花薑酮 | 471-05-6

• 物质功能分类: 有机原料 - 酮类化合物
• 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: 花薑酮
• 中文别名: 花姜酮；花?酮
• 英文名称: zerumbone
• 英文别名: (2E,6E,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one；(2E,6E,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-trienone；ZER
• CAS: 471-05-6
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: GIHNTRQPEMKFKO-SKTNYSRSSA-N

物化性质

• 熔点：
  67-69℃
• 沸点：
  321.6±42.0 °C(Predicted)
• 密度：
  0.887±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：≥10mg/mL
• LogP：
  4.168 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性方面，从Zingiber zerumbet Smith 的根茎中分离出的单环倍半萜烯化合物Zerumbone，能有效抑制Epstein-Barr 病毒的激活，其IC50 值为0.14 mM。此外，Zerumbone 还展现出抗癌、抗氧化、抗炎和抗增殖的作用。

反应信息

• 作为反应物：
  描述：

  花薑酮 在 溴 、 氢氧化钾 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Unprecedented olefin-dependent histidine–kinase inhibitory of zerumbone ring-opening material

  摘要：

  Zerumbone ring-opening derivative, 4 (l0E/10Z= 3/2), inhibited autophosphorylation of the essential histidine-kinase YycG existing in Bacillus subtilis constituting a two-component system (TCS). Generation of 4E-form could be regulated chemically using the difference from the ring-opening reactivity of the precursor forming of 4 and pure 4E was isolated. The stereoisomer, 4E, showed main inhibition activity of autophosphorylation of YycG (IC50 = 63.5 muM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.071
• 作为产物：
  描述：

  zerumbol 在 manganese(IV) oxide 作用下， 以80%的产率得到花薑酮
  参考文献：
  名称：

  CONVERSION OF HUMULENE TO ZERUMBONE

  摘要：

  葎草烯首先通过一系列化学反应转化为泽兰酮。

  DOI：

  10.1246/cl.1981.717

文献信息

• Anticancer Activity of the Bioreductive and Non-Bioreductive Zerumbone Derivatives
  作者：Siripit Pitchuanchom、Uraiwan Songsiang、Natthida Weerapreeyakul、Chavi Yenjai

  DOI：10.2174/157018011795906811

  日期：2011.7.1

  Zerumbonoquinone 10 and zerumbonaminone 11 have been designed to release toxic moieties selectively and preferentially under reductive conditions. These compounds were synthesized by coupling the quinone delivery system with zerumbone alcohol 8 and amine 9. All compounds were evaluated for cytotoxicity against KB (non reductase overexpressing cells), NCI-H187 and MCF-7 (reductase overexpressing cells) and normal cells (Vero cells). Bioreductive compounds 10 and 11 were found to act as bioreductive anticancer agents exhibiting less cytotoxicity than the parents 8 and 9 in KB cells with good stability, and were partially bioreductively active against MCF-7 and NCI-H187 cells.

  零姆伯诺醌10和零姆伯胺醌11已被设计在还原条件下选择性和优先释放有毒基团。这些化合物是通过将醌传递系统与零姆酮醇8和胺9结合合成的。所有化合物都针对KB（非还原酶过表达细胞）、NCI-H187和MCF-7（还原酶过表达细胞）以及正常细胞（Vero细胞）进行了细胞毒性评估。生化还原化合物10和11被发现是生化还原抗癌剂，与它们的母体化合物8和9相比，在KB细胞中表现出较少的细胞毒性，并且稳定性良好，对MCF-7和NCI-H187细胞有一定的生化还原活性。
• Metal-Free <i>trans</i> -Aziridination of Zerumbone: Synthesis and Biological Evaluation of Aziridine Derivatives of Zerumbone
  作者：Greeshma Gopalan、Bhandara Purayil Dhanya、Jayaram Saranya、Thankappan Remadevi Reshmitha、Thekke Veettil Baiju、Murugan Thulasi Meenu、Mangalam S. Nair、Prakasan Nisha、Kokkuvayil Vasu Radhakrishnan

  DOI：10.1002/ejoc.201700410

  日期：2017.6.8

  Herein, we describe a metal-free, iodosobenzene diacetate mediated trans-aziridination of zerumbone by the direct use of sulfonamides. Preliminary in vitro screening showed that the synthesized compounds had better antiproliferative and antidiabetic activities than the parent compound zerumbone.

  在本文中，我们描述了通过直接使用磺酰胺，由金属制成的无金属碘代苯二乙酸酯介导的泽隆骨的反式叠氮化。初步的体外筛选显示，合成的化合物具有比母体化合物蛇骨酮更好的抗增殖和抗糖尿病活性。
• Locomotor-Reducing Effects and Structural Characteristics of Inhaled Zerumbone and Tetrahydrozerumbone Derivatives
  作者：Kakuyou Ogawa、Takashi Miyoshi、Takashi Kitayama、Michiho Ito

  DOI：10.1248/bpb.b14-00314

  日期：——

  Zerumbone 1 is an 11-membered cyclic sesquiterpene obtained from the rhizomes of Zingiber zerumbet SMITH (Zingiberaceae). In this study, we investigated the structure–activity relationship of 1, α-humulene (2), tetrahydrozerumbone stereoisomers (3–5), and tetrahydrozerumbone derivatives (6–9). The oxygen-containing functional groups and the configurations at C1 and C2 contributed to the spontaneous locomotor activity reduction of zerumbone 1 and derivatives 2–9.

  台湾产中药材之泽泻泽姜黄(Zingiber zerumbet SMITH, Zingiberaceae)之根茎中含有一种11员环倍半萜烯化合物泽泻泽姜酮1。在本研究中，我们探讨了泽泻泽姜酮1、α-长蒎烯(2)、四氢泽泻泽姜酮立体异构体(3-5)以及四氢泽泻泽姜酮衍生物(6-9)的结构-活性关系。含氧官能团以及C1和C2的构型对泽泻泽姜酮1及其衍生物2-9的自发性运动活性降低有贡献。
• The chemistry of zerumbone. Part 5: Structural transformation of the dimethylamine derivatives
  作者：Takashi Kitayama、Taketo Yokoi、Yasushi Kawai、Richard K Hill、Masanori Morita、Tadashi Okamoto、Yukio Yamamoto、Valery V Fokin、K.Barry Sharpless、Seiji Sawada

  DOI：10.1016/s0040-4020(03)00667-7

  日期：2003.6

  Zerumbone (1) and its 6,7-epoxide (2) react with ammonia and dimethylamine regio- and stereospecifically, affording monoamines 3, 4, 7 and 8. All adducts have the same relative configuration at C2 and C3. The conjugate amination is thermodynamically controlled to arrive at a single diastereomer. At 15°C 7 reacts with cyanide to give aminonitrile 10 as the single product, while at 30°C, acyclic aminonitrile

  球姜酮（1）和它的6,7-环氧化物（2）与氨反应和二甲胺区域选择性和立体有择性，得到一元胺3，4，7和8。所有加合物在C2和C3处具有相同的相对构型。热力学控制共轭胺，以达到单个非对映异构体。在15℃下，7与氰化物反应得到氨基腈10，为单一产物，而在30℃下，也形成无环氨基腈11。与8的反应在0°C时提供双环氨基腈12在30℃或更高的温度下，获得了十二烷骨架的混合物，获得了12与三环腈13和13 '的混合物。的回流7，8和10在乙腈水溶液中促进通过后曼尼希反应的球姜酮环，以提供无环醛的断裂16 - 18分别。的二甲基氨基7，8和10是由Cope-和碱催化立体有择地抵销消除再生球姜酮骨架中的产品1，2和21。应付12的消除反应是通过脱氨基环过环醚化反应生成13和13 '的混合物。
• Accessing Polycyclic Terpenoids from Zerumbone via Lewis Acid Catalyzed Synthetic Strategies
  作者：Puthiyaparambath Sharathna、Murugan Thulasi Meenu、Kokkuvayil Vasu Radhakrishnan、Bhandara Purayil Dhanya、Greeshma Gopalan、Parameswaran Sasikumar、Radhakrishnan Syam Krishnan

  DOI：10.1055/s-0039-1690840

  日期：2020.7

  We herein disclose an effective strategy for the synthesis of [5.3.0] and [6.3.0] fused polycyclic terpenoids, which are important structural elements of natural products and biologically active compounds. The method comprises of Lewis acid catalyzed interrupted Nazarov cyclization of zerumbone derivatives such as zerumbone epoxide, triazole-appended zerumbone, zerumbal, and zerumbenone with a wide

  我们在此公开了一种合成[5.3.0]和[6.3.0]稠合多环萜类化合物的有效策略，它们是天然产物和生物活性化合物的重要结构要素。该方法包括路易斯酸催化的泽鲁姆伯衍生物如泽鲁姆伯环氧化物，三唑附加的泽鲁姆伯酮，泽鲁姆伯和泽鲁贝酮的间断纳扎罗夫环化的中断，具有广泛的吲哚范围。Zerrumbone环氧化合物提供[5.3.0]和[6.3.0]融合的结构多样的倍半萜，所有其他zerumbone衍生物均提供[6.3.0]融合的图案。

表征谱图