• 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).

• 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.

• Natural Product Sciences
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• 제14권1호
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• pp.51-55
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• 2008

Three sesquiterpene-lignans, eudeshonokiol B (1), eudesobovatol B (2), and clovanemagnolol (3), were isolated from the stem bark of Magnolia obovata, together with magnolol (4), honokiol (5), and obovatol (6) on the basis of spectroscopic and physicochemical analyses including 2D NMR and Mass. Compounds 1 - 3 were belongs to a unique class of natural products made up of a sesquiterpene and biphenyl-type neolignan via an ether bond. All the isolated compounds were tested in vitro for their cytotoxic activity against the HeLa, A549, and HCTll6 cancer cell lines. Compounds 1 - 6 showed the cytotoxic activity against tested cancer cell lines, with $IC_{50}$ values ranging from 7.1 to 14.4 ${\mu}g/mL$.

• 한국약용작물학회:학술대회논문집
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• 한국약용작물학회 2011년도 춘계학술발표회
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• pp.342-343
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• 2011

• 약학회지
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• 제46권2호
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• pp.98-101
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• 2002

The phytochemical study of nutmeg, the seeds of Myristica fragrans Houttuyn (Myristicaceae) led to the isolation of three lignans, safrole (I), macelignan (III), and a 3,4 : 3',4'-bis(methylenedioxy)lignan (II). The compound II was identified by a mixture (1:1) of (8S, 8'R)- and (8S, 8'S)-forms of bis(3, 4-methylenedioxy)-8, 8'-neolignan by $^1$H-, $^{13}$ C-NMR and $^1$H-$^1$H COSY spectral data. The compound II was isolated for the first time from Myristica fragrans.

• Journal of the Korean Wood Science and Technology
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• 제34권6호
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• pp.72-80
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• 2006

일본잎갈나무 낙엽(8.5 kg)을 채취하여 95% 에탄올 용액으로 추출하고 농축한 후 분획깔때기로 헥산, 메틸렌클로라이드, 에틸아세테이트 및 수용성으로 순차 추출하여 동결건조하였다. 에틸아세테이트용성과 수용성 분획에 대하여 칼럼크로마토그래피를 실시하였고, 충진물질로는 Sephadex LH-20을, 용리용매로는 메탄올 수용액 및 에탄올-헥산 혼합용액을 사용하였다. 단리된 화합물들은 TLC로 확인한 후 NMR 스펙트럼을 사용하여 구조규명을 하였고 FAB-MS와 EI-MS 스펙트럼으로 분자량을 측정하여 7개의 flavonoid 화합물인 (+)-catechin, (-)-epicatechin, 2"-O-rhamnosylvitexin, juglanin, afzelin, laricitrin-3-O-${\beta}$-D-glucopyranoside 및 isoquercitrin과 neolignan 화합물인 cedrusin을 단리하였다.

• 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.

• Biomolecules & Therapeutics
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• 제28권5호
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• pp.397-404
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• 2020

Adiponectin secretion-promoting compounds have therapeutic potentials in human metabolic diseases. Diallyl biphenyl-type neolignan compounds, magnolol, honokiol, and 4-O-methylhonokiol, from a Magnolia officinalis extract were screened as adiponectin-secretion promoting compounds in the adipogenic differentiation model of human bone marrow mesenchymal stem cells (hBM-MSCs). In a target identification study, magnolol, honokiol, and 4-O-methylhonokiol were elucidated as PPARα and PPARγ dual modulators. Diallyl biphenyl-type neolignans affected the transcription of lipid metabolism-associated genes in a different way compared to those of specific PPAR ligands. The diallyl biphenyl-type neolignan structure provides a novel pharmacophore of PPARα/γ dual modulators, which may have unique therapeutic potentials in diverse metabolic diseases.

• Archives of Pharmacal Research
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• 제23권1호
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• pp.46-49
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• 2000

Two neolignan compound, magnolol $(5,5^{l}-diallyl-2,2^{l}-dihydroxybiphenyl, 1)$ and honokiol $(5,5^{l}-diallyl-2,4^{l}-dihydroxybiphenyl, 2)$ were isolated from the stem bark of Magnolia obovata and evaluated for antifungal activity against various human pathogenic fungi. Compound 1 and 2 showed significant inhibitory activities against Trichophyton mentagrophytes, Microsporium gypseum, Epidermophyton floccosum, Aspergillus niger, Cryptococcus neoformans, and Candida albicans with minimum inhibitory concentrations (MIC) in a range of $25-100{\mu}g/ml$. Therefore, compound 1 and 2 could be used as lead compounds for the development of novel antifungal agents.

• 생약학회지
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• 제18권2호
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• pp.94-98
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• 1987

The structure of the neolignan americanin A was confirmed to be 2, through the application of the Selective INEPT NMR technique. Complete and unambiguous proton and $^{13}C-NMR$ assignments are provided.