Solasodine (BioDeep_00000230158)

 

Secondary id: BioDeep_00000003552, BioDeep_00000018656

natural product PANOMIX_OTCML-2023 Chemicals and Drugs Antitumor activity Volatile Flavor Compounds


代谢物信息卡片


(4S,5R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bS)-5,6a,8a,9-Tetramethyl-1,3,4,5,6,6a,6b,7,8,8a,8b,9,11a,12,12a,12b-hexadecahydrospiro[naphtho[2,1:4,5]indeno[2,1-b]furan-10,2-piperidin]-4-ol

化学式: C27H43NO2 (413.3293618)
中文名称: 澳洲茄胺, 澳洲茄次碱, 茄解啶, 茄解鹼, 茄胺, 澳洲茄铵
谱图信息: 最多检出来源 Viridiplantae(plant) 0.4%

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(C)CN6)O[C@H]5C[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O)C1
InChI: InChI=1S/C27H43NO2/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/h5,16-17,19-24,28-29H,6-15H2,1-4H3

描述信息

Solasodine is an oxaspiro compound and steroid alkaloid sapogenin with formula C27H43NO2 found in the Solanum (nightshade) family. It is used as a precursor in the synthesis of complex steroidal compounds such as contraceptive pills. It has a role as a plant metabolite, a teratogenic agent, a diuretic, an antifungal agent, a cardiotonic drug, an immunomodulator, an antipyretic, an apoptosis inducer, an antioxidant, an antiinfective agent, an anticonvulsant, a central nervous system depressant and an antispermatogenic agent. It is an azaspiro compound, an oxaspiro compound, an alkaloid antibiotic, a hemiaminal ether, a sapogenin and a steroid alkaloid. It is a conjugate base of a solasodine(1+).
Purapuridine is a natural product found in Solanum hazenii, Solanum americanum, and other organisms with data available.
An oxaspiro compound and steroid alkaloid sapogenin with formula C27H43NO2 found in the Solanum (nightshade) family. It is used as a precursor in the synthesis of complex steroidal compounds such as contraceptive pills.
Alkaloid from Solanum melanocerasum (garden huckleberry). alpha-Solanigrine is found in fruits.
Origin: Plant; SubCategory_DNP: Steroidal alkaloids, Solanaceous alkaloids
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.206
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.202
Solasodine (Purapuridine) is a steroidal alkaloid that occurs in plants of the Solanaceae family. Solasodine has neuroprotective, antifungal, hypotensive, anticancer, antiatherosclerotic, antiandrogenic and anti-inflammatory activities[1][2].
Solasodine (Purapuridine) is a steroidal alkaloid that occurs in plants of the Solanaceae family. Solasodine has neuroprotective, antifungal, hypotensive, anticancer, antiatherosclerotic, antiandrogenic and anti-inflammatory activities[1][2].
Solasodine (Purapuridine) is a steroidal alkaloid that occurs in plants of the Solanaceae family. Solasodine has neuroprotective, antifungal, hypotensive, anticancer, antiatherosclerotic, antiandrogenic and anti-inflammatory activities[1][2].

同义名列表

36 个代谢物同义名

(4S,5R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bS)-5,6a,8a,9-Tetramethyl-1,3,4,5,6,6a,6b,7,8,8a,8b,9,11a,12,12a,12b-hexadecahydrospiro[naphtho[2,1:4,5]indeno[2,1-b]furan-10,2-piperidin]-4-ol; (2S,2R,4aR,4bS,5R,6aS,6bR,7S,9aS,10aS,10bS)-4a,5,6a,7-tetramethyl-1,2,3,4,4a,4b,5,6,6a,6b,7,9a,10,10a,10b,11-hexadecahydrospiro[naphtho[2,1:4,5]indeno[2,1-b]furan-8,2-piperidin]-2-ol; (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-ol; delta5-20Betaf,22alphaf,25alphaf,27-azaspirosten-3beta-ol; solasodine citrate, (3alpha,22alpha,25R)-isomer; 4-27-00-02000 (Beilstein Handbook Reference); Spirosol-5-en-3-ol, (3.beta.,22.alpha.,25R)-; (3.BETA.,22.ALPHA.,25R)-SPIROSOL-5-EN-3-OL; Spirosol-5-en-3-ol, (3beta,22alpha,25R)-; (3beta,22alpha,25R)-spirosol-5-en-3-ol; solasodine, (3beta,22beta,25S)-isomer; Purapuridine;Solancarpidine;Solasodin; (25R)-22alpha-spirosol-5-en-3beta-ol; (22R,25R)-spirosol-5-en-3beta-ol; Solasod-5-en-3.beta.-ol; Solasod-5-en-3-beta-ol; Solasod-5-en-3beta-ol; SOLASODINE [WHO-DD]; allylamylglycolate; Prestwick3_000663; UNII-L40Y453Y96; SOLASODINE [MI]; (-)-Solasodine; Solancarpidine; Solanearpidine; BPBio1_000799; Purapuridine; Solanidine-S; tomatidenol; SOLASADINE; Solasodine; L40Y453Y96; Solasodin; alpha-Solanigrine; Spirosol-5-en-3-ol; Solasodine



数据库引用编号

59 个数据库交叉引用编号

分类词条

相关代谢途径

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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)

118 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

  • Hadi Ghoomdost Noori, Omid Tadjrobehkar, Elham Moazamian. Biofilm stimulating activity of solanidine and Solasodine in Pseudomonas aeruginosa. BMC microbiology. 2023 08; 23(1):208. doi: 10.1186/s12866-023-02957-z. [PMID: 37533040]
  • Kexin Su, Xuan Yao, Chenxu Guo, Chunmei Qian, Yiying Wang, Xiaoqi Ma, Xiaoyu Wang, Yifu Yang. Solasodine suppresses the metastasis of gastric cancer through claudin-2 via the AMPK/STAT3/NF-κB pathway. Chemico-biological interactions. 2023 Apr; ?(?):110520. doi: 10.1016/j.cbi.2023.110520. [PMID: 37121296]
  • Manthena Navabharath, Varsha Srivastava, Saurabh Gupta, Shoor Vir Singh, Sayeed Ahmad. Ursolic Acid and Solasodine as Potent Anti-Mycobacterial Agents for Combating Paratuberculosis: An Anti-Inflammatory and In Silico Analysis. Molecules (Basel, Switzerland). 2022 Dec; 28(1):. doi: 10.3390/molecules28010274. [PMID: 36615467]
  • Tebogo Mphatlalala Mokgehle, Ntakadzeni Edwin Madala, Nikita Tawanda Tavengwa. Evaluation of a Chaotrope and Kosmotrope in the Multivariate Optimization of PHW-ATPE of Solasodine from Leaves of Solanum mauritianum. Molecules (Basel, Switzerland). 2022 Aug; 27(17):. doi: 10.3390/molecules27175547. [PMID: 36080313]
  • Irfan Khan, Rajesh Kumar, Mahesh Prasad, Ritesh Kumar Srivastav, Vishal Kumar Vishwakarma, Juber Akhtar. Co-Adjuvancy of Solasodine & CoQ10 Against High Fat Diet-Induced Insulin Resistance Rats Via Modulating IRS-I and PPAR-γ Proteins Expression. Drug research. 2022 Jul; 72(6):327-335. doi: 10.1055/a-1806-1366. [PMID: 35724671]
  • Mei Qu, Peng Xue, Qi Zhang, Tiantian Lu, Kun Liu, Bingying Hu, Jingjing Pang, Qianqian Xiao, Tongxin Xu, Quande Wang, Zhongzhe Cheng. Pharmacokinetics, oral bioavailability and metabolic analysis of solasodine in mice by dried blood spot LC-MS/MS and UHPLC-Q-Exactive MS. Journal of pharmaceutical and biomedical analysis. 2022 Feb; 210(?):114542. doi: 10.1016/j.jpba.2021.114542. [PMID: 34979491]
  • Yingchao Fan, Zhumeng Li, Liting Wu, Feng Lin, Jinfeng Shao, Xiaoyan Ma, Yonghua Yao, Wenfang Zhuang, Yuan Wang. Solasodine, Isolated from Solanum sisymbriifolium Fruits, Has a Potent Anti-Tumor Activity Against Pancreatic Cancer. Drug design, development and therapy. 2021; 15(?):1509-1519. doi: 10.2147/dddt.s266746. [PMID: 33888977]
  • Jeeta Sarkar, Arijit Misra, Nirmalya Banerjee. Genetic transfection, hairy root induction and solasodine accumulation in elicited hairy root clone of Solanum erianthum D. Don. Journal of biotechnology. 2020 Nov; 323(?):238-245. doi: 10.1016/j.jbiotec.2020.09.002. [PMID: 32896528]
  • Sonia Verma, Anurag Kuhad, Ranjana Bhandari, Satyendra K Prasad, Anshul Shakya, Rupali S Prasad, Saurabh K Sinha. Effect of ethanolic extract of Solanum virginianum Linn. on neuropathic pain using chronic constriction injury rat model and molecular docking studies. Naunyn-Schmiedeberg's archives of pharmacology. 2020 09; 393(9):1715-1728. doi: 10.1007/s00210-020-01872-8. [PMID: 32388600]
  • Li Lin, Wen Yang, Xing Wei, Yi Wang, Li Zhang, Yunsong Zhang, Zhiming Zhang, Ying Zhao, Maojun Zhao. Enhancement of Solasodine Extracted from Fruits of Solanum nigrum L. by Microwave-Assisted Aqueous Two-Phase Extraction and Analysis by High-Performance Liquid Chromatography. Molecules (Basel, Switzerland). 2019 Jun; 24(12):. doi: 10.3390/molecules24122294. [PMID: 31234274]
  • Mostafa I Fekry, Shahira M Ezzat, Maha M Salama, Ohoud Y Alshehri, Ahmed M Al-Abd. Bioactive glycoalkaloides isolated from Solanum melongena fruit peels with potential anticancer properties against hepatocellular carcinoma cells. Scientific reports. 2019 02; 9(1):1746. doi: 10.1038/s41598-018-36089-6. [PMID: 30741973]
  • Yu-Wen Zhuang, Cun-En Wu, Jin-Yong Zhou, Zhi-Ming Zhao, Chun-Li Liu, Jun-Yi Shen, Hui Cai, Shen-Lin Liu. Solasodine reverses stemness and epithelial-mesenchymal transition in human colorectal cancer. Biochemical and biophysical research communications. 2018 10; 505(2):485-491. doi: 10.1016/j.bbrc.2018.09.094. [PMID: 30268504]
  • Yu-Wen Zhuang, Cun-En Wu, Jin-Yong Zhou, Xu Chen, Jian Wu, Shan Jiang, Hai-Yan Peng, Xi Zou, Jia-Yun Liu, Da-Peng Wu, Tao Gong, Ming-Hao Qi, Tian Xue, Shen-Lin Liu, Hui Cai. Solasodine inhibits human colorectal cancer cells through suppression of the AKT/glycogen synthase kinase-3β/β-catenin pathway. Cancer science. 2017 Nov; 108(11):2248-2264. doi: 10.1111/cas.13354. [PMID: 28803443]
  • Wenqiang Chang, Ying Li, Ming Zhang, Sha Zheng, Yan Li, Hongxiang Lou. Solasodine-3-O-β-d-glucopyranoside kills Candida albicans by disrupting the intracellular vacuole. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2017 Aug; 106(Pt A):139-146. doi: 10.1016/j.fct.2017.05.045. [PMID: 28552788]
  • Jianshe Ma, Xitao Ding, Chengxiang Sun, Chongliang Lin, Xinxin An, Guanyang Lin, Xuezhi Yang, Xianqin Wang. Development and validation a liquid chromatography mass spectrometry for determination of solasodine in rat plasma and its application to a pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Jul; 963(?):24-8. doi: 10.1016/j.jchromb.2014.05.031. [PMID: 24922600]
  • Tejas Sharma, Vishal Airao, Nimesh Panara, Devendra Vaishnav, Vishavas Ranpariya, Navin Sheth, Sachin Parmar. Solasodine protects rat brain against ischemia/reperfusion injury through its antioxidant activity. European journal of pharmacology. 2014 Feb; 725(?):40-6. doi: 10.1016/j.ejphar.2014.01.005. [PMID: 24444441]
  • Marcela Manrique-Moreno, Julián Londoño-Londoño, Małgorzata Jemioła-Rzemińska, Kazimierz Strzałka, Fernando Villena, Marcia Avello, Mario Suwalsky. Structural effects of the Solanum steroids solasodine, diosgenin and solanine on human erythrocytes and molecular models of eukaryotic membranes. Biochimica et biophysica acta. 2014 Jan; 1838(1 Pt B):266-77. doi: 10.1016/j.bbamem.2013.08.003. [PMID: 23954587]
  • Y Sun, Y Zhao, L Wang, H X Lou, A X Cheng. Cloning and expression analysis of squalene synthase, a key enzyme involved in antifungal steroidal glycoalkaloids biosynthesis from Solanum nigrum. Drug discoveries & therapeutics. 2012 Oct; 6(5):242-8. doi: . [PMID: 23229144]
  • Chung-Io Kuo, Chi-Hsein Chao, Mei-Kuang Lu. Effects of auxins on the production of steroidal alkaloids in rapidly proliferating tissue and cell cultures of Solanum lyratum. Phytochemical analysis : PCA. 2012 Jul; 23(4):400-4. doi: 10.1002/pca.1371. [PMID: 22009634]
  • Bill Elliot Cham, Tania Robyn Chase. Solasodine rhamnosyl glycosides cause apoptosis in cancer cells. Do they also prime the immune system resulting in long-term protection against cancer?. Planta medica. 2012 Mar; 78(4):349-53. doi: 10.1055/s-0031-1298149. [PMID: 22399274]
  • Konstantinos A Aliferis, Suha Jabaji. FT-ICR/MS and GC-EI/MS metabolomics networking unravels global potato sprout's responses to Rhizoctonia solani infection. PloS one. 2012; 7(8):e42576. doi: 10.1371/journal.pone.0042576. [PMID: 22880040]
  • S Jisha, S Sreeja, S Manjula. In vitro & in vivo estrogenic activity of glycoside fractions of Solanum nigrum fruit. The Indian journal of medical research. 2011 Sep; 134(?):369-74. doi: ". [PMID: 21985821]
  • Waraporn Putalun. Technology of compact MAb and its application for medicinal plant breeding named as missile type molecular breeding. Current drug discovery technologies. 2011 Mar; 8(1):24-31. doi: 10.2174/157016311794519965. [PMID: 21143130]
  • Kinjal Chauhan, Navin Sheth, Vishavas Ranpariya, Sachin Parmar. Anticonvulsant activity of solasodine isolated from Solanum sisymbriifolium fruits in rodents. Pharmaceutical biology. 2011 Feb; 49(2):194-9. doi: 10.3109/13880209.2010.508499. [PMID: 21062107]
  • 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]
  • Boris Sagredo, N Balbyshev, A Lafta, H Casper, J Lorenzen. A QTL that confers resistance to Colorado potato beetle (Leptinotarsa decemlineata [Say]) in tetraploid potato populations segregating for leptine. TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik. 2009 Nov; 119(7):1171-81. doi: 10.1007/s00122-009-1118-y. [PMID: 19693483]
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  • Xiao Feng Wu, He Ping Shi, Po Tsang, Eric Keung. [Induction and in vitro culture of hairy roots of Solanum nigrum L. var. pauciflorum Liou and its solasodine production]. Fen zi xi bao sheng wu xue bao = Journal of molecular cell biology. 2008 Jun; 41(3):183-91. doi: . [PMID: 18630597]
  • 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]
  • Mukhtar Ahmad Bhat, Sayeed Ahmad, Junaid Aslam, Abdul Mujib, Mahmooduzzfar. Salinity stress enhances production of solasodine in Solanum nigrum L. Chemical & pharmaceutical bulletin. 2008 Jan; 56(1):17-21. doi: 10.1248/cpb.56.17. [PMID: 18175968]
  • 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]
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  • Priti D Trivedi, Brijesh C Patel, Shivprakash Rathnam, Kilambi Pundarikakshudu. A validated liquid chromatographic method for estimation of solasodine in various Solanum species and market formulations. Journal of AOAC International. 2006 Nov; 89(6):1519-23. doi: 10.1093/jaoac/89.6.1519. [PMID: 17225596]
  • Aline Schwarz, Erika C G Felippe, Maria M Bernardi, Helenice S Spinosa. Impaired female sexual behavior of rat offspring exposed to Solanum lycocarpum unripe fruits during gestation and lactation: lack of hormonal and fertility alterations. Pharmacology, biochemistry, and behavior. 2005 Aug; 81(4):928-34. doi: 10.1016/j.pbb.2005.07.003. [PMID: 16095678]
  • Nada C Nikolic, Mihajlo Z Stankovic, Dejan Z Markovic. Liquid-liquid systems for acid hydrolysis of glycoalkaloids from Solanum tuberosum L. tuber sprouts and solanidine extraction. Medical science monitor : international medical journal of experimental and clinical research. 2005 Jul; 11(7):BR200-5. doi: . [PMID: 15990680]
  • Caihong Qu, Yun Xi, Xiangyang Su, Wenping Shi, Feng Zhu. [The preparation and quality control of Solanum lyratum Thunb Extract gel]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2005 Jul; 28(7):605-6. doi: ". [PMID: 16252733]
  • 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]
  • Pooja Bhatnagar, Madhurima Bhatnagar, Amarjit K Nath, D R Sharma. Production of solasodine by Solanum laciniatum using plant tissue culture technique. Indian journal of experimental biology. 2004 Oct; 42(10):1020-3. doi: . [PMID: 15511009]
  • 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]
  • Katsuya Fukuhara, Kuniyoshi Shimizu, Isao Kubo. Arudonine, an allelopathic steroidal glycoalkaloid from the root bark of Solanum arundo Mattei. Phytochemistry. 2004 May; 65(9):1283-6. doi: 10.1016/j.phytochem.2004.03.025. [PMID: 15184013]
  • 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]
  • W Putalun, F Taura, W Qing, H Matsushita, H Tanaka, Y Shoyama. Anti-solasodine glycoside single-chain Fv antibody stimulates biosynthesis of solasodine glycoside in plants. Plant cell reports. 2003 Dec; 22(5):344-9. doi: 10.1007/s00299-003-0689-3. [PMID: 14504907]
  • 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]
  • Paulina Nawłoka, Małgorzata Kalinowska, Cezary Paczkowski, Zdzisław A Wojciechowski. Evidence for essential histidine and dicarboxylic amino-acid residues in the active site of UDP-glucose : solasodine glucosyltransferase from eggplant leaves. Acta biochimica Polonica. 2003; 50(2):567-72. doi: 035002567. [PMID: 12833182]
  • R S Gupta, V P Dixit. Effects of short-term treatment of solasodine on cauda epididymis in dogs. Indian journal of experimental biology. 2002 Feb; 40(2):169-73. doi: . [PMID: 12622179]
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  • 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]
  • C Paczkowski, M Kalinowska, R Woldański, Z A Wojciechowski. Evidence for separate UDP-glucose: spirostanol and UDP-glucose: solasodine glucosyltransferases in Solanum melongena. Advances in experimental medicine and biology. 1996; 404(?):47-55. doi: 10.1007/978-1-4899-1367-8_5. [PMID: 8957283]
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