Phenolic compounds from the branches of Eucalyptus maideni.

Abstract

Three new phenolic compounds, eucalmaidin F (1), (3S)-5-guaiacyl-3-hydroxypentanoic acid (2), and 8-β-C-glucopyranosyl-5,7-dihydroxy-2-isobutylchromone (3), were isolated from the branches of E. maideni, together with 30 known compounds, including four phenylpropanoids, three lignans, four phloroglucinol glucosides, five dihydroflavonoids, seven simple phenolic compounds, six terpenoids, and glycerol. The new structures were established by spectroscopic studies (MS, and 1D- and 2D-NMR), chemical degradation, and modified Mosher's method. Compounds 3, guaiacylglycerol, 3-hydroxy-1-(4-hydroxyphenyl)propan-1-one, caffeic acid, (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid, (7'S,8R,8'R)-lyoniresinol, (+)-lyoresinol 3α-O-α-L-rhamnopyranoside, garcimangosone, phlorocetophenone 2'-glucopyranoside, (+)-taxifolin 3α-O-α-L-rhamnopyranoside, (+)-aromadendrin, (+)-taxifolin, resveratrol, piceatannol, 3,4,5-trihydroxyphenol. Tachiaside, gallic acid, macrocapals A und G, and oleuropeic acid were evaluated for their cytotoxicities against five human cancer cell lines. Resveratrol, piceatannol, gallic acid, and macrocapal G exhibited moderate inhibitory effects on human myeloid heukemia HL-60 cell, with IC(50) values of 22.05, 22.05, 7.75, and 31.93 μM, respectively; and only macrocapal G showed inhibitory effect on hepatocellular carcinoma SMMC-7721 cell, with an IC(50) value of 26.75 μM.

• Authors: Li-Wen Tian, Min Xu, Yan Li, Xing-Yao Li, Dong Wang, Hong-Tao Zhu, Chong-Ren Yang, Ying-Jun Zhang
• Journal: Chemistry & biodiversity (Chem Biodivers) Vol. 9 Issue 1 Pg. 123-30 (Jan 2012) ISSN: 1612-1880 [Electronic] Switzerland
• PMID: 22253109 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich.

Chemical References

• 8-beta-C-glucopyranosyl-5,7-dihydroxy-2-isobutylchromone
• Chromones
• Flavones
• Phenols
• eucalmaidin F

Topics

• Cell Line, Tumor
• Cell Survival (drug effects)
• Chromones (chemistry, isolation & purification, pharmacology)
• Drug Screening Assays, Antitumor
• Eucalyptus (chemistry)
• Flavones (chemistry, isolation & purification)
• Humans
• Magnetic Resonance Spectroscopy
• Mass Spectrometry
• Molecular Conformation
• Phenols (chemistry, isolation & purification, pharmacology)
• Plant Stems (chemistry)