20(R),24(S)-epoxy-3β,6α,25-trihydroxycycloartan-16-one | 86500-59-6

• 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: 20(R),24(S)-epoxy-3β,6α,25-trihydroxycycloartan-16-one
• 英文别名: 20R,24S-epoxycycloartan-3β,6α,25-triol-16-one；16-keto-cycloastragenol；cycloasalgenin；(1S,3R,6S,8R,9S,11S,12S,15S,16R)-6,9-dihydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-14-one
• CAS: 86500-59-6
• 化学式: C₃₀H₄₈O₅
• 分子量: 488.708
• InChiKey: GCJBMFXMOKDMRI-AFPSCHQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  环黄芪醇 在 吡啶 、 Dowex 50w*8(H⁺) 、 sodium methylate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 20(R),24(S)-epoxy-3β,6α,25-trihydroxycycloartan-16-one
  参考文献：
  名称：

  Saponin and sapogenol. XXXIV. Chemical constituents of astragali radix, the root of Astragalus membranaceus Bunge. (1). Cycloastragenol, the 9,19-cyclolanostane-type aglycone of astragalosides, and the artifact aglycone astragenol.

  摘要：

  分离出黄芪（韩国黄芪（豆科）的根）的三萜低聚糖苷成分。通过酶促和化学降解，得到 9, 19-环羊毛甾烷型三萜，命名为环黄芪醇 (1)，它是 11 种黄芪甲苷中 10 种中常见的真正苷元，以及 lanost-9 (II)-烯型对应物，命名为黄芪醇分离出(5)，其是由1二次形成的人工糖苷配基。根据化学和物理化学证据，环黄芪醇和黄芪醇的结构被阐明为(20R, 24S)-3β, 6α, 16β, 25-四羟基-20, 24-环氧-9, 19-环羊毛甾烷 (1) 和 ( 20R, 24S)-3β, 6α, 16β,分别为25-四羟基-20、24-环氧-羊毛脂-9(11​​)-烯(5)。

  DOI：

  10.1248/cpb.31.689

文献信息

• 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）。
• Triterpene glycosides from Astragalus and their genins. LXXXVII. Chemical transformation of cycloartanes. IX. Partial synthesis of cycloasalgenin
  作者：I. M. Isaev、D. A. Iskenderov、M. I. Isaev

  DOI：10.1007/s10600-010-9629-y

  日期：2010.7

  The natural cycloartane triterpenoid cycloasalgenin, which is 20R,24S-epoxycycloartan-3β,6α,25-triol16-one, was partially synthesized in three steps starting from cyclosiversigenin. In addition to the desired product, its 17-epimer was synthesized. The analogous 17-epimer was also prepared from cycloadsurgenin.

  从环藜芦素开始，通过三个步骤部分合成了天然环木菠萝烷三萜类化合物环藜芦素，即 20R,24S-环氧环木菠萝烷-3β,6α,25-三醇 16-酮。除所需产物外，还合成了其 17-表亚胺。类似的 17-epimer 也是由环泽兰素制备的。