• Archives of Pharmacal Research
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• v.29 no.7
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• pp.563-565
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• 2006

Potential anti-Helicobacter pylori agent dehydrodiconiferyl alcohol was synthesized in 44% overall yield, starting from vanillin which could be commercially available. Carbon extension of vanillin followed by the Horner-Wadsworth-Emmons reaction, a biomolecular radical coupling reaction and DIBAL-H reduction gave dehydrodiconiferyl alcohol.

• Archives of Pharmacal Research
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• v.27 no.3
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• pp.287-290
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• 2004

Five known lignans, (+)-pinoresinol (1), (+)-8-hydroxypinoresinol (2), (-)- dehydrodiconiferyl alcohol (3), (+)-trans-dehydrodiconiferyl alcohol (4), and (-)-olivil (5), were isolated from the roots of Rosa multiflora for the first time. Their structures were determined using spectroscopic data.

• Natural Product Sciences
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• v.22 no.1
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• pp.53-59
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• 2016

Anti-inflammatory effects of dihydrobenzofuran neolignans isolated from Euonymus alatus leaves and twigs were evaluated in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. Six neolignans, (+)-simulanol (1), (+)-dehydrodiconiferyl alcohol (2), (-)-simulanol (3), (-)-dehydrodiconiferyl alcohol (4), (+)-dihydrodehyrodiconiferyl alcohol (5), threo-buddlenol B (6) effectively inhibited the production of nitric oxide (NO) induced by LPS, and the activity of iNOS. (-)-dehydrodiconiferyl alcohol (4), which showed the most potent inhibitory activity, attenuated the activity of iNOS enzyme and also the expression of iNOS and COX-2 proteins. The subsequent production of pro-inflammatory cytokines, interleukin-$1{\beta}$, interleukin-6, tumor necrosis factor-${\alpha}$ and prostaglandin E2 were also inhibited by the pretreatment of RAW264.7 cells with (-)-dehydrodiconiferyl alcohol (4). These neolignans are thought to contribute to anti-inflammatory effects of E. alatus, and expected to be potential candidates to prevent/treat inflammation-related diseases.

• Journal of Life Science
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• v.19 no.6
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• pp.698-704
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• 2009

To evaluate a potential possibility of Eucommia ulmoides Oliver as a functional food, ACE (angiotensin converting enzyme) inhibitory activities of leaf, bark, stem and 4 compounds isolated from E. ulmoides were tested. The 4 compounds were isolated and purified by silica gel column chromatography, thin layer chromatography and reverse phase column chromatography. Compound I was pinoresinol-4,4'di-O-${\beta}$-D-glucoside (PG) and compound II was dehydrodiconiferyl alcohol 4,${\gamma}$'-di-O-${\beta}$-D-glucopyranoside (DAG) originating from Eucommial Cortex. The highest amount of PC was present at raw and roasted bark as 135.13 mg% and 163.67 mg%, and the highest amount of DAG was present at raw and roasted leaf as 117.93 mg% and 133.93 mg% respectively. In an ACE inhibition test, 10 mg/ml of roasted leaf, raw and roasted bark extracts of E. ulmoides Oliver were 77.49%, 75.72% and 75.36% respectively, and 10mg/ml of PC and DAG were shown to be 78.51 and 81.20% respectively. $IC_{50}$ values of PG and DAG were 0.6${\pm}$0.2 and 0.5${\pm}$0.2 mg/ml respectively.

• Natural Product Sciences
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• v.12 no.4
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• pp.201-204
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• 2006

Four lignans were isolated from the $CH_2Cl_2-soluble$ fraction of the stem barks of Kalopanax septemlobus and their structures were established as (-)-7R,8S-dehydrodiconiferyl alcohol (1), (-)-simulanol (2), (-)-secoisolariciresinol (3), and $({\pm})-liriodendrin$ (4) based on the spectroscopic methods including MS, $^1H-$ and $^{13}C-NMR$ spectral data.

• Journal of Crop Science and Biotechnology
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• v.11 no.1
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• pp.45-50
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• 2008

Lignans and neolignans are optically active plant secondary metabolites. Research on biosynthesis of lignans has already been advanced especially for the formation of (+) pinoresinol but information on the biosynthesis of 8-O-4'- neolignans is still limited. Moreover, the chemical structure(position of substituents on aromatic rings) and stereochemistry of 8-O-4' neolignans is not clear. Katayama and Kado discovered that incubation of cell-free extracts from E. ulmoides with coniferyl alcohol in the presence of hydrogen peroxide gave (+)-erythro- and (-)-threo- guaiacylglycerol 8-O-4'-(coniferyl alcohol) ether (GGCE)(diastereomeric ratio, 3:2) which is the first report on enzymatic formation of optically active -8-O-4' neolignans from an achiral monolignol. In this aspect, enzymatic formation of guaiacyl 8-O-4' neolignan is noteworthy to clarify its stereochemistry from incubation of coniferyl alcohol with enzyme prepared from Eucommia ulmoides. In this experiment, soluble and insoluble enzymes prepared from E. ulmoides were incubated with 30 mM coniferyl alcohol(CA) for 60 min. The enzyme catalyzed GGCE, dehydrodiconiferyl alcohol(DHCA), and pinoresinol identified by reversed phase HPLC. Consequently, diastereomeric compositions of GGCE were determined as erythro and threo isomer. Enantiomeric composition was determined by the chiral column HPLC. Both enzyme preparations enantioselectively formed (-)-erythro, (+)-erythro and (+)-threo, (-)-threo-GGCEs respectively.