Withanolide A (BioDeep_00000361840)

Main id: BioDeep_00000000864

Secondary id: BioDeep_00000018190

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


(1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one

化学式: C28H38O6 (470.2668248)
中文名称: 睡茄素A
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 2.44%

分子结构信息

SMILES: CC1=C(C(=O)OC(C1)C(C)(C2CCC3C2(CCC4C3C5C(O5)C6(C4(C(=O)C=CC6)C)O)C)O)C
InChI: InChI=1S/C28H38O6/c1-14-13-20(33-24(30)15(14)2)27(5,31)18-9-8-16-21-17(10-12-25(16,18)3)26(4)19(29)7-6-11-28(26,32)23-22(21)34-23/h6-7,16-18,20-23,31-32H,8-13H2,1-5H3

描述信息

Withanolide A is a withanolide.
withanolide A is a natural product found in Withania somnifera, Withania coagulans, and Discopodium penninervium with data available.

同义名列表

19 个代谢物同义名

(1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one; 15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0^{2,4}.0^{5,10}.0^{14,18}]octadec-7-en-9-one; 15-[1-(4,5-Dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one; (20R,22R)-O-(3)-alpha-L-rhamnopyranosyl(1-4)-beta-D-glucopyranosyl-1 alpha,12 beta-diacetoxy-20-hydroxywitha-5,24-dienolide; (5.ALPHA.,6.ALPHA.,7.ALPHA.,22R)-5,20-DIHYDROXY-6,7:22,26-DIEPOXYERGOSTA-2,24-DIENE-1,26-DIONE; (5alpha,6alpha,7alpha,22R)-5,20-Dihydroxy-6,7:22,26-diepoxyergosta-2,24-diene-1,26-dione; 3-rhamnopyranosyl(1-4)-glucopyranosyl-12-diacetoxy-20-hydroxywitha-5,24-dienolide; Withanolide A, United States Pharmacopeia (USP) Reference Standard; Withanolide A, analytical standard; Withanolide A, >=95\\% (HPLC); WITHANOLIDE A [USP-RS]; Withanolide A, (+)-; WITHANOLIDE A(P); Withanolide A; withanolide 1; ST 28:6;O6; 6,7-Epoxy-5,20-dihydroxy-1-oxowitha-2,24-dienolide; (+)-Withanolide A; Withanolide A



数据库引用编号

13 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)

25 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

  • Sandra Soh, Wei-Yi Ong. Effect of Withanolide A on 7-Ketocholesterol Induced Cytotoxicity in hCMEC/D3 Brain Endothelial Cells. Cells. 2022 01; 11(3):. doi: 10.3390/cells11030457. [PMID: 35159267]
  • Priya Pathak, Prachi Shukla, Jitendra S Kanshana, Kumaravelu Jagavelu, Neelam S Sangwan, Anil K Dwivedi, Madhu Dikshit. Standardized root extract of Withania somnifera and Withanolide A exert moderate vasorelaxant effect in the rat aortic rings by enhancing nitric oxide generation. Journal of ethnopharmacology. 2021 Oct; 278(?):114296. doi: 10.1016/j.jep.2021.114296. [PMID: 34090907]
  • Janine Naß, Sara Abdelfatah, Thomas Efferth. Induction of stress resistance and extension of lifespan in Chaenorhabditis elegans serotonin-receptor knockout strains by withanolide A. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 Apr; 84(?):153482. doi: 10.1016/j.phymed.2021.153482. [PMID: 33611213]
  • Shreya Dubey, Monika Kallubai, Rajagopal Subramanyam. Improving the inhibition of β-amyloid aggregation by withanolide and withanoside derivatives. International journal of biological macromolecules. 2021 Mar; 173(?):56-65. doi: 10.1016/j.ijbiomac.2021.01.094. [PMID: 33465364]
  • Raman Preet, Raghbir Chand Gupta. Quantification of withaferin-A and withanolide-A in diploid (n = 12) and tetraploid cytotypes (n = 24) of "Rassbhary", Physalis angulata L. Natural product research. 2019 Nov; 33(21):3157-3160. doi: 10.1080/14786419.2018.1519815. [PMID: 30445854]
  • Sil Kim, Jae Sik Yu, Ji Young Lee, Sang Un Choi, Jeongmi Lee, Ki Hyun Kim. Cytotoxic Withanolides from the Roots of Indian Ginseng ( Withania somnifera). Journal of natural products. 2019 04; 82(4):765-773. doi: 10.1021/acs.jnatprod.8b00665. [PMID: 30776236]
  • Ramesh Kumar Kushwaha, Sucheta Singh, Shiv Shanker Pandey, Alok Kalra, Chikkarasanahalli Shivegowda Vivek Babu. Innate endophytic fungus, Aspergillus terreus as biotic elicitor of withanolide A in root cell suspension cultures of Withania somnifera. Molecular biology reports. 2019 Apr; 46(2):1895-1908. doi: 10.1007/s11033-019-04641-w. [PMID: 30706360]
  • Ramesh Kumar Kushwaha, Sucheta Singh, Shiv Shanker Pandey, Alok Kalra, C S Vivek Babu. Fungal endophytes attune withanolide biosynthesis in Withania somnifera, prime to enhanced withanolide A content in leaves and roots. World journal of microbiology & biotechnology. 2019 Jan; 35(2):20. doi: 10.1007/s11274-019-2593-1. [PMID: 30656434]
  • Niraj Tripathi, Divya Shrivastava, Bilal Ahmad Mir, Shailesh Kumar, Sumit Govil, Maryam Vahedi, Prakash S Bisen. Metabolomic and biotechnological approaches to determine therapeutic potential of Withania somnifera (L.) Dunal: A review. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 Nov; 50(?):127-136. doi: 10.1016/j.phymed.2017.08.020. [PMID: 30466971]
  • Satyanshu Kumar, Raghuraj Singh, Narendra Gajbhiye, Tushar Dhanani. Extraction Optimization for Phenolic- and Withanolide-Rich Fractions from Withania somnifera Roots: Identification and Quantification of Withaferin A, 12-Deoxywithastromonolide, and Withanolide A in Plant Materials and Marketed Formulations Using a Reversed-Phase HPLC-Photodiode Array Detection Method. Journal of AOAC International. 2018 Nov; 101(6):1773-1780. doi: 10.5740/jaoacint.18-0081. [PMID: 29945694]
  • Sandeep K Singh, Guru R Valicherla, Pankaj Joshi, Sudhir Shahi, Anees A Syed, Anand P Gupta, Zakir Hossain, Kishan Italiya, Vishal Makadia, Shio K Singh, Mohammad Wahajuddin, Jiaur R Gayen. Determination of permeability, plasma protein binding, blood partitioning, pharmacokinetics and tissue distribution of Withanolide A in rats: A neuroprotective steroidal lactone. Drug development research. 2018 11; 79(7):339-351. doi: 10.1002/ddr.21463. [PMID: 30284738]
  • Bashir Akhlaq Akhoon, Laxmi Rathor, Rakesh Pandey. Withanolide A extends the lifespan in human EGFR-driven cancerous Caenorhabditis elegans. Experimental gerontology. 2018 04; 104(?):113-117. doi: 10.1016/j.exger.2018.02.004. [PMID: 29427754]
  • Shreya Dubey, Monika Kallubai, Arijit Sarkar, Rajagopal Subramanyam. Elucidating the active interaction mechanism of phytochemicals withanolide and withanoside derivatives with human serum albumin. PloS one. 2018; 13(11):e0200053. doi: 10.1371/journal.pone.0200053. [PMID: 30403672]
  • Amandeep Kaur, Baldev Singh, Puja Ohri, Jia Wang, Renu Wadhwa, Sunil C Kaul, Pratap Kumar Pati, Arvinder Kaur. Organic cultivation of Ashwagandha with improved biomass and high content of active Withanolides: Use of Vermicompost. PloS one. 2018; 13(4):e0194314. doi: 10.1371/journal.pone.0194314. [PMID: 29659590]
  • Ya-ming Xu, Daniel P Bunting, Manping X Liu, Hema A Bandaranayake, A A Leslie Gunatilaka. 17β-Hydroxy-18-acetoxywithanolides from Aeroponically Grown Physalis crassifolia and Their Potent and Selective Cytotoxicity for Prostate Cancer Cells. Journal of natural products. 2016 Apr; 79(4):821-30. doi: 10.1021/acs.jnatprod.5b00911. [PMID: 27071003]
  • Syed Saema, Laiq Ur Rahman, Ruchi Singh, Abhishek Niranjan, Iffat Zareen Ahmad, Pratibha Misra. Ectopic overexpression of WsSGTL1, a sterol glucosyltransferase gene in Withania somnifera, promotes growth, enhances glycowithanolide and provides tolerance to abiotic and biotic stresses. Plant cell reports. 2016 Jan; 35(1):195-211. doi: 10.1007/s00299-015-1879-5. [PMID: 26518426]
  • Manuel Candelario, Erika Cuellar, Jorge Mauricio Reyes-Ruiz, Narek Darabedian, Zhou Feimeng, Ricardo Miledi, Amelia Russo-Neustadt, Agenor Limon. Direct evidence for GABAergic activity of Withania somnifera on mammalian ionotropic GABAA and GABAρ receptors. Journal of ethnopharmacology. 2015 Aug; 171(?):264-72. doi: 10.1016/j.jep.2015.05.058. [PMID: 26068424]
  • Feng-Ying Wang, Yi-Ming Sun, Cui-Ping Lv, Meng-Qi Cheng, Lai Zhang, Min Sun. [Hair roots induction and culture of Withania somnifera and its withanolide A synthesis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2014 Mar; 39(5):790-4. doi: ". [PMID: 25204166]
  • Abhinav Grover, Gaurav Samuel, Virendra S Bisaria, Durai Sundar. Enhanced withanolide production by overexpression of squalene synthase in Withania somnifera. Journal of bioscience and bioengineering. 2013 Jun; 115(6):680-5. doi: 10.1016/j.jbiosc.2012.12.011. [PMID: 23313565]
  • Dada Patil, Manish Gautam, Sanjay Mishra, Suresh Karupothula, Sunil Gairola, Suresh Jadhav, Shrikrishna Pawar, Bhushan Patwardhan. Determination of withaferin A and withanolide A in mice plasma using high-performance liquid chromatography-tandem mass spectrometry: application to pharmacokinetics after oral administration of Withania somnifera aqueous extract. Journal of pharmaceutical and biomedical analysis. 2013 Jun; 80(?):203-12. doi: 10.1016/j.jpba.2013.03.001. [PMID: 23584079]
  • Farzana Sabir, Smrati Mishra, Rajender S Sangwan, Jyoti S Jadaun, Neelam S Sangwan. Qualitative and quantitative variations in withanolides and expression of some pathway genes during different stages of morphogenesis in Withania somnifera Dunal. Protoplasma. 2013 Apr; 250(2):539-49. doi: 10.1007/s00709-012-0438-y. [PMID: 22878597]
  • H N Murthy, N Praveen. Carbon sources and medium pH affects the growth of Withania somnifera (L.) Dunal adventitious roots and withanolide A production. Natural product research. 2013; 27(2):185-9. doi: 10.1080/14786419.2012.660691. [PMID: 22394118]
  • Smijin Soman, P K Korah, S Jayanarayanan, Jobin Mathew, C S Paulose. Oxidative stress induced NMDA receptor alteration leads to spatial memory deficits in temporal lobe epilepsy: ameliorative effects of Withania somnifera and Withanolide A. Neurochemical research. 2012 Sep; 37(9):1915-27. doi: 10.1007/s11064-012-0810-5. [PMID: 22700086]
  • Madhavi Doma, Gauri Abhayankar, V D Reddy, P B Kavi Kishor. Carbohydrate and elicitor enhanced withanolide (withaferin A and withanolide A) accumulation in hairy root cultures of Withania somnifera (L.). Indian journal of experimental biology. 2012 Jul; 50(7):484-90. doi: ". [PMID: 22822528]
  • Praveen Nagella, Hosakatte Niranjana Murthy. Establishment of cell suspension cultures of Withania somnifera for the production of withanolide A. Bioresource technology. 2010 Sep; 101(17):6735-9. doi: 10.1016/j.biortech.2010.03.078. [PMID: 20371175]
  • Sachin P Patil, Sarah Maki, Santosh A Khedkar, Alan C Rigby, Christina Chan. Withanolide A and asiatic acid modulate multiple targets associated with amyloid-beta precursor protein processing and amyloid-beta protein clearance. Journal of natural products. 2010 Jul; 73(7):1196-202. doi: 10.1021/np900633j. [PMID: 20553006]
  • Dada Patil, Manish Gautam, Umesh Jadhav, Sanjay Mishra, Suresh Karupothula, Sunil Gairola, Suresh Jadhav, Bhushan Patwardhan. Physicochemical stability and biological activity of Withania somnifera extract under real-time and accelerated storage conditions. Planta medica. 2010 Mar; 76(5):481-8. doi: 10.1055/s-0029-1186220. [PMID: 19844862]
  • Navjot Shah, Hardeep Kataria, Sunil C Kaul, Tetsuro Ishii, Gurcharan Kaur, Renu Wadhwa. Effect of the alcoholic extract of Ashwagandha leaves and its components on proliferation, migration, and differentiation of glioblastoma cells: combinational approach for enhanced differentiation. Cancer science. 2009 Sep; 100(9):1740-7. doi: 10.1111/j.1349-7006.2009.01236.x. [PMID: 19575749]
  • Kiranjeet Kour, Anjali Pandey, K A Suri, N K Satti, K K Gupta, Sarang Bani. Restoration of stress-induced altered T cell function and corresponding cytokines patterns by Withanolide A. International immunopharmacology. 2009 Sep; 9(10):1137-44. doi: 10.1016/j.intimp.2009.05.011. [PMID: 19524704]
  • Hosakatte N Murthy, Camelia Dijkstra, Paul Anthony, Daniel A White, Mike R Davey, J Brian Power, Eun J Hahn, Kee Y Paek. Establishment of Withania somnifera hairy root cultures for the production of withanolide A. Journal of integrative plant biology. 2008 Aug; 50(8):975-81. doi: 10.1111/j.1744-7909.2008.00680.x. [PMID: 18713347]
  • Chihiro Tohda. [Overcoming several neurodegenerative diseases by traditional medicines: the development of therapeutic medicines and unraveling pathophysiological mechanisms]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2008 Aug; 128(8):1159-67. doi: 10.1248/yakushi.128.1159. [PMID: 18670181]
  • Rajender Singh Sangwan, Narayan Das Chaurasiya, Payare Lal, Laxminarain Misra, Rakesh Tuli, Neelam Singh Sangwan. Withanolide A is inherently de novo biosynthesized in roots of the medicinal plant Ashwagandha (Withania somnifera). Physiologia plantarum. 2008 Jun; 133(2):278-87. doi: 10.1111/j.1399-3054.2008.01076.x. [PMID: 18312497]
  • Farzana Sabir, Neelam S Sangwan, Narayan D Chaurasiya, Laxmi N Misra, Rajender S Sangwan. In vitro withanolide production by Withania somnifera L. cultures. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2008 May; 63(5-6):409-12. doi: 10.1515/znc-2008-5-616. [PMID: 18669028]
  • Rajender Singh Sangwan, Narayan Das Chaurasiya, Payare Lal, Laxminarain Misra, Girish Chandra Uniyal, Rakesh Tuli, Neelam Singh Sangwan. Withanolide A biogeneration in in vitro shoot cultures of ashwagandha (Withania somnifera DUNAL), a main medicinal plant in Ayurveda. Chemical & pharmaceutical bulletin. 2007 Sep; 55(9):1371-5. doi: 10.1248/cpb.55.1371. [PMID: 17827764]
  • Mary Kaileh, Wim Vanden Berghe, Arne Heyerick, Julie Horion, Jacques Piette, Claude Libert, Denis De Keukeleire, Tamer Essawi, Guy Haegeman. Withaferin a strongly elicits IkappaB kinase beta hyperphosphorylation concomitant with potent inhibition of its kinase activity. The Journal of biological chemistry. 2007 Feb; 282(7):4253-4264. doi: 10.1074/jbc.m606728200. [PMID: 17150968]
  • Bolleddula Jayaprakasam, Yanjun Zhang, Navindra P Seeram, Muraleedharan G Nair. Growth inhibition of human tumor cell lines by withanolides from Withania somnifera leaves. Life sciences. 2003 Nov; 74(1):125-32. doi: 10.1016/j.lfs.2003.07.007. [PMID: 14575818]
  • Jing Zhao, Norio Nakamura, Masao Hattori, Tomoharu Kuboyama, Chihiro Tohda, Katsuko Komatsu. Withanolide derivatives from the roots of Withania somnifera and their neurite outgrowth activities. Chemical & pharmaceutical bulletin. 2002 Jun; 50(6):760-5. doi: 10.1248/cpb.50.760. [PMID: 12045329]
  • J A Bravo B, M Sauvain, A Gimenez T, E Balanza, L Serani, O Laprévote, G Massiot, C Lavaud. Trypanocidal withanolides and withanolide glycosides from Dunalia brachyacantha. Journal of natural products. 2001 Jun; 64(6):720-5. doi: 10.1021/np000527p. [PMID: 11421731]
  • H Matsuda, T Murakami, A Kishi, M Yoshikawa. Structures of withanosides I, II, III, IV, V, VI, and VII, new withanolide glycosides, from the roots of Indian Withania somnifera DUNAL. and inhibitory activity for tachyphylaxis to clonidine in isolated guinea-pig ileum. Bioorganic & medicinal chemistry. 2001 Jun; 9(6):1499-507. doi: 10.1016/s0968-0896(01)00024-4. [PMID: 11408168]