3β,6β,23- trihydroxyolean-12-en-28-oic acid

• 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: 3β,6β,23- trihydroxyolean-12-en-28-oic acid
• 英文别名: Uncargenin C；(4aS,6aR,6aS,6bR,8R,8aR,9R,10S,12aR,14bS)-8,10-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• 化学式: C₃₀H₄₈O₅
• 分子量: 488.708
• InChiKey: XRRLUGUSXUFEDF-NJMQRACMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  35
• 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：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  12α-bromo-3-oxoolean-28β→13β olide 在 甲醇 、 sodium periodate 、 lithium aluminium tetrahydride 、 锂硼氢 、 四丙基高钌酸铵 、 ruthenium(III) chloride trihydrate 、 盐酸羟胺 、 碘 、 4-甲基苯磺酸吡啶 、 乙酸酐 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 N-甲基吗啉氧化物 、 calcium carbonate 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 aq. phosphate buffer 、 水 、 丙酮 、 乙腈 、 苯 为溶剂， 反应 230.41h， 生成 3β,6β,23- trihydroxyolean-12-en-28-oic acid
  参考文献：
  名称：

  中继CH氧化逻辑在多羟基化的齐墩果三萜类化合物中的应用

  摘要：

  尽管由于不良的溶解度和生物利用度，丰富的原料三萜类化合物如齐墩果酸的临床应用受到限制，但合成获得更高羟基化的齐墩果萜烯类化合物仍然具有挑战性。我们现在报告使用中继CH氧化逻辑来模仿P450单加氧酶在自然界中进行的过程。为此，我们使用C-23-OH作为氢原子转移至C-6的天然手柄，从而实现了高度氧化的天然产物uncargenin C和原碱酸的首次合成，并揭示了其抗白血病活性合成中间体。

  DOI：

  10.1016/j.chempr.2020.04.007

文献信息

• Anti-inflammatory Triterpenoid Saponins from the Stem Bark of <i>Kalopanax pictus</i>
  作者：Tran H. Quang、Nguyen T. T. Ngan、Chau V. Minh、Phan V. Kiem、Nguyen X. Nhiem、Bui H. Tai、Nguyen P. Thao、Nguyen H. Tung、Seok B. Song、Young H. Kim

  DOI：10.1021/np200382s

  日期：2011.9.23

  Five new compounds, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3 beta,6 beta,23-trihydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopyranoside (3), 3-O-[2,3-di-O-acetyl-alpha-L-arabinopyranosyl]hederagenin 28-O-alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranoside (4), and 3-O-[3,4-di-O-acetyl-alpha-L-arabinopyranosyl]hederagenin 28-O-alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranoside (5), as well as 10 known compounds (6-15), were isolated from the stem bark of Kalopanax pictus. Compounds 1-5 and 7-14 inhibited TNF alpha-induced NF-kappa B transcriptional activity in HepG2 cells in a dose-dependent manner, with IC(50) values ranging from 0.6 to 16.4 mu M. Furthermore, the transcriptional inhibitory function of these compounds was confirmed on the basis of decreases in COX-2 and iNOS gene expression in HepG2 cells. The structure activity relationship of the compounds with respect to anti-inflammatory activity is also discussed.
• Cytotoxic triterpene saponins from the stem bark of Kalopanax pictus
  作者：Tran Hong Quang、Nguyen Thi Thanh Ngan、Chau Van Minh、Phan Van Kiem、Hye-Jin Boo、Jin-Won Hyun、Hee-Kyoung Kang、Young Ho Kim

  DOI：10.1016/j.phytol.2011.12.005

  日期：2012.3

  Three new compounds, 3 beta,6 beta,23-trihydroxyolean-12-en-28-oic acid 3-O-alpha-L-arabinopyranoside (1), kalopanaxsaponin L (2), and kalopanaxsaponin M (13), as well as eleven known compounds (3-12 and 14), were isolated from the stem bark of Kalopanax pictus. Their structures were determined on the basis of extentive spectroscopic analyses and acid hydrolysis. The cytotoxicity of the compounds was evaluated in three human carcinoma cell lines, including HL-60, HCT-116, and MCF-7. Compounds 1, 5-8, 10, and 11 exhibited significantly cytotoxic activity toward HL-60 cells, with IC50 values ranging from 0.1 to 6.9 mu M. Compounds 4-7 and 14 showed significant cytotoxicity against HCT-116 cells, with IC50 values ranging from 0.4 to 9.2 mu M. Remarkably, the cytotoxic activities of compounds 5-7 against HCT-116 cells were greater than that of the anticancer chemotherapy drug, mitoxantrone (IC50 = 3.7 mu M). Compounds 1, 3, 5, and 14 were cytotoxic toward MCF-7 cells with IC50 values in a range of 7.4-14.5 mu M. (C) 2011 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
• Application of Relay C−H Oxidation Logic to Polyhydroxylated Oleanane Triterpenoids
  作者：Martin Berger、Christian Knittl-Frank、Sophie Bauer、Georg Winter、Nuno Maulide

  DOI：10.1016/j.chempr.2020.04.007

  日期：2020.5

  Although clinical applications of abundant feedstock triterpenoids such as oleanolic acid are limited because of poor solubility and bioavailability, synthetic access to higher hydroxylated oleanane terpenoids is challenging. We now report the use of relay C−H oxidation logic to mimic the processes carried out in nature by P450 monooxygenase enzymes. To this end, we used the C-23-OH as natural handle

  尽管由于不良的溶解度和生物利用度，丰富的原料三萜类化合物如齐墩果酸的临床应用受到限制，但合成获得更高羟基化的齐墩果萜烯类化合物仍然具有挑战性。我们现在报告使用中继CH氧化逻辑来模仿P450单加氧酶在自然界中进行的过程。为此，我们使用C-23-OH作为氢原子转移至C-6的天然手柄，从而实现了高度氧化的天然产物uncargenin C和原碱酸的首次合成，并揭示了其抗白血病活性合成中间体。