Solasonine (BioDeep_00000004064)

 

Secondary id: BioDeep_00000183878

PANOMIX_OTCML-2023 Cytotoxicity


代谢物信息卡片


(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-[(1S,2S,4S,5R,6R,7S,8R,9S,12S,13R,16S)-5,7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2-piperidine]-16-yl]oxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol

化学式: C45H73NO16 (883.4929)
中文名称: 澳洲茄碱
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 79.73%

分子结构信息

SMILES: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)C)O)O)O)C)C)C)NC1
InChI: InChI=1S/C45H73NO16/c1-19-8-13-45(46-16-19)20(2)30-27(62-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)57-42-39(61-40-36(54)34(52)31(49)21(3)56-40)38(33(51)29(18-48)59-42)60-41-37(55)35(53)32(50)28(17-47)58-41/h6,19-21,23-42,46-55H,7-18H2,1-5H3

描述信息

Solasonine is an azaspiro compound, an oxaspiro compound and a steroid.
Solasonine is a natural product found in Solanum americanum, Solanum dimidiatum, and other organisms with data available.
Solasonine is a steroidal glycoalkaloid isolated from Solanum nigrum L.. Solasonine has cytotoxicity to human gastric cancer cells[1].
Solasonine is a steroidal glycoalkaloid isolated from Solanum nigrum L.. Solasonine has cytotoxicity to human gastric cancer cells[1].

同义名列表

17 个代谢物同义名

(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-[(1S,2S,4S,5R,6R,7S,8R,9S,12S,13R,16S)-5,7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2-piperidine]-16-yl]oxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol; .BETA.-D-GALACTOPYRANOSIDE, (3.BETA.,22.ALPHA.,25R)-SPIROSOL-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(.BETA.-D-GLUCOPYRANOSYL-(1->3))-; .BETA.-D-GALACTOPYRANOSIDE, (3.BETA.,22.ALPHA.,25R)-SPIROSOL-5-EN-3-YL O-6- DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1-2)-O-(.BETA.-D-GLUCOPYRANOSYL-(1-3))-; beta-D-Galactopyranoside, (3beta,22alpha,25R)-spirosol-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(beta-D-glucopyranosyl-(1-3))- (9CI); beta-D-Galactopyranoside, (3beta,22alpha,25R)-spirosol-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(beta-D-glucopyranosyl-(1-3))-; alpha-solamarine, (3beta,22alpha,25R)-isomer; QCTMYNGDIBTNSK-XEAAVONHSA-N; Tomatine solaradixine; .alpha.-Solasonine; alpha-solamargine; alpha-solamarine; alpha-solasonine; SOLASONINE [MI]; PURAPURINE; Solasonine; Solasonin; Solasonine



数据库引用编号

21 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)

67 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 BCL2, BCL2L1, CASP1, HDAC9, IL18, MAPK14, MAPK8, MYD88, NLRP3, OTUB1, PRKAA2, SGCB, SMO, TLR4
Peripheral membrane protein 1 ACHE
Endosome membrane 2 MYD88, TLR4
Endoplasmic reticulum membrane 3 BCL2, HMOX1, SLC7A11
Mitochondrion membrane 1 BCL2L1
Nucleus 12 ACHE, BCL2, GABPA, GPX4, HDAC9, HMOX1, MAPK14, MAPK8, MYD88, NLRP3, PRKAA2, SMO
cytosol 13 BCL2, BCL2L1, CASP1, GPX4, HMOX1, IL18, MAPK14, MAPK8, MYD88, NLRP3, OTUB1, PRKAA2, SMO
dendrite 2 PRKAA2, SMO
centrosome 1 BCL2L1
nucleoplasm 8 GABPA, HDAC9, HMOX1, MAPK14, MAPK8, OTUB1, PRKAA2, SMO
Cell membrane 6 ACHE, CASP1, SLC7A11, SMO, TLR4, TNF
Cytoplasmic side 2 BCL2L1, HMOX1
Multi-pass membrane protein 2 SLC7A11, SMO
Golgi apparatus membrane 1 NLRP3
Synapse 2 ACHE, MAPK8
cell surface 5 ACHE, MYD88, SLC7A11, TLR4, TNF
glutamatergic synapse 1 MAPK14
Golgi apparatus 3 ACHE, PRKAA2, SMO
Golgi membrane 1 NLRP3
mitochondrial inner membrane 1 BCL2L1
neuromuscular junction 1 ACHE
neuronal cell body 2 PRKAA2, TNF
sarcolemma 1 SGCB
Cytoplasm, cytosol 3 BCL2L1, IL18, NLRP3
plasma membrane 8 ACHE, CASP1, MYD88, SGCB, SLC7A11, SMO, TLR4, TNF
synaptic vesicle membrane 1 BCL2L1
Membrane 7 ACHE, BCL2, HMOX1, NLRP3, PRKAA2, SLC7A11, TLR4
axon 2 MAPK8, PRKAA2
basolateral plasma membrane 1 SLC7A11
extracellular exosome 3 GPX4, OTUB1, SMO
endoplasmic reticulum 5 BCL2, BCL2L1, HMOX1, NLRP3, SMO
extracellular space 4 ACHE, HMOX1, IL18, TNF
perinuclear region of cytoplasm 3 ACHE, HMOX1, TLR4
mitochondrion 5 BCL2, BCL2L1, GPX4, MAPK14, NLRP3
protein-containing complex 4 BCL2, CASP1, GPX4, MYD88
intracellular membrane-bounded organelle 1 SMO
Single-pass type I membrane protein 2 SLC7A11, TLR4
Secreted 3 ACHE, IL18, NLRP3
extracellular region 5 ACHE, IL18, MAPK14, NLRP3, TNF
Mitochondrion outer membrane 2 BCL2, BCL2L1
Single-pass membrane protein 2 BCL2, BCL2L1
mitochondrial outer membrane 3 BCL2, BCL2L1, HMOX1
Mitochondrion matrix 1 BCL2L1
mitochondrial matrix 1 BCL2L1
Extracellular side 1 ACHE
transcription regulator complex 1 HDAC9
Cell projection, cilium 1 SMO
ciliary membrane 1 SMO
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 BCL2L1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 BCL2L1
Nucleus membrane 2 BCL2, BCL2L1
Bcl-2 family protein complex 2 BCL2, BCL2L1
nuclear membrane 3 BCL2, BCL2L1, SMO
external side of plasma membrane 2 TLR4, TNF
nucleolus 1 CASP1
Early endosome 1 TLR4
apical part of cell 1 SLC7A11
recycling endosome 1 TNF
Single-pass type II membrane protein 2 SGCB, TNF
Cell membrane, sarcolemma 1 SGCB
Membrane raft 1 TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 SGCB
microtubule 1 CASP1
basement membrane 1 ACHE
lateral plasma membrane 1 SLC7A11
ciliary tip 1 SMO
nuclear speck 2 MAPK14, PRKAA2
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 2 CASP1, NLRP3
Cell projection, ruffle 1 TLR4
Late endosome 1 SMO
ruffle 1 TLR4
receptor complex 1 TLR4
cilium 1 SMO
chromatin 1 GABPA
phagocytic cup 2 TLR4, TNF
cytoskeleton 1 SGCB
centriole 1 SMO
brush border membrane 1 SLC7A11
spindle pole 1 MAPK14
Basolateral cell membrane 1 SLC7A11
Lipid-anchor, GPI-anchor 1 ACHE
Cell projection, microvillus membrane 1 SLC7A11
microvillus membrane 1 SLC7A11
nuclear envelope 1 GPX4
Endomembrane system 1 NLRP3
microtubule organizing center 1 NLRP3
cytoplasmic stress granule 1 PRKAA2
side of membrane 1 ACHE
myelin sheath 1 BCL2
lipopolysaccharide receptor complex 1 TLR4
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 1 MAPK14
histone methyltransferase complex 1 HDAC9
endocytic vesicle membrane 1 SMO
histone deacetylase complex 1 HDAC9
Single-pass type IV membrane protein 1 HMOX1
9+0 non-motile cilium 1 SMO
AIM2 inflammasome complex 1 CASP1
endoplasmic reticulum-Golgi intermediate compartment 1 SMO
extrinsic component of cytoplasmic side of plasma membrane 1 MYD88
synaptic cleft 1 ACHE
basal dendrite 1 MAPK8
canonical inflammasome complex 1 CASP1
dystrophin-associated glycoprotein complex 1 SGCB
sarcoglycan complex 1 SGCB
nucleotide-activated protein kinase complex 1 PRKAA2
extrinsic component of plasma membrane 1 MYD88
astrocyte projection 1 SLC7A11
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
[Isoform Mitochondrial]: Mitochondrion 1 GPX4
BAD-BCL-2 complex 1 BCL2
[Isoform H]: Cell membrane 1 ACHE
IPAF inflammasome complex 1 CASP1
NLRP1 inflammasome complex 1 CASP1
protease inhibitor complex 1 CASP1
[Isoform Cytoplasmic]: Cytoplasm 1 GPX4
[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


文献列表

  • YingZheng Wang, Tong Wang, WeiDong Liu, GuangZhi Luo, GuangYing Lu, YaNan Zhang, HuaXin Wang. Anticancer effects of solasonine: Evidence and possible mechanisms. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2024 Jan; 171(?):116146. doi: 10.1016/j.biopha.2024.116146. [PMID: 38198952]
  • Tong Liu, Boke Zhang, Yating Gao, Xingxing Zhang, Jiabing Tong, Zegeng Li. Identification of ACHE as the hub gene targeting solasonine associated with non-small cell lung cancer (NSCLC) using integrated bioinformatics analysis. PeerJ. 2023; 11(?):e16195. doi: 10.7717/peerj.16195. [PMID: 37842037]
  • Tian-Chuan Li, Nai-Jie Chen, Yun-Ying Chen, Bing-Jing He, Zhi-Feng Zhou. Solasonine induces apoptosis of the SGC-7901 human gastric cancer cell line in vitro via the mitochondria-mediated pathway. Journal of cellular and molecular medicine. 2022 06; 26(12):3387-3395. doi: 10.1111/jcmm.17343. [PMID: 35524577]
  • Marta Spochacz, Szymon Chowański, Monika Szymczak-Cendlak, Paweł Marciniak, Filomena Lelario, Rosanna Salvia, Marisa Nardiello, Carmen Scieuzo, Laura Scrano, Sabino A Bufo, Zbigniew Adamski, Patrizia Falabella. Solanum nigrum Extract and Solasonine Affected Hemolymph Metabolites and Ultrastructure of the Fat Body and the Midgut in Galleria mellonella. Toxins. 2021 09; 13(9):. doi: 10.3390/toxins13090617. [PMID: 34564621]
  • Katarzyna Szajko, Jarosław Ciekot, Iwona Wasilewicz-Flis, Waldemar Marczewski, Dorota Sołtys-Kalina. Transcriptional and proteomic insights into phytotoxic activity of interspecific potato hybrids with low glycoalkaloid contents. BMC plant biology. 2021 Jan; 21(1):60. doi: 10.1186/s12870-021-02825-w. [PMID: 33482727]
  • Mingming Jin, Chunzi Shi, Tian Li, Yue Wu, Cheng Hu, Gang Huang. Solasonine promotes ferroptosis of hepatoma carcinoma cells via glutathione peroxidase 4-induced destruction of the glutathione redox system. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2020 Sep; 129(?):110282. doi: 10.1016/j.biopha.2020.110282. [PMID: 32531676]
  • Youbao Zhong, Shanshan Li, Liling Chen, Zhiyong Liu, Xiaoquan Luo, Peng Xu, Lai Chen. In Vivo Toxicity of Solasonine and Its Effects on cyp450 Family Gene Expression in the Livers of Male Mice from Four Strains. Toxins. 2018 11; 10(12):. doi: 10.3390/toxins10120487. [PMID: 30477109]
  • C M Lezama-Dávila, J D McChesney, J K Bastos, M A Miranda, R F Tiossi, J de C da Costa, M V Bentley, S E Gaitan-Puch, A P Isaac-Márquez. A New Antileishmanial Preparation of Combined Solamargine and Solasonine Heals Cutaneous Leishmaniasis through Different Immunochemical Pathways. Antimicrobial agents and chemotherapy. 2016 05; 60(5):2732-8. doi: 10.1128/aac.02804-15. [PMID: 26883711]
  • Robert L Glover, Nicholas J Connors, Cristiana Stefan, Ernest Wong, Robert S Hoffman, Lewis S Nelson, Mark Milstein, Silas W Smith, Michael Swerdlow. Electromyographic and laboratory findings in acute Solanum torvum poisoning. Clinical toxicology (Philadelphia, Pa.). 2016; 54(1):61-5. doi: 10.3109/15563650.2015.1110749. [PMID: 26577583]
  • Mendel Friedman. Chemistry and anticarcinogenic mechanisms of glycoalkaloids produced by eggplants, potatoes, and tomatoes. Journal of agricultural and food chemistry. 2015 Apr; 63(13):3323-37. doi: 10.1021/acs.jafc.5b00818. [PMID: 25821990]
  • Yuanyuan Chen, Shuangshuang Zhang, Dahui Chen, Mi Zhou, Jing Zheng, Zheng Xiang. An UPLC-MS/MS method for determination of solasonine in rat plasma and its application of a pharmacokinetic and bioavailability study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 Mar; 985(?):1-5. doi: 10.1016/j.jchromb.2015.01.017. [PMID: 25645955]
  • Renata F J Tiossi, Juliana C Da Costa, Mariza A Miranda, Fabíola S G Praça, James D McChesney, Maria Vitória L B Bentley, Jairo K Bastos. In vitro and in vivo evaluation of the delivery of topical formulations containing glycoalkaloids of Solanum lycocarpum fruits. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2014 Sep; 88(1):28-33. doi: 10.1016/j.ejpb.2014.01.010. [PMID: 24509413]
  • Carla Carolina Munari, Pollyanna Francielli de Oliveira, Jacqueline Costa Lima Campos, Sabrina de Paula Lima Martins, Juliana Carvalho Da Costa, Jairo Kenupp Bastos, Denise Crispim Tavares. Antiproliferative activity of Solanum lycocarpum alkaloidic extract and their constituents, solamargine and solasonine, in tumor cell lines. Journal of natural medicines. 2014 Jan; 68(1):236-41. doi: 10.1007/s11418-013-0757-0. [PMID: 23475509]
  • Raquel R D Moreira, Gilmarcio Z Martins, Nathália O Magalhães, Adélia E Almeida, Rosemeire C L R Pietro, Flávia A J Silva, Regina M B Cicarelli. In vitro trypanocidal activity of solamargine and extracts from Solanum palinacanthum and Solanum lycocarpum of Brazilian cerrado. Anais da Academia Brasileira de Ciencias. 2013 Sep; 85(3):903-7. doi: 10.1590/s0001-37652013000300006. [PMID: 24068082]
  • Karuna Shanker, Shalini Gupta, Pooja Srivastava, Santosh K Srivastava, Subash C Singh, Madan M Gupta. Simultaneous determination of three steroidal glycoalkaloids in Solanum xanthocarpum by high performance thin layer chromatography. Journal of pharmaceutical and biomedical analysis. 2011 Feb; 54(3):497-502. doi: 10.1016/j.jpba.2010.09.025. [PMID: 20965683]
  • Tommaso R I Cataldi, Giuliana Bianco. Capillary electrophoresis of tropane alkaloids and glycoalkaloids occurring in Solanaceae plants. Methods in molecular biology (Clifton, N.J.). 2008; 384(?):171-203. doi: 10.1007/978-1-59745-376-9_9. [PMID: 18392571]
  • Masayuki Yoshikawa, Seikou Nakamura, Kenichi Ozaki, Akira Kumahara, Toshio Morikawa, Hisashi Matsuda. Structures of steroidal alkaloid oligoglycosides, robeneosides A and B, and antidiabetogenic constituents from the Brazilian medicinal plant Solanum lycocarpum. Journal of natural products. 2007 Feb; 70(2):210-4. doi: 10.1021/np0680580. [PMID: 17249729]
  • Christopher A Hall, Traci Hobby, Martin Cipollini. Efficacy and mechanisms of alpha-solasonine-and alpha-solamargine-induced cytolysis on two strains of Trypanosoma cruzi. Journal of chemical ecology. 2006 Nov; 32(11):2405-16. doi: 10.1007/s10886-006-9153-5. [PMID: 17001530]
  • Waraporn Putalun, Preeyaporn Prasamsiwamai, Hiroyuki Tanaka, Yukihiro Shoyama. Solasodine glycoside production by hairy root cultures of Physalis minima Linn. Biotechnology letters. 2004 Apr; 26(7):545-8. doi: 10.1023/b:bile.0000021953.50300.52. [PMID: 15168852]
  • Yaroslav I Korpan, Elena A Nazarenko, Irina V Skryshevskaya, Claude Martelet, Nicole Jaffrezic-Renault, Anna V El'skaya. Potato glycoalkaloids: true safety or false sense of security?. Trends in biotechnology. 2004 Mar; 22(3):147-51. doi: 10.1016/j.tibtech.2004.01.009. [PMID: 15036866]
  • Lina Al Chami, Ramón Méndez, Bernardo Chataing, James O'Callaghan, Alfredo Usubillaga, Luis LaCruz. Toxicological effects of alpha-solamargine in experimental animals. Phytotherapy research : PTR. 2003 Mar; 17(3):254-8. doi: 10.1002/ptr.1122. [PMID: 12672156]
  • M Morillo, V Lequart, E Grand, G Goethals, A Usubillaga, P Villa, P Martin. Synthesis of peracetylated chacotriose. Carbohydrate research. 2001 Sep; 334(4):281-7. doi: 10.1016/s0008-6215(01)00193-8. [PMID: 11527529]
  • J T Blankemeyer, M L McWilliams, J R Rayburn, M Weissenberg, M Friedman. Developmental toxicology of solamargine and solasonine glycoalkaloids in frog embryos. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1998 May; 36(5):383-9. doi: 10.1016/s0278-6915(97)00164-6. [PMID: 9662413]
  • M Friedman, P R Henika, B E Mackey. Feeding of potato, tomato and eggplant alkaloids affects food consumption and body and liver weights in mice. The Journal of nutrition. 1996 Apr; 126(4):989-99. doi: 10.1093/jn/126.4.989. [PMID: 8613903]
  • K Fukuhara, I Kubo. Isolation of steroidal glycoalkaloids from Solanum incanum by two countercurrent chromatographic methods. Phytochemistry. 1991; 30(2):685-7. doi: 10.1016/0031-9422(91)83753-8. [PMID: 1367270]