rosmaquinone | 121927-71-7

• 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: rosmaquinone
• 英文别名: (1R,8S,9S,10S)-8-hydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadeca-2(7),5-diene-3,4,15-trione
• CAS: 121927-71-7
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: IQNNDXVLTVLXLJ-FORWCCJISA-N

物化性质

• 熔点：
  167-169 °C
• 沸点：
  575.1±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 储存条件：
  存放在2-8℃的环境中，应保持干燥并密封。

制备方法与用途

罗马奎诺内是一种芳香二萜类化合物，存在于迷迭香属植物中。

反应信息

• 作为反应物：
  描述：

  rosmaquinone 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到
  参考文献：
  名称：

  Cytotoxicity of abietane diterpenoids from Perovskia abrotanoides and of their semisynthetic analogues

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2006.03.047
• 作为产物：
  描述：

  鼠尾草酸 在 氧气 、 碳酸氢钠 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 20.0 ℃ 、10.0 kPa 条件下， 反应 13.0h， 生成 rosmaquinone
  参考文献：
  名称：

  香豆酚及其衍生物的半合成。容易获得从鼠尾草属中分离出来的松香三萜二烯，具有生物活性。

  摘要：

  已知的二萜rosmanol（3），rosmaquinone（4），7-甲氧基rosmanol（5），7-ethoxyrosmanol（6），galdosol（7）和epirosmanol（8）是由鼠李糖酚（2），丹参物种中存在丰富的天然产物。这些半合成二萜的物理和光谱数据与真实的天然样品的数据相同，文献报道的数据也相同。这些松果二萜具有非常有趣的生物学活性，并以少量存在于丹参中。因此，本文所述的半合成方法代表了一种获得这些化合物的有效替代方法。此外，通过与Ph3P / NBS在CH2Cl2中反应，从16-羟基香茅醇（9）获得了已知的二萜16-羟基香豆酚（10）和新的芳族二萜11。

  DOI：

  10.1021/np010565o

文献信息

• Semisynthesis and Biological Evaluation of Abietane-Type Diterpenes. Revision of the Structure of Rosmaquinone
  作者：Joaquín G. Marrero、Laila Moujir、Lucía S. Andrés、Nayely P. Montaño、Liliana Araujo、Javier G. Luis

  DOI：10.1021/np900047p

  日期：2009.8.28

  isorosmaquinone (10) was obtained from isorosmanol (12). The proton resonances of rosmaquinone (11) are reassigned based on 2D NMR spectroscopy. These compounds, as well as eight known analogues, were evaluated for cytotoxic and antimicrobial activities.

  新的芳族二萜7β- ø -benzylrosmanol（3），7β- Ô苄基-11,12-二- Ö -methylrosmanol（4），和7α-thiophenylcarnosic酸（5）已经由从鼠尾草酚部分合成得到的（1），丹参物种中存在丰富的天然二萜。这些化合物的结构是根据其物理和光谱数据确定的。已知的二萜sagequinone甲基化物A（6），7β- Ô -methylrosmanol（7），7- Ô -methylrosmanol（8），和rosmaquinone B（9）来自rosmanol（2）。这些半合成二萜的光谱数据与文献报道的数据相同。另外，新的半合成异松香醌（10）是从异松香醇（12）获得的。根据2D NMR光谱重新分配了rosmaquinone（11）的质子共振。评价了这些化合物以及八种已知的类似物的细胞毒性和抗菌活性。
• Inhibition of squalene synthase of rat liver by abietane diterpenes derivatives
  作者：Mariana Macías-Alonso、Lucía S. Andrés、Iván Córdova-Guerrero、Arturo Estolano-Cobián、Laura Díaz-Rubio、Joaquín G. Marrero

  DOI：10.1080/14786419.2019.1678614

  日期：2021.9.2

  composition of cultivated Salvia canariensis L was determined. Carnosol was the main product isolated. We prepared more lipophilic derivatives from carnosol, and both isolated and semisynthetic abietane diterpenes were evaluated in vitro as inhibitors of squalene synthase. Among the compounds tested, carnosol was the most potent inhibitor (IC50 = 17.6 μM). These results highlight the great potential of

  摘要 在目前的研究中，确定了栽培的加那利鼠尾草的化学成分。鼠尾草酚是分离的主要产品。我们从鼠尾草酚中制备了更多的亲脂性衍生物，并在体外评估了分离的和半合成的松香烷二萜作为角鲨烯合酶的抑制剂。在测试的化合物中，鼠尾草酚是最有效的抑制剂 (IC 50 = 17.6 μM)。这些结果突出了该物种在生产用于治疗高脂血症的营养补充剂中的新成分方面的巨大潜力。
• Abietane diterpenes with antibiotic activity from the flowers of <i>Salvia</i><i>canariensis</i>. Reaction of galdosol with diazomethane
  作者：Antonio G. González、Lucia S. Andrés、Juan R. Herrera、Javier G. Luis、Angel G. Ravelo

  DOI：10.1139/v89-035

  日期：1989.2.1

  The new diterpenes canariquinone (9), rosmaquinone (10), and 11-acetoxycarnosic acid (6), together with the already known 7-ethoxyrosmanol (1), 7-methoxyrosmanol (2), and rosmanol (3), were isolated from the flowers of Salviacanariensis. The structure of the new substances was established by a combination of chemical and spectroscopic means. Reaction of galdosol (4), isolated from the aerial part of the same plant, with diazomethane, unexpectedly gave the new homoditerpenes 15 and 16, the structures of which were determined by spectroscopic methods. A mechanism accounting for the formation of these substances is suggested. Keywords: abietane diterpenes, Salvia, Labiatae, antibiotic activity, galdosol reactivity.

  新的二萜类化合物canariquinone (9)，rosmaquinone (10)，以及11-acetoxycarnosic acid (6)，连同已知的7-ethoxyrosmanol (1)，7-methoxyrosmanol (2)，和rosmanol (3)，从Canary Sage的花中分离出来。新物质的结构通过化学和光谱手段相结合确定。从同一植物的地上部分分离出来的galdosol (4)与重氮甲烷反应，意外地产生了新的同源二萜类化合物15和16，其结构通过光谱方法确定。提出了一种解释这些物质形成的机制。关键词：亚松烷二萜类化合物，鼠尾草，唇形科，抗生素活性，galdosol反应性。
• Recovery of Antioxidant Activity from Carnosol Quinone:  Antioxidants Obtained from a Water-Promoted Conversion of Carnosol Quinone
  作者：Toshiya Masuda、Takuya Kirikihira、Yoshio Takeda

  DOI：10.1021/jf050685s

  日期：2005.8.1

  Carnosol is one of the main antioxidants in sage and rosemary. Although carnosol quinone is the antioxidation product of carnosol and has a very weak antioxidant activity, its treatment in water-containing solvent restored its strong antioxidant activity. HPLC analysis of the water-stimulated recovery reaction of the antioxidant activity revealed that the strong activity was due to the reproduced camosol. The analysis also showed that an almost equal amount of quinone derivatives of rosmanol (rosmanol quinone) was produced in the reaction along with the camosol. The rosmanol was formed by the addition of 1 equiv of water and the following isomerization from camosol quinone in the water-containing solvent. The formed rosmanol was also found to be oxidized by the remaining camosol quinone to produce rosmanol quinone. At the same time, camosol quinone was reduced to afford camosol. This redox phenomenon is an important part of the mechanism for the recovery of the antioxidant activity from camosol quinone under the water-containing conditions.
• ROSEMARY/PHOSPHOLIPASE COMPOSITIONS AND METHODS OF PRESERVING MUSCLE TISSUE
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20210329932A1

  公开（公告）日：2021-10-28

  The disclosure provides for compositions and methods for the preservation of meat tissues, including fish, beef, poultry and pork, and meat analogs containing added heme protein, using very low amounts of phospholipase A2 (PLA2) enzymes in a combination with rosemary.