• 생명과학회지
• /
• 제24권8호
• /
• pp.873-879
• /
• 2014

소나무(Pinus densiflora)의 잎의 성분을 분리하여 항트롬빈 활성을 조사하였다. 잎은 70% ethanol로 3회 추출하였으며, 그 추출물은 순차적으로 chloroform과 n-buthanol로 분획하였다. n-buthanol 분획으로부터 얻은 수용성 분획을 MPLC와 HPLC에 의해 분리하였다. 분리한 compound를 $^1H-$과 $^{13}C-NMR$로 동정한 결과 2, 3-dihydro-7-hydroxyl-3-hydroxymethyl-2-(4'-hydroxyl-3-methoxyphenyl)-5-benzofuranpropanol-3-O-${\alpha}$-rhamnopyranoside(a neolignan glycoside)와 2, 3-dihyro-3-hydroxymethyl-7-methoxy-2-(4'-hydroxyphenyl-3'-methoxy)-5-benxofuran propanol 4'-O-${\alpha}$-rhamnopyranoside (icariside $E_4$)의 neolignan 구조임을 확인하였다. 트롬빈 저해활성은 분리된 neolignan glycoside와 icariside $E_4$을 작용하여 혈장안에서 응고시간으로 측정하였다. 그 결과, neolignan glycoside의 응고시간이 icariside $E_4$보다 4배 이상 지연하였다. 저해활성은 neolignan glycoside의 농도가 증가함에 따라 그 시간이 지연되는 것을 확인하였다. 더 나아가 지연기전을 확인하기 위해 thrombin과 순수한 fibrinogen를 반응하였다. 그 결과, 트롬빈과 순수한 피브리노겐의 작용에 의해 응고시간은 지연되었으며, 이는 neolignan glycoside가 피브린형성에 주요한 트롬빈의 활성을 직접 저해하는 것으로 사료된다.

• Archives of Pharmacal Research
• /
• 제22권3호
• /
• pp.306-308
• /
• 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
• /
• 제28권1호
• /
• pp.34-38
• /
• 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
• /
• 제31권2호
• /
• pp.495-496
• /
• 2010

• Archives of Pharmacal Research
• /
• 제24권3호
• /
• pp.198-201
• /
• 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
• /
• 제29권6호
• /
• pp.1250-1252
• /
• 2008

• Natural Product Sciences
• /
• 제17권2호
• /
• pp.95-99
• /
• 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
• /
• 제14권3호
• /
• pp.196-201
• /
• 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
• /
• 제58권4호
• /
• pp.295-301
• /
• 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
• /
• 한국약용작물학회 2012년도 심포지엄 및 춘계학술발표회
• /
• pp.231-232
• /
• 2012