Podofilox (BioDeep_00000407853)

 

Secondary id: BioDeep_00000014667, BioDeep_00000271063, BioDeep_00000860796

natural product PANOMIX_OTCML-2023 Chemicals and Drugs Antibiotics Volatile Flavor Compounds


代谢物信息卡片


Podophyllotoxin

化学式: C22H22O8 (414.1314612)
中文名称: 鬼臼毒素
谱图信息: 最多检出来源 Homo sapiens(blood) 0.05%

分子结构信息

SMILES: COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O
InChI: InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1

描述信息

D - Dermatologicals > D06 - Antibiotics and chemotherapeutics for dermatological use > D06B - Chemotherapeutics for topical use > D06BB - Antivirals
C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor
C274 - Antineoplastic Agent > C1931 - Antineoplastic Plant Product > C1331 - Epipodophyllotoxin Compound
C471 - Enzyme Inhibitor > C129825 - Antineoplastic Enzyme Inhibitor > C1748 - Topoisomerase Inhibitor
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C273 - Antimitotic Agent
D050258 - Mitosis Modulators > D050256 - Antimitotic Agents > D050257 - Tubulin Modulators
D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents
D003879 - Dermatologic Agents > D007641 - Keratolytic Agents
C1907 - Drug, Natural Product
Podofilox (Podophyllotoxin) is a potent inhibitor of microtubule assembly and DNA topoisomerase II.
Podofilox (Podophyllotoxin) is a potent inhibitor of microtubule assembly and DNA topoisomerase II.

同义名列表

3 个代谢物同义名

Podophyllotoxin; Podofilox; Podophyllotoxin



数据库引用编号

27 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

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)

150 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。



文献列表

  • Yujin Guo, Beibei Chen, Jinxiu Guo, Pei Jiang, Jianhua Wang, Wenxue Sun. Design, synthesis and biological evaluation of novel podophyllotoxin derivatives as tubulin-targeting anticancer agents. Pharmaceutical biology. 2024 Dec; 62(1):233-249. doi: 10.1080/13880209.2024.2318350. [PMID: 38393642]
  • Meng Hao, Hui Xu. Chemistry and Biology of Podophyllotoxins: An Update. Chemistry (Weinheim an der Bergstrasse, Germany). 2024 Jan; 30(4):e202302595. doi: 10.1002/chem.202302595. [PMID: 37814110]
  • Jiajia Duan, Jiaxing Sun, Tao Jiang, Xiao Ma, Xuejiao Li, Yuming Wang, Fangfang Zhang, Chuanxin Liu. Podophyllotoxin-mediated neurotoxicity via the microbiota-gut-brain axis in SD rats based on the toxicological evidence chain (TEC) concept. The Science of the total environment. 2024 Jan; 907(?):168106. doi: 10.1016/j.scitotenv.2023.168106. [PMID: 37884145]
  • Mona Soltani, Reza Fotovat, Mohsen Sharifi, Najmeh Ahmadian Chashmi, Mehrdad Behmanesh. In Vitro Comparative Study on Antineoplastic Effects of Pinoresinol and Lariciresinol on Healthy Cells and Breast Cancer-Derived Human Cells. Iranian journal of medical sciences. 2024 Jan; 49(1):30-39. doi: 10.30476/ijms.2023.94805.2611. [PMID: 38322161]
  • Hyun-Ju Yu, Ji-Ae Shin, Su-Jung Choi, Sung-Dae Cho. Podophyllotoxin reduces the aggressiveness of human oral squamous cell carcinoma through myeloid cell leukemia‑1. International journal of molecular medicine. 2023 Nov; 52(5):. doi: 10.3892/ijmm.2023.5306. [PMID: 37711052]
  • 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]
  • Jiao Kong, Hongqian Kui, Yue Tian, Xianbin Kong, Tao He, Qingbo Li, Chunyu Gu, Jinhe Guo, Chuanxin Liu. Nephrotoxicity assessment of podophyllotoxin-induced rats by regulating PI3K/Akt/mTOR-Nrf2/HO1 pathway in view of toxicological evidence chain (TEC) concept. Ecotoxicology and environmental safety. 2023 Oct; 264(?):115392. doi: 10.1016/j.ecoenv.2023.115392. [PMID: 37651795]
  • Giang Thu Nguyen, Ha Thi Hong Nguyen, Hoa Thi Tran, Huyen Thi Tran, Anh Ngoc Ho, Quang Ho Tran, Ngoc Bich Pham. Enhanced podophyllotoxin production of endophyte Fusarium proliferatum TQN5T by host extract and phenylalanine. Applied microbiology and biotechnology. 2023 Sep; 107(17):5367-5378. doi: 10.1007/s00253-023-12659-1. [PMID: 37436482]
  • Di Hu, Xiaowei Luo, Yuxian Wang, Ming Gong, Zhurong Zou. [Gene cloning and enzymatic activity analysis of phenylalanine ammonia-lyase from Sinopodophyllum hexandrum (Royle) Ying]. Sheng wu gong cheng xue bao = Chinese journal of biotechnology. 2023 Jul; 39(7):2818-2838. doi: 10.13345/j.cjb.230076. [PMID: 37584134]
  • Zahra Danaeipour, Ghasemali Garoosi, Masoud Tohidfar, Mohammad Reza Bakhtiarizadeh, Mohammad Hossein Mirjalili. Comprehensive RNA-Seq-based study and metabolite profiling to identify genes involved in podophyllotoxin biosynthesis in Linum album Kotschy ex Boiss. (Linaceae). Scientific reports. 2023 06; 13(1):9219. doi: 10.1038/s41598-023-36102-7. [PMID: 37286620]
  • Mostafa Sagharyan, Mohsen Sharifi, Elaheh Samari. Methyl jasmonate redirects the dynamics of carbohydrates and amino acids toward the lignans accumulation in Linum album cells. Plant physiology and biochemistry : PPB. 2023 May; 198(?):107677. doi: 10.1016/j.plaphy.2023.107677. [PMID: 37086692]
  • Jun Li, Nasir Tajuddeen, Doris Feineis, Virima Mudogo, Marcel Kaiser, Ean-Jeong Seo, Thomas Efferth, Gerhard Bringmann. Jozibrevine D from Ancistrocladus ileboensis, the fifth alkaloid in a series of six possible atropo-diastereomeric naphthylisoquinoline dimers, showing antiparasitic and antileukemic activities. Bioorganic & medicinal chemistry letters. 2023 Apr; 86(?):129258. doi: 10.1016/j.bmcl.2023.129258. [PMID: 36972793]
  • Jing Hu, Jiali Wu, Qihuang Jin, Ling Zhang, Ning Shen, Yiyang Shu, Lu Cheng, Jian Zhang, Guangyi Hu, Kangjia Lv, Qizhi Jian, Hui Chen, Fang Zhang, Xiaodong Sun. Repurposing picropodophyllin as a potential thyroid eye disease treatment via delaying mitotic clonal expansion through a patient-derived preclinical platform. Clinical and translational medicine. 2023 04; 13(4):e1218. doi: 10.1002/ctm2.1218. [PMID: 37012693]
  • Shenghu Guo, Yuchao Chen, Yongxing Zhu, Mei Tian. Transcriptome analysis reveals differentially expressed genes involved in somatic embryogenesis and podophyllotoxin biosynthesis of Sinopodophyllum hexandrum (Royle) T. S. Ying. Protoplasma. 2023 Feb; ?(?):. doi: 10.1007/s00709-023-01843-9. [PMID: 36840780]
  • Sara Motyka, Karolina Jafernik, Halina Ekiert, Javad Sharifi-Rad, Daniela Calina, Basem Al-Omari, Agnieszka Szopa, William C Cho. Podophyllotoxin and its derivatives: Potential anticancer agents of natural origin in cancer chemotherapy. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Feb; 158(?):114145. doi: 10.1016/j.biopha.2022.114145. [PMID: 36586242]
  • Yi-Fong Chen, Bashir Lawal, Li-Jiau Huang, Sheng-Chu Kuo, Maryam Rachmawati Sumitra, Ntlotlang Mokgautsi, Hung-Yun Lin, Hsu-Shan Huang. In Vitro and In Silico Biological Studies of 4-Phenyl-2-quinolone (4-PQ) Derivatives as Anticancer Agents. Molecules (Basel, Switzerland). 2023 Jan; 28(2):. doi: 10.3390/molecules28020555. [PMID: 36677621]
  • Lu Jin, Zhijun Song, Fang Cai, Lijun Ruan, Renwang Jiang. Chemistry and Biological Activities of Naturally Occurring and Structurally Modified Podophyllotoxins. Molecules (Basel, Switzerland). 2022 Dec; 28(1):. doi: 10.3390/molecules28010302. [PMID: 36615496]
  • Siyu Shen, Yuru Tong, Yunfeng Luo, Luqi Huang, Wei Gao. Biosynthesis, total synthesis, and pharmacological activities of aryltetralin-type lignan podophyllotoxin and its derivatives. Natural product reports. 2022 09; 39(9):1856-1875. doi: 10.1039/d2np00028h. [PMID: 35913409]
  • Shengnan Xu, Xinru Li, Shi Liu, Peilin Tian, Dengwu Li. Juniperus sabina L. as a Source of Podophyllotoxins: Extraction Optimization and Anticholinesterase Activities. International journal of molecular sciences. 2022 Sep; 23(18):. doi: 10.3390/ijms231810205. [PMID: 36142118]
  • Ying-Lian Song, Shuai-Shuai Liu, Jie Yang, Jiao Xie, Xiang Zhou, Zhi-Bing Wu, Li-Wei Liu, Pei-Yi Wang, Song Yang. Discovery of Epipodophyllotoxin-Derived B2 as Promising XooFtsZ Inhibitor for Controlling Bacterial Cell Division: Structure-Based Virtual Screening, Synthesis, and SAR Study. International journal of molecular sciences. 2022 Aug; 23(16):. doi: 10.3390/ijms23169119. [PMID: 36012385]
  • Xin Zhang, Tingting Yang, Xin Jin, Kaige Lin, Xiling Dai, Ting Gao, Guozheng Huang, Minghui Fan, Liang Ma, Zi Liu, Jianguo Cao. Synthesis and biological evaluation of cytotoxic activity of novel podophyllotoxin derivatives incorporating piperazinyl-cinnamic amide moieties. Bioorganic chemistry. 2022 06; 123(?):105761. doi: 10.1016/j.bioorg.2022.105761. [PMID: 35358823]
  • Kishor Mazumder, Asma Aktar, Priyanka Roy, Biswajit Biswas, Md Emran Hossain, Kishore Kumar Sarkar, Sitesh Chandra Bachar, Firoj Ahmed, A S M Monjur-Al-Hossain, Koichi Fukase. A Review on Mechanistic Insight of Plant Derived Anticancer Bioactive Phytocompounds and Their Structure Activity Relationship. Molecules (Basel, Switzerland). 2022 May; 27(9):. doi: 10.3390/molecules27093036. [PMID: 35566385]
  • Rui Wang, Yinan Zhao, Zhenlong Huang, Yaxin Zhou, Wei Wang, Yang Xuan, Yuhong Zhen, Benzhi Ju, Shutao Guo, Shubiao Zhang. Self-Assembly of Podophyllotoxin-Loaded Lipid Bilayer Nanoparticles for Highly Effective Chemotherapy and Immunotherapy via Downregulation of Programmed Cell Death Ligand 1 Production. ACS nano. 2022 03; 16(3):3943-3954. doi: 10.1021/acsnano.1c09391. [PMID: 35166522]
  • Jiao Kong, Tao He, Chuanxin Liu, Jianmei Huang. Multi modular toxicity assessment of nephrotoxicity in podophyllotoxin exposure rats on account of toxicological evidence chain (TEC) concept. Ecotoxicology and environmental safety. 2022 Feb; 231(?):113157. doi: 10.1016/j.ecoenv.2021.113157. [PMID: 35026582]
  • Qianqian Zhang, Xuemei Li, Xiaoxin Gao, Chunran Cao, Yuchi Hu, Hongzhu Guo. Total saponins from stems and leaves of Panax quinquefolius L. ameliorate podophyllotoxin-induced myelosuppression and gastrointestinal toxicity. Biomedical chromatography : BMC. 2022 Feb; 36(2):e5266. doi: 10.1002/bmc.5266. [PMID: 34648200]
  • 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]
  • Akihito Yokosuka, Chiaki Yamada, Makoto Saito, Shohei Yokogawa, Yoshihiro Mimaki. Chemical Constituents of the Leaves of Thujopsis dolabrata and Their Cytotoxicity. Chemical & pharmaceutical bulletin. 2022; 70(10):720-725. doi: 10.1248/cpb.c22-00286. [PMID: 36184455]
  • Xuejie Zhu, Xiaojie Chen, Guoli Wang, Dan Lei, Xiaoyu Chen, Kehao Lin, Minjing Li, Haiyan Lin, Defang Li, Qiusheng Zheng. Picropodophyllin Inhibits the Proliferation of Human Prostate Cancer DU145 and LNCaP Cells via ROS Production and PI3K/AKT Pathway Inhibition. Biological & pharmaceutical bulletin. 2022; 45(8):1027-1035. doi: 10.1248/bpb.b21-01006. [PMID: 35908886]
  • Dejan Orčić, Sanja Berežni, Dušan Škorić, Neda Mimica-Dukić. Comprehensive study of Anthriscus sylvestris lignans. Phytochemistry. 2021 Dec; 192(?):112958. doi: 10.1016/j.phytochem.2021.112958. [PMID: 34560578]
  • Verónica Rodríguez-López, César Millán-Pacheco, Judith González-Christen, Maricruz Anaya-Ruíz, Omar Aristeo Peña-Morán. In Vitro Anti-Tubulin Activity on MCF10A Cell Line and In Silico Rigid/Semiflexible-Residues Docking, of Two Lignans from Bursera Fagaroides var. Fagaroides. Molecules (Basel, Switzerland). 2021 Oct; 26(20):. doi: 10.3390/molecules26206155. [PMID: 34684736]
  • 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]
  • Dongxue Sun, Xiaoxia Gao, Qiao Wang, Kristopher W Krausz, Zhongze Fang, Youbo Zhang, Cen Xie, Frank J Gonzalez. Metabolic map of the antiviral drug podophyllotoxin provides insights into hepatotoxicity. Xenobiotica; the fate of foreign compounds in biological systems. 2021 Sep; 51(9):1047-1059. doi: 10.1080/00498254.2021.1961920. [PMID: 34319859]
  • Michela Alfieri, Iride Mascheretti, Roméo A Dougué Kentsop, Roberto Consonni, Franca Locatelli, Monica Mattana, Gianluca Ottolina. Enhanced Aryltetralin Lignans Production in Linum Adventi-Tious Root Cultures. Molecules (Basel, Switzerland). 2021 Aug; 26(17):. doi: 10.3390/molecules26175189. [PMID: 34500623]
  • Diana I Ivanova, Paraskev T Nedialkov, Alexander N Tashev, Marta Olech, Renata Nowak, Yana E Ilieva, Zlatina K Kokanova-Nedialkova, Teodora N Atanasova, George Angelov, Hristo M Najdenski. Junipers of Various Origins as Potential Sources of the Anticancer Drug Precursor Podophyllotoxin. Molecules (Basel, Switzerland). 2021 Aug; 26(17):. doi: 10.3390/molecules26175179. [PMID: 34500615]
  • Yuanyuan Zhang, Min Lv, Hui Xu. Insecticidal activity of twin compounds from podophyllotoxin and cytisine. Bioorganic & medicinal chemistry letters. 2021 07; 43(?):128104. doi: 10.1016/j.bmcl.2021.128104. [PMID: 33984477]
  • Zhen Meng, Tingting Yao, Wei Zhao, Hongmei Li, Ya-Jie Tang. [Research progress in biosynthesis of podophyllotoxin and its derivatives]. Sheng wu gong cheng xue bao = Chinese journal of biotechnology. 2021 Jun; 37(6):2026-2038. doi: 10.13345/j.cjb.210258. [PMID: 34227292]
  • Valtcho D Zheljazkov, Charles L Cantrell, Ivanka Semerdjieva, Tzenka Radoukova, Albena Stoyanova, Vasilina Maneva, Miroslava Kačániová, Tess Astatkie, Daniela Borisova, Ivayla Dincheva, Ivan Salamon. Essential Oil Composition and Bioactivity of Two Juniper Species from Bulgaria and Slovakia. Molecules (Basel, Switzerland). 2021 Jun; 26(12):. doi: 10.3390/molecules26123659. [PMID: 34203980]
  • M Lv, H-Y Su, M-L Li, D-L Yang, R-Y Yao, M-F Li, J-H Wei. Effect of UV-B radiation on growth, flavonoid and podophyllotoxin accumulation, and related gene expression in Sinopodophyllum hexandrum. Plant biology (Stuttgart, Germany). 2021 May; 23 Suppl 1(?):202-209. doi: 10.1111/plb.13226. [PMID: 33280221]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
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