Silidianin (BioDeep_00000230328)

 

Secondary id: BioDeep_00000286204

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(3R,8R) -2,3,3abeta,7a-Tetrahydro-7abeta-hydroxy-8- (4-hydroxy-3-methoxyphenyl) -4- [ (2R,3R) -3,5,7-trihydroxy-3,4-dihydro-4-oxo-2H-1-benzopyran-2-yl ] -3alpha,6alpha-methanobenzofuran-7 (6H) -one

化学式: C25H22O10 (482.1213)
中文名称: 水飞蓟宁
谱图信息: 最多检出来源 Astragalus membranaceus(otcml) 100%

分子结构信息

SMILES: c(O)(c(OC)6)ccc(c6)[C@@](C=32)([C@@](C1)([C@](CC3[C@@H](O5)[C@H](C(=O)c(c54)c(cc(O)c4)O)O)([H])[C@](O)(C2=O)O1)[H])[H]
InChI: InChI=1S/C25H22O10/c1-33-16-4-9(2-3-14(16)27)18-11-7-12(20-13(18)8-34-25(20,32)24(11)31)23-22(30)21(29)19-15(28)5-10(26)6-17(19)35-23/h2-7,11,13,18,20,22-23,26-28,30,32H,8H2,1H3

描述信息

Silidianin is a natural product found in Silybum eburneum and Silybum marianum with data available.
C26170 - Protective Agent > C2081 - Hepatoprotective Agent
Silydianin is an active constituent of Silybium marianum, with exhibit anti-collagenase, antitumor and anti-elastase activities. Silydianin is a natural protein tyrosine phosphatase 1B (PTP1B) with an IC50 of 17.38?μM. Silydianin has inhibitory effect on the in vitro production and release of oxidative products[1][2][3].
Silydianin is an active constituent of Silybium marianum, with exhibit anti-collagenase, antitumor and anti-elastase activities. Silydianin is a natural protein tyrosine phosphatase 1B (PTP1B) with an IC50 of 17.38?μM. Silydianin has inhibitory effect on the in vitro production and release of oxidative products[1][2][3].

同义名列表

21 个代谢物同义名

Silidianin; Silydianin; (+)-2,3.ALPHA.,3A.ALPHA.A,7A-TETRAHYDRO-7A.ALPHA.-HYDROXY-8-(4-HYDROXY-3-METHOXYPHENYL)-4-(3.ALPHA.,5,7-TRIHYDROXY-4-OXO-2.BETA.-CHROMANYL)-3,6-METHANOBENZOFURAN-7(6.ALPHA.H)-ONE; (+)-2,3 alpha,3a alpha,7a-tetrahydro-7aalpha-hydroxy-8-(4-hydroxy-3-methoxyphenyl)-4-(3alpha,5,7-trihydroxy-4-oxo-2beta-chromanyl)-3,6-methanobenzofuran-7(6alphaH)-one; (+)-2,3alpha,3aalpha,7a-Tetrahydro-7aalpha-hydroxy-8-(4-hydroxy-3-methoxyphenyl)-4-(3alpha,5,7-trihydroxy-4-oxo-2beta-chromanyl)-3,6-methanobenzofuran-7(6alphaH)-one; (3R,3aR,6R,7aR,8R)-7a-Hydroxy-8-(4-hydroxy-3-methoxyphenyl)-4-((2R,3R)-3,5,7-trihydroxy-4-oxochroman-2-yl)-3,3a,6,7a-tetrahydro-3,6-methanobenzofuran-7(2H)-one; (1S,3S,6R,7S,10R)-3-Hydroxy-10-(4-hydroxy-3-methoxyphenyl)-8-[(2R,3R)-3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-one; (1R,3R,6R,7R,10R)-3-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-8-[(2R,3R)-3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-one; Silydianin, United States Pharmacopeia (USP) Reference Standard; SILIDIANIN (CONSTITUENT OF MILK THISTLE) [DSC]; Silydianin, analytical standard; Silidianina [INN-Spanish]; Silidianinum [INN-Latin]; Silidianine [INN-French]; SILYDIANIN [USP-RS]; SILIDIANIN [MART.]; Silidianin [INN]; UNII-7P89L7W179; silidianine; 7P89L7W179; (3R,8R) -2,3,3abeta,7a-Tetrahydro-7abeta-hydroxy-8- (4-hydroxy-3-methoxyphenyl) -4- [ (2R,3R) -3,5,7-trihydroxy-3,4-dihydro-4-oxo-2H-1-benzopyran-2-yl ] -3alpha,6alpha-methanobenzofuran-7 (6H) -one



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)

15 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


文献列表

  • Entezar Mehrabi Nasab, Seyyede Masoume Athari, Saadat Ghafarzade, Abdol-Rahman Mehrabi Nasab, Seyyed Shamsadin Athari. Immunomodulatory effects of two silymarin isomers in a Balb/c mouse model of allergic asthma. Allergologia et immunopathologia. 2020 Nov; 48(6):646-653. doi: 10.1016/j.aller.2020.01.003. [PMID: 32284261]
  • Xin Wang, Zhen Zhang, Shuai-Cheng Wu. Health Benefits of Silybum marianum: Phytochemistry, Pharmacology, and Applications. Journal of agricultural and food chemistry. 2020 Oct; 68(42):11644-11664. doi: 10.1021/acs.jafc.0c04791. [PMID: 33045827]
  • Jiří Vrba, Barbora Papoušková, Kateřina Lněničková, Pavel Kosina, Vladimír Křen, Jitka Ulrichová. Identification of UDP-glucuronosyltransferases involved in the metabolism of silymarin flavonolignans. Journal of pharmaceutical and biomedical analysis. 2020 Jan; 178(?):112972. doi: 10.1016/j.jpba.2019.112972. [PMID: 31727359]
  • Ji Yeong Kim, Jeong Yoon Kim, Janar Jenis, Zuo Peng Li, Yeong Jun Ban, Aizhamal Baiseitova, Ki Hun Park. Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle). Bioorganic & medicinal chemistry. 2019 06; 27(12):2499-2507. doi: 10.1016/j.bmc.2019.03.013. [PMID: 30871862]
  • Michal Bijak, Rafal Szelenberger, Angela Dziedzic, Joanna Saluk-Bijak. Inhibitory Effect of Flavonolignans on the P2Y12 Pathway in Blood Platelets. Molecules (Basel, Switzerland). 2018 Feb; 23(2):. doi: 10.3390/molecules23020374. [PMID: 29439388]
  • Michal Bijak, Ewelina Synowiec, Przemyslaw Sitarek, Tomasz Sliwiński, Joanna Saluk-Bijak. Evaluation of the Cytotoxicity and Genotoxicity of Flavonolignans in Different Cellular Models. Nutrients. 2017 Dec; 9(12):. doi: 10.3390/nu9121356. [PMID: 29240674]
  • Michal Bijak, Joanna Saluk-Bijak. Flavonolignans inhibit the arachidonic acid pathway in blood platelets. BMC complementary and alternative medicine. 2017 Aug; 17(1):396. doi: 10.1186/s12906-017-1897-7. [PMID: 28797264]
  • Lenka Roubalová, Albena T Dinkova-Kostova, David Biedermann, Vladimír Křen, Jitka Ulrichová, Jiří Vrba. Flavonolignan 2,3-dehydrosilydianin activates Nrf2 and upregulates NAD(P)H:quinone oxidoreductase 1 in Hepa1c1c7 cells. Fitoterapia. 2017 Jun; 119(?):115-120. doi: 10.1016/j.fitote.2017.04.012. [PMID: 28450126]
  • Sameh F AbouZid, Hayam S Ahmed, Abeer S Moawad, Asmaa I Owis, Shao-Nong Chen, Amandine Nachtergael, James B McAlpine, J Brent Friesen, Guido F Pauli. Chemotaxonomic and biosynthetic relationships between flavonolignans produced by Silybum marianum populations. Fitoterapia. 2017 Jun; 119(?):175-184. doi: 10.1016/j.fitote.2017.04.002. [PMID: 28392269]
  • Jakub Fibigr, Dalibor Šatínský, Petr Solich. A new approach to the rapid separation of isomeric compounds in a Silybum marianum extract using UHPLC core-shell column with F5 stationary phase. Journal of pharmaceutical and biomedical analysis. 2017 Feb; 134(?):203-213. doi: 10.1016/j.jpba.2016.11.042. [PMID: 27915198]
  • Michaela Pyszková, Michal Biler, David Biedermann, Kateřina Valentová, Marek Kuzma, Jiří Vrba, Jitka Ulrichová, Romana Sokolová, Miloš Mojović, Ana Popović-Bijelić, Martin Kubala, Patrick Trouillas, Vladimír Křen, Jan Vacek. Flavonolignan 2,3-dehydroderivatives: Preparation, antiradical and cytoprotective activity. Free radical biology & medicine. 2016 Jan; 90(?):114-25. doi: 10.1016/j.freeradbiomed.2015.11.014. [PMID: 26582372]
  • Naila Ben Rahal, Francisco J Barba, Danielle Barth, Isabelle Chevalot. Supercritical CO₂ extraction of oil, fatty acids and flavonolignans from milk thistle seeds: Evaluation of their antioxidant and cytotoxic activities in Caco-2 cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2015 Sep; 83(?):275-82. doi: 10.1016/j.fct.2015.07.006. [PMID: 26172510]
  • Reza Keshavarz Afshar, Mohammad Reza Chaichi, Mahya Ansari Jovini, Emad Jahanzad, Masoud Hashemi. Accumulation of silymarin in milk thistle seeds under drought stress. Planta. 2015 Sep; 242(3):539-43. doi: 10.1007/s00425-015-2265-9. [PMID: 25708739]
  • Eva-Maria Pferschy-Wenzig, Atanas G Atanasov, Clemens Malainer, Stefan M Noha, Olaf Kunert, Daniela Schuster, Elke H Heiss, Nicholas H Oberlies, Hildebert Wagner, Rudolf Bauer, Verena M Dirsch. Identification of isosilybin a from milk thistle seeds as an agonist of peroxisome proliferator-activated receptor gamma. Journal of natural products. 2014 Apr; 77(4):842-7. doi: 10.1021/np400943b. [PMID: 24597776]
  • Hao-Jie Zhu, Bryan J Brinda, Kenneth D Chavin, Hilary J Bernstein, Kennerly S Patrick, John S Markowitz. An assessment of pharmacokinetics and antioxidant activity of free silymarin flavonolignans in healthy volunteers: a dose escalation study. Drug metabolism and disposition: the biological fate of chemicals. 2013 Sep; 41(9):1679-85. doi: 10.1124/dmd.113.052423. [PMID: 23835761]
  • Masumeh Khalili, Tahereh Hasanloo, Seyyed Kamal Kazemi Tabar, Hassan Rahnama. Influence of exogenous salicylic acid on flavonolignans and lipoxygenase activity in the hairy root cultures of Silybum marianum. Cell biology international. 2009 Sep; 33(9):988-94. doi: 10.1016/j.cellbi.2009.06.003. [PMID: 19524695]
  • James I Lee, Mahesh Narayan, Jeffrey S Barrett. Analysis and comparison of active constituents in commercial standardized silymarin extracts by liquid chromatography-electrospray ionization mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2007 Jan; 845(1):95-103. doi: 10.1016/j.jchromb.2006.07.063. [PMID: 16942922]
  • James I Lee, Bih H Hsu, Di Wu, Jeffrey S Barrett. Separation and characterization of silybin, isosilybin, silydianin and silychristin in milk thistle extract by liquid chromatography-electrospray tandem mass spectrometry. Journal of chromatography. A. 2006 May; 1116(1-2):57-68. doi: 10.1016/j.chroma.2006.03.053. [PMID: 16631762]
  • Małgorzata Zielińska-Przyjemska, Krzysztof Wiktorowicz. An in vitro study of the protective effect of the flavonoid silydianin against reactive oxygen species. Phytotherapy research : PTR. 2006 Feb; 20(2):115-9. doi: 10.1002/ptr.1812. [PMID: 16444663]
  • Roman Zuber, Martin Modrianský, Zdenek Dvorák, Petr Rohovský, Jitka Ulrichová, Vilím Simánek, Pavel Anzenbacher. Effect of silybin and its congeners on human liver microsomal cytochrome P450 activities. Phytotherapy research : PTR. 2002 Nov; 16(7):632-8. doi: 10.1002/ptr.1000. [PMID: 12410543]
  • E Bosisio, C Benelli, O Pirola. Effect of the flavanolignans of Silybum marianum L. on lipid peroxidation in rat liver microsomes and freshly isolated hepatocytes. Pharmacological research. 1992 Feb; 25(2):147-54. doi: 10.1016/1043-6618(92)91383-r. [PMID: 1635893]