Diphyllin (BioDeep_00000008159)

   

PANOMIX_OTCML-2023 Antitumor activity natural product


代谢物信息卡片


9-(1,3-Benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one; NSC 309691

化学式: C21H16O7 (380.0896)
中文名称: 二叶草素
谱图信息: 最多检出来源 Viridiplantae(plant) 27.53%

分子结构信息

SMILES: COC1=C(C=C2C(=C1)C(=C3C(=C2O)COC3=O)C4=CC5=C(C=C4)OCO5)OC
InChI: InChI=1S/C21H16O7/c1-24-15-6-11-12(7-16(15)25-2)20(22)13-8-26-21(23)19(13)18(11)10-3-4-14-17(5-10)28-9-27-14/h3-7,22H,8-9H2,1-2H3

描述信息

Diphyllin is a lignan.
Diphyllin is a natural product found in Haplophyllum alberti-regelii, Haplophyllum bucharicum, and other organisms with data available.
Origin: Plant
Diphyllin is an arylnaphthalene lignan isolated from Justicia procumbens and is a potent HIV-1 inhibitor with an IC50 of 0.38 μM. Diphyllin is active against vesicular stomatitis virus (VSV) and influenza virus[1]. Diphyllin is a vacuolar type H+-ATPase (V-ATPase) inhibitor with an IC50 value of 17 nM and inhibits lysosomal acidification in human osteoclasts[2]. Diphyllin inhibits NO production with an IC50 of 50 μM and has anticancer and anti-inflammatory activities[3].
Diphyllin is an arylnaphthalene lignan isolated from Justicia procumbens and is a potent HIV-1 inhibitor with an IC50 of 0.38 μM. Diphyllin is active against vesicular stomatitis virus (VSV) and influenza virus[1]. Diphyllin is a vacuolar type H+-ATPase (V-ATPase) inhibitor with an IC50 value of 17 nM and inhibits lysosomal acidification in human osteoclasts[2]. Diphyllin inhibits NO production with an IC50 of 50 μM and has anticancer and anti-inflammatory activities[3].

同义名列表

32 个代谢物同义名

9-(1,3-Benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one; NSC 309691; Naphtho(2,3-c)furan-1(3H)-one, 4-hydroxy-6,7-dimethoxy-9-(3,4-(methylenedioxy)phenyl)-; 4-Hydroxy-6,7-dimethoxy-9-[3,4-(methylenedioxy)phenyl]-naphtho[2,3-c]furan-1(3H)-one; 9-(benzo[d][1,3]dioxol-5-yl)-4-hydroxy-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one; Naphtho[2,3-c]furan-1(3H)-one, 9-(1,3-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-; 9-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-4-oxidanyl-3H-benzo[f][2]benzofuran-1-one; Naphtho(2,3-c)furan-1(3H)-one, 9-(1,3-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-; 9-(1,3-Benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one #; 9-(1,3-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-3H-benzo[f]isobenzofuran-1-one; 9-(1,3-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-3H-benzo[f][2]benzofuran-1-one; 9-(1,3-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-3H-benz[f]isobenzofuran-1-one; 9-(1,3-BENZODIOXOL-5-YL)-4-HYDROXY-6,7-DIMETHOXYNAPHTHO(2,3-C)FURAN-1(3H)-ONE; 9-(1,3-Benzodioxol-5-yl)-6,7-dimethoxy-4-hydroxynaphtho[2,3-c]furan-1(3H)-one; 9-(13-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxynaphtho(2,3-c)furan-1(3H)-one; Diphyllin, >=98\\% (HPLC); UNII-W4PN5LDP26; Oprea1_135417; Oprea1_318204; W4PN5LDP26; Diphyllin; 9-(1,3-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-3H-benzo[f][2]benzoxol-1-one; 9-Benzo[1,3]dioxol-5-yl-4-hydroxy-6,7-dimethoxy-3H-naphtho[2,3-c]furan-1-one; STOCK1N-00276; ZINC00828203; MLS000106853; SMR000111229; BAS 00442101; NSC 309691; 22055-22-7; NSC309691; C10559; Diphyllin



数据库引用编号

26 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

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

  • diphyllin biosynthesis: O2 + a reduced [NADPH-hemoprotein reductase] + justicidin B ⟶ H2O + an oxidized [NADPH-hemoprotein reductase] + diphyllin

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

  • diphyllin biosynthesis: O2 + a reduced [NADPH-hemoprotein reductase] + justicidin B ⟶ H2O + an oxidized [NADPH-hemoprotein reductase] + diphyllin

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

85 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 15 ANXA5, BCL2, CASP3, CCND1, CDK4, CNR2, CTNNB1, LAMP1, MTOR, MYC, NLRP3, PGP, PTGS2, TNFSF11, TUBB4B
Peripheral membrane protein 3 ANXA5, MTOR, PTGS2
Endosome membrane 2 CD14, LAMP1
Endoplasmic reticulum membrane 3 BCL2, MTOR, PTGS2
Nucleus 9 BCL2, CASP3, CCND1, CDK4, CTNNB1, MTOR, MYC, NLRP3, TUBB4B
cytosol 11 ACP5, ANXA5, BCL2, CASP3, CCND1, CDK4, CTNNB1, LAMP1, MTOR, NLRP3, TUBB4B
dendrite 2 CNR2, MTOR
phagocytic vesicle 1 MTOR
centrosome 2 CCND1, CTNNB1
nucleoplasm 7 ATP2B1, CASP3, CCND1, CDK4, CTNNB1, MTOR, MYC
Cell membrane 6 ATP2B1, CD14, CTNNB1, IFNAR1, LAMP1, TNFSF11
Cytoplasmic side 1 MTOR
lamellipodium 1 CTNNB1
Multi-pass membrane protein 1 ATP2B1
Golgi apparatus membrane 2 MTOR, NLRP3
Synapse 2 ATP2B1, CTNNB1
cell cortex 1 CTNNB1
cell junction 1 CTNNB1
glutamatergic synapse 3 ATP2B1, CASP3, CTNNB1
Golgi apparatus 1 CD14
Golgi membrane 3 INS, MTOR, NLRP3
lysosomal membrane 2 LAMP1, MTOR
neuronal cell body 1 CASP3
presynaptic membrane 2 ATP2B1, CTNNB1
sarcolemma 2 ANXA5, LAMP1
synaptic vesicle 1 LAMP1
Cytoplasm, cytosol 1 NLRP3
Lysosome 4 ACP5, IFNAR1, LAMP1, MTOR
endosome 1 IFNAR1
plasma membrane 7 ATP2B1, CD14, CNR2, CTNNB1, IFNAR1, LAMP1, TNFSF11
synaptic vesicle membrane 1 ATP2B1
Membrane 10 ACP5, ANXA5, ATP2B1, BCL2, CTNNB1, LAMP1, MTOR, MYC, NLRP3, TNFSF11
basolateral plasma membrane 2 ATP2B1, CTNNB1
caveola 1 PTGS2
extracellular exosome 6 ANXA5, ATP2B1, CD14, CTNNB1, LAMP1, TUBB4B
Lysosome membrane 2 LAMP1, MTOR
endoplasmic reticulum 4 BCL2, CNR2, NLRP3, PTGS2
extracellular space 3 CD14, INS, TNFSF11
perinuclear region of cytoplasm 2 CTNNB1, LAMP1
Schaffer collateral - CA1 synapse 1 CTNNB1
adherens junction 1 CTNNB1
apicolateral plasma membrane 1 CTNNB1
bicellular tight junction 3 CCND1, CDK4, CTNNB1
mitochondrion 2 BCL2, NLRP3
protein-containing complex 4 BCL2, CTNNB1, MYC, PTGS2
intracellular membrane-bounded organelle 1 ATP2B1
Microsome membrane 2 MTOR, PTGS2
postsynaptic density 1 CASP3
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 2 IFNAR1, LAMP1
Secreted 4 CD14, INS, NLRP3, TNFSF11
extracellular region 6 ANXA5, CD14, INS, NLRP3, TNFSF11, TUBB4B
Mitochondrion outer membrane 2 BCL2, MTOR
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, MTOR
transcription regulator complex 2 CDK4, CTNNB1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
Nucleus membrane 3 BCL2, CCND1, CDK4
Bcl-2 family protein complex 1 BCL2
nuclear membrane 3 BCL2, CCND1, CDK4
external side of plasma membrane 3 ANXA5, CD14, LAMP1
Extracellular vesicle 1 TUBB4B
multivesicular body 1 LAMP1
perikaryon 1 CNR2
Z disc 1 CTNNB1
beta-catenin destruction complex 1 CTNNB1
microtubule cytoskeleton 1 TUBB4B
nucleolus 2 CDK4, MYC
Wnt signalosome 1 CTNNB1
apical part of cell 1 CTNNB1
cell-cell junction 1 CTNNB1
Single-pass type II membrane protein 1 TNFSF11
postsynaptic membrane 2 CNR2, CTNNB1
Membrane raft 1 CD14
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
Nucleus, PML body 1 MTOR
PML body 1 MTOR
collagen-containing extracellular matrix 1 ANXA5
fascia adherens 1 CTNNB1
lateral plasma membrane 2 ATP2B1, CTNNB1
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 1 NLRP3
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Late endosome 2 IFNAR1, LAMP1
Zymogen granule membrane 1 ANXA5
neuron projection 1 PTGS2
chromatin 2 CDK4, MYC
Late endosome membrane 1 LAMP1
autophagosome membrane 1 LAMP1
cell projection 1 ATP2B1
cell periphery 1 CTNNB1
mitotic spindle 1 TUBB4B
cytoskeleton 1 TUBB4B
Cytoplasm, cytoskeleton, cilium basal body 1 CTNNB1
Nucleus, nucleolus 1 MYC
spindle pole 1 CTNNB1
postsynaptic density, intracellular component 1 CTNNB1
Basolateral cell membrane 1 ATP2B1
Lipid-anchor, GPI-anchor 1 CD14
microvillus membrane 1 CTNNB1
intercellular bridge 1 TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
nuclear envelope 2 MTOR, MYC
Endomembrane system 3 CTNNB1, MTOR, NLRP3
endosome lumen 1 INS
axonemal microtubule 1 TUBB4B
microtubule organizing center 1 NLRP3
Nucleus, nucleoplasm 1 MYC
Cell projection, dendrite 1 CNR2
Melanosome 1 LAMP1
euchromatin 1 CTNNB1
Presynaptic cell membrane 1 ATP2B1
side of membrane 1 CD14
myelin sheath 1 BCL2
lipopolysaccharide receptor complex 1 CD14
secretory granule lumen 1 INS
secretory granule membrane 1 CD14
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 INS, PTGS2
transcription repressor complex 1 CCND1
transport vesicle 1 INS
azurophil granule membrane 1 LAMP1
RNA polymerase II transcription repressor complex 1 MYC
beta-catenin-TCF complex 1 CTNNB1
azurophil granule lumen 1 TUBB4B
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
immunological synapse 1 ATP2B1
[Isoform 2]: Cytoplasm 1 TNFSF11
[Tumor necrosis factor ligand superfamily member 11, soluble form]: Secreted 1 TNFSF11
presynaptic active zone cytoplasmic component 1 CTNNB1
vesicle membrane 1 ANXA5
extrinsic component of cytoplasmic side of plasma membrane 1 CNR2
protein-DNA complex 1 CTNNB1
ficolin-1-rich granule membrane 1 LAMP1
death-inducing signaling complex 1 CASP3
[Isoform 1]: Cell membrane 1 IFNAR1
Rough endoplasmic reticulum 1 MYC
Cytoplasmic vesicle, phagosome 1 MTOR
catenin complex 1 CTNNB1
cyclin-dependent protein kinase holoenzyme complex 2 CCND1, CDK4
Myc-Max complex 1 MYC
Autolysosome 1 LAMP1
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
photoreceptor ribbon synapse 1 ATP2B1
Cytolytic granule membrane 1 LAMP1
phagolysosome membrane 1 LAMP1
cyclin D1-CDK4 complex 2 CCND1, CDK4
cyclin D2-CDK4 complex 1 CDK4
cyclin D3-CDK4 complex 1 CDK4
beta-catenin-TCF7L2 complex 1 CTNNB1
cyclin D1-CDK6 complex 1 CCND1
beta-catenin-ICAT complex 1 CTNNB1
Scrib-APC-beta-catenin complex 1 CTNNB1
nucleoplasmic reticulum 1 MYC


文献列表

  • Heba A S El-Nashar, Ahmed M Sayed, Hany A M El-Sherief, Mostafa E Rateb, Lina Akil, Ibrahim Khadra, Taghreed A Majrashi, Sara T Al-Rashood, Faizah A Binjubair, Mahmoud A El Hassab, Wagdy M Eldehna, Usama Ramadan Abdelmohsen, Nada M Mostafa. Metabolomic profile, anti-trypanosomal potential and molecular docking studies of Thunbergia grandifolia. Journal of enzyme inhibition and medicinal chemistry. 2023 Dec; 38(1):2199950. doi: 10.1080/14756366.2023.2199950. [PMID: 37080775]
  • Gergő Tóth, Kata Horváti, Márta Kraszni, Tim Ausbüttel, Bernadett Pályi, Zoltán Kis, Zoltán Mucsi, Gábor M Kovács, Szilvia Bősze, Imre Boldizsár. Arylnaphthalene Lignans with Anti-SARS-CoV-2 and Antiproliferative Activities from the Underground Organs of Linum austriacum and Linum perenne. Journal of natural products. 2023 Mar; ?(?):. doi: 10.1021/acs.jnatprod.2c00580. [PMID: 36857518]
  • Michal Štefánik, Dattatry Shivajirao Bhosale, Jan Haviernik, Petra Straková, Martina Fojtíková, Lucie Dufková, Ivana Huvarová, Jiří Salát, Jan Bartáček, Jan Svoboda, Miloš Sedlák, Daniel Růžek, Andrew D Miller, Luděk Eyer. Diphyllin Shows a Broad-Spectrum Antiviral Activity against Multiple Medically Important Enveloped RNA and DNA Viruses. Viruses. 2022 02; 14(2):. doi: 10.3390/v14020354. [PMID: 35215947]
  • Suman Thamburaj, Elangomathavan Ramaraj, Sivasamy Sethupathy, Chakkaravarthi Kamalanathan, Atchudan Raji, Satish Kumar Rajasekharan. Antibacterial and antibiofilm activities of diphyllin against fish pathogens. Microbial pathogenesis. 2020 Aug; 145(?):104232. doi: 10.1016/j.micpath.2020.104232. [PMID: 32353578]
  • Qinghua Cui, Ruikun Du, Miaomiao Liu, Lijun Rong. Lignans and Their Derivatives from Plants as Antivirals. Molecules (Basel, Switzerland). 2020 Jan; 25(1):. doi: 10.3390/molecules25010183. [PMID: 31906391]
  • Haijiao Chen, Pengfei Liu, Ting Zhang, Yi Gao, Yingdi Zhang, Xiuyun Shen, Xiao Li, Weidong Shen. Effects of diphyllin as a novel V-ATPase inhibitor on TE-1 and ECA-109 cells. Oncology reports. 2018 Mar; 39(3):921-928. doi: 10.3892/or.2018.6191. [PMID: 29328465]
  • Hong-Jie Zhang, Emily Rumschlag-Booms, Yi-Fu Guan, Dong-Ying Wang, Kang-Lun Liu, Wan-Fei Li, Van H Nguyen, Nguyen M Cuong, Djaja D Soejarto, Harry H S Fong, Lijun Rong. Potent Inhibitor of Drug-Resistant HIV-1 Strains Identified from the Medicinal Plant Justicia gendarussa. Journal of natural products. 2017 06; 80(6):1798-1807. doi: 10.1021/acs.jnatprod.7b00004. [PMID: 28613071]
  • Hong-Jie Zhang, Emily Rumschlag-Booms, Yi-Fu Guan, Kang-Lun Liu, Dong-Ying Wang, Wan-Fei Li, Van Hung Nguyen, Nguyen Manh Cuong, Djaja Doel Soejarto, Harry H S Fong, Lijun Rong. Anti-HIV diphyllin glycosides from Justicia gendarussa. Phytochemistry. 2017 Apr; 136(?):94-100. doi: 10.1016/j.phytochem.2017.01.005. [PMID: 28110956]
  • Shan Yu, Jun-Jiang Lv, Jian-Qiang Zhao, Yan Li, Dong Wang, Chong-Ren Yang, Min Xu, Ying-Jun Zhang. New cytotoxic lignan glycosides from Phyllanthus glaucus. Natural product research. 2016; 30(4):419-25. doi: 10.1080/14786419.2015.1023198. [PMID: 25791206]
  • Siddhartha Das, Abdoul Hamide, Manoj K Mohanty, Ravichandran Muthusamy. Fatal Cleistanthus collinus toxicity: a case report and review of literature. Journal of forensic sciences. 2014 Sep; 59(5):1441-7. doi: 10.1111/1556-4029.12519. [PMID: 25040437]
  • Yulin Ren, Daniel D Lantvit, Youcai Deng, Ragu Kanagasabai, Judith C Gallucci, Tran Ngoc Ninh, Hee-Byung Chai, Djaja D Soejarto, James R Fuchs, Jack C Yalowich, Jianhua Yu, Steven M Swanson, A Douglas Kinghorn. Potent cytotoxic arylnaphthalene lignan lactones from Phyllanthus poilanei. Journal of natural products. 2014 Jun; 77(6):1494-504. doi: 10.1021/np5002785. [PMID: 24937209]
  • Weidong Shen, Xiaoping Zou, Min Chen, Pengfei Liu, Yonghua Shen, Shuling Huang, Huimin Guo, Lili Zhang. Effects of diphyllin as a novel V-ATPase inhibitor on gastric adenocarcinoma. European journal of pharmacology. 2011 Sep; 667(1-3):330-8. doi: 10.1016/j.ejphar.2011.05.042. [PMID: 21645513]
  • Yuk-Man Leung, Yi-Huan Tsou, Chang-Shin Kuo, Shang-Ying Lin, Pau-Yen Wu, Mann-Jen Hour, Yueh-Hsiung Kuo. Arylnaphthalene lignans from Taiwania cryptomerioides as novel blockers of voltage-gated K+ channels. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2010 Dec; 18(1):46-51. doi: 10.1016/j.phymed.2010.04.001. [PMID: 20684875]
  • Suzanne Lim, Jérôme Grassi, Valentina Akhmedjanova, Eric Debiton, Guy Balansard, Richard Beliveau, Chantal Barthomeuf. Reversal of P-glycoprotein-mediated drug efflux by eudesmin from Haplophyllum perforatum and cytotoxicity pattern versus diphyllin, podophyllotoxin and etoposide. Planta medica. 2007 Dec; 73(15):1563-7. doi: 10.1055/s-2007-993754. [PMID: 18074315]
  • Ren-Wang Jiang, Jin-Rong Zhou, Po-Ming Hon, Song-Lin Li, Yan Zhou, Ling-Lin Li, Wen-Cai Ye, Hong-Xi Xu, Pang-Chui Shaw, Paul Pui-Hay But. Lignans from Dysosma versipellis with inhibitory effects on prostate cancer cell lines. Journal of natural products. 2007 Feb; 70(2):283-6. doi: 10.1021/np060430o. [PMID: 17256902]
  • Carole Di Giorgio, Florence Delmas, Valentina Akhmedjanova, Evelyne Ollivier, Iraida Bessonova, Elias Riad, Pierre Timon-David. In vitro antileishmanial activity of diphyllin isolated from Haplophyllum bucharicum. Planta medica. 2005 Apr; 71(4):366-9. doi: 10.1055/s-2005-864106. [PMID: 15856417]
  • Shiow-Hwa Day, Yi-Chen Lin, Mei-Lin Tsai, Lo-Ti Tsao, Horng-Huey Ko, Mei-Ing Chung, Jeng-Chang Lee, Jih-Pyang Wang, Shen-Jeu Won, Chun-Nan Lin. Potent cytotoxic lignans from Justicia procumbens and their effects on nitric oxide and tumor necrosis factor-alpha production in mouse macrophages. Journal of natural products. 2002 Mar; 65(3):379-81. doi: 10.1021/np0101651. [PMID: 11908984]
  • C C Chen, W C Hsin, F N Ko, Y L Huang, J C Ou, C M Teng. Antiplatelet arylnaphthalide lignans from Justicia procumbens. Journal of natural products. 1996 Dec; 59(12):1149-50. doi: 10.1021/np960443+. [PMID: 8988600]