1,8-二羟基-3,5-二甲氧基氧杂蒽-9-酮 | 521-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 1,8-二羟基-3,5-二甲氧基氧杂蒽-9-酮
• 英文名称: methylbellidifolin
• 英文别名: 1,8-dihydroxy-3,5-dimethoxyxanthone；swerchirin；1,8-dihydroxy-3,5-dimethoxy-9H-xanthen-9-one；1,8-dihydroxy-3,5-dimethoxyxanthen-9-one
• CAS: 521-65-3
• 化学式: C₁₅H₁₂O₆
• 分子量: 288.257
• InChiKey: GNSHHHWDGOHNPC-UHFFFAOYSA-N

物化性质

• 保留指数：
  2625.5

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  1,8-二羟基-3,5-二甲氧基氧杂蒽-9-酮 生成 1,3,5,8-tetramethoxy-9H-xanthen-9-one
  参考文献：
  名称：

  Dalal; Shah, Chemistry and industry, 1956, p. 664

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(β-D-glucopyranosyloxy)-8-hydroxy-3,5-dimethoxy-9H-xanthen-9-one 在 硫酸 作用下， 生成 1,8-二羟基-3,5-二甲氧基氧杂蒽-9-酮
  参考文献：
  名称：

  Nakaoki; Hida, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1943, vol. 63, p. 554

  摘要：

  DOI：

文献信息

• Synthesis of xanthoneO-glycosides. Part III. Synthesis of 1- and 8-O-?-D-glycosides of 5-O-methyl- and de-O-methylbellidifolin
  作者：Barbara Vermes、Otto Seligmann、Hildebert Wagner

  DOI：10.1002/hlca.19850680832

  日期：1985.12.18

  The unambiguous synthesis of three naturally occurring and biologically active xanthone 1-O and 8-O-β-D-glucosides of 5-O-methyl- and de-O-methylbellidifolin (2–4) was accomplished. The protected xanthone aglycones having only a single reactive OH group were prepared by selective benzylation, methylation, and debenzoylation reactions. An unexpected stability of the 1-MeO group towards demethylation

  完成了3种天然存在且具有生物活性的蒽酮1- O和8 - O -β-D-葡萄糖苷（5- O-甲基-和去-O-甲基bellidifolin（2-4）的明确合成）。通过选择性苄基化，甲基化和脱苯甲酰化反应制备仅具有单个反应性OH基团的被保护的蒽酮苷元。观察到1-MeO基团对去甲基化的出乎意料的稳定性。
• Studies on the mutagenicity of Swertiae Herba. I. Identification of the mutagenic components.
  作者：HISAYUKI KANAMORI、IKUNORI SAKAMOTO、MARI MIZUTA、KAZUHISA HASHIMOTO、OSAMU TANAKA

  DOI：10.1248/cpb.32.2290

  日期：——

  The mutagenicity of the extract of Swertiae Herba is attributable to its xanthone derivatives. Seven active principles were isolated and six of them were identified as methylbellidifolin, methylswertianin, swertianin, bellidifolin, norswertianin and desmethylbellidifolin, all of which have already been isolated from this plant. The seventh mutagenic compound, a new xanthone derivative formulated as 5, 8-dimethylbellidifolin, was also obtained from methylbellidifolin by methylation with diazomethane as a minor product. The structure-mutagenicity relationship of these compounds, together with some other derivatives, is discussed.

  獐牙菜提取物的致突变性归因于其呫吨酮衍生物。分离出 7 种活性成分，其中 6 种被鉴定为methylbellidifolin、methylswertianin、swertianin、bellidifolin、norswertianin 和 desmethylbellidifolin，所有这些都已从该植物中分离出来。第七种诱变化合物是一种新的呫吨酮衍生物，被配制为 5, 8-二甲基bellidifolin，也是通过用重氮甲烷甲基化作为次要产物从甲基bellidifolin 中获得的。讨论了这些化合物以及一些其他衍生物的结构-致突变性关系。
• Xanthone Glycoside Constituents of <i>Swertia kouitchensis</i> with α-Glucosidase Inhibitory Activity
  作者：Luo-Sheng Wan、Qiu-Xia Min、Yong-Long Wang、Yao-Dong Yue、Jia-Chun Chen

  DOI：10.1021/np400082g

  日期：2013.7.26

  Ten new xanthone glycosides, kouitchensides A–J (1–10), and 11 known analogues were isolated from an n-butanol fraction of Swertia kouitchensis. The structures of these glycosides were determined on the basis of extensive spectroscopic data interpretation and comparison with data reported in the literature. In an in vitro test, compounds 2, 4, 5, 6, 11, 12, and 13 (IC50 values in the range 126 to 451

  从Swertia kouitchensis的正丁醇级分中分离出十个新的黄酮苷，kouitchensides A–J（1 – 10）和11种已知的类似物。这些糖苷的结构是在广泛的光谱数据解释和与文献报道的数据比较的基础上确定的。在体外测试中，化合物2，4，5，6，11，12，和13（IC 50个范围为126至451μM值）显示对α葡糖苷酶活性更有效的抑制效果比阳性对照，阿卡波糖（ IC 50 值627μM）。
• A xanthone from Swertia chirayita
  作者：Rakesh K. Asthana、Narendra K. Sharma、Dinesh K. Kulshreshtha、Sunil K. Chatterjee

  DOI：10.1016/0031-9422(91)85308-m

  日期：1991.1

  Abstract The structure of new xanthone from Swertia chirayita has been established as 1,5-dihydroxy-3,8-dimethoxy xanthone (chiratol) on the basis of spectral and chemical evidence. Two other xanthones, i.e. swerchirin (1,8-dihydroxy-3,5-dimethoxy xanthone) and 7- O -methyl swertianin (1,8-dihydroxy-3,7-dimethoxy xanthone) have been isolated. Swerchirin was identified as the hypoglycaemic principle

  摘要 基于光谱和化学证据，来自Swertia chirayita 的新氧杂蒽酮的结构已确定为1,5-二羟基-3,8-二甲氧基氧杂蒽酮（chiratol）。已分离出另外两种呫吨酮，即 swerchirin（1,8-二羟基-3,5-二甲氧基氧杂蒽酮）和 7-O-甲基 swertianin（1,8-二羟基-3,7-二甲氧基氧杂蒽酮）。Swerchirin 被确定为植物的降血糖原理。
• Novel class of hybrid natural products as antidiabetic agents
  作者：Kanwal Raj、Namita Misra、Geetali Pachauri、Mithelesh Sharma、Akhilesh Kumar Tamrakar、Amar Bahadur Singh、Arvind Kumar Srivastava、K. Phani Kiran、C.V. Narasimha Rao、S.R. Prubhu

  DOI：10.1080/14786410701824940

  日期：2009.1.10

  A number of O-alkylated xanthone, carbazoles and coumarins have been synthesised and screened for their in vitro anti-diabetic activity, such as glucose-6-phosphatase, glycogen phosphorylase and alpha glucosidase inhibitors. Compounds which were showing significant percentage inhibition were also tested for in vivo anti-hyperglycemic activity in sucrose loaded normal and streptozotocin (STZ)-induced diabetic rats. These compounds show 22.1, 24.4 and 26.7% and 20.8, 25.0, 20.5% lowering in sucrose loaded normal rats and STZ-induced diabetic rats at a dose of 100 mg kg-1.