Territrem B was isolated from Asperigillus terreus as a tremorgenic mycotoxin¹⁾. Futhrmore, the very similar compounds, arisugacins A and B were isolated from Penicillium sp. FO-4259 in the course of screening for selective acetylcholinesterase inhibitors²⁾ .

Their structures are comprised of a highly oxygenated trans decalin system and an α-pyrone moiety which belong biogenetically to the mixed polyketide-terpenoid group (meroterpenoid) (Figure 1)³⁾. The first total synthesis of arisugacins was achieved by Sunazuka –Omura⁴⁾ .

Arisugacins A, B and territrem B possess inhibitory activities against AChE (from human erythrocyted) in vitro, with IC₅₀ values of 1, 26, and 8 nM, respectively (Figure 2)⁵⁾. And the activity against AChE was more than 20,000 times higher than that against butyrylcholinesterase (BChE, from horse serum) (Table 1). The studies on the effects of arisugacin A on an animal model of scopolamine-induced amnesia showed that arisugacin A protected against amnesia and exhibited very weak effects on mouse salivation and hypothermia, a peripheral cholinergic response and central cholinergic response⁶⁾ .

Effects of territrem B on the central neuron of the snail Achatina fulica were studied electrophysiologically⁷⁾. It was predicted that an optimal territrem B-AChE binding would position a narrowing connection of the territrem B structure at a constricted area near the entrance of the gorge, thereby providing a structural basis for the observed irreversible binding (Figure 3, 4). Territrem-B potentiated the acetylcholine (ACh) induced current of the neuron, while it had no effect on GABA or L-glutamate elicited currents. Territrem B increased the peak amplitude of the response elicited by the first perfusion of ACh and depressed the increase in current produced by a second perfusion⁷⁾. They could be potentially excellent drugs for the treatment of AD.

Origin: Asperigillus terreus

CAS Registry Number: 70407-20-4

Appearance: off-white solid

Molecular Formula/ Weight: C₂₉H₃₄O₉=526.58

Purity: 95.0% by HPLC

Solubility: Soluble in MeOH, chloroform Insoluble in water

Handling and Storage: Store at -20℃.