豨莶精醇 | 5940-00-1

• 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: 豨莶精醇
• 中文别名: 莶精醇
• 英文名称: darutigenol
• 英文别名: (1R)-1-[(2S,4aR,4bS,7R,8aS)-7-hydroxy-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-yl]ethane-1,2-diol
• CAS: 5940-00-1
• 化学式: C₂₀H₃₄O₃
• 分子量: 322.488
• InChiKey: NCAZLDCEJHFJDT-KHKZNYETSA-N

物化性质

• 熔点：
  168-170 °C(Solv: benzene (71-43-2))
• 沸点：
  471.2±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO：64mg/mL（198.46mM）；；

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

制备方法与用途

概述

经过反复试验筛选发现，豨莶精醇对体外和体内血栓形成、血小板聚集和粘附、优球蛋白溶解时间、血栓模型血液流变学及血栓素B2（TXB2）、前列环素I2（PGI2）和出凝血时间等方面具有良好的作用。它是一种活性化合物，在植物中的含量为0.08%至0.2%，含量较高。

用途

豨莶精醇可用于治疗心脑血管血栓性疾病及抗血栓。

生物活性

Darutigenol 具有显著的抗血栓作用，可能与其抑制血小板聚集和粘附有关。

化学性质

Darutigenol 是一种无色液体，可溶于甲醇、乙醇、DMSO 等有机溶剂。它来源于豨莶草（Siegesbeckia orientalis L.）。

反应信息

• 作为反应物：
  描述：

  豨莶精醇 在 吡啶 、 4-二甲氨基吡啶 、 phosphomolybdic acid hydrate 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 生成 3-acetoxydarutogenol
  参考文献：
  名称：

  Semisynthesis of ent-norstrobane diterpenoids as potential inhibitor for factor Xa

  摘要：

  A semisynthesis of two ent-strobane diterpenoids strobols C (7) and D (14) was accomplished via a Wagnar-Meerwein rearrangement. Compounds 7, 14, and the intermediate products were evaluated for their inhibition on factor Xa (FXa). Among all the compounds screened for FXa inhibitory activity, three compounds 6, 7, and 9 showed significant inhibitory activities with IC50 values of 1067 +/- 164, 81 +/- 11, 1023 +/- 89 nM, respectively. The inhibitory activity on FXa described in this study highlight the importance of structural modification based on natural products in the development of FXa inhibitors.

  DOI：

  10.1016/j.bmcl.2018.05.036
• 作为产物：
  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

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。
• Short, Divergent, and Enantioselective Total Synthesis of Bioactive <i>ent</i>-Pimaranes
  作者：Immanuel Plangger、Klaus Wurst、Thomas Magauer

  DOI：10.1021/acs.orglett.2c02843

  日期：2022.10.7

  We present the first total synthesis of eight ent-pimaranes via a short and enantioselective route (11–16 steps). Key features of the divergent synthesis are a Sharpless asymmetric dihydroxylation, a Brønsted acid catalyzed cationic bicyclization, and a mild Rh-catalyzed arene hydrogenation for rapid access to a late synthetic branching point. From there on, selective functional group manipulations

  我们首次通过一条短的对映选择性路线（11-16 步）全合成了八种ent -pimarane。发散合成的主要特征是 Sharpless 不对称二羟基化、Brønsted 酸催化的阳离子双环化和温和的 Rh 催化的芳烃氢化以快速获得后期合成支化点。从那时起，选择性的官能团操作能够合成在 A 环和 C 环中带有不同修饰的ent -pimaranes。
• COSMETIC COMPOSITIONS COMPRISING ORIDONIN AND NEW COSMETIC USES
  申请人：Fournial Arnaud

  公开号：US20120028916A1

  公开（公告）日：2012-02-02

  The present invention related to cosmetic compositions comprising oridonin and new cosmetic uses. Oridonin is used for fighting the signs of cutaneous aging and for slimming. A composition comprising a combination of oridonin and darutigenol or a derivative thereof, in particular darutoside, is disclosed together with the cosmetic use of such composition.
• US9050477B2
  申请人：——

  公开号：US9050477B2

  公开（公告）日：2015-06-09
• Semisynthesis of ent-norstrobane diterpenoids as potential inhibitor for factor Xa
  作者：Jianbin Wang、He Ma、Hongzheng Fu

  DOI：10.1016/j.bmcl.2018.05.036

  日期：2018.12

  A semisynthesis of two ent-strobane diterpenoids strobols C (7) and D (14) was accomplished via a Wagnar-Meerwein rearrangement. Compounds 7, 14, and the intermediate products were evaluated for their inhibition on factor Xa (FXa). Among all the compounds screened for FXa inhibitory activity, three compounds 6, 7, and 9 showed significant inhibitory activities with IC50 values of 1067 +/- 164, 81 +/- 11, 1023 +/- 89 nM, respectively. The inhibitory activity on FXa described in this study highlight the importance of structural modification based on natural products in the development of FXa inhibitors.