Elsevier

Phytochemistry

Volume 10, Issue 9, September 1971, Pages 2249-2251
Phytochemistry

Fagaceae
Phenolics of Quercus rubra wood

https://doi.org/10.1016/S0031-9422(00)97238-8Get rights and content

Abstract

Sixteen phenolics are positively identified in oak wood; seven had not been reported in oaks. Several additional phenolics are tentatively identified. Bark is briefly investigated. Lyoniside is shown to be lyoniresinol 2a-O-xyloside.

References (6)

  • M.K. Seikel et al.

    Phytochem.

    (1970)
  • F.D. Hostettler et al.

    Tetrahedron

    (1969)
  • A.J. Russell

    J. Amer. Leather Chem. Assoc.

    (1944)
There are more references available in the full text version of this article.

Cited by (48)

  • Contribution of oak lignans to wine taste: Chemical identification, sensory characterization and quantification

    2015, Tetrahedron
    Citation Excerpt :

    The 1H and 13C NMR data were found to be similar to those already reported in the literature for lyoniresinol.35–38 The presence of lyoniresinol has been established in Quercus rubra wood39 but also in spirits17–19 and wines8 aged in oak barrels, and it is known for its anti-mutagenic and anti-oxidative activities.40,41 Vivas42 claimed that lyoniresinol has a red vermillion colour.

  • Tannin analysis of chestnut bark samples (Castanea sativa Mill.) by HPLC-DAD-MS

    2014, Food Chemistry
    Citation Excerpt :

    Peak 3 (Fig. 1 B) was assigned to gallic acid thanks to both molecular ion [M−H]− and the ion at m/z 125.0 generated from the loss of a CO2 group from the carboxylic acid moiety [M−H−CO2]−. The presence of gallic acid in chestnut bark extracts might be quite questionable (Canas, Leandro, Spranger, & Belchior, 1999); moreover the occurrence of gallotannins in wood cannot be excluded (Seikel, Hostettler, & Niemann, 1971; Vivas, Chauvet, Sudraud, et al., 1993), although it has never been confirmed. An acceptable hypothesis (Canas et al., 1999) suggests that gallic acid has derived from the hydrolysis of some galloyl esters associated with the parietal composites of chestnut cells (Viriot et al., 1994).

  • COX-2 inhibitory activity of homoisoflavanones and xanthones from the bulbs of the Southern African Ledebouria socialis and Ledebouria ovatifolia (Hyacinthaceae: Hyacinthoideae)

    2013, Phytochemistry
    Citation Excerpt :

    The dichloromethane extract yielded compound 2, reported previously (Kawasaki et al., 1973) as a mixture of diastereomers, which we separated after acetylation and were able to assign the respective absolute configurations using 2D NMR and CD spectroscopy, a novel dihydro-chalcone (3), and a novel xanthone (4). Also isolated from this extract were the known compounds (R)-5,7-dihydroxy-3-(4′-hydroxybenzyl)chroman-4-one (Adinolfi et al., 1987) and (E)-4,4′-dihydroxy-2′,6′-dimethoxychalcone (Sun et al., 1989) which had both been isolated previously from L. ovatifolia (Pohl et al., 2001), scillascillin (Kawasaki et al., 1973), 1,6-dihydroxy-3-methoxy-8-methyl-9H-xanthen-9-one (McMaster et al., 1960; Mutanyatta et al., 2003), (R)-4′,5,7-trihydroxy-3′-methoxyspiro{2H-1-benzopyran-3(4H)-9-bicyclo[4.2.0]octa[1,3,5]triene}-4-one (Adinolfi et al., 1985), (R)-3′,5,7-trihydroxy-4′-methoxyspiro{2H-1-benzopyran-3(4H)-9-bicyclo[4.2.0]octa[1,3,5]triene}-4-one (Adinolfi et al., 1987), (R)-5,7-dihydroxy-3-(4′-methoxybenzyl)chroman-4-one (Heller et al., 1976), eucomol (Bohler and Tamm, 1967), and (R)-7-hydroxy-3-(4′-hydroxybenzyl)-5-methoxychroman-4-one (Finckh and Tamm, 1970) which had been isolated previously from the Hyacinthaceae, and coniferaldehyde (Seikel et al., 1971) and chondrillasterol (Bergmann and Feeney, 1948) which had not been isolated previously from this family. The ethyl acetate extract yielded one novel homoisoflavanone, ovatifolionone (5), and the known compounds, drimiopsin C (Mulholland et al., 2004), norlichexanthone (Aghoramurthy and Seshadri, 1953; Mutanyatta et al., 2003), 22-acetoxy-15-deoxoeucosterol (Amschler et al., 1997; Pohl et al., 2001), (R)-(3-(3′,4′-dihydroxybenzyl)-5,7-dihydroxychroman-4-one (Adinolfi et al., 1987, 4′-demethyl-5-O-methyl-dihydroeucomin (Finckh and Tamm, 1970), (R)-3-(3′,4′-dihydroxybenzyl)-7-hydroxy-5-methoxychroman-4-one (Adinolfi et al., 1987), and (E)-3-(3′,4′-dihydroxybenzylidene)-7-hydroxy-5-methoxychroman-4-one (Masterova et al., 1991) which have all been isolated from the Hyacinthaceae previously and p-anisic aldehyde (Gottlieb et al., 1970) and 4-hydroxyphenylethanol (Gharbo et al., 1970) which have not been reported from this family.

  • Origin of brown discoloration in the staves of oak used in cooperage - Characterization of two new lignans in oak wood barrels

    2009, Comptes Rendus Chimie
    Citation Excerpt :

    Their ions (Fig. 2) at m/z 708, 619, 587, 515, 354, 289, 239 were characteristic of this lignan. The lyoniresinol was identified by Seikel et al. [12] in Quercus rubra wood and by Nabeta et al. [13] in Quercus robur wood. Vivas characterized this lignan in extracts of Q. petraea wood [6] and also demonstrated the presence of two forms of lyoniresinol in these extracts.

View all citing articles on Scopus
1

Deceased. See Phytochem. 9, 679 (1970). Reprint requests and correspondence should be addressed to Dr. John W. Rowe at the U.S. Forest Products Laboratory.

2

Present address: Botanical Laboratory, State University of Utrecht, Utrecht, The Netherlands.

View full text