• 제목/요약/키워드: (+)-pinoresinol

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구상나무의 추출성분에 대한 연구 - 리그난에 관하여 - (Studies on the Extractives of Abies koreana Wilson - Concerned with Lignans -)

  • 김윤근
    • Journal of the Korean Wood Science and Technology
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    • 제25권4호
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    • pp.1-9
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    • 1997
  • The Abies koreana Wilson has been unique species of Korea and has not been clearly investigated about lignans of extractives. This studies have been carried out from the isolation and determination of lignans from alcoholic extractives in its xylem. Six lignans were isolated and their structures were determined by spectroscopic methods. They were two new compounds, (+)-koreslactol and (-)koreanol and four known compounds, lariciresinol p-coumarate, (+)-todolactol C, (-)-${\alpha}$-intermedianol, and (+)-pinoresinol.

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Enzymatic Formation of Guaiacylglycerol 8-O-4'-(Coniferyl Alcohol) Ether from Coniferyl Alcohol with Enzyme Preparations of Eucommia ulmoides

  • Alam, Md. Shameul;Katayama, Takeshi;Suzuki, Toshisada;Sultana, Deeder;Sultana, Saima;Hossain, Md. Daud
    • 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.

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산수유 씨의 최종당화산물 생성저해활성 성분 (Constituents of the seeds of Cornus officinalis with Inhibitory Activity on the Formation of Advanced Glycation End Products (AGEs))

  • 이가영;장대식;이윤미;김영숙;김진숙
    • Applied Biological Chemistry
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    • 제51권4호
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    • pp.316-320
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    • 2008
  • 과육을 제거한 산수유 씨의 MeOH 추출물의 EtOAc 분획물로부터 이용하여 10종의 화합물을 분리하였다. 이들 중에서 (+)- pinoresinol, (-)-balanophonin, vanillin, 4-hydroxybenzaldehyde, coniferaldehyde, betulinic acid는 이 식물에서 처음으로 분리된 물질들이다. 본 연구에서 분리된 10종의 화합물에 대한 in vitro 최종당화산물(AGEs) 생성억제효능 실험결과, (-)-balanophonin (화합물 2)과 gallicin(화합물 3)이 각각 $IC_{50}$ 값 27.81과 18.04${\mu}M$로 비교양성대조군인 aminoguanidine(974.59 ${\mu}M$)보다 훨씬 우수한 효능을 나타내었다.

Phytochemical Constituents of Allium victorialis var. platyphyllum

  • Woo, Kyeong Wan;Lee, Kang Ro
    • Natural Product Sciences
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    • 제19권3호
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    • pp.221-226
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    • 2013
  • Phytochemical investigation of the 80% MeOH extract from the leaves of Allium victorialis var. platyphyllum resulted in the isolation of seventeen compounds; two terpenes, three norsesquiterpenes, one furofuran lignan, and eleven phenolic derivatives. Their chemical structures were characterized by spectroscopic methods to be trans-phytol (1), phytene-1,2-diol (2), icariside B2 (3), (6S,9S)-roseoside (4), sedumoside G (5), pinoresinol-4-O-glucoside (6), 2-methoxy-2-(4'-hydroxyphenyl)ethanol (7), 2-hydroxy-2-(4'-hydroxyphenyl)ethanol (8), Benzyl ${\beta}$-D-glucopyranoside (9), methyl ferulate (10), trans-ferulic acid (11), methyl-p-hydroxycinnamate (12), glucosyl methyl ferulate (13), linocaffein (14), siringin (15), 2-(4-hydroxy-3-methoxyphenyl)-ethyl-O-${\beta}$-Dglucopyranoside (16), and pseudolaroside C (17). All compounds were isolated for the first time from this plant.

Lipid Peroxidation Inhibitory Activity of Some Constituents isolated from the Stem Bark of Eucalyptus globulus

  • Yun, Bong-Sik;Lee, In-Kyoung;Kim, Jong-Pyung;Chung, Sung-Hyun;Shim, Gyu-Seop;Yoo, Ick-Dong
    • Archives of Pharmacal Research
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    • 제23권2호
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    • pp.147-150
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    • 2000
  • Twelve compounds with lipid peroxidation inhibitory activity were isolated from the stem bark of E. globulus. Their structures were assigned as a new aromatic monoterpene (1) and eleven known compounds, pinoresinol (2), vomifoliol (3), 3,4,5-trimethoxyphenol 1-O-$\beta$-D-(6'-O-galloyl)glucopyranoside (4), methyl gallate (5), rhamnazin (6), rhamnetin (7), eriodictyol (8), quercetin (9), taxifolin (10), engelitin (11), and catechin (12) on the basis of UV, mass, and NMR spectroscopic analyses. These compounds except vomifoliol significantly inhibited lipid peroxidation in rat liver microsome.

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Antioxidant Compounds from the Root Bark of Hibiscus syriacus

  • Lee, Sang-Jun;Yun, Young-Sook;Lee, In-Kyoung;Ryoo, In-Ja;Yun, Bong-Sik;Yoo, Ick-Dong
    • 한국자원식물학회:학술대회논문집
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    • 한국자원식물학회 1999년도 The 6th International Symposium on the Development of Anti-Cancer Resource from Plants
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    • pp.110-117
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    • 1999
  • A new lignan named as hibiscuside, (+) pinoresinol 4-O-[-glucopyranosyl (12) -rhamnoside] (1), and a known lignan, syringaresinol (2) were isolated from the root bark of Hibiscus syriacus together with two feruloyltyramines (3,4) and three known isoflavonoids (5,6,7). The structures of these compounds have been established on the basis of their NMR, Mass, UV spectra. Among these phenolic compounds,6-O-acetyl daidzin (5), 6-O- acetyl genistin (6), and 3-hydroxy daidzein (7) with IC50 values of 8.2, 10.6, and 4.1 M, respectively, significantly inhibited lipid peroxidation in rat liver microsomes Hibiscuside (1), E and Z-N-feruloyl tyramines (3,4) exhibited moderate antioxidant activity.

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Chemical Constituents from Buddleja officinalis and Their Inhibitory Effects on Nitric Oxide Production

  • Park, Tae Wook;Lee, Chul;Lee, Jin Woo;Jang, Hari;Jin, Qinghao;Lee, Mi Kyeong;Hwang, Bang Yeon
    • Natural Product Sciences
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    • 제22권2호
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    • pp.129-133
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    • 2016
  • Bioactivity-guided fractionation of a methanolic extract of Buddleja officinalis led to the isolation of two monoterpenes, crocusatin M (1), crocusatin C (2), a flavonoid, acacetin (3), three lignans, lariciresinol (4), pinoresinol (5), and syringaresinol (6), and two triterpenoidal saponins, mimengoside B (7) and songarosaponin A (8). The structures of isolates were identified based on 1D-, 2D-NMR, and MS data analysis. All isolates were tested for their inhibition on LPS-induced NO production in RAW 264.7 cells. As a result, mimengoside B (7) and songarosaponin A (8) showed a mild inhibitory activity of NO production.

두충의 건조법별 지표성분 및 항염증 활성 비교 (Comparison of Index Compound Content and Anti-inflammatory Activity of Eucommiae Cortex by Various Drying Methods)

  • 도호정;이진호;하인혁;정화진;이재웅;김민정;김은지;이인희
    • 한방재활의학과학회지
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    • 제27권1호
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    • pp.19-25
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    • 2017
  • Objectives Eucommiae cortex is one of the frequently used herbs for musculoskeletal disorders, with well-known anti-inflammatory effect. Meanwhile, powdered form of herbal drugs is more advantageous than decoction form, in that storing and taking is more convenient. Thus, the authors aimed to investigate whether the drying method affects the index compound level and anti-inflammatory effect of eucommiae cortex water extract. Methods Eucommiae cortex was extracted in distilled water at $100^{\circ}C$ for 3 hours, filtered, and then evaporated under vacuum. One half of the sample was freeze-dried at $-80^{\circ}C$. Another half of the sample was added with dextrin and then spray-dried at $180^{\circ}C$. To assess the possible change in index compound content, pinoresinol diglucoside was selected as the index marker. The content level of the index compound in various extract sample was quantified through high performance liquid chromatography. In addition, iNOS assay in LPS-induced RAW 264.7 cells was adopted to determine the anti-inflammatory effect of various extract samples. Furthermore, MTT assay was performed to confirm that the result of iNOS assay was not due to cytotoxicity. Results There was no significance difference in index compound content between extract samples obtained through two different drying methods. Anti-inflammatory activity of extract samples were similar at the matching concentration, regardless of the drying methods. Extract samples did not show any significant cytotoxicity. Conclusions Extract samples of eucommiae cortex were obtained through freeze-drying and spray-drying. Neither change in index compound content nor difference in anti-inflammatory activity was observed between drying methods.

관절염 치료에 사용되는 한약재들의 항 염증 활성과 기전에 관한 연구 (Study on the Anti-Inflammatory Activity and Mechanism of Medicinal Plants Used in the Treatment of Arthritis)

  • 김유현;박호
    • 대한임상검사과학회지
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    • 제48권3호
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    • pp.176-182
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    • 2016
  • 대식세포에서 염증반응이 진행되면, interleukin-6 (IL-6), tumor necrosis factor-${\alpha}$ (TNF-${\alpha}$) 등의 cytokine들이 발현되어 inducible nitric oxide synthase (iNOS), prostaglandin E2(PGE2) 등의 염증유발인자가 생성된다. 오가피, 우슬, 두충 각각의 추출물이 어느 정도의 항 염증 효능을 보이며 어떤 pro-inflammatory cytokine의 발현을 억제하는지에 대한 연구를 진행하였다. 오가피, 우슬, 두충은 물 추출하고 동결 건조시켰다. 각각의 추출물의 구성 성분들이 잘 추출되었는지 확인하기 위하여 지표물질인 acanthoside D, 20-hydroxyecdysone, pinoresinol diglucoside를 HPLC로 분석하였다. 항 염증 효능을 확인하기 위하여 lipopolysaccharide (LPS)로 RAW 264.7 세포주를 자극하여 염증 반응을 일으킨 상태에서 각각의 추출물을 농도 별로 처리하고 NO assay를 통해 항 염증 효능을 확인하였으며 real time PCR로 pro-inflammatory cytokine들의 발현량을 측정하였다. 결과적으로 각각의 추출물은 지표성분들이 검출되었으며 오가피와 우슬이 두충보다 NO assay에서 높은 활성을 보였다. Cytokine 발현량 측정에서는 오가피와 우슬은 iNOS와 IL-6의 발현을 억제하였고, 우슬은 TNF-${\alpha}$의 발현을 억제하였다. 우리나라는 전통적으로 약재를 조합하여 처방하여 왔다. 본 연구는 관절염에 전통적으로 사용해 오던 약재들이 어떤 기전에 의하여 항 염증 반응을 보이는지 확인하고 이들을 조합하여 사용하였을 때 어떤 근거에 의하여 시너지 효능을 보이는지 확인하였다.