• 생명과학회지
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• 제24권8호
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• pp.873-879
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• 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
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• 제28권1호
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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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• 제29권6호
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• pp.1250-1252
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• 2008

• Journal of Applied Biological Chemistry
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• 제58권4호
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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.

• Natural Product Sciences
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• 제18권2호
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• pp.97-101
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• 2012

Six lignan compounds, 1-(17,21-dihydroxyphenyl)-9-(12,13-dihydroxyphenyl)-1-nonanone (malabaricone C) (1), 7'-(3',4'-methylenedioxyphenyl)-8,8'-dimethyl-7-(3,4-dihydroxyphenyl)-butane (2), 7'-(3',4'-dimethoxyphenyl)-8,8'-dimethyl-7-(3-methoxy-4-hydroxyphenyl)-butane (3), 7-(4-hydroxy-3-methoxyphenyl)-7'-(3',4'-methylenedioxyphenyl)-8,8'-lignan-7-methyl ether (4), (+)-erythro-(7S,8R)-${\Delta}^{8^'}$-7-hydroxy-3,4,3',5'-tetramethoxy-8-O-4'-neolignan (5), and (+)-erythro-(7S,8R)-${\Delta}^{8^'}$-7-acetoxy-3,4,3',5'-tetramethoxy-8-O-4'-neolignan (6), were isolated from the seeds of Myristica fragrans. The chemical structures of these compounds were determined on the basis of spectroscopic analyses including 2D NMR. Compounds 1 - 6 were evaluated for their cytotoxic activity against the HL-60, MCF-7, and A549 cancer cell lines in in vitro.

• 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.

• 약학회지
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• 제42권3호
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• pp.238-242
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• 1998

For the investigation of bioactive natural products with analgesic activity, we have evaluated various extracts of Saururi Herba (Saururaceae), which has been used in traditiona l medicine for edema, beriberi, jaundice, turbid urine, carbuncle and furuncle. The diethylether extract of this plant was found to show a significant analgesic effect on writhing syndrome in mice. Using bioactivity-guided separation of the diethylether extract, analgesic constituent, (8S, 8`R, 7R, 6`R)-2'-oxo-4,5: 4',5'-bis(methylenedioxy)-${\Delta}^{1,3,5,3'}$-8.8', 7.6', 2.O.5'-neolignan(sauchinone) was isolated and structurally identified by physico-chemical properties and spectroscopic evidences. This compound has good analgesic activity with lower toxicity, as compared to other antipyretic-analgesic drug(acetaminophen).

• Journal of Applied Biological Chemistry
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• 제56권3호
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• pp.179-181
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• 2013

Repeated $SiO_2$ and octadecyl silica gel (ODS) column chromatographies of the EtOAc fraction from Magnolia obovata fruits, 10 neolignans, named magnolol (1), honokiol (2), isoobovatol (3), isomagnolol (4), obovatol (5), obovatal (6), 9-methoxyobovatol (7), magnobovatol (8), obovaaldehyde (9), and 2-hydroxyobovaaldehyde (10) were isolated and identified. All isolated compounds were evaluated for in vitro cytotoxicity against seven human cancer cell lines.