Phenolic compounds and their anti-oxidative properties and protein kinase inhibition from the Chinese mangrove plant Laguncularia racemosa.
Phenolic compounds, named integracin D (1), (7'R, 8'S, 8S)-8-hydroxyisoguaiacin (3), (2R, 3R) pinobanksin-3-caffeoylate (5) and threo-8S-7-methoxysyringylglycerol (6), respectively, were isolated from the Chinese mangrove plant Laguncularia racemosa (L) Gaertn. f. (Combretaceae), together with 23 known phenolic metabolites. Their structures were elucidated on the basis of extensive spectroscopic analyses including that of IR, UV, MS, CD, 1D and 2D NMR spectra as well as by comparison with literature data. Compound 5 showed significant anti-oxidative activity in the DPPH and TEAC free-radical-scavenging assays, while several of the phenolic compounds were tested for protein kinase inhibitory activity in an assay involving 24 different human tumor related protein kinases. Compounds 5, 7, and 23 showed potential inhibition with IC(50) values between 2.2 and 3.6microg/mL toward individual kinases. The ellagic acid derivatives were tested for insecticidal activity.
Shi
Cui
C
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100083, PR China.
Xu
Min-Juan
MJ
Bayer
Mirko
M
Deng
Zhi-Wei
ZW
Kubbutat
Michael H G
MH
Wätjen
Wim
W
Waejen
Wim
W
Proksch
Peter
P
Lin
Wen-Han
WH
D000818:Animals; D000975:Antioxidants / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000737:chemistry; D045744:Cell Line, Tumor; D029764:Combretaceae / Q000737:chemistry*; D006801:Humans; D008958:Models, Molecular; D008968:Molecular Conformation; D009369:Neoplasms / Q000201:enzymology; D019800:Phenol / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D010851:Picrates / Q000737:chemistry; D047428:Protein Kinase Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D051381:Rats; D018411:Spodoptera / Q000187:drug effects
D000975:Antioxidants; D001713:Biphenyl Compounds; D010851:Picrates; D047428:Protein Kinase Inhibitors; D019800:Phenol; C004931:1,1-diphenyl-2-picrylhydrazyl