生物活性 Deoxypodophyllotoxin(DPT),鬼臼毒素的一种衍生物,是一种木酚素。它从Sinopodophyllexandrum的根茎中分离得到,并展现出强效的抗有丝分裂和抗病毒特性。作为一种靶向微管的药物,Deoxypodophyllotoxin不仅是有效的抗有丝分裂剂,还能作为血管生成抑制剂,在肿瘤学领域发挥重要作用。研究表明,该化合物能诱导细胞自噬(autophagy)和细胞凋亡(apoPTosis),并引起DRG神经元细胞内Ca2+浓度增加。
体外研究 Deoxypodophyllotoxin(浓度为25-75 nM;作用时间为6-48小时)显著增加了早期凋亡细胞的比例,从2.05%分别增长到24小时后的5.62%和48小时后的18.49%。此外,在SGC-7901细胞中,该化合物以时间和剂量依赖的方式导致G2/M期细胞周期阻滞,并显著下调了Cdc2和Cdc25C的表达水平,同时在6小时内上调cyclin B1表达,随后抑制了PARP、Bcl-2及caspase-3活性。
凋亡分析
细胞周期分析
Western Blot分析
体内研究 Deoxypodophyllotoxin(静脉注射;剂量分别为5、10和20 mg/kg;每周三次,共28天)表现出剂量依赖性的肿瘤抑制作用。在裸鼠异种移植模型中,用SGC-7901细胞构建的胃癌肿瘤生长分别被抑制了22.19%、47.91%及50.93%。
实验结果
化学性质 无色棱柱状结晶(无水乙醇中),可溶于甲醇、乙醇及DMSO等有机溶剂。该化合物来源于桃儿七Sinopodophyllexandrum和八角莲Dysosma versipellis 的根茎。
用途 去氧鬼臼毒素具有抗肿瘤活性。
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
—— | deoxypicropodophyllin | 24150-39-8 | C22H22O7 | 398.412 |
—— | (5R,5aR,8aR)-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydro-[2]benzofuro[5,6-f][1,3]benzodioxole-6,8-dione | 160869-33-0 | C22H20O8 | 412.396 |
—— | 6,7-demethylenedeoxypodophyllotoxin | 1173-42-8 | C21H22O7 | 386.401 |
—— | (5R,6R,7R)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6,7-dicarboxylic acid | 160823-61-0 | C22H22O9 | 430.411 |
鬼臼脂毒酮 | podophyllotoxone | 477-49-6 | C22H20O8 | 412.396 |
鬼臼毒素 | podofilox | 518-28-5 | C22H22O8 | 414.412 |
—— | bis[(1S)-2-methoxy-2-oxo-1-phenylethyl] (5R,6R,7R)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6,7-dicarboxylate | 160823-59-6 | C40H38O13 | 726.734 |
—— | bis[(1S)-2-methoxy-2-oxo-1-phenylethyl] (5R,6S,7R)-5-hydroxy-5-(3,4,5-trimethoxyphenyl)-7,8-dihydro-6H-benzo[f][1,3]benzodioxole-6,7-dicarboxylate | 160823-58-5 | C40H38O14 | 742.733 |
Yatein; (-)-反式-3-(3,4-亚甲基二氧基苄基)-2-(3,4,5-三甲氧基苄基)丁内酯 | yatein | 40456-50-6 | C22H24O7 | 400.428 |
—— | rac-4-{benzo[d][1,3]dioxol-5-yl(hydroxy)methyl}-3-(3,4,5-trimethoxybenzyl)dihydrofuran-2(3H)-one | —— | C22H24O8 | 416.428 |
—— | (+)-γ-Apopicropodophyllin | 668-01-9 | C22H20O7 | 396.397 |
—— | 1-(3',4',5'-trimethoxyphenyl)-1,2-dihydro-4,5-methylenedioxybenzocyclobuten-1-ol | 134454-88-9 | C18H18O6 | 330.337 |
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
—— | deoxypicropodophyllin | 24150-39-8 | C22H22O7 | 398.412 |
4 ’-去甲去氧鬼臼毒素 | 4'-demethyl-4-deoxypodophyllotoxin | 3590-93-0 | C21H20O7 | 384.386 |
—— | 3',4'-didemethyl-1-desoxypodophyllotoxin | —— | C20H18O7 | 370.359 |
—— | 6,7-demethylenedeoxypodophyllotoxin | 1173-42-8 | C21H22O7 | 386.401 |
—— | (3aS,4R,9aR)-6,7-dihydroxy-4-(3,4,5-trimethoxyphenyl)-3a,4,9,9a-tetrahydro-1H-benzo[f][2]benzofuran-3-one | 3590-88-3 | C21H22O7 | 386.401 |
—— | desoxypodophyllinic acid ethyl ester | 78215-95-9 | C24H28O8 | 444.482 |
—— | Desoxypodophyllinsaeure-methylester | 1643-12-5 | C23H26O8 | 430.455 |
—— | deoxypicropodophyllinic acid methyl ester | 140147-76-8 | C23H26O8 | 430.455 |
—— | 4'-demethyl-6,7-demethylenedesoxypodophyllotoxin | —— | C20H20O7 | 372.375 |
—— | methyl (5R,6S,7R)-7-formyl-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylate | 171483-28-6 | C23H24O8 | 428.439 |
—— | ethyl (5R,6R,7R)-7-(methoxymethoxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylate | 514223-12-2 | C26H32O9 | 488.535 |
—— | 4'-demethyl-4'-O-benzyl-1-desoxypodophyllotoxin | —— | C28H26O7 | 474.51 |
—— | deoxypicropodophyllic acid | 1254-07-5 | C22H24O8 | 416.428 |
—— | [4-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-2,6-dimethoxyphenyl] N-ethylcarbamate | 13091-61-7 | C24H25NO8 | 455.464 |
盾叶鬼臼素 | β-peltatin | 518-29-6 | C22H22O8 | 414.412 |
—— | [4-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-2,6-dimethoxyphenyl] (Z)-octadec-11-enoate | —— | C39H52O8 | 648.837 |
—— | 4'-O-trans-11-eicosenoyl-4'-demethyldeoxypodophyllotoxin | —— | C41H56O8 | 676.891 |
—— | 4'-O-all-cis-5,8,11,14-eicosatetraenoyl-4'-demethyldeoxypodophyllotoxin | —— | C41H50O8 | 670.843 |
—— | 4'-O-all-cis-11,14-eicosadienoyl-4'-demethyldeoxypodophyllotoxin | —— | C41H54O8 | 674.875 |
—— | 4'-O-(diethylphosphoryl)-4'-demethyl-1-desoxypodophyllotoxin | —— | C25H29O10P | 520.473 |
—— | deoxyanhydro-4-isopodophyllol | 321747-09-5 | C22H24O6 | 384.429 |
6,8-二溴-4-氧代-4H-1-苯并吡喃-3-甲醛 | 9-deoxyanhydropodophyllol | 25088-82-8 | C22H24O6 | 384.429 |
—— | 2-(4-deoxyl-4'-demethylpodophyllotoxinoxy)-N-phenylacetamide | —— | C29H27NO8 | 517.535 |
—— | 4'-demethyl-4'-O-tert-butyldimethylsilyl-1-desoxypodophyllotoxin | —— | C27H34O7Si | 498.648 |
—— | 4'-demethyl-4-deoxypodophyllotoxin 4'-(4-methylpiperazine) carbamate | 1308813-80-0 | C27H30N2O8 | 510.544 |
—— | 2-(4-deoxyl-4'-demethylpodophyllotoxinoxy)-N-(p-methoxyphenyl)acetamide | —— | C30H29NO9 | 547.562 |
—— | 2-(4-deoxyl-4'-demethylpodophyllotoxinoxy)-N-(o-methylphenyl)acetamide | —— | C30H29NO8 | 531.562 |
鬼臼脂毒酮 | podophyllotoxone | 477-49-6 | C22H20O8 | 412.396 |
(5R)-5,8,8ab,9-四氢-5b-(3,4,5-三甲氧基苯基)呋喃并[3',4':6,7]萘并[2,3-d]-1,3-二氧杂环戊烯-6(5abH),9-二酮 | (5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione | 477-48-5 | C22H20O8 | 412.396 |
—— | 2-(4-deoxyl-4'-demethylpodophyllotoxinoxy)-N-(m-fluorophenyl)acetamide | —— | C29H26FNO8 | 535.526 |
—— | [(5R,6R,7R)-7-(methoxymethoxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxol-6-yl]methanol | 514223-09-7 | C24H30O8 | 446.497 |
—— | 2-(4-deoxyl-4'-demethylpodophyllotoxinoxy)-N-(m-chlorophenyl)acetamide | —— | C29H26ClNO8 | 551.98 |
5,8,8a,9-四氢-9-羟基-5-(3,4,5-三甲氧基苯基)-(5R,5aR,8aR,9S)-呋喃并[3',4':6,7]萘并[2,3-d]-1,3-二氧杂环戊烯-6(5aH)-酮 | epipodophyllotoxin | 4375-07-9 | C22H22O8 | 414.412 |
鬼臼毒素 | podofilox | 518-28-5 | C22H22O8 | 414.412 |
—— | (6R,7R,8R)-6-(methoxymethoxymethyl)-7-methyl-8-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole | 514223-13-3 | C24H30O7 | 430.498 |
—— | 9-deoxypodophyllol | 31104-02-6 | C22H26O7 | 402.444 |
—— | 2-(4-deoxyl-4'-demethylpodophyllotoxinoxy)-N-(o-chlorophenyl)acetamide | —— | C29H26ClNO8 | 551.98 |
—— | [(6R,7R,8R)-7-methyl-8-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxol-6-yl]methanol | 514223-14-4 | C22H26O6 | 386.445 |
—— | 1-bromo-desoxypodophyllotoxin | —— | C22H21BrO7 | 477.309 |
—— | 1α-bromo-desoxypodophyllotoxin | 106636-74-2 | C22H21BrO7 | 477.309 |
—— | 4β-bromo-4-desoxypodophyllotoxin | 106636-74-2 | C22H21BrO7 | 477.309 |
—— | 6,7-O-Demethylen-epipodophyllotoxin | 1174-96-5 | C21H22O8 | 402.401 |
—— | 2'-bromodeoxypodophyllotoxin | 93108-13-5 | C22H21BrO7 | 477.309 |
(3aR,4S,9R,9aR)-4,6,7-三羟基-9-(4-羟基-3,5-二甲氧苯基)-3a,4,9,9a-四氢萘并[2,3-c]呋喃-1(3H)-酮 | 6,7-O,O-demethylene-4'-O-demethylepipodophyllotoxin | 138456-91-4 | C20H20O8 | 388.374 |
—— | 2-(4-deoxyl-4'-demethylpodophyllotoxinoxy)-N-(m-nitrophenyl)acetamide | —— | C29H26N2O10 | 562.533 |
—— | 4'-demethyl-4-deoxypodophyllotoxin 4'-(4-p-hydroxyphenylpiperazine) carbamate | 1308813-86-6 | C32H32N2O9 | 588.614 |
—— | 2-(4-deoxyl-4'-demethylpodophyllotoxinoxy)-N-(2-chloro-6-methylphenyl)acetamide | —— | C30H28ClNO8 | 566.007 |
—— | 4'-demethyl-4-deoxypodophyllotoxin 4'-(4-p-fluorophenylpiperazine) carbamate | 1308813-82-2 | C32H31FN2O8 | 590.605 |
—— | 2-(4-deoxyl-4'-demethylpodophyllotoxinoxy)-N-(o-nitrophenyl)acetamide | —— | C29H26N2O10 | 562.533 |
—— | [(5R,6R,7R)-7-(methoxymethoxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxol-6-yl]methyl methanesulfonate | 514223-10-0 | C25H32O10S | 524.589 |
—— | 4'-demethyl-4-deoxypodophyllotoxin 4'-(4-p-nitrophenylpiperazine) carbamate | 1308813-81-1 | C32H31N3O10 | 617.612 |
—— | 6,7-demethylene-1-O-ethyl-1-epipodophyllotoxin | —— | C23H26O8 | 430.455 |
—— | 6,7-demethylene-4'-demethyl-1-O-ethyl-1-epipodophyllotoxin | —— | C22H24O8 | 416.428 |
—— | (5R,5aR,8aR)-5-(4-methoxyphenazin-2-yl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one | 1445712-09-3 | C26H20N2O5 | 440.455 |
(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 | 5-methoxypodophyllotoxin | 128443-52-7 | C23H24O9 | 444.438 |
—— | (5R,5aR,8aR)-5-(8-amino-4-methoxyphenazin-2-yl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one | 1445712-13-9 | C26H21N3O5 | 455.47 |
—— | (5R,5aR,8aR)-5-(7-amino-4-methoxyphenazin-2-yl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one | 1445712-12-8 | C26H21N3O5 | 455.47 |
—— | [4-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-2,6-dimethoxyphenyl] N-[(2S)-4-methylsulfanyl-1-[4-(4-nitrophenyl)piperazin-1-yl]-1-oxobutan-2-yl]carbamate | 1308813-91-3 | C37H40N4O11S | 748.811 |
—— | [4-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-2,6-dimethoxyphenyl] N-[(2R)-4-methylsulfanyl-1-[4-(4-nitrophenyl)piperazin-1-yl]-1-oxobutan-2-yl]carbamate | 1308813-92-4 | C37H40N4O11S | 748.811 |
—— | N-[8-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-6-methoxyphenazin-2-yl]acetamide | 1445712-23-1 | C28H23N3O6 | 497.507 |
—— | N-[7-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-9-methoxyphenazin-2-yl]acetamide | 1445712-14-0 | C28H23N3O6 | 497.507 |
—— | [4-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-2,6-dimethoxyphenyl] N-[(2S)-1-[4-(4-nitrophenyl)piperazin-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamate | 1308813-89-9 | C41H40N4O11 | 764.789 |
—— | [4-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-2,6-dimethoxyphenyl] N-[(2R)-1-[4-(4-nitrophenyl)piperazin-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamate | 1308813-90-2 | C41H40N4O11 | 764.789 |
—— | N-[8-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-6-methoxyphenazin-2-yl]-2-chloroacetamide | 1445712-24-2 | C28H22ClN3O6 | 531.952 |
—— | N-[7-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-9-methoxyphenazin-2-yl]-2-chloroacetamide | 1445712-15-1 | C28H22ClN3O6 | 531.952 |
—— | N-[8-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-6-methoxyphenazin-2-yl]propanamide | 1445712-25-3 | C29H25N3O6 | 511.534 |
—— | N-[7-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-9-methoxyphenazin-2-yl]propanamide | 1445712-16-2 | C29H25N3O6 | 511.534 |
—— | (5R,5aR,8aR)-5-(4-methoxy-8-nitrophenazin-2-yl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one | 1445712-11-7 | C26H19N3O7 | 485.453 |
—— | (5R,5aR,8aR)-5-(4-methoxy-7-nitrophenazin-2-yl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one | 1445712-10-6 | C26H19N3O7 | 485.453 |
—— | N-[8-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-6-methoxyphenazin-2-yl]heptanamide | 1445712-27-5 | C33H33N3O6 | 567.642 |
—— | N-[7-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-9-methoxyphenazin-2-yl]heptanamide | 1445712-17-3 | C33H33N3O6 | 567.642 |
—— | N-[8-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-6-methoxyphenazin-2-yl]-2-methylprop-2-enamide | 1445712-26-4 | C30H25N3O6 | 523.545 |
—— | [(1S,12R,15R)-1-(3,4,5-trimethoxyphenyl)-5,7,14-trioxatetracyclo[10.2.1.02,10.04,8]pentadeca-2,4(8),9-trien-15-yl]methanol | 321747-15-3 | C22H24O7 | 400.428 |
—— | N-[8-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-6-methoxyphenazin-2-yl]benzamide | 1445712-28-6 | C33H25N3O6 | 559.578 |
—— | N-[7-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-9-methoxyphenazin-2-yl]benzamide | 1445712-18-4 | C33H25N3O6 | 559.578 |
—— | N-[8-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-6-methoxyphenazin-2-yl]-4-methoxybenzamide | 1445712-32-2 | C34H27N3O7 | 589.604 |
—— | N-[7-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-9-methoxyphenazin-2-yl]-4-methoxybenzamide | 1445712-21-9 | C34H27N3O7 | 589.604 |
—— | N-[8-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-6-methoxyphenazin-2-yl]-3-methoxybenzamide | 1445712-31-1 | C34H27N3O7 | 589.604 |
—— | N-[7-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-9-methoxyphenazin-2-yl]-3-methoxybenzamide | 1445712-20-8 | C34H27N3O7 | 589.604 |
—— | N-[8-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-6-methoxyphenazin-2-yl]-3,4-dimethoxybenzamide | 1445712-33-3 | C35H29N3O8 | 619.631 |
—— | N-[7-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-9-methoxyphenazin-2-yl]-3,4-dimethoxybenzamide | 1445712-22-0 | C35H29N3O8 | 619.631 |
—— | 5-methoxypodophyllotoxin-4-O-β-D-glucoside | 119188-52-2 | C29H34O14 | 606.581 |