geraniol-1-O-α-L-arabinopyranosyl-(1->6)-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: geraniol-1-O-α-L-arabinopyranosyl-(1->6)-β-D-glucopyranoside
• 英文别名: geranyl 1-O-α-L-arabinopyranosyl-(1->6)-β-D-glucopyranoside；geranyl 1-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside；geranyl 6-O-α-L-arabinopyranosyl-β-D-glucopyranoside；kenposide A；(2R,3R,4S,5S,6R)-2-[(2E)-3,7-dimethylocta-2,6-dienoxy]-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• 化学式: C₂₁H₃₆O₁₀
• 分子量: 448.511
• InChiKey: IEGFOTASSBZIBZ-WRRPXPPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  geraniol-1-O-α-L-arabinopyranosyl-(1->6)-β-D-glucopyranoside 在 silica gel 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (4E)-4-methyl-6-O-[α‑L-arabinopyranosyl-(1→6)-β‑D-glucopyranosyl]-4-hexen-1-one
  参考文献：
  名称：

  硅胶介导的异戊二烯基团氧化产生类似天然产物的产物

  摘要：

  异戊烯基部分常见于萜类化合物和混合生物合成来源的天然产物中。不饱和异戊烯基基序的反应性较少被认识到，这里显示它会影响无环红景天单萜糖苷 kenposide A (8)，当暴露于空气时，它在硅胶上很容易氧化。在这些条件下介导的主要降解产物是一种新的醛，9。通过末端异丙烯基的分解形成缩短的碳骨架，9在质子溶剂中易于缩醛化。对 8 和 8-异戊二烯基配基 (8-PA, 12)（一种具有邻异戊二烯基取代基的黄酮类化合物）的少量降解产物的进一步研究表明，醛的形成可能是通过环氧化和随后异戊二烯基烯键的断裂来实现的。采用 1H NMR 全自旋分析 (HiFSA) 实现了所研究萜类化合物的所有化学位移和耦合常数的分配，并促进了降解产物 9 的结构验证。这项研究表明异戊二烯化化合物通常容易受到氧化降解，特别是在催化介质存在下，而且也在生理条件下。这种氧化伪影/代谢物的形成导致一系列具有异戊二烯基衍生（环状）

  DOI：

  10.1055/a-1472-6164
• 作为产物：
  描述：

  (2E)-3,7-二甲基-2,6-辛二烯-1-基 BETA-D-吡喃葡萄糖苷 在 2,4,6-三甲基吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 85.0h， 生成 geraniol-1-O-α-L-arabinopyranosyl-(1->6)-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Naturally Occurring Geranyl 6-O-Glycosyl-b-D-glucopyranosides

  摘要：

  DOI：

  10.3987/com-05-10640

文献信息

• Terpene Glycosides from the Roots of Sanguisorba officinalis L. and Their Hemostatic Activities
  作者：Wei Sun、Zi-Long Zhang、Xin Liu、Shuang Zhang、Lu He、Zhe Wang、Guang-Shu Wang

  DOI：10.3390/molecules17077629

  日期：——

  Guided by a hemostasis bioassay, seven terpene glycosides were isolated from the roots of Sanguisorba officinalis L. by silica gel column chromatography and preparative HPLC. On the grounds of chemical and spectroscopic methods, their structures were identified as citronellol-1-O-α-l-arabinofuranosyl-(1→6)-β-d-glucopyranoside (1), geraniol-1-O-α-l-arabinofuranosyl-(1→6)-β-d-glucopyranoside (2), geraniol-1-O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranoside (3), 3β-[(α-l-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-d-glucopyranoside (4), 3β-[(α-l-arabinopyranosyl)-oxy]-19α-hydroxyurs-12-en-28-oic acid 28-β-d-glucopyranoside (ziyu-glycoside I, 5), 3β,19α-hydroxyolean-12-en-28-oic acid 28-β-d-glucopyranoside (6) and 3β,19α-di-hydroxyurs-12-en-28-oic acid 28-β-d-glucopyranoside (7). Compound 1 is a new mono-terpene glycoside and compounds 2, 3 and 5 were isolated from the Sanguisorba genus for the first time. Compounds 1–7 were assayed for their hemostatic activities with a Goat Anti-Human α2-plasmin inhibitor ELISA kit, and ziyu-glycoside I (5) showed the strongest hemostatic activity among the seven terpene glycosides. This is the first report that ziyu-glycoside Ι has strong hemostatic activity.

  在止血生物测定的指导下，采用硅胶柱层析和制备型高效液相色谱法从山姜（Sanguisorba officinalis L.）根中分离出七种萜烯苷。根据化学和光谱方法，确定其结构为香茅醇-1-O-α-阿拉伯呋喃糖基-(1→6)-β-d-吡喃葡萄糖苷（1）、香叶醇-1-O-α-阿拉伯呋喃糖基-(1→6)-β-d-吡喃葡萄糖苷（2）、香叶醇-1-O-α-阿拉伯呋喃糖基-(1→6)-β-d-吡喃葡萄糖苷（3）、香叶醇-1-O-α-阿拉伯呋喃糖基-(1→6)-β-d-吡喃葡萄糖苷（4）和香叶醇-1-O-α-阿拉伯呋喃糖基-(1→6)-β-d-吡喃葡萄糖苷（5）、3β-[(α-l-arabinopyranosyl)-oxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-d-glucopyranoside (4)、3β-[(α-larabinopyranosyl)-oxy]-19α-羟基乌苏-12-烯-28-酸 28-β-d-glucopyranoside （ziyu-glycoside I、5）、3β,19α-羟基乌苏-12-烯-28-酸 28-β-d-吡喃葡萄糖苷（6）和 3β,19α-二羟基乌苏-12-烯-28-酸 28-β-d-吡喃葡萄糖苷（7）。化合物 1 是一种新的单萜烯苷，化合物 2、3 和 5 是首次从 Sanguisorba 属植物中分离出来的。用山羊抗人α2-磷脂酶抑制剂酶联免疫吸附试剂盒检测了化合物 1-7 的止血活性，结果表明，在七种萜烯苷中，紫玉苷 I（5）的止血活性最强。这是首次报道紫玉糖苷Ι具有很强的止血活性。
• The Role of Diglycosides as Tea Aroma Precursors:  Synthesis of Tea Diglycosides and Specificity of Glycosidases in Tea Leaves
  作者：Sachiko Matsumura、Shunya Takahashi、Mariko Nishikitani、Kikue Kubota、Akio Kobayashi

  DOI：10.1021/jf960852b

  日期：1997.7.1

  Two general synthetic routes were established in order to synthesize two diglycosides, primeverosides (1) and vicianosides (2), found in tea leaves. Procedure 1 is based on the Koenig-Knorr type of condensation of aglycon alcohols and 1-alpha-bromohexabenzoylprimeverose (6) and is suitable for the condensation of primary alcohols. Procedure 2 is to combine tribenzoyl-beta-D-glucoside (8) and 1-alpha-bromotribenzoylxylose (4). The primeveroside of a tertiary alcohol was synthesized by this method which is also applicable to the synthesis of vicianosides. The hydrolysis rate of each of the 12 synthesized glycosides by a crude tea enzyme was evaluated, which suggest that the main glycosidase is primeverosidase and the enzyme mixture shows substrate specificity to both the carbohydrate and aglycon moieties.
• MICROALGAE-DERIVED COMPOSITIONS FOR IMPROVING THE HEALTH AND APPEARANCE OF SKIN
  申请人：TerraVia Holdings, Inc.

  公开号：EP1986665B1

  公开（公告）日：2018-05-02
• Devices and solutions for prevention of sexually transmitted diseases
  申请人：Dillon F. Harrison

  公开号：US20070166797A1

  公开（公告）日：2007-07-19

  Provided herein are antiviral compounds and methods of culturing microalgae to produce polysaccharides. Included in the invention are methods of producing novel polysaccharides with high antiviral avtivity. Also provided are methods of using polysaccharides for applications such as preventing or treating viral infections and providing prophylaxis and treatment for sexually transmitted diseases.
• Methods and compositions for improving the health and appearance of skin
  申请人：Dillon F. Harrison

  公开号：US20070166266A1

  公开（公告）日：2007-07-19

  Provided herein are skin care compositions and methods of improving the health and appearance of skin. Also provided are methods of using polysaccharides for applications such as topical personal care products, cosmetics, and wrinkle reduction compositions. The invention also provides novel polysaccharide molecules useful for improving the health and appearance of skin.