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Phenolic Compounds from the Branches of Eucalyptus maideni
Author(s) -
Tian LiWen,
Xu Min,
Li Yan,
Li XingYao,
Wang Dong,
Zhu HongTao,
Yang ChongRen,
Zhang YingJun
Publication year - 2012
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201100021
Subject(s) - gallic acid , chemistry , piceatannol , caffeic acid , taxifolin , stereochemistry , terpene , resveratrol , terpenoid , syringic acid , organic chemistry , antioxidant , biochemistry , flavonoid
Three new phenolic compounds, eucalmaidin F ( 1 ), (3 S )‐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, (2 E )‐3‐(4‐hydroxyphenyl)prop‐2‐enoic acid, (7′ S ,8 R ,8′ R )‐lyoniresinol, (+)‐lyoresinol 3 α ‐ O ‐ α ‐ L ‐rhamnopyranoside, garcimangosone, phlorocetophenone 2′‐glucopyranoside, (+)‐taxifolin 3 α ‐ 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 μ M , respectively; and only macrocapal G showed inhibitory effect on hepatocellular carcinoma SMMC‐7721 cell, with an IC 50 value of 26.75 μ M .