(1S,2S,4R)-trans-2-hydroxy-1,8-cineole -β-D-glucopyranoside | 113270-15-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,4R)-trans-2-hydroxy-1,8-cineole -β-D-glucopyranoside
• 英文别名: (1S,2S,4R)-trans-2-hydroxy-1,8-cineole β-D-glucopyranoside；(1S,2S,4R)-1,8-epoxy-p-menthan-2-yl O-β-D-glucopyranoside；(1S,2S,4R)-1,8-epoxy-p-menthan-2-O-β-D-glucopyranoside；(1S,2S,4R)-2-hydroxy-1,8-cineole β-D-glucopyranoside；(1S,2S,4R)-2-hydroxy-1,8-cineole-β-D-glucopyranoside；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(1S,4R,6S)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-yl]oxy]oxane-3,4,5-triol
• CAS: 113270-15-8
• 化学式: C₁₆H₂₈O₇
• 分子量: 332.394
• InChiKey: NWZYTZHMCGWGOF-IWLBLEFSSA-N

物化性质

• 沸点：
  493.4±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4,5-三苄氧基苯甲酸 、 (1S,2S,4R)-trans-2-hydroxy-1,8-cineole -β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 反应 24.0h， 以18%的产率得到
  参考文献：
  名称：

  Bioactive monoterpene glycosides conjugated with gallic acid from the leaves of Eucalyptus globulus

  摘要：

  Two monoterpene glycosides, conjugated with gallic acid [globulusin A (1) and B (2)], together with four known compounds, cypellocarpin A (3), eucaglobulin (4), cuniloside (5) and (1S, 2S, 4R)-trans-2-hydroxy-1,8-cineole beta-D-glucopyranoside (6), were isolated from hot-water extracts of the leaves of Eucalyptus globulus. The structures of compounds 1 and 2 were determined by 1D, 2D NMR and MS spectroscopic analyses. The absolute stereochemistry of 1 was determined by correlating the spectroscopic data with those of synthetic compound 6 with a known configuration. Globulusin A (1) and B (2), cypellocarpin A (3) and eucaglobulin (4), scavenged DPPH free radicals and globulusin A (1) showed a higher antioxidant activity than the other tested compounds, with an IC(50) of 3.8 mu M. Globulusin A (1) and eucaglobulin (4) concentration-dependently suppressed inflammatory cytokine production, tumor-necrosis factor-alpha and interleukin-1 beta in cultured human mycloma THP-1 cells co-stimulated with phorbol myristate acetate. These compounds also inhibited melanogenesis in cultured murine melanoma B16F1 cells, without any significant cytotoxicity. These results suggested that globulusin A (1) and eucaglobulin (4), which were isolated as antioxidants from E globulus, also had anti-inflammatory as well as anti-melanogenesis activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.08.030
• 作为产物：
  描述：

  可得然胶 、 1,8-cineole 以9 mg的产率得到(1S,2S,4R)-1,8-epoxy-p-menthan-2-yl O-β-D-glucopyranosyle-(1->6)-β-D-glucopyranoside
  参考文献：
  名称：

  Eucalyptus perriniana培养细胞对1,8-桉树脑的生物转化

  摘要：

  摘要 四种新的生物转化产物, (1 R , 2 R , 4 S )-1,8-epoxy-p -menthan-2-yl O -β-d -glucopyranoside, (1 S , 3 R , 4 R )-和(1 R , 3 S , 4 S )-1,8-环氧-p -薄荷醇-3-基 O -β-d -吡喃葡萄糖苷，和 (1 S , 2 S , 4 R )-1,8-环氧- p-薄荷醇-2-基O-β-d-吡喃葡萄糖基-(1→6)-β-d-吡喃葡萄糖苷，连同已知的(1 S , 2 S , 4 R )-1,8-环氧- p -在施用 1,8-桉树脑后，从 Eucalyptus perriniana 的细胞悬浮培养物中分离出薄荷-2-基 O-β-d-吡喃葡萄糖苷。

  DOI：

  10.1016/s0031-9422(00)90578-8

文献信息

• Biotransformation of 1,8-cineole by cultured cells of Eucalyptus perriniana
  作者：Yutaka Orihara、Tsutomu Furuya

  DOI：10.1016/s0031-9422(00)90578-8

  日期：1994.2

  Abstract Four new biotransformation products, (1 R , 2 R , 4 S )-1,8-epoxy- p -menthan-2-yl O -β- d -glucopyranoside, (1 S , 3 R , 4 R )- and (1 R , 3 S , 4 S )-1,8-epoxy- p -menthan-3-yl O -β- d -glucopyranosides, and (1 S , 2 S , 4 R )-1,8-epoxy- p -menthan-2-yl O -β- d -glucopyranosyl-(1→6)-β- d -glucopyranoside, together with a known (1 S , 2 S , 4 R )-1,8-epoxy- p -menthan-2-yl O -β- d -glucopyranoside

  摘要 四种新的生物转化产物, (1 R , 2 R , 4 S )-1,8-epoxy-p -menthan-2-yl O -β-d -glucopyranoside, (1 S , 3 R , 4 R )-和(1 R , 3 S , 4 S )-1,8-环氧-p -薄荷醇-3-基 O -β-d -吡喃葡萄糖苷，和 (1 S , 2 S , 4 R )-1,8-环氧- p-薄荷醇-2-基O-β-d-吡喃葡萄糖基-(1→6)-β-d-吡喃葡萄糖苷，连同已知的(1 S , 2 S , 4 R )-1,8-环氧- p -在施用 1,8-桉树脑后，从 Eucalyptus perriniana 的细胞悬浮培养物中分离出薄荷-2-基 O-β-d-吡喃葡萄糖苷。
• Bioactive monoterpene glycosides conjugated with gallic acid from the leaves of Eucalyptus globulus
  作者：Tatsuya Hasegawa、Fumihide Takano、Takanobu Takata、Masato Niiyama、Tomihisa Ohta

  DOI：10.1016/j.phytochem.2007.08.030

  日期：2008.2

  Two monoterpene glycosides, conjugated with gallic acid [globulusin A (1) and B (2)], together with four known compounds, cypellocarpin A (3), eucaglobulin (4), cuniloside (5) and (1S, 2S, 4R)-trans-2-hydroxy-1,8-cineole beta-D-glucopyranoside (6), were isolated from hot-water extracts of the leaves of Eucalyptus globulus. The structures of compounds 1 and 2 were determined by 1D, 2D NMR and MS spectroscopic analyses. The absolute stereochemistry of 1 was determined by correlating the spectroscopic data with those of synthetic compound 6 with a known configuration. Globulusin A (1) and B (2), cypellocarpin A (3) and eucaglobulin (4), scavenged DPPH free radicals and globulusin A (1) showed a higher antioxidant activity than the other tested compounds, with an IC(50) of 3.8 mu M. Globulusin A (1) and eucaglobulin (4) concentration-dependently suppressed inflammatory cytokine production, tumor-necrosis factor-alpha and interleukin-1 beta in cultured human mycloma THP-1 cells co-stimulated with phorbol myristate acetate. These compounds also inhibited melanogenesis in cultured murine melanoma B16F1 cells, without any significant cytotoxicity. These results suggested that globulusin A (1) and eucaglobulin (4), which were isolated as antioxidants from E globulus, also had anti-inflammatory as well as anti-melanogenesis activity. (c) 2007 Elsevier Ltd. All rights reserved.