• Title/Summary/Keyword: pinoresinol

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

  • Kim, Yun-Geun
    • Journal of the Korean Wood Science and Technology
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    • v.25 no.4
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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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    • v.11 no.1
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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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Constituents of the seeds of Cornus officinalis with Inhibitory Activity on the Formation of Advanced Glycation End Products (AGEs) (산수유 씨의 최종당화산물 생성저해활성 성분)

  • Lee, Ga-Young;Jang, Dae-Sik;Lee, Yun-Mi;Kim, Young-Sook;Kim, Jin-Sook
    • Applied Biological Chemistry
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    • v.51 no.4
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    • pp.316-320
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    • 2008
  • Ten compounds, (+)-pinoresinol (1), (-)-balanophonin (2), gallicin (3), vanillin (4), 4-hydroxybenzaldehyde (5), coniferaldehyde (6), betulinic acid (7), ursolic acid (8), 5-hydroxymethyl furfural (9), and malic acid (10), were isolated from a EtOAc-soluble fraction of the seeds of Cornus officinalis. The structures of these compounds were elucidated by spectroscopic methods as well as by comparison with reported values. Compounds 1, 2, and 4-7 were isolated from this species for the first time. All the isolates (1-10) were subjected to an in vitro bioassay to evaluate their inhibitory activity against advanced glycation end products (AGEs) formation. Among these, compounds 2 and 3 showed the significant inhibitory activity on AGEs formation with $IC_{50}$ values of 27.81 and 18.04${\mu}M$, respectively.

Phytochemical Constituents of Allium victorialis var. platyphyllum

  • Woo, Kyeong Wan;Lee, Kang Ro
    • Natural Product Sciences
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    • v.19 no.3
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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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    • v.23 no.2
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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
    • Proceedings of the Plant Resources Society of Korea Conference
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    • 1999.10a
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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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    • v.22 no.2
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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.

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

  • Do, Ho-Jeong;Lee, Jin-Ho;Ha, In-Hyuk;Chung, Hwa-Jin;Lee, Jae-Woong;Kim, Min-Jeong;Kim, Eun-Jee;Lee, In-Hee
    • Journal of Korean Medicine Rehabilitation
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    • v.27 no.1
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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.

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

  • Kim, Yoo-Hyun;Park, Ho
    • Korean Journal of Clinical Laboratory Science
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    • v.48 no.3
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    • pp.176-182
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    • 2016
  • When inflammatory reaction is in progress, the macrophages release inflammatory cytokines, such as interleukin-6 (IL-6), tumor necrosis factor-${\alpha}$ (TNF-${\alpha}$), and product inflammatory mediators, including inducible nitric oxide synthase (iNOS) and prostaglandin E2 (PGE2). We conducted this study to evaluate the anti-inflammatory efficacy on each water extract of Acanthopanacis cortex, Achyranthes radix, and Eucommiae cortex, and to investigate whether they inhibit the expression of pro-inflammatory cytokine. Acanthopanacis cortex, Achyranthes radix, and Eucommiae cortex were extracted with water and freeze-dried. Acanthoside D, 20-hydroxyecdysone, and pinoresinol diglucoside as an index material were analyzed by high-performance liquid chromatography (HPLC) to ensure that the components of each extracts were extracted well. RAW 264.7 cell line, stimulated with lipopolysaccharide (LPS) to cause an inflammatory response, was treated with each water extract at various concentrations to determine the anti-inflammatory efficacy. Then, the anti-inflammatory efficacy was confirmed by a nitric oxide (NO) assay, and the mRNA expression levels of pro-inflammatory cytokines were measured by real time PCR. As a result, the indicator materials were detected from each extract, and Acanthopanacis cortex water extract (ACWE) and Achyranthes radix water extract (ARWE) were shown to have a high activity than Eucommiae cortex water extract (ECWE) in NO assay. In Korea, traditionally it prescribed a combination of medicinal herbs. This study confirmed the anti-inflammatory response of these medicinal plants in arthritis and its synergistic effect when used in combination with western medicine.