3S,8S-dihydroxydec-9-en-4,6-yne-1-O-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3S,8S-dihydroxydec-9-en-4,6-yne-1-O-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5S,6R)-2-[(3S,8S)-3,8-dihydroxydec-9-en-4,6-diynoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₆H₂₂O₈
• 分子量: 342.346
• InChiKey: MWOLLPDIFAGNPI-VLUPQUSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3S,8S-dihydroxydec-9-en-4,6-yne-1-O-β-D-glucopyranoside 在 盐酸 作用下， 以 水 为溶剂， 反应 5.0h， 生成 葡萄糖
  参考文献：
  名称：

  Polyacetylenes and anti-hepatitis B virus active constituents from Artemisia capillaris

  摘要：

  Three new polyacetylenes, 8-(2)-decene-4, 6-diyne-1, 3, 10-triol (1), 1, 3S, 8S-trihydroxydec-9-en-4, 6-yne (2), 3S, 8S-dihydroxydec-9-en-4, 6-yne 1-O-beta -D-glucopyranoside (3), and one new glucosyl caffeoate, 1-O-ethyl-6-O-caffeoyl-beta -D-glucopyranose (4), together with 34 known compounds were isolated from Artemisia capillaris. The structures of the new compounds were determined by extensive spectroscopic analyses including 1D and 2D NMR, HRESIMS, [alpha](D) and CD experiments. Among them, 19 compounds showed activity inhibiting HBsAg secretion; 20 compounds showed activity inhibiting HBeAg secretion; and 25 compounds possessed inhibitory activity against HBV DNA replication according to our anti-HBV assay on HepG 2.2.15 cell line in vitro. The most active compound 12 could inhibit not only the secretions of HBsAg and HBeAg, but also HBV DNA replication with IC50 values of 15.02 mu M (SI = 111.3), 9.00 mu M (SI = 185.9) and 12.01 mu M (SI = 139.2). (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2014.03.017

文献信息

• Polyacetylenes and anti-hepatitis B virus active constituents from Artemisia capillaris
  作者：Yong Zhao、Chang-An Geng、Chang-Li Sun、Yun-Bao Ma、Xiao-Yan Huang、Tuan-Wu Cao、Kang He、Hao Wang、Xue-Mei Zhang、Ji-Jun Chen

  DOI：10.1016/j.fitote.2014.03.017

  日期：2014.6

  Three new polyacetylenes, 8-(2)-decene-4, 6-diyne-1, 3, 10-triol (1), 1, 3S, 8S-trihydroxydec-9-en-4, 6-yne (2), 3S, 8S-dihydroxydec-9-en-4, 6-yne 1-O-beta -D-glucopyranoside (3), and one new glucosyl caffeoate, 1-O-ethyl-6-O-caffeoyl-beta -D-glucopyranose (4), together with 34 known compounds were isolated from Artemisia capillaris. The structures of the new compounds were determined by extensive spectroscopic analyses including 1D and 2D NMR, HRESIMS, [alpha](D) and CD experiments. Among them, 19 compounds showed activity inhibiting HBsAg secretion; 20 compounds showed activity inhibiting HBeAg secretion; and 25 compounds possessed inhibitory activity against HBV DNA replication according to our anti-HBV assay on HepG 2.2.15 cell line in vitro. The most active compound 12 could inhibit not only the secretions of HBsAg and HBeAg, but also HBV DNA replication with IC50 values of 15.02 mu M (SI = 111.3), 9.00 mu M (SI = 185.9) and 12.01 mu M (SI = 139.2). (C) 2014 Elsevier B.V. All rights reserved.