Structure–Plant Growth Inhibitory Activity Relationship of Lariciresinol

Yamauchi, Satoshi; Kumamoto, Mitsuko; Ochi, Yuki; Nishiwaki, Hisashi; Shuto, Yoshihiro

doi:10.1021/jf404292w

Cited by 15 publications

(11 citation statements)

References 22 publications

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“…In addition, a methyl group signal at δ 0.85 (3H, d, J = 7.0 Hz) and two methoxy group singlets at δ 3.92 and 3.97 were used to construct the 4,4′-dihydroxy-3,3′-dimethoxy-7,9′-epoxylignan-7′-one basic unit, which was verified by HMBC correlations from H-2 to C-4, C-6, C-7; from H-6 to C-2, C-4, C-7; from H-2′ to C-4′, C-6′; from H-6′ to C-2′, C-4′; from H-7′ to C-2′, C-6′; from H-9a to C-7, C-7′, C-8; and from CH 3 -9′ to C-7′, C-8, C-8′, respectively (Figure ). The configurations of C-7′, C-8, and C-8′ were determined as rel -(7 R , 8′ R , 8 S ) by the 1 H NMR coupling constants, the Cotton effects in the electronic circular dichroism (ECD) spectrum (Supporting Information), and NOE cross-peaks of H-7′/CH 3 -9′ and H-8/H-8′ in the NOESY spectroscopic analysis. − Therefore, 9 was established as shown in Figure and given the trivial name rel -(7 R ,8′ R ,8 S )-forsythialan C following the previous convention …”

Section: Resultsmentioning

confidence: 99%

Chemical Constituents and Anti-inflammatory Principles from the Fruits of Forsythia suspensa

et al. 2017

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Fifty compounds were isolated from the fruits of Forsythia suspensa, including 13 new compounds characterized as eight new diterpenoids (1-8), three new lignans (9-11), a new iridoid (12), and a new triterpenoid (13). Their structures were established on the basis of spectroscopic and spectrometric analysis. Most of the isolated compounds were examined for their anti-inflammatory activity in vitro. The results showed that several compounds displayed significant inhibition of fMLP/CB-induced superoxide anion generation and elastase release, with IC values ranging from 0.6 ± 0.1 to 8.6 ± 0.8 μg/mL and from 0.8 ± 0.3 to 7.3 ± 1.1 μg/mL, respectively.

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Section: Resultsmentioning

confidence: 99%

Chemical Constituents and Anti-inflammatory Principles from the Fruits of Forsythia suspensa

et al. 2017

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“…Both (+)-lariciresinol and (−)-lariciresinol have been found in nature, but they have different physicochemical property89 and biological activities1011. Antioxidant properties of (+)-lariciresinol on lipid peroxidation12, peroxy radical13, and superoxide radical14 were demonstrated previously.…”

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confidence: 87%

Antioxidant efficacy and the upregulation of Nrf2-mediated HO-1 expression by (+)-lariciresinol, a lignan isolated from Rubia philippinensis, through the activation of p38

Bajpai

Alam

Quan

et al. 2017

Sci Rep

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The aim of the present study was to examine the antioxidative activity of (+)-lariciresinol (LRSL), an optically active lignan isolated from Rubia philippinensis in several in vitro assays. LRSL was also subjected to evaluate its inhibitory effect against the generation of reactive oxygen species (ROS) in murine macrophage (RAW 264.7) cells. The results showed that LRSL possessed very strong radical scavenging activity and reducing power, as well as inhibited ROS generation in a dose-dependent manner without showing any cytotoxicity. The transcriptional and translational levels of superoxide dismutase (SOD), glutathione peroxidase (GPx) and catalase (CAT) were markedly higher in the sample treated group. LRSL treatment also increased the transcriptional and translational activities of NF-E2-related factor-2 (Nrf-2) with a corresponding increase in the transcriptional and translational activities of the heme oxygenase-1 (HO-1). LRSL activated p38 and treatments with SB239063 (a p38 inhibitor) suppressed the LRSL-induced activation of Nrf2, resulting in a decrease in HO-1 expression. Collectively, the data demonstrated that LRSL has potent antioxidative activity, decreasing ROS generation in RAW 264.7 cells and increasing the transcriptional and translational levels of antioxidant enzymes by activating Nrf2-mediated HO-1 induction via p38 signaling.

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“…PDG is preferentially accumulated in young internodes (TOP and MID) and leaves, rather than older tissue (BOT) and roots, suggesting a possible role of PDG in the regulation of plant development. This is particularly relevant if one considers that, on the one hand, lignans were shown to affect plant growth [51,52,53] and, on the other hand, that fibre cells in the TOP and MID internodes are in the rapid elongation phase under a strict control involving gene regulatory network, reactive oxygen species and secondary metabolites [30].…”

Section: Discussionmentioning

confidence: 99%

Insights into Lignan Composition and Biosynthesis in Stinging Nettle (Urtica dioica L.)

et al. 2019

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Stinging nettle (Urtica dioica L.) has been used as herbal medicine to treat various ailments since ancient times. The biological activity of nettle is chiefly attributed to a large group of phenylpropanoid dimers, namely lignans. Despite the pharmacological importance of nettle lignans, there are no studies addressing lignan biosynthesis in this plant. We herein identified 14 genes encoding dirigent proteins (UdDIRs) and 3 pinoresinol-lariciresinol reductase genes (UdPLRs) in nettle, which are two gene families known to be associated with lignan biosynthesis. Expression profiling of these genes on different organs/tissues revealed a specific expression pattern. Particularly, UdDIR7, 12 and 13 displayed a remarkable high expression in the top internode, fibre tissues of bottom internodes and roots, respectively. The relatively high expression of UdPLR1 and UdPLR2 in the young internodes, core tissue of bottom internode and roots is consistent with the high accumulation of lariciresinol and secoisolariciresinol in these tissues. Lignan quantification showed a high abundance of pinoresinol in roots and pinoresinol diglucosides in young internodes and leaves. This study sheds light on lignan composition and biosynthesis in nettle, providing a good basis for further functional analysis of DIRs and PLRs and, ultimately, engineering lignan metabolism in planta and in cell cultures.

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Structure–Plant Growth Inhibitory Activity Relationship of Lariciresinol

Cited by 15 publications

References 22 publications

Chemical Constituents and Anti-inflammatory Principles from the Fruits of Forsythia suspensa

Chemical Constituents and Anti-inflammatory Principles from the Fruits of Forsythia suspensa

Antioxidant efficacy and the upregulation of Nrf2-mediated HO-1 expression by (+)-lariciresinol, a lignan isolated from Rubia philippinensis, through the activation of p38

Insights into Lignan Composition and Biosynthesis in Stinging Nettle (Urtica dioica L.)

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