title: Chalcones from Angelica keiskei: Evaluation of Their Heat Shock Protein Inducing Activities.
abstract: Five new chalcones, 4,2',4'-trihydroxy-3'-[(2E,5E)-7-methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1), (±)-4,2',4'-trihydroxy-3'-[(2E)-6-hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2), 4,2',4'-trihydroxy-3'-[(2E)-3-methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3), 2',3'-furano-4-hydroxy-4'-methoxychalcone (4), and (±)-4-hydroxy-2',3'-(2,3-dihydro-2-methoxyfurano)-4'-methoxychalcone (5), were isolated from the aerial parts of Angelica keiskei Koidzumi together with eight known chalcones, 6-13, which were identified as (±)-4,2',4'-trihydroxy-3'-[(6E)-2-hydroxy-7-methyl-3-methylene-6-octenyl]chalcone (6), xanthoangelol (7), xanthoangelol F (8), xanthoangelol G (9), 4-hydroxyderricin (10), xanthoangelol D (11), xanthoangelol E (12), and xanthoangelol H (13), respectively. Chalcones 1-13 were evaluated for their promoter activity on heat shock protein 25 (hsp25, murine form of human hsp27). Compounds 1 and 6 activated the hsp25 promoter by 21.9- and 29.2-fold of untreated control at 10 μM, respectively. Further protein expression patterns of heat shock factor 1 (HSF1), HSP70, and HSP27 by 1 and 6 were examined. Compound 6 increased the expression of HSF1, HSP70, and HSP27 by 4.3-, 1.5-, and 4.6-fold of untreated control, respectively, without any significant cellular cytotoxicities, whereas 1 did not induce any expression of these proteins. As a result, 6 seems to be a prospective HSP inducer.
authors.affiliation: College of Pharmacy, Graduate School of Pharmaceutical Sciences, Ewha Womans University , Seoul 120-750, Korea.
authors.forename: Yun-Seo
authors.initials: YS
authors.lastname: Kil
authors.affiliation: College of Pharmacy, Graduate School of Pharmaceutical Sciences, Ewha Womans University , Seoul 120-750, Korea.
authors.forename: Seul-Ki
authors.initials: SK
authors.lastname: Choi
authors.affiliation: College of Pharmacy, Graduate School of Pharmaceutical Sciences, Ewha Womans University , Seoul 120-750, Korea.
authors.forename: Yun-Sil
authors.initials: YS
authors.lastname: Lee
authors.affiliation: Department of Pharmaceutical Sciences, University of California , Irvine, California 92697, United States.
authors.forename: Mahtab
authors.initials: M
authors.lastname: Jafari
authors.affiliation: College of Pharmacy, Graduate School of Pharmaceutical Sciences, Ewha Womans University , Seoul 120-750, Korea.
authors.forename: Eun-Kyoung
authors.initials: EK
authors.lastname: Seo
mesh_terms: D029969:Angelica / Q000737:chemistry*; D015153:Blotting, Western; D002470:Cell Survival / Q000187:drug effects; D002599:Chalcone / Q000031:analogs & derivatives; D047188:Chalcones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D055551:HSP27 Heat-Shock Proteins / Q000187:drug effects; D018840:HSP70 Heat-Shock Proteins; D006360:Heat-Shock Proteins / Q000187:drug effects*; D047908:Intracellular Signaling Peptides and Proteins / Q000187:drug effects; D015394:Molecular Structure; D035261:Plant Components, Aerial / Q000737:chemistry; D016133:Polymerase Chain Reaction; D017346:Protein Serine-Threonine Kinases / Q000187:drug effects; D056910:Republic of Korea; D000099190:MAP-Kinase-Activated Kinase 2
chemical_list: D002599:Chalcone; D047188:Chalcones; D055551:HSP27 Heat-Shock Proteins; D018840:HSP70 Heat-Shock Proteins; D006360:Heat-Shock Proteins; D047908:Intracellular Signaling Peptides and Proteins; D017346:Protein Serine-Threonine Kinases; D000099190:MAP-Kinase-Activated Kinase 2; C068244:xanthoangelol