicted)

form 

Solid

color 

White to Pale Beige

CAS DataBase Reference

58812-37-6

Safety Information

Safety Statements 

24/25

HS Code 

29389090

Toosendanin Usage And Synthesis

Description

Fructus Meliae Toosendan (chuan lian zi), the fruit of Melia toosendan Sieb. Et Zucc, is mainly produced in Sichuan, Hubei, Henan, and Hunan province in China .
Toosendanin is a tetracyclic triterpene compound extracted from fructus toosendan. It is an ascaridole agent and showed anti-botulinum, antibacterial, anticancer, and anti-inflammatory effects. It is also a neuromuscular blocking agent.

Physical properties

Appearance: white acicular crystal, colorless, bitter, and odorless. Solubility: soluble in ethanol, methanol, ethyl acetate, acetone, pyridine, etc., and slightly soluble in hot water, chloroform, benzene, and ether and insoluble in petroleum ether.

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 .

Uses

Toosendanin is a triterpenoid derivative, acts as a novel agonist of L-type Ca2+ channels in neonatal rat ventricular cells.

Uses

Toosendanin is a triterpenoid derivative and a novel agonist of L-type Ca2+ channels in neonatal rat ventricular cells (1,2,3).

Definition

ChEBI: Toosendanin is a limonoid.

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.

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