3β-hydroxy-11-oxo-18βH-olean-12-en-30-oic acid 3-O-[β-D-glucuronopyranosyl-(1->2)-β-D-glucuronopyranoside] trimethyl ester | 77345-90-5

• 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: 3β-hydroxy-11-oxo-18βH-olean-12-en-30-oic acid 3-O-[β-D-glucuronopyranosyl-(1->2)-β-D-glucuronopyranoside] trimethyl ester
• 英文别名: glycyrrhizic acid trimethyl ester；glycyrrhizin trimethyl ester；glycyrrhizin trimethylester；trimethyl glycyrrhizate；methyl (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-methoxycarbonyl-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-4,5-dihydroxy-6-methoxycarbonyloxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate
• CAS: 77345-90-5
• 化学式: C₄₅H₆₈O₁₆
• 分子量: 865.025
• InChiKey: ZKPBPGHLJIFHRS-DLHSVOQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  61
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  234
• 氢给体数：
  5
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-11-oxo-18βH-olean-12-en-30-oic acid 3-O-[β-D-glucuronopyranosyl-(1->2)-β-D-glucuronopyranoside] trimethyl ester 在 氢氧化钾 、 硫酸 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 (3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯
  参考文献：
  名称：

  Synthetic studies on the relationship between anti-HIV activities and micelle forming abilities of various alkylated glycyrrhetinate diglycoside sodium sulfates and related compounds

  摘要：

  Sodium sulfates 11-14, 29-32, 35 and 37 of various alkyl glycyrrhizin and related compounds were synthesized. In vitro anti-HIV activities of the sulfates were compared to the activities of glycyrrhizin 1 in the inhibition of replications of HTLV-III and GUN-4. The activities of the sulfates were increased 11.1, 15.2, 9.1 and 5.0 times for 11-14, 100.0, 125.5, 83.3 and 11.6 times for 29-32, and 11.6 and 50.0 times for 35 and 37. From the relationship between CMC values and anti-HIV activities of the sulfates, it appeared that the sulfates exhibiting more potent antiviral activities had higher micelle forming abilities. Sodium sulfates having a triterpenoid or steroid ring in the molecule showed more potent activities than those of thioglycosides which had no such ring. From the investigation of syncytium formation, we suggest that the active sulfates inhibited HIV-1 infection early in the replication cycle of the virus.

  DOI：

  10.1016/0223-5234(96)89163-x
• 作为产物：
  描述：

  重氮甲烷 、 (3beta,20beta)-20-羧基-11-氧代-30-去甲齐墩果-12-烯-3-基 2-O-beta-D-吡喃葡糖基-beta-D-吡喃葡糖苷酸 生成 3β-hydroxy-11-oxo-18βH-olean-12-en-30-oic acid 3-O-[β-D-glucuronopyranosyl-(1->2)-β-D-glucuronopyranoside] trimethyl ester
  参考文献：
  名称：

  High-Resolution 1H and 13C NMR of Glycyrrhizic Acid and Its Esters

  摘要：

  使用高分辨率 1H (600 MHz) 和 13C (150 MHz) NMR 方法确定甘草酸及其酯的 1H 和 13C NMR 谱中质子和 C 原子的共振。

  DOI：

  10.1007/s10600-005-0171-2

文献信息

• Apioglycyrrhizin and araboglycyrrhizin, two new sweet oleanene-type triterpene oligoglycosides from the root of Glycyrrhiza inflata.
  作者：Isao KITAGAWA、Masahiro SAKAGAMI、Fumi HASHIUCHI、Jun Liang ZHOU、Masayuki YOSHIKAWA、Jiali REN

  DOI：10.1248/cpb.37.551

  日期：——

  Two new sweet oleanene-type triterpene oligoglycosides, named apioglycyrrhizin and araboglycyrrhizin, were isolated from the air-drie root of Glycyrrhiza inflata [Chinese Glycyrrhizae Radix, Shinkyo-kanzo in Japanese], and their structures have been determined on the basis of chemical and physicochemical evidence.

  从胀果甘草（中药名为甘草，日文名为新娇甘）的干燥根中分离出两种新的甘遂型三萜寡糖苷，分别命名为芹菜苷甘草酸和阿拉伯苷甘草酸，并通过化学和物理化学证据确定了它们的结构。
• Saponin and Sapogenol. XLIX. On the Constituents of the Roots of Glycyrrhiza inflata BATALIN from Xinjiang, China. Characterization of Two Sweet Oleanane-Type Triterpene Oligoglycosides, Apioglycyrrhizin and Araboglycyrrhizin.
  作者：Isao KITAGAWA、Kazuyuki HORI、Masahiro SAKAGAMI、Fumi HASHIUCHI、Masayuki YOSHIKAWA、Jiali REN

  DOI：10.1248/cpb.41.1350

  日期：——

  Two sweet oleanane-type triterpene oligoglycosides named apioglycyrrhizin and araboglycyrrhizin were isolated from the air-dried roots of Glycyrrhiza inflata BATALIN, collected in Xinjiang province (Shinkyo-Kanzo in Japanese), together with glycyrrhizin (3), licorice-saponins A3 (8), G2 (10), and H2 (11) and known flavonoid glycosides. On the basis of chemical and physicochemical evidence, the structures of apioglycyrrhizin and araboglycyrrhizin have been determined to be expressed as 3-O-[β-D-apiofuranosyl(1→2)-β-D-glucuronopyranosyl]glycyrrhetic acid (1) and 3-O-[α-L-arabinopyranosyl(1→2)-β-D-glucuronopyranosyl]glycyrrhetic acid (2), respectively.During the course of these studies, it has been found that the hydroxyl groups in the oligosaccharide moiety of the glucuronide saponins may be partially methylated by prolonged treatment with diazomethane in methanol. The sweetness of the saponins hitherto isolated from various Glycyrrhizae Radix has been examined and a structure-sweetness relationship, as compared with glycyrrhizin, has been found.

  从新疆省（日文中的“新疆甘草”）采集的干燥甘草根中分离出两种甜味oleanane型三萜低聚糖苷，分别命名为apioglycyrrhizin和araboglycyrrhizin，同时分离出的还有甘草酸（3）、甘草皂苷A3（8）、G2（10）和H2（11）以及已知黄酮糖苷。根据化学和物理化学证据，确定apioglycyrrhizin和araboglycyrrhizin的结构分别为3-O-[β-D-apiofuranosyl(1→2)-β-D-glucuronopyranosyl]甘草亭酸（1）和3-O-[α-L-arabinopyranosyl(1→2)-β-D-glucuronopyranosyl]甘草亭酸（2）。在进行这些研究的过程中，发现通过在甲醇中长时间处理重氮甲烷，可以使葡萄糖苷皂苷的低聚糖部分中的羟基部分甲基化。对迄今为止从各种甘草根中分离出的皂苷的甜度进行了检测，并发现了与甘草酸相比的结构-甜度关系。
• [EN] GLYCYRRHIZIN OR DERIVATIVES THEREOF FOR TREATING OR PREVENTING SEVERE ACUTE RESPIRATORY SYNDROME (SARS)<br/>[FR] PROCEDES DE TRAITEMENT ET DE PREVENTION DU SYNDROME RESPIRATOIRE AIGU SEVERE (SRAS)
  申请人：JOHANN WOLFGANG GOETHE UNIVERS

  公开号：WO2004108122A1

  公开（公告）日：2004-12-16

  The invention provides methods for preventing, treating, managing or ameliorating viral infections, in particular, Severe Acute Respiratory Syndrome (SARS). More specifically, the invention provides methods for preventing, treating, managing or ameliorating a SARS-associated coronavirus or one or more symptoms thereof by administering Glycyrrhizin and/or derivatives thereof The invention also provides methods for preventing, treating, managing or ameliorating a SARS-associated coronavirus or one or more symptoms thereof by administering Glycyrrhizin and/or a derivative thereof in combination with a prophylactic or therapeutic agent other than Glycyrrhizin or a derivative thereof.

  本发明提供了预防、治疗、管理或改善病毒感染，特别是严重急性呼吸综合症（SARS）的方法。更具体地，本发明提供了通过给予甘草甜素及/或其衍生物来预防、治疗、管理或改善SARS相关冠状病毒或其一个或多个症状的方法。本发明还提供了通过给予甘草甜素及/或其衍生物与除甘草甜素或其衍生物之外的预防性或治疗性药剂的组合来预防、治疗、管理或改善SARS相关冠状病毒或其一个或多个症状的方法。
• Is 18α-Glycyrrhizin a real natural product? Improved preparation of 18α-Glycyrrhizin from 18β-Glycyrrhizin as a positive standard for HPLC analysis of licorice extracts
  作者：Kritamorn Jitrangsri、Kazuaki Kamata、Mana Akiba、Yoshie Yajiri、Masami Ishibashi、Jin Tatsuzaki、Tsutomu Ishikawa

  DOI：10.1007/s11418-021-01589-9

  日期：2022.3

  component of licorice (Glycyrrhiza sp.), which is widely used as a traditional medicine. Whether 18α-glycyrrhizin is a real natural product has been debated in the long history of glycyrrhizin chemistry because 18β-glycyrrhizin is epimerizable to a more thermodynamically stable 18α-glycyrrhizin under aqueous alkali conditions. We improved the preparation of 18α-glycyrrhizin from 18β-glycyrrhizin by successive

  18α-甘草甜素是18β-甘草甜素的差向异构体，是甘草的主要成分（Glycyrrhizasp.)，它被广泛用作传统药物。18α-甘草甜素是否是真正的天然产物在甘草甜素化学的悠久历史中一直存在争议，因为在碱性水溶液条件下 18β-甘草甜素可差向异构化为热力学更稳定的 18α-甘草甜素。我们通过 18β-甘草甜素的连续差向异构反应、所得差向异构混合物的三甲酯化和纯化的 18α-甘草甜素三甲酯的碱性水解改进了从 18β-甘草甜素制备 18α-甘草甜素的方法。使用合成的 18α-甘草甜素作为阳性标准，通过 HPLC 分析甘草提取物中可能存在 18α-甘草甜素的方法强烈表明，18α-甘草甜素可以作为甘草中甘草甜素衍生物的次要同源物自然存在物种。 图形概要
• Kitagawa, Isao; Kamigauchi, Toshiyuki; Ohmori, Hidenobu, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 10, p. 3078 - 3086
  作者：Kitagawa, Isao、Kamigauchi, Toshiyuki、Ohmori, Hidenobu、Yoshikawa, Masayuki

  DOI：——

  日期：——