Gossypin (BioDeep_00000003550)

   

natural product PANOMIX_OTCML-2023 Antitumor activity


代谢物信息卡片


Gossypetin-8-C-glucoside

化学式: C21H20O13 (480.0904)
中文名称: 棉酚来源于芙蓉, 棉纤维素
谱图信息: 最多检出来源 Viridiplantae(plant) 40.09%

分子结构信息

SMILES: c1(cc(c2c(c1O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)oc(c(c2=O)O)c1ccc(c(c1)O)O)O)O
InChI: InChI=1S/C21H20O13/c22-5-11-13(27)15(29)17(31)21(32-11)34-19-10(26)4-9(25)12-14(28)16(30)18(33-20(12)19)6-1-2-7(23)8(24)3-6/h1-4,11,13,15,17,21-27,29-31H,5H2

描述信息

A glycosyloxyflavone that is gossypetin attached to a beta-D-glucopyranosyl residue at position 8 via a glycosidic linkage.
Acquisition and generation of the data is financially supported in part by CREST/JST.
Gossypin is a flavone isolated from?Hibiscus vitifolius and has antioxidant, antiinflammatory, anticancer, anticataract, antidiabetic, and hepatoprotective activities. Gossypin inhibits NF-κB and NF-κB-regulated gene expression. Gossypin inhibits RANKL-induced osteoclastogenesis both in mouse primary bone marrow cells and RAW 264.7 cells in vitro[1][2].
Gossypin is a flavone isolated from?Hibiscus vitifolius and has antioxidant, antiinflammatory, anticancer, anticataract, antidiabetic, and hepatoprotective activities. Gossypin inhibits NF-κB and NF-κB-regulated gene expression. Gossypin inhibits RANKL-induced osteoclastogenesis both in mouse primary bone marrow cells and RAW 264.7 cells in vitro[1][2].

同义名列表

4 个代谢物同义名

Gossypin; Gossypetin 8-glucoside; Gossypetin-8-C-glucoside; Gossypin



数据库引用编号

32 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)

29 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 11 ABCB1, BCL2, CASP3, CAT, CCNA2, CCNB1, CCND1, MSMP, NFKB1, NLRP3, PTGS2
Peripheral membrane protein 1 PTGS2
Endoplasmic reticulum membrane 3 BCL2, HMOX1, PTGS2
Nucleus 10 AURKA, BCL2, CASP3, CCNA2, CCNB1, CCND1, HMOX1, NFKB1, NLRP3, PARP1
cytosol 13 AURKA, BCL2, CASP3, CAT, CCNA2, CCNB1, CCND1, GSR, HMOX1, IL1B, NFKB1, NLRP3, PARP1
nuclear body 1 PARP1
centrosome 4 AURKA, CCNA2, CCNB1, CCND1
nucleoplasm 8 AURKA, CASP3, CCNA2, CCNB1, CCND1, HMOX1, NFKB1, PARP1
Cell membrane 2 ABCB1, TNF
Cytoplasmic side 1 HMOX1
Multi-pass membrane protein 1 ABCB1
Golgi apparatus membrane 1 NLRP3
cell surface 2 ABCB1, TNF
glutamatergic synapse 2 AURKA, CASP3
Golgi membrane 1 NLRP3
neuronal cell body 2 CASP3, TNF
Cytoplasm, cytosol 3 IL1B, NLRP3, PARP1
Lysosome 1 IL1B
plasma membrane 2 ABCB1, TNF
Membrane 7 ABCB1, BCL2, CAT, CCNB1, HMOX1, NLRP3, PARP1
apical plasma membrane 1 ABCB1
basolateral plasma membrane 1 AURKA
caveola 1 PTGS2
extracellular exosome 3 ABCB1, CAT, GSR
endoplasmic reticulum 4 BCL2, HMOX1, NLRP3, PTGS2
extracellular space 7 CXCL8, HMOX1, IL10, IL1B, IL6, MSMP, TNF
perinuclear region of cytoplasm 2 AURKA, HMOX1
bicellular tight junction 1 CCND1
mitochondrion 6 BCL2, CAT, GSR, NFKB1, NLRP3, PARP1
protein-containing complex 4 BCL2, CAT, PARP1, PTGS2
intracellular membrane-bounded organelle 1 CAT
Microsome membrane 1 PTGS2
postsynaptic density 2 AURKA, CASP3
pronucleus 1 AURKA
Secreted 6 CXCL8, IL10, IL1B, IL6, MSMP, NLRP3
extracellular region 8 CAT, CXCL8, IL10, IL1B, IL6, NFKB1, NLRP3, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, HMOX1
mitochondrial matrix 3 CAT, CCNB1, GSR
transcription regulator complex 2 NFKB1, PARP1
Cell projection, cilium 1 AURKA
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 AURKA
Nucleus membrane 2 BCL2, CCND1
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 BCL2, CCND1
external side of plasma membrane 2 GSR, TNF
microtubule cytoskeleton 1 AURKA
nucleolus 1 PARP1
midbody 1 AURKA
recycling endosome 1 TNF
spindle midzone 1 AURKA
Single-pass type II membrane protein 1 TNF
Apical cell membrane 1 ABCB1
Membrane raft 1 TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton, spindle 1 AURKA
focal adhesion 1 CAT
microtubule 1 AURKA
spindle 1 AURKA
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
secretory granule 1 IL1B
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
Cell projection, neuron projection 1 AURKA
neuron projection 2 AURKA, PTGS2
ciliary basal body 1 AURKA
cilium 1 AURKA
chromatin 2 NFKB1, PARP1
phagocytic cup 1 TNF
mitotic spindle 1 AURKA
Chromosome 1 PARP1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome, centriole 1 AURKA
Cytoplasm, cytoskeleton, cilium basal body 1 AURKA
centriole 1 AURKA
Nucleus, nucleolus 1 PARP1
spindle pole 1 CCNB1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
Basolateral cell membrane 1 AURKA
site of double-strand break 1 PARP1
Cytoplasm, cytoskeleton, spindle pole 1 AURKA
nuclear envelope 1 PARP1
Endomembrane system 1 NLRP3
microtubule organizing center 1 NLRP3
myelin sheath 1 BCL2
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, NFKB1
endoplasmic reticulum lumen 2 IL6, PTGS2
transcription repressor complex 1 CCND1
specific granule lumen 1 NFKB1
kinetochore 1 AURKA
mitotic spindle pole 1 AURKA
Secreted, extracellular exosome 1 IL1B
Single-pass type IV membrane protein 1 HMOX1
outer kinetochore 1 CCNB1
axon hillock 1 AURKA
chromosome passenger complex 1 AURKA
germinal vesicle 1 AURKA
meiotic spindle 1 AURKA
spindle pole centrosome 1 AURKA
protein-DNA complex 1 PARP1
external side of apical plasma membrane 1 ABCB1
death-inducing signaling complex 1 CASP3
female pronucleus 1 CCNA2
male pronucleus 1 CCNA2
site of DNA damage 1 PARP1
cyclin-dependent protein kinase holoenzyme complex 2 CCNA2, CCND1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
cyclin A2-CDK1 complex 1 CCNA2
cyclin B1-CDK1 complex 1 CCNB1
[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
cyclin D1-CDK4 complex 1 CCND1
[Nuclear factor NF-kappa-B p105 subunit]: Cytoplasm 1 NFKB1
[Nuclear factor NF-kappa-B p50 subunit]: Nucleus 1 NFKB1
I-kappaB/NF-kappaB complex 1 NFKB1
NF-kappaB p50/p65 complex 1 NFKB1
cyclin A2-CDK2 complex 1 CCNA2
cyclin D1-CDK6 complex 1 CCND1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Busra Dincer, Irfan Cinar, Huseyin Serkan Erol, Beste Demirci, Funda Terzi. Gossypin mitigates oxidative damage by downregulating the molecular signaling pathway in oleic acid-induced acute lung injury. Journal of molecular recognition : JMR. 2023 Sep; ?(?):e3058. doi: 10.1002/jmr.3058. [PMID: 37696682]
  • Hao Huang, Jian Wang, Shaik Althaf Hussain, Venkata Subba Reddy Gangireddygari, Yingying Fan. Gossypin exert lipopolysaccharide induced lung inflammation via alteration of Nrf2/HO-1 and NF-κB signaling pathway. Environmental toxicology. 2023 May; ?(?):. doi: 10.1002/tox.23806. [PMID: 37148149]
  • Irfan Cinar, Muhammed Yayla, Taha Tavaci, Erdem Toktay, Rustem Anil Ugan, Pınar Bayram, Hamza Halici. In Vivo and In Vitro Cardioprotective Effect of Gossypin Against Isoproterenol-Induced Myocardial Infarction Injury. Cardiovascular toxicology. 2022 01; 22(1):52-62. doi: 10.1007/s12012-021-09698-3. [PMID: 34599475]
  • Mohamed Katary, Ahmad Salahuddin. Ameliorative effect of gossypin against gentamicin-induced nephrotoxicity in rats. Life sciences. 2017 May; 176(?):75-81. doi: 10.1016/j.lfs.2017.03.009. [PMID: 28302561]
  • Noora Sjöstedt, Kira Holvikari, Päivi Tammela, Heidi Kidron. Inhibition of Breast Cancer Resistance Protein and Multidrug Resistance Associated Protein 2 by Natural Compounds and Their Derivatives. Molecular pharmaceutics. 2017 01; 14(1):135-146. doi: 10.1021/acs.molpharmaceut.6b00754. [PMID: 28043125]
  • Yearam Jung, Soon Young Shin, Yeonjoong Yong, Hyeryoung Jung, Seunghyun Ahn, Young Han Lee, Yoongho Lim. Plant-derived flavones as inhibitors of aurora B kinase and their quantitative structure-activity relationships. Chemical biology & drug design. 2015 May; 85(5):574-85. doi: 10.1111/cbdd.12445. [PMID: 25298094]
  • V M Chandrashekhar, S Ganapaty, A Ramkishan, M Laxmi Narsu. Neuroprotective activity of gossypin from Hibiscus vitifolius against global cerebral ischemia model in rats. Indian journal of pharmacology. 2013 Nov; 45(6):575-80. doi: 10.4103/0253-7613.121367. [PMID: 24347764]
  • Thamizhiniyan Venkatesan, Subramanian Sorimuthu Pillai. Antidiabetic activity of gossypin, a pentahydroxyflavone glucoside, in streptozotocin-induced experimental diabetes in rats. Journal of diabetes. 2012 Mar; 4(1):41-6. doi: 10.1111/j.1753-0407.2011.00145.x. [PMID: 21722326]
  • Pratibha Gautam, S J S Flora. Oral supplementation of gossypin during lead exposure protects alteration in heme synthesis pathway and brain oxidative stress in rats. Nutrition (Burbank, Los Angeles County, Calif.). 2010 May; 26(5):563-70. doi: 10.1016/j.nut.2009.06.008. [PMID: 19647414]
  • Anshoo Gautam, R Vijayaraghavan. Prophylactic effect of gossypin against percutaneously administered sulfur mustard. Biomedical and environmental sciences : BES. 2007 Jun; 20(3):250-9. doi: . [PMID: 17672217]
  • Injae Yoon, Kwang Heun Lee, Jungsook Cho. Gossypin protects primary cultured rat cortical cells from oxidative stress- and beta-amyloid-induced toxicity. Archives of pharmacal research. 2004 Apr; 27(4):454-9. doi: 10.1007/bf02980089. [PMID: 15180313]
  • B H Babu, H N Jayram, M G Nair, K B Ajaikumar, J Padikkala. Free radical scavenging, antitumor and anticarcinogenic activity of gossypin. Journal of experimental & clinical cancer research : CR. 2003 Dec; 22(4):581-9. doi: . [PMID: 15053300]