盾叶鬼臼素 | 518-29-6

• 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: 盾叶鬼臼素
• 中文别名: (-)-Β-盾叶鬼臼素
• 英文名称: β-peltatin
• 英文别名: beta-Peltatin；(5R)-5,8,8aβ,β-tetrahydro-10-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6 (5aαH)-one；β‐peltatin；(-)-β-peltatin；(5aR,8aR,9R)-4-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• CAS: 518-29-6
• 化学式: C₂₂H₂₂O₈
• 分子量: 414.412
• InChiKey: HLBPOYVRLSXWJJ-PDSMFRHLSA-N

物化性质

• 熔点：
  234 °C
• 比旋光度：
  D20 -122.9° (c = 0.578 in chloroform)
• 沸点：
  586.8±50.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)
• 溶解度：
  3.14e-05 M
• 碰撞截面：
  189 Ų [M+H-H2O]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

安全信息

• 储存条件：
  -20°C密封保存，干燥并避光。

制备方法与用途

(-)-β-Pelatin 是一种具有抗肿瘤活性和植物代谢产物作用的有机异四环化合物，其功能与 α-Pelatin 相关。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  去氧鬼臼毒素	deoxypodophyllotoxin	19186-35-7	C22H22O7	398.412

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	β-Peltatin-B	641-25-8	C22H22O8	414.412
  ——	(-)-β-peltatin-A-methyl ether	23978-65-6	C23H24O8	428.439
  ——	β-peltatin B methyl ether	38943-35-0	C23H24O8	428.439
  ——	5-O-Acetyl-β-peltatin	119906-98-8	C24H24O9	456.449
  ——	(5aR)-10-sulfooxy-5t-(3,4,5-trimethoxy-phenyl)-(5ar,8at)-5,8,8a,9-tetrahydro-5aH-furo[3',4';6,7]naphtho[2,3-d][1,3]dioxol-6-one	——	C22H22O11S	494.476

反应信息

• 作为反应物：
  描述：

  盾叶鬼臼素 在 S-(+)-adenosylmethionine 、 三羟甲基氨基甲烷盐酸盐 作用下， 反应 0.5h， 生成 (-)-β-peltatin-A-methyl ether
  参考文献：
  名称：

  Aryltetralin-lignan formation in two different cell suspension cultures of Linum album: Deoxypodophyllotoxin 6-hydroxylase, a key enzyme for the formation of 6-methoxypodophyllotoxin

  摘要：

  Suspension cultures initiated from two different Linum album seedlings accumulate either podophyllotoxin (PTOX, 2.6 mg/g DW) or 6-methoxypodophyllotoxin (6MPTOX, 5.4 mg/g DW) as main lignans. Two molecules of coniferyl alcohol are dimerized to pinoresinol which is converted via several steps into deoxypodophyllotoxin (DOP) which seems to be the branching point to PTOX or 6MPTOX biosynthesis. DOP is hydroxylated at position 7 to give PTOX by deoxypodophyllotoxin 7-hydroxylase (DOP7H). In contrast, 6MPTOX biosynthesis is achieved by DOP hydroxylation at position 6 to beta-peltatin by the cytochrome P450 enzyme deoxypodophyllotoxin 6-hydroxylase (DOP6H). The following methylation to beta-peltatin-A-methylether is catalyzed by beta-peltatin 6-O-methyltransferase (beta P6OMT) from which 6MPTOX is formed by hydroxylation at position 7 by beta-peltatin-A-methylether 7-hydroxylase (PAM7H). DOP6H and beta P6OMT could be characterized in protein extracts from cell cultures of L. flavum and L. nodiflorum, respectively, and here in L. album for the first time. DOP7H and PAM7H activities could not yet be detected with protein extracts. Experiments of feeding DOP together with inhibitors of cytochrome P450 depending as well as dioxygenase enzymes were performed in order to shed light on the type of DOP7H and PAM7H. Growth parameters and specific activities of enzymes from the phenylpropane as well as the lignan specific biosynthetic pathway were measured during a culture period of 16 days. From the enzymes studied only the DOP6H showed a differential activity sustaining the hypothesis that this enzyme is responsible for the differential lignan accumulation in both cell lines. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.02.031
• 作为产物：
  描述：

  去氧鬼臼毒素 在 三羟甲基氨基甲烷盐酸盐 、 还原型辅酶II(NADPH)四钠盐 作用下， 反应 0.33h， 生成 盾叶鬼臼素
  参考文献：
  名称：

  Aryltetralin-lignan formation in two different cell suspension cultures of Linum album: Deoxypodophyllotoxin 6-hydroxylase, a key enzyme for the formation of 6-methoxypodophyllotoxin

  摘要：

  Suspension cultures initiated from two different Linum album seedlings accumulate either podophyllotoxin (PTOX, 2.6 mg/g DW) or 6-methoxypodophyllotoxin (6MPTOX, 5.4 mg/g DW) as main lignans. Two molecules of coniferyl alcohol are dimerized to pinoresinol which is converted via several steps into deoxypodophyllotoxin (DOP) which seems to be the branching point to PTOX or 6MPTOX biosynthesis. DOP is hydroxylated at position 7 to give PTOX by deoxypodophyllotoxin 7-hydroxylase (DOP7H). In contrast, 6MPTOX biosynthesis is achieved by DOP hydroxylation at position 6 to beta-peltatin by the cytochrome P450 enzyme deoxypodophyllotoxin 6-hydroxylase (DOP6H). The following methylation to beta-peltatin-A-methylether is catalyzed by beta-peltatin 6-O-methyltransferase (beta P6OMT) from which 6MPTOX is formed by hydroxylation at position 7 by beta-peltatin-A-methylether 7-hydroxylase (PAM7H). DOP6H and beta P6OMT could be characterized in protein extracts from cell cultures of L. flavum and L. nodiflorum, respectively, and here in L. album for the first time. DOP7H and PAM7H activities could not yet be detected with protein extracts. Experiments of feeding DOP together with inhibitors of cytochrome P450 depending as well as dioxygenase enzymes were performed in order to shed light on the type of DOP7H and PAM7H. Growth parameters and specific activities of enzymes from the phenylpropane as well as the lignan specific biosynthetic pathway were measured during a culture period of 16 days. From the enzymes studied only the DOP6H showed a differential activity sustaining the hypothesis that this enzyme is responsible for the differential lignan accumulation in both cell lines. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.02.031

文献信息

• Studies in Sugar Chemistry VII1). Glucuronides of Podophyllum Derivatives
  作者：Abraham Nudelman、Margaretta Ruse、Hugo E. Gottlieb、Craig Fairchild

  DOI：10.1002/ardp.19973300904

  日期：——

  The antitumor activities of several glucuronide methyl esters of podophyllum derivatives were tested in vitro against two human tumor cell lines and their drug resistant sublines. The most active compound studied was methyl (4′‐carbobenzoxy‐4′‐demethylepipodophyllotoxin‐D‐glucopyranoside)uronate 19. Compound 19 was as potent in a colon carcinoma model and was twice as potent in a lung carcinoma model

  在体外测试了几种鬼臼衍生物的葡萄糖醛酸甲酯对两种人类肿瘤细胞系及其耐药亚系的抗肿瘤活性。研究的最活跃的化合物是甲基（4'-羧基苯甲氧基-4'-去甲基表鬼臼毒素-D-吡喃葡萄糖苷）糖醛酸 19。化合物 19 在结肠癌模型中的效力与依托泊苷 6 在肺癌模型中的效力相同。然而，在 vivo 小鼠白血病 P388 模型中，它仅具有边缘活性，在 37 mg/kg (iv) 时最大 T/C% 值为 125。
• (−)-Arctigenin as a Lead Structure for Inhibitors of Human Immunodeficiency Virus Type-1 Integrase
  作者：Eckart Eich、Heinz Pertz、Macki Kaloga、Jutta Schulz、Mark R. Fesen、Abhijit Mazumder、Yves Pommier

  DOI：10.1021/jm950387u

  日期：1996.1.1

  congener with two catechol substructures (7) was found to be the most active compound in this study. 7 was also a potent inhibitor of the "disintegration" reaction which models the reversal of the strand transfer reaction. The inhibitory activity of 7 with the core enzyme fragment consisting of amino acids 50-212 suggests that the binding site of 7 resides in the catalytic domain.

  发现天然二苄基丁内酯型木质素（-）-arctigenin（2）是一种人类免疫缺陷病毒1型（HIV-1）在感染的人类细胞系统中复制的抑制剂，可抑制前病毒DNA整合到细胞DNA基因组中。在本研究中，2用纯化的HIV-1整合酶进行了测试，发现在裂解（3'-加工）和整合（链转移）测定中无活性。然而，以儿茶酚亚结构为特征的半合成3-O-去甲基化同源物9在两种测定中均表现出显着的活性。用30种天然（1-6），半合成（7-21）和合成（37-43、45、46）的木脂素进行结构-活性关系研究表明，（1）内酯部分至关重要，因为带有丁烷-1的化合物，4-二醇或四氢呋喃的亚结构以及木脂酰胺类似物缺乏活性，（2）酚羟基的数量和排列对于木质素的活性很重要。在本研究中，发现具有两个邻苯二酚亚结构的同类物（7）是活性最高的化合物。7也是“崩解”反应的有效抑制剂，其模拟了链转移反应的逆转。7对由氨基酸50-212组成的核
• [EN] METHODS AND COMPOSITIONS FOR TREATING CANCER<br/>[FR] MÉTHODES ET COMPOSITIONS POUR LE TRAITEMENT DU CANCER
  申请人：UNIV HEALTH NETWORK

  公开号：WO2015051447A1

  公开（公告）日：2015-04-16

  A compound of Formula I and/or II and/or a composition comprising a compound of Formula I and/or II is described as well as uses of said compounds and compositions for inhibiting microtubule polymerization, inducing lysosome disruption and/or treating a cancer, including a hematological cancer such as leukemia.

  本文描述了一种由式I和/或II的化合物和/或包含式I和/或II的组合物组成的化合物，以及所述化合物和组合物用于抑制微管聚合、诱导溶酶体破裂和/或治疗癌症的用途，包括像白血病这样的血液系统癌症。
• [EN] PPAR modulators<br/>[FR] MODULATEURS DES RAPP
  申请人：NESTEC SA

  公开号：WO2015028456A1

  公开（公告）日：2015-03-05

  The present invention relates to the field of metabolic and inflammatory disorders and aims to identify natural compounds that can be used effectively in this field. In particular, the (I) for use in the treatment or prevention of a metabolic or chronic inflammatory disorder.

  本发明涉及代谢和炎症性疾病领域，并旨在确定可在该领域有效使用的天然化合物。具体而言，本发明涉及(I)，用于治疗或预防代谢性或慢性炎症性疾病。
• 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。