• Title/Summary/Keyword: magnolol

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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.

Synthesis of 4,4'-Biphenol Derivatives and Antibacterial Activities against a Cariogenic Bacterium, Streptococcus mutans OMZ 176 (4,4'-Biphenol 유도체의 합성 및 충치균 Streptococcus mutans OMZ 176에 대한 항균작용)

  • Bae, Ki-Hwan;Seo, Won-Jun;Leem, Seung-Hee
    • YAKHAK HOEJI
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    • v.36 no.1
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    • pp.36-39
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    • 1992
  • In a continuous study for the developing of the anticariogenic agents, 3,3'-diacyl-4,4'-biphenol derivatives (Fig. 2, 2 and 3) and 3,3'-bis-(1-hydroxyalkyl)-4,4'-biphenol (Fig. 3, 4 and 5) derivatives are synthesized successively from 4,4'-diphenol (Fig. 2, 1). The synthesized compounds are tested for their antibacterial activity against a cariogenic bacterium, Streptococcus mutans OMZ 176. The acyl derivatives, 2 and 3, do not show antibacterial activity, but the hydroxyalkyl derivatives, 4 and 5, reduced from the acyl group of 2 and 3, show the activity. The antibacterial activity of 2 and 3 may be inhibited due to intramolecular hydrogen bonding between the acyl group and the hydroxyl one (Fig. 4).

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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.

Analysis Screening of Bioconversion Products from Fermentation Samchulgeonbi-tang with Microorganisms via RP-HPLC-DAD (RP-HPLC-DAD를 이용한 발효 삼출건비탕의 생물전환 성분 분석)

  • Lee, Kwang Jin;Yang, Hye Jin;Liang, Chun;Ma, Jin Yeul
    • Korean Journal of Pharmacognosy
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    • v.44 no.2
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    • pp.125-130
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    • 2013
  • Samchulgeonbi-tang (SC) is well-known traditional herbal medicine which is composed of fourteen medicine herbs. SC has been used for the treatment of the chronic gastritis, indigestion, gastric ulcers, gastroptosis and diarrhea disease. The variation in the amount of bioactive components of SC and its fermentation SC with ten Lactobacillus strains were investigated via high-performance liquid chromatography coupled with diode array detection (HPLC-DAD). Simultaneous qualitative and quantitative analysis of seven bioactive compounds; paeoniflorin, liquiritin, hesperidin, liquiritigenin, kaempferol, atractylenolide III, magnolol were achieved by comparing their retention times ($t_R$) and UV spectra with those of the standard compounds. In the results, the amount of paeoniflorin and hesperidin were 7.967 mg/g, 7.251 mg/g that were the main compounds in SC. The amounts of liquiritigenin was increased by all ten Lactobacillus strains, except strain 128. Especially, the liquiritigenin amount was highest in SC fermented with strain 145 (0.201 mg/g), which was increased by 158.39% compared to SC (0.081 mg/g). In the fermented SC using strains 344, almost components were increased than non-fermented SC, except paeoniflorin and kaempferol. Thus, these results considered that the strains 145 and 344 are most excellent fermentation strains among the 10 species of fermentation strains.

Synergistic Antimicrobial Effect of Lonicera japonica and Magnolia obovata Extracts and Potential as a Plant-Derived Natural Preservative

  • Lee, Ye Seul;Lee, Yun Ju;Park, Soo Nam
    • Journal of Microbiology and Biotechnology
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    • v.28 no.11
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    • pp.1814-1822
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    • 2018
  • Most people use cosmetics to protect their skin. Preservatives are often used to prevent their contamination upon use. There has been a great demand for natural preservatives due to recent reports on the side effects of parabens. Therefore, we evaluated the antimicrobial activities of Lonicera japonica and Magnolia obovata extracts and determined their potential as natural preservatives. We found that the 50% ethanol extract from L. japonica had antibacterial activity only against S. aureus and P. aeruginosa, while the ethyl acetate fraction showed antimicrobial activity against all six microbial strains tested. On the other hand, the 70% ethanol extract and the ethyl acetate fraction from M. obovata showed antimicrobial activity against all six strains. A synergistic effect against S. aureus, B. subtilis, and C. albicans was confirmed when two ethyl acetate fractions having antimicrobial activity against all six strains were used in combination. Synergistic activity against B. subtilis was also confirmed through kill-time analysis. High-performance liquid chromatography was performed to identify the components of each extract. Based on the minimum inhibitory concentration and the results of a disc diffusion assay, we confirmed that caffeic acid and luteolin influenced the antimicrobial activity of L. japonica and that the antimicrobial activity of M. obovata was influenced by the interaction of magnolol and honokiol with other components. Therefore, this study suggests that the combination of L. japonica and M. obovata extracts may be used as a plant-derived natural preservative.

Quantitative Determination of the Marker Components in Pyungwi-San Using LC-ESI-MS/MS (LC-ESI-MS/MS를 이용한 평위산 주요 성분의 함량 분석)

  • Seo, Chang-Seob;Shin, Hyeun-Kyoo
    • Korean Journal of Pharmacognosy
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    • v.49 no.3
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    • pp.270-277
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    • 2018
  • Pyungwi-san has been used to treat the digestive system diseases, physconia, nausea, anorexia, and dyspepsia in Korea. In this study, an ultra-performance liquid chromatography-electrospray ionization-mass spectrometry (UPLC-ESI-MS/MS) method was optimized for simultaneous determination of the 14 marker components, spinosin, liquiritirn apioside, liquiritin, narirutin, 6'''-feruloylspinosin, hesperidin, liquiritigenin, glycyrrhizin, 6-gingerol, atractylenolide III, honokiol, atractylenolide II, magnolol, and atractylenolide I in Pyungwi-san extract. All analytes were separated on a Waters Acquity UPLC BEH $C_{18}$ analytical column ($2.1{\times}100mm$, $1.7{\mu}m$) with maintained at $45^{\circ}C$. The mobile phase consisted of 0.1% (v/v) aqueous formic acid and acetonitrile. The MS conditions were as follows: capillary voltage 3.3 kV, extractor voltage 3.0 V, RF lens voltage 0.3 V, source temperature $120^{\circ}C$, desolvation temperature $300^{\circ}C$, desolvation gas 600 L/h, cone gas 50 L/h and collision gas 0.14 mL/min. The coefficient of determination of 14 analytes was 0.9989-1.0000. The limits of detection and quantification values of the all analytes were 0.04-2.56 and 0.13-7.69 ng/mL, respectively. As a result of the analysis using the established LC-ESI-MS/MS method, the 5 components, spinosin, 6'''-feruloylspinosin, atractylenolide III, II, and I derived from Zizyphi Fructus and Atractylodis Rhizoma, were not detected in this extract. On the other hand, the 9 components except for the 5 components were 4.15-498.87 mg/kg in lyophilized Pyungwi-san extract. Among these components, glycyrrhizin, marker compound of Glycyrrhizae Radix et Rhizoma, was detected the most amount as a 498.87 mg/kg.