kamebakaurin A | 73981-34-7

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 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
• 英文名称: kamebakaurin A
• 英文别名: kamebakaurin；(1R,2R,4R,8S,9R,10S,13S,16R)-2,8,16-trihydroxy-9-(hydroxymethyl)-5,5-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecan-15-one
• CAS: 73981-34-7
• 化学式: C₂₀H₃₀O₅
• 分子量: 350.455
• InChiKey: WHSUEVLJUHPROF-BIGDWJEQSA-N

物化性质

• 熔点：
  232-234℃
• 密度：
  1.30±0.1 g/cm3 (20 ºC 760 Torr)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

制备方法与用途

生物活性方面，kamebakaurin是从日本紫珠（Isodon japonicus）中提取的天然产物。研究显示，kamebakaurin能够抑制NF-κB活性，具体表现为抑制p50的DNA结合能力。

反应信息

• 作为反应物：
  描述：

  kamebakaurin A 在 platinum(IV) oxide 氢气 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (1R,2R,6R,8R,12S,13R,14S,17S,18R)-12-hydroxy-13-(hydroxymethyl)-4,4,9,9,18-pentamethyl-3,5-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadecan-19-one
  参考文献：
  名称：

  Takeda, Yoshio; Ichihara, Teruyoshi; Takaishi, Yoshihisa, Journal of the Chemical Society. Perkin transactions I, 1987, p. 2403 - 2410

  摘要：

  DOI：
• 作为产物：
  描述：

  、 、 、 Kamebacetal A 、 在 silica gel 作用下， 以 ethyl acetate n-hexane 为溶剂， 以was isolated from the 3-B fraction, and kamebakaurin的产率得到kamebakaurin A
  参考文献：
  名称：

  Use of diterpene compound as a therapeutic agent of inflammation, immune disease or cancer

  摘要：

  本公开涉及二萜化合物作为炎症、免疫性疾病或癌症治疗剂的新用途。更具体地，本发明涉及二萜化合物的新用途，包括卡美巴宁、卡美巴醛A、卡美巴熊果酮和艾克西桑宁A，通过抑制NF-kB活性，抑制一氧化氮、前列腺素和TNF-a1的产生，对治疗炎症、免疫性疾病或癌症有效。

  公开号：

  US06894073B2

文献信息

• Efficient synthesis of novel cytotoxic cis-fused α-methylene γ-lactones from 7,14-dihydroxy-ent-kaurenes by transformation under Mitsunobu reaction conditions
  作者：Yutaka Aoyagi、Ming-Yu Gui、Yong-Ri Jin、Xu-Wen Li、Takeshi Noguchi、Haruhiko Fukaya、Tomoyo Hasuda、Koichi Takeya

  DOI：10.1016/j.tetlet.2003.12.041

  日期：2004.2

  14-dihydroxy-ent-kaurenes such as excisanin A (8), kamebanin (9), and kamebakaurin (10), which are abundant in plants of the genus Rabdosia species (Labiatae), to ent-abietanes was accomplished under the Mitsunobu reaction conditions. The δ, ε-unsaturated cis-fused α-methylene γ-lactones (17, 18, and 25) thus prepared showed a moderate cytotoxic activity on P388 murine leukemia cells.

  的7,14二羟基容易转化ENT -kaurenes如excisanin A（8），kamebanin（9），和kamebakaurin（10），这是在丰富属植物香茶菜物种（唇形科），以ENT -abietanes是在Mitsunobu反应条件下完成。的δ，ε -不饱和顺-融合α亚甲基γ内酯（17，18，和25）如此制备显示对P388鼠白血病细胞温和的细胞毒性活性。
• Excisanin H, a Novel Cytotoxic 14,20-Epoxy-<i>ent</i>-Kaurene Diterpenoid, and Three New <i>e</i><i>nt</i>-Kaurene Diterpenoids from <i>Rabdosia</i> <i>e</i><i>xcisa</i>
  作者：Ming-yu Gui、Yutaka Aoyagi、Yong-Ri Jin、Xu-Wen Li、Tomoyo Hasuda、Koichi Takeya

  DOI：10.1021/np030357r

  日期：2004.3.1

  A novel 14,20-epoxy-ent-kaurene diterpenoid, excisanin H (1), and three new ent-kaurene diterpenoids, 2-4, were isolated from aerial parts of Rabdosia excisa along with eight known ent-kaurene diterpenoids, 5-12. The structural elucidations were made using spectral (HREIMS, IR, (1)H, (13)C, and 2D NMR) methods. The absolute configuration of 1 was determined by demonstrating that oxidation of kamebakaurin

  从Rabdosia excisa的地上部分中分离出一种新型的14,20-环氧-ent-月桂烯二萜类化合物exisanin H（1）和三个新的ent-月桂烯二萜类化合物2-4，以及8种已知的ent-月桂烯二萜类化合物5- 12 使用光谱（HREIMS，IR，（1）H，（13）C和2D NMR）方法进行结构阐明。1的绝对构型通过证明kamebakaurin（8）的氧化产生了exisanin H（1）来确定。这些ENT-月桂烯二萜类化合物均对P388鼠白血病细胞显示出显着的细胞毒活性。
• Novel use of diterpene compound as a therapeutic agent of inflammation, immune disease or cancer
  申请人：——

  公开号：US20040048918A1

  公开（公告）日：2004-03-11

  The disclosure concerns novel use of diterpene compound as a therapeutic agent of inlfammation, immune disease or cancer. More particularly, the present invention relates to novel use of diterpene compound that include kamebanin, kamebacetal A, kamebakaurin, and exisanin A, which would be effective for the treatnent inflammation, immune disease or cancer by inhibiting the production of nitric oxide, prostaglandin, and TNF- a , through the suppression of NF- k B activity.

  本公开涉及二萜化合物作为治疗炎症、免疫疾病或癌症的治疗剂的新用途。更具体地说，本发明涉及二萜化合物的新用途，包括卡美巴宁、卡美巴醛A、卡美巴酮和埃克西桑醇A，通过抑制NF-kB活性，抑制一氧化氮、前列腺素和TNF-a的产生，对治疗炎症、免疫疾病或癌症有效。
• Efficient transformation of 7,14-dihydroxy-ent-kaurenes to novel ent-abietanes having cis-fused α-methylene γ-lactones under Mitsunobu reaction conditions and their cytotoxicities
  作者：Yutaka Aoyagi、Kei Ozawa、Tatsuya Kobayashi、Tomoyo Hasuda、Ming-Yu Gui、Yong-Ri Jin、Xu-Wen Li、Haruhiko Fukaya、Reiko Yano、Yukio Hitotsuyanagi、Koichi Takeya

  DOI：10.1016/j.tet.2014.02.082

  日期：2014.5

  Transformation of plant-origin 7,14-dihydroxy-ent-kaurenes to ent-abietanes having a cis-fused alpha-methylene gamma-lactones was accomplished efficiently under the Mitsunobu reaction conditions. The yields of the desired products were apparently influenced by the steric hindrance at C-1. The cytotoxic activity on P388 murine leukemia cells of the ent-abietanes having cis-fused alpha-methylene gamma-lactones produced were assayed. (C) 2014 Elsevier Ltd. All rights reserved.
• TAKEDA, YOSHIO;ICHIHARA, TERUYOSHI;TAKAISHI, YOSHIHISA;FUJITA, TETSURO;SH+, J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 11, 2403-2409
  作者：TAKEDA, YOSHIO、ICHIHARA, TERUYOSHI、TAKAISHI, YOSHIHISA、FUJITA, TETSURO、SH+

  DOI：——

  日期：——