• Title/Summary/Keyword: honokiol

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Diallyl Biphenyl-Type Neolignans Have a Pharmacophore of PPARα/γ Dual Modulators

  • Han, Yujia;Liu, Jingjing;Ahn, Sungjin;An, Seungchan;Ko, Hyejin;Shin, Jeayoung C.;Jin, Sun Hee;Ki, Min Won;Lee, So Hun;Lee, Kang Hyuk;Shin, Song Seok;Choi, Won Jun;Noh, Minsoo
    • Biomolecules & Therapeutics
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    • v.28 no.5
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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.

Comparison of the Cytoprotective Effects of Several Natural and Synthetic Compounds against Oxidative Stress in Human Retinal Pigment Epithelial Cells (인간 망막 색소상피 세포에서 산화적 스트레스에 대한 천연 및 합성 화합물들의 세포 보호 효과 비교)

  • Kim, Da Hye;Kim, Jeong-Hwan;Park, Seh-Kwang;Jeong, Ji-Won;Kim, Mi-Young;Nam, Soo-Wan;Lee, Hyesook;Choi, Yung Hyun
    • Journal of Life Science
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    • v.31 no.2
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    • pp.126-136
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    • 2021
  • Oxidative stress causes injury to and degeneration of retinal pigment epithelial (RPE) cells. It is involved in several retinal disorders and leads to vision loss. In the present study, we investigated the effect of 14 kinds of natural compounds and two kinds of synthetic compounds on oxidative stress-induced cellular damage in human PRE cell lines (ARPE-19). From among them, we selected five kinds of compounds, including auranofin, FK-509, hemistepsin A, honokiol, and spermidine, which have inhibitory effects against hydrogen peroxide (H2O2)-mediated cytotoxicity. In addition, we found that four kinds of compounds (excluding auranofin) have protective effects on H2O2-induced mitochondrial dysfunction. Furthermore, the expression of phosphorylation of histone H2AX, a sensitive marker of DNA damage, was markedly up-regulated by H2O2, whereas it was notably down-regulated by FK-506, honokiol, and spermidine treatment. Meanwhile, five kinds of candidate compounds had no effect on H2O2-induced intracellular reactive oxygen species (ROS) levels, suggesting that the five candidate compounds have protective effects on oxidative stress-induced cellular damage through the ROS-independent pathway. Taken together, according to the results of H2O2-mediated cellular damage―such as cytotoxicity, apoptosis, mitochondrial dysfunction, and DNA damage―spermidine and FK-506 are the natural and synthetic compounds with the most protective effects against oxidative stress in RPE. Although further studies on the identification of the mechanism responsible are required, the results of the present study suggest the possibility of using spermidine and FK-506 to suppress the risk of retinal disorders.

Antimicrobial Activities of Hydroxybiphenyl Derivatives (II) - Synthesis and Antibacterial Activities of Allylhydroxybiphenyl Compounds against a Cariogenic Bacterium Streptococcus mutans ATTCC OMZ176

  • Seo, Won-Jun;Koo, Sung-Hyen;Bae, Ki-Hwan
    • Archives of Pharmacal Research
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    • v.9 no.3
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    • pp.127-130
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    • 1986
  • Naturally occurring diallyldihydroxybiphenyl compounds, magnolol and honokiol were reported to have potent antibacterial activities against most of Gram positive bacteria (1-4). To developmore potent antibacterial agents, some allyhydroxybiphenyl derivatives were synthesized from the starting compounds, p-phenyl-phenol (I) p-phenylphenol (IV), o, o-biphenol (VII) and p. p'-biphenol (XII). Among the newly synthesized compounds (III, VI, IX, XI, XIV and XVI), the antibacterial activities of 2-allyl-p-phenylphenol (VI), 6-ally-o, 0'-biphenol (IX), 2, 2'-diallyl-o, o'-biphenol (XIV) and 2, 2', 6-triallyl-p, p'-biphenol (XIV) were more potent than those of magnolol and bonokiol against a cariogenic bacterium, Stroptococcus matans ATCC OMZ 176.

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Anti-complement Activity of Phenolic Compounds from the Stem Bark of Magnolia obovata

  • Min, Byung-Sun
    • Natural Product Sciences
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    • v.14 no.3
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    • pp.196-201
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    • 2008
  • Five neolignans (1 - 4, 8), two sesquiterpene-lignans (5 - 6), and two phenylpropanoids (7, 9) were isolated from the stem bark of Magnolia obovata Thunberg (Magnoliaceae) by repeated column chromatography. The structures of isolated compounds were identified as 4-methoxyhonokiol (1), obovatol (2), magnolol (3), honokiol (4), eudeshonokiol B (5), eudesobovatol B (6), coumaric acid (7), magnaldehyde B (8), and ${\rho}-coumaric$ acid (9) on the basis of spectroscopic analysis including 2D-NMR and MS data. Compounds 1 - 9 were evaluated for their anti-complement activities against the classical pathway of the complement system. Of them, compound 8 showed significant anti-complement activity on the classical pathway with $IC_{50}$ value of 102.7 ${\mu}M$, whereas compounds 1 - 7 and 9 were inactive. This result indicated that an aldehyde group in the neolignan is important for the anti-complement activity against the classical pathway.

An Experimental Study on the Component Variation of Naesowhajung-tang by the Three Types of Extraction Method and the Effects of Each Type on the Gastrointestinal Tract (추출방법(抽出方法)에 따른 내소화중탕(內消和中湯)의 효능(效能)에 대(對)한 연구(硏究))

  • Kim, Jin-Seong;Ryu, Bong-Ha;Park, Dong-Won;Ryu, Ki-Won;Yoon, Joo-Ho
    • The Journal of Internal Korean Medicine
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    • v.22 no.1
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    • pp.29-38
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    • 2001
  • When I evaluated the component variation of Naesowhajung-tang by the three types of extraction method, and each type's effects on the gastrointestinal tract, I got the following results. 1. The output ratio of extracts made out of Naesowhajung-tang were not significantly different among 13.8% of water extract(Sample-I), 13.5% of 50% ethanol extract(Sample-II), and 15.6% of water extract by spray dryer(Sample-III). 2. magnolol, honokiol, hesperidin, naringin, poncirin and glycyrrhizin Sample II had the largest amount of the following contents: magnolol, honokiol, hesperidin, naringin, poncirin and glycyrrhizin. 3. All the extracts of Naesowhajung-tang showed the inhibitory effect on the smooth muscle contraction of the isolated ileum in mice and fundus-strip in rats induced by acetylcholine chloride and barium chloride. 4. High concentration Sample-II was recognized to be effective in preventing gastric ulcers in Shay's rats. but not in the other rat group. 5. All the extracts of Naesowhajung-tang were recognized to be effective in preventing gastric ulcers induced by Ethanol-HCl in rats. 6. The increase of transport ability in the small intestine was recognized only when the concentration of all the samples was doubled, but not in the other concentrations. 7. The increase of transport ability in the large intestine was recognized only when the concentration of Sample-II was doubled, but not in other concentration. Using the results mentioned above, I suggest that Sample-II has more significant effects on the gastrointestinal tract than the others.

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Quantitative Analysis of Hyangsayukgunja-Tang Using an Ultra-Performance Liquid Chromatography Coupled to Electrospray Ionization Tandem Mass Spectrometry (LC-MS/MS를 이용한 향사육군자탕의 주요성분의 함량분석)

  • Seo, Chang-Seob;Shin, Hyeun-Kyoo
    • Korean Journal of Pharmacognosy
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    • v.46 no.4
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    • pp.352-364
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    • 2015
  • The aim of this study was to quantitatively analyze for quality assessment of eighteen marker compounds, including homogentisic acid, 3,4-dihydroxybenzaldehyde, spinosin, liquiritin, hesperidin, ginsenoside Rg1, liquiritigenin, ginsenoside Rb1, glycyrrhizin, 6-gingerol, atractylenolide III, honokiol, costunolide, dehydrocostuslactone, atractylenolide II, nootkatone, magnolol, and atractylenolide I, in Hyangsayukgunja-tang using an ultra-performance liquid chromatography-electrospray ionization-mass spectrometer. The column for separation of eighteen marker components were used a UPLC BEH $C_{18}$ analytical column ($2.1{\times}100mm$, $1.7{\mu}$) and kept at $45^{\circ}C$ by gradient elution with 0.1% (v/v) formic acid in water and acetonitrile as mobile phase. The flow rate and injection volume were 0.3 mL/min and $2.0{\mu}l$, respectively. The correlation coefficient of all marker compounds was ${\geq}0.9914$, which means good linearity, within the test ranges. The limits of detection and quantification values of the all analytes were in the ranges 0.04-1.11 and 0.13-3.33 ng/mL, respectively. As a result, five compounds, homogentisic acid, 3,4-dihydroxybenzaldehyde, spinosin, liquiritigenin, and atractylenolide I, in this sample were not detected and the amounts of the 13 compounds except for the 5 compounds were $8.10-6736.37{\mu}g/g$ in Hyangsayukgunja-tang extract.

Sesquiterpene-Neolignans from the Stem Bark of Magnolia obovata and Their Cytotoxic Activity

  • Youn, Ui-Joung;Chen, Quan Cheng;Lee, Ik-Soo;Kim, Hong-Jin;Hung, Tran Manh;Na, Min-Kyun;Lee, Jong-Pill;Min, Byung-Sun;Bae, Ki-Hwan
    • Natural Product Sciences
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    • v.14 no.1
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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 ${\mu}g/mL$.

Chemistry Study on Protective Effect against·OH-induced DNA Damage and Antioxidant Mechanism of Cortex Magnoliae Officinalis

  • Li, Xican;Fang, Qian;Lin, Jing;Yuan, Zhengpeng;Han, Lu;Gao, Yaoxiang
    • Bulletin of the Korean Chemical Society
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    • v.35 no.1
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    • pp.117-122
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    • 2014
  • As a Chinese herbal medicine used in East Asia for thousands years, Cortex Magnoliae Officinalis (CMO) was observed to possess a protective effect against OH-induced DNA damage in the study. To explore the mechanism, the antioxidant effects and chemical contents of five CMO extracts were determined by various methods. On the basis of mechanistic analysis, and correlation analysis between antioxidant effects & chemical contents, it can be concluded that CMO exhibits a protective effect against OH-induced DNA damage, and the effect can be attributed to the existence of phenolic compounds, especially magnolol and honokiol. They exert the protective effect via antioxidant mechanism which may be mediated via hydrogen atom transfer (HAT) and/or sequential electron proton transfer (SEPT). In the process, the phenolic-OH moiety in phenylpropanoids is oxidized to the stable quinine-like form and the stability of quinine-like can be ultimately responsible for the antioxidant.