Activity-guided fractionation of the leaves of Ormosia sumatrana using a proteasome inhibition assay.
Activity-guided fractionation of a chloroform-soluble extract of the leaves of Ormosia sumatrana, using a proteasome inhibition assay, led to the isolation of a new A-type proanthocyanidin derivative, 3'-O-cinnamoylprocyanidin A-2 (1), and a new cerebroside, sumatranoside (2). The structures of these two isolates were determined as epicatechin-(2 beta-->O-->7',4 beta-->8')-epicatechin-3'-O-cinnamate (1) and 1-O-(beta-d-glucopyranosyl)-(2S,3S,4R)-2N-[(2'R)-2'-hydroxy-tetracosanoyl]-9Z-octadecene-1,3,4-triol (2), respectively, by spectroscopic and chemical methods. Sumatranoside (2) exhibited proteasome inhibitory activity with an IC(50) value of 30 microM.
Su
Bao-Ning
BN
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, USA.
Hwang
Bang Yeon
BY
Chai
Heebyung
H
Carcache-Blanco
Esperanza J
EJ
Kardono
Leonardus B S
LB
Afriastini
Johar J
JJ
Riswan
Soedarsono
S
Wild
Robert
R
Laing
Naomi
N
Farnsworth
Norman R
NR
Cordell
Geoffrey A
GA
Swanson
Steven M
SM
Kinghorn
A Douglas
AD
D002392:Catechin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002554:Cerebrosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007887:Fabaceae / Q000737:chemistry*; D007214:Indonesia; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry; D061988:Proteasome Inhibitors; D013237:Stereoisomerism
C494657:3'-O-cinnamoylprocyanidin A-2; D002554:Cerebrosides; D004791:Enzyme Inhibitors; D061988:Proteasome Inhibitors; C494658:sumatranoside; D002392:Catechin