• Journal of Life Science
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• v.24 no.8
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• pp.873-879
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• 2014

The constituents from the needles of the pine tree, Pinus densiflora, were purified and investigated for antithrombotic activity. The needles were initially extracted three times with 70% ethanol, and the extract was sequentially fractionated with chloroform and n-butanol. The aqueous layer formed after n-butanol fractionation was subjected to purification by medium pressure and high pressure liquid chromatography. The two neolignans, 2, 3-dihydro-7-hydroxyl-3-hydroxymethyl-2-(4'-hydroxyl -3-methoxyphenyl)-5-benzofuranpropanol-3-O-${\alpha}$-rhamnopyranoside (a neolignan glycoside) and 2, 3-dihyro-3-hydroxymethyl-7-methoxy-2-(4'-hydroxyphenyl-3'-methoxy)-5-benxofuran propanol 4'-O-${\alpha}$-rhamnopyranoside (icariside $E_4$) were identified by $^1H$ and $^{13}C$ NMR spectra. The effect of the purified compounds, the neolignan glycoside and icariside $E_4$ on thrombin inhibition were investigated by measuring thrombin clotting time in plasma. As a result, the clotting of the neolignan glycoside was delayed four times compared to that of icariside $E_4$. In addition, an analysis of the inhibition effect by changing the concentration showed that the clotting time was delayed in accordance with an increase in the concentration of the neolignan glycoside. Furthermore, we examined the interaction of thrombin and fibrinogen to clarify the action mechanism. As a result, the delay of clotting time in the response of thrombin and pure fibrinogen may indicate that neolignan glycosides inhibit the thrombin action in a direct manner, leading to the suppression of fibrin generation.

• Archives of Pharmacal Research
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• v.22 no.3
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• pp.306-308
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• 1999

The oxidative dimerization of ferulic acid has been carried out using horse-radish peroxidase as catalyst to give a dihydrobenzofuran neolignan (1), the structure of which was elucidated as (2SR, 3RS)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3n-butoxycarbonyl-5-(2E-carboxyethenyl)-7methoxybenzofuran by spectroscopic analyses. This compound showed more potent cytotoxicity against several tumor cell lines than the starting material.

• Archives of Pharmacal Research
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• v.28 no.1
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• pp.34-38
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• 2005

A new neolignan, named simplidin was isolated from the n-butanol extract of stem of Firmiana simplex, together with six known compounds, scopoletin (1), syrigaresinol (2), aquillochin (3), nitidanin (4), tamarixetin 3-rhamnoside (6), and quercitrin (7). On the basis of spectral and chemical evidence, simplidin (5) was determined to be rel-(7R, 8R)-4, 5, 9, 9'-tetrahydroxy-3,3'­dimethoxy-7-O-5', 8-O-4'-neolignan. All the six compounds were also isolated for the first time from this plant.

• Bulletin of the Korean Chemical Society
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• v.31 no.2
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• pp.495-496
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• 2010

• Archives of Pharmacal Research
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• v.24 no.3
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• pp.198-201
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• 2001

Four lignan xylosides and two neolignan glycosides were isolated from the stem and root barks of Ulmus davidiana var. japonica. Their structures were identified as lyoniside, nudiposide, 5'-methoxyisolarciresinol-9'-O-$\beta$- D-xylopyranoside, isolariciresiol-9'-O-$\beta$-D-xylopyranoside, rel-trans-dihydrodehydroconiferyl alcohol 4'-O-$\alpha$-L-rhamnopyranoside and icariside E3 by comparison of their spectral data with those reported in the literatures, respectively.

• Bulletin of the Korean Chemical Society
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• v.29 no.6
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• pp.1250-1252
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• 2008

• Natural Product Sciences
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• v.17 no.2
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• pp.95-99
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• 2011

A monoterpene-neolignan, piperitylmagnolol (1), was isolated from the stem bark of Magnolia officinalis, together with syringaresinol (2), caffeic acid (3), and sinapaldehyde (4). The isolated compounds were established on the basis of spectroscopic and physicochemical analyses including 1D- and 2D-NMR techniques, as well as on comparing the spectral data with those in the literature and of authentic samples. Compounds 1 - 4 were tested for their cytotoxic activity against the HeLa, K562, A549, and HCT116 cancer cell lines in vitro. Of the isolates, piperitylmagnolol (1) exhibited cytotoxic activity against the tested cancer cell lines with $IC_{50}$ values of 7.7 - 9.5 ${\mu}g/ml$.

• Natural Product Sciences
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• v.14 no.3
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• pp.196-201
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• 2008

Five neolignans (1 - 4, 8), two sesquiterpene-lignans (5 - 6), and two phenylpropanoids (7, 9) were isolated from the stem bark of Magnolia obovata Thunberg (Magnoliaceae) by repeated column chromatography. The structures of isolated compounds were identified as 4-methoxyhonokiol (1), obovatol (2), magnolol (3), honokiol (4), eudeshonokiol B (5), eudesobovatol B (6), coumaric acid (7), magnaldehyde B (8), and ${\rho}-coumaric$ acid (9) on the basis of spectroscopic analysis including 2D-NMR and MS data. Compounds 1 - 9 were evaluated for their anti-complement activities against the classical pathway of the complement system. Of them, compound 8 showed significant anti-complement activity on the classical pathway with $IC_{50}$ value of 102.7 ${\mu}M$, whereas compounds 1 - 7 and 9 were inactive. This result indicated that an aldehyde group in the neolignan is important for the anti-complement activity against the classical pathway.

• Journal of Applied Biological Chemistry
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• v.58 no.4
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• pp.295-301
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• 2015

Five phenylpropanoids (1-5), a benzofuran neolignan (6), two 8-O-4'-neolignans (7-8), and five tetrahydrofuran lignans (9-13) were isolated from a methanol extract of Myristica fragrans seeds. The structures of 1-13 were determined by $^1H$- and $^{13}C$-NMR spectroscopic data analyses and a comparison with the literature data. Compound 3 was isolated for the first time from this plant. All the isolated compounds were evaluated for their inhibitory activity against tyrosinase. Among them, safrole (1) showed significant inhibitions against both the monophenolase ($IC_{50}=32.11{\mu}M$) and diphenolase ($IC_{50}=27.32{\mu}M$) activities of tyrosinase. The kinetic analysis shows that safrole (1) is competitive inhibitors for both monophenolase and diphenolase. The apparent inhibition constant ($K_i$) for safrole (1) binding with free enzyme was determined to be 16.05 and $13.66{\mu}M$ for monophenolase and diphenolase, respectively.

• 한국약용작물학회:학술대회논문집
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• 2012.05a
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• pp.231-232
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• 2012