• Natural Product Sciences
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• v.15 no.1
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• pp.17-21
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• 2009

Column chromatographic separation of the alcoholic extract from the roots of Berberis amurensis yielded eight phenolic constituents including six lignans, hanultarin (1), (-)-secoisolariciresinol (3), (+)-lyoniresinol (5), (+)-syringaresinol (6), (+)-syringaresinol-O-$\beta$-D-glucopyranoside (7), liriodendrin (8), and two phenylpropanoids, 4-glucosyloxy-3-methoxyphenyl trans-propenoic ethyl ester (2), trans-ferulic acid (4). The structures were determined on the basis of NMR spectroscopic data. All isolated compounds(1-8) were reported for the first time from this source. Compound 1 exhibited moderate cytotoxicity against four human cancer cell lines in vitro using sulforhodamin B bioassay.

• Korean Journal of Pharmacognosy
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• v.35 no.3 s.138
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• pp.194-198
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• 2004

Repeated column chromatography of an ethyl acetate extract of the root bark of Albizzia julibrissin Durazz afforded four compounds, euscaphic acid ester glucoside (1), luteolin-7 -O-neohesperidoside (2), (+)-medioresinol (3), (-)-syringaresinol (4). Their structures were determined by chemical and spectroscopic methods. Compounds 1-4 were isolated from this plant for the first time. Among these compounds, (+)-medioresinol (3) exhibited moderate cytotoxic activity against XF 498 and HCT 15 cell line.

• Archives of Pharmacal Research
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• v.26 no.12
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• pp.1009-1013
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• 2003

A new pterocarpan, (-)-maackiain 3-sulfate (1) was isolated from the methanol extract of roots of Sophora subprostarata together with (-)-maackiain(2), trifolirhizin (3), lupeol (4), ononin (5),7,4'-dihydroxyflavone (5), and (+)-syringaresinol (7). The structure of 1 was determined by analyses of 2D NMR and HRFABMS. Compounds 5-7 were isolated from this plant for the first time.

• Natural Product Sciences
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• v.8 no.4
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• pp.147-151
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• 2002

In the course of our work on anti-platelet constituents from plants, eight phenolic compounds, $({\pm})-syringaresinol$ (1), 4-hydroxybenzaldehyde (2), 4-hydroxybenzoic acid (3), vanillic acid (4), 4-hydroxy cinnamic acid (5), quercetin 3-O-rhamnoside (6), rutin (7), and quercetin $3-(2^G-rhamnosylrutinoside)$ (8) were isolated from the methanol extract of the leaves of Magnolia obovata. The compounds were identified based on the spectroscopic data. Compound 2, 3, 5, 6, 7 and 8 were isolated for the first time from genus Magnolia. 1 and 6 showed same order of inhibitory potencies as acetylsalicylic acid (ASA) to rat platelet aggregation induced by all the stimulators tested. The remaining six compounds showed only mild effects.

• The Korean Journal of Food And Nutrition
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• v.32 no.2
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• pp.148-154
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• 2019

The aim of this study was to select compounds for the standardization of fermented Kalopanax pictus Nakai (KP-F), to develop the analysis method using HPLC-PDA and to perform method validation. KP-F is a fermented powder developed to improve the original physiological activities and create a new functionality. Eleutheroside E, Acanthoside B, and Syringaresinol were selected as the standard compounds and developed our own method for simultaneous analysis. The analyte was isolated using C18 column with a gradient elution of 0.05 M phosphoric acid in water and methanol as the mobile phase at a flow rate of 1 mL/min and detected at 210 nm. As a result, all standard compounds showed good linearity with an $R^2$ (coefficient of correlation) of 1.000 and for the limit of detection range of $0.710{\sim}0.831{\mu}g/mL$, and the limit of quantification as $2.150{\sim}2.520{\mu}g/mL$. The precision was RSD (%) of less than 4.80%, while the accuracy was 4.70%>RSD (%) for the range 102.44~110.48%. In conclusion, the developed analysis method is suitable for the detection of Eleutheroside E, Acanthoside B, and Syringaresinol in KP-F.

• Journal of Ginseng Research
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• v.46 no.4
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• pp.536-542
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• 2022

Background: In aged skin, reactive oxygen species (ROS) induces degradation of the extracellular matrix (ECM), leading to visible aging signs. Collagens in the ECM are cleaved by matrix metalloproteinases (MMPs). Syringaresinol (SYR), isolated from Panax ginseng berry, has various physiological activities, including anti-inflammatory action. However, the anti-aging effects of SYR via antioxidant and autophagy regulation have not been elucidated. Methods: The preventive effect of SYR on skin aging was investigated in human HaCaT keratinocytes in the presence of H₂O₂, and the keratinocyte cells were treated with SYR (0-200 ㎍/mL). mRNA and protein levels of MMP-2 and -9 were determined by real-time PCR and Western blotting, respectively. Radical scavenging activity was researched by 2,2 diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) assays. LC3B level was assessed by Western blotting and confocal microscopy. Results: SYR significantly reduced gene expression and protein levels of MMP-9 and -2 in both H₂O₂-treated and untreated HaCaT cells. SYR did not show cytotoxicity to HaCaT cells. SYR exhibited DPPH and ABTS radical scavenging activities with an EC₅₀ value of 10.77 and 10.35 ㎍/mL, respectively. SYR elevated total levels of endogenous and exogenous LC3B in H₂O₂-stimulated HaCaT cells. 3-Methyladenine (3-MA), an autophagy inhibitor, counteracted the inhibitory effect of SYR on MMP-2 expression. Conclusion: SYR showed antioxidant activity and up-regulated autophagy activity in H₂O₂-stimulated HaCaT cells, lowering the expression of MMP-2 and MMP-9 associated with skin aging. Our results suggest that SYR has potential value as a cosmetic additive for prevention of skin aging.

• Journal of Korean Medicine for Obesity Research
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• v.23 no.1
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• pp.10-17
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• 2023

Objectives: The aim of this study was to compare the total phenolic content of Korean Acanthopanax senticosus stems harvested in different seasons and provide basic data for developing functional reinforcement products based on the optimal harvesting time. Methods: Each sample harvested in different seasons was extracted and concentrated twice for 2 hours using 70% ethyl alcohol. Phenolic compounds were analyzed using high-performance liquid chromatography for simultaneous multi-component analysis of 14 compounds, including syringaresinol and so on. Results: The results showed that the stem of Korean Acanthopanax senticosus harvested in winter (November 29th) (EAS-5) had the highest phenolic content of 1.038%. The stem of Korean Acanthopanax senticosus harvested in autumn (October 1st) (EAS-4) showed the second-highest phenolic content of 0.764%, followed by the stem of Korean Acanthopanax senticosus harvested in spring (February 2nd) (EAS-1) with a content of 0.390%. On the other hand, the stem of Korean Acanthopanax senticosus harvested in the summer (June 2nd) (EAS-3) showed the lowest content at 0.342%. In conclusion, the stem of Korean Acanthopanax senticosus harvested in winter (EAS-5) showed the highest phenolic compound content. Conclusions: Considering the extraction yield and the total phenolic content, as well as the concentrations of key functional components such as eleutheroside B, chlorogenic acid, and syringaresinol in the 70% ethyl alcohol extract of Korean Acanthopanax senticosus, it is suggested that the stems of Korean Acanthopanax senticosus harvested during the winter season are suitable for the development of novel materials with enhanced anti-obesity functionality.

• Biomolecules & Therapeutics
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• v.18 no.2
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• pp.211-218
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• 2010

Acanthopanax koreanum Nakai (Araliaceae) is a medicinal plant indigenous to Korea. The root and stem barks of Acanthopanax species have been used as a tonic and sedative as well as in the treatment of rheumatism and diabetes. In our study, three lignans, eleutheroside E (EE), tortoside A (TA), and syringaresinol (SY), were isolated from the stem and root of A. koreanum in an effort to study the immunomodulating effect. We treated natural killer cells and dendritic cells with lignans (EE, TA, or SY), and analyzed their cytokine (IL-12 and IFN-${\gamma}$) secretion. EE, TA, or SY markedly enhanced IL-12 secretion in mouse lymphoid (DC1) and myeloid type (DC2.4) dendritic cells after 48 hr of treatment. There were no significant differences in the cytokine stimulatory effects between EE, TA, or SY. Moreover, treatment of EE, TA, or SY significantly induced IFN-${\gamma}$ secretion by human NK cells (NK92MI) confirmed by ELISA assay. This study suggests that lignans from A. koreanum modulate cytokines, and that such modulation may provide the mechanism of action for many of their therapeutic effects.

• Korean Journal of Pharmacognosy
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• v.28 no.3
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• pp.112-116
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• 1997

Hibiscus syriacus L. (Malvaceae) is widely distributed over Korean, China, India and Siberia. The dried flower of Hibiscus syriacus is used as a folk medicine for curing of hematochezia, dysentery, obstruction due to wind-phlegm, regurgitation, and vomiting of food, and the dried root bark is used antipyretic, anthelmintic and antifungal agents. From a chloroform extract of root bark of this plant, compound I, II, and III were isolated and the structures were elucidated by various spectroscopic analyses. These compounds were identified as syringaresinol. E-N-feruloyltyramine, and Z-N-feruloyltyramine, respectively and were isolated from this plant for the first time. Compound II and III exhibited lipid peroxidation inhibitory activities with $IC_{50}$ of 15.5 and 28.6 ${\mu}g/ml$, respectively.

• Korean Journal of Pharmacognosy
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• v.50 no.2
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• pp.124-132
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• 2019

This study compared the contents of phenolic components depending on the extracting conditions of Acanthopanax koreanum stem to provide basic information for developing Acanthopanax koreanum-based functional foods. Our findings show that the content of total phenolic component peaked at 16 hours of extraction (WAK-16, 7.22%) and when water extracted at $100^{\circ}C$. However, 11-hours water extraction (WAK-11) showed highest eleutheroside B concentration of 1.32%, a main component of A. koreanum, and the level of chlorogenic acid concentration was the highest when 1-hour water extraction (WAK-1) was conducted, being 2.12%. Moreover, highest concentration of eleutheroside E was observed in 16-hours water extraction (WAK-16) as 1.49%. With 60-hours water extraction (WAK-60), the content of syringaresinol, an active phenolic aglycon substance, concentration was the highest with the value of 0.10%. Isofraxidin showed the highest concentration of water extract(0.09%) for 20 hours (WAK-20) and 0.42% for sinapyl alcohol[16 hours (WAK-16)].