lantabetulic acid | 59157-84-5

• 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: lantabetulic acid
• 英文别名: Benulin；(1S,2S,5R,6R,7R,10S,13R,14R,17R,19S)-19-hydroxy-13,14,18,18-tetramethyl-7-prop-1-en-2-yl-20-oxahexacyclo[17.2.2.01,17.02,14.05,13.06,10]tricosane-10-carboxylic acid
• CAS: 59157-84-5
• 化学式: C₃₀H₄₆O₄
• 分子量: 470.693
• InChiKey: KYHMRXXFJAZYRF-MSBRYPFUSA-N

物化性质

• 熔点：
  252-254 °C
• 沸点：
  579.1±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  lantabetulic acid 在 吡啶 、 氢氧化钾 、 一水合肼 作用下， 以 乙二醇 为溶剂， 反应 2.0h， 生成 10-Hydroxymethyl-3-deoxybenulin
  参考文献：
  名称：

  苯酚的结构，一种新的五环三萜半水半胱氨酸，其分离自蒲桃（Burseraae）。

  摘要：

  DOI：

  10.1021/jo00429a033

文献信息

• Lantabetulic Acid Derivatives Induce G1 Arrest and Apoptosis in Human Prostate Cancer Cells
  作者：Kai-Wei Lin、Zih-You Lin、A-Mei Huang、Jing-Ru Weng、Ming-Hong Yen、Shyh-Chyun Yang、Chun-Nan Lin

  DOI：10.1002/ardp.201300224

  日期：2014.1

  Ten new lantabetulic acid (1) derivatives 2–11 were synthesized and their cytotoxicities against human prostate cancer cells were evaluated. PC3 cells treated with 10 μM 8 exhibited the most potent G1 phase arrest. In addition, 10 μM 8 markedly decreased the levels of cyclin E and cdk2 and caused an increase in the p21 and p27 levels, while 20 μM 8 mainly led to cell death through the apoptotic pathway

  合成了 10 种新的羊毛脂酸 (1) 衍生物 2-11，并评估了它们对人前列腺癌细胞的细胞毒性。用 10 μM 8 处理的 PC3 细胞表现出最有效的 G1 期阻滞。此外，10 μM 8 显着降低细胞周期蛋白 E 和 cdk2 的水平并导致 p21 和 p27 水平升高，而 20 μM 8 主要通过凋亡途径导致细胞死亡，这与活性氧水平的增加相关, 降低 Bcl-2 和 caspase-8 的表达水平，诱导线粒体变化，降低线粒体中细胞色素 c 的水平。8的双重作用可为化疗药物的开发提供新途径。
• RHUS VERNICIFLUA STOKES EXTRACT HAVING INCREASED CONTENT OF ACTIVE FLAVONOID COMPOUND AND METHOD FOR PREPARING SAME
  申请人：AZI Company Ltd.

  公开号：EP2604274B1

  公开（公告）日：2016-07-13
• Sweet Gum Fruit Extract as a Therapeutic Agent
  申请人：Liu Zhijun

  公开号：US20100189830A1

  公开（公告）日：2010-07-29

  Sweet gum ( Liquidambar styraciflua L., family Hamamelidaceae) fruit extract was discovered to possess potent activities against multiple targets of the PBK (phosphatidylinositide 3-kinase) pathway, especially the PI3K/Akt and mTOR pathways. At a very low concentration of 1.85 μg/ml (IC50), sweet gun extract showed the ability of simultaneously blocking the pathways of PI3K/Akt (upstream), mTOR (mammalian target of rapamycin) (downstream), as well as its downstream protein products S6K and S6. It was also able to block 5-HETE, a lipoxygenase product that contributes to inflammation and activation of PI3K/Akt. The sweet gum fruit extract was prepared with 50% methanol (47:1; raw to extract) and concentrated to an organic fraction (210:1 raw to extract) referred as LIS-100 via reverse-phase column chromatography using a bioassay directed fractionation approach. The extract is a new targeted therapeutic agent for numerous disorders known to be treated by mTOR inhibitors, including cancer, diabetes, obesity, and inflammation.
• Rhus Verniciflua Stokes Extract Having Increased Content Of Active Flavonoid Compound And Method For Preparing Same
  申请人：Park Sang-Jae

  公开号：US20120283322A1

  公开（公告）日：2012-11-08

  The present invention relates to Rhus verniciflua Stokes extract having an increased content of an active flavonoid compound through a gas bubbling treatment, a method for preparing the Rhus verniciflua Stokes extract, and a method for converting fustin into fisetin through the gas bubbling treatment of a solution containing fustin. The method for preparing the Rhus verniciflua Stokes extract of the present invention can convert the conventional Rhus verniciflua Stokes extract having high content of fustin and low content of fisetin into a Rhus verniciflua Stokes extract having high content of fisetin. Therefore, the Rhus verniciflua Stokes extract of the present invention can be commercialized into natural anticancer agents, anticancer and cancer prevention food products, and health functional foods due to the excellent bioactivity thereof, and promote the development of relevant industries through the high added-value of Rhus verniciflua Stokes. In addition, the method for converting fustin into fisetin can be applied to other natural substances and be used as a method for enhancing the functionality thereof by increasing the content of a high active flavonoid, thereby becoming an enabling technology that can lead high-functionalization of natural substances.
• Method of Converting Fustin to Fisetin
  申请人：AZI COMPANY LTD.

  公开号：US20140031567A1

  公开（公告）日：2014-01-30

  The present invention relates to a method for converting fustin into fisetin through the gas bubbling treatment of a solution containing fustin. Rhus verniciflua Stokes extracts having high content of Fisetin may be used as anticancer agents, anticancer and cancer prevention food products, and health functional foods due to the excellent bioactivity thereof.