Structural Diversity in Lignans and Neolignans

Wallis, A. F. A.

doi:10.1021/bk-1998-0697.ch021

Cited by 7 publications

(4 citation statements)

References 57 publications

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“…Only one such protein has been characterized sufficiently to reveal that its activity results in the preferential production of an 8-8-linked coniferyl alcohol dimer (pinoresinol). However, we are unaware of a dirigent protein directing the formation of the most common lignin bond, 8-O-4-linkages between monolignols, despite the occurrence of lignans containing the 8-O-4-linkage (Wallis, 1998); nor are we aware of any evidence for dirigent proteins that result in the formation of lignin. Furthermore, although a polyclonal antibody raised against the dirigent protein reacted with epitopes in vascular tissue of F. suspensa (Davin and Lewis, 2000) is an interesting observation, it is not proof for an actual involve- Figure 3.…”

Section: The Dirigent Protein Modelmentioning

confidence: 99%

Lignin Formation in Plants. The Dilemma of Linkage Specificity

2001

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Section: The Dirigent Protein Modelmentioning

confidence: 99%

Lignin Formation in Plants. The Dilemma of Linkage Specificity

2001

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“…Both lignans and neolignans share similar structural conformation, but they can be easily characterized by difference in (a minor but significant) bonding pattern. Generally, lignans consist of phenylpropane dimers that are bonded through the carbon atoms (C8/C8$) of their side chains, whereas in neolignans, these dimers are connected through bond other than C8/C8$ [3].…”

Section: Introductionmentioning

confidence: 99%

Biogenic zinc oxide nanoparticles-enhanced biosynthesis of lignans and neolignans in cell suspension cultures of Linum usitatissimum L

Abbasi

Zahir

Ahmad

et al. 2019

Artificial Cells, Nanomedicine, and Biotechnology

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Zinc oxide nanoparticles (NPs) have emerged as a novel elicitor for enhanced biosynthesis of secondary metabolites in in vitro plant cell cultures. The current study was aimed to explore elicitation abilities of ZnO-NPs for enhanced accumulation of lignans and neolignans in cell cultures of Linum usitatissimum. We optimized concentration of zinc oxide NPs before carrying out a full-fledged experiment. Subsequently, an optimum dose of 100 mg/l was introduced into the culture medium on day 0, days 0 and 15, and finally days 0 and 25. We observed that repeated elicitation stimulated various parameters and physiological responses in Linum usitatissimum cell cultures than one-time elicitation. Repeated elicitation of cell cultures on day 0 and 15 resulted in highest fresh weight (412.16 g/l) and lignans production (secoisolariciresinol diglucoside 284.12 mg/l: lariciresinol diglucoside 86.97 mg/l). Contrarily, repeated elicitation on day 0 and 25 resulted in highest DW (13.53 g/l), total phenolic production (537.44 mg/l), total flavonoid production (123.83 mg/l) and neolignans production (dehydrodiconiferyl alcohol glucoside 493.28 mg/l: guaiacylglycerol-b-coniferyl alcohol ether glucoside 307.69 mg/l). Enhancement in plant growth and secondary metabolites accumulation was several fold higher than controls. Furthermore, a linear relationship existed between total phenolic and flavonoid contents which in turn was correlated with higher antioxidant activities. ARTICLE HISTORY

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“…[14] Lignans, which represent a coupling of two phenyl propanoids (C 6 -C 3 ) via a C(8) and C(8 0 ) bond, exist in a large group of natural sources. The phenylpropanoids are important intermediates in the synthesis of lignans, as well as styrylpyrones, coumarins, and lignins.…”

Section: Introductionmentioning

confidence: 99%

“…The phenylpropanoids are important intermediates in the synthesis of lignans, as well as styrylpyrones, coumarins, and lignins. [14] Lignans, which represent a coupling of two phenyl propanoids (C 6 -C 3 ) via a C (8) and C(8 0 ) bond, exist in a large group of natural sources. [15] Lignans are transformed to a lot of backbone structures in the lignan pathway, such as enterolactone, enterodiol, monoepoxy, and diepoxy lignans.…”

Section: Introductionmentioning

confidence: 99%

New Lignans from the Flower of Forsythia koreana and Their Suppression Effect on VCAM‐1 Expression in MOVAS Cells

Lee

Jang

Seo

et al. 2018

Chemistry & Biodiversity

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Six lignans including two new lignans were obtained as the principal components of the Forsythia koreana flowers via silica gel (SiO ), octadecyl SiO (ODS) as well as Sephadex LH-20 column chromatography. In addition to two new lignans, named koreanaside A ((7R,8S,7'R,8'S)-7,7'-diepoxy-5'-hydroxy-3,3'-dimethoxylignan 4-O-β-d-glucopyranoside) and koreanaside B ((7R,8S,7'S,8'R)-7,9'-epoxy-9,5',7'-trihydroxy-3,3'-dimethoxylignan 4-O-β-d-glucopyranoside), four known lignans were identified to be (+)-phylligenin, (-)-epipinoresinol, pinoresinol, and tinosposide A. The structures and absolute configurations of koreanasides A and B were established by means of analysis of spectroscopic data (NMR, IR, FAB-MS, and CD), whereas the structures of known lignans were identified by comparison their NMR and MS values with those in the reported literature. Their chemical structures including configuration were established by means of analysis of spectroscopic data (NMR, IR, FAB-MS, and CD) but also comparison of their NMR and MS values with those in the reported literature. This is the first article for isolation of six lignans of F. koreana flowers. Koreanasides A and B showed high radical scavenging activity with oxygen radical absorbance capacity (ORAC) values of 0.97 ± 0.01 and 1.02 ± 0.01, respectively. Koreanaside A also prohibited expressing VCAM-1 in MOVAS cells with 80.5% at 25 mg/mL.

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Structural Diversity in Lignans and Neolignans

Cited by 7 publications

References 57 publications

Lignin Formation in Plants. The Dilemma of Linkage Specificity

Lignin Formation in Plants. The Dilemma of Linkage Specificity

Biogenic zinc oxide nanoparticles-enhanced biosynthesis of lignans and neolignans in cell suspension cultures of Linum usitatissimum L

New Lignans from the Flower of Forsythia koreana and Their Suppression Effect on VCAM‐1 Expression in MOVAS Cells

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