territrem A

territrem A Structure
CAS No.
70407-19-1
Chemical Name:
territrem A
Synonyms
territrem A;TERRITREM A(RG);Territrem A(95%);PubChem ID: 115079;(4aR)-4a,6,6a,12,12a,12b-Hexahydro-4aβ,12aβ-dihydroxy-9-(7-methoxy-1,3-benzodioxol-5-yl)-4,4,6aα,12bα-tetramethyl-4H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(5H)-dione;4H,11H-Naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(5H)-dione, 4a,6,6a,12,12a,12b-hexahydro-4a,12a-dihydroxy-9-(7-methoxy-1,3-benzodioxol-5-yl)-4,4,6a,12b-tetramethyl-, (4aR,6aR,12aS,12bS)-
CBNumber:
CB61359936
Molecular Formula:
C28H30O9
Molecular Weight:
510.53
MOL File:
70407-19-1.mol
Modify Date:
2023/5/21 10:59:17

territrem A Properties

storage temp. Store at -20°C
solubility DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble
form A solid

territrem A Chemical Properties,Uses,Production

Description

Territrem A is a mycotoxin originally isolated from A. terreus that irreversibly inhibits acetylcholinesterase (AChE; IC50 = 24 nM for the electric eel enzyme). It is toxic to mice, inducing tremors with a median tremulous dose of 0.31 mg/kg, and has an LD50 value of 17.6 mg/kg.

Uses

Territrem A is an α-pyrone tremorgenic mycotoxin first identified from an Aspergillus terreus strain by Ling and colleagues at Taiwan National University in 1979. Territrem A is a potent insecticide acting via irreversible inhibition of acetylcholinesterase (AChE). The binding mechanism is very different from typical irreversible AChE inhibitors like neostigmine and the organophospates.

References

Territrems, tremorgenic mycotoxins of Aspergillus terreus. Ling K.L. et al., Appl. Env. Microbiol. 1979, 37, 355.
Toxicity and anticholinesterase activity of the fungal metabolites territrems to the corn earworm, Helicoverpa zea. Dowd P.F. et al., Entomol. Exp. Appl. 1992, 65, 57.
Territrem B, a tremorgenic mycotoxin that inhibits acetylcholinesterase with a noncovalent yet irreversible binding mechanism. Jen-Wei Chen J-W. et al., J. Biol. Chem. 1999, 274, 34916.

territrem A Preparation Products And Raw materials

Raw materials

Preparation Products

territrem A (4aR)-4a,6,6a,12,12a,12b-Hexahydro-4aβ,12aβ-dihydroxy-9-(7-methoxy-1,3-benzodioxol-5-yl)-4,4,6aα,12bα-tetramethyl-4H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(5H)-dione TERRITREM A(RG) PubChem ID: 115079 4H,11H-Naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(5H)-dione, 4a,6,6a,12,12a,12b-hexahydro-4a,12a-dihydroxy-9-(7-methoxy-1,3-benzodioxol-5-yl)-4,4,6a,12b-tetramethyl-, (4aR,6aR,12aS,12bS)- Territrem A(95%) 70407-19-1