Tomatidine (BioDeep_00000230162)

Main id: BioDeep_00000002649

 

PANOMIX_OTCML-2023


代谢物信息卡片


5 alpha,20 beta(F),22 alpha(F),25 beta(F),27- azaspirostan-3 beta-ol

化学式: C27H45NO2 (415.345011)
中文名称: 番茄次碱, 番茄碱
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 3.94%

分子结构信息

SMILES: C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@H]5[C@H](C)[C@]6(CCC(CN6)C)O[C@H]5C[C@@]4([H])[C@]3([H])CC[C@@]2([H])C[C@@H](O)C1
InChI: InChI=1S/C27H45NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28-29H,5-15H2,1-4H3/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27-/m0/s1

描述信息

Tomatidine is a 3beta-hydroxy steroid resulting from the substitution of the 3beta-hydrogen of tomatidane by a hydroxy group. It is an azaspiro compound, an oxaspiro compound and a 3beta-hydroxy steroid. It is a conjugate base of a tomatidine(1+). It derives from a hydride of a tomatidane.
Tomatidine is a natural product found in Solanum dunalianum, Solanum kieseritzkii, and other organisms with data available.
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 20
Tomatidine acts as an anti-inflammatory agent by blocking NF-κB and JNK signaling[1]. Tomatidine activates autophagy either in mammal cells or C elegans[2].
Tomatidine acts as an anti-inflammatory agent by blocking NF-κB and JNK signaling[1]. Tomatidine activates autophagy either in mammal cells or C elegans[2].

同义名列表

18 个代谢物同义名

5 alpha,20 beta(F),22 alpha(F),25 beta(F),27- azaspirostan-3 beta-ol; tomatidine, (3beta,5alpha,22alpha,25R)-isomer; Spirosolan-3-ol, (3beta,5alpha,22beta,25S)-; (3beta,5alpha,22beta,25S)-Spirosolan-3-ol; (22S,25S)-5alpha-spirosolan-3beta-ol; 5alpha-Tomatidan-3beta-ol (obsol.); (3beta,5alpha,25S)-spirosolan-3-ol; 5.alpha.-Tomatidan-3.beta.-ol; (22S,25S)-spirosolan-3beta-ol; 5alpha-Tomatidan-3beta-ol; Prestwick3_000573; TOMATIDINE [MI]; UNII-2B73S48786; BPBio1_000426; SMP1_000126; Tomatidine; 2B73S48786; Tomatidin



数据库引用编号

70 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)

3 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。



文献列表

  • Wesam H Abdulaal, Ulfat M Omar, Mustafa Zeyadi, Dina S El-Agamy, Nabil A Alhakamy, Sabrin R M Ibrahim, Naif A R Almalki, Hani Z Asfour, Mohammed W Al-Rabia, Gamal A Mohamed, Mahmoud Elshal. Modulation of the crosstalk between Keap1/Nrf2/HO-1 and NF-κB signaling pathways by Tomatidine protects against inflammation/oxidative stress-driven fulminant hepatic failure in mice. International immunopharmacology. 2024 Mar; 130(?):111732. doi: 10.1016/j.intimp.2024.111732. [PMID: 38402834]
  • Bo Xu, Min Huang, Hang Qi, Hongzhou Xu, Liang Cai. Tomatidine activates autophagy to improve lung injury and inflammation in sepsis by inhibiting NF-κB and MAPK pathways. Molecular genetics and genomics : MGG. 2024 Feb; 299(1):14. doi: 10.1007/s00438-024-02109-6. [PMID: 38400847]
  • Junya Fujimaki, Neo Sayama, Shigenobu Shiotani, Takanori Suzuki, Miki Nonaka, Yasuhito Uezono, Mamoru Oyabu, Yasutomi Kamei, Haruo Nukaya, Keiji Wakabayashi, Akihito Morita, Tomoki Sato, Shinji Miura. The Steroidal Alkaloid Tomatidine and Tomatidine-Rich Tomato Leaf Extract Suppress the Human Gastric Cancer-Derived 85As2 Cells In Vitro and In Vivo via Modulation of Interferon-Stimulated Genes. Nutrients. 2022 Feb; 14(5):. doi: 10.3390/nu14051023. [PMID: 35267998]
  • Christian Bailly. The steroidal alkaloids α-tomatine and tomatidine: Panorama of their mode of action and pharmacological properties. Steroids. 2021 12; 176(?):108933. doi: 10.1016/j.steroids.2021.108933. [PMID: 34695457]
  • Rafat Zrieq, Iqrar Ahmad, Mejdi Snoussi, Emira Noumi, Marcello Iriti, Fahad D Algahtani, Harun Patel, Mohd Saeed, Munazzah Tasleem, Shadi Sulaiman, Kaïss Aouadi, Adel Kadri. Tomatidine and Patchouli Alcohol as Inhibitors of SARS-CoV-2 Enzymes (3CLpro, PLpro and NSP15) by Molecular Docking and Molecular Dynamics Simulations. International journal of molecular sciences. 2021 Oct; 22(19):. doi: 10.3390/ijms221910693. [PMID: 34639036]
  • Shu-Ju Wu, Wen-Chung Huang, Ming-Chin Yu, Ya-Ling Chen, Szu-Chuan Shen, Kuo-Wei Yeh, Chian-Jiun Liou. Tomatidine ameliorates obesity-induced nonalcoholic fatty liver disease in mice. The Journal of nutritional biochemistry. 2021 05; 91(?):108602. doi: 10.1016/j.jnutbio.2021.108602. [PMID: 33548473]
  • Marianne Rocha-Hasler, Gabriel Melo de Oliveira, Aline Nefertiti da Gama, Ludmila Ferreira de Almeida Fiuza, Anna Frieda Fesser, Monica Cal, Romina Rocchetti, Raiza Brandão Peres, Xue Li Guan, Marcel Kaiser, Maria de Nazaré Correia Soeiro, Pascal Mäser. Combination With Tomatidine Improves the Potency of Posaconazole Against Trypanosoma cruzi. Frontiers in cellular and infection microbiology. 2021; 11(?):617917. doi: 10.3389/fcimb.2021.617917. [PMID: 33747979]
  • Pengcheng Wang, Juan Bai, Xuewei Liu, Mi Wang, Xianwei Wang, Ping Jiang. Tomatidine inhibits porcine epidemic diarrhea virus replication by targeting 3CL protease. Veterinary research. 2020 Nov; 51(1):136. doi: 10.1186/s13567-020-00865-y. [PMID: 33176871]
  • Farida S Nirmala, Hyunjung Lee, Ji-Sun Kim, Taeyoul Ha, Chang Hwa Jung, Jiyun Ahn. Green Tomato Extract Prevents Bone Loss in Ovariectomized Rats, a Model of Osteoporosis. Nutrients. 2020 Oct; 12(10):. doi: 10.3390/nu12103210. [PMID: 33096661]
  • Anil Ahsan, Yanrong Zheng, Shijia Ma, Mengru Liu, Ming Cao, Yue Li, Wanqing Zheng, Xinyu Zhou, Minhang Xin, Wei-Wei Hu, Zhong Chen, Xiangnan Zhang. Tomatidine protects against ischemic neuronal injury by improving lysosomal function. European journal of pharmacology. 2020 Sep; 882(?):173280. doi: 10.1016/j.ejphar.2020.173280. [PMID: 32580039]
  • Hikari Kusu, Hiroki Yoshida, Michiko Kudo, Mai Okuyama, Naoki Harada, Kentaro Tsuji-Naito, Mitsugu Akagawa. Tomatidine Reduces Palmitate-Induced Lipid Accumulation by Activating AMPK via Vitamin D Receptor-Mediated Signaling in Human HepG2 Hepatocytes. Molecular nutrition & food research. 2019 11; 63(22):e1801377. doi: 10.1002/mnfr.201801377. [PMID: 31454158]
  • Vignesh K Rangasami, Brijesh Lohchania, Chandrashekhar Voshavar, Harikrishna R Rachamalla, Rajkumar Banerjee, Ashish Dhayani, Saravanabhavan Thangavel, Praveen K Vemula, Srujan Marepally. Exploring membrane permeability of Tomatidine to enhance lipid mediated nucleic acid transfections. Biochimica et biophysica acta. Biomembranes. 2019 01; 1861(1):327-334. doi: 10.1016/j.bbamem.2018.06.006. [PMID: 29902420]
  • Prashant D Sonawane, Uwe Heinig, Sayantan Panda, Netta Segal Gilboa, Meital Yona, S Pradeep Kumar, Noam Alkan, Tamar Unger, Samuel Bocobza, Margarita Pliner, Sergey Malitsky, Maria Tkachev, Sagit Meir, Ilana Rogachev, Asaph Aharoni. Short-chain dehydrogenase/reductase governs steroidal specialized metabolites structural diversity and toxicity in the genus Solanum. Proceedings of the National Academy of Sciences of the United States of America. 2018 06; 115(23):E5419-E5428. doi: 10.1073/pnas.1804835115. [PMID: 29784829]
  • Isabelle Guay, Simon Boulanger, Charles Isabelle, Eric Brouillette, Félix Chagnon, Kamal Bouarab, Eric Marsault, François Malouin. Tomatidine and analog FC04-100 possess bactericidal activities against Listeria, Bacillus and Staphylococcus spp. BMC pharmacology & toxicology. 2018 02; 19(1):7. doi: 10.1186/s40360-018-0197-2. [PMID: 29439722]
  • Morgan J Cichon, Ken M Riedl, Lei Wan, Jennifer M Thomas-Ahner, David M Francis, Steven K Clinton, Steven J Schwartz. Plasma Metabolomics Reveals Steroidal Alkaloids as Novel Biomarkers of Tomato Intake in Mice. Molecular nutrition & food research. 2017 12; 61(12):. doi: 10.1002/mnfr.201700241. [PMID: 28795489]
  • Stéphane Dorsaz, Tiia Snäkä, Quentin Favre-Godal, Pierre Maudens, Nathalie Boulens, Pascal Furrer, Samad Nejad Ebrahimi, Matthias Hamburger, Eric Allémann, Katia Gindro, Emerson Ferreira Queiroz, Howard Riezman, Jean-Luc Wolfender, Dominique Sanglard. Identification and Mode of Action of a Plant Natural Product Targeting Human Fungal Pathogens. Antimicrobial agents and chemotherapy. 2017 09; 61(9):. doi: 10.1128/aac.00829-17. [PMID: 28674054]
  • Daniela Correia da Silva, Paula B Andrade, Patrícia Valentão, David M Pereira. Neurotoxicity of the steroidal alkaloids tomatine and tomatidine is RIP1 kinase- and caspase-independent and involves the eIF2α branch of the endoplasmic reticulum. The Journal of steroid biochemistry and molecular biology. 2017 07; 171(?):178-186. doi: 10.1016/j.jsbmb.2017.03.009. [PMID: 28300624]
  • Chieh-Ying Kuo, Wen-Chung Huang, Chian-Jiun Liou, Li-Chen Chen, Jiann-Jong Shen, Ming-Ling Kuo. Tomatidine Attenuates Airway Hyperresponsiveness and Inflammation by Suppressing Th2 Cytokines in a Mouse Model of Asthma. Mediators of inflammation. 2017; 2017(?):5261803. doi: 10.1155/2017/5261803. [PMID: 29386751]
  • Jenny Liu, Sierra Kanetake, Yun-Hsuan Wu, Christina Tam, Luisa W Cheng, Kirkwood M Land, Mendel Friedman. Antiprotozoal Effects of the Tomato Tetrasaccharide Glycoalkaloid Tomatine and the Aglycone Tomatidine on Mucosal Trichomonads. Journal of agricultural and food chemistry. 2016 Nov; 64(46):8806-8810. doi: 10.1021/acs.jafc.6b04030. [PMID: 27934291]
  • Jason Carere, Michelle L Colgrave, Jiri Stiller, Chunji Liu, John M Manners, Kemal Kazan, Donald M Gardiner. Enzyme-driven metabolomic screening: a proof-of-principle method for discovery of plant defence compounds targeted by pathogens. The New phytologist. 2016 Nov; 212(3):770-779. doi: 10.1111/nph.14067. [PMID: 27353742]
  • Peng Han, Zhi-Jian Wang, Anne-Violette Lavoir, Thomas Michel, Aurélie Seassau, Wen-Yan Zheng, Chang-Ying Niu, Nicolas Desneux. Increased water salinity applied to tomato plants accelerates the development of the leaf miner Tuta absoluta through bottom-up effects. Scientific reports. 2016 09; 6(?):32403. doi: 10.1038/srep32403. [PMID: 27619473]
  • Simon Boulanger, Gabriel Mitchell, Kamal Bouarab, Éric Marsault, André Cantin, Eric H Frost, Eric Déziel, François Malouin. Bactericidal Effect of Tomatidine-Tobramycin Combination against Methicillin-Resistant Staphylococcus aureus and Pseudomonas aeruginosa Is Enhanced by Interspecific Small-Molecule Interactions. Antimicrobial agents and chemotherapy. 2015 Dec; 59(12):7458-64. doi: 10.1128/aac.01711-15. [PMID: 26392496]
  • Giovanni Caprioli, Michael Cahill, Serena Logrippo, Kevin James. Elucidation of the mass fragmentation pathways of tomatidine and β1-hydroxytomatine using orbitrap mass spectrometry. Natural product communications. 2015 Apr; 10(4):575-6. doi: ". [PMID: 25973479]
  • Jorge Mansur Medina, Juliany Cola Fernandes Rodrigues, Otacilio C Moreira, Geórgia Atella, Wanderley de Souza, Hector Barrabin. Mechanisms of growth inhibition of Phytomonas serpens by the alkaloids tomatine and tomatidine. Memorias do Instituto Oswaldo Cruz. 2015 Feb; 110(1):48-55. doi: 10.1590/0074-02760140097. [PMID: 25742263]
  • Giovanni Caprioli, Serena Logrippo, Michael G Cahill, Kevin J James. High-performance liquid chromatography LTQ-Orbitrap mass spectrometry method for tomatidine and non-target metabolites quantification in organic and normal tomatoes. International journal of food sciences and nutrition. 2014 Dec; 65(8):942-7. doi: 10.3109/09637486.2014.950205. [PMID: 25156359]
  • Marcos Taveira, Carla Sousa, Patrícia Valentão, Federico Ferreres, João P Teixeira, Paula B Andrade. Neuroprotective effect of steroidal alkaloids on glutamate-induced toxicity by preserving mitochondrial membrane potential and reducing oxidative stress. The Journal of steroid biochemistry and molecular biology. 2014 Mar; 140(?):106-15. doi: 10.1016/j.jsbmb.2013.12.013. [PMID: 24373792]
  • Bilal Ökmen, Desalegn W Etalo, Matthieu H A J Joosten, Harro J Bouwmeester, Ric C H de Vos, Jérôme Collemare, Pierre J G M de Wit. Detoxification of α-tomatine by Cladosporium fulvum is required for full virulence on tomato. The New phytologist. 2013 Jun; 198(4):1203-1214. doi: 10.1111/nph.12208. [PMID: 23448507]
  • Yandong Shi, Ubiratan Moura, Isabelle Opitz, Alex Soltermann, Hubert Rehrauer, Svenja Thies, Walter Weder, Rolf A Stahel, Emanuela Felley-Bosco. Role of hedgehog signaling in malignant pleural mesothelioma. Clinical cancer research : an official journal of the American Association for Cancer Research. 2012 Sep; 18(17):4646-56. doi: 10.1158/1078-0432.ccr-12-0599. [PMID: 22733539]
  • J M Medina, J C F Rodrigues, W De Souza, G C Atella, H Barrabin. Tomatidine promotes the inhibition of 24-alkylated sterol biosynthesis and mitochondrial dysfunction in Leishmania amazonensis promastigotes. Parasitology. 2012 Sep; 139(10):1253-65. doi: 10.1017/s0031182012000522. [PMID: 22716777]
  • Suk Hyun Choi, Jun-Bae Ahn, Nobuyuki Kozukue, Hyun-Jeong Kim, Yosuke Nishitani, Ling Zhang, Masashi Mizuno, Carol E Levin, Mendel Friedman. Structure-activity relationships of α-, β(1)-, γ-, and δ-tomatine and tomatidine against human breast (MDA-MB-231), gastric (KATO-III), and prostate (PC3) cancer cells. Journal of agricultural and food chemistry. 2012 Apr; 60(15):3891-9. doi: 10.1021/jf3003027. [PMID: 22482398]
  • Yukio Fujiwara, Naoko Kiyota, Keiichiro Tsurushima, Makiko Yoshitomi, Hasita Horlad, Tsuyoshi Ikeda, Toshihiro Nohara, Motohiro Takeya, Ryoji Nagai. Tomatidine, a tomato sapogenol, ameliorates hyperlipidemia and atherosclerosis in apoE-deficient mice by inhibiting acyl-CoA:cholesterol acyl-transferase (ACAT). Journal of agricultural and food chemistry. 2012 Mar; 60(10):2472-9. doi: 10.1021/jf204197r. [PMID: 22224814]
  • Gabriel Mitchell, Mariza Gattuso, Gilles Grondin, Éric Marsault, Kamal Bouarab, François Malouin. Tomatidine inhibits replication of Staphylococcus aureus small-colony variants in cystic fibrosis airway epithelial cells. Antimicrobial agents and chemotherapy. 2011 May; 55(5):1937-45. doi: 10.1128/aac.01468-10. [PMID: 21357296]
  • Jin-Ho Kang, Feng Shi, A Daniel Jones, M David Marks, Gregg A Howe. Distortion of trichome morphology by the hairless mutation of tomato affects leaf surface chemistry. Journal of experimental botany. 2010 Feb; 61(4):1053-64. doi: 10.1093/jxb/erp370. [PMID: 20018901]
  • K Vijaimohan, J Mallika, Devi Cs Shyamala. Chemoprotective Effect of Sobatum against Lithium-Induced Oxidative Damage in Rats. Journal of young pharmacists : JYP. 2010 Jan; 2(1):68-73. doi: 10.4103/0975-1483.62217. [PMID: 21331195]
  • B Fréchette, M Bejan, E Lucas, P Giordanengo, C Vincent. Resistance of wild Solanum accessions to aphids and other potato pests in Quebec field conditions. Journal of insect science (Online). 2010; 10(?):161. doi: 10.1673/031.010.14121. [PMID: 21054161]
  • Rocío González-Lamothe, Gabriel Mitchell, Mariza Gattuso, Moussa S Diarra, François Malouin, Kamal Bouarab. Plant antimicrobial agents and their effects on plant and human pathogens. International journal of molecular sciences. 2009 Jul; 10(8):3400-3419. doi: 10.3390/ijms10083400. [PMID: 20111686]
  • Mendel Friedman, Carol E Levin, Seung-Un Lee, Hyun-Jeong Kim, In-Seon Lee, Jae-Oke Byun, Nobuyuki Kozukue. Tomatine-containing green tomato extracts inhibit growth of human breast, colon, liver, and stomach cancer cells. Journal of agricultural and food chemistry. 2009 Jul; 57(13):5727-33. doi: 10.1021/jf900364j. [PMID: 19514731]
  • Cynthia M Rominger, Wei-Lin Tiger Bee, Robert A Copeland, Elizabeth A Davenport, Aidan Gilmartin, Richard Gontarek, Keith R Hornberger, Lorena A Kallal, Zhihong Lai, Kenneth Lawrie, Quinn Lu, Lynette McMillan, Maggie Truong, Peter J Tummino, Brandon Turunen, Matthew Will, William J Zuercher, David H Rominger. Evidence for allosteric interactions of antagonist binding to the smoothened receptor. The Journal of pharmacology and experimental therapeutics. 2009 Jun; 329(3):995-1005. doi: 10.1124/jpet.109.152090. [PMID: 19304771]
  • Ryan F Seipke, Rosemary Loria. Streptomyces scabies 87-22 possesses a functional tomatinase. Journal of bacteriology. 2008 Dec; 190(23):7684-92. doi: 10.1128/jb.01010-08. [PMID: 18835993]
  • David M Parish, Thomas Szyperski. Simultaneously cycled NMR spectroscopy. Journal of the American Chemical Society. 2008 Apr; 130(14):4925-33. doi: 10.1021/ja711454e. [PMID: 18338896]
  • Chun-Te Chiang, Tzong-Der Way, Shang-Jie Tsai, Jen-Kun Lin. Diosgenin, a naturally occurring steroid, suppresses fatty acid synthase expression in HER2-overexpressing breast cancer cells through modulating Akt, mTOR and JNK phosphorylation. FEBS letters. 2007 Dec; 581(30):5735-42. doi: 10.1016/j.febslet.2007.11.021. [PMID: 18022396]
  • Sayaka Matsushita, Yoshihiro Yanai, Asami Fusyuku, Yukio Fujiwara, Tsuyoshi Ikeda, Masateru Ono, Chunguang Han, Makoto Ojika, Toshihiro Nohara. Efficient conversion of tomatidine into neuritogenic pregnane derivative. Chemical & pharmaceutical bulletin. 2007 Jul; 55(7):1077-8. doi: 10.1248/cpb.55.1077. [PMID: 17603206]
  • Veronika Simons, John P Morrissey, Maita Latijnhouwers, Michael Csukai, Adam Cleaver, Carol Yarrow, Anne Osbourn. Dual effects of plant steroidal alkaloids on Saccharomyces cerevisiae. Antimicrobial agents and chemotherapy. 2006 Aug; 50(8):2732-40. doi: 10.1128/aac.00289-06. [PMID: 16870766]
  • Olaf Kaup, Ines Gräfen, Eva-Maria Zellermann, Rudolf Eichenlaub, Karl-Heinz Gartemann. Identification of a tomatinase in the tomato-pathogenic actinomycete Clavibacter michiganensis subsp. michiganensis NCPPB382. Molecular plant-microbe interactions : MPMI. 2005 Oct; 18(10):1090-8. doi: 10.1094/mpmi-18-1090. [PMID: 16255248]
  • Tiina Väänänen, Teemu Ikonen, Veli-Matti Rokka, Pirjo Kuronen, Ritva Serimaa, Velimatti Ollilainen. Influence of incorporated wild Solanum genomes on potato properties in terms of starch nanostructure and glycoalkaloid content. Journal of agricultural and food chemistry. 2005 Jun; 53(13):5313-25. doi: 10.1021/jf0501342. [PMID: 15969512]
  • V-M Rokka, J Laurila, A Tauriainen, I Laakso, J Larkka, M Metzler, L Pietilä. Glycoalkaloid aglycone accumulations associated with infection by Clavibacter michiganensis ssp. sepedonicus in potato species Solanum acaule and Solanum tuberosum and their interspecific somatic hybrids. Plant cell reports. 2005 Mar; 23(10-11):683-91. doi: 10.1007/s00299-004-0868-x. [PMID: 15365763]
  • Atsuko Kohara, Chiharu Nakajima, Kimiko Hashimoto, Toshihiko Ikenaga, Hiroyuki Tanaka, Yukihiro Shoyama, Shigeo Yoshida, Toshiya Muranaka. A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum. Plant molecular biology. 2005 Jan; 57(2):225-39. doi: 10.1007/s11103-004-7204-2. [PMID: 15821879]
  • Shin-ichi Ito, Tomomi Eto, Shuhei Tanaka, Naoki Yamauchi, Hiroyuki Takahara, Tsuyoshi Ikeda. Tomatidine and lycotetraose, hydrolysis products of alpha-tomatine by Fusarium oxysporum tomatinase, suppress induced defense responses in tomato cells. FEBS letters. 2004 Jul; 571(1-3):31-4. doi: 10.1016/j.febslet.2004.06.053. [PMID: 15280013]
  • Kap-Rang Lee, Nobuyuki Kozukue, Jae-Sook Han, Joon-Hong Park, Eun-Young Chang, Eun-Jung Baek, Jong-Sun Chang, Mendel Friedman. Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells. Journal of agricultural and food chemistry. 2004 May; 52(10):2832-9. doi: 10.1021/jf030526d. [PMID: 15137822]
  • Nobuyuki Kozukue, Jae-Sook Han, Kap-Rang Lee, Mendel Friedman. Dehydrotomatine and alpha-tomatine content in tomato fruits and vegetative plant tissues. Journal of agricultural and food chemistry. 2004 Apr; 52(7):2079-83. doi: 10.1021/jf0306845. [PMID: 15053555]
  • Mendel Friedman, P R Henika, B E Mackey. Effect of feeding solanidine, solasodine and tomatidine to non-pregnant and pregnant mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2003 Jan; 41(1):61-71. doi: 10.1016/s0278-6915(02)00205-3. [PMID: 12453729]
  • Giuliana Bianco, Philippe Schmitt-Kopplin, Giuseppe De Benedetto, Antonius Kettrup, Tommaso R I Cataldi. Determination of glycoalkaloids and relative aglycones by nonaqueous capillary electrophoresis coupled with electrospray ionization-ion trap mass spectrometry. Electrophoresis. 2002 Sep; 23(17):2904-12. doi: 10.1002/1522-2683(200209)23:17<2904::aid-elps2904>3.0.co;2-1. [PMID: 12207298]
  • S Cherkaoui, K Bekkouche, P Christen, J L Veuthey. Non-aqueous capillary electrophoresis with diode array and electrospray mass spectrometric detection for the analysis of selected steroidal alkaloids in plant extracts. Journal of chromatography. A. 2001 Jul; 922(1-2):321-8. doi: 10.1016/s0021-9673(01)00907-4. [PMID: 11486878]
  • Y Lavie, T Harel-Orbital, W Gaffield, M Liscovitch. Inhibitory effect of steroidal alkaloids on drug transport and multidrug resistance in human cancer cells. Anticancer research. 2001 Mar; 21(2A):1189-94. doi: . [PMID: 11396162]
  • T Roldán-Arjona, A Pérez-Espinosa, M Ruiz-Rubio. Tomatinase from Fusarium oxysporum f. sp. lycopersici defines a new class of saponinases. Molecular plant-microbe interactions : MPMI. 1999 Oct; 12(10):852-61. doi: 10.1094/mpmi.1999.12.10.852. [PMID: 10517025]
  • J Laurila, I Laakso, T Väänänen, P Kuronen, R Huopalahti, E Pehu. Determination of solanidine- and tomatidine-type glycoalkaloid aglycons by gas Chromatography/Mass spectrometry. Journal of agricultural and food chemistry. 1999 Jul; 47(7):2738-42. doi: 10.1021/jf981009b. [PMID: 10552556]
  • J T Blankemeyer, J B White, B K Stringer, M Friedman. Effect of alpha-tomatine and tomatidine on membrane potential of frog embryos and active transport of ions in frog skin. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1997 Jul; 35(7):639-46. doi: 10.1016/s0278-6915(97)00038-0. [PMID: 9301646]
  • 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]
  • R F Keeler, D C Baker, W Gaffield. Spirosolane-containing Solanum species and induction of congenital craniofacial malformations. Toxicon : official journal of the International Society on Toxinology. 1990; 28(8):873-84. doi: 10.1016/0041-0101(90)90017-2. [PMID: 2080514]
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