灵芝马酮 | 106518-63-2

• 物质功能分类: 天然产物 - 萜类
• 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: 灵芝马酮
• 英文名称: ganodermanontriol
• 英文别名: (5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-[(2R,5S,6R)-5,6,7-trihydroxy-6-methylheptan-2-yl]-1,2,5,6,12,15,16,17-octahydrocyclopenta[a]phenanthren-3-one
• CAS: 106518-63-2
• 化学式: C₃₀H₄₈O₄
• 分子量: 472.709
• InChiKey: KASALCUNLBTNAA-LIPCCPSCSA-N

物化性质

• 溶解度：
  氯仿：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

制备方法与用途

生物活性

Ganodermanontriol 是从灵芝（Ganoderma lucidum）中提取的一种甾醇，能够通过诱导HO-1的表达来发挥抗炎作用，并保护受损肝细胞免受t-BHP损伤。此外，Ganodermanontriol 还具有保肝作用。

体外研究

在体外实验中，Ganodermanontriol 对乳腺癌细胞系MCF-7和MDA-MB-231表现出抑制作用，其半数抑制浓度（IC₅₀）分别为5.8 μM和9.7 μM。

反应信息

• 作为反应物：
  描述：

  灵芝马酮 、 ganoweberianic acid A 在 4-二甲氨基吡啶 、 1,2-二氯乙烷 作用下， 以 二氯甲烷 为溶剂， 生成 Ganoweberianone A
  参考文献：
  名称：

  Antimalarial Lanostane Dimers from Artificially Cultivated Fruiting Bodies of Ganoderma weberianum

  摘要：

  DOI：

  10.1021/acs.jnatprod.3c00457
• 作为产物：
  描述：

  (5R,10S,13R,14R,17R)-17-((R,Z)-7-hydroxy-6-methylhept-5-en-2-yl)-4,4,10,13,14-pentamethyl-4,5,6,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one 在 甲基磺酰胺 、 AD-mix β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 6.0h， 以76%的产率得到灵芝马酮
  参考文献：
  名称：

  Process for preparing delta-7,9(11) steroids from Ganoderma lucidum and analogs thereof

  摘要：

  描述了从药用蘑菇灵芝中制备鲁氏萜类化合物的过程，以及相关化合物。还描述了用于治疗癌症的化合物、组合物和方法。

  公开号：

  US09376462B2

文献信息

• Semisynthesis and Biological Evaluation of Ganodermanontriol and Its Stereoisomeric Triols
  作者：Erin M. Kennedy、Steven J. P’Pool、Jiahua Jiang、Daniel Sliva、Robert E. Minto

  DOI：10.1021/np200205n

  日期：2011.11.28

  The first synthesis of ganodermanontriol, a bioactive lanostane triterpene from the medicinal mushroom Ganoderma lucidum, has been achieved in 15.3% yield over nine steps, along with its three stereoisomeric triols and ganoderol A. The key steps leading to this family of isomers involve the reconstruction of the trisubstituted alkene by stereoselective and chemoselective phosphonate reactions and the

  灵芝灵芝的一种生物活性羊毛脂三萜烯-灵芝三醇的首次合成已通过9个步骤以15.3％的收率完成，并合成了其三种立体异构三醇和灵芝多酚A。导致该异构体家族的关键步骤涉及重建通过立体选择性和化学选择性膦酸酯反应合成三取代烯烃，并通过羊毛甾酮衍生的环氧化物的温和酸性开放形成异常的Δ7,9（11）-二烯核。灵芝三醇对乳腺癌细胞的抑制和增殖显示出有希望的活性。测定了灵芝三醇及其异构体对细胞增殖的影响。IC 50 对于灵芝三醇，在乳腺癌细胞系MCF-7和MDA-MB-231上分别发现了5.8和9.7μM的值。
• Ganoweberianones A and B, Antimalarial Lanostane Dimers from Cultivated Fruiting Bodies of the Basidiomycete <i>Ganoderma weberianum</i>
  作者：Masahiko Isaka、Panida Chinthanom、Vanicha Vichai、Sujinda Sommai、Rattaket Choeyklin

  DOI：10.1021/acs.jnatprod.0c00879

  日期：2020.11.25

  known compounds (10–12), were isolated from the artificially cultivated fruiting bodies of the basidiomycete Ganoderma weberianum. Ganoweberianone A (1) exhibited significant antimalarial activity against Plasmodium falciparum K1 (multidrug-resistant strain) with an IC50 value of 0.050 μM. A method for semisynthesis of 1 by condensation of the corresponding lanostane monomers and acid-catalyzed intramolecular

  从人工栽培的果实中分离出两种羊毛脂二聚体，灵芝酮 A ( 1 ) 和 B ( 2 )，以及七种先前未描述的羊毛脂，灵芝酸 A–G ( 3 – 9 ) 和三种已知化合物 ( 10 – 12 )担子菌Ganoderma weberianum 的尸体。Ganoweberianone A ( 1 ) 对恶性疟原虫K1（多重耐药菌株）表现出显着的抗疟活性，IC 50值为 0.050 μM。一种用于半合成方法1 通过相应羊毛脂烷单体的缩合和酸催化的分子内酯交换反应得到了证明。
• Lanostane Triterpenes from the Tibetan Medicinal Mushroom <i>Ganoderma leucocontextum</i> and Their Inhibitory Effects on HMG-CoA Reductase and α-Glucosidase
  作者：Kai Wang、Li Bao、Weiping Xiong、Ke Ma、Junjie Han、Wenzhao Wang、Wenbing Yin、Hongwei Liu

  DOI：10.1021/acs.jnatprod.5b00331

  日期：2015.8.28

  Sixteen new lanostane triterpenes, ganoleucoins A-P (1-16), together with 10 known tripterpenes (17-26), were isolated from the cultivated fruiting bodies of Ganoderma leucocontextum, a new member of the Ganoderma lucidum complex. The structures of the new compounds were elucidated by extensive spectroscopic analysis and chemical transformation. The inhibitory effects of 1-26 on HMG-CoA reductase and a-glucosidase were tested in vitro. Compounds 1, 3, 6, 10-14, 17, 18, 23, 25, and 26 showed much stronger inhibitory activity against HMG-CoA reductase than the positive control atorvastatin. Compounds 13, 14, and 16 presented potent inhibitory activity against a-glucosidase from yeast with IC50 values of 13.6, 2.5, and 5.9 mu M, respectively. In addition, the cytotoxicity of 1-26 was evaluated against the K562 and PC-3 cell lines by the MTT assay. Compounds 1, 2, 6, 7, 10, 12, 16, 18, and 25 exhibited cytotoxicity against K562 cells with IC50 values in the range 10-20 mu M. Paclitaxel was used as the positive control with an IC50 value of 0.9 mu M. This is the first report of secondary metabolites from this medicinal mushroom.
• Triterpene-Farnesyl Hydroquinone Conjugates from <i>Ganoderma sinense</i>
  作者：Naoto Sato、Chao-Mei Ma、Katsuko Komatsu、Masao Hattori

  DOI：10.1021/np800687t

  日期：2009.5.22

  Three new lanostane-type triterpenoids having farnesyl hydroquinone moieties, named ganosinensins A-C (1-3), were isolated from the fruiting body of Ganoderma sinense, together with three known lanostane triterpenes, ganodermanontriol, ganoderiol A, and ganoderiol D. The structures of compounds 1-3 were determined by spectroscopic data interpretation.