Pseudolaric (BioDeep_00000230863)
Main id: BioDeep_00000230217
PANOMIX_OTCML-2023
代谢物信息卡片
(2E,4E)-5-[(1S,7S,8S,9R)-7-Acetyloxy-4-methoxycarbonyl-9-methyl-11-oxo-10-oxatricyclo[6.3.2.01,7]tridec-3-en-9-yl]-2-methylpenta-2,4-dienoic acid
化学式: C23H28O8 (432.1784088)
中文名称: 土荆皮乙酸, 土槿皮乙酸
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(=CC=CC1(C2CCC3(C2(CCC(=CC3)C(=O)OC)OC(=O)C)C(=O)O1)C)C(=O)O
InChI: InChI=1S/C23H28O8/c1-14(18(25)26)6-5-10-21(3)17-9-12-22(20(28)31-21)11-7-16(19(27)29-4)8-13-23(17,22)30-15(2)24/h5-7,10,17H,8-9,11-13H2,1-4H3,(H,25,26)/b10-5+,14-6+/t17-,21+,22-,23-/m0/s1
描述信息
Pseudolaric acid B is a diterpene lactone.
CID 71307573 is a natural product found in Pseudolarix amabilis and Larix kaempferi with data available.
Pseudolaric Acid B is a diterpene isolated from the root of Pseudolarix kaempferi (pinaceae), has anti-cancer, antifungal, and antifertile activities, and shows immunosuppressive activity on T lymphocytes[1][2][3]. Pseudolaric Acid B inhibits hepatitis B virus (HBV) secretion through apoptosis and cell cycle arrest. Pseudolaric Acid B induces autophagy[4][5].
Pseudolaric Acid B is a diterpene isolated from the root of Pseudolarix kaempferi (pinaceae), has anti-cancer, antifungal, and antifertile activities, and shows immunosuppressive activity on T lymphocytes[1][2][3]. Pseudolaric Acid B inhibits hepatitis B virus (HBV) secretion through apoptosis and cell cycle arrest. Pseudolaric Acid B induces autophagy[4][5].
同义名列表
数据库引用编号
6 个数据库交叉引用编号
- ChEBI: CHEBI:189471
- PubChem: 71307573
- MeSH: pseudolaric acid B
- chemspider: 4940862
- CAS: 82508-31-4
- medchemexpress: HY-N6939
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)
3 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
- Yu'e Miao, Qiao Yin, Lifeng Ping, Huan Sheng, Jin Chang, Wentong Li, Shijun Lv. Pseudolaric acid B triggers ferritinophagy and ferroptosis via upregulating NCOA4 in lung adenocarcinoma cells.
Journal of cancer research and therapeutics.
2023 Dec; 19(6):1646-1653. doi:
10.4103/jcrt.jcrt_806_23. [PMID: 38156933] - Ke Yang, Jun-Qi Wang, Kai Li, Su-Ning Chen, Fei Yu. Pseudolaric acid B induces apoptosis associated with the mitochondrial and PI3K/AKT/mTOR pathways in triple‑negative breast cancer.
Oncology reports.
2023 Nov; 50(5):. doi:
10.3892/or.2023.8630. [PMID: 37711030] - Liling Jiang, Chuangyu Wen, Qingyan He, Yuening Sun, Jinxiang Wang, Xiaoying Lan, Sagar Rohondia, Q Ping Dou, Xianping Shi, Jinbao Liu. Pseudolaric acid B induces mitotic arrest and apoptosis in both imatinib-sensitive and -resistant chronic myeloid leukaemia cells.
European journal of pharmacology.
2020 Jun; 876(?):173064. doi:
10.1016/j.ejphar.2020.173064. [PMID: 32179085] - Su-Jung Choi, Chi-Hyun Ahn, In-Hyoung Yang, Bohwan Jin, Won Woo Lee, Ji-Hoon Kim, Min-Hye Ahn, Neeti Swarup, Kyoung-Ok Hong, Ji-Ae Shin, Nam-Tae Woo, Seong Doo Hong, Jae-Il Lee, Sung-Dae Cho. Pseudolaric Acid B Induces Growth Inhibition and Caspase-Dependent Apoptosis on Head and Neck Cancer Cell lines through Death Receptor 5.
Molecules (Basel, Switzerland).
2019 Oct; 24(20):. doi:
10.3390/molecules24203715. [PMID: 31623058] - Hai Zhang, Jia-Chuan Li, Han Luo, Lin Zhao, Zhi-Dan Zhang, Xiao-Fei Shen. Pseudolaric acid B exhibits anti-cancer activity on human hepatocellular carcinoma through inhibition of multiple carcinogenic signaling pathways.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2019 Jun; 59(?):152759. doi:
10.1016/j.phymed.2018.11.019. [PMID: 31004883] - Zongqi Wang, Ye Ding, Xuanzhong Wang, Shan Lu, Chongcheng Wang, Chuan He, Lei Wang, Meihua Piao, Guangfan Chi, Yinan Luo, Pengfei Ge. Pseudolaric acid B triggers ferroptosis in glioma cells via activation of Nox4 and inhibition of xCT.
Cancer letters.
2018 08; 428(?):21-33. doi:
10.1016/j.canlet.2018.04.021. [PMID: 29702192] - Tan Li, Wei Wang, Yu-Xiu Li, Xiao Li, Wen-Jie Ji, Yong-Qiang Ma, Hong Chen, Ji-Hong Zhao, Xin Zhou. Pseudolaric acid B attenuates atherosclerosis progression and inflammation by suppressing PPARγ-mediated NF-κB activation.
International immunopharmacology.
2018 Jun; 59(?):76-85. doi:
10.1016/j.intimp.2018.03.041. [PMID: 29631101] - Jing Zhang, Ru-Yue Han, Huo-Chun Ye, Ying Zhou, Zheng-Ke Zhang, En-Lin Yuan, Ye Li, Chao Yan, Xia Liu, Gang Feng, Yong-Xia Guo. Effect of pseudolaric acid B on biochemical and physiologic characteristics in Colletotrichum gloeosporioides.
Pesticide biochemistry and physiology.
2018 May; 147(?):75-82. doi:
10.1016/j.pestbp.2017.09.006. [PMID: 29933996] - Guo-Dong Yao, Jing Yang, Xiu-Xiu Li, Xiao-Yu Song, Toshihiko Hayashi, Shin-Ichi Tashiro, Satoshi Onodera, Shao-Jiang Song, Takashi Ikejima. Blocking the utilization of glucose induces the switch from senescence to apoptosis in pseudolaric acid B-treated human lung cancer cells in vitro.
Acta pharmacologica Sinica.
2017 Oct; 38(10):1401-1411. doi:
10.1038/aps.2017.39. [PMID: 28649131] - Fengmei Song, Xiaoyan Yu, Haipeng Zhang, Zengyan Wang, Yue Wang, Xiangling Meng, Jinghua Yu. Pseudolaric acid B inhibits neuroglioma cell proliferation through DNA damage response.
Oncology reports.
2017 Oct; 38(4):2211-2218. doi:
10.3892/or.2017.5861. [PMID: 28765951] - Yiqing Zhou, Zhengao Di, Xiaoming Li, Yuanhong Shan, Weichao Li, Haibing Zhang, Youli Xiao. Chemical proteomics reveal CD147 as a functional target of pseudolaric acid B in human cancer cells.
Chemical communications (Cambridge, England).
2017 Aug; 53(62):8671-8674. doi:
10.1039/c7cc04345g. [PMID: 28721406] - Dan Wang, Yanqiu Tian, Wenhua Feng, Li Zhao, Mingyi Zhao, Ju Liu, Qiuyu Wang. Pseudolaric acid B induces endometrial cancer Ishikawa cell apoptosis and inhibits metastasis through AKT-GSK-3β and ERK1/2 signaling pathways.
Anti-cancer drugs.
2017 07; 28(6):603-612. doi:
10.1097/cad.0000000000000500. [PMID: 28422767] - Sibongile Mafu, Prema Sambandaswami Karunanithi, Teresa Ann Palazzo, Bronwyn Lee Harrod, Selina Marakana Rodriguez, Iris Natalie Mollhoff, Terrence Edward O'Brien, Shen Tong, Oliver Fiehn, Dean J Tantillo, Jörg Bohlmann, Philipp Zerbe. Biosynthesis of the microtubule-destabilizing diterpene pseudolaric acid B from golden larch involves an unusual diterpene synthase.
Proceedings of the National Academy of Sciences of the United States of America.
2017 01; 114(5):974-979. doi:
10.1073/pnas.1612901114. [PMID: 28096378] - Jinghua Yu, Zengyan Wang, Peiyou Ren, Ting Zhong, Yue Wang, Fengmei Song, Jingwei Hou, Xiaoyan Yu, Shucheng Hua. Pseudolaric acid B inhibits the secretion of hepatitis B virus.
Oncology reports.
2017 Jan; 37(1):519-525. doi:
10.3892/or.2016.5254. [PMID: 27878296] - Guo-Dong Yao, Jing Yang, Qiang Li, Ye Zhang, Min Qi, Si-Miao Fan, Toshihiko Hayashi, Shin-Ichi Tashiro, Satoshi Onodera, Takashi Ikejima. Activation of p53 contributes to pseudolaric acid B-induced senescence in human lung cancer cells in vitro.
Acta pharmacologica Sinica.
2016 Jul; 37(7):919-29. doi:
10.1038/aps.2016.8. [PMID: 27041461] - Liandi Chi, Delin Wu, Zhuo Li, Minmin Zhang, Hongchun Liu, Caifen Wang, Shuangying Gui, Meiyu Geng, Haiyan Li, Jiwen Zhang. Modified Release and Improved Stability of Unstable BCS II Drug by Using Cyclodextrin Complex as Carrier To Remotely Load Drug into Niosomes.
Molecular pharmaceutics.
2016 Jan; 13(1):113-24. doi:
10.1021/acs.molpharmaceut.5b00566. [PMID: 26569615] - Tao Wan, Ting Xu, Jingtong Pan, Mengyao Qin, Wenhui Pan, Guoguang Zhang, Zushuai Wu, Chuanbin Wu, Yuehong Xu. Microemulsion based gel for topical dermal delivery of pseudolaric acid B: In vitro and in vivo evaluation.
International journal of pharmaceutics.
2015 Sep; 493(1-2):111-20. doi:
10.1016/j.ijpharm.2015.07.058. [PMID: 26216411] - Helei Wang, Yan Wang, Xiaoxing Feng, Jian Suo, Nan Zhang. Development and validation of LC-MS/MS method for quantification of pseudolaric acid B from the root bark of Pseudolarix kaempferi in rat plasma: application to a pharmacokinetic study.
Journal of pharmaceutical and biomedical analysis.
2015 Apr; 108(?):56-60. doi:
10.1016/j.jpba.2015.01.050. [PMID: 25710903] - Liandi Chi, Ruihao Liu, Tao Guo, Manli Wang, Zuhua Liao, Li Wu, Haiyan Li, Deling Wu, Jiwen Zhang. Dramatic improvement of the solubility of pseudolaric acid B by cyclodextrin complexation: preparation, characterization and validation.
International journal of pharmaceutics.
2015 Feb; 479(2):349-56. doi:
10.1016/j.ijpharm.2015.01.005. [PMID: 25575474] - Fei Yu, Kai Li, Suning Chen, Yunpeng Liu, Yan Li. Pseudolaric acid B circumvents multidrug resistance phenotype in human gastric cancer SGC7901/ADR cells by downregulating Cox-2 and P-gp expression.
Cell biochemistry and biophysics.
2015 Jan; 71(1):119-26. doi:
10.1007/s12013-014-0170-7. [PMID: 25077681] - Guodong Yao, Min Qi, Xiaoling Ji, Simiao Fan, Lei Xu, Toshihiko Hayashi, Shin-ichi Tashiro, Satoshi Onodera, Takashi Ikejima. ATM-p53 pathway causes G2/M arrest, but represses apoptosis in pseudolaric acid B-treated HeLa cells.
Archives of biochemistry and biophysics.
2014 Sep; 558(?):51-60. doi:
10.1016/j.abb.2014.05.029. [PMID: 24929187] - Tingting Guan, Yanmin Yang. Role of pseudolaric acid B in A549 lung cancer cell proliferation and apoptosis.
Molecular medicine reports.
2014 Jan; 9(1):144-8. doi:
10.3892/mmr.2013.1800. [PMID: 24248012] - Na Wei, Tan Li, Hong Chen, Xin Mei, Bo Cao, Yu-Yang Zhang. The immunosuppressive activity of pseudolaric acid B on T lymphocytes in vitro.
Phytotherapy research : PTR.
2013 Jul; 27(7):980-5. doi:
10.1002/ptr.4824. [PMID: 22893196] - Jing Tong, Shutao Yin, Yinhui Dong, Xiao Guo, Lihong Fan, Min Ye, Hongbo Hu. Pseudolaric acid B induces caspase-dependent apoptosis and autophagic cell death in prostate cancer cells.
Phytotherapy research : PTR.
2013 Jun; 27(6):885-91. doi:
10.1002/ptr.4808. [PMID: 22903438] - Peng Liu, Man Xu, Hong-zhu Guo, Jiang-hao Sun, Hui Guo, Shi-feng Sun, De-an Guo. [Metabolic pathway and metabolites of pseudolaric acid B].
Yao xue xue bao = Acta pharmaceutica Sinica.
2011 Nov; 46(11):1361-5. doi:
NULL. [PMID: 22260030] - Yun Hu, Xiao-ke Wu, Li-hui Hou. [Study on the apoptosis inducing effect of pseudolaric acid B on cervical carcinoma cell line HeLa cells].
Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine.
2010 Jul; 30(7):720-2. doi:
". [PMID: 20929130] - Ting Li, Vincent Kam Wai Wong, Xiao Qin Yi, Yuen Fan Wong, Hua Zhou, Liang Liu. Pseudolaric acid B suppresses T lymphocyte activation through inhibition of NF-kappaB signaling pathway and p38 phosphorylation.
Journal of cellular biochemistry.
2009 Sep; 108(1):87-95. doi:
10.1002/jcb.22230. [PMID: 19507195] - Xiaoyuan Lei, Liang Kong, Hanfa Zou, Hong Ma, Ling Yang. Evaluation of the interaction of bioactive compounds in Cortex Pseudolarix and Radix Stephaniae by the microdialysis probe coupled with high performance liquid chromatography-mass spectrometry.
Journal of chromatography. A.
2009 Mar; 1216(11):2179-84. doi:
10.1016/j.chroma.2008.05.068. [PMID: 18573500] - Quan-Bin Han, Lina Wong, Fanny Lai, Nian-Yun Yang, Jing-Zheng Song, Chun-Feng Qiao, Hong-Xi Xu. Preparative isolation of pseudolaric acids A and B, and their glucosides from the root bark of Pseudolarix kaempferi using high-speed counter-current chromatography.
Journal of separation science.
2009 Jan; 32(2):309-13. doi:
10.1002/jssc.200800547. [PMID: 19072902] - Sheng-Ping Yang, Yu-Jun Cai, Bang-Le Zhang, Lin-Jiang Tong, Hua Xie, Yan Wu, Li-Ping Lin, Jian Ding, Jian-Min Yue. Structural modification of an angiogenesis inhibitor discovered from traditional Chinese medicine and a structure-activity relationship study.
Journal of medicinal chemistry.
2008 Jan; 51(1):77-85. doi:
10.1021/jm070906g. [PMID: 18078313] - B Liu, H Chen, Z-Y Lei, P-F Yu, B Xiong. Studies on anti-tumour activities of pseudolaric acid-B (PLAB) and its mechanism of action.
Journal of Asian natural products research.
2006 Apr; 8(3):241-52. doi:
10.1080/10286020500034360. [PMID: 16864430] - Yun-Guang Tong, Xiong-Wen Zhang, Mei-Yu Geng, Jian-Ming Yue, Xian-Liang Xin, Fang Tian, Xu Shen, Lin-Jiang Tong, Mei-Hong Li, Chao Zhang, Wei-Hong Li, Li-Ping Lin, Jian Ding. Pseudolarix acid B, a new tubulin-binding agent, inhibits angiogenesis by interacting with a novel binding site on tubulin.
Molecular pharmacology.
2006 Apr; 69(4):1226-33. doi:
10.1124/mol.105.020537. [PMID: 16424078] - Wan-Ying Wu, Hong-Zhu Guo, Gui-Qin Qu, Jian Han, De-An Guo. Mechanisms of pseudolaric acid B-induced apoptosis in Bel-7402 cell lines.
The American journal of Chinese medicine.
2006; 34(5):887-99. doi:
10.1142/s0192415x06004363. [PMID: 17080552] - Vincent K W Wong, Pauline Chiu, Stephen S M Chung, Larry M C Chow, Yun-Zhe Zhao, Burton B Yang, Ben C B Ko. Pseudolaric acid B, a novel microtubule-destabilizing agent that circumvents multidrug resistance phenotype and exhibits antitumor activity in vivo.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2005 Aug; 11(16):6002-11. doi:
10.1158/1078-0432.ccr-05-0209. [PMID: 16115945] - Mei-Hong Li, Ze-Hong Miao, Wen-Fu Tan, Jian-Min Yue, Chao Zhang, Li-Ping Lin, Xiong-Wen Zhang, Jian Ding. Pseudolaric acid B inhibits angiogenesis and reduces hypoxia-inducible factor 1alpha by promoting proteasome-mediated degradation.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2004 Dec; 10(24):8266-74. doi:
10.1158/1078-0432.ccr-04-0951. [PMID: 15623602] - Wen-Fu Tan, Xiong-Wen Zhang, Mei-Hong Li, Jian-Min Yue, Yi Chen, Li-Ping Lin, Jian Ding. Pseudolarix acid B inhibits angiogenesis by antagonizing the vascular endothelial growth factor-mediated anti-apoptotic effect.
European journal of pharmacology.
2004 Sep; 499(3):219-28. doi:
10.1016/j.ejphar.2004.07.063. [PMID: 15381043] - Maisa S Jaradat, Daniel J Noonan, Baogen Wu, Mitchell A Avery, Dennis R Feller, Maisa S Jardat. Pseudolaric acid analogs as a new class of peroxisome proliferator-activated receptor agonists.
Planta medica.
2002 Aug; 68(8):667-71. doi:
10.1055/s-2002-33785. [PMID: 12221584] - P Chiu, B Chen, K F Cheng. A rhodium carbene cyclization-cycloaddition cascade strategy toward the pseudolaric acids.
Organic letters.
2001 May; 3(11):1721-4. doi:
10.1021/ol0159165. [PMID: 11405695] - W C Wang, G D You, X J Jiang, R F Lu, Z P Gu. [Endocrine activity of pseudolaric acids A and B and their effects on sex hormones, prostaglandins, uteri, and fetuses].
Zhongguo yao li xue bao = Acta pharmacologica Sinica.
1991 Mar; 12(2):187-90. doi:
NULL. [PMID: 1776488]