• Title/Summary/Keyword: Acertannin

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The Chemical Structure of Acertannin. (Acertannin의 화학구조)

  • 우린근
    • YAKHAK HOEJI
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    • v.6 no.1
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    • pp.11-16
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    • 1962
  • The position of galloyl groups in acertannin, as 3, 6-digalloylpolygalito, has been established by well-defined processes. In the courses of the processes eight new compounds, octamethoxyacertannin, 2, 4-dimethoxy-1, 5-anhydro-D-sorbitol, 6-tosylpolygalito, 2, 3, 4-tri-benzoyl-6-tosylpolygalitol, 3, 6-anhydro-1, 5-anhydro-D-sorbitol, and 2, 4-ditosyl-3, 6-anhydro-1, 5-anhydro-D-sorbitol, have been characterized.

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Modulative Effect of Human Hair Dermal Papilla Cell Apoptosis by Acertannin from the Barks and Xylems of Acer ginnala Maxim (신나무 유래 Acertannin의 인체 모유두 세포 Apoptosis 조절 효능)

  • Joung, Seo Woo;Choi, Sun Eun
    • Korean Journal of Pharmacognosy
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    • v.49 no.1
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    • pp.7-14
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    • 2018
  • We isolated gallotannin, 2,6-digalloyl-1,5-anhydroglucitol, known as acertannin (1), from the barks and xylems of Acer ginnala Maxim. It is a genus of Acer species of shrubs in the family Aceraceae. A. ginnala grows in Korea, Japan and Mongolia. We accomplished the structure elucidation by confirming that the result of $^1H$,$^{13}C-NMR$,MS spectrum data was similar to previous references. We measured DPPH and ABTS radical scavenging activity in vitro to evaluate anti-oxidative activities on acertannin isolated from A. ginnala. Acertannin from A. ginnala exhibited potent DPPH and ABTS radical scavenging activities. We examined the antioxidant and apoptosis modulative effects. This examination shows that A. ginnala has not only 1,1-diphenyl-2-picryhydrazyl(DPPH) radical scavenging activity and ABTS radical scavenging activity, but also human hair dermal papilla cell protection effects. These results indicate that the barks and xylems of A. ginnala might be developed as a potent anti-oxidant, hair growth agent, and ingredient for related new functional cosmetic materials.

Antioxidative Compounds in Extracts of Acer ginnala Max. (신나무 추출물의 항산화 활성물질)

  • Han, Seong-Soo;Lo, Seog-Cho;Choi, Yong-Hwa;Kim, Myong-Jo;Kwak, Sang-Soo
    • Korean Journal of Medicinal Crop Science
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    • v.7 no.1
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    • pp.51-57
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    • 1999
  • To search for antioxidative compounds from plant resources, methanol extracts of 45 plant species were investigated using DPPH method. The highest activity was shown in the methanol extract of Acer ginnala($RC_{50}\;:\;15{\mu}g$), followed by Stewartia koreana($RC_{50}\;:\;28{\mu}g$) and Carpinus laxiflora($RC_{50}\;:\;33{\mu}g$). Two antioxidative compounds were isolated from the methanolic extract of Acer ginnala Max and identified as acertannin(2, 6-di-O-galloyl-1, 5-anhydro-D-glucitol) and gallicin (methyl-3, 4, 5-trihydroxybenzoic acid) on the basis of mass spectroscopy, $^1H-\;and\;^{13}C-NMR$ data. The DPPH free radical scavenging activities of acertannin($RC_{50}\;:\;3.5{\mu}g$) and gallicin($RC_{50}\;:\;2.8{\mu}g$) were more effective than those of BHA($RC_{50}\;:\;14{\mu}g$) and ${\alpha}-tocopherol$ ($RC_{50}\;:\;12{\mu}g$).

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Antioxidative Activities and Quantitative Determination of Gallotannins from Barks of Acer ginnala Maxim (신나무 수피로부터 Gallotannin 화합물의 항산화 활성 및 함량분석)

  • Choi, Sun Eun;Park, Kwan-Hee;Oh, Myoeng-Hwan;Jang, Jun-Hye;Jin, Hye-Young;Kim, Sung-Sik;Lee, Min-Won
    • Korean Journal of Pharmacognosy
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    • v.41 no.3
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    • pp.174-179
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    • 2010
  • Activity guided isolation of 80% acetone extract from the barks of Acer ginnala Maxim. yielded five gallotannins [6-galloyl-1,5-anhydroglucitol (ginnalin B) (1), acertannin (3,6-digalloyl-1,5-anhydroglucitol) (2), methyl gallate (3), acertannin (2,6-digalloyl-1,5-anhydroglucitol) (4) and gallic acid (5)]. All of these isolated compounds from Acer ginnala(1-5) were firstly isolated from Acer ginnala Maxim. And contents of compounds from barks of Acer ginnala (Comp. 1: 0.73$\pm$0.002%, Comp. 2: 0.48$\pm$0.001%, Comp. 3: 0.66$\pm$0.002%, Comp. 4: 1.05$\pm$0.002% and Comp. 5: 0.29$\pm$0.001%) were evaluated by HPLC analysis. And, in order to evaluate anti-oxidative activities on Comp. 1-5 isolated from Acer ginnala, DPPH radical scavenging activity was measured in vitro. All of these isolated compounds from Acer ginnala exhibited potent DPPH radical scavenging activities.

Phenolic compounds from Acer ginnala Maxim (신나무의 Phenol성 화합물에 관한 화학적 연구(I))

  • Park, Woong-Yang
    • Korean Journal of Pharmacognosy
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    • v.27 no.3
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    • pp.212-218
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    • 1996
  • Two phenolcarboxylic acids. five flavonoids and one hydrolysable tannin were isolated from the leaves of Acer ginnala Maxim. On the basis of chemical and spectroscopic evidence, the strutures of these compounds were established as gallic acid, ethylgallate, acertannin, quercetin, quercitrin, isoquercitrin, rutin, $quercetin-3-O-{\alpha}-_L-rhamnopyranosyl-2'-gallate$.

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Structural Study on New Tannin, Polygagallin, from Acerginnala Max. (Acerginnala Max.에서 분리한 신 Tannin Polygagallin의 화학구조)

  • 한구동
    • YAKHAK HOEJI
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    • v.6 no.1
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    • pp.1-4
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    • 1962
  • A new tannin, polygagallin, related to acertannin, is isolated from air-dried leaves of Acer ginnala Max. as prismatic crystals with 1/2 H$_{2}$O per mole, m.p.154-155.deg. and [.alpha.]$_{D}$$^{29}$ +43.79.deg. C. Polygagllin gives hexaacetate, m.p.164.5.deg. C, [.alpha.]$_{D}$$^{28}$ +42.deg. C, on treating with anhydroacetic acid and on treating with diazomethane, gives trimethyl ether, m.p.176.deg. C, [.alpha.]$_{D}$$^{22}$ +53.43, which yields triacetate, m.p.160.5.deg. C, [.alpha.]$_{D}$$^{22}$ + 132.5.deg. C, on acetylation and is not attacked by periodate. On hydrolysis, trimethoxypolygagallin yields one mole of polygalitol and that of trimethoxygallic acid. By the above results polygalallin has been established as 3-galloylpolygalito.ygalito.galallin has been established as 3-galloylpolygalito.

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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.

Anti-adipogenic activity of Smilax sieboldii extracts in 3T3-L1 adipocytes (3T3-L1 지방전구세포에서 청가시덩굴 추출물의 항비만 활성)

  • Seohyun Park;Jung A Lee;Seong Su Hong;Eun-Kyung Ahn
    • Journal of Applied Biological Chemistry
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    • v.66
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    • pp.369-378
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    • 2023
  • Smilax sieboldii is one of the Smilax species. A number of Smilax plants have multiple physiologically-active components and anti-inflammatory/anti-oxidant effects. Antiobesity effects induced by Smilax sieboldii have not been reported. In this study, we investigated the effects and molecular mechanisms of anti-obesity activity of 70% ethanol Smilax sieboldii extract (SSE). The anti-obesity effect of SSE was determined using 3T3-L1 adipocytes. We confirmed that SSE was not cytotoxic to murine 3T3-L1 preadipocytes, we evaluated SSE dose-dependently decreased the accumulation of lipids via an Oil Red O assay and triglyceride assay. These anti-obesity activities of SSE were mediated by the inhibition of adipogenesis-related marker genes (peroxisome proliferator activated receptor-γ, CCAAT-enhancer-binding protein α, and SREBP1c) and lipogenesis-related marker genes (fatty acid synthase and aP2). These results suggest that SSE has the potential to exert anti-obesity and anti-hyperlipidemia effects by regulating adipogenic transcription factors and inhibiting the expression of adipogenic markers.