darutoside | 59219-65-7

• 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
• 英文名称: darutoside
• 英文别名: (2R,3R,4S,5S,6R)-2-[[(2R,4aS,4bR,7S,10aS)-7-[(1R)-1,2-dihydroxyethyl]-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthren-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 59219-65-7
• 化学式: C₂₆H₄₄O₈
• 分子量: 484.631
• InChiKey: QWWPCQGHWWNGET-LCVVDEIYSA-N

物化性质

• 熔点：
  234 °C
• 沸点：
  667.0±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)
• 溶解度：
  溶于甲醇和DMSO
• LogP：
  1.780 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性

Darutoside 是一种从 Siegesbeckia 中提取的二萜化合物，来源于豨莶草。

反应信息

• 作为反应物：
  描述：

  darutoside 在 β-cellulase 、 水 作用下， 反应 48.0h， 以34.3 mg的产率得到豨莶精醇
  参考文献：
  名称：

  Cytotoxic Germacrane-Type Sesquiterpenes, Pimarane-Type Diterpenes, and a Naphthalene Derivative from Wollastonia biflora

  摘要：

  Phytochemical investigation of the whole plants of Wollastonia biflora led to the isolation and identification of three new germacrane-type sesquiterpenes (1-3), two new pimarane-type diterpenes (4-5), and a new naphthalene glycoside (6), along with 11 known compounds. Their structures were characterized on the basis of spectroscopic analyses and chemical methods. Compounds 1, 2, and 3 showed significant cytotoxic activity against the growth of hepatocellular carcinoma BEL-7402 cells in vitro.

  DOI：

  10.1021/np060515p
• 作为产物：
  描述：

  ent-(15R)-acetoxypimar-8(14)-ene-3β,16-diol 3-O-β-D-glucopyranoside 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 168000.0h， 以100%的产率得到darutoside
  参考文献：
  名称：

  ent-Pimarane-Type Diterpenoids from Siegesbeckia orientalis L.

  摘要：

  A new ent-pimarane glucoside, named hythiemoside B (4), was isolated from the aerial part of Siegesbecikia orientalis L. (Asteraceae) together with four known ent-pimarane-type diterpenoids: darutigenol (1), darutoside (2), hythiemoside A (3), and ent-(15R),16,19-trihydroxypimar-8(14)-ene 19-O-β-D-glucopyranoside (5). The structure of the new compound was elucidated by spectroscopic analyses and chemical transformation. The NMR data of compounds 1 (1H-) and 5 (1H- and 13C-) were also compiled in this study on the basis of 2D experiments.

  DOI：

  10.1248/cpb.53.232

文献信息

• New melampolides and darutigenol from Sigesbeckia orientalis
  作者：R.N. Barua、Ram P. Sharma、Gopalakrishna Thyagarajan、Werner Herz、Serengolam V. Govindan

  DOI：10.1016/s0031-9422(00)81985-8

  日期：1980.1

  Abstract Isolation and identification of darutigenol and two new melampolides from Sigesbeckia orientalis , in addition to the previously described orientalide and darutoside, are reported.

  摘要 除先前描述的东方香皂苷和 darutoside 外，还报道了从东方蝽中分离和鉴定 darutigenol 和两种新的 melampolides。
• Cytotoxic Germacrane-Type Sesquiterpenes, Pimarane-Type Diterpenes, and a Naphthalene Derivative from <i>Wollastonia </i><i>biflora</i>
  作者：Wenliang Chen、Weidong Tang、Rujun Zhang、Liguang Lou、Weimin Zhao

  DOI：10.1021/np060515p

  日期：2007.4.1

  Phytochemical investigation of the whole plants of Wollastonia biflora led to the isolation and identification of three new germacrane-type sesquiterpenes (1-3), two new pimarane-type diterpenes (4-5), and a new naphthalene glycoside (6), along with 11 known compounds. Their structures were characterized on the basis of spectroscopic analyses and chemical methods. Compounds 1, 2, and 3 showed significant cytotoxic activity against the growth of hepatocellular carcinoma BEL-7402 cells in vitro.
• ent-Pimarane-Type Diterpenoids from Siegesbeckia orientalis L.
  作者：Phan Minh Giang、Phan Tong Son、Hideaki Otsuka

  DOI：10.1248/cpb.53.232

  日期：——

  A new ent-pimarane glucoside, named hythiemoside B (4), was isolated from the aerial part of Siegesbecikia orientalis L. (Asteraceae) together with four known ent-pimarane-type diterpenoids: darutigenol (1), darutoside (2), hythiemoside A (3), and ent-(15R),16,19-trihydroxypimar-8(14)-ene 19-O-β-D-glucopyranoside (5). The structure of the new compound was elucidated by spectroscopic analyses and chemical transformation. The NMR data of compounds 1 (1H-) and 5 (1H- and 13C-) were also compiled in this study on the basis of 2D experiments.