Selective cholinesterase inhibitory activities of a new monoterpene diglycoside and other constituents from Nelumbo nucifera stamens

Biological & Pharmaceutical Bulletin
Hyun Ah JungJae Sue Choi

Abstract

A new beta-cyclogeraniol diglycoside (5), along with four known components, cycloartenol (1), p-hydroxybenzoic acid (2), vanilloloside (3), and 5'-O-methyladenosine (4), were first isolated from the n-BuOH fraction of Nelumbo nucifera stamens. The chemical structure of 5 was elucidated as 1-hydroxymethyl-2,6,6-trimethyl-1-cyclohexene 9-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (nuciferoside) on the basis of chemical and spectroscopic evidence, including 1D, 2D NMR, and MS. The anti-Alzheimer effects of 1-5 were evaluated via the acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and beta-site amyloid precursor protein (APP) cleaving enzyme 1 (BACE1) inhibition assays. Compounds 1-3 and 5 showed good and noncompetitive inhibition against AChE with IC(50) values of 11.89, 20.07, 4.55, and 3.20 microM and K(i)values of 15.71, 25.44, 7.76, and 5.76 microM, respectively. Compounds 1, 2, and 5 also possessed BChE inhibitory activities with IC(50) values of 13.93, 62.29, 205.78, and 83.06 microM, respectively. The selectivity index (SI) values of 1, 2, 3, and 5, calculated from IC(50) values of BChE and AChE, were 1.2, 3.1, 45.7, and 26.0. However, all isolated compounds lacked BACE1 inhibition up to 100 microM. T...Continue Reading

References

Jul 1, 1987·Journal of Natural Products·N ShojiY Ohizumi
May 1, 1995·Journal of Ethnopharmacology·B la CourZ Yi
Jan 1, 1995·Pharmacology & Therapeutics·A L Harvey
Aug 1, 1997·Planta medica·P K MukherjeeB P Saha
Jan 8, 1998·Journal of Ethnopharmacology·P K MukherjeeB P Saha
Aug 17, 2000·Bioscience, Biotechnology, and Biochemistry·R OkazakiT Oritani
Oct 1, 1990·Proceedings of the National Academy of Sciences of the United States of America·W D NesE R Katz
Nov 28, 2002·Advanced Drug Delivery Reviews·Robert Vassar
May 3, 2003·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·D H SohnB H Lee
May 9, 2003·Archives of Pharmacal Research·Hyun Ah JungJae Sue Choi
Aug 5, 2003·Pharmacology, Biochemistry, and Behavior·Nicolette S L PerryClive Ballard
Aug 28, 2003·Lancet Neurology·Elio ScarpiniHoward Feldman
Sep 19, 2003·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·E J ChoJ C Park
Jul 1, 1961·Biochemical Pharmacology·G L ELLMANR M FEATHER-STONE
Dec 31, 2003·The American Journal of Chinese Medicine·Ming-Jiuan WuJui-Hung Yen
Jun 5, 2004·Journal of Clinical Neuroscience : Official Journal of the Neurosurgical Society of Australasia·M S Parihar, Taruna Hemnani
Oct 11, 2005·Planta·M V AgeevaA A M van Lammeren
Oct 22, 2005·Journal of Ethnopharmacology·Sujay RaiPulok K Mukherjee
Feb 24, 2006·Journal of Ethnopharmacology·Yuka OnoYasushi Ohizumi
May 10, 2006·Archives of Pharmacal Research·Sook Kyung HyunJae Sue Choi
Aug 2, 2006·Phytotherapy Research : PTR·Soon Sung LimJae Sue Choi
Dec 29, 2006·Chemistry & Biodiversity·M Iqbal ChoudharyUNKNOWN Atta-ur-Rahman
Jul 20, 2007·Phytotherapy Research : PTR·Pulok K MukherjeePeter J Houghton
Oct 2, 2007·Journal of Medicinal Chemistry·Thibault SauvaîtreCatherine Guillou
Oct 27, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mankil Jung, Moonso Park
Dec 12, 2007·Journal of Medical Toxicology : Official Journal of the American College of Medical Toxicology·Leslie Dye

❮ Previous
Next ❯

Citations

Jan 5, 2012·International Journal of Alzheimer's Disease·Mona MehtaMarwan Sabbagh
Jul 20, 2010·Journal of Periodontology·Symone M San MiguelKathy K H Svoboda
Nov 11, 2011·CNS Neuroscience & Therapeutics·Elaine Perry, Melanie-Jayne R Howes
Feb 5, 2011·Journal of Ethnopharmacology·Puongtip KunanusornVichai Reutrakul
Oct 24, 2013·European Journal of Medicinal Chemistry·Manjinder SinghDhandeep Singh
Dec 29, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Srijan ShresthaJae Sue Choi
Jan 12, 2019·Critical Reviews in Food Science and Nutrition·Guilin ChenMingquan Guo
Oct 11, 2014·Archives of Pharmacal Research·Hyun Ah JungJae Sue Choi
Jul 15, 2015·Archives of Pharmacal Research·Md Yousof AliJae Sue Choi
Aug 23, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Piya TemviriyanukulUthaiwan Suttisansanee
Feb 20, 2020·Current Medicinal Chemistry·Natália Martins, Isabel C F R Ferreira
Feb 4, 2021·Journal of Food Biochemistry·Ganesamoorthy JanarnyKamburawala Kankanamge Don Somathilaka Ranaweera
Apr 30, 2021·Biomedicine & Pharmacotherapy = Biomédecine & Pharmacothérapie·Sagheer AhmedAhmed Al-Harrasi
Jun 8, 2021·Critical Reviews in Food Science and Nutrition·Sajad FakhriHaroon Khan

❮ Previous
Next ❯

Related Concepts

Related Feeds

Alzheimer's Disease: Amyloid Beta

Alzheimer's disease is a neurodegenerative disease associated with the accumulation of amyloid plaques in the brain; these plaques are comprised of amyloid beta deposits. Here is the latest research in this field.

Alzheimer's Disease: APP

Amyloid precursor protein (APP) proteolysis is critical for the development of Alzheimer's disease, a neurodegenerative disease associated with accumulation of amyloid plaques in the brain. Here is the latest research on APP and Alzheimer's disease.