• Title, Summary, Keyword: methyl resveratrol

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Comparative Depigmentation Effects of Resveratrol and Its Two Methyl Analogues in α-Melanocyte Stimulating Hormone-Triggered B16/F10 Murine Melanoma Cells

  • Yoon, Hoon-Seok;Hyun, Chang-Gu;Lee, Nam-Ho;Park, Sung-Soo;Shin, Dong-Bum
    • Preventive Nutrition and Food Science
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    • v.21 no.2
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    • pp.155-159
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    • 2016
  • Previous research showed that resveratrol (trans-3,4',5-trihydroxystilbene) and pinostilbene (trans-3-methoxy-4',5-dihydroxystilbene) were able to inhibit tyrosinase directly; however, anti-melanogenic effects of pterostilbene (trans-3,5-dimethoxy-4'-hydroxystilbene) and resveratrol trimethyl ether (RTE) have not been compared. To investigate the hypopigmentation effects of pterostilbene and RTE, melanin contents and intracellular tyrosinase activity were determined by western blot analysis. Firstly, pterostilbene showed the inhibitory effects on ${\alpha}$-melanocyte stimulating hormone (MSH)-induced melanin synthesis stronger than RTE, resveratrol, and arbutin. Pterostilbene inhibited melanin biosynthesis in a dose-dependent manner in ${\alpha}$-MSH-stimulated B16/F10 murine melanoma cells. Specifically, melanin content and intracellular tyrosinase activity were inhibited by 63% and 58%, respectively, in response to treatment with $10{\mu}m$ of pterostilbene. The results of western blot analysis indicated that pterostilbene induced downregulation of tyrosinase protein expression and suppression of ${\alpha}$-MSH-stimulated melan-A protein expression stronger than RTE or resveratrol. Based on these results, our study suggests that pterostilbene can induce hypopigmentation effects more effectively than resveratrol and RTE, and it functions via downregulation of protein expression associated with hyperpigmentation in ${\alpha}$-MSH-triggered B16/F10 murine melanoma cells.

Anti-Proliferative Effects of β-Cyclodextrin Inclusion Complexes with Coumarinolignans from Acer mono (고로쇠 Coumarinolignan의 β-Cyclodextrin 포접화합물 제조 및 암세포증식 억제활성)

  • Yim, Soon-Ho;Jung, Da-Woon;Williams, Darren R.;Geckeler, Kurt E.;Kim, Kyung Keun;Shin, Boo Ahn;Lee, Ik-Soo;Kim, Huyn Jung
    • Korean Journal of Pharmacognosy
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    • v.46 no.2
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    • pp.133-139
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    • 2015
  • Two coumarinolignans, cleomiscosins C (1) and D (2) were isolated from the heartwood of Acer mono, together with four compounds, 5-O-methyl-(E)-resveratrol-3-O-${\beta}$-D-glucopyranoside (3), 5-O-methyl-(E)-resveratrol-3-O-${\beta}$-D-apiofuranosyl-(1$\rightarrow$6)-${\beta}$-D-glucopyranoside (4), scopoletin (5), and (E)-resveratrol-3-O-${\beta}$-D-glucopyranoside (6). Of them, cleomiscosins C (1) and D (2) were applied to preparing inclusion complex molecules with ${\beta}$-cyclodextrin (${\beta}$-CD) to improve the very poor solubility in cell media. The CD complexes of 1 and 2 exhibited an enhancement of water solubility which is feasible to measure their cytotoxicity using a spectrophotometer in a cell-based assay. Anti-proliferative activity of these complex molecules was successfully estimated on HCT116 human colon cancer cells, and cleomiscosin D (2) showed anti-proliferative effects at the concentration of 1.95~31.2 ${{\mu}g}$/mL in a dose-dependent manner.

Cytotoxic and Antimutagenic Stilbenes from Seeds of Paeonia lactiflora

  • Kim, Hyo-Jin;Chang, Eun-Ju;Bae, Song-Ja;Shim, Sun-Mi;Park, Heui-Dong;Rhee, Chang-Ho;Park, Jun-Hong;Choi, Sang-Won
    • Archives of Pharmacal Research
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    • v.25 no.3
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    • pp.293-299
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    • 2002
  • Cytotoxic and antimutagenic effects of a novel cis-$\varepsilon$-viniferin and five known stilbenes, transresveratrol, trans-$\varepsilon$-viniferin, gnetin H, suffruticosols A and B, isolated from the seeds of Paeonia lactiflora Pall. (Paeoniaceae) were determined against five different cancer cell lines, and mutagenicity of N-methyl-N'-nitro-N-nitrosoguanidine (MNNG) in Salmonella typhimurium TA100, respectively. Six stilbenes showed cytotoxic activity in a dose-dependent manner, and especially did potent cytotoxic activity against C6 (mouse glioma) cancer cell with $IC_{50}$ values ranging from 8.2 to $20.5{\;}{\mu\textrm{g}}/ml$. trans-Resveratrol showed significant cytotoxic activity against HepG2 (liver hepatoma) and HT-29 (colon) human cancer cell lines with $IC_{50}$ values of 11.8 and 25.2 g/ml, respectively. In contrast, trans-$\varepsilon$-viniferin and cis--viniferin, and gnetin H exhibited marked cytotoxic activity against Hela (cervicse) and MCF-7 (breast) human cancer cell lines with $IC_{50}$ values of 20.4, 21.5, and $12.9{\;}{\mu\textrm{g}}/ml$, respectively. However, suffruticosol A and B had less cytotoxic effect against all cancer cells except C6. Meanwhile, six stilbenes exerted antimutagenic activity in a dose-dependent fashion. Of them, trans-resveratrol exhibited the strongest antimutagenic effect against MNNG with $IC_{50}$ value of $27.0{\;}{\mu\textrm{g}}/plate$, while other five resveratrol oligomers also did moderate antimutagenic activity with $IC_{50}$ values ranging from 31.7 to $35.2{\;}{\mu\textrm{g}}/plate$.

Neuraminidase Inhibitors from Reynoutria elliptica

  • Lee, Chu-Hyun;Kim, Sang-In;Lee, Kyung-Bok;Yoo, Yung-Choon;Ryu, Si-Young;Song, Kyung-Sik
    • Archives of Pharmacal Research
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    • v.26 no.5
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    • pp.367-374
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    • 2003
  • In the course of screening neuraminidase inhibitors from herbal medicines, Reynoutria elliptica exhibited high inhibitory activity. Four active compounds were isolated from the ethyl acetate soluble fraction by consecutive purification using sillica gel, Sephadex LH-20 chromatography, and recrystallization. The chemical structures of these compounds were identified as 1,3,8-trihydroxy-6-methylanthraquinone (emodin) 1,8-dihydroxy-3-methoxy-6-methylanthraquinone (emodin 3-methyl ether; physcion), 1,3,8-trihydroxy-6-hydoxymethylanthraquinone ($\omega$-hydroxyemodin), and 3,5,4 -trihydroxystilbene (trans-resvertrol) by spectral data including MS, $^1 H-, and ^{13}C-NMR. The IC_{50}$ values of emodin, emodin 3-methyl ether, $\omega$-hydroxyemodin, and trans-resvertrol were 2.81, 74.07, 10.49, and 8.77 $\mu$M, respectively. They did not inhibit other glycosidase such as glucosidase, mannosidase, and galactosidase, indicating that they were relatively specific inhibitors of neuraminidase.

Nematicidal Activity of Eclipta prostrata Extract and Terthiophene against Pine Wood Nematode, Bursaphelenchus xylophilus (한련초(Eclipta prostrata) 추출물과 terthiophene의 소나무재선충(Bursaphelenchus xylophilus)에 대한 살선충 효과)

  • Shin, Jin Hee;Kwon, OhGyeong;Lee, Chae Min;Lee, Sang Myeong;Choi, Young Hwa;Kim, Jin Ho;Kim, Young Sub;Lee, Dong Woon
    • The Korean Journal of Pesticide Science
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    • v.20 no.1
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    • pp.56-65
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    • 2016
  • Pine wood nematode, Bursaphlenchus xylophilus is a fatal damaging pest, infecting pinewood trees and is one of the serious forest pest in Korea. Trunk injection is one of the most effective method to protect the live pine trees from nematode infection. The aim of this research was to reveal the efficacy of the nematicidal materials from 46 Kyrgyzstan, 88 Vietnam plant materials and 21 active materials (${\alpha}$-terpinene, ${\alpha}$-pinene, ${\beta}$-thujaplicin, cinnamaldehyde, eugenol, emodin, geraniol, limonone, methyl palmitate, matrine, myrcene, methyl gallate, nicotine, quassin, resveratrol, rotenone, thymol, thujaplicin, terthiophene, tuberstemonine, ${\gamma}$-terpinene) isolated from plants for using as trunk injection agents. Eclipta prostrata extract was highly effective against pine wood nematode in plant extracts and terthiophene has the best nematicidal activity from active materials isolated from plants. Foliar spray of terthiophene on Japanese black pine (Pinus thunbergii) tree reduced proliferation of inoculated pine wood nematode at 22 days after treatment, however no efficacy was found over 22 days. Eclipta prostrata extract and terthiophene can be used as nematicide for further nematicidal efficacy test against any other plant parasitic nematodes and trunk injection efficacy against pine wood nematode.

Chemical Constituents from the Leaf and Twig of Acer okamotoanum Nakai and their Cytotoxicity

  • Jin, Wen-Yi;Min, Byung-Sun;Youn, Ui-Jung;Hung, Tran-Manh;Song, Kyung-Sik;Seong, Yeon-Hee;Bae, Ki-Hwan
    • Korean Journal of Medicinal Crop Science
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    • v.14 no.2
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    • pp.77-81
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    • 2006
  • As a result of cytotoxic compounds against cancer cell lines from natural sources, senven compounds were isolated from the leaf and twig of Acer okamotoanum Nakai. The compounds (1-7) were identified as ethyl gallate (1), methyl gallate (2), gallic acid (3), trans $resveratrol-3-O-{\beta}-D-glucopyranoside$ (4), acertannin (5), nikoenoside (6), and fraxin (7) by physicochemical and spectroscopic data (including mp, UV, IR, MS, $^1H-NMR,\;^{13}C-NMR$, DEPT, and HMBC) in comparison with those of published papers. All the compounds were tested for their cytotoxic activity against L1210, HL-60, K562, and B16F10 cancer cell lines in vitro by MTT assay method. Compounds 1-3 and 5 showed cytotoxic activity against all tested cell lines with $IC_{50}$ values ranged from 12.5 to $72.2\;{\mu}M$. Of the compounds, methyl gallate (2) exhibited the most potent cytotoxic activity against L1210, HL-60, K562, and B16F10 tumor cells with $IC_{50}$ values of 12.5, 48.3, 22.8, and $22.8\;{\mu}M$, respectively. Other compounds did not show any cytotoxic activity against four cancer cell lines.

Antioxidant, Antimicrobial and Cytoprotective Effects of the Extract and Its Fraction Obtained from Rhizomes of Belamcanda chinensis (L.) DC (범부채 뿌리 추출물 및 분획물의 항산화, 항균 및 세포 보호 효과)

  • Song, Ba Reum;Lee, Sang Lae;Lee, Yun Ju;Shin, Hyuk Soo;Park, Soo Nam
    • Applied Chemistry for Engineering
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    • v.29 no.6
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    • pp.772-781
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    • 2018
  • In this study, we investigated antioxidant, antimicrobial and cytoprotective effects of 50% ethanol extract and ethyl acetate fraction from rhizomes of Belamcanda chinensis (L.) DC. 1,1-Diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activities ($FSC_{50}$) of the 50% ethanol extract and ethyl acetate fraction were 621.5 and $253.0{\mu}g/mL$, respectively. Total antioxidant capacities ($OSC_{50}$) of the extract and fraction were 13.6 and $3.0{\mu}g/mL$, respectively. Minimum inhibitory concentrations (MIC) of the ethyl acetate fraction for Staphylococcus aureus and Candida albicans were 156, $1,250{\mu}g/mL$, respectively, indicating similar or higher levels of those of using methyl paraben. Cytoprotective effects of the 50% ethanol extract against $^1O_2$-induced cellular damage (${\tau}_{50}$) showed in a dose dependent manner at 4 to $64{\mu}g/mL$. ${\tau}_{50}$ of the 50% ethanol extract, ethyl acetate fraction and (+)-${\alpha}$-tocopherol at $16{\mu}g/mL$ were 36.4, 45.0 and 45.8 min respectively, and the ethyl acetate fraction showed cytoprotective effects similar to (+)-${\alpha}$-tocopherol. In ultraviolet B radiation-induced HaCaT cell damage, the ethyl acetate fraction decreased intracellular reactive oxygen species (ROS) up to 45.9% at $8{\mu}g/mL$. Also in $H_2O_2$-induced HaCaT cell damage, the ethyl acetate fraction significantly increased the cell viability at $0.5{\sim}8.0{\mu}g/mL$. As a result of chemical analyses of the ethyl acetate fraction, the presence of flavonoids and polyphenol such as irisflorentin, irigenin, tectorigenin, resveratrol, iridin and tectoridin were identified. In conclusion, the extract/fraction from rhizomes of B. chinensis can be applied as a natural antioxidant and antimicrobial material to cosmetics.