高活性黄芪甲苷(环黄芪醇葡萄糖苷) | 86764-12-7

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: 高活性黄芪甲苷(环黄芪醇葡萄糖苷)
• 英文名称: brachyoside B
• 英文别名: (2R,3R,4S,5S,6R)-2-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-6,14-dihydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 86764-12-7
• 化学式: C₃₆H₆₀O₁₀
• 分子量: 652.866
• InChiKey: MHQQPTNPTWQCBN-XQZOPXIASA-N

物化性质

• 沸点：
  783.0±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  46
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  黄芪甲苷 IV	astragaloside IV	84687-43-4	C41H68O14	784.983
  ——	(3β,6α,16β,20R,24S)-20,24-epoxy-16-hydroxy-3-(β-D-xylopyranosyloxy)-9,19-cyclolanostane-6,25-diyl bis[β-D-glucopyranoside]	84687-46-7	C47H78O19	947.125
  异黄芪皂苷II	isoastragalosides II	86764-11-6	C43H70O15	827.02
  黄芪皂苷 II	(3b,6a,16b,20R,24S)-3-((2-O-acetyl-beta-D-xylopyranosyl)oxy)-20,24-epoxy-16,25-dihydroxy-9,19-cyclolanostan-6-yl beta-D-glucopyranoside	84676-89-1	C43H70O15	827.02
  异黄芪皂苷I	isoastragaloside I	84676-88-0	C45H72O16	869.057
  ——	(3β,6α,16β,20R,24S)-3-[(2,3-di-O-acetyl-β-D-xylopyranosyl)oxy]-20,24-epoxy-16,25-dihydroxy-9,19-cyclolanostan-6-yl β-D-glucopyranoside	84680-75-1	C45H72O16	869.057
  ——	acetylastragaloside I	84687-47-8	C47H74O17	911.094
  环黄芪醇	cycloastragenol	78574-94-4	C30H50O5	490.724

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  环黄芪醇	cycloastragenol	78574-94-4	C30H50O5	490.724

反应信息

• 作为反应物：
  描述：

  高活性黄芪甲苷(环黄芪醇葡萄糖苷) 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以11 mg的产率得到环黄芪醇
  参考文献：
  名称：

  Cyclosieversigenin 3-O-β-D-glucopyranoside fromAstragalus kuhitangi

  摘要：

  DOI：

  10.1007/bf02336091
• 作为产物：
  描述：

  (2S,3R,4R,5S,6S)-2-[(2S,3R,4S,5R)-4,5-dihydroxy-2-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]oxan-3-yl]oxy-6-methyloxane-3,4,5-triol 生成 高活性黄芪甲苷(环黄芪醇葡萄糖苷)
  参考文献：
  名称：

  XOLZINEVA, L. A.;SAVINA, A. A.;ZAXAROV, V. F.;MALDONADO, I. POMEPO, 2 KONF. NAUCH.-UCHEB. TSENTRA FIZ.-XIM. METODOV ISSLED., 21-24 FEVR., 198+

  摘要：

  DOI：

文献信息

• Saponin and sapogenol. XXXVII. Chemical constituents of astragali radix, the root of Astragalus membranaceus Bunge. (4). Astragalosides VII and VIII.
  作者：ISAO KITAGAWA、HUIKANG WANG、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.31.716

  日期：——

  By means of enzymatic degradation and by application of a selective cleavage method for the glucuronide linkage, as well as by the carbon-13 nuclear magnetic resonance (13C-NMR) analysis, the structures of two astragalosides, which were isolated as two of eleven astragalosidesfrom Astragali Radix (the root of Korean Astragalus membranaceus, Leguminosae), were elucidated : astragaloside VII is 3-O-β-D-xylopyranosyl-6-O-β-D-glucopyranosyl-25-O-β-D-glucopyranosyl-cycloastragenol (4) and astragaloside VIII is 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-xylopyranosyl (1→2)-β-D-glucuronopyranosyl] soyasap-ogenl B (8). Astragaloside VII (4) is an unprecedented example of a triterpene-tridesmoside.

  通过酶降解以及针对葡萄糖苷连接的选择性裂解方法结合碳-13核磁共振（13C-NMR）分析，阐明了从黄芪根（韩国黄芪，豆科植物）中分离出的两种黄芪苷的结构，这两种黄芪苷是十一种黄芪苷中的两种：黄芪苷VII为3-O-β-D-木糖吡喃糖基-6-O-β-D-葡萄糖吡喃糖基-25-O-β-D-葡萄糖吡喃糖基-环黄芪醇（4），黄芪苷VIII为3-O-[α-L-鼠李吡喃糖（1→2）-β-D-木糖吡喃糖（1→2）-β-D-葡萄糖醛酸吡喃糖]大豆皂苷B（8）。黄芪苷VII（4）是一个前所未有的三萜-三糖苷的例子。
• Functional Characterization and Protein Engineering of a Triterpene 3‐/6‐/2′‐ <i>O</i> ‐Glycosyltransferase Reveal a Conserved Residue Critical for the Regiospecificity
  作者：Meng Zhang、Yang Yi、Bai‐Han Gao、Hui‐Fei Su、Yang‐Oujie Bao、Xiao‐Meng Shi、Hai‐Dong Wang、Fu‐Dong Li、Min Ye、Xue Qiao

  DOI：10.1002/anie.202113587

  日期：2022.2.14

  We characterized the first plant cycloartane glycosyltransferase AmGT8 from A. membranaceus. Its mutants A394F, A394D, and T131V were discovered using semi-rational design, which showed specific 6-O, 3-O, and 2′-O glycosylation activities, respectively. This study uncovered a conserved residue critical for the regiospecificity of plant glycosyltransferases.

  我们对来自A. membranaceus的第一个植物环阿坦糖基转移酶 AmGT8 进行了表征。其突变体 A394F、A394D 和 T131V 是使用半理性设计发现的，它们分别显示出特定的 6- O、3 - O和 2' - O糖基化活性。这项研究发现了一个对植物糖基转移酶的区域特异性至关重要的保守残基。
• Compositions and methods for skin conditioning
  申请人：Harley Calvin B.

  公开号：US09248088B2

  公开（公告）日：2016-02-02

  Methods and cosmetic compositions for conditioning the skin, utilizing as active ingredients selected compounds structurally related to astragenols, cycloastragenols, and/or protopanaxatriols, are provided. Such compounds include those of formulas (I), (II) and (III) described herein.

  提供了一种使用结构与天然化合物astragenols、cycloastragenols和/或protopanaxatriols相关的选择性化合物作为活性成分来调理皮肤的方法和化妆品组合物。这些化合物包括本文所述的公式（I）、（II）和（III）的化合物。
• Saponin and sapogenol. XXXV. Chemical constituents of astragali radix, the root of Astragalus membranaceus Bunge. (2). Astragalosides I,II and IV, acetylastragaloside I and isoastragalosides I and II.
  作者：ISAO KITAGAWA、HUIKANG WANG、MASAYUKI SAITO、AKIRA TAKAGI、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.31.698

  日期：——

  Twelve triterpene-oligoglycosides were isolated from the glycosidic constituents of Astragali Radix, the root of Korean Astragalus membranaceus BUNGE. (Leguminosae). They were acetylastragaloside I (3), isoastragalosides I (5) and II (7), astragalosides I (4, major), II (6), III, IV (8), V, VI and VII, which contain a 9, 19-cyclolanostane cycloastragenol (1) as the aglycone, and astragaloside VIII and soyasaponin I (9), which possess an oleanene-type aglycone, soyasapogenol B. By means of chemical degradations, which included a selective cleavage method for the glucuronide linkage, and 13C-NMR examinations, the structure of astragaloside IV was elucidated as 3-O-β-D-xylopyranosyl-6-O-β-D-glucopyranosylcycloastragenol (8). In addition, the structures of five acetyl derivatives of 8 : acetylastragaloside I, astragaloside I, isoastragaloside I, astragaloside II and isoastragaloside II, were elucidated as 3-O-β-(2', 3', 4'-tri-O-acetyl)-D-xylopyranosyl- (3), 3-O-β-(2', 3'-di-O-acetyl)-D-xylopyranosyl- (4), 3-O-β-(2', 4'-di-O-acetyl)-D-xylopyranosyl- (5), 3-O-β-(2'-O-acetyl)-D-xylopyranosyl- (6) and 3-O-β-(3'-O-acetyl)-D-xylopyranosyl-6-O-β-D-glucopyranosylcycloastragenol (7), respectively.

  从朝鲜黄芪（Astragali Radix）（豆科植物朝鲜黄芪的根）的苷元成分中分离出 12 种三萜类寡糖苷。豆科它们是乙酰黄芪苷 I (3)，异黄芪苷 I (5) 和 II (7)，黄芪苷 I (4，主要)，II (6)，III，IV (8)，V，VI 和 VII，其中含有 9，19-环羊毛甾烷环黄芪烯醇 (1) 作为苷元，以及黄芪苷 VIII 和大豆皂苷 I (9)，其中含有齐墩果烯型苷元--大豆皂苷 B。通过化学降解（包括葡萄糖醛酸连接的选择性裂解方法）和 13C-NMR 检测，阐明了黄芪皂苷 IV 的结构为 3-O-β-D-xylopyranosyl-6-O-β-D-glucopyranosylcycloastragenol (8)。此外，8 的五个乙酰基衍生物的结构 ：乙酰基黄芪皂甙 I、黄芪皂甙 I、异黄芪皂甙 I、黄芪皂甙 II 和异黄芪皂甙 II 的结构分别为 3-O-β-（2'，3'，4'-三-O-乙酰基）-D-xylopyranosyl- (3)、3-O-β-（2'，3'-二-O-乙酰基）-D-xylopyranosyl- (4)、3-O-β-(2', 4'-di-O-acetyl)-D-xylopyranosyl- (5)、3-O-β-(2'-O-乙酰基)-D-xylopyranosyl- (6)和 3-O-β-(3'-O-乙酰基)-D-xylopyranosyl-6-O-β-D-glucopyranosylcycloastragenol (7)。
• CYCLOASTRAGENOL MONOGLUCOSIDE, PREPARATION, PHARMACEUTICAL COMPOSITION AND APPLICATION THEREOF
  申请人：Han Yingmei

  公开号：US20110218161A1

  公开（公告）日：2011-09-08

  This invention provides a method for preparing cycloastragenol monoglucoside CMG (cycloastragenol-6-O-β-D-glucoside), comprising the steps of: a. using astragaloside IV or Astragali extracts prepared by a conventional method as raw materials and adding an appropriate solvent thereinto to form a raw material solution; b. adding hydrolase and allowing for hydrolysis at a constant temperature to obtain a hydrolysate; c. separating the hydrolysate with macroporous adsorption resin; and d. obtaining the product by purification and separation. The present invention further provides cycloastragenol-6-O-β-D-glucoside prepared according to the method of this invention as well as its use in the preparation of a medicament for treating cardiovascular diseases and pharmaceutical compositions comprising the same.

  本发明提供了一种制备环状黄芪甙单葡萄糖苷CMG（环状黄芪甙-6-O-β-D-葡萄糖苷）的方法，包括以下步骤：a.使用天然黄芪甙IV或通过传统方法制备的黄芪提取物作为原材料，并加入适当的溶剂形成原料溶液；b.加入水解酶并在恒定温度下进行水解以获得水解产物；c.使用大孔吸附树脂分离水解产物；d.通过纯化和分离获得产品。本发明还提供了根据本发明方法制备的环状黄芪甙-6-O-β-D-葡萄糖苷，以及其在制备用于治疗心血管疾病的药物和包含该化合物的制药组合物中的用途。