title: Bioactive 6S-styryllactone constituents of Polyalthia parviflora.
abstract: Parvistones A-E (1-5), five new styryllactones possessing a rare α,β-lactone moiety and a 6S configuration, were isolated from a methanolic extract of Polyalthia parviflora leaves. The structures and the absolute configuration of the isolates were elucidated using NMR spectroscopy, specific rotation, circular dichroism, and X-ray single-crystal analysis. Compounds 8, 9, 11, and 12 were isolated for the first time. The results were supported by comparing the data measured to those of 6R-styryllactones. Moreover, a plausible biogenetic pathway of the isolated compounds was proposed. The structure-activity relationship of the compounds in an in vitro anti-inflammatory assay revealed the 6S-styryllactones to be more potent than the 6R derivatives. However, the effect was opposite regarding their cytotoxic activity. In addition, 6S-styrylpyrones isolated showed more potent anti-inflammatory and cytotoxic activity when compared to the 1S-phenylpyranopyrones obtained.
authors.affiliation: Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University , Kaohsiung 807, Taiwan.
authors.forename: Jing-Ru
authors.initials: JR
authors.lastname: Liou
authors.forename: Tung-Ying
authors.initials: TY
authors.lastname: Wu
authors.forename: Tran Dinh
authors.initials: TD
authors.lastname: Thang
authors.forename: Tsong-Long
authors.initials: TL
authors.lastname: Hwang
authors.forename: Chin-Chun
authors.initials: CC
authors.lastname: Wu
authors.forename: Yuan-Bin
authors.initials: YB
authors.lastname: Cheng
authors.forename: Michael Y
authors.initials: MY
authors.lastname: Chiang
authors.forename: Yu-Hsuan
authors.initials: YH
authors.lastname: Lan
authors.forename: Mohamed
authors.initials: M
authors.lastname: El-Shazly
authors.forename: Shwu-Li
authors.initials: SL
authors.lastname: Wu
authors.forename: Ludger
authors.initials: L
authors.lastname: Beerhues
authors.forename: Shyng-Shiou
authors.initials: SS
authors.lastname: Yuan
authors.forename: Ming-Feng
authors.initials: MF
authors.lastname: Hou
authors.forename: Shu-Li
authors.initials: SL
authors.lastname: Chen
authors.forename: Fang-Rong
authors.initials: FR
authors.lastname: Chang
authors.forename: Yang-Chang
authors.initials: YC
authors.lastname: Wu
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D031044:Polyalthia / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014744:Vietnam
chemical_list: D000893:Anti-Inflammatory Agents; D007783:Lactones