Periplocin (BioDeep_00000230572)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(3?,5?)-3-[(2,6-Dideoxy-4-O-?-D-glucopyranosyl-3-O-methyl-?-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-card-20(22)-enolide; Periplocin (6CI,7CI,8CI); (3?,5?)-3-[(2,6-Dideoxy-4-O-?-D-glucopyranosyl-3-O-methyl-?-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxycard-20(22)-enolide; Periplocoside; Periplogenin 3-O-[?-D-glucopyranosyl-(1?4)-?-D-cymaropyranoside]

化学式: C36H56O13 (696.3721)
中文名称: 杠柳毒苷
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 83.03%

分子结构信息

SMILES: CC1C(C(CC(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)C)OC)OC7C(C(C(C(O7)CO)O)O)O
InChI: InChI=1S/C36H56O13/c1-18-31(49-32-30(41)29(40)28(39)25(16-37)48-32)24(44-4)14-27(46-18)47-20-5-9-33(2)22-6-10-34(3)21(19-13-26(38)45-17-19)8-12-36(34,43)23(22)7-11-35(33,42)15-20/h13,18,20-25,27-32,37,39-43H,5-12,14-17H2,1-4H3/t18-,20+,21-,22+,23-,24+,25-,27+,28-,29+,30-,31-,32+,33-,34-,35+,36+/m1/s1

描述信息

Origin: Plant; SubCategory_DNP: Triterpenoids
Periplocin is a natural product found in Periploca sepium, Periploca forrestii, and other organisms with data available.
Periplocin is a cardiotonic steroid isolated from root-bark Periploca sepium Bunge. Periplocin promotes tumor cell apoptosis and inhibits tumor growth. Periplocin has the potential to facilitate wound healing through the activation of Src/ERK and PI3K/Akt pathways mediated by Na/K-ATPase[1][2].
Periplocin is a cardiotonic steroid isolated from root-bark Periploca sepium Bunge. Periplocin promotes tumor cell apoptosis and inhibits tumor growth. Periplocin has the potential to facilitate wound healing through the activation of Src/ERK and PI3K/Akt pathways mediated by Na/K-ATPase[1][2].

同义名列表

13 个代谢物同义名

Periplocin; (3?,5?)-3-[(2,6-Dideoxy-4-O-?-D-glucopyranosyl-3-O-methyl-?-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-card-20(22)-enolide; Periplocin (6CI,7CI,8CI); (3?,5?)-3-[(2,6-Dideoxy-4-O-?-D-glucopyranosyl-3-O-methyl-?-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxycard-20(22)-enolide; Periplocoside; Periplogenin 3-O-[?-D-glucopyranosyl-(1?4)-?-D-cymaropyranoside]; 3-[(3S,5S,8R,9S,10R,13R,14S,17R)-5,14-dihydroxy-3-[(2R,4S,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one; CARD-20(22)-ENOLIDE, 3-((2,6-DIDEOXY-4-O-.BETA.-D-GLUCOPYRANOSYL-3-O-METHYL-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-5,14-DIHYDROXY-, (3.BETA.,5.BETA.)-; Card-20(22)-enolide, 3-((2,6-dideoxy-4-O-beta-D-glucopyranosyl-3-O-methyl-beta-D-ribo-hexopyranosyl)oxy)-5,14-dihydroxy-, (3-beta,5-beta)-; Card-20(22)-enolide, 3-[(2,6-dideoxy-4-O-beta-D-glucopyranosyl-3-O-methyl-beta-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-, (3beta,5beta)-; PERIPLOGENIN 3-O-(.BETA.-D-GLUCOPYRANOSYL-(1->4)-.BETA.-D-CYMAROPYRANOSIDE); Periplogenin + D-cymarose + D-glucose [German]; 4-18-00-02439 (Beilstein Handbook Reference); Periplogenin + D-cymarose + D-glucose; Glucoperiplocymarin; PERIPLOCIN [MI]; Periplocoside



数据库引用编号

12 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)

38 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

  • Kui Wang, Shuyue Fu, Lixia Dong, Dingyue Zhang, Mao Wang, Xingyun Wu, Enhao Shen, Li Luo, Changlong Li, Edouard Collins Nice, Canhua Huang, Bingwen Zou. Periplocin suppresses the growth of colorectal cancer cells by triggering LGALS3 (galectin 3)-mediated lysophagy. Autophagy. 2023 Jul; ?(?):1-19. doi: 10.1080/15548627.2023.2239042. [PMID: 37471054]
  • Jia-Peng Lin, Mao-Hua Huang, Zhi-Ting Sun, Lei Chen, Yu-He Lei, Yu-Qing Huang, Ming Qi, Shu-Ran Fan, Shou-Guo Chen, Chi-Wing Chung, Mei-Ching Chan, Jun-Shan Liu, Min Hu, Min-Feng Chen, Wen-Cai Ye, Yue-Yue Chen, Li-Juan Deng. Periplocin inhibits hepatocellular carcinoma progression and reduces the recruitment of MDSCs through AKT/NF-κB pathway. Life sciences. 2023 Jul; 324(?):121715. doi: 10.1016/j.lfs.2023.121715. [PMID: 37100377]
  • Jiameng Hao, Liping Chang, Dandong Wang, Chuanyuan Ji, Shaolan Zhang, Yunlong Hou, Yiling Wu. Periplocin Alleviates Cardiac Remodeling in DOCA-Salt-Induced Heart Failure Rats. Journal of cardiovascular translational research. 2023 02; 16(1):127-140. doi: 10.1007/s12265-022-10277-2. [PMID: 35616880]
  • Shuyao Wang, Xin Yu, Siyang Wu, Wei Yang, Yang Gao, Weihua Wang, Qiutao Wang, Mengmeng Wei, Mingying Zhu, Jiarui Wu, Zheng Yuan, Yingfei Li. Simultaneous determination of periplocin, periplocymarin, periplogenin, periplocoside M and periplocoside N of Cortex Periplocae in rat plasma and its application to a pharmacokinetic study. Biomedical chromatography : BMC. 2022 Mar; 36(3):e5283. doi: 10.1002/bmc.5283. [PMID: 34816469]
  • Huifeng Wang, Zongzheng Zou, Luqin Wan, Junfa Xue, Chen Chen, Bingjie Yu, Zhenzhen Zhang, Lingling Yang, Lixin Xie. Periplocin ameliorates mouse age-related meibomian gland dysfunction through up-regulation of Na/K-ATPase via SRC pathway. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 Feb; 146(?):112487. doi: 10.1016/j.biopha.2021.112487. [PMID: 34883449]
  • Wei Wang, Yuqi Fan, Xuhua Huang, Li Li, Songrui Wang, Zixiang Xue, Huizi Ouyang, Jun He. Metabolomics study on the periplocin-induced cardiotoxicity and the compatibility of periplocin and Panax notoginseng saponins in reducing cardiotoxicity in rats by GC-MS. Journal of separation science. 2021 Jul; 44(14):2785-2797. doi: 10.1002/jssc.202001262. [PMID: 33961332]
  • Muneshige Tokugawa, Yasumichi Inoue, Kan'ichiro Ishiuchi, Chisane Kujirai, Michiyo Matsuno, Masaki Ri, Yuka Itoh, Chiharu Miyajima, Daisuke Morishita, Nobumichi Ohoka, Shinsuke Iida, Hajime Mizukami, Toshiaki Makino, Hidetoshi Hayashi. Periplocin and cardiac glycosides suppress the unfolded protein response. Scientific reports. 2021 05; 11(1):9528. doi: 10.1038/s41598-021-89074-x. [PMID: 33947921]
  • Birgit Lohberger, Susanne Wagner, Juliana Wohlmuther, Heike Kaltenegger, Nicole Stuendl, Andreas Leithner, Beate Rinner, Olaf Kunert, Rudolf Bauer, Nadine Kretschmer. Periplocin, the most anti-proliferative constituent of Periploca sepium, specifically kills liposarcoma cells by death receptor mediated apoptosis. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 Dec; 51(?):162-170. doi: 10.1016/j.phymed.2018.10.008. [PMID: 30466613]
  • Huaming Liu, Dandan Zhang, Zhidan Tang, Mengjie Sun, John Teye Azietaku, Huizi Ouyang, Yanxu Chang, Meng Wang, Jun He, Xiumei Gao. Tissue distribution study of periplocin and its two metabolites in rats by a validated LC-MS/MS method. Biomedical chromatography : BMC. 2018 Oct; 32(10):e4302. doi: 10.1002/bmc.4302. [PMID: 29809276]
  • Aizhu Li, Xuejun Guo, Jiabin Xie, Xinyu Liu, Zhenzhu Zhang, Yubo Li, Yanjun Zhang. Validation of biomarkers in cardiotoxicity induced by Periplocin on neonatal rat cardiomyocytes using UPLC-Q-TOF/MS combined with a support vector machine. Journal of pharmaceutical and biomedical analysis. 2016 May; 123(?):179-85. doi: 10.1016/j.jpba.2016.02.014. [PMID: 26924293]
  • Lei Li, Lian-Mei Zhao, Su-Li Dai, Wen-Xuan Cui, Hui-Lai Lv, Liang Chen, Bao-En Shan. Periplocin Extracted from Cortex Periplocae Induced Apoptosis of Gastric Cancer Cells via the ERK1/2-EGR1 Pathway. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2016; 38(5):1939-51. doi: 10.1159/000445555. [PMID: 27160973]
  • Jun He, Fang Bo, Yaru Tu, John Teye Azietaku, Ting Dou, Huizi Ouyang, Yanxu Chang, Hong Liu, Xiumei Gao. A validated LC-MS/MS assay for the simultaneous determination of periplocin and its two metabolites, periplocymarin and periplogenin in rat plasma: Application to a pharmacokinetic study. Journal of pharmaceutical and biomedical analysis. 2015 Oct; 114(?):292-5. doi: 10.1016/j.jpba.2015.06.008. [PMID: 26093244]
  • Sheng Liang, Fengchun Deng, Haiyan Xing, He Wen, Xiaoyan Shi, Orleans Nii Martey, Emmanuel Koomson, Xin He. P-glycoprotein- and organic anion-transporting polypeptide-mediated transport of periplocin may lead to drug-herb/drug-drug interactions. Drug design, development and therapy. 2014; 8(?):475-83. doi: 10.2147/dddt.s61024. [PMID: 24872678]
  • Jian Zhang, Wenyuan Gao, Juan Wang, Peigen Xiao. [Affect of Ag+ and La3+ elicitors on growth and accumulation of adventitious roots of Periploca sepium]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Jan; 36(1):11-5. doi: 10.4268/cjcmm20110103. [PMID: 21473144]
  • Lixin Yi, Kaishun Bi, Xinyang Chen, Qiufeng Zhang, Shuang Che, Wentao Liu, Dan Lu, Xiaohui Chen. Determination and pharmacokinetics of periplocin in rat plasma by LC-MS. Biomedical chromatography : BMC. 2010 Oct; 24(10):1089-93. doi: 10.1002/bmc.1409. [PMID: 20853463]
  • Jian Zhang, Wenyuan Gao, Xinglin Li, Juan Wang, Limei Li. [Induction of Periploca sepium in vitro plantlet and studies on dynamic accumulation of periplocin]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Sep; 35(18):2392-4. doi: 10.4268/cjcmm20101706. [PMID: 21141484]
  • Xiao-ying Wang, Xiu-mei Gao, Hong Liu, Han Zhang, Yang Liu, Min Jiang, Li-min Hu, Bo-li Zhang. Gene expression profiling of the proliferative effect of periplocin on mouse cardiac microvascular endothelial cells. Chinese journal of integrative medicine. 2010 Feb; 16(1):33-40. doi: 10.1007/s11655-010-0033-z. [PMID: 20131034]
  • Jing Zhang, Bao-En Shan, Qiao-Min Li, Chao Zhang, Rui-Nian Zhao, Jun Ai. [Immunoregulatory effects of periplocin from Cortex Periplocae in tumor-bearing mice]. Xi bao yu fen zi mian yi xue za zhi = Chinese journal of cellular and molecular immunology. 2009 Oct; 25(10):887-90. doi: NULL. [PMID: 19811733]
  • Hong Liu, Hong Yang, Jun-hua Guo, Gui-xiang Pan, Tian-xiang Li, Li-juan Zhang. [Determination of periplocin in different parts of Periploca sepium]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2006 Jul; 29(7):656-7. doi: ". [PMID: 17058999]
  • Hong-Li Guo, Jin-Yun Zhou. [Isolation and structure elucidation of glycosides in n-butanol extracts from rhizome of Periploca calophylla]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2005 Jan; 30(1):44-6. doi: . [PMID: 15714800]