title: Diarylheptanoids from the seeds of Alpinia katsumadai as heat shock factor 1 inducers.
abstract: Seven new diarylheptanoids, (-)-(R)-4″-hydroxyyashabushiketol (1), (3S,5S)-alpinikatin (2), katsumain C (3), 7-epi-katsumain C (4), ent-alpinnanin B (5), ent-alpinnanin A (6), and ent-calyxin H (8), were isolated from the EtOAc extract of the seeds of Alpinia katsumadai together with three known compounds, alpinnanin B (7), epicalyxin H (9), and calyxin H (10). Each isomer mixture of 3 and 4, 5-7, and 8-10 was separated successfully by preparative HPLC using a chiral column. The three isomer mixtures (3 and 4, 5-7, 8-10) at 1 μM increased expression of heat shock factor 1 (HSF1) with fold increases of 1.438, 1.190, and 1.316, respectively, which was accompanied with increased expression of heat shock protein (HSP) 27 (1.403-, 1.250-, and 1.270-fold, respectively) and HSP70 (1.373-, 1.313-, and 1.229-fold, respectively) without cellular cytotoxicity, suggesting a possible application of these compounds as HSP inducers. Celastrol was used as a positive control of HSP induction, producing fold increases of 1.066 (HSF1), 1.216 (HSP27), and 1.371 (HSP70) at 1 μM. Compounds 1 and 2 did not affect the induction of HSF1 protein.
authors.affiliation: The Center for Cell Signaling & Drug Discovery Research, College of Pharmacy, Ewha Womans University, Seoul 120-750, Korea.
authors.forename: Joo-Won
authors.initials: JW
authors.lastname: Nam
authors.forename: Ga-Young
authors.initials: GY
authors.lastname: Kang
authors.forename: Ah-Reum
authors.initials: AR
authors.lastname: Han
authors.forename: Dongho
authors.initials: D
authors.lastname: Lee
authors.forename: Yun-Sil
authors.initials: YS
authors.lastname: Lee
authors.forename: Eun-Kyoung
authors.initials: EK
authors.lastname: Seo
mesh_terms: D032429:Alpinia / Q000737:chemistry*; D004268:DNA-Binding Proteins / Q000187:drug effects; D036381:Diarylheptanoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018840:HSP70 Heat-Shock Proteins / Q000187:drug effects*; D000076249:Heat Shock Transcription Factors; D015394:Molecular Structure; D056910:Republic of Korea; D012639:Seeds / Q000737:chemistry; D014157:Transcription Factors / Q000187:drug effects
chemical_list: D004268:DNA-Binding Proteins; D036381:Diarylheptanoids; D018840:HSP70 Heat-Shock Proteins; D000076249:Heat Shock Transcription Factors; D014157:Transcription Factors