12-O-甲基鼠尾草酸 | 62201-71-2

• 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
• 中文名称: 12-O-甲基鼠尾草酸
• 英文名称: 12-O-methylcarnosic acid
• 英文别名: 12-methoxycarnosic acid；12-methoxy-trans-carnosic acid；carnosic acid 12-methyl ether；(4aR,10aS)-5-hydroxy-6-methoxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid
• CAS: 62201-71-2
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: QQNSARJGBPMQDI-YCRPNKLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  12-O-甲基鼠尾草酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以81%的产率得到carnosic acid 12-methyl ether γ-lactone
  参考文献：
  名称：

  Gastroprotective Effect of Carnosic Acid γ-Lactone Derivatives

  摘要：

  Carnosic acid (1) has been shown to possess gastroprotective activity in vitro and in vivo. However, little is known of the gastroprotective effect or cytotoxicity of carnosic acid gamma-lactone (3). To determine structure activity relationships, a series of 17 esters of 3 were prepared including aliphatic, aromatic, and heterocyclic derivatives. Also, two units of 3 were coupled with succinic and phthalic acid as linkers. The compounds were assessed for their gastroprotective effect in the HCl/EtOH-induced gastric lesions model in mice and for cytotoxicity in human lung fibroblasts, human adenocarcinoma AGS cells, and Hep G2 hepatocellular carcinoma cells. At a single oral dose of 40 mg/kg, the gastroprotective effect increased moderately with the length of the alkyl chain. The best effects were observed for the butyrate (9) and chloroacetate (6) derivatives. Activity of fatty acid esters increased with chain length but decreased with unsaturation. The best gastroprotective effect, with lowest cytotoxicity, was found for the palmitate (11) and oleate (12) derivatives.

  DOI：

  10.1021/np900822x

文献信息

• Gastroprotective Effect and Cytotoxicity of Carnosic Acid Derivatives
  作者：Cristina Theoduloz、Mariano Pertino、Jaime Rodríguez、Guillermo Schmeda-Hirschmann

  DOI：10.1055/s-0030-1250648

  日期：2011.6

  Carnosic acid (CA) is the main phenolic diterpene of rosemary (Rosmarinus officinalis L., Lamiaceae) and presents gastroprotective effect in vitro and in vivo. To determine structure-activity relationships, seventeen esters and ethers of CA were prepared, comprising aliphatic, aromatic, and heterocyclic compounds. The naturally occurring 12-O-methylcarnosic acid (14) was also included in the study. The compounds were evaluated for their gastroprotective activity in the HCl/EtOH-induced gastric lesions model in mice, and for cytotoxicity in human adenocarcinoma AGS cells, Hep G2 hepatocellular carcinoma cells, and human lung fibroblasts. At 10 mg/kg, some of the CA derivatives (5, 8, 9, 12, 14, and 18) were more effective preventing gastric lesions than the reference compound lansoprazole at the same dose. The dibenzoate 9, diindoleacetate 12, and the derivative 18 showed the best gastroprotective effect combined with the lowest cytotoxicity.

  迷迭香酸（Carnosic acid，CA）是迷迭香（Rosmarinus officinalis L.，唇形科）的主要酚类二萜，在体外和体内具有胃保护作用。为了确定结构-活性关系，研究人员制备了 17 种 CA 的酯类和醚类化合物，包括脂肪族、芳香族和杂环族化合物。研究还包括天然存在的 12-O-甲基卡诺酸（14）。研究评估了这些化合物在 HCl/EtOH 诱导的小鼠胃损伤模型中的胃保护活性，以及在人腺癌 AGS 细胞、Hep G2 肝癌细胞和人肺成纤维细胞中的细胞毒性。在 10 毫克/千克的剂量下，一些 CA 衍生物（5、8、9、12、14 和 18）比相同剂量的参考化合物兰索拉唑更有效地防止胃部病变。二苯甲酸酯 9、二吲哚乙酸酯 12 和衍生物 18 显示出最佳的胃保护效果和最低的细胞毒性。
• Terpenoids from Salvia lanigera
  作者：Hassan M.G.Al-Hazimi、Ghulam A. Miana、M.S.H. Deep

  DOI：10.1016/s0031-9422(00)82356-0

  日期：1987.1

  Abstract Two new terpenoids, 12-methoxycarnosic acid and 3β-hydroxyoleanan-13β → 28 lactone, have been isolated from the leaves of Salvia lanigera , together with two known diterpenes and two triterpenes.

  摘要 从Salvia lanigera 的叶子中分离出两种新的萜类化合物12-甲氧基鼠尾草酸和3β-羟基齐墩果-13β→28 内酯，以及两种已知的二萜和两种三萜。
• The Isolation of Carnosic Acid 12-Methyl Ether from Salvia officinalis L. and NMR Study of Its Methyl Ester
  作者：Zoltan Djarmati、Ratko M. Jankov、János Csanádi、Aleksandar Djordjevic

  DOI：10.1135/cccc19931919

  日期：——

  In continuation of our studies on the chemical compositions of the aerial parts of cultivated Salvia officinalis L., we have isolated the title substance for the first time in this type of Sage. The structure of this isolated compound was established by spectroscopic data and some chemical reactions. Investigation of ¹H and ¹³C NMR, homonuclear (COSY) (¹H-¹H), heteronuclear (HETCOR) (¹H-¹³C), and selective INEPT spectra, permitted the unambiguous assignment of the ¹H and ¹³C NMR spectra, what gave the possibility to resolve signals of similar natural products.

  在我们对栽培鼠尾草（学名：Salvia officinalis L.）的空气部分的化学成分研究中，我们首次从这种鼠尾草中分离出了标题物质。通过光谱数据和一些化学反应，我们确定了这个分离化合物的结构。对¹H和¹³C NMR、同核（COSY）(¹H-¹H)、异核（HETCOR）(¹H-¹³C)和选择性INEPT光谱的研究，使我们能够明确地分配¹H和¹³C NMR光谱，并有可能解决类似天然产物的信号。
• Antiviral Effect of Natural and Semisynthetic Diterpenoids against Adenovirus Infection in vitro
  作者：Juan Esteban Bidart、Mariano Walter Pertino、Guillermo Schmeda-Hirschmann、Laura Edith Alché、Erina Petrera

  DOI：10.1055/a-2058-3635

  日期：2023.8

  highlighted the need to develop new broad-spectrum antivirals to mitigate human infections. Pursuing our search for new bioactive plant-derived molecules, we study several diterpene derivatives synthesized from jatropholones A and B and carnosic acid isolated from Jatropha isabellei and Rosmarinus officinalis, respectively. Here, we investigate the antiviral effect of the diterpenes against human adenovirus

  病毒的出现和重新出现凸显了开发新的广谱抗病毒药物以减轻人类感染的必要性。为了寻找新的生物活性植物衍生分子，我们研究了分别由麻风树酮 A 和 B 以及从麻风树和迷迭香中分离的鼠尾草酸合成的几种二萜衍生物。在这里，我们研究了二萜对人类腺病毒 (HAdV-5) 的抗病毒作用，这种病毒会引起多种感染，但目前还没有批准的抗病毒疗法。对 10 种化合物进行了评估，没有一种化合物在 A549 细胞中表现出细胞毒性。只有化合物2、5和9以浓度依赖性方式抑制HAdV-5复制，没有杀病毒活性，而抗病毒作用发生在病毒内化后。病毒蛋白 E1A 和 Hexon 的表达被化合物 2 和 5 强烈抑制，化合物 9 也受到较小程度的抑制。由于化合物 2、5 和 9 阻止 ERK 激活，它们可能通过干扰宿主细胞来发挥抗病毒作用病毒复制所需的功能。此外，这些化合物还具有抗炎作用，因为它们显着抑制感染 HAdV-5 或腺病毒载体的
• Cytotoxicity of abietane diterpenoids from Perovskia abrotanoides and of their semisynthetic analogues
  作者：Yutaka Aoyagi、Yoshinao Takahashi、Yudai Satake、Koichi Takeya、Ritsuo Aiyama、Takeshi Matsuzaki、Shusuke Hashimoto、Teruo Kurihara

  DOI：10.1016/j.bmc.2006.03.047

  日期：2006.8

  Seven known abietane diterpenoids and 11-O- and 12-O-acetylcarnosic acids were isolated from a methanol extract of Perovskia abrotanoides (Labiatae). Structure and cytotoxic activity relationships (SARs) of the natural and semisynthetic analogues of the presently isolated abietane diterpenoids were studied by using P388 murine leukemia cells. (c) 2006 Elsevier Ltd. All rights reserved.