3'-R/S-hydroxyvoacamine, a potent acetylcholinesterase inhibitor from Tabernaemontana divaricata

Wantida Chaiyana; Jan Schripsema; Kornkanok Ingkaninan; Siriporn Okonogi

doi:10.1016/j.phymed.2012.12.016

3'-R/S-hydroxyvoacamine, a potent acetylcholinesterase inhibitor from Tabernaemontana divaricata

Phytomedicine. 2013 Apr 15;20(6):543-8. doi: 10.1016/j.phymed.2012.12.016. Epub 2013 Jan 30.

Authors

Wantida Chaiyana¹, Jan Schripsema, Kornkanok Ingkaninan, Siriporn Okonogi

Affiliation

¹ Department of Pharmaceutical Sciences, Faculty of Pharmacy, Chiang Mai University, Chiang Mai 50200, Thailand.

PMID: 23375813
DOI: 10.1016/j.phymed.2012.12.016

Abstract

Guided by the acetylcholinesterase inhibiting activity, the bisindole alkaloid 3'-R/S-hydroxyvoacamine was isolated from a stem extract of Tabernaemontana divaricata, a plant used in Thailand in traditional rejuvenation remedies for improving the memory. The structure of the alkaloid was elucidated by extensive use of NMR spectroscopy and the complete assignment of the (1)H and (13)C NMR spectra is reported. The alkaloid acted as a non-competitive inhibitor against AChE with an IC50 value of 7.00±1.99 μM. An HPLC method was developed for the quantitative analysis of the AChE inhibitor. It suggested that there was 12.4% (w/w) of 3'-R/S-hydroxyvoacamine in the alkaloid enriched fraction of T. divaricata stem.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylcholinesterase / metabolism*
Cholinesterase Inhibitors / chemistry
Cholinesterase Inhibitors / isolation & purification
Cholinesterase Inhibitors / pharmacology*
Humans
Ibogaine / analogs & derivatives*
Ibogaine / chemistry
Ibogaine / isolation & purification
Ibogaine / pharmacology
Inhibitory Concentration 50
Molecular Structure
Plant Extracts / chemistry
Plant Extracts / pharmacology*
Tabernaemontana / chemistry*

Substances

3'-hydroxyvoacamine
Cholinesterase Inhibitors
Plant Extracts
Ibogaine
Acetylcholinesterase