黄芪醇 | 86541-79-9

• 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: 黄芪醇
• 英文名称: astragenol
• 英文别名: (3S,5R,6S,8S,10S,13R,14S,16S,17R)-17-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,7,8,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,6,16-triol
• CAS: 86541-79-9
• 化学式: C₃₀H₅₀O₅
• 分子量: 490.724
• InChiKey: KNESISUQBYQIIU-LOIFQKOGSA-N

物化性质

• 沸点：
  607.2±55.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)
• 溶解度：
  乙醇：50 mg/mL（101.89 mM；需要超声波）

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  黄芪醇 在 Jones reagent 作用下， 以 丙酮 为溶剂， 以72%的产率得到(5R,8S,10S,13R,14S,17S)-4,4,10,13,14-pentamethyl-17-[(2R)-2-methyl-5-oxooxolan-2-yl]-1,2,5,7,8,12,15,17-octahydrocyclopenta[a]phenanthrene-3,6,16-trione
  参考文献：
  名称：

  通过Baeyer-Villiger反应裂解A环并形成不寻常的去三萜骨架

  摘要：

  为了生成用于我们的生物学筛选研究的化合物库，对环黄芪醇进行了化学转化研究。Baeyer-Villiger氧化实验通过开环和随后的异常重排提供了一个有趣的3,5-seco-4-nor-triterpene骨架。描述了一种将三萜类化合物转化为3,5-seco-4-nor衍生物的新方法。

  DOI：

  10.1016/j.tetlet.2012.08.068
• 作为产物：
  描述：

  环黄芪醇 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以12 mg的产率得到黄芪醇
  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. 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.
  作者：ISAO KITAGAWA、HUIKANG WANG、AKIRA TAKAGI、MASAKO FUCHIDA、IWAO MIURA、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.31.689

  日期：——

  Triterpene-oligoglycoside constituents of Astragali Radix, the root of Korean Astragalus membranaceus BUNGE (Leguminosae), were isolated. By means of enzymatic and chemical degradations, the 9, 19-cyclolanostane-type triterpene named cycloastragenol (1), which was the common genuine aglycone of ten of eleven astragalosides, and the lanost-9 (II)-ene-type counterpart named astragenol (5), which was an artifact aglycone secondarily formed from 1, were isolated. On the basis of chemical and physicochemical evidence, the structures of cycloastragenol and astragenol were elucidated as (20R, 24S)-3β, 6α, 16β, 25-tetrahydroxy-20, 24-epoxy-9, 19-cyclolanostane (1) and (20R, 24S)-3β, 6α, 16β, 25-tetrahydroxy-20, 24-epoxy-lanost-9 (11)-ene (5), respectively.

  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)。
• [EN] AG-08 MOLECULE THAT IS A SAPOGENOL DERIVATIVE EXHIBITNG CYTOTOXIC EFFECTS BY ACTIVATING THE NECROSIS PATHWAY AND SYNTHESIS METHOD THEREOF<br/>[FR] PRODUCTION DE MOLÉCULE D'AG-08 QUI EST UN DÉRIVÉ DE SAPOGÉNOL PRÉSENTANT DES EFFETS CYTOTOXIQUES PAR ACTIVATION DE LA VOIE DE NÉCROSE ET SON PROCÉDÉ DE SYNTHÈSE
  申请人：IZMIR YUEKSEK TEKNOLOJI ENSTITUESUE

  公开号：WO2020222717A1

  公开（公告）日：2020-11-05

  The invention is related to an AG-08 coded novel structured molecule having cytotoxic features against cancer cells. The aim of the invention is to primarily synthesize the astragenol (AG) molecule from cycloastragenol (CA) and then from here, the cytotoxic molecule coded AG-08 which enables to kill cancer cells via a pathway that is non-apoptotic as a difference from the compounds that exhibit traditional anticancer activity.

  该发明涉及一种AG-08编码的新结构分子，具有对癌细胞的细胞毒性特征。该发明的目的是主要从黄芪甾醇（CA）合成黄芪甾醇（AG）分子，然后从这里，编码为AG-08的细胞毒性分子，通过一种非凋亡途径杀死癌细胞，与展示传统抗癌活性的化合物不同。
• Microbial Transformation of Cycloastragenol and Astragenol by Endophytic Fungi Isolated from <i>Astragalus</i> Species
  作者：Güner Ekiz、Sinem Yılmaz、Hasan Yusufoglu、Petek Ballar Kırmızıbayrak、Erdal Bedir

  DOI：10.1021/acs.jnatprod.9b00336

  日期：2019.11.22

  Biotransformation of Astragalus sapogenins (cycloastragenol (1) and astragenol (2)) by Astragalus species originated endophytic fungi resulted in the production of five new metabolites (3, 7, 10, 12, 14) together with 10 known compounds. The structures of the new compounds were established by NMR spectroscopic and HRMS analysis. Oxygenation, oxidation, epoxidation, dehydrogenation, and ring cleavage reactions were observed on the cycloartane (9,19-cyclolanostane) nucleus. The ability of the compounds to increase telomerase activity in neonatal cells was also evaluated. After prescreening studies to define potent telomerase activators, four compounds were selected for subsequent bioassays. These were performed using very low doses ranging from 0.1 to 30 nM compared to the control cells treated with DMSO. The positive control cycloastragenol and 8 were found to be the most active compounds, with 5.2- (2 nM) and 5.1- (0.5 nM) fold activations versus DMSO, respectively. At the lowest dose of 0.1 nM, compounds 4 and 13 provided 3.5- and 3.8-fold activations, respectively, while cycloastragenol showed a limited activation (1.5-fold).
• Cleavage of ring A and formation of an unusual nor-triterpene skeleton via the Baeyer–Villiger reaction
  作者：Özgür Tağ、Ali Çağır、Ikhlas A. Khan、Erdal Bedir

  DOI：10.1016/j.tetlet.2012.08.068

  日期：2012.10

  transformation studies. The Baeyer–Villiger oxidation experiments provided an interesting 3,5-seco-4-nor-triterpene skeleton via ring opening followed by an unusual rearrangement. A new methodology is described for transforming triterpenoids into 3,5-seco-4-nor derivatives.

  为了生成用于我们的生物学筛选研究的化合物库，对环黄芪醇进行了化学转化研究。Baeyer-Villiger氧化实验通过开环和随后的异常重排提供了一个有趣的3,5-seco-4-nor-triterpene骨架。描述了一种将三萜类化合物转化为3,5-seco-4-nor衍生物的新方法。