Rubososide

• 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: Rubososide
• 英文别名: steviol 13-O-β-glucopyranoside 19-β-glucopyranosyl ester；rubusoside；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,5R,9S,13S)-5,9-dimethyl-14-methylidene-13-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• 化学式: C₃₂H₅₀O₁₃
• 分子量: 642.741
• InChiKey: YWPVROCHNBYFTP-YXHQYMSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  45
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  216
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Rubososide 在 水 作用下， 生成 steviol
  参考文献：
  名称：

  Tanaka, Takashi; Kohda, Hiroshi; Tanaka, Osamu, Agricultural and Biological Chemistry, 1981, vol. 45, # 9, p. 2165 - 2166

  摘要：

  DOI：
• 作为产物：
  描述：

  可得然胶 、 steviol 以 乙醇 为溶剂， 反应 72.0h， 以10.6%的产率得到Rubososide
  参考文献：
  名称：

  桉树和小粒咖啡培养细胞对甜菊醇的生物转化

  摘要：

  摘要 从 Eucalyptus perriniana jar 发酵罐中分离出一种新的生物转化产物甜菊醇 19-β-龙胆二糖酯，以及甜菊醇 19-β-吡喃葡萄糖酯和甜菊醇 13-O -β-吡喃葡萄糖苷 19-β-吡喃葡萄糖苷（rubusoside）。给予甜菊醇后培养。仅从小粒咖啡细胞悬浮培养物中分离出甜菊糖苷作为甜菊醇的生物转化产物。

  DOI：

  10.1016/0031-9422(91)83450-y

文献信息

• Solubilization of Steviolbioside and Steviolmonoside with .GAMMA.-Cyclodextrin and Its Application to Selective Syntheses of Better Sweet Glycosides from Stevioside and Rubusoside.
  作者：Kazuhiro OHTANI、Yoko AIKAWA、Yoshiko FUJISAWA、Ryoji KASAI、Osamu TANAKA、Kazuo YAMASAKI

  DOI：10.1248/cpb.39.3172

  日期：——

  1, 4-α-Glucosylation at the 13-O-glycosyl moiety of stevioside (S) and rubusoside (RU) results in a significant increase of sweetness. Saponification of the 19-COO-β-glucosyl linkage of S and RU yielded steviolbioside (SB) (=13-O-β-sophorosyl-steviol) and steviolmonoside (SM) (=13-O-β-glucosyl-steviol), respectively, both of which are poorly soluble in an acetate buffer. It was found that the solubilities of SM and SB in the buffer solution were remarkably increased in the presence of γ-cyclodextrin (γ-CD). SB was solubilized in the buffer solution with the aid of γ-CD, and the solution was subjected to 1, 4-α-transglucosylation by using a cyclodextrin glucanotransferase-starch system to give a mixture of products which were glucosylated at the 13-O-glycosyl moiety. This mixture was acetylated, and the acetate was subjected to chemical β-glucosylation of 19-COOH followed by deacetylation to afford compounds which have superior sweetness to S. In the same way, derivatives with superior sweetness were selectively prepared from RU through SM.

  1、甜菊糖苷（S）和红没药苷（RU）的 13-O-糖基的 4-α-葡萄糖基化可显著增加甜度。对 S 和 RU 的 19-COO-β-葡萄糖基连接进行皂化，分别得到甜菊糖甙（SB）（=13-O-β-槐糖基-烷二醇）和甜菊糖单苷（SM）（=13-O-β-葡萄糖基-烷二醇），这两种物质在醋酸盐缓冲液中的溶解度都很低。研究发现，γ-环糊精（γ-CD）存在时，SM 和 SB 在缓冲溶液中的溶解度显著增加。借助 γ-CD 将 SB 溶解在缓冲溶液中，然后使用环糊精葡聚糖转移酶-淀粉系统对溶液进行 1，4-α-反式葡萄糖基化，得到在 13-O-糖基分子处被葡萄糖基化的产物混合物。这种混合物被乙酰化，乙酸酯经过 19-COOH 的化学β-葡萄糖基化，然后脱乙酰化，得到甜度优于 S 的化合物。
• Kitahata, Sumio; Ishikawa, Hiroshi; Miyata, Takeshi, Agricultural and Biological Chemistry, 1989, vol. 53, # 11, p. 2929 - 2934
  作者：Kitahata, Sumio、Ishikawa, Hiroshi、Miyata, Takeshi、Tanaka, Osamu

  DOI：——

  日期：——
• Kitahata, Sumio; Ishikawa, Hiroshi; Miyata, Takeshi, Agricultural and Biological Chemistry, 1989, vol. 53, # 11, p. 2923 - 2928
  作者：Kitahata, Sumio、Ishikawa, Hiroshi、Miyata, Takeshi、Tanaka, Osamu

  DOI：——

  日期：——