Biphenyl-Type Neolignan Derivatives from the Twigs of Magnolia denudata and Their Anti-Inflammatory Activity.
Two new biphenyl-type neolignan derivatives, 2-[2-(hydroxymethyl)-1-benzofuran-5-yl]-4-(prop-2-en-1-yl)phenol (1) and 2'-ethoxy-5,5'-di(prop-2-en-1-yl)biphenyl-2-ol (2), were isolated from the twigs of Magnolia denudata, together with six known compounds (3-8). The structures of 1 and 2 were determined through extensive 1D- and 2D-NMR and mass-spectrometric analyses. Magnolol (6) and honokiol (7) exhibited potent inhibition (IC50 values=4.4±0.2 and 0.71±0.13 μg/ml, resp.) of O$\rm{{_{2}^{{^\cdot} -}}}$ generation by human nutrophils in response to N-formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). In addition, 2-[2-(hydroxymethyl)-1-benzofuran-5-yl]-4-(prop-2-en-1-yl)phenol (1), 2'-ethoxy-5,5'-di(prop-2-en-1-yl)biphenyl-2-ol (2), magnolol (6), and vanillic acid (8) inhibited fMLP/CB-induced elastase release with IC50 values=6.4±1.5, 2.4±0.4, 1.5±0.2, and 4.8±0.5 μg/ml, respectively.
School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Ching-Yi
CY
Chung
Chung-Jen Junior College of Nursing, Health Sciences and Management, Chiayi 600, Taiwan.
Wen-Lung
WL
Kuo
Graduate Institute of Natural Products, Chang Gung University, Taoyuan 333, Taiwan.
Tsong-Long
TL
Hwang
School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Mei-Ing
MI
Chung
Department of Pharmacy & Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung 907, Taiwan, (phone: +886-8-7624002 ext. 2827; fax: +886-8-7624002 ext. 5121). jjchen@tajen.edu.tw.
Jih-Jung
JJ
Chen
D000328:Adult; D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D017705:Lignans / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D031566:Magnolia / Q000737:chemistry*; D009504:Neutrophils / Q000187:drug effects / Q000276:immunology; D013481:Superoxides / Q000276:immunology; D055815:Young Adult
D000893:Anti-Inflammatory Agents; D001713:Biphenyl Compounds; D017705:Lignans; D013481:Superoxides
Anti-Inflammatory activity; Biphenyl-type neolignan; Magnolia denudata