4-(4-β-D-glucopyranosyloxybenzyl) (2R)-2-(p-hydroxybenzyl)-maleate | 1301133-10-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4-β-D-glucopyranosyloxybenzyl) (2R)-2-(p-hydroxybenzyl)-maleate
• 英文别名: 4-(4-β-D-glucopyranosyloxybenzyl) 2-(p-hydroxybenzyl)malate；grammatophylloside C；4-(4-β-D-glucopyranosyloxybenzyl) eucomate；vandateroside I；vandateroside I, (-)-；(2R)-2-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-oxo-4-[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methoxy]butanoic acid
• CAS: 1301133-10-7
• 化学式: C₂₄H₂₈O₁₂
• 分子量: 508.479
• InChiKey: LQXFPSIXNFKWHE-UINIGASKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  203
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-(4-β-D-glucopyranosyloxybenzyl) (2R)-2-(p-hydroxybenzyl)-maleate 在 盐酸 、 水 作用下， 反应 3.0h， 生成 葡萄糖
  参考文献：
  名称：

  Glucosyloxybenzyl Eucomate Derivatives from Vanda teres Stimulate HaCaT Cytochrome c Oxidase.

  摘要：

  Eucomic acid [(2R)-2-(p-hydroxybenzyl)malic acid)] (1) and three new glucopyranosyloxybenzyl eucomate derivatives, vandaterosides I (2), II (3), and III (4), were isolated and identified from the stems of Vanda teres. Their cellular antiaging properties were evaluated in a human immortalized keratinocyte cell line (HaCaT) by monitoring their effect on cytochrome c oxidase activity, implicated in mitochondrial respiratory function and cellular energy production. Eucomic acid (1) and vandateroside II (3) increased cytochrome c oxidase activity and/or expression, without enhancing cellular mitochondrial content. These two V. teres biomarkers apparently contributed to stimulate respiratory functions in keratinocytes. Since aging and its pathologies may be ascribed to a decline in mitochondrial functions, these biomarkers have the potential to become new natural ingredients for antiaging preparations to remedy age-related disorders such as skin aging.

  DOI：

  10.1021/np1006636

文献信息

• Glucopyranosyloxybenzyl derivatives of (R)-2-benzylmalic acid and (R)-eucomic acid, and an aromatic glucoside from the pseudobulbs of Grammatophyllum speciosum
  作者：Poolsak Sahakitpichan、Chulabhorn Mahidol、Wannaporn Disadee、Nitirat Chimnoi、Somsak Ruchirawat、Tripetch Kanchanapoom

  DOI：10.1016/j.tet.2012.11.082

  日期：2013.1

  Three new glucosyloxybenzyl derivatives of (R)-2-benzylmalic acid and of (R)-eucomic acid, grammatophyllosides A C, and a new phenolic glucoside, grammatophylloside D, were isolated from the pseudobulbs of Grammatophyllum speciosum along with cronupapine, vandateroside II, gastodin, vanilloloside, orcinol glucoside, and isovitexin. The structure elucidations of these compounds were based on analyses of physical and spectroscopic data, as well as chemical evidence. (C) 2012 Elsevier Ltd. All rights reserved.
• COMPOSITION COSMETIQUE
  申请人：Guerlain

  公开号：EP2556080B1

  公开（公告）日：2015-06-03
• COSMETIC COMPOSITION
  申请人：Simmler Charlotte

  公开号：US20130157968A1

  公开（公告）日：2013-06-20

  The invention relates to novel eucomic acid (2-(4-hydroxybenzyl)malic acid) derivatives or plant extracts comprising such derivatives, and also to cosmetic or dermatological compositions containing these compounds or these extracts, and to cosmetic care methods using said compositions. Exemplary compounds are represented by formula (I) below: in which, with the proviso that R 1 , R 2 and R 3 are not simultaneously a hydrogen atom, R 1 and R 3 each independently represent a hydrogen atom or a saturated or unsaturated, preferably C 1 -C 12 , hydrocarbon-based chain comprising an aromatic group, preferably a phenyl, said aromatic group being preferably substituted with a group comprising a sugar, preferably a monosaccharide or disaccharide, said chain optionally also comprising one or more heteroatoms preferably chosen from O, S and N, and R 2 represents a hydrogen atom or a sugar, preferably a monosaccharide or disaccharide, said sugar being optionally substituted, in particular with a residue comprising a saturated or unsaturated, preferably C 1 -C 12 , hydrocarbon-based chain itself comprising an aromatic group, preferably a phenyl, said hydrocarbon-based chain optionally also comprising one or more heteroatoms preferably chosen from O, S and N.
• US9012414B2
  申请人：——

  公开号：US9012414B2

  公开（公告）日：2015-04-21
• Glucosyloxybenzyl Eucomate Derivatives from <i>Vanda teres</i> Stimulate HaCaT Cytochrome <i>c</i> Oxidase.
  作者：Charlotte Simmler、Cyril Antheaume、Patrice André、Frédéric Bonté、Annelise Lobstein

  DOI：10.1021/np1006636

  日期：2011.5.27

  Eucomic acid [(2R)-2-(p-hydroxybenzyl)malic acid)] (1) and three new glucopyranosyloxybenzyl eucomate derivatives, vandaterosides I (2), II (3), and III (4), were isolated and identified from the stems of Vanda teres. Their cellular antiaging properties were evaluated in a human immortalized keratinocyte cell line (HaCaT) by monitoring their effect on cytochrome c oxidase activity, implicated in mitochondrial respiratory function and cellular energy production. Eucomic acid (1) and vandateroside II (3) increased cytochrome c oxidase activity and/or expression, without enhancing cellular mitochondrial content. These two V. teres biomarkers apparently contributed to stimulate respiratory functions in keratinocytes. Since aging and its pathologies may be ascribed to a decline in mitochondrial functions, these biomarkers have the potential to become new natural ingredients for antiaging preparations to remedy age-related disorders such as skin aging.