• Archives of Pharmacal Research
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• 제29권7호
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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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• 제27권3호
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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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• 제22권1호
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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.

• 생명과학회지
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• 제19권6호
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• pp.698-704
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• 2009

두충 (Eucommia ulmoides Oliver)으로부터 항고혈압 활성을 가진 유효물질을 분리하였으며, 두충의 잎, 껍질 및 줄기를 건조한 것과, 건조한 후 붉은 것에 대하여 ACE (angiotensin converting enzyme) 저해활성을 실험하였다. 두충으로부터 분리 한 유효물질은 pinoresinol-4,4'-di-O-${\beta}$-D-glucoside (PG)와 dehydrodiconiferyl alcohol 4,${\gamma}$'-di-O-${\beta}$-D-glucoside (DAG)였으며, 이들은 각각 껍질과 잎에 많이 함유되 어 있었다. 즉 pinoresinol-4,4'-di-O-${\beta}$-D-glucoside (PG)는 자연 건조한 껍질에 135.12 mg%, 붉은 껍질에 163.94 mg%로 가장 많이 함유되어 있었으며, dehydrodiconiferyl alcohol 4,${\gamma}$'-di-O-${\beta}$-D-glucoside (DAG)는 자연 건조한 잎에 117.43 mg%, 붉은 잎에 133.93 mg%로 비교적 많이 함유되어 있었다. ACE 억제활성은 볶은 잎, 말린 껍질 및 볶은 껍질을 10 mg/ml씩 처리하였을 때, 각각 77.49, 75.52 및 75.36%의 억제효과를 나타내었으며, 두충으로부터 분리한 화합물인 pinoresinol-4,4'-di-O-${\beta}$ -D-glucoside (PG)와 dehydrodiconiferyl alcohol 4,${\gamma}$'-di-O-${\beta}$-D-glucoside (DAC)를 1${\sim}$10 mg/ml 처리하였을 때에 는 67.1${\sim}$85.25% 의 억제활성을 나타내었으며, $IC_{50}$값은 각각 0.6${\pm}$0.2, 0.5${\pm}$0.2 mg/ml 였다. 이것은 PG와 DAG가 두충에서 분리한 천연물임을 감안하면 매우 높은 활성을 가지고 있다고 할 수 있다.

• Natural Product Sciences
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• 제12권4호
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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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• 제11권1호
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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.