Episarsasapogenin (BioDeep_00000842190)

   


代谢物信息卡片


(25R)-5alpha-Spirostan-3beta-ol

化学式: C27H44O3 (416.3290274)
中文名称:
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)O)C)C)C)OC1
InChI: InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3

描述信息

Episarsasapogenin, also known as smilagenin or sarsasapogenin, (3beta,5beta,25s)-isomer, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Episarsasapogenin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Episarsasapogenin can be found in fenugreek, which makes episarsasapogenin a potential biomarker for the consumption of this food product.

同义名列表

2 个代谢物同义名

(25R)-5alpha-Spirostan-3beta-ol; Episarsasapogenin



数据库引用编号

3 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)

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

  • Shuangshuang Yang, Lei Fan, Rui Zhang, Chenghuan Song, Jiyun Shi, Jing Wang, Pingao Zhang, Hao Wang, Yongfang Zhang. Smilagenin induces expression and epigenetic remodeling of BDNF in alzheimer's disease. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Sep; 118(?):154956. doi: 10.1016/j.phymed.2023.154956. [PMID: 37499345]
  • Yuan Dai, Panwang Liu, Wen Wen, Ping Li, Chen Yang, Ping Wang, Shijun Xu. Sarsasapogenin, a principal active component absorbed into blood of total saponins of Anemarrhena, attenuates proliferation and invasion in rheumatoid arthritis fibroblast-like synoviocytes through downregulating PKM2 inhibited pathological glycolysis. Phytotherapy research : PTR. 2023 Jan; ?(?):. doi: 10.1002/ptr.7712. [PMID: 36631974]
  • Zuzana Bednarikova, Miroslav Gancar, Rui Wang, Lulu Zheng, Yun Tang, Yating Luo, Yan Huang, Barbora Spodniakova, Lei Ma, Zuzana Gazova. Extracts from Chinese herbs with anti-amyloid and neuroprotective activities. International journal of biological macromolecules. 2021 May; 179(?):475-484. doi: 10.1016/j.ijbiomac.2021.03.013. [PMID: 33675837]
  • Lixia Pei, Yiyi Ye, Wenshu Zhao, Qun Ye, Songlan Ge, Zi-Wei Jiang, Xiao-Qiang Liang, Hai-Xian Gan, Lei Ma. A validated UPLC-MS/MS method for quantitative determination of a potent neuroprotective agent Sarsasapogenin-AA13 in rat plasma: Application to pharmacokinetic studies. Biomedical chromatography : BMC. 2020 Mar; 34(3):e4775. doi: 10.1002/bmc.4775. [PMID: 31845362]
  • Priya Kashyap, Kalaivani Muthusamy, Manisha Niranjan, Shweta Trikha, Suresh Kumar. Sarsasapogenin: A steroidal saponin from Asparagus racemosus as multi target directed ligand in Alzheimer's disease. Steroids. 2020 01; 153(?):108529. doi: 10.1016/j.steroids.2019.108529. [PMID: 31672628]
  • Shu Wang, Mengqi Liu, Wenbao Wang, Ting Li, Mengsuo Cui, Wenliang Sun, Xinggang Yang, Shaojiang Song. Preparation and Evaluation of mPEG-PLGA Block Copolymer Micelles Loaded with a Sarsasapogenin Derivative. AAPS PharmSciTech. 2019 Aug; 20(7):280. doi: 10.1208/s12249-019-1491-z. [PMID: 31399832]
  • Lixia Pei, Songlan Ge, Yiyi Ye, Ziwei Jiang, Xiaoqiang Liang, Wenshu Zhao, Lei Ma. Development and validation of a UPLC-MS/MS method for determination of Sarsasapogenin-AA22 in rat plasma and its application to a pharmacokinetic study. Biomedical chromatography : BMC. 2018 Oct; 32(10):e4295. doi: 10.1002/bmc.4295. [PMID: 29797524]
  • Yi Zhang, Lijun Jin, Jinchang Liu, Wei Wang, Haiyang Yu, Jian Li, Qian Chen, Tao Wang. Effect and mechanism of dioscin from Dioscorea spongiosa on uric acid excretion in animal model of hyperuricemia. Journal of ethnopharmacology. 2018 Mar; 214(?):29-36. doi: 10.1016/j.jep.2017.12.004. [PMID: 29233733]
  • Rajarshi Sengupta, Amy Barone, Jayne Marasa, Sara Taylor, Erin Jackson, Nicole M Warrington, Shyam Rao, Albert H Kim, Jeffrey R Leonard, David Piwnica-Worms, Joshua B Rubin. Novel chemical library screen identifies naturally occurring plant products that specifically disrupt glioblastoma-endothelial cell interactions. Oncotarget. 2015 Jul; 6(21):18282-92. doi: 10.18632/oncotarget.4957. [PMID: 26286961]
  • 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]
  • R Zhang, Z Wang, P A Howson, Z Xia, S Zhou, E Wu, Z Xia, Y Hu. Smilagenin attenuates beta amyloid (25-35)-induced degeneration of neuronal cells via stimulating the gene expression of brain-derived neurotrophic factor. Neuroscience. 2012 May; 210(?):275-85. doi: 10.1016/j.neuroscience.2012.03.017. [PMID: 22441042]
  • Shi-Fu Xiao, Hai-Bo Xue, Xia Li, Chao Chen, Guan-Jun Li, Cheng-Mei Yuan, Ming-Yuan Zhang. A double-blind, placebo-controlled study of traditional Chinese medicine sarsasapogenin added to risperidone in patients with negative symptoms dominated schizophrenia. Neuroscience bulletin. 2011 Aug; 27(4):258-68. doi: 10.1007/s12264-011-1417-6. [PMID: 21788997]
  • Jagmohan S Negi, Pramod Singh, Geeta Joshi Nee Pant, M S M Rawat. High-performance liquid chromatography analysis of plant saponins: An update 2005-2010. Pharmacognosy reviews. 2011 Jul; 5(10):155-8. doi: 10.4103/0973-7847.91109. [PMID: 22303089]
  • M B Botura, G D Silva, H G Lima, J V A Oliveira, T S Souza, J D G Santos, A Branco, E L T Moreira, M A O Almeida, M J M Batatinha. In vivo anthelmintic activity of an aqueous extract from sisal waste (Agave sisalana Perr.) against gastrointestinal nematodes in goats. Veterinary parasitology. 2011 Apr; 177(1-2):104-10. doi: 10.1016/j.vetpar.2010.11.039. [PMID: 21156340]
  • Tabasum Sidiq, Anamika Khajuria, Pankaj Suden, Surjeet Singh, N K Satti, K A Suri, V K Srinivas, E Krishna, R K Johri. A novel sarsasapogenin glycoside from Asparagus racemosus elicits protective immune responses against HBsAg. Immunology letters. 2011 Mar; 135(1-2):129-35. doi: 10.1016/j.imlet.2010.10.013. [PMID: 21035507]
  • Liwei Wang, Xiaodong Wang, Xiaofan Yuan, Bing Zhao. Simultaneous analysis of diosgenin and sarsasapogenin in Asparagus officinalis byproduct by thin-layer chromatography. Phytochemical analysis : PCA. 2011 Jan; 22(1):14-7. doi: 10.1002/pca.1244. [PMID: 20799270]
  • Jing Wang, Ji-hua Liu, Xu Guo, Jian Zhang, Bo-yang Yu. A sensitive indirect competitive enzyme-linked immunosorbent assay for the detection of sarsasapogenin in rat plasma. Acta pharmacologica Sinica. 2010 Aug; 31(8):984-9. doi: 10.1038/aps.2010.85. [PMID: 20686523]
  • Ydia M Valadares, Geraldo C Brandão'a, Erna G Kroon, José D Souza Filho, Alaņņde B Oliveira, Fernão C Braga. Antiviral activity of Solanum paniculatum extract and constituents. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2009 Nov; 64(11-12):813-8. doi: 10.1515/znc-2009-11-1210. [PMID: 20158151]
  • Li Yang, Feng Feng, Yuan Gao. [Chemical constituents from herb of Solanum lyratum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Jul; 34(14):1805-8. doi: . [PMID: 19894512]
  • I Hakki Cigerci, A Fatih Fidan, Muhsin Konuk, Hayati Yuksel, Ismail Kucukkurt, Abdullah Eryavuz, Nalan Baysu Sozbilir. The protective potential of Yucca schidigera (Sarsaponin 30) against nitrite-induced oxidative stress in rats. Journal of natural medicines. 2009 Jul; 63(3):311-7. doi: 10.1007/s11418-009-0338-4. [PMID: 19434470]
  • Xue-Feng Huang, Yu-Ying Lin, Ling-Yi Kong. Steroids from the roots of Asparagus officinalis and their cytotoxic activity. Journal of integrative plant biology. 2008 Jun; 50(6):717-22. doi: 10.1111/j.1744-7909.2008.00651.x. [PMID: 18713412]
  • Fei Sa, Jian-Li Gao, Kwok-Pui Fung, Ying Zheng, Simon Ming-Yuen Lee, Yi-Tao Wang. Anti-proliferative and pro-apoptotic effect of Smilax glabra Roxb. extract on hepatoma cell lines. Chemico-biological interactions. 2008 Jan; 171(1):1-14. doi: 10.1016/j.cbi.2007.08.012. [PMID: 17996228]
  • Bertrand Liagre, Pascale Vergne-Salle, David Y Leger, Jean-Louis Beneytout. Inhibition of human rheumatoid arthritis synovial cell survival by hecogenin and tigogenin is associated with increased apoptosis, p38 mitogen-activated protein kinase activity and upregulation of cyclooxygenase-2. International journal of molecular medicine. 2007 Oct; 20(4):451-60. doi: . [PMID: 17786275]
  • Juan Chen, Chong-jun Yang, Yu-hai Guo. [Studies on accumulation of active ingredients, N, P and K in Anemarrhena asphodeloides]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Aug; 32(15):1504-7. doi: ". [PMID: 17972573]
  • Hua Zhou, Xi Yang, Naili Wang, Yaou Zhang, Guoping Cai. Tigogenin inhibits adipocytic differentiation and induces osteoblastic differentiation in mouse bone marrow stromal cells. Molecular and cellular endocrinology. 2007 May; 270(1-2):17-22. doi: 10.1016/j.mce.2007.01.017. [PMID: 17363141]
  • Shen Song, Tu-lin Lu, De Ji. [Investigation on the technology of processing Anemarrhena asphodeloides Bge. without hair by water]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2007 Mar; 30(3):335-8. doi: . [PMID: 17634045]
  • Li-Xiang Ren, Yi-Fan Luo, Xia Li, Dai-Ying Zuo, Ying-Liang Wu. Antidepressant-like effects of sarsasapogenin from Anemarrhena asphodeloides BUNGE (Liliaceae). Biological & pharmaceutical bulletin. 2006 Nov; 29(11):2304-6. doi: 10.1248/bpb.29.2304. [PMID: 17077534]
  • 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]
  • C Corbière, S Battu, B Liagre, P J P Cardot, J L Beneytout. SdFFF monitoring of cellular apoptosis induction by diosgenin and different inducers in the human 1547 osteosarcoma cell line. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Sep; 808(2):255-62. doi: 10.1016/j.jchromb.2004.05.026. [PMID: 15261819]
  • Yoko Uematsu, Keiko Hirata, Kumi Suzuki, Kenji Iida, Kunihiro Kamata. Investigation of spectrophotometrically determined substances in Yucca extract by GC/MS, TLC and on-column injection GC. Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan. 2004 Jun; 45(3):141-5. doi: 10.3358/shokueishi.45.141. [PMID: 15468933]
  • Bertrand Liagre, Pascale Vergne-Salle, Cecile Corbiere, Jean L Charissoux, Jean L Beneytout. Diosgenin, a plant steroid, induces apoptosis in human rheumatoid arthritis synoviocytes with cyclooxygenase-2 overexpression. Arthritis research & therapy. 2004; 6(4):R373-83. doi: 10.1186/ar1199. [PMID: 15225373]
  • Cecile Corbiere, Bertrand Liagre, Arnaud Bianchi, Karim Bordji, Michel Dauça, Patrick Netter, Jean-Louis Beneytout. Different contribution of apoptosis to the antiproliferative effects of diosgenin and other plant steroids, hecogenin and tigogenin, on human 1547 osteosarcoma cells. International journal of oncology. 2003 Apr; 22(4):899-905. doi: . [PMID: 12632085]
  • Alistair L Wilkins, Lucy P Meagher, Barry L Smith, Christopher O Miles. Ovine metabolism of diosgenin coated on cellulose in relation to hepatogenous photosensitization of ruminants. Veterinary and human toxicology. 2003 Feb; 45(1):24-7. doi: . [PMID: 12583692]
  • 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]
  • C Pazkowski, M Kalinowska, Z A Wojciechowski. Phospholipids modulate the substrate specificity of soluble UDP-glucose:steroid glucosyltransferase from eggplant leaves. Phytochemistry. 2001 Nov; 58(5):663-9. doi: 10.1016/s0031-9422(01)00292-8. [PMID: 11672729]
  • B Yu, X Luo, Y Xu, L Xu, G Xu. [Determination of sarsasapogenin in 'tian dong' by TLCS]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2001 Aug; 24(8):577-8. doi: ". [PMID: 11715195]
  • A Flåøyen, A L Wilkins, D Deng, T Brekke. Ovine metabolism of saponins: evaluation of a method for estimating the ovine uptake of steroidal saponins from Narthecium ossifragum. Veterinary research communications. 2001 Apr; 25(3):225-38. doi: 10.1023/a:1006485726523. [PMID: 11334151]
  • C Cruz, D Driemeier, V S Pires, E M Colodel, A T Taketa, E P Schenkel. Isolation of steroidal sapogenins implicated in experimentally induced cholangiopathy of sheep grazing Brachiaria decumbens in Brazil. Veterinary and human toxicology. 2000 Jun; 42(3):142-5. doi: . [PMID: 10839316]
  • S Sen, H P Makkar, S Muetzel, K Becker. Effect of Quillaja saponaria saponins and Yucca schidigera plant extract on growth of Escherichia coli. Letters in applied microbiology. 1998 Jul; 27(1):35-8. doi: 10.1046/j.1472-765x.1998.00379.x. [PMID: 9722995]
  • A T Peana, M D Moretti, V Manconi, G Desole, P Pippia. Anti-inflammatory activity of aqueous extracts and steroidal sapogenins of Agave americana. Planta medica. 1997 Jun; 63(3):199-202. doi: 10.1055/s-2006-957652. [PMID: 9225599]
  • Z Wu, M Sadik, F T Sleiman, J M Simas, M Pessarakli, J T Huber. Influence of yucca extract on ruminal metabolism in cows. Journal of animal science. 1994 Apr; 72(4):1038-42. doi: 10.2527/1994.7241038x. [PMID: 8014138]
  • A Flåøyen, M E di Menna, R G Collin, B L Smith. Cladosporium magnusianum (Jaap) M.B. Ellis is probably not involved in alveld. Veterinary research communications. 1993; 17(3):241-5. doi: 10.1007/bf01839172. [PMID: 7904389]
  • Y Sauvaire, G Ribes, J C Baccou, M M Loubatieères-Mariani. Implication of steroid saponins and sapogenins in the hypocholesterolemic effect of fenugreek. Lipids. 1991 Mar; 26(3):191-7. doi: 10.1007/bf02543970. [PMID: 2046485]
  • B J Camp, C H Bridges, D W Hill, B Patamalai, S Wilson. Isolation of a steroidal sapogenin from the bile of a sheep fed Agave lecheguilla. Veterinary and human toxicology. 1988 Dec; 30(6):533-5. doi: ". [PMID: 3245115]
  • O GISVOLD, L KIER. A note on tigogenin from Digitalis lanata. Journal of the American Pharmaceutical Association. American Pharmaceutical Association. 1956 Aug; 45(8):581. doi: 10.1002/jps.3030450823. [PMID: 13357358]