territrem B

territrem B Structure
CAS No.
70407-20-4
Chemical Name:
territrem B
Synonyms
territrem B;TERRITREM B(RG);PubChem ID: 114734;(4aR)-4a,6,6a,12,12a,12b-Hexahydro-4aβ,12aβ-dihydroxy-4,4,6aα,12bα-tetramethyl-9-(3,4,5-trimethoxyphenyl)-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-4,4,6a,12b-tetramethyl-9-(3,4,5-trimethoxyphenyl)-, (4aR,6aR,12aS,12bS)-
CBNumber:
CB91314602
Molecular Formula:
C29H34O9
Molecular Weight:
526.57
MOL File:
70407-20-4.mol
Modify Date:
2024/7/2 8:55:40

territrem B Properties

Melting point 200~203℃
Boiling point 693.0±55.0 °C(Predicted)
Density 1.35±0.1 g/cm3(Predicted)
storage temp. Store at -20°C
solubility DMSO: soluble
form A solid
pka 12.11±0.70(Predicted)
color White to off-white

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H301+H311-H330
Precautionary statements  P260-P264-P270-P271-P280-P284-P301+P310-P330-P302+P352-P304+P340-P312-P320-P361+P364-P403+P233-P405-P501
NFPA 704
0
4 0

territrem B Chemical Properties,Uses,Production

Description

Territrem B (TRB) is a fungal metabolite isolated from Aspergillus terreus shown previously to be a potent and irreversible inhibitor of acetylcholinesterase (AChE).

Uses

Territrem B is an α-pyrone tremorgenic mycotoxin first identified from an Aspergillus terreus strain by Ling and colleagues at Taiwan National University in 1979. Territrem B 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.

Biological Activity

Territrem B is a mycotoxin originally isolated from A. terreus that irreversibly inhibits acetylcholinesterase (AChE; IC50 = 19 nM for the electric eel enzyme). It is toxic to mice, inducing tremors with a median tremulous dose of 0.21 mg/kg, and has an LD50 value of 9.06 mg/kg.

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 B Preparation Products And Raw materials

Raw materials

Preparation Products

territrem B Suppliers

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territrem B (4aR)-4a,6,6a,12,12a,12b-Hexahydro-4aβ,12aβ-dihydroxy-4,4,6aα,12bα-tetramethyl-9-(3,4,5-trimethoxyphenyl)-4H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(5H)-dione TERRITREM B(RG) PubChem ID: 114734 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-4,4,6a,12b-tetramethyl-9-(3,4,5-trimethoxyphenyl)-, (4aR,6aR,12aS,12bS)- 70407-20-4