Irisolidone (BioDeep_00000229935)

 

Secondary id: BioDeep_00000008109

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


5,7-Dihydroxy-6-methoxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one

化学式: C17H14O6 (314.079)
中文名称: 尼泊尔鸢尾异黄酮, 葛花苷元
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 42.45%

分子结构信息

SMILES: c1(c(c(c2c(c1)occ(c2=O)c1ccc(cc1)OC)O)OC)O
InChI: InChI=1S/C17H14O6/c1-21-10-5-3-9(4-6-10)11-8-23-13-7-12(18)17(22-2)16(20)14(13)15(11)19/h3-8,18,20H,1-2H3

描述信息

Irisolidone is a member of 4-methoxyisoflavones.
Irisolidone is a natural product found in Dalbergia sissoo, Wisteria brachybotrys, and other organisms with data available.
Irisolidone is a major isoflavone found in Pueraria lobata flowers. Irisolidone exhibits potent hepatoprotective activity. Irisolidone shows the high efficacy for volume-regulated anion channels (VRAC) blockade (IC50=9.8 μM)[1][2][3].
Irisolidone is a major isoflavone found in Pueraria lobata flowers. Irisolidone exhibits potent hepatoprotective activity. Irisolidone shows the high efficacy for volume-regulated anion channels (VRAC) blockade (IC50=9.8 μM)[1][2][3].

同义名列表

15 个代谢物同义名

5,7-Dihydroxy-6-methoxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one; 5,7-dihydroxy-6-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one; 5,7-dihydroxy-6-methoxy-3-(4-methoxyphenyl)chromen-4-one; Isoflavone, 5,7-dihydroxy-4,6-dimethoxy-; 5,7-Dihydroxy-6,4-dimethoxyisoflavone; 4-O-Methoxytectorigenin; 4-O-Methyltectorigenin; 4-O-Methyltectorigeni; 4-Methoxytectorigenin; Irisolidone; 5,7-dihydroxy-6-methoxy-3-(4-methoxyphenyl)-4-chromenone; 5,7-dihydroxy-6-methoxy-3-(4-methoxyphenyl)chromone; 2345-17-7; C10471; Irisolidone



数据库引用编号

16 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)

70 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 8 AKR1B1, ANG, ARG1, ARG2, IRAK1, NFKB1, PF4, TLR4
Endosome membrane 3 IRAK1, MRC1, TLR4
Nucleus 6 ANG, ARG1, IRAK1, JUND, MPO, NFKB1
cytosol 7 AKR1B1, ANG, ARG1, CD163, GPT, IRAK1, NFKB1
nucleoplasm 5 AKR1B1, IRAK1, JUND, MPO, NFKB1
RNA polymerase II transcription regulator complex 1 JUND
Cell membrane 7 CD163, CD80, CD86, ITGAM, MRC1, TLR4, TNF
Cytoplasmic granule 1 ARG1
cell surface 8 CD80, CD86, IRAK1, ITGAM, ITGAX, MRC1, TLR4, TNF
growth cone 1 ANG
neuronal cell body 2 ANG, TNF
Lysosome 1 MPO
plasma membrane 9 CD163, CD80, CD86, IRAK1, ITGAM, ITGAX, MRC1, TLR4, TNF
Membrane 7 CD163, CD80, CD86, IRAK1, ITGAM, ITGAX, TLR4
extracellular exosome 5 AKR1B1, CD86, GPT, ITGAM, MPO
extracellular space 9 AKR1B1, ANG, ARG1, CXCL8, IL10, ITGAM, MPO, PF4, TNF
perinuclear region of cytoplasm 1 TLR4
mitochondrion 3 AKR1B1, ARG2, NFKB1
protein-containing complex 1 IRAK1
intracellular membrane-bounded organelle 1 MPO
Single-pass type I membrane protein 7 CD163, CD80, CD86, ITGAM, ITGAX, MRC1, TLR4
Secreted 4 ANG, CXCL8, IL10, PF4
extracellular region 9 ANG, ARG1, CD163, CXCL8, IL10, MPO, NFKB1, PF4, TNF
mitochondrial matrix 1 ARG2
transcription regulator complex 2 JUND, NFKB1
centriolar satellite 1 CD86
external side of plasma membrane 7 CD163, CD80, CD86, ITGAM, ITGAX, TLR4, TNF
actin cytoskeleton 1 ANG
nucleolus 1 ANG
Early endosome 1 TLR4
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 2 ITGAM, TNF
basement membrane 1 ANG
collagen-containing extracellular matrix 1 PF4
secretory granule 1 MPO
Cell projection, ruffle 1 TLR4
ruffle 1 TLR4
receptor complex 1 TLR4
chromatin 2 JUND, NFKB1
phagocytic cup 2 TLR4, TNF
Chromosome 1 ANG
Nucleus, nucleolus 1 ANG
Lipid droplet 1 IRAK1
specific granule membrane 1 ITGAM
tertiary granule membrane 2 ITGAM, ITGAX
Cytoplasm, Stress granule 1 ANG
cytoplasmic stress granule 1 ANG
azurophil granule 1 MPO
lipopolysaccharide receptor complex 1 TLR4
plasma membrane raft 1 ITGAM
secretory granule lumen 1 NFKB1
secretory granule membrane 1 ITGAX
transcription repressor complex 1 JUND
platelet alpha granule lumen 1 PF4
specific granule lumen 2 ARG1, NFKB1
endocytic vesicle membrane 1 CD163
endocytic vesicle 1 ANG
azurophil granule lumen 2 ARG1, MPO
phagocytic vesicle lumen 1 MPO
ficolin-1-rich granule membrane 1 ITGAX
integrin complex 2 ITGAM, ITGAX
transcription factor AP-1 complex 1 JUND
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
angiogenin-PRI complex 1 ANG
integrin alphaM-beta2 complex 1 ITGAM
integrin alphaX-beta2 complex 1 ITGAX
protein complex involved in cell adhesion 1 CD80
[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
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
[Soluble CD163]: Secreted 1 CD163


文献列表

  • Hyo-Min Jang, Keon-Tae Park, Hyun-Deok Noh, So-Hyeon Lee, Dong-Hyun Kim. Kakkalide and irisolidone alleviate 2,4,6-trinitrobenzenesulfonic acid-induced colitis in mice by inhibiting lipopolysaccharide binding to toll-like receptor-4 and proteobacteria population. International immunopharmacology. 2019 Aug; 73(?):246-253. doi: 10.1016/j.intimp.2019.05.008. [PMID: 31112869]
  • Guozhe Zhang, Wen Qi, Liangyu Xu, Yoshihiro Kano, Dan Yuan. Pharmacokinetics of irisolidone and its main metabolites in rat plasma determined by ultra performance liquid chromatography/quadrupole time-of-flight mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 Nov; 1005(?):23-9. doi: 10.1016/j.jchromb.2015.09.040. [PMID: 26465087]
  • Ziming Shi, Guozhe Zhang, Lizhu Zhao, Shen Wang, Yoshihiro Kano, Dan Yuan. Excretion of tectorigenin in rat urine orally administrated at different dosages by ultra-performance liquid chromatography coupled to quadrupole time-of-flight mass spectrometry. European journal of drug metabolism and pharmacokinetics. 2015 Sep; 40(3):255-66. doi: 10.1007/s13318-014-0202-0. [PMID: 24789580]
  • Guozhe Zhang, Tianxing Gong, Yoshihiro Kano, Dan Yuan. Screening for in vitro metabolites of kakkalide and irisolidone in human and rat intestinal bacteria by ultra-high performance liquid chromatography/quadrupole time-of-flight mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Feb; 947-948(?):117-24. doi: 10.1016/j.jchromb.2013.12.017. [PMID: 24412694]
  • Guozhe Zhang, Jiahong Sun, Yoshihiro Kano, Dan Yuan. Metabolic profile of irisolidone in rats obtained by ultra-high performance liquid chromatography/quadrupole time-of-flight mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Dec; 941(?):1-9. doi: 10.1016/j.jchromb.2013.09.033. [PMID: 24184829]
  • Hong Wang, Xue Bai, Jiahong Sun, Yoshihiro Kano, Toshiaki Makino, Dan Yuan. Metabolism and excretion of kakkalide and its metabolites in rat urine, bile, and feces as determined by HPLC/UV and LC/MS/MS. Planta medica. 2013 Nov; 79(16):1552-7. doi: 10.1055/s-0033-1350832. [PMID: 24108437]
  • B Roger, V Jeannot, X Fernandez, S Cerantola, J Chahboun. Characterisation and quantification of flavonoids in Iris germanica L. and Iris pallida Lam. resinoids from Morocco. Phytochemical analysis : PCA. 2012 Sep; 23(5):450-5. doi: 10.1002/pca.1379. [PMID: 22213588]
  • Sabrin R M Ibrahim, Gamal A Mohamed, Nawal M Al-Musayeib. New constituents from the rhizomes of Egyptian Iris germanica L. Molecules (Basel, Switzerland). 2012 Mar; 17(3):2587-98. doi: 10.3390/molecules17032587. [PMID: 22388969]
  • Liangliang Liu, Yongjian Ma, Xiaoqing Chen, Xiang Xiong, Shuyun Shi. Screening and identification of BSA bound ligands from Puerariae lobata flower by BSA functionalized Fe₃O₄ magnetic nanoparticles coupled with HPLC-MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Mar; 887-888(?):55-60. doi: 10.1016/j.jchromb.2012.01.008. [PMID: 22305973]
  • Xue Bai, Jialin Qu, Jing Lu, Yoshihiro Kano, Dan Yuan. Pharmacokinetics of kakkalide and its main metabolites in rat plasma determined by HPLC-DAD and LC-MSn. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Feb; 879(5-6):395-402. doi: 10.1016/j.jchromb.2010.12.025. [PMID: 21256817]
  • Xue Bai, Yuanyuan Xie, Jia Liu, Jialin Qu, Yoshihiro Kano, Dan Yuan. Isolation and identification of urinary metabolites of kakkalide in rats. Drug metabolism and disposition: the biological fate of chemicals. 2010 Feb; 38(2):281-6. doi: 10.1124/dmd.109.028555. [PMID: 19910516]
  • Yan-Ling Mu, Yan-Ying Xie, Ling Zhou, Ying Zhong, Lu Liu, Hong Bai, Yuan-Shu Wang, Xiu-Mei Zhang. Cardioprotective effect of 'methylamine irisolidone', a new compound, in hypoxia/reoxygenation injury in cultured rat cardiac myocytes. Chemistry & biodiversity. 2009 Aug; 6(8):1170-7. doi: 10.1002/cbdv.200800314. [PMID: 19697334]
  • Filomena Conforti, Federica Menichini, Daniela Rigano, Felice Senatore. Antiproliferative activity on human cancer cell lines after treatment with polyphenolic compounds isolated from Iris pseudopumila flowers and rhizomes. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2009 Jul; 64(7-8):490-4. doi: 10.1515/znc-2009-7-804. [PMID: 19791498]
  • Dan Yuan, Yuan-Yuan Xie, Xue Bai, Xia Wu, Jing-Yu Yang, Chun-Fu Wu. Inhibitory activity of isoflavones of Pueraria flowers on nitric oxide production from lipopolysaccharide-activated primary rat microglia. Journal of Asian natural products research. 2009 Jun; 11(6):471-81. doi: 10.1080/10286020902819822. [PMID: 20183278]
  • Nighat Nazir, Surrinder Koul, Mushtaq Ahmad Qurishi, Subhash Chander Taneja, Sheikh Fayaz Ahmad, Beenish Khan, Sarang Bani, Ghulam Nabi Qazi. Immunomodulatory activity of isoflavones isolated from Iris germanica (Iridaceae) on T-lymphocytes and cytokines. Phytotherapy research : PTR. 2009 Mar; 23(3):428-33. doi: 10.1002/ptr.2683. [PMID: 19003948]
  • Filomena Conforti, Daniela Rigano, Federica Menichini, Monica Rosa Loizzo, Felice Senatore. Protection against neurodegenerative diseases of Iris pseudopumila extracts and their constituents. Fitoterapia. 2009 Jan; 80(1):62-7. doi: 10.1016/j.fitote.2008.10.005. [PMID: 19000749]
  • Nighat Nazir, Surrinder Koul, Mushtaq Ahmad Qurishi, Subhash Chandra Taneja, Basant Purnima, Ghulam Nabi Qazi. New isoflavones from Iris kashmiriana. Journal of Asian natural products research. 2008 Nov; 10(11-12):1137-41. doi: 10.1080/10286020802413296. [PMID: 19031259]
  • Jeong Mi Kim, Hye Sook Yun-Choi. Anti-platelet effects of flavonoids and flavonoid-glycosides from Sophora japonica. Archives of pharmacal research. 2008 Jul; 31(7):886-90. doi: 10.1007/s12272-001-1242-1. [PMID: 18704331]
  • Kyoung Ah Kang, Rui Zhang, Mei Jing Piao, Dong Ok Ko, Zhi Hong Wang, Bum Joon Kim, Jae Woo Park, Hee Sun Kim, Dong Hyun Kim, Jin Won Hyun. Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect. Bioorganic & medicinal chemistry. 2008 Feb; 16(3):1133-41. doi: 10.1016/j.bmc.2007.10.085. [PMID: 17996449]
  • Sung-Won Min, Dong-Hyun Kim. Kakkalide and irisolidone: HMG-CoA reductase inhibitors isolated from the flower of Pueraria thunbergiana. Biological & pharmaceutical bulletin. 2007 Oct; 30(10):1965-8. doi: 10.1248/bpb.30.1965. [PMID: 17917273]
  • Ji-eun Shin, Eun-Ah Bae, Young Chul Lee, Jin-Youl Ma, Dong-Hyun Kim. Estrogenic effect of main components kakkalide and tectoridin of Puerariae Flos and their metabolites. Biological & pharmaceutical bulletin. 2006 Jun; 29(6):1202-6. doi: 10.1248/bpb.29.1202. [PMID: 16755017]
  • Hae-Ung Lee, Eun-Ah Bae, Dong-Hyun Kim. Hepatoprotective effects of irisolidone on tert-butyl hyperoxide-induced liver injury. Biological & pharmaceutical bulletin. 2005 Mar; 28(3):531-3. doi: 10.1248/bpb.28.531. [PMID: 15744084]
  • Yeo-Ok Han, Myung Joo Han, Sung-Hwan Park, Dong-Hyun Kim. Protective effects of kakkalide from Flos puerariae on ethanol-induced lethality and hepatic injury are dependent on its biotransformation by human intestinal microflora. Journal of pharmacological sciences. 2003 Nov; 93(3):331-6. doi: 10.1254/jphs.93.331. [PMID: 14646251]
  • Eckhard Wollenweber, Jan Frederik Stevens, Karin Klimo, Jutta Knauft, Norbert Frank, Clarissa Gerhäuser. Cancer chemopreventive in vitro activities of isoflavones isolated from Iris germanica. Planta medica. 2003 Jan; 69(1):15-20. doi: 10.1055/s-2003-37030. [PMID: 12567273]
  • Kouya Yamaki, Dong-Hyun Kim, Nama Ryu, Yong Pil Kim, Kuk Hyun Shin, Kazuo Ohuchi. Effects of naturally occurring isoflavones on prostaglandin E2 production. Planta medica. 2002 Feb; 68(2):97-100. doi: 10.1055/s-2002-20263. [PMID: 11859455]
  • Keiko Morito, Tohru Aomori, Toshiharu Hirose, Junei Kinjo, Junichi Hasegawa, Sumito Ogawa, Satoshi Inoue, Masami Muramatsu, Yukito Masamune. Interaction of phytoestrogens with estrogen receptors alpha and beta (II). Biological & pharmaceutical bulletin. 2002 Jan; 25(1):48-52. doi: 10.1248/bpb.25.48. [PMID: 11824555]
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