鬼臼毒素-4-O-葡萄糖苷 | 16481-54-2

• 物质功能分类: 生物化工 - 提取物
• 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: 鬼臼毒素-4-O-葡萄糖苷
• 中文别名: 鬼臼毒素-3-O-葡萄糖苷；鬼臼毒素-7-O-葡萄糖苷
• 英文名称: podophyllotoxin-7′-O-β-D-glucopyranoside
• 英文别名: podophyllotoxin 7'-O-β-D-glucopyranoside；podophyllotoxin-7'-O-β-D-glucopyranoside；podophyllotoxin-4-O-β-D-glucopyranoside；podophyllotoxin-4-O-β-glucoside；podophyllotoxin β-D-glycoside；O-β-D-Glucopyranosyl-podophyllotoxin；Podophyllotoxin glucoside；(5R,5aR,8aR,9R)-5-[(2R,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
• CAS: 16481-54-2
• 化学式: C₂₈H₃₂O₁₃
• 分子量: 576.554
• InChiKey: NXVJTGLCCSFGAT-QNDDJFOYSA-N

物化性质

• 熔点：
  152-154℃
• 密度：
  1.55
• 溶解度：
  少许溶于甲醇
• 沸点：
  781.3±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  172
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  鬼臼毒素-4-O-葡萄糖苷 在 emulsin-substance 作用下， 生成 鬼臼毒素
  参考文献：
  名称：

  从印度鬼臼壁中分离鬼臼毒素苷。2.关于抑制有丝分裂的天然物质的交流

  摘要：

  来自印度毒品鬼臼（Podophyllum emodi）墙的根茎。分离出新的葡糖苷鬼臼毒素-β-D-葡糖苷C 28 H 32 O 13。它的苷元是该药物树脂级分的主要活性成分。可以从根状茎的水溶性部分中分离出氯仿可溶性树脂后，以0.5％至1％的量获得葡糖苷。描述了新葡糖苷的性质。特别值得注意的是在水中的溶解度非常好，在非常温和的碱作用下已经重新排列成微溶的鬼臼苦素-葡萄糖苷，并且容易被β-葡萄糖苷酶裂解，从而可以得到鬼臼毒素和D-葡萄糖。

  DOI：

  10.1002/hlca.19540370620
• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 鬼臼毒素 在 1,4-二巯基-2,3-丁二醇 作用下， 以 various solvents 为溶剂， 生成 鬼臼毒素-4-O-葡萄糖苷
  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

• Biotransformation of Podophyllum lignans in cell suspension cultures of Forsythia intermedia
  作者：A.Jane Broomhead、Paul M. Dewick

  DOI：10.1016/0031-9422(91)84199-3

  日期：1991.1

  Abstract Biotransformation studies using cell suspension cultures of Forsythia intermedia showed these are capable of rapidly oxidizing the aryltetralin lactone lignan podophyllotoxin into podophyllotoxone. Smaller amounts of the stereoisomer picropodophyllone were also produced, probably due to pH changes in the culture during incubation. These ketone products were obtained in up to 40% overall yield

  摘要 使用中间连翘细胞悬浮培养物进行的生物转化研究表明，它们能够将芳基四氢萘内酯木脂素鬼臼毒素快速氧化成鬼臼酮。还产生了少量的立体异构体鬼臼酮，这可能是由于培养过程中培养物的 pH 值变化所致。这些酮产品的总收率高达 40%。当将乙酰鬼臼毒素或鬼臼毒素 4-O-葡萄糖苷加入培养物时，获得了类似的产物，证明存在额外的酯酶和 β-d-葡萄糖苷酶活性。鬼臼苦素类似地转化为鬼臼苦素。去氧鬼臼毒素被转化为鬼臼酮，推测是在氧化之前通过苄基羟基化。检测到建议的羟基中间体的痕量。将含有酚基的木脂素添加到培养物中时会迅速消失而不产生任何生物转化产物，并且可能被分解代谢。使用指数期和 24 小时饲养期的细胞将鬼臼毒素转化为鬼臼酮和鬼臼苦素是最佳的。
• �ber die Partialsynthese von14C-Podophyllotoxin-?-glucosid und zur Darstellung von14C-Diazomethan. 6. Mitteilung �ber mitosehemmende Naturstoffe
  作者：A. Stoll、J. Rutschmann、A. von Wartburg、J. Renz

  DOI：10.1002/hlca.19560390402

  日期：——

  4′-Demethyl-podophyllotoxin-β-glucosid wird mit radioaktivem Diazomethan in 14C-Podophyllotoxin-β-glucosid übergefuhrt. Es wird über eine verbesserte Synthese von 14C-Diazomethan berichtet.

  14 C-鬼臼毒素-β-葡糖苷übergefuhrt中的4'-去甲基鬼臼毒素-β-葡糖苷与重氮基放射性重氮。Es wirdübereine verbesserte合成14 C-重氮甲azo。
• Lignanglucoside aus<i>Podophyllum peltatum L</i>. 7. Mitteilung über mitosehemmende Naturstoffe
  作者：A. von Wartburg、E. Angliker、J. Renz

  DOI：10.1002/hlca.19570400525

  日期：——

  From the rhizomes of american Podophyllum peltatum L. it was possible to isolate and characterize four lignan glucosides with anti-mitotic activity: podophyllotoxin-β-D-glucoside (IX), β-peltatin-β-D-glucoside (XI), 4′-demethylpodophyllotoxin-β-D-glucoside (X) and α-peltatin-β-u-glucoside (XII). The constitution of β-peltatin-β-D- glucoside was deduced from the fact that enzymatic cleavage with emulsin

  从美洲鬼臼的根茎。可以分离并鉴定具有抗有丝分裂活性的四种木脂素葡糖苷：鬼臼毒素-β-D-葡糖苷（IX），β-类维生素A-β-D-葡糖苷（XI），4'-去甲基鬼臼毒素-β-D-葡糖苷（X）和α-Peltatin-β-u-葡萄糖苷（XII）。根据以下事实推论β-类维生素A-β-D-葡萄糖苷的组成：用乳胶酶解产生D-葡萄糖和已知的β-类胡萝卜素。α-Peltatin-β-D-葡萄糖苷是鬼臼类中第一个以结晶形式分离的天然葡萄糖苷，经乳化酶水解后分解为D-葡萄糖和α-Peltatin。可以通过甲基化为鬼臼毒素-β-D-葡萄糖苷和β-peltatin-β-D-的甲基化来确定4'-去甲基鬼臼毒素-β-D-葡萄糖苷和α-Peletatin-β-D-葡萄糖苷中糖成分的位置。糖苷。
• Multi-Layer Tablets and Bioadhesive Dosage Forms
  申请人：Nangia Avinash

  公开号：US20080311191A1

  公开（公告）日：2008-12-18

  Bioadhesives coatings increase the gastrointestinal retention time of orally-ingested medicaments. Certain bioadhesive coatings producing a fracture strength of at least 100 N/m 2 , as measured on rat intestine, when applied to at least one surface of a pharmaceutical dosage form for oral delivery of a drug, result in a gastrointestinal retention time of at least 4 hours in a fed beagle dog model, during which the drug is released from the dosage form. Multi-layer tablets, particularly those including hydrophobic excipients, are useful in administering hygroscopic and/or deliquescent drugs. In addition, varying the amount of drug in multi-layer tablets allows the release rate of the drug to be controlled.

  生物粘合剂涂层可以增加口服药物的胃肠道保留时间。当应用于至少一种药物剂型的表面以口服给药时，产生至少100 N/m²的断裂强度的某些生物粘合剂涂层（在大鼠肠道上测量）可导致在饲养的比格犬模型中至少保留4小时的胃肠道保留时间，在此期间药物从剂型中释放。多层片剂，特别是包括疏水助剂的多层片剂，可用于给予吸湿性和/或易溶性药物。此外，改变多层片剂中药物的量可以控制药物的释放速率。
• Acceptably non-hygroscopic formulation intermediate comprising a hygroscopic drug
  申请人：——

  公开号：US20040197411A1

  公开（公告）日：2004-10-07

  A solid particulate composition is provided comprising a hygroscopic and/or deliquescent drug and at least one non-hygroscopic polymer. The drug and the at least one polymer are in intimate association and the composition is acceptably non-hygroscopic.

  一种固体颗粒组合物由吸湿性和/或潮解性药物和至少一种非吸湿性聚合物组成。药物和至少一种聚合物紧密结合，组合物具有可接受的非吸湿性。