3α,25-dihydroxyolean-12-en-28-oic acid | 710306-91-5

• 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: 3α,25-dihydroxyolean-12-en-28-oic acid
• 英文别名: (4aS,6aS,6aS,6bR,8aR,10R,12aS,14bS)-10-hydroxy-12a-(hydroxymethyl)-2,2,6a,6b,9,9-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 710306-91-5
• 化学式: C₃₀H₄₈O₄
• 分子量: 472.709
• InChiKey: ZVNHGZQUXCHNLK-JDBAKTTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3α,25-dihydroxyolean-12-en-28-oic acid 在 吡啶 作用下， 以 甲醇 、 苯 为溶剂， 反应 5.0h， 生成 methyl 3α,25-diacetoxyolean-12-en-28-oate
  参考文献：
  名称：

  New Cytotoxic Oleanane-Type Triterpenoids from the Cones of Liquidamber styraciflua

  摘要：

  Two new oleanane-type triterpenoids (1 and 2), together with two known compounds, 6beta-hydroxy-3-oxo-lup-20(29)-en-28-oic acid (3) and 3,11-dioxoolean-12-en-28-oic acid (4), were isolated from the stem bark of Liquidamber styraciflua. The structures of 1 and 2 were determined to be 25-acetoxy-3alpha-hydroxyolean-12-en-28-oic acid (1) and 3alpha,25-dihydroxyolean-12-en-28-oic acid (2) on the basis of spectroscopic methods and chemical conversion. Compound 1 showed strong cytotoxicity against a disease-oriented panel of 39 human cancer cell lines, although compounds 2, 3, and 4 showed weaker activity compared to 1.

  DOI：

  10.1021/np0305369
• 作为产物：
  描述：

  25-acetoxy-3α-hydroxyolean-12-en-28-oic acid 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以18.3 mg的产率得到3α,25-dihydroxyolean-12-en-28-oic acid
  参考文献：
  名称：

  New Cytotoxic Oleanane-Type Triterpenoids from the Cones of Liquidamber styraciflua

  摘要：

  Two new oleanane-type triterpenoids (1 and 2), together with two known compounds, 6beta-hydroxy-3-oxo-lup-20(29)-en-28-oic acid (3) and 3,11-dioxoolean-12-en-28-oic acid (4), were isolated from the stem bark of Liquidamber styraciflua. The structures of 1 and 2 were determined to be 25-acetoxy-3alpha-hydroxyolean-12-en-28-oic acid (1) and 3alpha,25-dihydroxyolean-12-en-28-oic acid (2) on the basis of spectroscopic methods and chemical conversion. Compound 1 showed strong cytotoxicity against a disease-oriented panel of 39 human cancer cell lines, although compounds 2, 3, and 4 showed weaker activity compared to 1.

  DOI：

  10.1021/np0305369

文献信息

• Oleanane Triterpenoids with Inhibitory Activity against NFAT Transcription Factor from Liquidambar formosana
  作者：Nguyen Tien Dat、Im Seon Lee、Xing Fu Cai、Guanghai Shen、Young Ho Kim

  DOI：10.1248/bpb.27.426

  日期：——

  In a search for inhibitory components from natural products against NFAT transcription factor, this study investigated the ethyl acetate extract of the fruits of Liquidambar formosana. Four oleanane triterpenoids were isolated and identified to be liquidambaric acid, oleanolic acid, 3α-acetoxy-25-hydroxy-olean-12-en-28-oic acid and lantanolic acid. Of these compounds, 3α-acetoxy-25-hydroxy-olean-12-en-28-oic acid (IC50: 4.63 μM) and lantanolic acid (IC50: 12.62 μM) exhibited strong inhibitory activity against the NFAT transcription factor.

  为了从天然产品中寻找对 NFAT 转录因子的抑制成分，本研究对枫香树果实的乙酸乙酯提取物进行了研究。研究分离并鉴定出四种齐墩果烷三萜类化合物，分别是液甘草酸、齐墩果酸、3α-乙酰氧基-25-羟基-油菜-12-烯-28-酸和香叶醇酸。在这些化合物中，3α-乙酰氧基-25-羟基-油烷-12-烯-28-酸（IC50：4.63 μ<小>M）和香丹酚酸（IC50：12.62 μ<小>M）对 NFAT 转录因子具有很强的抑制活性。
• 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.
• [EN] SWEET GUM FRUIT EXTRACT AS A THERAPEUTIC AGENT<br/>[FR] EXTRAIT DE FRUIT DE LIQUIDAMBAR UTILISE COMME AGENT THERAPEUTIQUE
  申请人：UNIV LOUISIANA STATE

  公开号：WO2008144706A2

  公开（公告）日：2008-11-27

  [EN] 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.
  [FR] Selon l'invention, il a été établi qu'un extrait de fruit de liquidambar (Liquidambar styraciflua L., famille des hamamélidacées) présentait une activité puissante contre des cibles multiples de la voie PBK (phosphatidylinositide 3-kinase), en particulier les voies PI3K/Akt et mTOR. À une très faible concentration de 1,85 µg/ml (IC50), l'extrait de liquidambar présente la propriété de bloquer simultanément les voies de PI3K/Akt (amont), mTOR (cible mammifère de rapamycine) (aval), ainsi que ses produits protéiniques aval S6K et S6. Ledit extrait est également apte à bloquer 5-HETE, un produit de lipoxygénase qui contribue à l'inflammation et à l'activation de PI3K/Akt. L'extrait de fruit de liquidambar selon l'invention a été obtenu avec 50% de méthanol (47: 1; état brut-extrait) et concentré en une fraction organique (210: 1 état brut-extrait) appelée LIS-100 par chromatographie sur colonne en phases inversées, par la mise en oevre d'une approche de fractionnement dirigée par dosage biologique. L'extrait selon l'invention est un nouvel agent thérapeutique ciblé destiné à de nombreux troubles connus pour être sensibles à un traitement par inhibiteurs de mTOR, notamment le cancer, le diabète, l'obésité et les inflammations.