5,8-二甲基龙胆山酮酚 | 49599-09-9

• 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: 5,8-二甲基龙胆山酮酚
• 英文名称: 1,8-dihydroxy-3,5,8-trimethoxyxanthone
• 英文别名: 1-hydroxy-3,5,8-trimethoxy xanthone；1-hydroxy-3,5,8-trimethoxy-xanthone；1-hydroxy-3,5,8-trimethoxyxanthone；1-hydroxy-3,5,8-trimethoxyxanthol；5,8-dimethylbellidifolin；1-hydroxy-3,5,8-trimethoxy-xanthen-9-one；1-Hydroxy-3,5,8-trimethoxyxanthen-9-one
• CAS: 49599-09-9
• 化学式: C₁₆H₁₄O₆
• 分子量: 302.284
• InChiKey: WSRRHFFQNVXIKF-UHFFFAOYSA-N

物化性质

• 熔点：
  204.5 °C
• 沸点：
  513.5±50.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,8-二甲基龙胆山酮酚 、 碘甲烷 在 silver(l) oxide 作用下， 生成 1,3,5,8-tetramethoxy-9H-xanthen-9-one
  参考文献：
  名称：

  Über einen neuen Bestandteil von Swertia japonica, Makino (Gentianaceae)

  摘要：

  DOI：

  10.1246/bcsj.17.104
• 作为产物：
  描述：

  雏菊叶龙胆酮 在 乙醚 、 氢碘酸 、 丙酮 、 苯酚 作用下， 生成 5,8-二甲基龙胆山酮酚
  参考文献：
  名称：

  Über einen neuen Bestandteil von Swertia japonica, Makino (Gentianaceae)

  摘要：

  DOI：

  10.1246/bcsj.17.104

文献信息

• Tri- and tetraoxygenated xanthones from Swertia petiolata
  作者：Khadga S. Khetwal、Binita Joshi、R.S. Bisht

  DOI：10.1016/0031-9422(90)85439-m

  日期：1990.1

  Abstract A new tetra-oxygenated xanthone glycoside: 1-glucosyloxy-3-hydroxy-5,8-dimethoxyxanthone has been isolated and identified from the methanolic extract of the aerial parts of Swertia petiolata along with 1,8-dihydroxy-3,5-dimethoxyxanthone; 1,3-dihydroxy-7-methoxyxanthone and 1,7-dihydroxy-3-methoxyxanthone.

  摘要 一种新的四氧化氧杂蒽酮糖苷：1-葡糖氧基-3-羟基-5,8-二甲氧基氧杂蒽酮与1,8-二羟基-3,5-二甲氧基氧杂蒽酮；1,3-二羟基-7-甲氧基氧杂蒽酮和1,7-二羟基-3-甲氧基氧杂蒽酮。
• Studies on the Constituents of Swertia japonica. IV. Isolation and Structure of Xanthones
  作者：MANKI KOMATSU、TSUYOSHI TOMIMORI、NAOKO MIKURIYA

  DOI：10.1248/cpb.17.155

  日期：——

  The chemical constituents of Swertia japonica MAKINO were studied. Three kinds of new natural xanthones, named norswertianin (I), swertianin (III) and methylswertianin (V), were isolated from the whole herb of this plant, together with desmethylbellidifolin (X) and bellidifolin (XII). I was identified as 1, 3, 7, 8-tetrahydroxyxanthone. The direct isolation of I from natural source has never been published, although it has derived from decussatin (VII) and/or swertinin (VIII) by demethylation. The structure of III and V were shown to be 1, 7, 8-trihydroxy-3-methoxyxanthone and 1, 8-dihydroxy-3, 7-dimethoxy-xanthone, respectively. At the same time, "swertianol"was revised the structure to 1, 5, 8-trihydroxy-3-methoxyxanthone, which was proved to be identical with bellidifolin.

  对獐牙菜MAKINO的化学成分进行了研究。从该植物全草中分离得到三种新的天然呫吨酮，分别命名为norswertianin (I)、swertianin (III)和methylswertianin (V)，以及去甲基bellidifolin (X)和bellidifolin (XII)。我被鉴定为1,3,7,8-四羟基氧杂蒽酮。尽管 I 是通过去甲基化从 decussatin (VII) 和/或 swertinin (VIII) 衍生而来，但从未发表过从天然来源直接分离 I 的方法。 III和V的结构分别为1,7,8-三羟基-3-甲氧基呫吨酮和1,8-二羟基-3,7-二甲氧基-呫吨酮。同时，将“獐牙菜醇”的结构修改为1,5,8-三羟基-3-甲氧基呫吨酮，并证明其与桔梗素相同。
• 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。

表征谱图