Timosaponin A-III (BioDeep_00001034396)

Main id: BioDeep_00000011537

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


Smilagenin 3-O-beta-D-glucopyranosyl-(1->2)-beta-D-galactopyranoside

化学式: C39H64O13 (740.4347)
中文名称: 知母皂苷A-Ⅲ
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)C)C)OC1
InChI: InChI=1S/C39H64O13/c1-18-7-12-39(47-17-18)19(2)28-25(52-39)14-24-22-6-5-20-13-21(8-10-37(20,3)23(22)9-11-38(24,28)4)48-36-34(32(45)30(43)27(16-41)50-36)51-35-33(46)31(44)29(42)26(15-40)49-35/h18-36,40-46H,5-17H2,1-4H3/t18-,19+,20-,21+,22-,23+,24+,25+,26-,27-,28+,29-,30+,31+,32+,33-,34-,35+,36-,37+,38+,39-/m1/s1

描述信息

A natural product found in Anemarrhena asphodeloides.
Timosaponin AIII could inhibit acetylcholinesterase (AChE) activity, with an IC50 of 35.4 μM.
Timosaponin AIII could inhibit acetylcholinesterase (AChE) activity, with an IC50 of 35.4 μM.

同义名列表

3 个代谢物同义名

Timosaponin A-III; Smilagenin 3-O-beta-D-glucopyranosyl-(1->2)-beta-D-galactopyranoside; Timosaponin AIII



数据库引用编号

12 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)

32 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, ANXA5, BCL2, BCL2L1, CASP3, CTNNB1, MAPK14, MAPK8, MTOR, MYC, PIK3CA, PTGS2, PTK2, VEGFA
Peripheral membrane protein 4 ANXA5, MTOR, PTGS2, PTK2
Endoplasmic reticulum membrane 3 BCL2, MTOR, PTGS2
Mitochondrion membrane 1 BCL2L1
Nucleus 12 BCL2, CASP3, CTNNB1, GPX4, KDR, MAPK14, MAPK8, MTOR, MYC, PARP1, PTK2, VEGFA
cytosol 12 ANXA5, BCL2, BCL2L1, CASP3, CTNNB1, GPX4, MAPK14, MAPK8, MTOR, PARP1, PIK3CA, PTK2
dendrite 1 MTOR
nuclear body 1 PARP1
phagocytic vesicle 1 MTOR
centrosome 3 BCL2L1, CTNNB1, PTK2
nucleoplasm 7 CASP3, CTNNB1, MAPK14, MAPK8, MTOR, MYC, PARP1
Cell membrane 5 ABCB1, CTNNB1, KDR, PTK2, TNF
Cytoplasmic side 3 BCL2L1, MTOR, PTK2
lamellipodium 2 CTNNB1, PIK3CA
Multi-pass membrane protein 2 ABCB1, CACNA1E
Golgi apparatus membrane 1 MTOR
Synapse 3 CACNA1E, CTNNB1, MAPK8
cell cortex 2 CTNNB1, PTK2
cell junction 2 CTNNB1, KDR
cell surface 3 ABCB1, TNF, VEGFA
glutamatergic synapse 3 CASP3, CTNNB1, MAPK14
Golgi apparatus 2 KDR, VEGFA
Golgi membrane 1 MTOR
lysosomal membrane 1 MTOR
mitochondrial inner membrane 1 BCL2L1
neuronal cell body 3 CACNA1E, CASP3, TNF
presynaptic membrane 1 CTNNB1
sarcolemma 1 ANXA5
Cytoplasm, cytosol 2 BCL2L1, PARP1
Lysosome 1 MTOR
endosome 1 KDR
plasma membrane 7 ABCB1, CACNA1E, CTNNB1, KDR, PIK3CA, PTK2, TNF
synaptic vesicle membrane 1 BCL2L1
Membrane 9 ABCB1, ANXA5, BCL2, CACNA1E, CTNNB1, MTOR, MYC, PARP1, VEGFA
apical plasma membrane 1 ABCB1
axon 1 MAPK8
basolateral plasma membrane 1 CTNNB1
caveola 1 PTGS2
extracellular exosome 4 ABCB1, ANXA5, CTNNB1, GPX4
Lysosome membrane 1 MTOR
endoplasmic reticulum 5 BCL2, BCL2L1, KDR, PTGS2, VEGFA
extracellular space 3 IL6, TNF, VEGFA
perinuclear region of cytoplasm 3 CTNNB1, PIK3CA, PTK2
Schaffer collateral - CA1 synapse 1 CTNNB1
adherens junction 2 CTNNB1, VEGFA
apicolateral plasma membrane 1 CTNNB1
bicellular tight junction 1 CTNNB1
intercalated disc 1 PIK3CA
mitochondrion 5 BCL2, BCL2L1, GPX4, MAPK14, PARP1
protein-containing complex 6 BCL2, CTNNB1, GPX4, MYC, PARP1, PTGS2
intracellular membrane-bounded organelle 1 PTK2
Microsome membrane 2 MTOR, PTGS2
postsynaptic density 1 CASP3
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Secreted 2 IL6, VEGFA
extracellular region 6 ANXA5, IL6, KDR, MAPK14, TNF, VEGFA
Mitochondrion outer membrane 3 BCL2, BCL2L1, MTOR
Single-pass membrane protein 2 BCL2, BCL2L1
mitochondrial outer membrane 3 BCL2, BCL2L1, MTOR
[Isoform 2]: Secreted 1 KDR
Mitochondrion matrix 1 BCL2L1
mitochondrial matrix 1 BCL2L1
anchoring junction 2 KDR, PTK2
transcription regulator complex 2 CTNNB1, PARP1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 2 BCL2L1, PTK2
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 BCL2L1
Nucleus membrane 2 BCL2, BCL2L1
Bcl-2 family protein complex 2 BCL2, BCL2L1
nuclear membrane 2 BCL2, BCL2L1
external side of plasma membrane 3 ANXA5, KDR, TNF
Secreted, extracellular space, extracellular matrix 1 VEGFA
dendritic spine 1 PTK2
Z disc 1 CTNNB1
beta-catenin destruction complex 1 CTNNB1
nucleolus 2 MYC, PARP1
Wnt signalosome 1 CTNNB1
Early endosome 1 KDR
apical part of cell 1 CTNNB1
cell-cell junction 1 CTNNB1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 1 CTNNB1
Apical cell membrane 1 ABCB1
Cytoplasm, perinuclear region 1 PTK2
Membrane raft 2 KDR, TNF
pore complex 1 BCL2
Cell junction, focal adhesion 1 PTK2
Cytoplasm, cytoskeleton 2 CTNNB1, PTK2
focal adhesion 3 ANXA5, CTNNB1, PTK2
Cell junction, adherens junction 1 CTNNB1
flotillin complex 1 CTNNB1
extracellular matrix 1 VEGFA
Nucleus, PML body 1 MTOR
PML body 1 MTOR
collagen-containing extracellular matrix 1 ANXA5
secretory granule 1 VEGFA
fascia adherens 1 CTNNB1
lateral plasma membrane 1 CTNNB1
nuclear speck 1 MAPK14
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 1 KDR
Zymogen granule membrane 1 ANXA5
neuron projection 1 PTGS2
ciliary basal body 1 PTK2
chromatin 2 MYC, PARP1
cell projection 1 PTK2
phagocytic cup 1 TNF
cell periphery 1 CTNNB1
Chromosome 1 PARP1
cytoskeleton 1 PTK2
Cytoplasm, cytoskeleton, cilium basal body 2 CTNNB1, PTK2
Nucleus, nucleolus 2 MYC, PARP1
spindle pole 2 CTNNB1, MAPK14
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
Cytoplasm, cell cortex 1 PTK2
postsynaptic density, intracellular component 1 CTNNB1
microvillus membrane 1 CTNNB1
site of double-strand break 1 PARP1
nuclear envelope 4 GPX4, MTOR, MYC, PARP1
Endomembrane system 2 CTNNB1, MTOR
sorting endosome 1 KDR
monoatomic ion channel complex 1 CACNA1E
Nucleus, nucleoplasm 1 MYC
euchromatin 1 CTNNB1
myelin sheath 1 BCL2
stress fiber 1 PTK2
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 1 MAPK14
endoplasmic reticulum lumen 2 IL6, PTGS2
platelet alpha granule lumen 1 VEGFA
voltage-gated calcium channel complex 1 CACNA1E
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
RNA polymerase II transcription repressor complex 1 MYC
beta-catenin-TCF complex 1 CTNNB1
presynaptic active zone cytoplasmic component 1 CTNNB1
vesicle membrane 1 ANXA5
protein-DNA complex 2 CTNNB1, PARP1
external side of apical plasma membrane 1 ABCB1
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
Rough endoplasmic reticulum 1 MYC
Cytoplasmic vesicle, phagosome 1 MTOR
catenin complex 1 CTNNB1
site of DNA damage 1 PARP1
Myc-Max complex 1 MYC
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
interleukin-6 receptor complex 1 IL6
[Isoform Mitochondrial]: Mitochondrion 1 GPX4
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
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
beta-catenin-TCF7L2 complex 1 CTNNB1
beta-catenin-ICAT complex 1 CTNNB1
Scrib-APC-beta-catenin complex 1 CTNNB1
[Isoform Cytoplasmic]: Cytoplasm 1 GPX4
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[Isoform Bcl-X(L)]: Mitochondrion inner membrane 1 BCL2L1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
nucleoplasmic reticulum 1 MYC


文献列表

  • Ji-Hyuk Park, Wona Jee, So-Mi Park, Ye-Rin Park, Seok Woo Kim, Hanbit Bae, Won-Suk Chung, Jae-Heung Cho, Hyungsuk Kim, Mi-Yeon Song, Hyeung-Jin Jang. Timosaponin A3 Induces Anti-Obesity and Anti-Diabetic Effects In Vitro and In Vivo. International journal of molecular sciences. 2024 Mar; 25(5):. doi: 10.3390/ijms25052914. [PMID: 38474161]
  • Chenjie Shen, Jinging Liu, Huan Liu, Guifang Li, Hanyu Wang, Haixia Tian, Yong Mao, Dong Hua. Timosaponin AIII induces lipid peroxidation and ferroptosis by enhancing Rab7-mediated lipophagy in colorectal cancer cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2024 Jan; 122(?):155079. doi: 10.1016/j.phymed.2023.155079. [PMID: 37863004]
  • Lili Zhou, Yaoquan Ren, Dongmei Li, Weiwei Zhou, Chengke Li, Qiang Wang, Xiangzheng Yang. Timosaponin AIII attenuates precocious puberty in mice through downregulating the hypothalamic-pituitary-gonadal axis. Acta biochimica Polonica. 2023 Mar; 70(1):183-190. doi: 10.18388/abp.2020_6450. [PMID: 36928746]
  • Cong Zhou, Ting Yu, Rui Zhu, Junjie Lu, Xiaohu Ouyang, Zili Zhang, Qianyun Chen, Junyi Li, Jing Cui, Feng Jiang, Kim Yun Jin, Alexey Sarapultsev, Fangfei Li, Ge Zhang, Shanshan Luo, Desheng Hu. Timosaponin AIII promotes non-small-cell lung cancer ferroptosis through targeting and facilitating HSP90 mediated GPX4 ubiquitination and degradation. International journal of biological sciences. 2023; 19(5):1471-1489. doi: 10.7150/ijbs.77979. [PMID: 37056925]
  • Chu-Che Lee, Jen-Pi Tsai, Hsiang-Lin Lee, Yung-Jen Chen, Yong-Syuan Chen, Yi-Hsien Hsieh, Jin-Cherng Chen. Blockage of Autophagy Increases Timosaponin AIII-Induced Apoptosis of Glioma Cells In Vitro and In Vivo. Cells. 2022 12; 12(1):. doi: 10.3390/cells12010168. [PMID: 36611961]
  • Qing-Qi Chang, Long Chen, Ya-Fang Liao, Chun-Lu Yuan, Dan-Dan Zhang. [Mechanism of timosaponin AⅢ in regulation of metabolism against glioblastoma growth]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 Dec; 47(24):6679-6686. doi: 10.19540/j.cnki.cjcmm.20220728.401. [PMID: 36604918]
  • Lijuan Zhang, Shengan Zhang, Min Jiang, Lu Lu, Yue Ding, Ninghui Ma, Yuan Zhao, Sihan Xuchen, Nailian Zhang. Novel Timosaponin AIII-Based Multifunctional Liposomal Delivery System for Synergistic Therapy Against Hepatocellular Carcinoma Cancer. International journal of nanomedicine. 2021; 16(?):5531-5550. doi: 10.2147/ijn.s313759. [PMID: 34429598]
  • Hai-Qiao Wang, Xiao-Mei Gong, Fen Lan, Yi-Han Zhang, Jin-Er Xia, Hai Zhang, Jia-Lin Guo, Min Liu. Biopharmaceutics and Pharmacokinetics of Timosaponin A-III by a Sensitive HPLC-MS/MS Method: Low Bioavailability Resulting from Poor Permeability and Solubility. Current pharmaceutical biotechnology. 2021; 22(5):672-681. doi: 10.2174/1389201021666200707134045. [PMID: 32634081]
  • Zhong-Yan Zhou, Wai-Rong Zhao, Ying Xiao, Xiang-Ming Zhou, Chen Huang, Wen-Ting Shi, Jing Zhang, Qing Ye, Xin-Lin Chen, Jing-Yi Tang. Antiangiogenesis effect of timosaponin AIII on HUVECs in vitro and zebrafish embryos in vivo. Acta pharmacologica Sinica. 2020 Feb; 41(2):260-269. doi: 10.1038/s41401-019-0291-z. [PMID: 31515528]
  • Feng-Ying Han, Xiao-Yu Song, Jing-Jie Chen, Guo-Dong Yao, Shao-Jiang Song. Timosaponin AIII: A novel potential anti-tumor compound from Anemarrhena asphodeloides. Steroids. 2018 12; 140(?):125-130. doi: 10.1016/j.steroids.2018.09.014. [PMID: 30296545]
  • Yang Xie, Xu Zhou, Hu Pei, Ming-Cang Chen, Zhao-Lin Sun, Ya-Ru Xue, Xiao-Ting Tian, Cheng-Gang Huang. Metabolism, pharmacokinetics, and hepatic disposition of xanthones and saponins on Zhimu treatments for exploratively interpreting the discrepancy between the herbal safety and timosaponin A3-induced hepatotoxicity. Acta pharmacologica Sinica. 2018 Dec; 39(12):1923-1934. doi: 10.1038/s41401-018-0012-z. [PMID: 29795136]
  • Bo Yang, Zhirui Liu, Qian Wang, Yifeng Chai, Peiyuan Xia. Pharmacokinetic comparison of seven major bioactive components in normal and depression model rats after oral administration of Baihe Zhimu decoction by liquid chromatography-tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2018 Jan; 148(?):119-127. doi: 10.1016/j.jpba.2017.09.031. [PMID: 28987996]
  • Lu Lu, Yue Ding, Yong Zhang, Rodney Jy Ho, Yuan Zhao, Tong Zhang, Chunrong Guo. Antibody-modified liposomes for tumor-targeting delivery of timosaponin AIII. International journal of nanomedicine. 2018; 13(?):1927-1944. doi: 10.2147/ijn.s153107. [PMID: 29636610]
  • Xi Tan, Hui-Jun Pan, Wei-da Wu, Dan-Dan Zhang. [Inhibitory mechanisms of timosaponin AⅢ on proliferation and growth of human glioblastoma cells]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2017 Mar; 42(6):1160-1166. doi: 10.19540/j.cnki.cjcmm.20170121.025. [PMID: 29027433]
  • Ye Wang, Lei Xu, Li-Li Lou, Shao-Jiang Song, Guo-Dong Yao, Meng-Yao Ge, Toshihiko Hayashi, Shin-Ichi Tashiro, Satoshi Onodera, Takashi Ikejima. Timosaponin AIII induces apoptosis and autophagy in human melanoma A375-S2 cells. Archives of pharmacal research. 2017 Jan; 40(1):69-78. doi: 10.1007/s12272-016-0763-3. [PMID: 27271334]
  • Lu Lu, Yanping Liu, Yue Ding, Jianwei Hou, Yong Zhang, Haiping Xue, Tong Zhang. Preparation of highly purified timosaponin AIII from rhizoma anemarrhenae through an enzymatic method combined with preparative liquid chromatography. Natural product research. 2016 Oct; 30(20):2364-7. doi: 10.1080/14786419.2016.1169416. [PMID: 27055070]
  • Yu Sun, Liyin Liu, Ying Peng, Bingjie Liu, Dongju Lin, Lingzhi Li, Shaojiang Song. Metabolites characterization of timosaponin AIII in vivo and in vitro by using liquid chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 Aug; 997(?):236-43. doi: 10.1016/j.jchromb.2015.06.015. [PMID: 26134298]
  • Guo-long Li, Jie Yang, Jin-ao Duan, Hong-bo Liu, Zhen-hua Zhu, Da-wei Qian, Zhi-shu Tang. [Quality Analysis and Evaluation of Anemarrhena asphodeloides Rhizome from Different Habitats]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 Jun; 38(6):1148-52. doi: . [PMID: 26762052]
  • Yi Feng, Baoting Chen, Aihua Lin, Yiming Liu. Simultaneous determination of timosaponin B-II and A-III in rat plasma by LC-MS/MS and its application to pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Aug; 965(?):119-26. doi: 10.1016/j.jchromb.2014.06.017. [PMID: 25016164]
  • Hye Jin Kim, Se Ri Park, Young Pyo Jang. Extraction-free in situ derivatisation of timosaponin AIII using direct analysis in real time TOF/MS. Phytochemical analysis : PCA. 2014 Jul; 25(4):373-7. doi: 10.1002/pca.2488. [PMID: 24307599]
  • Yao Jia, Bin Wu, Mingsong Fan, Jinhui Wang, Jian Huang, Chenggang Huang. High-performance liquid chromatography-electrospray ionization tandem mass spectrometry for metabolism study of timosaponin AIII. Journal of chromatographic science. 2014 May; 52(5):418-22. doi: 10.1093/chromsci/bmt052. [PMID: 23696387]
  • Zhirui Liu, Xin Dong, Xuan Ding, Xiaofei Chen, Lei Lv, Yueyue Li, Yifeng Chai. Comparative pharmacokinetics of timosaponin B-II and timosaponin A-III after oral administration of Zhimu-Baihe herb-pair, Zhimu extract, free timosaponin B-II and free timosaponin A-III to rats. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 May; 926(?):28-35. doi: 10.1016/j.jchromb.2013.03.003. [PMID: 23542670]
  • Hui-Jun Pan, Xu-Qiang Nie, Duo Liu, Ka Bian. [Effects of four kinds of Chinese medicine monomer on growth of PANC-1 xenograft tumor and studying of molecular mechanism]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2013 Jan; 38(2):245-8. doi: . [PMID: 23672050]
  • Frank W King, Sylvia Fong, Chandi Griffin, Mark Shoemaker, Rick Staub, Yan-Ling Zhang, Isaac Cohen, Emma Shtivelman. Timosaponin AIII is preferentially cytotoxic to tumor cells through inhibition of mTOR and induction of ER stress. PloS one. 2009 Sep; 4(9):e7283. doi: 10.1371/journal.pone.0007283. [PMID: 19789631]
  • Bomi Lee, Kangsik Jung, Dong-Hyun Kim. Timosaponin AIII, a saponin isolated from Anemarrhena asphodeloides, ameliorates learning and memory deficits in mice. Pharmacology, biochemistry, and behavior. 2009 Aug; 93(2):121-7. doi: 10.1016/j.pbb.2009.04.021. [PMID: 19426756]