(20S,24R)-epoxy-12β-O-acetyl-dammarane-3β, 25-diol | 137201-09-3

• 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)-epoxy-12β-O-acetyl-dammarane-3β, 25-diol
• 英文别名: (20S,24R)-epoxy-12β-acetyldammarane-3β,25-diol；[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-3-hydroxy-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]phenanthren-12-yl] acetate
• CAS: 137201-09-3
• 化学式: C₃₂H₅₄O₅
• 分子量: 518.778
• InChiKey: YJMRWBFGYRRLNZ-FFUXOBCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  原人参二醇 在 吡啶 、 4-二甲氨基吡啶 、 乙酸酐 作用下， 反应 41.0h， 生成 (20S,24R)-epoxy-12β-O-acetyl-dammarane-3β, 25-diol
  参考文献：
  名称：

  具有抗菌活性的(20S，24R)-ocotillol型人参 皂苷类衍生物、其制备方法及用途

  摘要：

  本发明涉及有机合成和药物化学领域，具体涉及一类(20S，24R)‑ocotillol型人参皂苷类衍生物，结构如通式(I)。本发明还公开了这些(20S，24R)‑ocotillol型人参皂苷类衍生物的制备方法，含有它们的药物组合物及其抗细菌感染疾病用途。

  公开号：

  CN102924556B

文献信息

• Design, synthesis and biological evaluation of novel pyxinol derivatives with anti-heart failure activity
  作者：Junli Liu、Yunhe Liu、Hui Yu、Ying Zhang、Alan Chen-Yu Hsu、Mingming Zhang、Yawei Gou、Wei Sun、Fang Wang、Pingya Li、Jinping Liu

  DOI：10.1016/j.biopha.2020.111050

  日期：2021.1

  Natural products and its derivatives play a vital role in drug discovery and development owing to their efficacy and low toxicity. Pyxinol is a potent natural agent for cardiovascular disease. Thus we investigated the effect on ACE and HF of pyxinol derivatives. We designed and synthesized 32 novel fatty acid ester derivatives of pyxinol via esterification. Among them, compounds 2e (IC50=105 nM) and 3b

  心力衰竭（HF）是全球大量发病和死亡的重要原因。血管紧张素转换酶（ACE）是充血性心力衰竭的病因。天然产物及其衍生物由于其功效和低毒性而在药物开发中起着至关重要的作用。苯甲醇是治疗心血管疾病的有效天然药物。因此，我们研究了pyxinol衍生物对ACE和HF的影响。我们通过酯化反应设计并合成了32种新颖的pyxinol脂肪酸酯衍生物。其中，化合物2e（IC 50 = 105 nM）和3b（IC 50 = 114 nM）在体外显示出优异的ACE抑制活性，并且对H9c2细胞无毒。ACE与化合物之间的相互作用分别通过分子对接进行预测。在维拉帕米诱导的斑马鱼HF模型中，活性测定表明这两种衍生物可以剂量依赖性地改善心跳，静脉充血，心脏扩张，心输出量，射血分数和分数缩短的心血管生理指标。基于UPLC-QTOF-MS的血清代谢组学方法被用于探索潜在的机制。总共鉴定出25种分化的代谢产物和8种干扰的代谢途径
• Synthesis and biological evaluation of (20S,24R)-epoxy-dammarane-3β,12β,25-triol derivatives as α-glucosidase and PTP1B inhibitors
  作者：Xiao-Tong Yang、Tian-Ze Li、Chang-An Geng、Pei Liu、Ji-Jun Chen

  DOI：10.1007/s00044-021-02836-0

  日期：2022.2

  activity against α-glucosidase, and four compounds (8, 15, 26, 42) significantly inhibited PTP1B. It was noted that compounds 8 and 26 could inhibit both α-glucosidase and PTP1B as dual-target inhibitors with IC50 values of 489.8, 467.7 μM (α-glucosidase) and 319.7, 269.1 μM (PTP1B). Compound 26 was revealed to be a mix-type inhibitor on α-glucosidase and a noncompetitive-type inhibitor on PTP1B based

  我们之前的研究中从青钱柳中获得的达玛烷三萜(20 S ,24 R )-epoxy-dammarane-3 β ,12 β ,25- triol 在体外对α-葡萄糖苷酶有抑制活性，抑制率为32.2%。浓度为 200 μM。为了揭示构效关系（SARs）并获得更多活性化合物，对羟基进行化学修饰合成了(20 S ,24 R )-epoxy-dammarane-3 β ,12 β ,25-triol 的42个衍生物。 （C-3 和 C-12），环 A 和 E，并测定它们的α-葡萄糖苷酶和PTP1B抑制活性。两种化合物 ( 8 , 26 ) 增加了对α-葡萄糖苷酶的活性，四种化合物 ( 8 , 15 , 26 , 42 ) 显着抑制了 PTP1B。值得注意的是，化合物8和26作为双靶点抑制剂可同时抑制α-葡萄糖苷酶和 PTP1B，其 IC 50值为 489.8、467.7 μM（α-葡萄糖苷酶）和 319
• Pyxinol Fatty Acid Ester Derivatives J16 against AKI by Selectively Promoting M1 Transition to M2c Macrophages
  作者：Yaru Wang、Changcheng Li、Jingyi Chen、Xiaoli Cui、Binghuan Wang、Yuezeng Wang、Dayu Wang、Jinping Liu、Jing Li

  DOI：10.1021/acs.jafc.3c06979

  日期：2024.4.3

  responses, reducing macrophage inflammatory infiltration, and preferentially upregulating M2c macrophages. In conclusion, our study is the first to show that PJ16 resists AKI and fibrosis by mechanistically regulating macrophage function by modulating the phenotypic transition from M1 to M2 macrophages, mainly M2c macrophages.

  急性肾损伤 (AKI) 是一种常见的多原因临床疾病，如果忽视，通常会进展为慢性肾脏病 (CKD) 和终末期肾病，死亡率为 40-50%。然而，AKI 缺乏通用的治疗方法。炎症是早期肾损伤的基本病理改变，炎症可加剧AKI。巨噬细胞是参与肾脏疾病炎症微环境的主要免疫细胞。因此，调节巨噬细胞的功能是AKI干预的关键突破口。我们的团队对奥克替醇型人参皂苷pyxinol进行化学修饰，制备出具有更高溶解度和生物利用度的PJ16。在体外，利用LPS刺激的巨噬细胞模型，发现PJ16可以调节巨噬细胞功能，包括抑制炎症因子的分泌、促进吞噬作用、抑制M1巨噬细胞、促进M1向M2c巨噬细胞转变。进一步研究表明，PJ16 可能在体外保护 LPS 损伤的肾小管上皮细胞 (HK-2)。基于此，PJ16在单侧输尿管梗阻动物模型中得到验证，结果表明其通过降低炎症反应、减少巨噬细胞炎症浸润、优先上调M2c巨噬细胞来改善肾功能
• Synthesis and biological evaluation of novel ocotillol-type triterpenoid derivatives as antibacterial agents
  作者：Zhiwen Zhou、Cong Ma、Hengyuan Zhang、Yi Bi、Xia Chen、Hua Tian、Xiaoni Xie、Qingguo Meng、Peter John Lewis、Jinyi Xu

  DOI：10.1016/j.ejmech.2013.07.041

  日期：2013.10

  A novel class of ocotillol-type triterpenoid derivatives have been synthesized and evaluated for their in vitro antibacterial activity against several representative pathogenic bacterial strains. Compounds 20(S)-protopanaxadiol (PPD), 3, 5,16 and 24 exhibited potent antibacterial activity against Gram-positive bacteria. Compounds 3 and 5 also displayed promising antibacterial activity against a community-associated methicillin-resistant Staphylococcus aureus (CA-MRSA; strain USA300). Furthermore, compounds PPD, 3 and 16 combined with two commercially available antibiotics kanamycin and chloramphenicol showed strong synergistic inhibitory effects at their sub-MIC concentrations against S. aureus USA300 and Bacillus subtilis 168. Additionally, cytotoxic activity assay showed that the compounds tested did not affect cell viability of the human epithelial kidney (HEK-293) and human cervical (HeLa) cells at their MICs. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis, Cytotoxic, and Antibacterial Evaluation of C-12 Substituted Ocotillol-type Derivatives
  作者：Jiangong Liu、Xiaoyu Zhang、Shuo Wang、Huili Zhang、Zhiwen Zhou

  DOI：10.1134/s1068162023060249

  日期：2023.11