(-)-Deoxypodophyllotoxin (BioDeep_00000171472)

   

human metabolite blood metabolite natural product


代谢物信息卡片


10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one

化学式: C22H22O7 (398.1365)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: COC1=CC(=CC(=C1OC)OC)C2C3C(CC4=CC5=C(C=C24)OCO5)COC3=O
InChI: InChI=1S/C22H22O7/c1-24-17-6-12(7-18(25-2)21(17)26-3)19-14-8-16-15(28-10-29-16)5-11(14)4-13-9-27-22(23)20(13)19/h5-8,13,19-20H,4,9-10H2,1-3H3

描述信息

D000890 - Anti-Infective Agents > D000998 - Antiviral Agents
D007155 - Immunologic Factors > D018796 - Immunoconjugates
D007155 - Immunologic Factors > D007136 - Immunoglobulins
D007155 - Immunologic Factors > D000906 - Antibodies
D009676 - Noxae > D000922 - Immunotoxins

同义名列表

11 个代谢物同义名

10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one; deoxypodophyllotoxin, (5R-(5alpha,5aalpha,8aalpha))-isomer; deoxypodophyllotoxin, (5alpha,5aalpha,8aalpha)-(+-)-isomer; deoxypodophyllotoxin, (5R-(5alpha,5aalpha,8abeta))-isomer; deoxypodophyllotoxin, (5R-(5alpha,5abeta,8aalpha))-isomer; deoxypodophyllotoxin, (5alpha,5aalpha,8abeta)-(+-)-isomer; deoxypodophyllotoxin, (5R-(5alpha,5abeta,8abeta))-isomer; (-)-Deoxypodophyllotoxin; isodeoxypodophyllotoxin; deoxypicropodophyllin; Deoxypodophyllotoxin



数据库引用编号

5 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

233 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 14 ABCB1, AIMP2, ANG, ANXA5, BCL2, CASP3, CASP9, CCNB1, CDC25C, CDK1, CTNNB1, MAPK8, TP73, TUBB4B
Peripheral membrane protein 2 ANXA5, CYP1B1
Endoplasmic reticulum membrane 3 BCL2, CDK1, CYP1B1
Nucleus 16 AIMP2, ANG, BCL2, CASP3, CASP9, CCNB1, CDC25C, CDK1, CTNNB1, H2AX, MAPK8, MMP2, MYCN, PARP1, TP73, TUBB4B
cytosol 14 AIMP2, ANG, ANXA5, BCL2, CASP3, CASP9, CCNB1, CDC25C, CDK1, CTNNB1, MAPK8, PARP1, TP73, TUBB4B
nuclear body 1 PARP1
centrosome 4 CCNB1, CDK1, CTNNB1, H2AX
nucleoplasm 10 CASP3, CCNB1, CDC25C, CDK1, CTNNB1, H2AX, MAPK8, MYCN, PARP1, TP73
Cell membrane 2 ABCB1, CTNNB1
lamellipodium 1 CTNNB1
Multi-pass membrane protein 1 ABCB1
Synapse 2 CTNNB1, MAPK8
cell cortex 1 CTNNB1
cell junction 2 CTNNB1, TP73
cell surface 1 ABCB1
glutamatergic synapse 2 CASP3, CTNNB1
Golgi apparatus 1 TP73
growth cone 1 ANG
neuronal cell body 2 ANG, CASP3
presynaptic membrane 1 CTNNB1
sarcolemma 1 ANXA5
Cytoplasm, cytosol 2 AIMP2, PARP1
plasma membrane 3 ABCB1, CTNNB1, MMP2
Membrane 10 ABCB1, AIMP2, ANXA5, BCL2, CCNB1, CDK1, CTNNB1, CYP1B1, MYCN, PARP1
apical plasma membrane 1 ABCB1
axon 1 MAPK8
basolateral plasma membrane 1 CTNNB1
extracellular exosome 6 ABCB1, ANXA5, CDK1, CTNNB1, H2AX, TUBB4B
endoplasmic reticulum 1 BCL2
extracellular space 2 ANG, MMP2
perinuclear region of cytoplasm 2 CDC25C, CTNNB1
Schaffer collateral - CA1 synapse 1 CTNNB1
adherens junction 1 CTNNB1
apicolateral plasma membrane 1 CTNNB1
bicellular tight junction 1 CTNNB1
mitochondrion 6 BCL2, CASP9, CDK1, CYP1B1, MMP2, PARP1
protein-containing complex 4 BCL2, CASP9, CTNNB1, PARP1
intracellular membrane-bounded organelle 2 CYP1B1, TP73
Microsome membrane 1 CYP1B1
postsynaptic density 1 CASP3
Secreted 1 ANG
extracellular region 4 ANG, ANXA5, MMP2, TUBB4B
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
mitochondrial matrix 2 CCNB1, CDK1
transcription regulator complex 2 CTNNB1, PARP1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 CDK1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 ANXA5
Extracellular vesicle 1 TUBB4B
actin cytoskeleton 1 ANG
Z disc 1 CTNNB1
beta-catenin destruction complex 1 CTNNB1
microtubule cytoskeleton 1 TUBB4B
nucleolus 3 ANG, MYCN, PARP1
Wnt signalosome 1 CTNNB1
midbody 1 CDK1
apical part of cell 1 CTNNB1
cell-cell junction 1 CTNNB1
postsynaptic membrane 1 CTNNB1
Apical cell membrane 1 ABCB1
pore complex 1 BCL2
Cytoplasm, cytoskeleton 2 CTNNB1, TUBB4B
focal adhesion 2 ANXA5, CTNNB1
microtubule 1 TUBB4B
Cell junction, adherens junction 1 CTNNB1
flotillin complex 1 CTNNB1
extracellular matrix 1 MMP2
basement membrane 1 ANG
mitochondrial intermembrane space 1 CDC25C
collagen-containing extracellular matrix 2 ANXA5, MMP2
fascia adherens 1 CTNNB1
lateral plasma membrane 1 CTNNB1
nuclear speck 1 H2AX
sarcomere 1 MMP2
Zymogen granule membrane 1 ANXA5
chromatin 3 MYCN, PARP1, TP73
cell periphery 1 CTNNB1
mitotic spindle 2 CDK1, TUBB4B
Chromosome 3 ANG, H2AX, PARP1
cytoskeleton 1 TUBB4B
Cytoplasm, cytoskeleton, cilium basal body 1 CTNNB1
Nucleus, nucleolus 2 ANG, PARP1
spindle pole 2 CCNB1, CTNNB1
nuclear replication fork 1 PARP1
chromosome, telomeric region 2 CDK1, PARP1
postsynaptic density, intracellular component 1 CTNNB1
microvillus membrane 1 CTNNB1
site of double-strand break 2 H2AX, PARP1
intercellular bridge 1 TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
nuclear envelope 1 PARP1
Endomembrane system 1 CTNNB1
axonemal microtubule 1 TUBB4B
Cytoplasm, Stress granule 1 ANG
cytoplasmic stress granule 1 ANG
euchromatin 1 CTNNB1
replication fork 1 H2AX
myelin sheath 1 BCL2
male germ cell nucleus 1 H2AX
XY body 1 H2AX
endocytic vesicle 1 ANG
[Isoform 1]: Secreted, extracellular space, extracellular matrix 1 MMP2
beta-catenin-TCF complex 1 CTNNB1
azurophil granule lumen 1 TUBB4B
apoptosome 1 CASP9
condensed nuclear chromosome 1 H2AX
outer kinetochore 1 CCNB1
presynaptic active zone cytoplasmic component 1 CTNNB1
vesicle membrane 1 ANXA5
protein-DNA complex 2 CTNNB1, PARP1
spindle microtubule 1 CDK1
external side of apical plasma membrane 1 ABCB1
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
nucleosome 1 H2AX
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
catenin complex 1 CTNNB1
site of DNA damage 2 H2AX, PARP1
cyclin-dependent protein kinase holoenzyme complex 1 CDK1
angiogenin-PRI complex 1 ANG
cyclin A1-CDK1 complex 1 CDK1
cyclin A2-CDK1 complex 1 CDK1
cyclin B1-CDK1 complex 2 CCNB1, CDK1
endothelial microparticle 1 ANXA5
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
BAD-BCL-2 complex 1 BCL2
beta-catenin-TCF7L2 complex 1 CTNNB1
beta-catenin-ICAT complex 1 CTNNB1
Scrib-APC-beta-catenin complex 1 CTNNB1
caspase complex 1 CASP9


文献列表

  • Keisuke Kobayashi, Masaomi Yamamura, Bunzo Mikami, Akira Shiraishi, Masato Kumatani, Honoo Satake, Eiichiro Ono, Toshiaki Umezawa. Anthriscus sylvestris Deoxypodophyllotoxin Synthase Involved in Podophyllotoxin Biosynthesis. Plant & cell physiology. 2023 Oct; ?(?):. doi: 10.1093/pcp/pcad103. [PMID: 37948767]
  • Haoyu Tang, Min-Hao Wu, Hsiao-Yu Lin, Meng-Ru Han, Yueh-Hua Tu, Zhi-Jie Yang, Tun-Cheng Chien, Nei-Li Chan, Wei-Chen Chang. Mechanistic analysis of carbon-carbon bond formation by deoxypodophyllotoxin synthase. Proceedings of the National Academy of Sciences of the United States of America. 2022 01; 119(1):. doi: 10.1073/pnas.2113770119. [PMID: 34969844]
  • Davide Decembrino, Alessandra Raffaele, Ronja Knöfel, Marco Girhard, Vlada B Urlacher. Synthesis of (-)-deoxypodophyllotoxin and (-)-epipodophyllotoxin via a multi-enzyme cascade in E. coli. Microbial cell factories. 2021 Sep; 20(1):183. doi: 10.1186/s12934-021-01673-5. [PMID: 34544406]
  • Ya-Nan Li, Ni Ning, Lei Song, Yun Geng, Jun-Ting Fan, Chao-Ying Ma, He-Zhong Jiang. Derivatives of Deoxypodophyllotoxin Induce Apoptosis through Bcl-2/Bax Proteins Expression. Anti-cancer agents in medicinal chemistry. 2021; 21(5):611-620. doi: 10.2174/1871520620999200730160952. [PMID: 32748757]
  • Chang Zu, Yinglan Yu, Caiwei Yu, Yi Li, Runing Sun, Birendra Chaurasiya, Baoqiang Tang, Daquan Chen, Jiasheng Tu, Yan Shen. Highly loaded deoxypodophyllotoxin nano-formulation delivered by methoxy polyethylene glycol-block-poly (D,L-lactide) micelles for efficient cancer therapy. Drug delivery. 2020 Dec; 27(1):248-257. doi: 10.1080/10717544.2020.1716875. [PMID: 32003255]
  • Yilin Qiao, Nathan K Sunada, Alyssa E Hatada, Ingo Lange, Manana Khutsishvili, Valida Alizade, Daniel Atha, Dana-Lynn Ko'omoa-Lange, Robert P Borris. Potential anti-neuroblastoma agents from Juniperus oblonga. Biochemical and biophysical research communications. 2019 08; 516(3):733-738. doi: 10.1016/j.bbrc.2019.06.123. [PMID: 31255282]
  • Kwang-Youn Kim, Kwang-Il Park, Seul Gi Lee, Su Youn Baek, Eun Hye Lee, Sang Chan Kim, Sang-Hun Kim, Sul-Gi Park, Sun-Nyoung Yu, Tae Woo Oh, Joung-Hee Kim, Keuk-Jun Kim, Soon-Cheol Ahn, Young Woo Kim. Deoxypodophyllotoxin in Anthriscus sylvestris alleviates fat accumulation in the liver via AMP-activated protein kinase, impeding SREBP-1c signal. Chemico-biological interactions. 2018 Oct; 294(?):151-157. doi: 10.1016/j.cbi.2018.08.025. [PMID: 30148990]
  • Liliana Lalaleo, Pilar Testillano, Maria-Carmen Risueño, Rosa M Cusidó, Javier Palazon, Ruben Alcazar, Mercedes Bonfill. Effect of in vitro morphogenesis on the production of podophyllotoxin derivatives in callus cultures of Linum album. Journal of plant physiology. 2018 Sep; 228(?):47-58. doi: 10.1016/j.jplph.2018.05.007. [PMID: 29852334]
  • Yang Chen, Kaijing Zhao, Fei Liu, Ying Li, Zeyu Zhong, Shijin Hong, Xiaodong Liu, Li Liu. Predicting Antitumor Effect of Deoxypodophyllotoxin in NCI-H460 Tumor-Bearing Mice on the Basis of In Vitro Pharmacodynamics and a Physiologically Based Pharmacokinetic-Pharmacodynamic Model. Drug metabolism and disposition: the biological fate of chemicals. 2018 06; 46(6):897-907. doi: 10.1124/dmd.117.079830. [PMID: 29618575]
  • Ying-Lan Yu, Ya-Nan Li, Yong Zhang, Ru-Ning Sun, Jia-Sheng Tu, Yan Shen. Optimization and characterization of deoxypodophyllotoxin loaded mPEG-PDLLA micelles by central composite design with response surface methodology. Chinese journal of natural medicines. 2018 Jun; 16(6):471-480. doi: 10.1016/s1875-5364(18)30081-5. [PMID: 30047469]
  • Xiaojie Zang, Guangji Wang, Qingyun Cai, Xiao Zheng, Jingwei Zhang, Qianying Chen, Baojin Wu, Xiong Zhu, Haiping Hao, Fang Zhou. A Promising Microtubule Inhibitor Deoxypodophyllotoxin Exhibits Better Efficacy to Multidrug-Resistant Breast Cancer than Paclitaxel via Avoiding Efflux Transport. Drug metabolism and disposition: the biological fate of chemicals. 2018 05; 46(5):542-551. doi: 10.1124/dmd.117.079442. [PMID: 29523600]
  • Christel L C Seegers, Pieter G Tepper, Rita Setroikromo, Wim J Quax. Cytotoxic Deoxypodophyllotoxin Can Be Extracted in High Purity from Anthriscus sylvestris Roots by Supercritical Carbon Dioxide. Planta medica. 2018 May; 84(8):544-550. doi: 10.1055/s-0043-123938. [PMID: 29253908]
  • Joël Doussot, Véronique Mathieu, Cyril Colas, Roland Molinié, Cyrielle Corbin, Josiane Montguillon, Laeticia Moreno Y Banuls, Sullivan Renouard, Frédéric Lamblin, Patricia Dupré, Benoit Maunit, Robert Kiss, Christophe Hano, Eric Lainé. Investigation of the Lignan Content in Extracts from Linum, Callitris and Juniperus Species in Relation to Their In Vitro Antiproliferative Activities. Planta medica. 2017 Apr; 83(6):574-581. doi: 10.1055/s-0042-118650. [PMID: 27776375]
  • Wei Zhao, Chen Zhou, Ze-Yuan Guan, Ping Yin, Fusheng Chen, Ya-Jie Tang. Structural Insights into the Inhibition of Tubulin by the Antitumor Agent 4β-(1,2,4-triazol-3-ylthio)-4-deoxypodophyllotoxin. ACS chemical biology. 2017 03; 12(3):746-752. doi: 10.1021/acschembio.6b00842. [PMID: 28035796]
  • Yutong Wang, Liping Huang, Yan Shen, Lidan Tang, Runing Sun, Di Shi, Thomas J Webster, Jiasheng Tu, Chunmeng Sun. Electrostatic interactions between polyglutamic acid and polylysine yields stable polyion complex micelles for deoxypodophyllotoxin delivery. International journal of nanomedicine. 2017; 12(?):7963-7977. doi: 10.2147/ijn.s140573. [PMID: 29133981]
  • George R Pettit, Justin D Searcy, Rui Tan, Gordon M Cragg, Noeleen Melody, John C Knight, Jean-Charles Chapuis. Antineoplastic Agents. 585. Isolation of Bridelia ferruginea Anticancer Podophyllotoxins and Synthesis of 4-Aza-podophyllotoxin Structural Modifications. Journal of natural products. 2016 Mar; 79(3):507-18. doi: 10.1021/acs.jnatprod.5b00873. [PMID: 26938998]
  • Xiong Zhu, Junjie Fu, Yan Tang, Yuan Gao, Shijin Zhang, Qinglong Guo. Design and synthesis of novel 4'-demethyl-4-deoxypodophyllotoxin derivatives as potential anticancer agents. Bioorganic & medicinal chemistry letters. 2016 Feb; 26(4):1360-4. doi: 10.1016/j.bmcl.2015.06.089. [PMID: 26804229]
  • Ling Hui, Chunyan Sang, Donghong Wang, Xiaohui Wang, Meiliang Wang, Qinghua Jia, Mingren Ma, Shiwu Chen. Newly synthesized podophyllotoxin derivative, LJ12, induces apoptosis and mitotic catastrophe in non-small cell lung cancer cells in vitro. Molecular medicine reports. 2016 Jan; 13(1):339-46. doi: 10.3892/mmr.2015.4561. [PMID: 26573436]
  • Yurong Wang, Bin Wang, Mounia Guerram, Li Sun, Wei Shi, Chongchong Tian, Xiong Zhu, Zhenzhou Jiang, Luyong Zhang. Deoxypodophyllotoxin suppresses tumor vasculature in HUVECs by promoting cytoskeleton remodeling through LKB1-AMPK dependent Rho A activatio. Oncotarget. 2015 Oct; 6(30):29497-512. doi: 10.18632/oncotarget.4985. [PMID: 26470595]
  • Luyen Huynh Cong, Rebecca Dauwe, Michelle Lequart, Sophie Vinchon, Sullivan Renouard, Ophélie Fliniaux, Cyril Colas, Cyrielle Corbin, Joël Doussot, Christophe Hano, Frédéric Lamblin, Roland Molinié, Serge Pilard, Nathalie Jullian, Michèle Boitel, Eric Gontier, François Mesnard, Jean-Claude Laberche. Kinetics of glucosylated and non-glucosylated aryltetralin lignans in Linum hairy root cultures. Phytochemistry. 2015 Jul; 115(?):70-8. doi: 10.1016/j.phytochem.2015.01.001. [PMID: 25698360]
  • Marek Och, Anna Och, Łukasz Cieśla, Tomasz Kubrak, Łukasz Pecio, Anna Stochmal, Janusz Kocki, Anna Bogucka-Kocka. Study of cytotoxic activity, podophyllotoxin, and deoxypodophyllotoxin content in selected Juniperus species cultivated in Poland. Pharmaceutical biology. 2015 Jun; 53(6):831-7. doi: 10.3109/13880209.2014.943246. [PMID: 25720974]
  • Yan-Jun Sun, Yan-Li Zhang, Yu Wang, Jun-Min Wang, Xuan Zhao, Jian-Hong Gong, Wei Gao, Yan-Bin Guan. Purity Assessment of Aryltetralin Lactone Lignans by Quantitative 1H Nuclear Magnetic Resonance. Molecules (Basel, Switzerland). 2015 May; 20(6):9671-85. doi: 10.3390/molecules20069671. [PMID: 26016553]
  • Mounia Guerram, Zhen-Zhou Jiang, Lixin Sun, Xiong Zhu, Lu-Yong Zhang. Antineoplastic effects of deoxypodophyllotoxin, a potent cytotoxic agent of plant origin, on glioblastoma U-87 MG and SF126 cells. Pharmacological reports : PR. 2015 Apr; 67(2):245-52. doi: 10.1016/j.pharep.2014.10.003. [PMID: 25712646]
  • Sami Benzina, Jason Harquail, Stephanie Jean, Annie-Pier Beauregard, Caitlyn D Colquhoun, Madison Carroll, Allyson Bos, Christopher A Gray, Gilles A Robichaud. Deoxypodophyllotoxin isolated from Juniperus communis induces apoptosis in breast cancer cells. Anti-cancer agents in medicinal chemistry. 2015; 15(1):79-88. doi: 10.2174/1871520614666140608150448. [PMID: 24913660]
  • Chao-Yun Wang, Xian-Yong Bai, Chun-Hua Wang. Traditional Chinese medicine: a treasured natural resource of anticancer drug research and development. The American journal of Chinese medicine. 2014; 42(3):543-59. doi: 10.1142/s0192415x14500359. [PMID: 24871650]
  • Yang Yang, Yang Chen, Ze-Yu Zhong, Ji Zhang, Feng Li, Ling-Ling Jia, Li Liu, Xiong Zhu, Xiao-Dong Liu. Validated LC-MS/MS assay for quantitative determination of deoxypodophyllotoxin in rat plasma and its application in pharmacokinetic study. Journal of pharmaceutical and biomedical analysis. 2014 Jan; 88(?):410-5. doi: 10.1016/j.jpba.2013.09.027. [PMID: 24176745]
  • Meijuan Wu, Zhenzhou Jiang, Huaqin Duan, Lixin Sun, Shuang Zhang, Mi Chen, Yun Wang, Qin Gao, Yuming Song, Xiong Zhu, Luyong Zhang. Deoxypodophyllotoxin triggers necroptosis in human non-small cell lung cancer NCI-H460 cells. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2013 Oct; 67(8):701-6. doi: 10.1016/j.biopha.2013.06.002. [PMID: 23896261]
  • Meng Fei Li, Wei Li, De Long Yang, Lan Lan Zhou, Tian Tian Li, Xiao Meng Su. Relationship between podophyllotoxin accumulation and soil nutrients and the influence of Fe2+ and Mn2+ on podophyllotoxin biosynthesis in Podophyllum hexandrum tissue culture. Plant physiology and biochemistry : PPB. 2013 Oct; 71(?):96-102. doi: 10.1016/j.plaphy.2013.07.001. [PMID: 23906505]
  • Meyada Khaled, Zhen-Zhou Jiang, Lu-Yong Zhang. Deoxypodophyllotoxin: a promising therapeutic agent from herbal medicine. Journal of ethnopharmacology. 2013 Aug; 149(1):24-34. doi: 10.1016/j.jep.2013.06.021. [PMID: 23792585]
  • Estela Guerrero, Andrés Abad, Gisela Montenegro, Esther Del Olmo, José Luis López-Pérez, Arturo San Feliciano. Analgesic and anti-inflammatory activity of podophyllotoxin derivatives. Pharmaceutical biology. 2013 May; 51(5):566-72. doi: 10.3109/13880209.2012.749921. [PMID: 23363067]
  • Gang Feng, Jing Zhang, Liu Yang, Ying-Qian Liu, Zhi-Wei Zhang, Xuan Tian, Qi-An Jin, Zheng-Qiang Peng. Antifeedant activity of spin-labeled derivatives of deoxypodophyllotoxin against Brontispa longissima larvae. Natural product communications. 2013 Feb; 8(2):199-202. doi: ". [PMID: 23513728]
  • Caitlyn D Carpenter, Taryn O'Neill, Nadia Picot, John A Johnson, Gilles A Robichaud, Duncan Webster, Christopher A Gray. Anti-mycobacterial natural products from the Canadian medicinal plant Juniperus communis. Journal of ethnopharmacology. 2012 Sep; 143(2):695-700. doi: 10.1016/j.jep.2012.07.035. [PMID: 22877928]
  • René Velázquez-Jiménez, J Martín Torres-Valencia, Carlos M Cerda-García-Rojas, Juan D Hernández-Hernández, Luisa U Román-Marín, J Jesús Manríquez-Torres, Mario A Gómez-Hurtado, Alejandro Valdez-Calderón, Virginia Motilva, Sofía García-Mauriño, Elena Talero, Javier Avila, Pedro Joseph-Nathan. Absolute configuration of podophyllotoxin related lignans from Bursera fagaroides using vibrational circular dichroism. Phytochemistry. 2011 Dec; 72(17):2237-43. doi: 10.1016/j.phytochem.2011.07.017. [PMID: 21840559]
  • Oktavia Hendrawati, Herman J Woerdenbag, Paul J A Michiels, Herald G Aantjes, Annie van Dam, Oliver Kayser. Identification of lignans and related compounds in Anthriscus sylvestris by LC-ESI-MS/MS and LC-SPE-NMR. Phytochemistry. 2011 Dec; 72(17):2172-9. doi: 10.1016/j.phytochem.2011.08.009. [PMID: 21889175]
  • Oktavia Hendrawati, Herman J Woerdenbag, Jacques Hille, Wim J Quax, Oliver Kayser. Seasonal variations in the deoxypodophyllotoxin content and yield of Anthriscus sylvestris L. (Hoffm.) grown in the field and under controlled conditions. Journal of agricultural and food chemistry. 2011 Aug; 59(15):8132-9. doi: 10.1021/jf200177q. [PMID: 21604818]
  • Sullivan Renouard, Tatiana Lopez, Oktavia Hendrawati, Patricia Dupre, Joël Doussot, Annie Falguieres, Clotilde Ferroud, Daniel Hagege, Frédéric Lamblin, Eric Laine, Christophe Hano. Podophyllotoxin and deoxypodophyllotoxin in Juniperus bermudiana and 12 other Juniperus species: optimization of extraction, method validation, and quantification. Journal of agricultural and food chemistry. 2011 Aug; 59(15):8101-7. doi: 10.1021/jf201410p. [PMID: 21702435]
  • Yuko Rönquist-Nii, Staffan Eksborg, Magnus Axelson, Johan Harmenberg, Simon Ekman, Michael Bergqvist, Olof Beck. Determination of picropodophyllin and its isomer podophyllotoxin in human serum samples with electrospray ionization of hexylamine adducts by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Feb; 879(5-6):326-34. doi: 10.1016/j.jchromb.2010.12.017. [PMID: 21251888]
  • Peng Xu, Qin Sun, Xijie Wang, Shougang Zhang, Shanshan An, Jie Cheng, Rong Gao, Hang Xiao. Pharmacological effect of deoxypodophyllotoxin: a medicinal agent of plant origin, on mammalian neurons. Neurotoxicology. 2010 Dec; 31(6):680-6. doi: 10.1016/j.neuro.2010.08.002. [PMID: 20705089]
  • Meihua Jin, Eunkyung Lee, Ju Hye Yang, Yue Lu, SangGu Kang, Young-Chae Chang, Seung Ho Lee, Seok-Jong Suh, Cheorl-Ho Kim, Hyeun Wook Chang. Deoxypodophyllotoxin inhibits the expression of intercellular adhesion molecule-1 induced by tumor necrosis factor-alpha in murine lung epithelial cells. Biological & pharmaceutical bulletin. 2010; 33(1):1-5. doi: 10.1248/bpb.33.1. [PMID: 20045926]
  • S Kusari, M Lamshöft, M Spiteller. Aspergillus fumigatus Fresenius, an endophytic fungus from Juniperus communis L. Horstmann as a novel source of the anticancer pro-drug deoxypodophyllotoxin. Journal of applied microbiology. 2009 Sep; 107(3):1019-30. doi: 10.1111/j.1365-2672.2009.04285.x. [PMID: 19486398]
  • Yeonjoong Yong, Soon Young Shin, Young Han Lee, Yoongho Lim. Antitumor activity of deoxypodophyllotoxin isolated from Anthriscus sylvestris: Induction of G2/M cell cycle arrest and caspase-dependent apoptosis. Bioorganic & medicinal chemistry letters. 2009 Aug; 19(15):4367-71. doi: 10.1016/j.bmcl.2009.05.093. [PMID: 19501508]
  • Seok-Jong Suh, Jeong-Ran Kim, Un-Ho Jin, Hong-Seo Choi, Young-Chae Chang, Young-Choon Lee, Sung-Hoon Kim, In-Seon Lee, Tae Chul Moon, Hyeun-Wook Chang, Cheorl-Ho Kim. Deoxypodophyllotoxin, flavolignan, from Anthriscus sylvestris Hoffm. inhibits migration and MMP-9 via MAPK pathways in TNF-alpha-induced HASMC. Vascular pharmacology. 2009 Jul; 51(1):13-20. doi: 10.1016/j.vph.2008.10.004. [PMID: 19013539]
  • Meihua Jin, Tae Chul Moon, Zhejiu Quan, Eunkyung Lee, Yun Kyung Kim, Ju Hae Yang, Seok-Jong Suh, Tae Cheon Jeong, Seung Ho Lee, Cheorl-Ho Kim, Hyeun Wook Chang. The naturally occurring flavolignan, deoxypodophyllotoxin, inhibits lipopolysaccharide-induced iNOS expression through the NF-kappaB activation in RAW264.7 macrophage cells. Biological & pharmaceutical bulletin. 2008 Jul; 31(7):1312-5. doi: 10.1248/bpb.31.1312. [PMID: 18591766]
  • Stefano Dall'Acqua, Michela Giorgetti, Rinaldo Cervellati, Gabbriella Innocenti. Deoxypodophyllotoxin content and antioxidant activity of aerial parts of Anthriscus sylvestris Hoffm. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2006 Sep; 61(9-10):658-62. doi: 10.1515/znc-2006-9-1008. [PMID: 17137110]
  • Chang Xin Lin, Eunkyung Lee, Mei Hua Jin, Jumin Yook, Zhejiu Quan, Kyungmi Ha, Tae Chul Moon, Mi Jin Kim, Keuk Jun Kim, Seung Ho Lee, Hyeun Wook Chang. Deoxypodophyllotoxin (DPT) inhibits eosinophil recruitment into the airway and Th2 cytokine expression in an OVA-induced lung inflammation. Planta medica. 2006 Jul; 72(9):786-91. doi: 10.1055/s-2006-931607. [PMID: 16732515]
  • Seung Ho Lee, Min Jung Son, Hye Kyung Ju, Chang Xiu Lin, Tae Chul Moon, Han-Gon Choi, Jong Keun Son, Hyeun Wook Chang. Dual inhibition of cyclooxygenases-2 and 5-lipoxygenase by deoxypodophyllotoxin in mouse bone marrow-derived mast cells. Biological & pharmaceutical bulletin. 2004 Jun; 27(6):786-8. doi: 10.1248/bpb.27.786. [PMID: 15187418]
  • Chang Xiu Lin, Min Jung Son, Hye Kyung Ju, Tae Chul Moon, Eunkyung Lee, So Hee Kim, Mi-Jeong Kim, Jong Keun Son, Seung Ho Lee, Hyeun Wook Chang. Deoxypodophyllotoxin, a naturally occurring lignan, inhibits the passive cutaneous anaphylaxis reaction. Planta medica. 2004 May; 70(5):474-6. doi: 10.1055/s-2004-818981. [PMID: 15124098]
  • Hyunjung Choi, Jeongho Lee, Hyun-Jung Shin, Byeong-Gon Lee, Ihseop Chang, Jae-Sung Hwang. Deoxypodophyllotoxin reduces skin pigmentation of brown Guinea pigs. Planta medica. 2004 Apr; 70(4):378-80. doi: 10.1055/s-2004-818955. [PMID: 15095159]
  • Toshiya Masuda, Yasuo Oyama, Shigetomo Yonemori, Yoshio Takeda, Yuko Yamazaki, Shinichi Mizuguchi, Mami Nakata, Tomochika Tanaka, Lumi Chikahisa, Yuzuru Inaba, Yoshihiko Okada. Flow cytometric estimation on cytotoxic activity of leaf extracts from seashore plants in subtropical Japan: isolation, quantification and cytotoxic action of (-)-deoxypodophyllotoxin. Phytotherapy research : PTR. 2002 Jun; 16(4):353-8. doi: 10.1002/ptr.902. [PMID: 12112292]
  • Yong Kim, Song-Bae Kim, Young-Jae You, Byung-Zun Ahn. Deoxypodophyllotoxin; the cytotoxic and antiangiogenic component from Pulsatilla koreana. Planta medica. 2002 Mar; 68(3):271-4. doi: 10.1055/s-2002-23140. [PMID: 11914969]
  • A Koulman, R Bos, M Medarde, N Pras, W J Quax. A fast and simple GC MS method for lignan profiling in Anthriscus sylvestris and biosynthetically related Plant species. Planta medica. 2001 Dec; 67(9):858-62. doi: 10.1055/s-2001-18849. [PMID: 11745025]
  • H Yamaguchi, M Arimoto, K Yamamoto, A Numata. [Studies on the constituents of the seeds of Hernandia ovigera L. (author's transl)]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 1979 Jun; 99(6):674-7. doi: 10.1248/yakushi1947.99.6_674. [PMID: 231650]