| Identification | Back Directory | [Name]
Toosendanin | [CAS]
58812-37-6 | [Synonyms]
Toosendani
TOOSENDANIN
Chuanliansu
Toosendaninr
Toosendan extract
Toosendan Fructus。
28-Deacetylsendanin
Toosendanin USP/EP/BP
12-AcetoxyaMoorastatin
Toosendanin 58812-37-6
Toosendanin, 98%, from Melia toosendan Sieb. et Zucc.
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]- | [Molecular Formula]
C30H38O11 | [MDL Number]
MFCD00210564 | [MOL File]
58812-37-6.mol | [Molecular Weight]
574.62 |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
12.15±0.70(Predicted) | [color ]
White to Pale Beige | [CAS DataBase Reference]
58812-37-6 |
| Hazard Information | Back Directory | [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. | [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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