(2R,3R,4S,5S)-2,3,4,5-tetrakis(trimethylsilyloxy)hexanal | 19127-15-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5S)-2,3,4,5-tetrakis(trimethylsilyloxy)hexanal
• CAS: 19127-15-2
• 化学式: C₁₈H₄₄O₅Si₄
• 分子量: 452.886
• InChiKey: HZBOSAPUGYAKKA-XSLAGTTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-鼠李糖 、 三甲基硅咪唑 在 吡啶 作用下， 反应 0.08h， 生成 (2R,3R,4S,5S)-2,3,4,5-tetrakis(trimethylsilyloxy)hexanal
  参考文献：
  名称：

  Novel quercetin glucosides from Helminthostachys zeylanica root and acceleratory activity of melanin biosynthesis

  摘要：

  两种新型槲皮素葡萄糖苷、4′-O-β-d-glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside （化合物 1）和 4′-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside （化合物 2）、从 Helminthostachys zeylanica 根 50 ；%EtOH提取物中分离得到。分离化合物的结构分析主要通过 600 MHz 和 800 MHz NMR、UPLC-TOFMS 和 GC-MS 来实现。在两种槲皮素葡萄糖苷中，化合物 1 在 10 μM 浓度下对小鼠 B16 黑色素瘤细胞具有较高的黑色素生成加速作用，是对照组的 2.7 倍，且无细胞毒性作用。

  DOI：

  10.1007/s11418-012-0672-9

文献信息

• Anti-inflammatory Triterpenoid Saponins from the Stem Bark of <i>Kalopanax pictus</i>
  作者：Tran H. Quang、Nguyen T. T. Ngan、Chau V. Minh、Phan V. Kiem、Nguyen X. Nhiem、Bui H. Tai、Nguyen P. Thao、Nguyen H. Tung、Seok B. Song、Young H. Kim

  DOI：10.1021/np200382s

  日期：2011.9.23

  Five new compounds, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3 beta,6 beta,23-trihydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopyranoside (3), 3-O-[2,3-di-O-acetyl-alpha-L-arabinopyranosyl]hederagenin 28-O-alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranoside (4), and 3-O-[3,4-di-O-acetyl-alpha-L-arabinopyranosyl]hederagenin 28-O-alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranoside (5), as well as 10 known compounds (6-15), were isolated from the stem bark of Kalopanax pictus. Compounds 1-5 and 7-14 inhibited TNF alpha-induced NF-kappa B transcriptional activity in HepG2 cells in a dose-dependent manner, with IC(50) values ranging from 0.6 to 16.4 mu M. Furthermore, the transcriptional inhibitory function of these compounds was confirmed on the basis of decreases in COX-2 and iNOS gene expression in HepG2 cells. The structure activity relationship of the compounds with respect to anti-inflammatory activity is also discussed.
• Novel quercetin glucosides from Helminthostachys zeylanica root and acceleratory activity of melanin biosynthesis
  作者：Kosei Yamauchi、Tohru Mitsunaga、Irmanida Batubara

  DOI：10.1007/s11418-012-0672-9

  日期：2013.4

  Two novel quercetin glucosides, namely 4′-O-β-d-glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside (compound 1) and 4′-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside (compound 2), were isolated from Helminthostachys zeylanica root 50 % EtOH extract. Structural analysis of isolated compounds was achieved mainly by 600 MHz and 800 MHz NMR, UPLC–TOFMS and GC–MS. Of the two quercetin glucosides, compound 1 showed a high melanogenic acceleratory effect, 2.7 times higher than control, at 10 μM concentration in murine B16 melanoma cells, with no cytotoxic effect.

  两种新型槲皮素葡萄糖苷、4′-O-β-d-glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside （化合物 1）和 4′-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside （化合物 2）、从 Helminthostachys zeylanica 根 50 ；%EtOH提取物中分离得到。分离化合物的结构分析主要通过 600 MHz 和 800 MHz NMR、UPLC-TOFMS 和 GC-MS 来实现。在两种槲皮素葡萄糖苷中，化合物 1 在 10 μM 浓度下对小鼠 B16 黑色素瘤细胞具有较高的黑色素生成加速作用，是对照组的 2.7 倍，且无细胞毒性作用。