(20S,24R)-epoxydammarane-3β,6α,12β,25-tetrol

• 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: (20S,24R)-epoxydammarane-3β,6α,12β,25-tetrol
• 英文别名: 20(S),24(R)-Ocotillol；(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6,12-triol
• 化学式: C₃₀H₅₂O₅
• 分子量: 492.74
• InChiKey: XIGBHUXQOPWGDK-HTGHARJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (20S,24R)-epoxydammarane-3β,6α,12β,25-tetrol 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.5h， 生成 (20S,24R)-epoxy-3β-O-(L-alanyl)-dammarane-6α.12β,25-triol
  参考文献：
  名称：

  邻苯二酚和邻苯二酚的氨基酸衍生物的合成及抗肝癌作用

  摘要：

  为了寻求一种有效的低毒性抗肝癌药物，合成了两种活性的邻苯二酚型皂苷元（pyxinol和ocotillol）的总共24个氨基酸衍生物（20个新衍生物以及4个已知衍生物）。评价了衍生物的体外和体内抗肝癌作用。首先，使用HepG2人癌细胞来评估其抗癌活性。与pyxinol或ocotillol相比，大多数衍生物显示出明显增强的活性。其中，化合物2e表现出最优异的活性，IC 50值为11.26±0.43 µM。接下来，使用H22肝癌小鼠进一步评估化合物2e的抗肝癌活性。结果表明，化合物2e或化合物2e与环磷酰胺（CTX）联合治疗可显着抑制H22移植瘤的生长（p <0.05，p <0.01），抑瘤率分别为35.32％和55.30％。 ， 分别。更重要的是，与CTX引起明显的毒性相反，化合物2e对肝脏和肾脏的损害有限。最后，化合物2e的潜在机理通过基于超高效液相色谱四极杆飞行时间质谱（UPLC-QTOF

  DOI：

  10.3390/molecules26040780
• 作为产物：
  描述：

  原人参三醇 在 吡啶 、 咪唑 、 palladium hydroxide, 20 wt% on carbon 、 camphor-10-sulfonic acid 、 氢气 、 sodium hydride 、 间氯过氧苯甲酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 80.0h， 生成 (20S,24R)-epoxydammarane-3β,6α,12β,25-tetrol
  参考文献：
  名称：

  Synthesis of Ocotillol-Type Ginsenosides

  摘要：

  A total of 14 ocotillol-type ginsenosides were conveniently synthesized employing glycosylation of ocotillol sapogenin derivatives with glucosyl ortho-alkynylbenzoate donors under the promotion of a gold(I) catalyst as the key step. Relying on a rational protecting group strategy and the unexpected regioselectivity of the glycosylation of the 3,25-diol sapogenins (2a/2b, 5a/5b) for the tertiary 25-OH, mono 3-O-glucosyl ocotillol-PPD, 6-O-glucosyl ocotillol-PPT, 25-O-glucosyl ocotillol-PPD/PPT and 3,25-di-O-glucosyl ocotillol-PPD/PPT ginsenosides were prepared in which the configuration at the C-24 is either R or S.

  DOI：

  10.1021/acs.joc.6b01265

文献信息

• (20S,24R)-ocotillol型人参皂苷脂肪酸衍生物及制备方法和用途
  申请人：吉林大学

  公开号：CN110540573A

  公开（公告）日：2019-12-06

  本发明提供一种(20S,24R)‑ocotillol型人参皂苷脂肪酸衍生物及制备方法和用途，涉及有机合成与药物化学领域。本发明化合物与含有此化合物的药物组合物在制备治疗慢性阻塞性肺疾病的药物中的应用。本发明提供在(20S,24R)‑ocotillol型人参皂苷类化合物作用下IL‑6和IL‑10表达水平的变化与COPD的相关性，有助于深入了解炎症因子的具体作用机制，从而为进一步研究预防或治疗慢性阻塞性肺疾病药物打下坚实基础。
• Synthesis, Structural Determination of a New Ocotillol Derivative and its Epimer
  作者：Meng Qingguo、Bi Yi、Wang Liang、Jiang Naicaiv、Jiang Yongtao、Zhang Jiangfeng、Yi Songtao、Sun Haijun

  DOI：10.2174/157017811799304377

  日期：2011.11.1

  Epimeric 20S, 24-epoxy-dammarane-3β, 6α, 12β, 25-tetraol acetic ester was synthesized from 20(S)- protopanaxatriol in the presence of acetic anhydride and the product oxidated by m-CPBA. 20S, 24R-epoxy dammarane- 3β, 6α, 12β, 25-tetraol (ocotillol derivative) and its epimer were synthesized by saponification in the presence of sodium hydroxide in 1:1 molar ratio. The structures of the two compounds were characterized by X-ray diffraction method. The results showed the configuration of C-24 of two epimers as S-form (4, ocotillol derivative) and R-form (3, epimer), respectively.

  在乙酸酐存在下，将20(S)-原人参三醇与m-CPBA氧化，合成出表异构体20S，24-环氧-达玛烷-3β，6α，12β，25-四醇乙酸酯。在氢氧化钠存在下，以1:1的摩尔比进行皂化反应，合成出20S，24R-环氧达玛烷-3β，6α，12β，25-四醇（奥科替醇衍生物）及其表异构体。通过X射线衍射法对两种化合物的结构进行了表征。结果表明，两种表异构体的C-24构型分别为S型（4，奥科替醇衍生物）和R型（3，表异构体）。
• (20S,24R)-ocotillol型人参皂苷甘氨酸衍生物、其制备方法及用途
  申请人：吉林大学

  公开号：CN111100177B

  公开（公告）日：2022-02-08

  本发明涉及新化合物(20S,24R)‑ocotillol型人参皂苷甘氨酸衍生物、其制备方法及用途，属于医药领域。化合物化学名为(20S,24R)‑3‑O‑氨基乙酰基‑达玛‑20,24‑环氧‑3β,6α,12β,25‑四醇。取Ocotillol适量，与BOC‑Gly、DMAP、EDCI和DIPEA一起室温反应，乙酸乙酯稀释，乙酸乙酯萃取，合并有机相，柱层析纯化后溶于二氯甲烷，加入TFA室温反应，二氯甲烷萃取，合并有机相，柱层析纯化获得所述化合物。实验结果证明，(20S,24R)‑ocotillol型人参皂苷甘氨酸衍生物对不可分型流感嗜血杆菌(NTHi)所致激素抵抗性哮喘疾病实验模型小鼠的肺功能有保护作用，并能改善其激素耐药。本发明的(20S,24R)‑ocotillol型人参皂苷甘氨酸衍生物作为药物活性成分，为激素抵抗性哮喘的预防和治疗提供临床指导与依据，改善患者对激素的耐药情况，进而减轻患者痛苦，改善患者生活质量。
• Stereoselective oxidation metabolism of 20(<i>S</i>)-protopanaxatriol in human liver microsomes and in rats
  作者：Wenyan Wang、Yingying Ni、Li Wang、Xin Che、Wanhui Liu、Qingguo Meng

  DOI：10.3109/00498254.2014.986562

  日期：2015.5.4

  1. In this study, the oxidative metabolites of 20(S)-protopanaxatriol (PPT) were identified in human liver microsomes (HLMs) and in rats using liquid chromatography-electrospray ionization tandem mass spectrometry.2. Twelve oxidative metabolites were found in HLM, eight of which have not been previously reported. Twenty-four oxidative metabolites were found in rat feces after oral administration and 20 of these, including six found in HLM, were first reported. The results indicated PPT was more extensively metabolized in rats than in HLM. C20-24 epoxides, a pair of epimers (namely, M1-1 and M1-2) were the major metabolites, and other metabolites were derived from their further metabolism.3. Enzyme kinetics experiments showed that the apparent formation V-max of M1-1 was 10.4 folds and 2.4 folds higher than that of M1-2 in HLM and in rat liver microsomes (RLMs), respectively. The depletion rate of M1-2 was 11.0 folds faster than M1-1 in HLM, and was similar in RLM. Hence, the remarkable species differences of PPT metabolism mainly resulted from the stereoselective formation and further metabolic elimination of M1-1 and M1-2.4. Chemical inhibition study and recombinant human P450 isoforms analysis showed that CYP3A4 was the predominant isoform involved in the oxidative metabolism of M1-1 and M1-2.
• Biotransformation of 20(S)-protopanaxatriol by Aspergillus niger and the cytotoxicity of the resulting metabolites
  作者：Guangtong Chen、Yan Song、Hongjuan Ge、Jie Ren、Xue Yang、Jianlin Li

  DOI：10.1016/j.phytol.2014.11.006

  日期：2015.3

  The microbial transformation of 20(S)-protopanaxatriol by cell suspension cultures of Aspergillus niger AS 3.1858 yielded metabolites 1-13. The chemical structures of these transformed products were elucidated based on various spectroscopic analyses, including 1D and 2D NMR and HRESIMS. Metabolites 3, 11, and 13 are new compounds. Furthermore, metabolite 3 exhibited relative better activity profile toward the tested seven cancer cell lines (Du-145, Hela, K562, K562/ADR, SH-SY5Y, HepG2, and MCF-7) than substrate and preliminary structure-activity relationships were concluded. (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.