人参皂苷Rk1 | 494753-69-4

• 物质功能分类: 生物化工 - 中草药成分
• 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: 人参皂苷Rk1
• 中文别名: 人参皂苷RK2
• 英文名称: 3β-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl]-5R,9R,13R-dammarane-20(21),24(25)-diene-12β-ol
• 英文别名: 3β,12β-dihydroxydammar-20(21),24-diene-3-O-β-D-glucopyranosyl(1->2)-β-D-glucopyranoside；Δ²⁰-ginsenoside Rg3；ginsenoside Rk₁；ginsenoside-Rk₁；ginsenoside YNK1；ginsenoside Rk1；(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-4,4,8,10,14-pentamethyl-17-(6-methylhepta-1,5-dien-2-yl)-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 494753-69-4
• 化学式: C₄₂H₇₀O₁₂
• 分子量: 767.011
• InChiKey: KWDWBAISZWOAHD-MHOSXIPRSA-N

物化性质

• 沸点：
  854.5±65.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)
• 溶解度：
  溶于甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  54
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  199
• 氢给体数：
  8
• 氢受体数：
  12

安全信息

• WGK Germany：
  3
• 储存条件：
  -20℃

制备方法与用途

用途

目的 本文通过酶法水解高纯度的人参皂苷Rk2获得其水解产物，并借助高分辨质谱和核磁确证结构。

功效与作用

人参皂苷Rk2能有效抑制肿瘤细胞生长，诱导癌细胞分化，并具有抗浸润及抗转移的疗效。

生物活性 Ginsenoside Rk1 的特点

• 来源：Ginsenoside Rk1 是高温加工人参提取得到的一种成分。
• 功能与作用：
  • 抗炎作用，抑制Jak2/Stat3信号通路和NF-κB的激活。
  • 具有抗肿瘤作用、抗血小板聚集活性、抗胰岛素抵抗、肾保护作用、抗菌作用以及认知功能增强等多种功效。
  • 通过触发细胞内活性氧(ROS)生成和阻断PI3K/Akt途径诱导细胞凋亡。

体外研究

• 抑制炎症因子：Ginsenoside Rk1（0-40 μM，6小时）可抑制脂多糖(LPS)诱导的MCP-1和TNF-α mRNA表达；在LPS刺激RAW264.7细胞中，40 μM时IL-1β表达受抑制。
• 抗炎作用：Ginsenoside Rk1（0-40 μM，24小时）剂量依赖性地抑制LPS诱导的JAK2和STAT3磷酸化。
• 抗癌活性：
  • 在MDA-MB-231细胞中，Ginsenoside Rk1（0-160 μM，48小时）导致细胞活力显著下降，分别为75.52 ± 2.51% (40 μM)，52.72 ± 2.54% (80 μM)，17.41 ± 2.94% (120 μM)和12.32% (160 μM)。
  • 导致G0/G1期细胞周期阻滞，并诱导MDA-MB-231细胞凋亡。

化学性质

• 外观：白色粉末。
• 溶解性：可溶于甲醇、乙醇和DMSO等有机溶剂。
• 来源：来源于人参。

用途

Ginsenoside Rk1 用于含量测定、鉴定及药理实验，具有抗癌和提高免疫功能、调节神经系统等多种药理作用。

反应信息

• 作为反应物：
  描述：

  ginsenoside Rg₅ 、 人参皂苷Rk1 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、241.32 kPa 条件下， 反应 16.0h， 生成 3-O-[β-D-glucopyranosyl(1-2)-β-D-glucopyranosyl]dammarane-3β,12β-diol
  参考文献：
  名称：

  [EN] TREATMENT AND PREVENTION OF CANCER WITH NEW GINSENOSIDE DERIVATIVES
  [FR] TRAITEMENT ET PREVENTION DU CANCER A L'AIDE DE NOUVEAUX DERIVES DE GINSENOSIDES

  摘要：

  本发明涉及一种在预防和治疗癌症方面有效的人参皂苷衍生物。更具体地说，本发明涉及具有新颖结构的人参皂苷衍生物，其在预防和治疗癌症方面具有有效性，以及它们的制备方法和一种包含上述新颖化合物作为活性成分的药物组合物。

  公开号：

  WO2005116042A1
• 作为产物：
  描述：

  人参皂甙 在 dodecatungstosilic acid 、 柠檬酸 作用下， 以 水 为溶剂， 反应 48.33h， 生成 人参皂苷Rk1
  参考文献：
  名称：

  一种利用原人参二醇组皂苷大规模转化生产 人参皂苷Rk1的方法

  摘要：

  本发明公开了一种利用原人参二醇组皂苷为原料大规模生产人参皂苷Rk1的方法，该方法包括在发酵罐中加入原人参二醇组皂苷和水，并通N2保护，经在线灭菌后加入有机酸和催化量的Keggin结构的杂多酸HxYW12O40·nH2O催化剂，其中Y选自P、Si、Fe或Zn，x为3或4，n为0‑30的正整数，在80~105℃下反应24~48小时，最后收集反应产物进行纯化即可得到高纯度的人参皂苷Rk1。本发明工艺简单易行，副反应少，产物纯度高，易于工业化生产。

  公开号：

  CN106008642B

文献信息

• Conversion of Ginsenoside Rb1 into Six Types of Highly Bioactive Ginsenoside Rg3 and Its Derivatives by FeCl<sub>3</sub> Catalysis
  作者：Hongshan Yu、Yu Wang、Chunying Liu、Jiamei Yang、Longquan Xu、Guanheng Li、Jianguo Song、Fengxie Jin

  DOI：10.1248/cpb.c18-00426

  日期：2018.9.1

  Ginsenoside Rb1 is an important saponin of ginseng(s); however, Rb1, with 3-O- and 20-O-sugar moieties, has low bioavailability. Here, we report the derivatization of ginsenoside Rb1 to completely generate six types of highly bioactive minor ginsenoside Rg3 and its derivatives by FeCl3 catalysis, the reaction conditions are similar to enzymatic reaction conditions. In FeCl3 catalysis, the only 20-O-sugar-moiety of ginsenoside Rb1 was decomposed into the minor ginsenosides Rk1 and Rg5 with newly produced C-20 ethylene bands; but also hydrolyzed into 20(S)-Rg3 and 20(R)-Rg3; subsequently the C-24(25) ethylene bands of 20(S)-Rg3 and 20(R)-Rg3 were hydrated to 20(S)-25-OH-Rg3 and 20(R)-25-OH-Rg3. After separation of reaction mixture from 34 g ginsenoside-Rb1 by silica-gel-column, the 3.3 g sample I of TLC top-band consisting of Rg5 and Rk1, 8.7 g sample II of TLC middle-band consisting of 20(S)-Rg3 and 20(R)-Rg3, 3.5 g sample III of TLC bottom-band consisting of unknown product-I and -II including 20(S)-25-OH-Rg3, were obtained. The sample III consisting of unknown product-I and -II was purified by crystallization, and identified to 20(S)-25-OH-Rg3 and 20(R)-25-OH-Rg3 by HPLC-Evaporative Light Scattering Detector (ELSD) and NMR. Therefore, six types of minor-ginsenosides Rk1, Rg5, 20(S)-Rg3, 20(R)-Rg3, 20(S)-25-OH-Rg3 and 20(R)-25-OH-Rg3 were successfully prepared from ginsenoside Rb1 by FeCl3 catalysis. FeCl3 has low toxicity and is inexpensive, and the reaction conditions are similar to enzymatic reaction conditions; thus, this method is applicable to the development of ginseng-based drugs.

  人参皂苷Rb1是人参的一种重要皂甙，但Rb1含有3-O-和20-O-糖基，生物利用度较低。在此，我们报道了利用 FeCl3 催化人参皂苷 Rb1 衍生化，完全生成六种高生物活性的次要人参皂苷 Rg3 及其衍生物，反应条件与酶促反应条件相似。在 FeCl3 催化下，人参皂苷 Rb1 中唯一的 20-O 糖基被分解成小人参皂苷 Rk1 和 Rg5，并产生新的 C-20 乙烯带；但也水解成 20(S)-Rg3 和 20(R)-Rg3；随后，20(S)-Rg3 和 20(R)-Rg3 的 C-24(25) 乙烯带水合生成 20(S)-25-OH-Rg3 和 20(R)-25-OH-Rg3。用硅胶凝胶柱从 34 g 人参皂苷-Rb1 中分离出反应混合物后，得到 3.3 g 由 Rg5 和 Rk1 组成的 TLC 上带样品 I，8.7 g 由 20(S)-Rg3 和 20(R)-Rg3 组成的 TLC 中带样品 II，3.5 g 由包括 20(S)-25-OH-Rg3 在内的未知产物-I 和-II 组成的 TLC 下带样品 III。由未知产物-I 和-II 组成的样品 III 经结晶纯化，并通过 HPLC-Evaporative Light Scattering Detector (ELSD) 和 NMR 鉴定为 20(S)-25-OH-Rg3 和 20(R)-25-OH-Rg3。因此，以人参皂苷Rb1为原料，通过FeCl3催化，成功制备了六种小人参皂苷Rk1、Rg5、20(S)-Rg3、20(R)-Rg3、20(S)-25-OH-Rg3和20(R)-25-OH-Rg3。FeCl3毒性低，价格便宜，反应条件与酶促反应条件相似，因此该方法适用于人参类药物的开发。
• Synthesis of Δ²⁰-Ginsenosides Rh₄, (20<i>E</i>)-Rh₃, Rg₆, and R<i>k</i>₁: A General Approach To Access Dehydrated Ginsenosides
  作者：Renzeng Shen、Stephane Laval、Xin Cao、Biao Yu

  DOI：10.1021/acs.joc.7b02987

  日期：2018.3.2

  Four representative Delta(20)-ginsenosides, namely, ginsenosides Rh-4 (1), (20E)-Rh-3 (2), Rg(6) (3), and Rk(1) (4) from Panax Ginseng, were chemically synthesized for the first time. Dehydration of the naturally occurring 20(S)-protopanaxatriol and 20(S)-protopanaxadiol provided all types of Delta(20)-sapogenins, which were separated due to a judicious choice of protecting groups. The Delta(20)-sapogenins were then directly glycosylated with glycosyl ortho-alkynylbenzoate donors under the catalysis of Ph3PAuNTf2 as key steps. The neutral conditions of the glycosylations were crucial to prevent the acid-labile Delta(20,21) double bond from isomerization.
• The chemical and hydroxyl radical scavenging activity changes of ginsenoside-Rb1 by heat processing
  作者：Yong Jae Lee、Hyun Young Kim、Ki Sung Kang、Jin Gyun Lee、Takako Yokozawa、Jeong Hill Park

  DOI：10.1016/j.bmcl.2008.07.056

  日期：2008.8

  The chemical and hydroxyl radical (.OH) scavenging activity changes of ginsenoside Rb-1 (Rb-1) by heat processing were investigated in this study. Rb-1 was changed into 20(S)-Rg(3), 20(R)-Rg3, Rk(1), and Rg(5) by heat processing through glucosyl elimination and epimerization of carbon-20 by SN1 reaction. The glucosyl moiety, separated from Rb-1, made Maillard reaction product (MRPs) with glycine. The generations of 20(S)-Rg(3) and MRPs were related to the increased OH scavenging activity of Rb-1 by heat processing. (c) 2008 Elsevier Ltd. All rights reserved.
• METHOD FOR MASS PRODUCTION OF GINSENOSIDE RH2-MIX
  申请人：INTELLIGENT SYNTHETIC BIOLOGY CENTER

  公开号：US20190112629A1

  公开（公告）日：2019-04-18

  The present invention relates to a method for mass production of ginsenoside Rh 2 -Mix. The present invention includes treating PPD-Mix with an organic acid and heat to obtain Rg 3 -Mix and treating the obtained Rg 3 -Mix using a recombinant GRAS strain in the Rg 3 -Mix to produce Rh 2 -Mix, and thereby facilitates the mass production of ginsenoside Rh 2 -Mix using β-glucosidase, which has been known to be difficult. Further, the present invention is advantageous in that the Rh 2 -Mix can be produced in high yield even at high temperatures, and mass production thereof for industrial purposes is practical as the production process is simple and more economical than direct use of an enzyme.
• [EN] TREATMENT AND PREVENTION OF CANCER WITH NEW GINSENOSIDE DERIVATIVES<br/>[FR] TRAITEMENT ET PREVENTION DU CANCER A L'AIDE DE NOUVEAUX DERIVES DE GINSENOSIDES
  申请人：PARK MYUNG HWAN

  公开号：WO2005116042A1

  公开（公告）日：2005-12-08

  The present invention relates to ginsenoside derivatives effective in prevention and treatment of cancer. More specifically, the present invention relates to ginsenoside derivatives with novel structures effective in prevention and treatment of cancers, method of their preparation, and a pharmaceutical composition comprising the above novel compounds as active ingredients.

  本发明涉及一种在预防和治疗癌症方面有效的人参皂苷衍生物。更具体地说，本发明涉及具有新颖结构的人参皂苷衍生物，其在预防和治疗癌症方面具有有效性，以及它们的制备方法和一种包含上述新颖化合物作为活性成分的药物组合物。