(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 | 128443-52-7

• 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
• 中文名称: (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
• 英文名称: 5-methoxypodophyllotoxin
• 英文别名: 6-methoxypodophyllotoxin；MPT；2'-methoxypodophyllotoxin；(5R,5aR,8aR,9R)-5-hydroxy-4-methoxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• CAS: 128443-52-7
• 化学式: C₂₃H₂₄O₉
• 分子量: 444.438
• InChiKey: PDQAOYGENRRPQO-UXDKQJBESA-N

物化性质

• 沸点：
  605.0±55.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  甲醇 、 去氧鬼臼毒素 在 Linum flavum 、 2,6-di-O-methyl-β-cyclodextrin 作用下， 以 正丁醇 为溶剂， 反应 168.0h， 以75.3%的产率得到5-methoxypodophyllotoxin-4-O-β-D-glucoside
  参考文献：
  名称：

  The Large-Scale Isolation of Deoxypodophyllotoxin from Rhizomes of Anthriscus sylvestris Followed by Its Bioconversion into 5-Methoxypodophyllotoxin β-d-Glucoside by Cell Cultures of Linum flavum

  摘要：

  Dried rhizomes of Anthriscus sylvestris contained 0.39% deoxypodophyllotoxin (1). An isolation procedure with an extraction efficiency of 51.2% was developed for this commercially unavailable lignan. The isolated 1 was subsequently complexed with dimethyl-P-cyclodextrin and fed to cell suspension cultures of Linum flavum by which it was bioconverted into 5-methoxypodophyllotoxin-beta-D-glucoside (2). After 7 days the cells contained 4.41% of this product on a dry-weight basis. An isolation procedure for compound 2 was developed, with an extraction efficiency of 83.4%.

  DOI：

  10.1021/np960748o

文献信息

• Lignans from Juniperus sabina
  作者：Arturo San Feliciano、Jose M. Miguel del Corral、Marina Gordaliza、Angeles Castro

  DOI：10.1016/0031-9422(90)85460-w

  日期：1990.1

  Four new natural products, β-peltatin-B methyl ether, podorhizol acetate, 2′-methoxyepipicropodophyllotoxin and 2′-methoxypicropodophyllotoxin, were isolated from the lignan fraction of a n -hexane extract from the leaves of Juniperus sabina , along with picropodophyllotoxone, epipodophyllotoxin, (+)-dihydrosesamin, podorhizol, anhydropodorhizol, epipicropodophyllotoxin and 2′-methoxypodophyllotoxin

  摘要 从刺柏叶-己烷提取物的木脂素组分中分离得到4种新的天然产物β-peltatin-B甲基醚、醋酸鬼臼毒、2'-甲氧基鬼臼毒和2'-甲氧基鬼臼毒，以及鬼臼乙酮、鬼臼毒。 , (+)-dihydrosesamin, podorhizol, anhydropodorhizol, 表鬼臼毒和 2'-甲氧基鬼臼毒。
• Aryltetralin lignans from Linum flavum and Linum capitatum
  作者：A.Jane Broomhead、Paul M. Dewick

  DOI：10.1016/0031-9422(90)85343-e

  日期：——
• 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.
• The Large-Scale Isolation of Deoxypodophyllotoxin from Rhizomes of <i>Anthriscus sylvestris</i> Followed by Its Bioconversion into 5-Methoxypodophyllotoxin β-<scp>d</scp>-Glucoside by Cell Cultures of <i>Linum flavum</i>
  作者：Wim Van Uden、Jeroen A. Bos、Gesiena M. Boeke、Herman J. Woerdenbag、Niesko Pras

  DOI：10.1021/np960748o

  日期：1997.4.1

  Dried rhizomes of Anthriscus sylvestris contained 0.39% deoxypodophyllotoxin (1). An isolation procedure with an extraction efficiency of 51.2% was developed for this commercially unavailable lignan. The isolated 1 was subsequently complexed with dimethyl-P-cyclodextrin and fed to cell suspension cultures of Linum flavum by which it was bioconverted into 5-methoxypodophyllotoxin-beta-D-glucoside (2). After 7 days the cells contained 4.41% of this product on a dry-weight basis. An isolation procedure for compound 2 was developed, with an extraction efficiency of 83.4%.