Citrusosides A-D and furanocoumarins with cholinesterase inhibitory activity from the fruit peels of Citrus hystrix.
Four new compounds, citrusosides A-D (1-4), and 15 known compounds were isolated from the hexanes and CH(2)Cl(2) extracts of the peels of Citrus hystrix fruits. Compound 1 is a 1-O-isopropyl-6-O-β-D-glucopyranosyl ester of 5'',9''-dimethyl-2'',8''-decadienoic acid. Compounds 2-4 possess a 1-O-isopropyl-β-D-glucopyranosyl and a dihydroxyprenylfuranocoumarin moiety conjugated to the 3-hydroxy-3-methylglutaric acid as diesters. Several furanocoumarins were evaluated for their cholinesterase inhibitory activity. (R)-(+)-6'-Hydroxy-7'-methoxybergamottin, (R)-(+)-6',7'-dihydroxybergamottin, and (+)-isoimparatorin showed IC(50) values of 11.2 ± 0.1, 15.4 ± 0.3, and 23 ± 0.2 μM, respectively. Bioassay results indicated that the presence of a dioxygenated geranyl chain in the test compounds is crucial for the inhibitory activity.
Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Ramkhamhaeng University, Hua Mark, Bangkapi, Bangkok 10240, Thailand.
Juthamanee
J
Youkwan
Somyote
S
Sutthivaiyakit
Pakawadee
P
Sutthivaiyakit
D002091:Butyrylcholinesterase / Q000378:metabolism; D002800:Cholinesterase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002957:Citrus / Q000737:chemistry*; D005638:Fruit / Q000737:chemistry; D011564:Furocoumarins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012855:Sitosterols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013237:Stereoisomerism; D013785:Thailand
D002800:Cholinesterase Inhibitors; D011564:Furocoumarins; D005960:Glucosides; D012855:Sitosterols; D002091:Butyrylcholinesterase