麦角甾-8,24(28)-二烯-26-酸,7-羟基-4-甲基-3,11-二羰基-,(4a,5a,7b,25S)- | 163565-76-2

• 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
• 中文名称: 麦角甾-8,24(28)-二烯-26-酸,7-羟基-4-甲基-3,11-二羰基-,(4a,5a,7b,25S)-
• 英文名称: antcin C
• 英文别名: (25S)-antcin C；(4alpha,5alpha,7beta,25S)-7-Hydroxy-4-methyl-3,11-dioxoergosta-8,24(28)-dien-26-oic acid；(2S,6R)-6-[(4S,5S,7S,10S,13R,14R,17R)-7-hydroxy-4,10,13-trimethyl-3,11-dioxo-2,4,5,6,7,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-3-methylideneheptanoic acid
• CAS: 163565-76-2
• 化学式: C₂₉H₄₂O₅
• 分子量: 470.649
• InChiKey: TWISSXUWVGIUBP-IRXLFGEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-(-)-1-(9-蒽基)-2,2,2-三氟乙醇 、 麦角甾-8,24(28)-二烯-26-酸,7-羟基-4-甲基-3,11-二羰基-,(4a,5a,7b,25S)- 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 氘代氯仿 为溶剂， 反应 24.0h， 生成 E3-RAT
  参考文献：
  名称：

  Antcamphins A–L，来自樟芝牛角的类胡萝卜素

  摘要：

  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。

  DOI：

  10.1021/np400741s

文献信息

• TRITERPENOID COMPOSITION OF ANTRODIA CINNAMOMEA, PREPARATION AND ANALYSIS METHOD THEREOF
  申请人：WU YANG-CHANG

  公开号：US20120190871A1

  公开（公告）日：2012-07-26

  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.

  本发明揭示了采用HPLC和NMR技术从红树孔菌子实体中分离、纯化和分析三萜类化合物（包括麦角甾烷和榄香甾烷），以及三萜类化合物的立体结构和含量。此外，还揭示了三萜类化合物的细胞毒性。基于上述技术，能够检测到药物、保健食品或其他商品中麦角甾烷和榄香甾烷的存在和含量。
• Chemoreversal Agents from Taiwanofungus Genus and Their More Potent Methyl Derivatives Targeting Signal Transducer and Activator of Transcription 3 (STAT3) Phosphorylation
  作者：Ko-Hua Yu、Chin-Chuan Hung、Tian-Shung Wu、Chin-Fu Chen、I-Ting Wu、Ping-Chung Kuo、Sio-Hong Lam、Hsin-Yi Hung

  DOI：10.3390/ph14090916

  日期：——

  Multidrug resistance (MDR), for which the mechanisms are not yet fully clear, is one of the major obstacles to cancer treatment. In recent years, signal transducer and activator of transcription 3 (STAT3) were found to be one of the important MDR mechanism pathways. Based on the previous research, zhankuic acid A, B, and C were found to have collateral sensitivity effects on MDR cancer cells, and MDR inhibitory activity of zhankuic acid methyl ester was found to be better than that of its acid. Therefore, we executed a systematic examination of the structure–activity relationship of zhankuic acid methyl ester derivatives to collateral sensitivity in MDR cancer cells. The results showed that compound 12 is the best in terms of chemoreversal activity, where the reversal fold was 692, and the IC50 value of paclitaxel combined with 10 μM compound 12 treatment was 1.69 nM in MDR KBvin cells. Among all the derivatives, methyl ester compounds were found to be better than their acids, and a detailed discussion of the structure–activity relationships of all of the derivatives is provided in this work. In addition, compounds 8, 12, and 26 were shown to influence the activation of STAT3 in KBvin cells, accounting for part of their chemoreversal effects. Our results may provide a new combined therapy with paclitaxel to treat multidrug-resistant cancers and provide a new therapy option for patients.

  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。
• Regio-specific enzymatic glucosylation of triterpenoids from <i>Antrodia camphorata</i> and their biological activities
  作者：Hui-Fei Su、Bin Li、Yang Yi、Meng Zhang、Rong Yu、Yang-Oujie Bao、Kuan Chen、Min Ye

  DOI：10.1039/d3ob01286g

  日期：——

  The bacterial glycosyltransferase YjiC1 was used to glycosylate triterpenoids from the medicinal fungus Antrodia camphorata. Eleven new compounds were obtained from enzymatic reactions. Glucosylation could increase the inhibitory activities against COX-2, and improve the anti-inflammatory activities of Antrodia ergostanes on acute lung injury mice, especially (25R)-antcin C 7-O-β-D-glucoside.

  细菌糖基转移酶 YjiC1 用于糖基化药用真菌牛樟芝中的三萜类化合物。通过酶促反应获得了十一种新化合物。糖基化可增加牛樟芝对COX-2的抑制活性，提高牛樟芝对急性肺损伤小鼠的抗炎活性，尤其是( 25R )-antcin C 7- O-β - D-葡萄糖苷。
• PREPARATION METHOD AND ANALYTIC METHOD FOR THE EXTRACT OF ANTRODIA CINNAMOMEA
  申请人：WU YANG-CHANG

  公开号：US20160318972A1

  公开（公告）日：2016-11-03

  An optimal preparation and analytic method for the extraction of Antrodia cinnamomea is disclosed. The important parameters for the extraction efficiency of the extract are analyzed using mathematic and statistical experimental designs, and the extract of A. cinnamomea and its particular triterpenoid compounds are quantified and identified using the quantitative NMR and HPLC-tandem MS. Whether the ergostane and lanostane triterpenoid compounds are contained in one drug, health food or other products and the total amounts and individual amounts therein can be analyzed, determined or quantified using the techniques disclosed herein.
• METHODS OF INDUCING OR ENHANCING FARNESOID X RECEPTOR (FXR)-MEDIATED TRANSCRIPTIONAL RESPONSE
  申请人：YALE UNIVERSITY

  公开号：US20220409631A1

  公开（公告）日：2022-12-29

  The disclosure provides a method of treating disease or disorder in a subject in need thereof by administering a therapeutically effective amount of an extract comprising at least one selective Farnesoid X receptor (FXR) agonist obtained from Antrodia cinnamomea ( Antrodia camphorate ) to the subject. The disease or the disorder includes liver disease, obesity, diabetes, diarrhea, abdominal pain, hypertension, itchy skin, liver cancer, hepatitis, biliary cholangitis, nonalcoholic steatohepatitis, primary sclerosing cholangitis, inflammation, and fibrosis.