6-MethoxyPodophyllotoxin-7-Glucoside

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: 6-MethoxyPodophyllotoxin-7-Glucoside
• 英文别名: 6-methoxypodophyllotoxin glucoside；(5R,5aR,8aR,9R)-4-methoxy-5-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• 化学式: C₂₉H₃₄O₁₄
• 分子量: 606.581
• InChiKey: ZBHUQQHYXHVILV-ODNJTVIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  181
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 (5R,5aR,8aR,9R)-9-羟基-10-甲氧基-5-(3,4,5-三甲氧基苯基)-5a,8,8a,9-四氢-5H-异苯并呋喃并[6,5-f][1,3]苯并二氧戊环-6-酮 在 1,4-二巯基-2,3-丁二醇 作用下， 以 various solvents 为溶剂， 生成 6-MethoxyPodophyllotoxin-7-Glucoside
  参考文献：
  名称：

  UDP-glucose:(6-methoxy)podophyllotoxin 7-O-glucosyltransferase from suspension cultures of Linum nodiflorum

  摘要：

  Cell cultures of Linum species store 6-methoxypodophyllotoxin (MPTOX), podophyllotoxin (PTOX) and related lignans as O-glucosides. UDP-glucose:(M)PTOX 7-O-glucosyltransferase has been detected and characterised in protein preparations of suspension-cultured cells of Linum nodiflorum L. (Linaceac). The maximal lignan glucoside contents in the cells are preceded by a rapid increase of the specific glucosyltransferase, activity on day six of the culture period. MPTOX glucoside is the major lignan with up to 1.18 mg g(-1) of the cell dry wt which is more than 30-fold of the PTOX glucoside content. Of the three aryltetralin lignans tested as substrates, PTOX and MPTOX display comparable apparent K-m values of 4.7 and 5.4 mu M, respectively. 5'-Demethoxy-6-methoxypodophyllotoxin is converted with the highest velocity of 25.2 pkat mg(-1) while also possessing a higher K-m of 14.7 mu M. Two-substrate test series indicate that all three compounds compete for the active site of a single protein. The structurally similar lignan O-peltatin acts as competitive inhibitor as well. However, the 6-O-glucosidation is most likely catalysed by a separate enzyme. The (M)PTOX 7-O-glucosyltransferase works best at a pH around 9 and a temperature around 35 degrees C. A 15-30% increase of the reaction rate is effected by the addition of 0.9 mM Mn2+. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.07.030

文献信息

• UDP-glucose:(6-methoxy)podophyllotoxin 7-O-glucosyltransferase from suspension cultures of Linum nodiflorum
  作者：Anna Berim、Rainer Ebel、Bernd Schneider、Maike Petersen

  DOI：10.1016/j.phytochem.2007.07.030

  日期：2008.1

  Cell cultures of Linum species store 6-methoxypodophyllotoxin (MPTOX), podophyllotoxin (PTOX) and related lignans as O-glucosides. UDP-glucose:(M)PTOX 7-O-glucosyltransferase has been detected and characterised in protein preparations of suspension-cultured cells of Linum nodiflorum L. (Linaceac). The maximal lignan glucoside contents in the cells are preceded by a rapid increase of the specific glucosyltransferase, activity on day six of the culture period. MPTOX glucoside is the major lignan with up to 1.18 mg g(-1) of the cell dry wt which is more than 30-fold of the PTOX glucoside content. Of the three aryltetralin lignans tested as substrates, PTOX and MPTOX display comparable apparent K-m values of 4.7 and 5.4 mu M, respectively. 5'-Demethoxy-6-methoxypodophyllotoxin is converted with the highest velocity of 25.2 pkat mg(-1) while also possessing a higher K-m of 14.7 mu M. Two-substrate test series indicate that all three compounds compete for the active site of a single protein. The structurally similar lignan O-peltatin acts as competitive inhibitor as well. However, the 6-O-glucosidation is most likely catalysed by a separate enzyme. The (M)PTOX 7-O-glucosyltransferase works best at a pH around 9 and a temperature around 35 degrees C. A 15-30% increase of the reaction rate is effected by the addition of 0.9 mM Mn2+. (C) 2007 Elsevier Ltd. All rights reserved.