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Chalcones from Angelica keiskei: Evaluation of Their Heat Shock Protein Inducing Activities.
J Nat Prod. 2015 Oct 23; 78(10):2481-7.JN

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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Kil YS
College of Pharmacy, Graduate School of Pharmaceutical Sciences, Ewha Womans University , Seoul 120-750, Korea.
Choi SK
College of Pharmacy, Graduate School of Pharmaceutical Sciences, Ewha Womans University , Seoul 120-750, Korea.
Lee YS
College of Pharmacy, Graduate School of Pharmaceutical Sciences, Ewha Womans University , Seoul 120-750, Korea.
Jafari M
Department of Pharmaceutical Sciences, University of California , Irvine, California 92697, United States.
Seo EK
College of Pharmacy, Graduate School of Pharmaceutical Sciences, Ewha Womans University , Seoul 120-750, Korea.

MeSH

AngelicaBlotting, WesternCell SurvivalChalconeChalconesHSP27 Heat-Shock ProteinsHSP70 Heat-Shock ProteinsHeat-Shock ProteinsIntracellular Signaling Peptides and ProteinsMolecular StructurePlant Components, AerialPolymerase Chain ReactionProtein Serine-Threonine KinasesRepublic of Korea

Pub Type(s)

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

Language

eng

PubMed ID

26431394

Citation

Kil, Yun-Seo, et al. "Chalcones From Angelica Keiskei: Evaluation of Their Heat Shock Protein Inducing Activities." Journal of Natural Products, vol. 78, no. 10, 2015, pp. 2481-7.
Kil YS, Choi SK, Lee YS, et al. Chalcones from Angelica keiskei: Evaluation of Their Heat Shock Protein Inducing Activities. J Nat Prod. 2015;78(10):2481-7.
Kil, Y. S., Choi, S. K., Lee, Y. S., Jafari, M., & Seo, E. K. (2015). Chalcones from Angelica keiskei: Evaluation of Their Heat Shock Protein Inducing Activities. Journal of Natural Products, 78(10), 2481-7. https://doi.org/10.1021/acs.jnatprod.5b00633
Kil YS, et al. Chalcones From Angelica Keiskei: Evaluation of Their Heat Shock Protein Inducing Activities. J Nat Prod. 2015 Oct 23;78(10):2481-7. PubMed PMID: 26431394.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Chalcones from Angelica keiskei: Evaluation of Their Heat Shock Protein Inducing Activities. AU - Kil,Yun-Seo, AU - Choi,Seul-Ki, AU - Lee,Yun-Sil, AU - Jafari,Mahtab, AU - Seo,Eun-Kyoung, Y1 - 2015/10/02/ PY - 2015/10/3/entrez PY - 2015/10/3/pubmed PY - 2016/2/13/medline SP - 2481 EP - 7 JF - Journal of natural products JO - J Nat Prod VL - 78 IS - 10 N2 - 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. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/26431394/Chalcones_from_Angelica_keiskei:_Evaluation_of_Their_Heat_Shock_Protein_Inducing_Activities_ DB - PRIME DP - Unbound Medicine ER -