New diarylpropanoids from Lindera glauca Bl. heartwood

Abstract

From the heartwood of Lindera glauca Blume three new diarylpropanoids have been isolated and identifi ed, which were named lindeglaucol, lindeglaucone, and lindeglaucoside A. Chipped heartwood was extracted repeatedly with 80 % aqueous methanol (MeOH) at room temperature, and the concentrated methanolic extract was successively partitioned with ethyl acetate (EtOAc), n -butanol, and H 2 O. From the EtOAc fraction, three new diarylpropanoids and a known chalconoid were isolated through repeated column chromatography with silica gel, octadecyl silica gel, and Sephadex LH-20. The chemical structures of the compounds were elucidated by interpretation of extensive spectroscopic data such as nuclear magnetic resonance, fast atom bombardment mass spectroscopy, and infrared. In addition, a known chalconoid, cilicicone B, was isolated for the fi rst time from the heartwood of L. glauca .

Flavonoids from Lindera glauca Blume as low-density lipoprotein oxidation inhibitors

“…The chemical structures of the isolated flavonoids were determined spectroscopically by means of IR, EI/MS, FAB/MS and NMR data as shown in Figure 1. Compounds 1 -8 were identified as lindeglaucol (1), lindeglaucone (2), cilicicone B (3), tamarixetin 3-O-a-Lrhamnoside (4), procyanidin A2 (5), cinnamtannin B1 (6), cinnamtannin D1 (7) and procyanidin A1 (8) with confirmation by comparing their spectroscopic data with those in the literature (Nonaka et al 1983;Kamiya et al 2001;Son et al 2005;Ahmed & Al-Howiriny 2007;Koerner et al 2009;Tomochika et al 2011;Huh et al 2012). …”

“…Subsequently, extracts from other Lindera species such as Lindera umbellate and Lindera fruticosa have been reported to counteract LDL-oxidation, and procyanidin A2 is an inhibitor of LDL-oxidation (Katsube et al 2004;Song et al 2006;Hsieh et al 2008). Our own recent study of the heartwood of this plant revealed the chemical structure of four diarylpropanoids and three steroids (Huh et al 2011(Huh et al , 2012. In this study, five flavonoids were additionally isolated and identified from L. glauca heartwood.…”

“…Consequently, compounds 2, 3 and 5-8 expressed high inhibitory activities with IC 50 values of 10.0, 11.3, 5.6, 2.0, 1.1 and 2.2 mg/mL with inhibition of 69.2^2.0, 62.9^0.5, 65.2^0.3, 65.0^0.2, 65.2^0.3 and 61.9^0.7% at 2 mg/mL of BHT, respectively; compounds 1 and 4 expressed moderate activity with inhibition of 72.9^0.1% and 42.7^2.1% at 80 mg/mL, respectively. Diarylpropanoids belong to an unusual category of flavonoids (Huh et al 2012). In previous reports, several diarylpropanoids were isolated from the Lindera genus in the family Lauraceae (Ko et al 2010;Huh et al 2012).…”

“…Diarylpropanoids belong to an unusual category of flavonoids (Huh et al 2012). In previous reports, several diarylpropanoids were isolated from the Lindera genus in the family Lauraceae (Ko et al 2010;Huh et al 2012). Catechin and epicatechin were also reported as LDL-antioxidants in human hepatoma HepG2 and intestinal Caco2 cell lines (Yasuda et al 2011).…”

A new cis-p-coumaroyl flavonol glycoside from the inner barks of Sophora japonica L.

“…The investigation of such naturally bioactive compounds isolated from tree residue is a permanent attraction and challenge, which still leads to new discoveries ( Huh et al 2012 ;Smeds et al 2012 ;da Silva et al 2013 ;Dedic et al 2014 ;In et al 2014 ;Latva-Maenpaa et al 2014 ;Vek et al 2014 ).…”