(2R,3S,4S,5R,6R)-2-(羟基甲基)-6-[[(4S)-4-丙-1-烯-2-基-1-环己烯基]甲氧基]四氢吡喃-3,4,5-三醇 | 141206-20-4

• 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
• 中文名称: (2R,3S,4S,5R,6R)-2-(羟基甲基)-6-[[(4S)-4-丙-1-烯-2-基-1-环己烯基]甲氧基]四氢吡喃-3,4,5-三醇
• 中文别名: 磷羧基硫酸,甲基-,O-环戊基酯,(R)-(9CI)
• 英文名称: perillyl glucoside
• 英文别名: (S)-(-)-perillyl β-D-glucopyranoside；Perilloside A；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(4S)-4-prop-1-en-2-ylcyclohexen-1-yl]methoxy]oxane-3,4,5-triol
• CAS: 141206-20-4
• 化学式: C₁₆H₂₆O₆
• 分子量: 314.379
• InChiKey: YUTAFQVKXLDYFG-YTQIUSBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (S)-(-)-紫苏醇 在 氢氧化钾 、 氰化汞 作用下， 以 甲醇 、 苯 为溶剂， 反应 7.0h， 生成 (2R,3S,4S,5R,6R)-2-(羟基甲基)-6-[[(4S)-4-丙-1-烯-2-基-1-环己烯基]甲氧基]四氢吡喃-3,4,5-三醇
  参考文献：
  名称：

  Inhibitory Effect of Perillosides A and C, and Related Monoterpene Glucosides on Aldose Reductase and Their Structure-Activity Relationships.

  摘要：

  从紫苏（Perilla frutescens）叶中获得的单萜葡萄糖苷，紫苏苷A和C，被发现是醛糖还原酶（EC 1.1.1.21）的抑制剂，该酶被认为是糖尿病并发症如白内障的关键酶。紫苏苷A和C对大鼠晶状体醛糖还原酶的抑制作用相对于甘油醛是竞争性的，其Ki值分别为1.4×10-4和2.3×10-4M。它们的四乙酸酯对同一底物的抑制类型是非竞争性的，尽管其抑制效果比紫苏苷提高了大约一个数量级，Ki值分别为2.5×10-5和7.1×10-5M。我们还制备了相关的单萜葡萄糖苷及其四乙酸酯，并测定了它们对醛糖还原酶的抑制活性，以便阐明结构与抑制活性之间的关系。

  DOI：

  10.1248/cpb.43.920

文献信息

• Discovery of New Biocatalysts for the Glycosylation of Terpenoid Scaffolds
  作者：Lorenzo Caputi、Eng-Kiat Lim、Dianna J. Bowles

  DOI：10.1002/chem.200800548

  日期：2008.7.28

  potential biocatalysts from GT sequence information. To explore the potential of GTs as biocatalysts, their use for the production of terpenoid glycosides was investigated by using a microbial-based whole-cell biotransformation system capable of regenerating the cofactor, UDP-glucose. A high cell density fermentation system was shown to produce several hundred milligrams of a model terpenoid, geranyl-glucoside

  萜类糖苷的合成通常使用化学策略，因为几乎没有识别出识别这些支架的生物催化剂。在这项研究中，已针对一系列模型萜类受体筛选了107个重组糖基转移酶（GTs）平台，该平台包含拟南芥小分子GTs的多基因家族，以鉴定具有高活性的那些酶。27个GTs可以糖基化各种单萜，倍半萜和二萜，例如香叶醇，紫苏醇，青蒿酸和视黄酸。某些显示基本序列相似性的酶识别包含伯醇的萜类化合物，而与支架的线性或环状结构无关。其他含有仲和叔醇的GTs糖基化支架; 其他萜类化合物的羧基也代表了一种特征，这种特征先前已被GT认可，可以与许多不同的化合物形成葡萄糖酯。这些数据支持了根据GT序列信息对潜在生物催化剂的快速预测。为了探索GTs作为生物催化剂的潜力，通过使用能够再生辅因子UDP-葡萄糖的基于微生物的全细胞生物转化系统，研究了它们在生产萜类糖苷中的用途。高细胞密度发酵系统显示出可产生数百毫克模型萜烯，香叶基葡糖苷。关于GTs的
• Synthesis of Alkyl β -Glucosides by Transglucosylation Using Pyrococcus furiosus β -Glucosidase Immobilized onto Gelatin Gel
  作者：Yoh-ichi Matsushita、Hidetaka Nagatomo、Kazuhiro Sugamoto、Takanao Matsui

  DOI：10.2174/157017809787582762

  日期：2009.3.1

  Synthesis of alkyl β-glucosides such as p-anisyl β-D-glucopyranoside, phenethyl β-D-glucopyranoside, salidroside, cinnamyl β-D-glucopyranoside, citrusin D, 3-methylbutyl β-D-glucopyranoside, 3-methyl-2-butenyl β-Dglucopyranoside, geranyl β-D-glucopyranoside, perilloside A, and cyclohexyl β-D-glucopyranoside was accomplished in moderate yields by transglucosylation using hyperthermostable Pyrococcus furiosus β-glucosidase immobilized onto gelatin gel. Recovered immobilisate was reusable on successive runs in transglucosylation.

  合成烷基 β-吡喃葡萄糖苷，如对甲氧基苯甲酰 β-D-吡喃葡萄糖苷、苯乙基 β-D-吡喃葡萄糖苷、水杨梅苷、肉桂基 β-D-吡喃葡萄糖苷、柑橘苷 D、3-甲基丁基 β-D-吡喃葡萄糖苷、3-甲基-2-丁烯基 β-D-吡喃葡萄糖苷、使用固定在明胶凝胶上的超恒温 Pyrocmostable Furiosus β-葡萄糖苷酶，以中等产量完成了β-D-吡喃葡萄糖苷、香叶基 β-D-吡喃葡萄糖苷、紫苏糖苷 A 和环己基 β-D-吡喃葡萄糖苷的转葡糖基化。回收的固定化物可在连续的反式葡萄糖基化过程中重复使用。
• Silica gel-catalyzed β-O-glucosylation of alcohols with 1,2-anhydro-3,4,6-tri-O-pivaloyl-α-d-glucopyranose
  作者：Yoh-ichi Matsushita、Kazuhiro Sugamoto、Yoshio Kita、Takanao Matsui

  DOI：10.1016/s0040-4039(97)10315-x

  日期：1997.12

  1,2-Anhydro-3,4,6-tri-O-pivaloyl-alpha-D-glucopyranose (1a) was allowed to react with alcohols in the presence of solid acids such as silica gel and zeolite HY, to afford beta-O-glucosides stereoselectively. Several natural glucosides were synthesized by the application of the present reaction. (C) 1997 Elsevier Science Ltd.
• [EN] TREATMENT OF PREMENSTRUAL SYNDROME AND/OR MENSTRUAL DISCOMFORT WITH A COMPOSITION COMPRISING VICENIN-2<br/>[FR] TRAITEMENT DU SYNDROME PRÉMENSTRUEL ET/OU D'UNE GÊNE MENSTRUELLE PAR UNE COMPOSITION COMPRENANT DE LA VICÉNINE -2
  申请人：BESINS HEALTHCARE IRELAND LTD

  公开号：WO2020229412A1

  公开（公告）日：2020-11-19

  The present invention relates to compositions comprising Vicenin-2 that are useful in the treatment of female subjects suffering from premenstrual syndrome and/or menstrual discomfort. In particular embodiments, the invention relates to compositions comprising vicenin-2 in association with one or more further ingredients such as rosmarinic acid, clerodadienols, crocin, safranal, apigenins, vitamin D and magnesium. Furthermore, the invention relates to the prevention, curing and/or alleviation of at least one symptom associated with premenstrual syndrome and/or menstrual discomfort using the compositions of the invention.
• Inhibitory Effect of Perillosides A and C, and Related Monoterpene Glucosides on Aldose Reductase and Their Structure-Activity Relationships.
  作者：Tomoyuki FUJITA、Kumiko OHIRA、Kazutaka MIYATAKE、Yoshihisa NAKANO、Mitsuru NAKAYAMA

  DOI：10.1248/cpb.43.920

  日期：——

  Monoterpene glucosides, perillosides A and C, obtained from the leaves of Perilla frutescens, were found to be inhibitors of aldose reductase (EC 1.1.1.21) which is considered to be a key enzyme in diabetic complications such as cataract. The apparent type of inhibition of rat lens aldose reductase by perillosides A and C was competitive with respect to glyceraldehyde and their Ki values were 1.4×10-4 and 2.3×10-4M, respectively. The type of inhibition by their tetraacetates was non-competitive with respect to the same substrate, although their inhibitory effects were increased by about one order of magnitude compared with those of the perillosides and the Ki values were 2.5×10-5 and 7.1×10-5M, respectively. We also prepared related monoterpene glucosides and their tetraacetates and determined their inhibitory activities towards aldose reductase in order to elucidate the relationship between structure and inhibitory activity.

  从紫苏（Perilla frutescens）叶中获得的单萜葡萄糖苷，紫苏苷A和C，被发现是醛糖还原酶（EC 1.1.1.21）的抑制剂，该酶被认为是糖尿病并发症如白内障的关键酶。紫苏苷A和C对大鼠晶状体醛糖还原酶的抑制作用相对于甘油醛是竞争性的，其Ki值分别为1.4×10-4和2.3×10-4M。它们的四乙酸酯对同一底物的抑制类型是非竞争性的，尽管其抑制效果比紫苏苷提高了大约一个数量级，Ki值分别为2.5×10-5和7.1×10-5M。我们还制备了相关的单萜葡萄糖苷及其四乙酸酯，并测定了它们对醛糖还原酶的抑制活性，以便阐明结构与抑制活性之间的关系。