MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 574255 | Name: Territrem B
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Territrem B is a mycotoxin that irreversibly inhibits acetylcholinesterase (AChE). It is toxic to mice, inducing tremors with a median tremulous dose of 0.21 mg/kg.

Chemical Structure

Territrem B
Territrem B
CAS#70407-20-4

Theoretical Analysis

MedKoo Cat#: 574255

Name: Territrem B

CAS#: 70407-20-4

Chemical Formula: C29H34O9

Exact Mass: 526.2203

Molecular Weight: 526.58

Elemental Analysis: C, 66.15; H, 6.51; O, 27.34

Price and Availability

Size Price Availability Quantity
1mg USD 500.00
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Territrem B
IUPAC/Chemical Name
(4aR,6aR,12aS,12bS)-4a,6,6a,12,12a,12b-hexahydro-4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-9-(3,4,5-trimethoxyphenyl)-4H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(5H)-dione
InChi Key
PBXNNDFKPQPJBB-VJLHXPKFSA-N
InChi Code
InChI=1S/C29H34O9/c1-25(2)9-8-22(30)27(4)28(25,32)11-10-26(3)29(27,33)15-17-19(38-26)14-18(37-24(17)31)16-12-20(34-5)23(36-7)21(13-16)35-6/h8-9,12-14,32-33H,10-11,15H2,1-7H3/t26-,27+,28-,29-/m1/s1
SMILES Code
O=C1C=CC(C)(C)[C@]([C@@]21C)(O)CC[C@@]([C@]2(O)C3)(C)OC4=C3C(OC(C5=CC(OC)=C(OC)C(OC)=C5)=C4)=O
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 526.58 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Wang HL, Li R, Zhao M, Wang ZY, Tang H, Cao ZY, Zheng GL, Zhang W. A Drimane Meroterpenoid Borate as a Synchronous Ca+ Oscillation Inhibitor from the Coral-Associated Fungus Alternaria sp. ZH-15. J Nat Prod. 2023 Feb 24;86(2):429-433. doi: 10.1021/acs.jnatprod.2c01028. Epub 2023 Feb 2. PMID: 36729068. 2: Knorr DY, Georges NS, Pauls S, Heinrich R. Acetylcholinesterase promotes apoptosis in insect neurons. Apoptosis. 2020 Oct;25(9-10):730-746. doi: 10.1007/s10495-020-01630-4. PMID: 32761307; PMCID: PMC7527371. 3: Al-Rashid ZF, Hsung RP. A computational view on the significance of E-ring in binding of (+)-arisugacin A to acetylcholinesterase. Bioorg Med Chem Lett. 2015 Nov 1;25(21):4848-4853. doi: 10.1016/j.bmcl.2015.06.047. Epub 2015 Jun 27. PMID: 26159481; PMCID: PMC4670034. 4: Cheung J, Gary EN, Shiomi K, Rosenberry TL. Structures of human acetylcholinesterase bound to dihydrotanshinone I and territrem B show peripheral site flexibility. ACS Med Chem Lett. 2013 Sep 23;4(11):1091-6. doi: 10.1021/ml400304w. PMID: 24900610; PMCID: PMC4027152. 5: Cheung J, Beri V, Shiomi K, Rosenberry TL. Acetylcholinesterase complexes with the natural product inhibitors dihydrotanshinone I and territrem B: binding site assignment from inhibitor competition and validation through crystal structure determination. J Mol Neurosci. 2014 Jul;53(3):506-10. doi: 10.1007/s12031-014-0261-3. Epub 2014 Feb 27. PMID: 24573600. 6: Sun X, Kong X, Gao H, Zhu T, Wu G, Gu Q, Li D. Two new meroterpenoids produced by the endophytic fungus Penicillium sp. SXH-65. Arch Pharm Res. 2014 Aug;37(8):978-82. doi: 10.1007/s12272-013-0268-2. Epub 2013 Oct 30. PMID: 24166709. 7: Huang X, Sun X, Ding B, Lin M, Liu L, Huang H, She Z. A new anti- acetylcholinesterase α-pyrone meroterpene, arigsugacin I, from mangrove endophytic fungus Penicillium sp. sk5GW1L of Kandelia candel. Planta Med. 2013 Nov;79(16):1572-5. doi: 10.1055/s-0033-1350896. Epub 2013 Sep 30. PMID: 24081685. 8: Beri V, Wildman SA, Shiomi K, Al-Rashid ZF, Cheung J, Rosenberry TL. The natural product dihydrotanshinone I provides a prototype for uncharged inhibitors that bind specifically to the acetylcholinesterase peripheral site with nanomolar affinity. Biochemistry. 2013 Oct 22;52(42):7486-99. doi: 10.1021/bi401043w. Epub 2013 Oct 9. PMID: 24040835. 9: Jiang X, Ao L, Zhou C, Yang L, Zhang Q, Li H, Sun L, Wu X, Bai H, Zhao Y. Design, synthesis, and biological evaluation of new territrem B analogues. Chem Biodivers. 2005 Apr;2(4):557-67. doi: 10.1002/cbdv.200590036. PMID: 17192004. 10: Peng FC, Chang CC, Yang CY, Edwards RJ, Doehmer J. Territrems B and C metabolism in human liver microsomes: major role of CYP3A4 and CYP3A5. Toxicology. 2006 Feb 1;218(2-3):172-85. doi: 10.1016/j.tox.2005.10.010. Epub 2005 Dec 5. PMID: 16337070. 11: Peng FC, Jian WC, Edwards RJ. Profile of territrem metabolism and cytochrome P-450 3A expression in liver microsomes from Wistar rats of both genders as a function of age. J Toxicol Environ Health A. 2005 Nov 12;68(21):1871-88. doi: 10.1080/15287390500226763. PMID: 16207635. 12: Peng FC, Chen PC, Jeng YJ, Edwards RJ. Metabolism of territrem B and C in liver microsomes from 14-wk-old Wistar rats is catalyzed by cytochrome P-450 3A. J Toxicol Environ Health A. 2005 Feb 27;68(4):299-314. doi: 10.1080/15287390590895874. PMID: 15799453. 13: Peng FC, Cheng CH, Liu JC, Wu MF, Lee SH, Pan HJ. Production of polyclonal antibodies against territrem B and detection of territrem B in the conidia of Aspergillus terreus 23-1 by immunoelectron microscopy. J Agric Food Chem. 2004 Jun 2;52(11):3360-5. doi: 10.1021/jf030787n. PMID: 15161198. 14: Handa M, Sunazuka T, Nagai K, Kimura R, Otoguro K, Harigaya Y, Omura S. Determination of absolute stereochemistries of arisugacin F and Territrem B, novel acetylcholinesterase inhibitors. J Antibiot (Tokyo). 2001 Apr;54(4):386-91. doi: 10.7164/antibiotics.54.386. PMID: 11426665. 15: Zehnder LR, Hsung RP, Wang J, Golding GM. A Concise Stereoselective Route to the Pentacyclic Frameworks of Arisugacin A and Territrem B. Angew Chem Int Ed Engl. 2000 Nov 3;39(21):3876-3879. doi: 10.1002/1521-3773(20001103)39:21<3876::AID-ANIE3876>3.0.CO;2-C. PMID: 29711687. 16: Otoguro K, Shiomi K, Yamaguchi Y, Arai N, Sunazuka T, Masuma R, Iwai Y, Omura S. Arisugacins C and D, novel acetylcholinesterase inhibitors and their related novel metabolites produced by Penicilium sp. FO-4259-11. J Antibiot (Tokyo). 2000 Jan;53(1):50-7. doi: 10.7164/antibiotics.53.50. PMID: 10724008. 17: Chen JW, Luo YL, Hwang MJ, Peng FC, Ling KH. Territrem B, a tremorgenic mycotoxin that inhibits acetylcholinesterase with a noncovalent yet irreversible binding mechanism. J Biol Chem. 1999 Dec 3;274(49):34916-23. doi: 10.1074/jbc.274.49.34916. PMID: 10574966. 18: Ling KH. Territrem: neurotoxicity and biotransformation. J Toxicol Sci. 1998 Jul;23 Suppl 2:189-90. doi: 10.2131/jts.23.supplementii_189. PMID: 9760461. 19: El-Sayed Abdalla A, Zeinab Kheiralla M, Sahab A, Hathout A. Aspergillus terreus and its toxic metabolites as a food contaminant in some Egyptian Bakery products and grains. Mycotoxin Res. 1998 Jun;14(2):83-91. doi: 10.1007/BF02945097. PMID: 23605064. 20: Peng FC. Structure and anti-acetylcholinesterase activity of 4 alpha-(hydroxymethyl)-4 alpha-demethylterritrem B. J Nat Prod. 1997 Aug;60(8):842-3. doi: 10.1021/np9701236. PMID: 9287420.

View History

Terflavoxate

Terflavoxate

Featured