lantanone | 14605-17-5

• 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: lantanone
• 英文别名: 3β-acetoxy-11-oxo-olean-12-en-28-oic acid；3-O-acetyl-11-oxo-18β-oleanolic acid；(4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-acetyloxy-2,2,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-4a-carboxylic acid
• CAS: 14605-17-5
• 化学式: C₃₂H₄₈O₅
• 分子量: 512.73
• InChiKey: UYMVUDWLGIYLKY-LYQIAVTOSA-N

物化性质

• 熔点：
  335 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  597.9±50.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  lantanone 在 sodium amalgam 、 乙醚 、 乙醇 作用下， 生成 methyl 3β-acetoxyoleana-11,13(18)-dien-28-oate
  参考文献：
  名称：

  Kitasato, Acta Phytochimica, 1936, vol. 9, p. 43,61, 75

  摘要：

  DOI：
• 作为产物：
  描述：

  齐墩果酸 在 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 cobalt(II) diacetate tetrahydrate 作用下， 以 四氢呋喃 、 乙酸乙酯 、 乙腈 为溶剂， 反应 77.0h， 生成 lantanone
  参考文献：
  名称：

  Synthesis of novel heterocyclic oleanolic acid derivatives with improved antiproliferative activity in solid tumor cells

  摘要：

  合成了一系列新的齐墩果烷咪唑碳酸酯、N-酰基咪唑或N-烷基咪唑，并对其在AsPC-1胰腺癌细胞中的抗增殖活性进行了表征和评估。构效关系分析显示，N-烷基咪唑27是最具活性的化合物，其诱导凋亡的能力与NOXA的上调和Bcl-xL的下调相关。进一步测试了化合物27在更多实体瘤细胞系中的抗增殖活性，其IC50值低于1 μM。

  DOI：

  10.1039/c3ob00011g

文献信息

• The preparation of some derivatives of glycyrrhetic acid and oleanolic acid
  作者：P D G DEAN、T G HALSALL、M W WHITEHOUSE

  DOI：10.1111/j.2042-7158.1967.tb08011.x

  日期：2011.4.12

  Some new derivatives of glycyrrhetic acid and oleanolic acid were prepared and characterized. Various combinations of the modified and normal functional groups were synthesized as required for a separate study of the uncoupling activities of glycyrrhetic acid and oleanolic acid. The hydroxyl functions of these two acids were modified to β-carboxypropionyl, acetyl and β-methoxycarbonylpropionyl esters. The carboxyl function of glycyrrhetic acid was converted to amide, p-amidobenzoic acid, o-amidobenzoic acid and the glycine conjugate of the acid. 11-Deoxy (glycyrrhetic acid) and 9,11-dehydro-11-deoxo (from both acids) analogues were prepared. 11-Oxo analogues of oleanolic acid were synthesized as well as the methyl esters.

  摘要：制备和表征了一些甘草酸和齐墩果酸的新衍生物。根据需要合成了修改和正常官能团的各种组合，以便对甘草酸和齐墩果酸的解耦活性进行单独研究。这两种酸的羟基功能被修改为β-羧丙酰基、乙酰基和β-甲氧羰基丙酰酯。甘草酸的羧基功能转化为酰胺、对-氨基苯甲酸、邻-氨基苯甲酸和该酸的甘氨酸结合物。制备了11-去氧（甘草酸）和9,11-脱氢-11-去氧（来自两种酸）的类似物。合成了齐墩果酸的11-酮类似物以及甲酯。
• Microbial transformation of glycyrrhetinic acid derivatives by Bacillus subtilis ATCC 6633 and Bacillus megaterium CGMCC 1.1741
  作者：Pingping Shen、Jian Zhang、Yuyuan Zhu、Wei Wang、Boyang Yu、Weiwei Wang

  DOI：10.1016/j.bmc.2020.115465

  日期：2020.6

  ATCC 6633 and Bacillus megaterium CGMCC 1.1741. Their structures were identified on the basis of extensive spectroscopic methods and nine of them were found for the first time. Two main types of reactions, regio- and stereo-selective hydroxylation and glycosylation, especially in the unactivated C-H bonds including C-11, C-19 and C-27, were observed in the biotransformation process, which greatly expand

  甘草次酸（GA）是甘草根的主要生物活性五环三萜糖苷配基，已知在抗溃疡，抗抑郁，抗炎和抗过敏方面起着至关重要的作用。在这项研究中，我们通过一系列化学反应半合成了五种GA衍生物。它们被选作生物转化的底物，并被枯草芽孢杆菌ATCC 6633和巨大芽孢杆菌CGMCC 1.1741产生13种代谢物。根据广泛的光谱学方法鉴定了它们的结构，并且首次发现了其中的九种。在生物转化过程中观察到两种主要类型的反应，区域和立体选择性羟基化和糖基化，特别是在未激活的CH键中，包括C-11，C-19和C-27，大大扩展了GA的化学多样性衍生品。测试了所有化合物对脂多糖（LPS）刺激的RAW 264.7细胞中一氧化氮（NO）生成的抑制作用。其中，olean-12-ene-3β，7β，15α，19α，30-pentol（16）和olean-12-ene-3β，7β，15α，27,30-pentol（17）对IC50表现出明显的抑制作用值分别为0
• Oxyfunctionalization Products of Terpenoids with Dimethyldioxirane and Their Biological Activity
  作者：Shoujiro Ogawa、Keiji Hosoi、Noriaki Ikeda、Mitsuko Makino、Yasuo Fujimoto、Takashi Iida

  DOI：10.1248/cpb.55.247

  日期：——

  Oxyfunctionalization of the bioactive terpenoids, ursolic acid acetate (1), oleanolic acid acetate (5), lupeol acetate (12), and kaurenic acid (17), with dimethyldioxirane (DMDO) was investigated. Treatment of the terpenoids with DMDO under mild conditions afforded a variety of oxidation and oxydegradation products to yield naturally occurring and/or novel compounds in one step. After chromatographic separation, the structures of the individual isolated products were determined using spectroscopic methods including several homonuclear (1H–1H) and heteronuclear (1H–13C) shift-correlated 2D-NMR techniques. The inhibitory activity of the terpenoid derivatives against α-glucosidase was investigated and compounds 1, 3, 7, and 9 were found to exhibit potent activity.

  研究人员用二甲基二氧环己烷（DMDO）对具有生物活性的萜类化合物熊果酸乙酸酯（1）、齐墩果酸乙酸酯（5）、羽扇豆醇乙酸酯（12）和高瑞香酸（17）进行了氧化官能化处理。在温和的条件下，用二甲基二氧环己烷处理萜类化合物，可产生多种氧化和氧降解产物，从而一步生成天然和/或新型化合物。色谱分离后，利用光谱方法（包括几种同核（1H-1H）和异核（1H-13C）位移相关的二维核磁共振技术）确定了各个分离产物的结构。研究了萜类衍生物对 α-葡萄糖苷酶的抑制活性，发现化合物 1、3、7 和 9 具有很强的活性。
• Simple Amides of Oleanolic Acid as Effective Penetration Enhancers
  作者：Barbara Bednarczyk-Cwynar、Danuta Partyka、Lucjusz Zaprutko

  DOI：10.1371/journal.pone.0122857

  日期：——

  delivery. In some cases it is necessary to use skin penetration enhancers in order to allow for the transdermal transport of drugs that are otherwise insufficiently skin-permeable. A series of oleanolic acid amides as potential transdermal penetration enhancers was formed by multistep synthesis and the synthesis of all newly prepared compounds is presented. The synthetized amides of oleanolic acid were tested

  透皮运输现在正成为最便捷，最安全的药物输送途径之一。在某些情况下，有必要使用皮肤渗透促进剂，以实现透皮运输药物，否则这些药物就不能充分渗透皮肤。通过多步合成形成了一系列齐墩果酸酰胺作为潜在的透皮渗透促进剂，并提出了所有新制备的化合物的合成。测试了齐墩果酸的合成酰胺的体外渗透促进剂活性。通过使用Fürst方法评估上述活性。介绍了所研究化合物的化学结构与渗透活性之间的关系。
• Hydroxamate triterpenoid derivatives
  申请人：VIVACELL BIOTECHNOLOGY ESPANA S.L.

  公开号：US10766855B2

  公开（公告）日：2020-09-08

  Triterpenoid derivatives and compositions comprising said triterpenoids derivatives of Formula (I) are described, wherein R═—C(O)NHOH. Said triterpenoids and compositions show capacity to bind PHD2, stabilize HIF-1α and HIF-2α proteins, activate the HIF pathway in different cell types, induce angiogenesis in human endothelial vascular cell, show neuroprotective activity in vitro and in vivo, antidiabetic activity and reduce the levels of lipids in vivo, and increase the plasma levels of Erythropoietin in vivo. The triterpenoid derivatives described act also in a selective manner and do not induce Nrf2 activation, NF-κB inhibition, STAT3 inhibition, and TGR5 activation, which are known activities of the natural triterpenoid precursors. Said triterpenoid derivatives are useful in the treatment of conditions and diseases which are responsive to HIF activation such as stroke, cerebral palsy, traumatic injuries and neurodegenerative diseases; and also IBD, myocardial ischaemia-reperfusion injury, acute lung injury, diabetic and chronic wounds, organ transplantation, acute kidney injury or arterial diseases.

  描述了式 (I) 的三萜类衍生物和包含所述三萜类衍生物的组合物，其中 R═-C(O)NHOH.所述三萜类化合物和组合物具有结合 PHD2 的能力，可稳定 HIF-1α 和 HIF-2α 蛋白，激活不同类型细胞中的 HIF 通路，诱导人内皮血管细胞的血管生成，在体外和体内显示神经保护活性，具有抗糖尿病活性，降低体内血脂水平，提高体内红细胞生成素的血浆水平。所述三萜类衍生物还具有选择性作用，不会诱导 Nrf2 激活、NF-κB 抑制、STAT3 抑制和 TGR5 激活，这些都是天然三萜类前体的已知活性。所述三萜类衍生物可用于治疗对 HIF 活化有反应的病症和疾病，如中风、脑瘫、创伤性损伤和神经退行性疾病；以及肠道疾病、心肌缺血再灌注损伤、急性肺损伤、糖尿病和慢性伤口、器官移植、急性肾损伤或动脉疾病。