杨梅酮 | 32492-74-3

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 中文名称: 杨梅酮
• 英文名称: myricanone
• 英文别名: Myricanon；3,15-dihydroxy-16,17-dimethoxytricyclo[12.3.1.12,6]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one
• CAS: 32492-74-3
• 化学式: C₂₁H₂₄O₅
• 分子量: 356.419
• InChiKey: ZTSNTUQTNQSIDC-UHFFFAOYSA-N

物化性质

• 熔点：
  190-192 °C
• 沸点：
  583.7±50.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)
• LogP：
  3.790 (est)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  76
• 氢给体数：
  2
• 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

杨梅酮是从杨梅树皮中提取出的一种化合物[1]。

反应信息

• 作为反应物：
  描述：

  杨梅酮 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 54.0h， 生成 (S)-8,9-dimethoxy-2,3,3a,4,5,6-hexahydro-1H-benzo[4,5]-cycloocta[1,2,3-de]naphthalene-7,11-diol
  参考文献：
  名称：

  进入12成员的环状邻位，间-二芳基庚烷类化合物：通过异麦芽酮酮合成放线菌酮

  摘要：

  我们在此描述〜12元环[7,0]第一接入邻，间位-diarylheptanoids。合成的关键特征包括Suzuki-Miyaura偶联和闭环易位。放线菌酮，一种有前途的天然产物，以及具有生物活性的四环衍生物，是第14步首次从廉价的市售底物中获得，总收率为18-21％。我们的作案手法通过使用显着的战略反应来符合综合理想化的原则。

  DOI：

  10.1021/acs.joc.0c02489
• 作为产物：
  描述：

  在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 palladium on activated charcoal 、 氢气 、 potassium acetate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 生成 杨梅酮
  参考文献：
  名称：

  Synthesis, Stereochemical Analysis, and Derivatization of Myricanol Provide New Probes That Promote Autophagic Tau Clearance

  摘要：

  We previously discovered that one specific scalemic preparation of myricanol (1), a constituent of Myrica cerifera (bayberry/southern wax myrtle) root bark, could lower the levels of the microtubule-associated protein tau (MAPT). The significance is that tau accumulates in a number of neurodegenerative diseases, the most common being Alzheimers disease (AD). Herein, a new synthetic route to prepare myricanol using a suitable boronic acid pinacol ester intermediate is reported. An X-ray crystal structure of the isolated myricanol (1) was obtained and showed a co-crystal consisting of (+)-aR,11S-myricanol (2) and (-)-aS,11R-myricanol (3) coformers. Surprisingly, 3, obtained from chiral separation from 1, reduced tau levels in both cultured cells and ex vivo brain slices from a mouse model of tauopathy at reasonable mid-to-low micromolar potency, whereas 2 did not. SILAC proteomics and cell assays revealed that 3 promoted tau degradation through an autophagic mechanism, which was in contrast to that of other tau-lowering compounds previously identified by our group. During the course of structureactivity relationship (SAR) development, we prepared compound 13 by acid-catalyzed dehydration of 1. 13 had undergone an unexpected structural rearrangement through the isomyricanol substitution pattern (e.g., 16), as verified by X-ray structural analysis. Compound 13 displayed robust tau-lowering activity, and, importantly, its enantiomers reduced tau levels similarly. Therefore, the semisynthetic analogue 13 provides a foundation for further development as a tau-lowering agent without its SAR being based on chirality.

  DOI：

  10.1021/cb501013w

文献信息

• [EN] MYRICANOL DERIVATIVES AND USES THEREOF FOR TREATMENT OF NEURODEGENERATIVE DISEASES<br/>[FR] DÉRIVÉS DE MYRICANOL ET LEURS UTILISATIONS POUR LE TRAITEMENT DE MALADIES NEURODÉGÉNÉRATIVES
  申请人：UNIV SOUTH FLORIDA

  公开号：WO2013152350A1

  公开（公告）日：2013-10-10

  The subject invention pertains to myricanol derivatives, therapeutic compositions, and methods for treatment of neurodegenerative diseases, in particular, neurodegenerative diseases associated with abnormal accumulation of protein tau.

  该发明涉及油松醇衍生物、治疗组合物和治疗神经退行性疾病的方法，特别是与蛋白质tau异常积累相关的神经退行性疾病。
• [EN] INHIBITING HYDROCARBON HYDRATE AGGLOMERATION<br/>[FR] INHIBITION DE L'AGGLOMÉRATION D'HYDRATES D'HYDROCARBURES
  申请人：COMMW SCIENT IND RES ORG

  公开号：WO2018218281A1

  公开（公告）日：2018-12-06

  A process for inhibiting the formation of gas hydrates in a hydrocarbon fluid comprising adding to the hydrocarbon fluid, a gas hydrate anti-agglomerate which is a biodegradable anti-agglomerant derived from a naturally occurring substance.

  一种抑制碳氢化合物流体中天然气水合物形成的方法包括向碳氢化合物流体中添加一种气体水合物抗凝聚剂，该抗凝聚剂是一种可生物降解的抗凝聚剂，来源于天然存在的物质。
• Bioactive Constituents of Chinese Natural Medicines. VII. Inhibitors of Degranulation in RBL-2H3 Cells and Absolute Stereostructures of Three New Diarylheptanoid Glycosides from the Bark of Myrica rubra.
  作者：Hisashi Matsuda、Toshio Morikawa、Jing Tao、Kazuho Ueda、Masayuki Yoshikawa

  DOI：10.1248/cpb.50.208

  日期：——

  Three new diarylheptanoid glycosides, named (+)-S-myricanol 5-O-β-D-glucopyranoside, myricanene A 5-O-α-L-arabinofuranosyl(1→6)-β-D-glucopyranoside, and myricanene B 5-O-α-L-arabinofuranosyl(1→6)-β-D-glucopyranoside, were isolated from the bark of Chinese Myrica rubra, together with twenty known compounds. The absolute stereostructures of the new diarylheptanoid glycosides were elucidated on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method. The inhibitory effects of isolated constituents on the release of β-hexosaminidase from RBL-2H3 cells were examined, and several diarylheptanoids, myricanol, (+)-S-myricanol, myricanone, and myricanenes A and B, and a flavonol, myricetin, were found to show the inhibitory activity.

  从中国杨梅树的树皮中分离出了三种新的日芳丙烯糖苷，分别命名为 (+)-S-美利卡醇 5-O-β-D-葡萄糖苷、桂皮醇 A 5-O-α-L-阿拉伯呋喃糖苷（1→6）-β-D-葡萄糖苷，以及桂皮醇 B 5-O-α-L-阿拉伯呋喃糖苷（1→6）-β-D-葡萄糖苷，同时还分离出了二十种已知化合物。新的日芳丙烯糖苷的绝对立体结构通过化学和物理化学证据明确，包括改进的莫舍尔法的应用。研究了分离化合物对 RBL-2H3 细胞中 β-氨基酮糖苷酶释放的抑制作用，发现几种日芳丙烯化合物、美利卡醇、(+)-S-美利卡醇、桂皮酮以及桂皮醇 A 和 B，还有一种黄酮类化合物美利克林，均表现出抑制活性。
• Inhibitors of nitric oxide production from the bark of Myrica rubra: structures of new biphenyl type diarylheptanoid glycosides and taraxerane type triterpene
  作者：Jing Tao、Toshio Morikawa、Iwao Toguchida、Shin Ando、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1016/s0968-0896(02)00314-0

  日期：2002.12

  Three new biphenyl type diarylheptanoid glycosides, myricanol 11-O-beta-D-glucopyranoside, myricanone 5-O-beta-D-glucopyranoside, and neomyricanone 5-O-beta-D-glucopyranoside, and a new taraxerane type triterpene, myricetrione, were isolated from the bark of Chinese Myrica rubra. Their structures were elucidated on the basis of chemical and physicochemical evidence. Biphenyl type diarylheptanoids,

  三种新的联苯型二芳基庚烷糖苷，肉豆蔻醇11-O-β-D-吡喃葡萄糖苷，肉豆蔻酮5-O-β-D-吡喃葡萄糖苷和新杨烷酮5-O-β-D-吡喃葡萄糖苷，以及新的酒石烷类三萜烯，杨酮从杨梅树的树皮中分离得到。在化学和物理化学证据的基础上阐明了它们的结构。联苯型二芳基庚烷，三萜及其多酚对脂多糖激活的巨噬细胞中的一氧化氮产生有效的抑制作用。此外，发现二芳基庚烷，肉豆蔻醇和肉豆蔻酮可抑制诱导型一氧化氮合酶的诱导。
• Diarylheptanoid Sulfates and Related Compounds from <i>Myrica rubra</i> Bark
  作者：Morio Yoshimura、Saori Yamakami、Yoshiaki Amakura、Takashi Yoshida

  DOI：10.1021/np300212c

  日期：2012.10.26

  Three new diarylheptanoids, myricanol 11-sulfate (1), juglanin B 11-sulfate (2), and myricanone 5-O-(6′-O-galloyl)glucoside (3), were isolated from the bark of Myrica rubra. Compounds 1 and 2 were characterized as diarylheptanoid sulfates on the basis of spectroscopic analyses. The antioxidative activities of the fractionated extracts and isolated compounds were estimated by the oxygen radical absorbance

  从杨梅的树皮中分离出三种新的二芳基庚烷类化合物，硫酸杨醇11（1），茄宁B 11硫酸盐（2）和杨酮5- O-（6' - O-半乳糖基）葡萄糖苷（3）。根据光谱分析，将化合物1和2表征为硫酸二芳基庚烷。分馏的提取物和分离的化合物的抗氧化活性通过氧自由基吸收能力（ORAC）和超氧化物歧化酶（SOD）样活性测定进行估算。主要分离物，杨梅素（4）表现出较高的ORAC值和中等的SOD样活性（分别为13198μmolTE （Trolox当量）/ g和IC 50 127.5μg/ mL），这可能解释了这种材料的强抗氧化活性。