糖原酸 | 5143-05-5

• 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
• 中文名称: 糖原酸
• 英文名称: gypsogeninic acid
• 英文别名: (3β,4α)-3-hydroxyolean-12-ene-23,28-dioic acid；gypsogenic acid；gypsogenin acid；acanjapogenin G；Gypsogeninsaeure；3β-Hydroxy-olean-12-en-23,28-disaeure；(3S,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-3-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid
• CAS: 5143-05-5
• 化学式: C₃₀H₄₆O₅
• 分子量: 486.692
• InChiKey: PAIBKVQNJKUVCE-JUENUIDLSA-N

物化性质

• 熔点：
  >300°C (dec.)
• 沸点：
  619.2±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  糖原酸 在 乙醚 、 potassium acetate 作用下， 生成 (3β,4α)-3-acetyloxyolean-12-ene-23,28-dioic acid dimethyl ester
  参考文献：
  名称：

  Wedekind; Schicke, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1930, vol. 190, p. 3,10

  摘要：

  DOI：
• 作为产物：
  描述：

  β-D-glucopyranosyl <β-D-glucuronopyranosyl-(1-> 3)>-3β-hydroxyolean-12-en-23-oic-28-oate 在 硫酸 作用下， 反应 6.0h， 生成 糖原酸
  参考文献：
  名称：

  Triterpene glycosides ofClimacoptera transoxana. IV. Structures of copterosides G and H

  摘要：

  DOI：

  10.1007/bf00574791

文献信息

• Three New Triterpenoid Saponins from &lt;i&gt;Dianthus superbus&lt;/i&gt;
  作者：Jian-Guang Luo、Xia Chen、Ling-Yi Kong

  DOI：10.1248/cpb.59.518

  日期：——

  Three new triterpenoid saponins (1-3) were isolated from the dried aerial parts of Dianthus superbus L. (Caryophyllaceae). Their structures were established as 3-O-β-D-glucopyranosyl gypsogenic acid 28-O-[β-D-6-O-((3S)-3-hydroxyl-3-methylglutaryl)glucopyranosyl(1→6)]-β-D-glucopyranoside (1), 3-O-β-D-glucopyranosyl gypsogenic acid 28-O-[β-D-glucopyranosyl(1→3)][β-D-6-O-((3S)-hydroxyl-3-methylglutar

  从石竹超级干（石竹科）的干燥地上部分中分离出三种新的三萜皂苷（1-3）。它们的结构被确定为3-O-β-D-吡喃葡萄糖基石膏酸28-O- [β-D-6-O-（（（3S）-3-hydroxyl-3-methylglutaryl）glucopyranosyl（1→6）]- β-D-吡喃葡萄糖苷（1），3-O-β-D-吡喃葡萄糖基葡糖酸28-O- [β-D-吡喃葡萄糖基（1→3）] [β-D-6-O-（（3S）-羟基-3-甲基戊二酰基）吡喃葡萄糖基（1→6）]-β-D-吡喃葡萄糖苷（2），3-O-α-L-阿拉伯吡喃糖基-3β，16α-二羟基油酸酯-12-en-23,28-二酸28 -O- [β-D-吡喃葡萄糖基-（1→6）]-β-D-吡喃葡萄糖苷（3），基于各种光谱分析和化学降解。
• Saponin and sapogenol. XXXII. Chemical constituents of the seeds of Vigna angularis (Willd.) Ohwi et Ohashi. (2). Azukisaponins I,II,III, and IV.
  作者：ISAO KITAGAWA、HUIKANG WANG、MASAYUKI SAITO、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.31.674

  日期：——

  Six oleanene-oligoglycosides named azukisaponins I (1), II (2), III (3), IV (4), V, and VI were isolated from azuki beans, the seeds of Vigna angularis (WILLD.) OHWI et OHASHI (Leguminosae). Among them, the structures of azukisaponins I, II, III, and IV were elucidated as 3-O-[β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl] sophoradiol (1), 3-O-[β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl] soyasapogenol B (2), 3-O[β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl] azukisapogenol (3), and 3-O-(β-D-glucopyranosyl)-28-O-[β-D-glucopyranosyl (1→6)-β-D-glucuronopyranosyl] gypsogenic acid (4), respectively on the basis of chemical and physicochemical evidence.

  从赤小豆（Vigna angularis (WILLD.) OHWI et OHASHI (豆科) 的种子）中分离出六种名为赤小豆皂苷 I (1)、II (2)、III (3)、IV (4)、V和 VI 的烯烃醇寡糖苷。其中，赤小豆皂苷 I、II、III 和 IV 的结构分别阐明为 3-O-[β-D-吡喃葡萄糖（1→2）-β-D-葡萄糖醛酸吡喃] 番荔枝醇 (1)、3-O-[β-D-吡喃葡萄糖（1→2）-β-D-葡萄糖醛酸吡喃] 大豆皂苷醇 B (2)、3-O[β-D-吡喃葡萄糖（1→2）-β-D-葡萄糖醛酸吡喃] 赤小豆皂苷醇 (3)、以及 3-O-(β-D-吡喃葡萄糖)-28-O-[β-D-吡喃葡萄糖（1→6）-β-D-葡萄糖醛酸吡喃] 石膏酸 (4)，这些均是基于化学和物理化学证据的结果。
• Vaccine Compositions For Marburg Virus
  申请人：Pathak Ashish Kumar

  公开号：US20120136142A1

  公开（公告）日：2012-05-31

  Methods and immunogenic compositions for generating an immune response against Marburg virus are provided. The immunogenic composition includes antigens obtained from a Marburg viral strain in combination with an oleanolic acid triterpene adjuvant.

  本发明提供了用于产生针对马尔堡病毒的免疫反应的方法和免疫原组合物。该免疫原组合物包括从马尔堡病毒株中获得的抗原，结合油酸三萜佐酸类佐剂。
• Gypsogenin Derivatives: An Unexpected Class of Inhibitors of Cholinesterases
  作者：Lucie Heller、Stefan Schwarz、Björn A. Weber、René Csuk

  DOI：10.1002/ardp.201400103

  日期：2014.10

  Gypsogenin (1) was obtained by acidic hydrolysis from its saponin. While the parent compound 1 acted as a selective inhibitor for butyrylcholinesterase (from equus) possessing a moderate mixed‐type inhibition of the enzyme, Ki values as low as 2.67 ± 0.59 μM were determined for (3β,4α) 3‐O‐acetyl‐olean‐12‐ene‐23,28‐dinitrile (11) and acetylcholinesterase (AChE, from electric eel). Thus, 11 possesses

  Gypsogenin (1) 是由其皂苷酸水解得到的。虽然母体化合物 1 作为丁酰胆碱酯酶（来自马科动物）的选择性抑制剂，对该酶具有中等混合型抑制作用，但对 (3β,4α) 3-O-乙酰基的 Ki 值低至 2.67 ± 0.59 μM olean-12-ene-23,28-二腈（11）和乙酰胆碱酯酶（AChE，来自电鳗）。因此，11 具有“金标准”加兰他敏氢溴酸盐抑制活性的五分之一；该化合物是最早被描述为有效的 AChE 选择性抑制剂的五环三萜之一。
• [EN] THERAPEUTIC COMBINATION OF GALNAC-OLIGONUCLEOTIDE CONJUGATE AND SAPONIN, AND USES THEREOF<br/>[FR] COMBINAISON THÉRAPEUTIQUE DE CONJUGUÉ GALNAC-OLIGONUCLÉOTIDE ET DE SAPONINE, ET SES UTILISATIONS
  申请人：SAPREME TECH BV

  公开号：WO2021261998A1

  公开（公告）日：2021-12-30

  The invention relates to a pharmaceutical combination comprising: a conjugate of an effector molecule and a ligand for ASGPR, wherein the ligand for ASGPR comprises at least one GalNAc moiety; and a saponin of the monodesmosidic or bidesmosidic triterpene glycoside type. The invention also relates to a pharmaceutical composition comprising the conjugate and the saponin. In addition, the invention relates to a pharmaceutical combination or composition of the invention, for use as a medicament, or for use in the treatment or prophylaxis of a disease or health problem in which an expression product is involved of any one or more of genes: apoB, TTR, PCSK9, ALAS1, ATS, GO, CCS, X gene of HBV, S gene of HBV, AAT and LDH, and/or for use in the treatment or prophylaxis of a cancer, an infectious disease, a viral infection, hypercholesterolemia, primary hyperoxaluria, haemophilia A, haemophilia B, AAT related liver disease, acute hepatic porphyria, TTR-mediated amyloidosis, hereditary TTR amyloidosis (hATTR), complement-mediated disease, hepatitis B infection, or an auto-immune disease. Furthermore, the invention relates to an in vitro or ex vivo method for transferring an effector molecule of the invention from outside a cell to inside said cell, preferably into the cytosol of said cell. The invention also relates to an in vitro or ex vivo method for transferring the conjugate of the invention from outside a cell to inside said cell.

  本发明涉及一种制药组合物，包括：一种效应分子和ASGPR配体的结合物，其中，ASGPR配体包括至少一个GalNAc基团；以及一种单脱单糖或双脱单糖三萜糖苷类皂苷。本发明还涉及一种包括该结合物和该皂苷的制药组合物。此外，本发明还涉及该制药组合物或制药组合物的用途，用于作为药物，或用于治疗或预防涉及以下一个或多个基因的疾病或健康问题的表达产物：apoB，TTR，PCSK9，ALAS1，ATS，GO，CCS，HBV的X基因，HBV的S基因，AAT和LDH；或用于治疗或预防癌症、传染病、病毒感染、高胆固醇血症、原发性高草酸尿症、血友病A、血友病B、AAT相关肝病、急性肝性卟啉病、TTR介导的淀粉样变性、遗传性TTR淀粉样变性（hATTR）、补体介导的疾病、乙型肝炎感染或自身免疫性疾病。此外，本发明还涉及一种从细胞外向细胞内转移本发明的效应分子的体外或体内方法，优选地进入该细胞的细胞质。本发明还涉及一种从细胞外向细胞内转移本发明的结合物的体外或体内方法。