Silybin B2 (BioDeep_00000396886)

Main id: BioDeep_00000412895

 

PANOMIX_OTCML-2023


代谢物信息卡片


4H-1-Benzopyran-4-one, 2-((2R,3R)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-1,4-benzodioxin-6-yl)-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-

化学式: C25H22O10 (482.1212912)
中文名称: 异水飞蓟宾A
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1(O)C=C(O)C2C(=O)[C@H](O)[C@](C3=CC4O[C@H](CO)[C@@H](C5=CC=C(O)C(OC)=C5)OC=4C=C3)([H])OC=2C=1
InChI: InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-18-7-12(3-5-16(18)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23+,24-,25-/m1/s1

描述信息

Isosilybin A is a natural product found in Aspergillus iizukae, Anastatica hierochuntica, and Silybum marianum with data available.
See also: Milk Thistle (part of).
Isosilybin A, a flavonolignan isolated from silymarin, has anti-prostate cancer (PCA) activity. Isosilybin A inhibits proliferation and induces G1 phase arrest and apoptosis in cancer cells, which activates apoptotic machinery in PCA cells via targeting Akt-NF-κB-androgen receptor (AR) axis[1][2].
Isosilybin A, a flavonolignan isolated from silymarin, has anti-prostate cancer (PCA) activity. Isosilybin A inhibits proliferation and induces G1 phase arrest and apoptosis in cancer cells, which activates apoptotic machinery in PCA cells via targeting Akt-NF-κB-androgen receptor (AR) axis[1][2].

同义名列表

16 个代谢物同义名

4H-1-Benzopyran-4-one, 2-((2R,3R)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-1,4-benzodioxin-6-yl)-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-; (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one; (2R,3R)-3,5,7-Trihydroxy-2-((2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one; (2R,3R)-3,5,7-Trihydroxy-2-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydrobenzo[1,4]dioxin-6-yl]-4-chromanone; ISOSILYBIN A (CONSTITUENT OF MILK THISTLE) [DSC]; ISOSILYBIN A (CONSTITUENT OF MILK THISTLE); 7-(4-bromobenzoyl)isosilybin A; ISOSILYBIN A [MI]; Isosilybin A + B; UNII-HHN3Q9H3DK; Isosilibinin A; Iso-silybin A; Isosilybin A; isosilybin B; Silybin B2; HHN3Q9H3DK



数据库引用编号

7 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)

5 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

  • 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]
  • 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]
  • 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]
  • Marina Kawaguchi-Suzuki, Reginald F Frye, Hao-Jie Zhu, Bryan J Brinda, Kenneth D Chavin, Hilary J Bernstein, John S Markowitz. The effects of milk thistle (Silybum marianum) on human cytochrome P450 activity. Drug metabolism and disposition: the biological fate of chemicals. 2014 Oct; 42(10):1611-6. doi: 10.1124/dmd.114.057232. [PMID: 25028567]
  • 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]
  • Tamam El-Elimat, Huzefa A Raja, Tyler N Graf, Stanley H Faeth, Nadja B Cech, Nicholas H Oberlies. Flavonolignans from Aspergillus iizukae, a fungal endophyte of milk thistle (Silybum marianum). Journal of natural products. 2014 Feb; 77(2):193-9. doi: 10.1021/np400955q. [PMID: 24456525]
  • 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]
  • Gagan Deep, Subhash Chander Gangar, Subapriya Rajamanickam, Komal Raina, Mallikarjuna Gu, Chapla Agarwal, Nicholas H Oberlies, Rajesh Agarwal. Angiopreventive efficacy of pure flavonolignans from milk thistle extract against prostate cancer: targeting VEGF-VEGFR signaling. PloS one. 2012; 7(4):e34630. doi: 10.1371/journal.pone.0034630. [PMID: 22514647]
  • Arlene Sy-Cordero, Tyler N Graf, Yuka Nakanishi, Mansukh C Wani, Rajesh Agarwal, David J Kroll, Nicholas H Oberlies. Large-scale isolation of flavonolignans from Silybum marianum extract affords new minor constituents and preliminary structure-activity relationships. Planta medica. 2010 Apr; 76(6):644-7. doi: 10.1055/s-0029-1240624. [PMID: 19941262]
  • Souichi Nakashima, Hisashi Matsuda, Yoshimi Oda, Seikou Nakamura, Fengming Xu, Masayuki Yoshikawa. Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells. Bioorganic & medicinal chemistry. 2010 Mar; 18(6):2337-2345. doi: 10.1016/j.bmc.2010.01.046. [PMID: 20189399]