• Title/Summary/Keyword: lignan compound

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Aporphine Alkaloids and their Reversal Activity of Multidrug Resistance (MDR) from the Stems and Rhizomes of Sinomenium acutum

  • Min, Yong-Deuk;Choi, Sang-Un;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • v.29 no.8
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    • pp.627-632
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    • 2006
  • Chromatographic separation of the MeOH extract from the stems and rhizomes of Sinomemium acutum led to the isolation of nine alkaloids and a lignan. Their structures were determined to be dauriporphine (1), bianfugecine (2), dauriporphinoline (3), menisporphine (4), (-)-syringaresinol (5), N-feruloyltyramine (6), acutumine (7), dauricumine (8), sinomenine (9), and magnoflorine (10) by spectroscopic means. These compounds were examined for their P-gp mediated MDR reversal activity in human cancer cells. Compound 1 showed the most potent P-gp MDR inhibition activity with an $ED_{50}$ value $0.03\;{\mu}g/mL$ and $0.00010\;{\mu}g/mL$ in the MESSA/DX5 and HCT15 cells, respectively.

Anti-oxidative Activities of Phenolic Compounds from barks of Pinus densiflora Siebold et Zuccarini

  • Kwon, Joo-Hee;Kwon, Yong-Min;Choi, Sun-Eun;Park, Kwan-Hee;Lee, Min-Won
    • Natural Product Sciences
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    • v.16 no.1
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    • pp.10-14
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    • 2010
  • Phytochemical examination of the barks of Pinus densiflora Siebold et Zuccarini has led to the isolation of one phenylpropanoid, one lignan, one flavonoid, one flavan 3-ol and two procyanidins : 4-O-$\beta$-D-glucopyranosyl-p-coumaric acid (1), 2,3-dihydro-2-(4-methoxy)-7-hydroxy-3-hydroxymethyl-5-(3-hydroxy propyl)-benzofuran 3-O-$\alpha$-D-glucopyranoside (2), taxifolin 3'-O-$\beta$-D-glucopyranoside (3), (+)-catechin (4), procyanidin B1 (5) and epicatechin-($4{\beta}$-8)-catechin-($4{\alpha}$-8)-catechin (6). Among them, Compound 4, 5 and 6 showed potent anti-oxidative activities and these anti-oxidative activities were significantly different compared with ascorbic acid as positive control.

Inhibitory Lignans against NFAT Transcription Factor from Acanthopanax koreanum

  • Cai, Xing-Fu;Lee, Im-Seon;Dat, Nguyen-Tien;Guanghai-Shen;Kang, Jong-Seong;Kim, Dong-Hyun;Kim, Young-Ho
    • Archives of Pharmacal Research
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    • v.27 no.7
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    • pp.738-741
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    • 2004
  • Three lignans isolated from the roots of A. koreanum (Araliaceae), namely eleutheroside E(1), tortoside A(2), and hemiariensin(4), were evaluated for their ability to inhibit NFAT transcription factor. Of these compounds, compound 4, possessing a diarylbutane skeleton, exhibited potent inhibitory activity against NFAT transcription factor (($IC_{50}$ : 36.3${\pm}2.5{\mu}\textrm{M}$). However, the activities of 1 (($IC_{50}$:>500 11M) and 2 (($IC_{50}$: 136.1 ${\pm}9.4\mu\textrm{M}$), which possess bisaryldioxabicy-clooctane skeletons, were lower. As the lignan derivatives of the same skeletons, hinokinin (5) and (-)-yatein (6) with diarylbutane skeletons and(+)-syringaresinol (3) with a bisaryldioxabicy-clooctane skeleton were also studied for their inhibitory effects on NFAT transcription factor.

Studies on the Constituents of Acanthopanax koreanum

  • Chung, Bo-Sup;Kim, Young-Ho
    • Korean Journal of Pharmacognosy
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    • v.17 no.1
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    • pp.62-66
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    • 1986
  • Acanthopanax koreanum Nakai (Araliaceae) is a indigenous medicinal plant growing throughout Jeju-Do in Korea. The plant extract is used in rheumatism, tonic, paralysis and sedative agent. From the roots of A. koreanum, lignan compounds, a diterpenoid, and a polyacetylene compound were isolated and their structures were elucidated by using IR, PMR, CMR and MS spectral data.

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Studies on the Chemical Constituents of Acanthopanax koreanum(ll)

  • Kim, Young-Ho;Chung, Bo-Sup;Ko, Young-Su;Han, Hee-Ja
    • Archives of Pharmacal Research
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    • v.11 no.2
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    • pp.159-162
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    • 1988
  • From the root bark of Acanithopanax koreanum, two polyacetylene compounds and one lignan compound were isolated and identified as falcarinon, falcarindiol and ariensin. Furthermore the steam bark also afforded methyl n-hexacosanoate, methyl linoleate and coniferin.

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Gomisin J with Protective Effect Against t-BHP-Induced Oxidative Damage in HT22 Cells from Schizandra chinensis

  • An, Ren-Bo;Oh, Seung-Hwan;Jeong, Gil-Saeng;Kim, Youn-Chul
    • Natural Product Sciences
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    • v.12 no.3
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    • pp.134-137
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    • 2006
  • Four lignan compounds including gomisin J (1), schizandrin (2), gomisin A (3), and angeloyl gomisin H (4) have been isolated from the MeOH extract of Schizandra chinensis fruits. The evaluation for protective effect of compounds 1-4 against tert-butyl hydroperoxide (t-BHP)-induced cytotoxicity in hippocampal HT22 cell line was conducted. Compound 1 showed significant protective effect with an $EC_{50}$ value of $43.3{\pm}2.3\;{\mu}M$, whereas compounds 2-4 were inactive. Trolox, one of the well-known antioxidant, used as a positive control, and also showed protective effect with an $EC_{50}$ value of $213.8{\pm}8.4\;{\mu}M$. These results suggest that compound 1 may possess the neuroprotective activity against oxidant-induced cellular injuries.

Further Isolation of Antioxidative $(+)-1-Hydroxypinoresinol-1-O-{\beta}-D-glucoside$ from the Rhizome of Salvia miltiorrhiza that Acts on Peroxynitrite, Total ROS and 1,1-Diphenyl-2-picrylhydrazyl Radical

  • Kang, Hye-Sook;Chung, Hae-Young;Byun, Dae-Seok;Choi, Jae-Sue
    • Archives of Pharmacal Research
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    • v.26 no.1
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    • pp.24-27
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    • 2003
  • A furanofuranoid lignan glycoside, with radical scavenging on peroxynitrite, total reactive oxygen species (ROS) and 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical, was isolated from the rhizome of Salvia miltiorrhiza and characterized as (+)-1-hydroxypinoresinol-1-Ο-$\beta$-D-glucoside based on spectroscopic evidence. The compound exhibited peroxynitrite, total ROS and DPPH radical scavenging activities with $IC_{50}$ values of 3.23$\pm$0.04, 2.26$\pm$0.07 and 32.3$\pm$0.13 $\mu$M, respectively. Penicillamine, Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) and L-ascorbic acid, acting as positive controls, showed radical scavenging activities with $IC_{50}$ values of 6.72$\pm$0.25, 1.43$\pm$0.04 and 11.4$\pm$0.07 $\mu$M, respectively.

Phenolic Constituents from Balanophora laxiflora with their Anti-inflammatory and Cytotoxic Effects

  • Anh, Nguyen Thi Hong;Duong, Nguyen Thuy;Vinh, Pham Duc;Ha, Do Thi
    • Natural Product Sciences
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    • v.27 no.1
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    • pp.49-53
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    • 2021
  • Balanophora laxiflora Hemsl. (Balanophoraceae) is a traditional medicinal plant with a diverse array of biological activities. In our exploration of new bioactive constituents from B. laxiflora, we isolated five compounds, including a new lignan, balanophorone (5), and four known phenolic compounds (1-4). The chemical structures of these compounds were determined by extensive spectroscopic analyses, including 1D and 2D NMR, HR-ESI-MS, and CD. In addition, we evaluated the effects of each of the isolates (1-5) on the messenger RNA expression levels of tumor necrosis factor (TNF)-α and cyclooxygenase (COX)-2 in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages and cytotoxicity against MCF-7 and MDA-MB-231 breast cancer cells. Compound 2 showed significant inhibition of LPS-induced COX-2 and TNF-α expression in RAW 264.7 macrophages, while compound 4 showed moderate cytotoxicity against MCF-7 and MDA-MB-231 breast cancer cells, with IC50 values of 18.3 and 30.7 µM, respectively. No significant effects on the viability of normal mammary epithelial cells were observed.

Effects of dihydrocubebin, a lignan isolated from Indonesian plant Piper cubeba, on the histamine release from rat mast cells

  • Nugroho, Agung Endro;Wahyono, Wahyono;Wahyuono, Subagus;Maeyama, Kazutaka
    • Advances in Traditional Medicine
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    • v.10 no.3
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    • pp.200-207
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    • 2010
  • The fruits of Piper cubeba L. are used traditionally to treat respiratory disorders in Indonesia. In order to determine the compounds responsible for this activity, the fruits were extracted with nhexane followed by ethanol to give n-hexane and ethanol extracts. Based on tracheospasmolytic assay on these two extracts, the n-hexane extract was more active to inhibit trachea contraction than that of ethanol extract. Upon bioassay guided isolation of the n-hexane extract, a tracheospasmolytic active compound was isolated and identified as dihydrocubebin [(3,4),(3',4')-bis-methylenedioxy-9,9'dihydroxylignan] $(\underline{1})$. Compound $\underline{1}$ was tested further for its ability to inhibit histamine released from mast cells, using rat basophilic leukemia (RBL-2H3) cell line and rat peritoneal mast cells RPMCs) as models; and $DNP_{24}$-BSA, thapsigargin, ionomycin, compound 48/80 and PMA were used as inducers for histamine released from mast cell. The test result showed that $\underline{1}$ inhibited histamine release from RBL-2H3 cells induced by $DNP_{24}$-BSA, thapsigargin and ionomycin. In addition, $\underline{1}$ suppressed histamine release from RPMC induced by either thapsigargin or ionomycin. However, $\underline{1}$ did not inhibit histamine release from RPMC induced by either compound 48/80 or combination PMA-sub optimum dose of ionomycin. Therefore, it was concluded that the inhibitory effects of $\underline{1}$ on the histamine released from mast cells may involve mechanisms related to intracellular $Ca^{2+}$ signaling events or downstream processes of intracellular $Ca^{2+}$ signaling in mast cells.

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.