zhankuic acid A | 163597-25-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: zhankuic acid A
• 英文别名: (6R)-2-methyl-3-methylidene-6-[(4S,5S,10S,13R,14R,17R)-4,10,13-trimethyl-3,7,11-trioxo-1,2,4,5,6,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]heptanoic acid
• CAS: 163597-25-9
• 化学式: C₂₉H₄₀O₅
• 分子量: 468.634
• InChiKey: DVORYMAGXQGBQK-QCMFUGJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  88.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  碘甲烷 、 zhankuic acid A 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以91%的产率得到zhankuic acid A methyl ester
  参考文献：
  名称：

  Chemoreversal Agents from Taiwanofungus Genus and Their More Potent Methyl Derivatives Targeting Signal Transducer and Activator of Transcription 3 (STAT3) Phosphorylation

  摘要：

  多药耐药性（MDR）是癌症治疗的主要障碍之一，其机制尚不完全清楚。近年来，人们发现信号转导和激活转录3（STAT3）是多药耐药机制的重要途径之一。在以往研究的基础上，我们发现占奎酸 A、B 和 C 对 MDR 癌细胞有附带的敏感性作用，而且占奎酸甲酯的 MDR 抑制活性优于其酸。因此，我们系统地研究了占奎酸甲酯衍生物对 MDR 癌细胞副敏感性的结构-活性关系。结果表明，化合物 12 的化学逆转活性最好，其逆转倍数为 692，紫杉醇联合 10 μM 化合物 12 处理 MDR KBvin 细胞的 IC50 值为 1.69 nM。在所有衍生物中，甲酯化合物的效果优于它们的酸类化合物，本研究对所有衍生物的结构-活性关系进行了详细讨论。此外，化合物 8、12 和 26 还能影响 KBvin 细胞中 STAT3 的活化，这也是其化学逆转作用的部分原因。我们的研究结果可能会为治疗耐多药癌症提供一种新的紫杉醇联合疗法，并为患者提供一种新的治疗选择。

  DOI：

  10.3390/ph14090916

文献信息

• Antcamphins A–L, Ergostanoids from <i>Antrodia camphorata</i>
  作者：Yun Huang、Xionghao Lin、Xue Qiao、Shuai Ji、Kedi Liu、Chi-tai Yeh、Yew-min Tzeng、Dean Guo、Min Ye

  DOI：10.1021/np400741s

  日期：2014.1.24

  Twelve ergostanoids, named antcamphins A–L (1–12), together with 20 known triterpenoids, were isolated from fruiting bodies of the medicinal fungus Antrodia camphorata. Compounds 1 and 2 represent the first examples of norergostanes isolated from A. camphorata, and compounds 3 and 4 are the first pair of cis–trans isomers of ergostane-type triterpenoids containing an aldehyde group. Compounds 5–12

  从药用真菌樟芝Antrodia camphorata的子实体中分离出十二种麦角类固醇，称为antcamphins A–L（1 – 12），以及20种已知的三萜类化合物。化合物1和2代表从樟脑曲霉中分离出的降冰片烷的第一个例子，化合物3和4是含醛基的麦角甾烷型三萜类化合物的第一对顺式-反式异构体。化合物5 – 12是四对C-25差向异构体。1 – 12的结构在广泛的光谱数据分析（包括NMR和HRESIMS）的基础上进行了阐明。特别是，通过改进的Mosher方法确定了C-25中5 – 12的绝对构型。这些三萜类化合物对MDA-MB-231乳腺癌细胞和A549肺癌细胞显示出弱的细胞毒活性，但在磺基罗丹明B试验中并未抑制正常细胞的生长。
• Method and composition for inhibiting virus infection
  申请人：ARJIL BIOTECH HOLDING COMPANY LIMITED

  公开号：US11253527B2

  公开（公告）日：2022-02-22

  The present invention pertains to a composition for preparing a medicament for preventing and/or treating a virus infection, especially a hepatitis B virus infection and/or a herpes simplex virus, and uses thereof.

  本发明涉及一种用于制备预防和/或治疗病毒感染（尤其是乙型肝炎病毒感染和/或单纯疱疹病毒感染）的药物组合物及其用途。
• Zhankuic Acid A and Analogs thereof and Their Use as an Anti-Inflammatory Agent
  申请人：National Cheng Kung University

  公开号：US20150374718A1

  公开（公告）日：2015-12-31

  Zhankuic acid A (ZAA) is the major pharmacologically active compound of Taiwanofungus camphoratus . We analyzed the structure of human TLR4/MD-2 complex with ZAA by X-score and HotLig modeling approaches. Two antibodies against MD-2 were used to verify the MD-2/ZAA interaction. The inflammation and survival of the mice pretreated with ZAA and injected with LPS were monitored. The modeling structure shows that ZAA binds the MD-2 hydrophobic pocket exclusively via specific molecular recognition; the contact interface is dominated by hydrophobic interactions. Binding of ZAA to MD-2 reduced antibody recognition to native MD-2, similar to the effect of LPS binding. Furthermore, ZAA significantly ameliorated LPS-induced endotoxemia and Salmonella -induced diarrhea in mice. Our results indicate that ZAA, which can compete with LPS for binding to MD-2 as a TLR4/MD-2 antagonist, is a potential therapeutic agent for Gram-negative bacterial infections.
• TRITERPENOID COMPOSITION OF ANTRODIA CINNAMOMEA, PREPARATION AND ANALYSIS METHOD THEREOF
  申请人：KAOHSIUNG MEDICAL UNIVERSITY

  公开号：US20170226150A1

  公开（公告）日：2017-08-10

  Disclosed are the isolation, purification and analysis of the triterpenoid compositions (including ergostane and lanostane) in the fruiting body of Antrodia cinnamomea using HPLC and NMR, as well as the stereo structures and the amounts of the triterpenoid compositions. The cytotoxicity of triterpenoids is also revealed. Based on the aforementioned techniques, the presence and amounts of ergostane and lanostane in the drugs, healthcare food or other goods are able to be detected.
• METHOD AND COMPOSITION FOR INHIBITING VIRUS INFECTION
  申请人：ARJIL BIOTECH HOLDING COMPANY LIMITED

  公开号：US20200268771A1

  公开（公告）日：2020-08-27

  The present invention pertains to a composition for preparing a medicament for preventing and/or treating a virus infection, especially a hepatitis B virus infection and/or a herpes simplex virus, and uses thereof.