trillin

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: trillin
• 英文别名: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxane-3,4,5-triol
• 化学式: C₃₃H₅₂O₈
• 分子量: 576.771
• InChiKey: WXMARHKAXWRNDM-RBRZMXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  41
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  trillin 在 咪唑 、 乙醚 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 三氟化硼 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.5h， 生成 纤细薯蓣皂苷
  参考文献：
  名称：

  Synthesis of diosgenyl α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→3)]-β-d-glucopyranoside (gracillin) and related saponins

  摘要：

  Diosgenyl alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-glucopyranoside (gracillin), a monodesmosidic saponin isolated from paris, dioscorea, and costacea species with promising cardiovascular and antitumor activities, was synthesized by stepwise glycosylation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(97)10050-7
• 作为产物：
  描述：

  薯蓣皂素 在 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 10.0h， 生成 trillin
  参考文献：
  名称：

  Synthesis of diosgenyl α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→3)]-β-d-glucopyranoside (gracillin) and related saponins

  摘要：

  Diosgenyl alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-glucopyranoside (gracillin), a monodesmosidic saponin isolated from paris, dioscorea, and costacea species with promising cardiovascular and antitumor activities, was synthesized by stepwise glycosylation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(97)10050-7

文献信息

• Substrate specificity, purification and identification of a novel pectinase with the specificity of hydrolyzing the α-1,4-glycosyl residue in steroidal saponin
  作者：Bing Feng、Hong-zhi Huang、Wen-bin Zhou、Li-ping Kang、Peng Zou、Yi-xun Liu、He-shui Yu、Bin-qing Han、Ya-yong Li、Ling-ling Zhang、Tao Zhang、Bai-ping Ma

  DOI：10.1016/j.procbio.2010.05.009

  日期：2010.8

  It is known that the sugar chain linked to steroidal frame plays an important role in physiological and pharmacological activities. In the previous research, we found and confirmed that the terminal C3-O-alpha-1,2-rhamnosyl moiety linked to the C-3 of steroidal saponin is the key group of platelet aggregation and cytotoxicity. In order to make a complete approach for the structure-activity relationship, we have tried to find the specific enzymes modifying the structure of C3-sugar chain. In the present paper, we describe a novel enzyme from, Klerzyme-150 (K-150), which is specifically capable of hydrolyzing the alpha-1,4-glycosyl residues at C-3 postion of steroidal saponins. 15 steroidal saponins with different monosaccharides at C3-sugar chains were chosen as substrates to investigate the substrate specificity of K-150. The results showed, based on TLC. HPLC and spectra data analyses, that all products were determined as secondary saponins with the alpha-1, 4-glycosyl residues removed, which indicated that the enzyme exhibited strict regioselectivity and stereoselectivity. The novel enzyme was purified from K-150 to apparent homogeneity and its structure was identified as rhamnogalacturonan lyase A (Rgl A). The molecular mass of the purified enzyme was 52.08 kDa. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of diosgenyl α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→3)]-β-d-glucopyranoside (gracillin) and related saponins
  作者：Chuan Li、Biao Yu、Meizheng Liu、Yongzheng Hui*

  DOI：10.1016/s0008-6215(97)10050-7

  日期：1998.1

  Diosgenyl alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-glucopyranoside (gracillin), a monodesmosidic saponin isolated from paris, dioscorea, and costacea species with promising cardiovascular and antitumor activities, was synthesized by stepwise glycosylation. (C) 1998 Elsevier Science Ltd. All rights reserved.