Microbial transformation of N-heptyl physostigmine, a semisynthetic alkaloid inhibitor of cholinesterase. 1995

L So, and R White, and B Arison, and B Petuch, and M S Schwartz, and H Cheng, and R Monaghan, and T S Chen
Merck Research Laboratories, Department of Fermentation Microbiology, Rahway, NJ 07065, USA.

The microbiological transformation of N-heptyl physostigmine (L-693,487) (1), a semisynthetic physostigmine cholinesterase inhibitor, was investigated using Verticillium lecanii MF 5713 (ATCC 74148), Acremonium sp MF 5723 (ATCC 74164) and Actinoplanes sp MA 6559 (ATCC 53771). Nine microbial metabolites (2-10) of 1 were isolated and purified using reversed-phase HPLC. The structures of the metabolites were established using spectroscopic techniques including MS and NMR. Some of the microbial metabolites were identical to metabolites present in urine of a dog treated with 1.

UI MeSH Term Description Entries
D010830 Physostigmine A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity. Eserine
D002800 Cholinesterase Inhibitors Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. Acetylcholinesterase Inhibitor,Acetylcholinesterase Inhibitors,Anti-Cholinesterase,Anticholinesterase,Anticholinesterase Agent,Anticholinesterase Agents,Anticholinesterase Drug,Cholinesterase Inhibitor,Anti-Cholinesterases,Anticholinesterase Drugs,Anticholinesterases,Cholinesterase Inhibitors, Irreversible,Cholinesterase Inhibitors, Reversible,Agent, Anticholinesterase,Agents, Anticholinesterase,Anti Cholinesterase,Anti Cholinesterases,Drug, Anticholinesterase,Drugs, Anticholinesterase,Inhibitor, Acetylcholinesterase,Inhibitor, Cholinesterase,Inhibitors, Acetylcholinesterase,Inhibitors, Cholinesterase,Inhibitors, Irreversible Cholinesterase,Inhibitors, Reversible Cholinesterase,Irreversible Cholinesterase Inhibitors,Reversible Cholinesterase Inhibitors
D003904 Mitosporic Fungi A large and heterogenous group of fungi whose common characteristic is the absence of a sexual state. Many of the pathogenic fungi in humans belong to this group. Deuteromycetes,Deuteromycota,Fungi imperfecti,Fungi, Mitosporic,Hyphomycetes,Deuteromycete,Deuteromycotas,Fungi imperfectus,Fungus, Mitosporic,Hyphomycete,Mitosporic Fungus,imperfectus, Fungi
D000164 Acremonium A mitosporic fungal genus with many reported ascomycetous teleomorphs. Cephalosporin antibiotics are derived from this genus. Cephalosporium,Acremoniums,Cephalosporiums
D001711 Biotransformation The chemical alteration of an exogenous substance by or in a biological system. The alteration may inactivate the compound or it may result in the production of an active metabolite of an inactive parent compound. The alterations may be divided into METABOLIC DETOXICATION, PHASE I and METABOLIC DETOXICATION, PHASE II.

Related Publications

L So, and R White, and B Arison, and B Petuch, and M S Schwartz, and H Cheng, and R Monaghan, and T S Chen
February 1992, Journal of the neurological sciences,
L So, and R White, and B Arison, and B Petuch, and M S Schwartz, and H Cheng, and R Monaghan, and T S Chen
October 1989, Neurochemical research,
L So, and R White, and B Arison, and B Petuch, and M S Schwartz, and H Cheng, and R Monaghan, and T S Chen
August 1991, Pharmacology, biochemistry, and behavior,
L So, and R White, and B Arison, and B Petuch, and M S Schwartz, and H Cheng, and R Monaghan, and T S Chen
September 1992, Neuroscience letters,
L So, and R White, and B Arison, and B Petuch, and M S Schwartz, and H Cheng, and R Monaghan, and T S Chen
January 1975, Ukrains'kyi biokhimichnyi zhurnal,
L So, and R White, and B Arison, and B Petuch, and M S Schwartz, and H Cheng, and R Monaghan, and T S Chen
August 1988, Journal of medicinal chemistry,
L So, and R White, and B Arison, and B Petuch, and M S Schwartz, and H Cheng, and R Monaghan, and T S Chen
January 1989, Folia microbiologica,
L So, and R White, and B Arison, and B Petuch, and M S Schwartz, and H Cheng, and R Monaghan, and T S Chen
August 2003, Natural product research,
L So, and R White, and B Arison, and B Petuch, and M S Schwartz, and H Cheng, and R Monaghan, and T S Chen
June 2009, European journal of oral sciences,
L So, and R White, and B Arison, and B Petuch, and M S Schwartz, and H Cheng, and R Monaghan, and T S Chen
February 1991, Onkologie,
Copied contents to your clipboard!