Identification by NMR and accumulation of a neolignan, the dehydrodiconiferyl alcohol-4-β-d-glucoside, in Linum usitatissimum cell cultures

Abstract

Phenylpropanoids represent a broad range of secondary metabolites in plants, in which they are involved in defense mechanisms. This study deals with the NMR identification of a phenylpropanoid, which belongs to the class of neolignans, dehydrodiconiferyl alcohol-4-b-d-glucoside (DCG), in in vitro cultures of Linum usitatissimum. The combination of 1-and 2-D NMR experiments such as COSY, HMBC and HMQC allowed the identification of this compound's structure unambiguously. In order to evaluate its implication in defense mechanism, the L. usitatissimum suspension cells were placed together with fungal extracts. Consequently, the DCG concentration decreased dramatically after 96 h of treatment. In correlation, the phenylcoumaran benzylic ether reductase (PCBER) expression increased rapidly and constantly immediately after elicitation until 96 h post elicitation, as shown by semi-quantitative reverse transcriptase polymerase chain reaction (RT-PCR). These two results are in agreement, since the aglycone form of DCG is one of the two substrates of PCBER, thus suggesting PCBER activation in plant defense mechanisms.

Flavonoids and a neolignan glucoside from Guarea macrophylla (Meliaceae)

“…All the other signals were similar to those reported in the literature for the dehydrodiconiferyl alcohol-4-b-D-glucoside. 13 From a phytochemical standpoint, the Meliaceae family of the Melia and Azadirachta genera has been widely investigated worldwide leading to the isolation of a number of limonoids and other terpenoids with a variety of biological effects. 1,17 However, chemical studies concerning the isolation and identification of phenolic compounds in Meliaceae remain scarce where catechins have been previously reported in Toona and Cedrela genera, 18 flavalignans in Trichillia, 19 flavonols glycosides in Melia and lignans in Walsura and Aglaia.…”

“…1 H, 1D, 2D NMR, 13 C, UV and MS spectra of compounds 1a-1d are available free of charge at http://quimicanova.sbq.org.br as a PDF file.…”

“…10 Therefore, in order to contribute to the study of the phenolic composition in the Meliaceae family, we report the phytochemical analysis of the n-BuOH extract from leaves of G. macrophylla and the identification of flavonoids glycosides (quercetin 3-O-b-D-glucopyranoside, quercetin 3-O-b-D-galactopyranoside, kaempferol 7-O-b-Dglucopyranoside) for the first time in the genus Guarea plus a neolignan glucoside (dehydrodiconiferyl alcohol 4-b-D-glucoside) for the first time in the Meliaceae family. [11][12][13] All compounds were identified by a combination of spectroscopic methods ( 1 H, 1D, 2D NMR, 13 C, UV and MS).…”

Differential accumulation of monolignol-derived compounds in elicited flax (Linum usitatissimum) cell suspension cultures

“…Flax cell cultures have also been shown to accumulate significant amounts of a 8-5'-linked phenylcoumaran lignan (Fig. 1c) as its glucosylated form, the dehydrodiconiferyl alcohol-4-b-D-glucoside (DCG; Attoumbre et al 2005).…”

Pinoresinol–lariciresinol reductase gene expression and secoisolariciresinol diglucoside accumulation in developing flax (Linum usitatissimum) seeds

“…Lewis et al (2001) andvon Heimendahl et al (2005) have cloned and published Xax PLR encoding cDNAs. Previous experiments have led us to clone a number of Xax cDNAs involved in the regulation of phenylpropanoid pathway, amongst which the LuPLR and LuPCBER (Attoumbre et al 2006; AY837829) genes involved in lignan and neolignan metabolism. These two gene sequences were very similar to the sequence published by von Heimendahl et al (2005).…”