洋芹糖 | 639-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 洋芹糖
• 中文别名: 芹糖
• 英文名称: L-apiose
• 英文别名: L-apiose；(S)-2,3,4-trihydroxy-3-hydroxymethyl-butyraldehyde；(S)-2,3,4-Trihydroxy-3-hydroxymethyl-butyraldehyd；3-Hydroxymethyl-L-tetrose；L-3-hydroxymethyl-tetrose；(2S)-2,3,4-trihydroxy-3-(hydroxymethyl)butanal
• CAS: 639-97-4；6477-44-7；42927-70-8
• 化学式: C₅H₁₀O₅
• 分子量: 150.131
• InChiKey: AVGPOAXYRRIZMM-SCSAIBSYSA-N

物化性质

• 沸点：
  368.8±35.0 °C(Predicted)
• 密度：
  1.518±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（少许）、甲醇（少许）、水

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  洋芹糖 、 2,5-二氯苯肼 生成 3-hydroxymethyl-[2]tetrosulose-bis-(2,5-dichloro-phenylhydrazone)
  参考文献：
  名称：

  Weygand; Schmiechen, Chemische Berichte, 1959, vol. 92, p. 535,538

  摘要：

  DOI：
• 作为产物：
  描述：

  (3S)-O²,O³-isopropylidene-β-L-apiofuranose 在 Dowex 50W (H⁺ form) 作用下， 以 水 为溶剂， 反应 5.0h， 生成 洋芹糖
  参考文献：
  名称：

  Triterpenoid saponins from Becium grandiflorum var. obovatum

  摘要：

  Two new triterpenoid saponins, beciumecine I and 2, were-isolated from the root bark of Becium grandiflorum var, obovatum and their structures established as 3-O-(beta-D-glucopyranosyl) terminolic acid 28-O-beta-D-apiofuranosyl( 1-3)-[alpha-L-rhamnopyranosyl( 1-3)-beta-D-xylopyranosyl( 1-4)]-alpha-L-rhamnopyranosyl(1-2)-alpha-L-arabinopyranoside and 3-O-(beta-D-glucopyranosyl) 24-hydroxyterminolic acid 28-O-alpha-L-rhamnopyranosyl(1-3)-beta-D-xylopyranosyl(1-4)-alpha-L-rhamnopyranosyl(1-2)-alpha-L-arabinopyranoside, respectively. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00413-0

文献信息

• A New Monoterpenoid Glycoside from Myrica esculenta and the Inhibition of Angiotensin I-Converting Enzyme
  作者：Nguyen Xuan Nhiem、Phan Van Kiem、Chau Van Minh、Bui Huu Tai、Nguyen Xuan Cuong、Vu Kim Thu、Hoang Le Tuan Anh、Sung-Hoon Jo、Hae-Dong Jang、Young-In Kwon、Young Ho Kim

  DOI：10.1248/cpb.58.1408

  日期：——

  One new monoterpenoid glycoside, myresculoside (1), and eleven known compounds, were isolated from methanol extract of Myrica esculenta leaves by repeated column chromatography. The effects of these compounds on angiotensin I-converting enzyme (ACE) inhibition were investigated. Compounds 3 and 4 showed the most potent ACE inhibition with rates of 29.97% and 25.63% at concentration of 100 μM, respectively. Compounds 5, 6, and 11 showed weak activity with inhibitory rates of 0.07—1.41% at concentration of 100 μM.

  从接骨木叶的甲醇提取物中，通过重复柱层析分离出了一个新的单萜苷——梅果苷（myresculoside，1），以及十一种已知化合物。研究了这些化合物对血管紧张素 I 转化酶（ACE）抑制的影响。化合物 3 和 4 在100 μM浓度下表现出最强的 ACE 抑制活性，抑制率分别为 29.97% 和 25.63%。化合物 5、6 和 11 在100 μM浓度下表现出弱活性，抑制率为 0.07%—1.41%。
• ent-Kaurane Glycosides from Tricalysia okelensis
  作者：Wen-Hui Xu、Melissa Ruth Jacob、Ameeta Kishore Agarwal、Alice Mae Clark、Zong-Suo Liang、Xing-Cong Li

  DOI：10.1248/cpb.58.261

  日期：——

  Tricalysiosides V and W, two new ent-kaurane glycosides with an acylated disaccharide moiety at the C-3 position, were isolated from the roots of Tricalysia okelensis and their structures established by spectroscopic and chemical methods as ent-kauran-3α,16α,17-triol-19-al 3-O-[5-O-vanilloyl-β-D-apiopyranosyl(1→6)]-β-D-glucopyranoside (1) and ent-kauran-3α,16α,17-triol-19-al 3-O-[5-O-E-sinapoyl-β-D-apiopyranosyl(1→6)]-β-D-glucopyranoside (2).

  从鹅掌楸根中分离出了两种新的ent-kaurane苷V和W，它们的C-3位上有一个酰化的二糖分子，并通过光谱和化学方法确定了它们的结构，即ent-kauran-3α,16α、17-triol-19-al 3-O-[5-O-vanilloyl-β-D-apiopyranosyl(1→6)]-β-D-glucopyranoside (1) 和 ent-kauran-3α、16α,17-三醇-19-醛 3-O-[5-O-E-sinapoyl-β-D-apiopyranosyl(1→6)]-β-D-吡喃葡萄糖苷 (2)。
• Branched-chain sugars
  作者：W.G. Overend、A.C. White、N.R. Williams

  DOI：10.1016/s0008-6215(00)88003-9

  日期：1970.11

  Abstract The preparation of methyl 2,3- O -isopropylidene-β- l - erythro -pentopyranosid-4-ulose and the conversion of this compound into branched-chain sugar derivatives are described. Reactions at the carbonyl group in the pentopyranosid-4-ulose have been found to give, preferentially, products having the l - ribo configuration. A route to l -apiose is outlined.

  摘要描述了甲基2,3-O-异亚丙基-β-1-赤藓基-戊吡喃糖苷-4-ulose的制备及该化合物向支链糖衍生物的转化。已经发现在戊吡喃糖基-4-ulose中的羰基上的反应优选产生具有1-核糖构型的产物。概述了获得1-apiose的途径。
• Saponins and Polyphenols from <i>Fadogia ancylantha</i> (Makoni Tea)
  作者：Teresa Mencherini、Patrizia Picerno、Pasquale Del Gaudio、Michela Festa、Anna Capasso、Rita Aquino

  DOI：10.1021/np900466x

  日期：2010.2.26

  Three new saponins (1-3) and a known saponin, together with four known polyphenolic compounds, have been isolated from the fermented and dried leaves of Fadogia ancylantha (Makoni tea). The structures of compounds 1-3 were established by analysis of their spectroscopic data. Both all ethanol-water extract of F. ancylantha and its phenolic constituents showed significant free-radical-scavenging and antimicrobial activities. No cytotoxicity, its evaluated by analysis of hypodiploid nuclei in HUVEC cells using propidium iodide staining, was observed for either the plant crude extract or its constituents.
• Phenylethanoid Glycosides from <i>Lantana fucata</i> with <i>in Vitro</i> Anti-inflammatory Activity
  作者：Lisieux de Santana Julião、Anna Lisa Piccinelli、Stefania Marzocco、Suzana Guimarães Leitão、Cinzia Lotti、Giuseppina Autore、Luca Rastrelli

  DOI：10.1021/np9002383

  日期：2009.8.28

  A phytochemical analysis of Lantana fucata dried leaves led to the isolation of three new phenylethanoid glycosides, fucatosides A-C, along with parvifloroside A and six known methoxyflavones. Their structures were established by NMR and ESIMS experiments. In vitro assays showed that the alcoholic extract and fucatoside C have significant anti-inflammatory effects, inhibiting NO release in the LPS-induced J774.Al murine macrophage cell line.