7-hydroxysweroside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-hydroxysweroside
• 英文别名: secologaninic acid；secologanic acid；(3S,4aS,5R,6S)-5-ethenyl-3-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one
• 化学式: C₁₆H₂₂O₁₀
• 分子量: 374.345
• InChiKey: LCTYGGXMQYUYHL-CLTNYIICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  7-hydroxysweroside 在 吡啶 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 96.33h， 生成 methyl (E)-3-[(3R,4aS,5R,6S)-5-ethenyl-1-oxo-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]-2-hydroxy-3-phenylprop-2-enoate
  参考文献：
  名称：

  Homosecoiridoids from the Flower Buds of Lonicera japonica

  摘要：

  Homosecoiridoids (1-15) were isolated from the flower buds of Lonicera japonica. Compounds 1-4, designated as loniphenyruviridosides A D, possess unprecedented skeletons featuring phenylpyruvic acid derived moieties coupled with an iridoid or a secoiridoid nucleus. Compounds 5-15 (lonijaposides D-N) are additional examples of the unusual pyridinium alkaloid-coupled secoiridoids (lonijaposides A C). The validity of the CD data to determine the configuration of the secoiridoid derivatives is discussed on the basis of detailed CD data analysis and semisynthesis of 2 and 3 with the co-occurring secologanic acid. The configuration of secologanic acid was determined by a single-crystal X-ray crystallographic analysis using anomalous scattering of Cu K alpha radiation. Biosynthetic pathways of the homosecoiridoids were postulated. Compounds 1-4 inhibited,STAT-3 activity of HELF cells, and lonijaposides F (7), H (9), I (10), and K (12) showed activity against the release of glucuronidase in rat polymorphonuclear leukocytes induced by platelet-activating factor.

  DOI：

  10.1021/np2004566

文献信息

• Two new β-hydroxy amino acid-coupled secoiridoids from the flower buds of Lonicera japonica: Isolation, structure elucidation, semisynthesis, and biological activities
  作者：Wei-Xia Song、Yong-Chun Yang、Jian-Gong Shi

  DOI：10.1016/j.cclet.2014.05.037

  日期：2014.9

  were isolated from an aqueous extract of the flower buds of Lonicera japonic a. Their uncommon structures including absolute configurations were determined by spectroscopic data analysis, and confirmed by semisynthesis from the co-occurring secologanin ( 3 ) and secologanic acid ( 4 ). Compounds 1 and 2 exhibited resistant activity against β -glucosidase from almonds and hesperidinase from Aspergillus

  摘要从忍冬（Lonicera japonic a）的花蕾水提物中分离出了两种新的β-羟基氨基酸偶联的类香豆素，分别称为丝氨酸二硒精（1）和苏糖二硒精（2）。通过光谱数据分析确定了它们的不常见结构（包括绝对构型），并通过同时存在的secologanin（3）和secologanic酸（4）的半合成证实了它们的结构。化合物1和2对杏仁的β-葡萄糖苷酶和黑曲霉的橙皮苷酶均具有抗药性，它们还对由血小板活化因子诱导的大鼠多形核白细胞中的葡萄糖醛酸苷酶释放具有抑制作用，抑制率分别为（34.9±3.1）％和分别为（53.6±2.6）％。
• Homosecoiridoids from the Flower Buds of <i>Lonicera japonica</i>
  作者：Yang Yu、Weixia Song、Chenggen Zhu、Sheng Lin、Feng Zhao、Xiuli Wu、Zhenggang Yue、Bo Liu、Sujuan Wang、Shaopeng Yuan、Qi Hou、Jiangong Shi

  DOI：10.1021/np2004566

  日期：2011.10.28

  Homosecoiridoids (1-15) were isolated from the flower buds of Lonicera japonica. Compounds 1-4, designated as loniphenyruviridosides A D, possess unprecedented skeletons featuring phenylpyruvic acid derived moieties coupled with an iridoid or a secoiridoid nucleus. Compounds 5-15 (lonijaposides D-N) are additional examples of the unusual pyridinium alkaloid-coupled secoiridoids (lonijaposides A C). The validity of the CD data to determine the configuration of the secoiridoid derivatives is discussed on the basis of detailed CD data analysis and semisynthesis of 2 and 3 with the co-occurring secologanic acid. The configuration of secologanic acid was determined by a single-crystal X-ray crystallographic analysis using anomalous scattering of Cu K alpha radiation. Biosynthetic pathways of the homosecoiridoids were postulated. Compounds 1-4 inhibited,STAT-3 activity of HELF cells, and lonijaposides F (7), H (9), I (10), and K (12) showed activity against the release of glucuronidase in rat polymorphonuclear leukocytes induced by platelet-activating factor.