5-O-rutinosylnaringenin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 5-O-rutinosylnaringenin
• 英文别名: (2S)-5-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]naringenin；(2S)-5-O-[α-L-rhamnopyranosyl-(1-2)-β-D-glucopyranosyl]naringenin；(2S)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• 化学式: C₂₇H₃₂O₁₄
• 分子量: 580.543
• InChiKey: MWQGOZLFAPRRTD-OOVPPHLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  225
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  5-O-rutinosylnaringenin 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 L-鼠李糖 、 葡萄糖
  参考文献：
  名称：

  Bitter Taste Impact and Thermal Conversion of a Naringenin Glycoside from Cyclopia genistoides

  摘要：

  A naringenin derivative, isolated from Cyclopia genistoides, a bitter tasting herbal tea, especially when in green (unoxidized) form, was identified as (2S)-5[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranosy]oxylnaringenin (1). The compound partially epimerizes to (2R)-5-[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranosyloxy]naringenin (2) when heated at different temperatures (80, 90, 100, 110, and 120 degrees C) for a prolonged period in a phosphate buffer at pH 5. The fractional conversion model predicted the decrease in the concentration of compound 1 the best. The activation energy of the conversion reaction was calculated as 99.16 kJ mol(-1). Prolonged heating resulted not only in formation of compound 2 but eventually a decrease in its concentration and the formation of another conversion product, (E)-2'-[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranosyloxy]-4',6',4-trihydroxychal-cone (3). In contrast, naringin, glycosylated at C-7, remained stable when heated under the same conditions (100 degrees C for 6 h at pH 5). The bitter intensity of compound 1 was substantially less than that of naringin, both tested at 0.04 mM, a concentration typical of compound 1 in an herbal tea infusion of green C. genistoides. This comparison indicates that the position of the sugar moiety plays an important role in determining both bitter intensity and heat stability of naringenin glycosides.

  DOI：

  10.1021/acs.jnatprod.8b00710

文献信息

• Bitter Taste Impact and Thermal Conversion of a Naringenin Glycoside from <i>Cyclopia genistoides</i>
  作者：Ombeline Danton、Lara Alexander、Cindy Hunlun、Dalene de Beer、Matthias Hamburger、Elizabeth Joubert

  DOI：10.1021/acs.jnatprod.8b00710

  日期：2018.12.28

  A naringenin derivative, isolated from Cyclopia genistoides, a bitter tasting herbal tea, especially when in green (unoxidized) form, was identified as (2S)-5[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranosy]oxylnaringenin (1). The compound partially epimerizes to (2R)-5-[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranosyloxy]naringenin (2) when heated at different temperatures (80, 90, 100, 110, and 120 degrees C) for a prolonged period in a phosphate buffer at pH 5. The fractional conversion model predicted the decrease in the concentration of compound 1 the best. The activation energy of the conversion reaction was calculated as 99.16 kJ mol(-1). Prolonged heating resulted not only in formation of compound 2 but eventually a decrease in its concentration and the formation of another conversion product, (E)-2'-[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranosyloxy]-4',6',4-trihydroxychal-cone (3). In contrast, naringin, glycosylated at C-7, remained stable when heated under the same conditions (100 degrees C for 6 h at pH 5). The bitter intensity of compound 1 was substantially less than that of naringin, both tested at 0.04 mM, a concentration typical of compound 1 in an herbal tea infusion of green C. genistoides. This comparison indicates that the position of the sugar moiety plays an important role in determining both bitter intensity and heat stability of naringenin glycosides.