丹參二醇C

丹參二醇C(英語:Tanshindiol C)是一種多環有機化合物,分子式C18H16O5,屬於一種丹參酮類化合物[2][3],與丹參二醇B立體異構體,存在於丹參Salvia miltiorrhiza[1][4]植物中。它可以環己-2-烯酮為原料,經丹參醇B維基數據所列Q82885063中間體,通過多步反應製得[5]

丹參二醇C
別名 紫丹參甲素D
識別
CAS號 96839-30-4  checkY
PubChem 126072
SMILES
 
  • Cc1coc2c1C(=O)C(=O)c1c-2ccc2c1CC[C@@H](O)[C@]2(C)O
性質
化學式 C18H16O5
摩爾質量 312.32 g·mol−1
熔點 213-215 °C[1]
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

參考文獻

  1. ^ 1.0 1.1 Luo, Hou-Wei; Wu, Bao-Jing; Wu, Mei-Yu; Yong, Zhong-Gen; Niwa, Masatake; Hirata, Yoshimasa. Pigments from Salvia miltiorrhiza. Phytochemistry. 1985-01, 24 (4): 815–817. doi:10.1016/S0031-9422(00)84900-6. 
  2. ^ Yang, Y; Li, X; Peng, L; An, L; Sun, N; Hu, X; Zhou, P; Xu, Y; Li, P; Chen, J. Tanshindiol C inhibits oxidized low-density lipoprotein induced macrophage foam cell formation via a peroxiredoxin 1 dependent pathway.. Biochimica et biophysica acta. Molecular basis of disease. 2018-03, 1864 (3): 882–890. PMID 29287777. doi:10.1016/j.bbadis.2017.12.033. 
  3. ^ Zhou, P; Cheng, Y; Liu, F; Wu, K; Qiu, W; Wang, S. Tanshindiol-C suppresses in vitro and in vivo hepatocellular cancer cell growth by inducing mitochondrial-mediated apoptosis, cell cycle arrest, inhibition of angiogenesis and modulation of key tumor-suppressive miRNAs.. Journal of B.U.ON. : official journal of the Balkan Union of Oncology. 2019-03, 24 (2): 622–627. PMID 31128015. 
  4. ^ Yang, M; Liu, A; Guan, S; Sun, J; Xu, M; Guo, D. Characterization of tanshinones in the roots of Salvia miltiorrhiza (Dan-shen) by high-performance liquid chromatography with electrospray ionization tandem mass spectrometry.. Rapid communications in mass spectrometry : RCM. 2006, 20 (8): 1266–80. PMID 16548051. doi:10.1002/rcm.2447. 
  5. ^ Wang, Fan; Yang, Hong; Yu, Shujuan; Xue, Yu; Fan, Zhoulong; Liang, Gaolin; Geng, Meiyu; Zhang, Ao; Ding, Chunyong. Total synthesis of (±)-tanshinol B, tanshinone I, and (±)-tanshindiol B and C. Organic & Biomolecular Chemistry. 2018, 16 (18): 3376–3381. doi:10.1039/C8OB00567B.