3-O-β-D-xylopyranosylcycloastragenol | 86541-83-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-O-β-D-xylopyranosylcycloastragenol
• 英文别名: cyclosiversigenin 3-O-β-D-xylopyranoside；cyclogaleginoside B；cyclosieversigenin 3-O-β-D-xylopyranoside；astramembrannin II；astramembranin II；(2S,3R,4S,5R)-2-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-9,14-dihydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]oxane-3,4,5-triol
• CAS: 86541-83-5
• 化学式: C₃₅H₅₈O₉
• 分子量: 622.84
• InChiKey: VXHVFDQYSSFKAR-MVRGBOKSSA-N

物化性质

• 沸点：
  745.5±60.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  44
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-O-β-D-xylopyranosylcycloastragenol 在 硫酸 作用下， 以 甲醇 为溶剂， 以23 mg的产率得到环黄芪醇
  参考文献：
  名称：

  Triterpene glycosides ofAstragalus and their genins. XVI. Cyclogaleginosides A and B fromAstraglus galegiformis

  摘要：

  DOI：

  10.1007/bf00574333
• 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 3-O-β-D-xylopyranosylcycloastragenol
  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

• 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)。
• Saponin and sapogenol. XXXVI. Chemical constituents of astragali radix, the root of Astragalus membranaceus Bunge. (3). Astragalosides III,V, and VI.
  作者：ISAO KITAGAWA、HUIKANG WANG、MASAYUKI SAITO、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.31.709

  日期：——

  Based on chemical and physicochemical investigations including carbon-13 nuclear magnetic resonance (13C-NMR) examinations and methylation analyses, the structures of three astragalosides, which were isolated from Astragali Radix, the root of Korean Astragalus membranaceus BUNGE (Leguminosae), were elucidated : astragaloside III is 3-O-[β-D-glucopyranosyl (1→2)-β-D-xylopyranosyl] cycloastragenol (3), astragaloside V is 3-O-[β-D-glucopyranosyl (1→2)-β-D-xylopyranosyl]-25-O-β-D-glucopyranosyl-cycloastragenol (5) and astragaloside VI is 3-O-[β-D-glucopyranosyl (1→2)-β-D-xylopyranosyl]-6-O-β-D-glucopyranosyl-cycloastragenol (6).

  根据碳-13 核磁共振（13C-NMR）检测和甲基化分析等化学和理化研究，阐明了从朝鲜黄芪（豆科植物黄芪的根）中分离出的三种黄芪皂苷的结构：黄芪皂苷Ⅲ是 3-O-[β-D-吡喃葡萄糖基（1→2）-β-D-吡喃木糖基] 环黄芪醇（3）、黄芪皂甙 V 是 3-O-[β-D-吡喃葡萄糖基（1→2）-β-D-吡喃木糖基]-25-O-β-D-吡喃葡萄糖基-环黄芪皂甙醇（5），黄芪皂甙 VI 是 3-O-[β-D-吡喃葡萄糖基（1→2）-β-D-吡喃木糖基]-6-O-β-D-吡喃葡萄糖基-环黄芪皂甙醇（6）。
• Synthetic Access Toward Cycloastragenol Glycosides
  作者：Ting Liu、Jin-Xi Liao、Yang Hu、Yuan-Hong Tu、Jian-Song Sun

  DOI：10.1021/acs.joc.7b00080

  日期：2017.4.21

  The first efficient synthetic approach toward four types of the cycloartane glycosides, the cycloastragenol 25-O; 3-O; 3,6-O-bis; and 3,25-O-bisglycoside, have been established, which featured the PPY-mediated, concentration-controlled acetylation and Au(I)-catalyzed Yu glycosylation. Through the synthetic investigation, the reactivity sequence of the four OHs in cycloastragenol was fixed for the first

  第一种有效的合成方法是对四种类型的环戊烷糖苷，环黄芪醇25- O进行合成。3- O ; 3，6- O- bis；已经建立了3，25- O-双糖苷，其特征在于PPY介导的，浓度控制的乙酰化和Au（I）催化的Yu糖基化。通过综合研究，首次确定了环黄芪醇中四个OH的反应序列，并发现了高效去除大的新戊酰基保护基的绕线策略。