Isoalantolactone (BioDeep_00000000128)

 

Secondary id: BioDeep_00000398721, BioDeep_00000868844, BioDeep_00001867466

human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds natural product


代谢物信息卡片


Naphtho(2,3-b)furan-2(3H)-one, decahydro-8a-methyl-3,5-bis(methylene)-, (3aR-(3a alpha,4a alpha,8a beta,9a alpha))-

化学式: C15H20O2 (232.14632200000003)
中文名称: 异丙内酯, 异土木香内酯, 异阿兰内酯
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 22.94%

分子结构信息

SMILES: C1CC(=C)[C@H]2[C@](C1)(C[C@@H]1[C@H](C2)C(=C)C(=O)O1)C
InChI: InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3

描述信息

Isoalantolactone is a sesquiterpene lactone of the eudesmanolide group. It has been isolated from Inula helenium. It has a role as an apoptosis inducer, an antifungal agent and a plant metabolite. It is a sesquiterpene lactone and a eudesmane sesquiterpenoid.
Isoalantolactone is a natural product found in Eupatorium cannabinum, Critonia quadrangularis, and other organisms with data available.
Isoalantolactone is found in herbs and spices. Isoalantolactone is a constituent of the essential oil of Inula helenium (elecampane)
Constituent of the essential oil of Inula helenium (elecampane). Isoalantolactone is found in herbs and spices.
Isoalantolactone is an apoptosis inducer, which also acts as an alkylating agent.
Isoalantolactone is an apoptosis inducer, which also acts as an alkylating agent.

同义名列表

40 个代谢物同义名

Naphtho(2,3-b)furan-2(3H)-one, decahydro-8a-methyl-3,5-bis(methylene)-, (3aR-(3a alpha,4a alpha,8a beta,9a alpha))-; Naphtho[2, decahydro-8a-methyl-3,5-bis(methylene)-, [3aR-(3a.alpha.,4a.alpha.,8a.beta.,9a.alpha.)]-; (3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f]benzofuran-2-one; Naphtho(2,3-b)furan-2(3H)-one, decahydro-8a-methyl-3,5-bis(methylene)-, (3aR,4aS,8aR,9aR)-rel-; Naphtho(2,3-b)furan-2(3H)-one, decahydro-8a-methyl-3,5-bis(methylene)-, (3aR,4aS,8aR,9aR)-; Rel-(3aR,4aS,8aR,9aR)-decahydro-8a-methyl-3,5-bis(methylene)naphtho(2,3-b)furan-2(3H)-one; (3aR,4aS,8aR,9aR)-8a-methyl-3,5-bis(methylidene)decahydronaphtho[2,3-b]furan-2(3H)-one; (3AR,4AS,8AR,9AR)-DECAHYDRO-8A-METHYL-3,5-BIS(METHYLENE)NAPHTHO(2,3-B)FURAN-2(3H)-ONE; (3aR,4aS,8aR,9aR)-Decahydro-8a-methyl-3,5-bis(methylene)naphtho[2,3-b]furan-2(3H)-one; (3AR,4AS,8AR,9AR)-8A-METHYL-3,5-DIMETHYLIDENE-DODECAHYDRONAPHTHO[2,3-B]FURAN-2-ONE; (3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylenedecahydronaphtho[2,3-b]furan-2(3H)-one; EUDESMA-4(14),11(13)-DIEN-12-OIC ACID, 8.BETA.-HYDROXY-, .GAMMA.-LACTONE, (+/-)-; (3aR,4aS,8aR,9aR)-8a-Methyl-3,5-dimethylene-decahydro-naphtho[2,3-b]furan-2-one; Eudesma-4(14),11(13)-dien-12-oic acid, 8beta-hydroxy-, gamma-lactone, (+/-)-; EUDESMA-4(14),11(13)-DIEN-12-OIC ACID, 8.BETA.-HYDROXY-, .GAMMA.-LACTONE; Eudesma-4(14),11(13)-dien-12-oic acid, 8-beta-hydroxy-, gamma-lactone; 8a-methyl-3,5-dimethylidene-dodecahydronaphtho[2,3-b]furan-2-one; 8beta-hydroxyeudesma-4(14),11(13)-dien-12-oic acid gamma-lactone; 8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one; 5.ALPHA.H-EUDESMA-4(15),11(13)-DIEN-12,8.BETA.-OLIDE; 4-17-00-05031 (Beilstein Handbook Reference); eudesma-4(14),11(13)-dieno-12,8beta-olactone; (+)-Isoalantolactone;Isohelenin; Isoalantolactone (Isohelenin); Isoalantolactone, (+/-)-; ISOALANTOLACTONE, (+)-; (+/-)-Isoalantolactone; (+)-Isoalantolactone; ISOALLANTOLACTONE; iso-alantolacton; Isoalantolactone; ISOALANTOACTONE; UNII-BYH07P620U; UNII-QTF89ZHT7V; BYH07P620U; QTF89ZHT7V; Isohelenin; AI3-31148; Isoalantolactone; Isoalantolactone



数据库引用编号

28 个数据库交叉引用编号

分类词条

相关代谢途径

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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)

134 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

  • Min Zhao, Neng Ye, Ling Liu, Rui-Jia Zhang, Na Li, Jing Peng, Xiao-Ying Cai, Xue-Qin Jiang, Kai-Yue Su, Xin-Lu Zhang, Qian-Ru Rao, Kong-Jun Liu, De-Xin Deng, Ai-Hua Peng, Ming-Hai Tang, Li-Juan Chen, Wen-Shuang Wu, Hao-Yu Ye. Novel Isoalantolactone-Based Derivatives as Potent NLRP3 Inflammasome Inhibitors: Design, Synthesis, and Biological Characterization. Journal of medicinal chemistry. 2024 May; 67(9):7516-7538. doi: 10.1021/acs.jmedchem.4c00357. [PMID: 38686671]
  • Siming Wang, Qihan Cai, Lu Xu, Yanan Sun, Mengmeng Wang, Yu Wang, Lili Zhang, Keqing Li, Zhiyu Ni. Isoalantolactone relieves depression-like behaviors in mice after chronic social defeat stress via the gut-brain axis. Psychopharmacology. 2023 Aug; 240(8):1775-1787. doi: 10.1007/s00213-023-06413-8. [PMID: 37400661]
  • Lu Xu, Yanan Sun, Qihan Cai, Mengmeng Wang, Xinliang Wang, Siming Wang, Zhiyu Ni. Research progress on pharmacological effects of isoalantolactone. The Journal of pharmacy and pharmacology. 2023 Mar; ?(?):. doi: 10.1093/jpp/rgac103. [PMID: 36940405]
  • Syed Mudassir Jeelani, Mohd Shahnawaz, Ajai Prakash Gupta, Surrinder K Lattoo. Phytochemical Diversity in Relation to Cytogenetic Variability in Inula racemosa Hook.f., an Endangered Medicinal Plant of Himalayas. Chemistry & biodiversity. 2022 Dec; 19(12):e202200486. doi: 10.1002/cbdv.202200486. [PMID: 36263992]
  • Y Y Yan, Q Zhang, B Zhang, B Yang, N M Lin. Active ingredients of Inula helenium L. exhibits similar anti-cancer effects as isoalantolactone in pancreatic cancer cells. Natural product research. 2020 Sep; 34(17):2539-2544. doi: 10.1080/14786419.2018.1543676. [PMID: 30661396]
  • Akram Taleghani, Seyed Ahmad Emami, Zahra Tayarani-Najaran. Artemisia: a promising plant for the treatment of cancer. Bioorganic & medicinal chemistry. 2020 01; 28(1):115180. doi: 10.1016/j.bmc.2019.115180. [PMID: 31784199]
  • Renjie Xu, Ying Peng, Mengyue Wang, Xiaobo Li. Intestinal Absorption of Isoalantolactone and Alantolactone, Two Sesquiterpene Lactones from Radix Inulae, Using Caco-2 Cells. European journal of drug metabolism and pharmacokinetics. 2019 Apr; 44(2):295-303. doi: 10.1007/s13318-018-0510-x. [PMID: 30209793]
  • Zhengyang Lu, Guangxin Zhang, Yifan Zhang, Peiyan Hua, Meidan Fang, Meiliang Wu, Tongjun Liu. Isoalantolactone induces apoptosis through reactive oxygen species-dependent upregulation of death receptor 5 in human esophageal cancer cells. Toxicology and applied pharmacology. 2018 08; 352(?):46-58. doi: 10.1016/j.taap.2018.05.026. [PMID: 29800641]
  • Deepti Arha, E Ramakrishna, Anand P Gupta, Amit K Rai, Aditya Sharma, Ishbal Ahmad, Mohammed Riyazuddin, Jiaur R Gayen, Rakesh Maurya, Akhilesh K Tamrakar. Isoalantolactone derivative promotes glucose utilization in skeletal muscle cells and increases energy expenditure in db/db mice via activating AMPK-dependent signaling. Molecular and cellular endocrinology. 2018 01; 460(?):134-151. doi: 10.1016/j.mce.2017.07.015. [PMID: 28736255]
  • Bailun Zhou, Ji Ye, Niao Yang, Liping Chen, Zhiguo Zhuo, Ling Mao, Qun Liu, Gongcai Lan, Jing Ning, Guangbo Ge, Ling Yang, Yunheng Shen, Shumei Wang, Weidong Zhang. Metabolism and pharmacokinetics of alantolactone and isoalantolactone in rats: Thiol conjugation as a potential metabolic pathway. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 Jan; 1072(?):370-378. doi: 10.1016/j.jchromb.2017.11.039. [PMID: 29223921]
  • Yang Yang, Rui Tu, Wenji Sun, Zhongliang Zhu, Yongmin Zhang. Silver perchlorate in the mobile phase for rapid separation and determination of a pair of positional isomers in Inula racemosa Hook.f. with RP-HPLC. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Sep; 1063(?):25-30. doi: 10.1016/j.jchromb.2017.08.013. [PMID: 28837869]
  • Guodong He, Xu Zhang, Yanhua Chen, Jing Chen, Li Li, Yubo Xie. Isoalantolactone inhibits LPS-induced inflammation via NF-κB inactivation in peritoneal macrophages and improves survival in sepsis. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2017 Jun; 90(?):598-607. doi: 10.1016/j.biopha.2017.03.095. [PMID: 28407580]
  • Jing Wang, Li Cui, Liang Feng, Zhenhai Zhang, Jie Song, Dan Liu, Xiaobin Jia. Isoalantolactone inhibits the migration and invasion of human breast cancer MDA-MB-231 cells via suppression of the p38 MAPK/NF-κB signaling pathway. Oncology reports. 2016 Sep; 36(3):1269-76. doi: 10.3892/or.2016.4954. [PMID: 27461575]
  • Min Wu, Tingting Li, Lilan Chen, Sugang Peng, Wei Liao, Ruolan Bai, Xue Zhao, Hong Yang, Chunhui Wu, Hongjuan Zeng, Yiyao Liu. Essential oils from Inula japonica and Angelicae dahuricae enhance sensitivity of MCF-7/ADR breast cancer cells to doxorubicin via multiple mechanisms. Journal of ethnopharmacology. 2016 Mar; 180(?):18-27. doi: 10.1016/j.jep.2016.01.015. [PMID: 26795076]
  • Renjie Xu, Guisheng Zhou, Ying Peng, Mengyue Wang, Xiaobo Li. Pharmacokinetics, tissue distribution and excretion of isoalantolactone and alantolactone in rats after oral administration of Radix Inulae extract. Molecules (Basel, Switzerland). 2015 Apr; 20(5):7719-36. doi: 10.3390/molecules20057719. [PMID: 25927901]
  • Ruoqi Zhang, Cheng Peng, Yunxia Li, Liang Xiong, Xiaohong Gong. A gas chromatography-mass spectrometry method for the determination of pogostone in canine plasma and its application to a pharmacokinetic study. Journal of chromatographic science. 2014 Nov; 52(10):1151-6. doi: 10.1093/chromsci/bmt201. [PMID: 24714140]
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  • Chunjie Guo, Sixi Zhang, Shiyong Teng, Kai Niu. Simultaneous determination of sesquiterpene lactones isoalantolactone and alantolactone isomers in rat plasma by liquid chromatography with tandem mass spectrometry: application to a pharmacokinetic study. Journal of separation science. 2014 Apr; 37(8):950-6. doi: 10.1002/jssc.201400119. [PMID: 24520052]
  • Azhar Rasul, Jun Di, Faya Martin Millimouno, Mahadev Malhi, Ichiro Tsuji, Muhammad Ali, Jiang Li, Xiaomeng Li. Reactive oxygen species mediate isoalantolactone-induced apoptosis in human prostate cancer cells. Molecules (Basel, Switzerland). 2013 Aug; 18(8):9382-96. doi: 10.3390/molecules18089382. [PMID: 23921797]
  • Yan-Yan Ma, Deng-Gao Zhao, Kun Gao. Structural investigation and biological activity of sesquiterpene lactones from the traditional Chinese herb Inula racemosa. Journal of natural products. 2013 Apr; 76(4):564-70. doi: 10.1021/np300742d. [PMID: 23451797]
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  • Anna Wajs-Bonikowska, Anna Stojakowska, Danuta Kalemba. Chemical composition of essential oils from a multiple shoot culture of Telekia speciosa and different plant organs. Natural product communications. 2012 May; 7(5):625-8. doi: ". [PMID: 22799093]
  • Jin Wang, Yong-Ming Zhao, Chun-Yan Guo, Shao-Meng Zhang, Chun-Lei Liu, Dan-Shen Zhang, Xue-Mei Bai. Ultrasound-assisted extraction of total flavonoids from Inula helenium. Pharmacognosy magazine. 2012 Apr; 8(30):166-70. doi: 10.4103/0973-1296.96581. [PMID: 22701292]
  • Li Liu, Hongyue Ma, Yuping Tang, Wenxing Chen, Yin Lu, Jianming Guo, Jin-Ao Duan. Discovery of estrogen receptor α modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells. Bioorganic & medicinal chemistry letters. 2012 Jan; 22(1):154-63. doi: 10.1016/j.bmcl.2011.11.041. [PMID: 22137340]
  • Muhammad Khan, Chuan Ding, Azhar Rasul, Fei Yi, Ting Li, Hongwen Gao, Rong Gao, Lili Zhong, Kun Zhang, Xuedong Fang, Tonghui Ma. Isoalantolactone induces reactive oxygen species mediated apoptosis in pancreatic carcinoma PANC-1 cells. International journal of biological sciences. 2012; 8(4):533-47. doi: 10.7150/ijbs.3753. [PMID: 22532787]
  • Jiazhang Qiu, Mingjing Luo, Jianfeng Wang, Jing Dong, Hongen Li, Bingfeng Leng, Qian Zhang, Xiaohan Dai, Yu Zhang, Xiaodi Niu, Xuming Deng. Isoalantolactone protects against Staphylococcus aureus pneumonia. FEMS microbiology letters. 2011 Nov; 324(2):147-55. doi: 10.1111/j.1574-6968.2011.02397.x. [PMID: 22092816]
  • Hidehisa Shimizu, Dilinaer Bolati, Ayinuer Adijiang, Yelixiati Adelibieke, Gulinuer Muteliefu, Atsushi Enomoto, Yukihiro Higashiyama, Yusuke Higuchi, Fuyuhiko Nishijima, Toshimitsu Niwa. Indoxyl sulfate downregulates renal expression of Klotho through production of ROS and activation of nuclear factor-ĸB. American journal of nephrology. 2011; 33(4):319-24. doi: 10.1159/000324885. [PMID: 21389697]
  • Harish Chandra Pal, Irum Sehar, Shashi Bhushan, Bishan Dutt Gupta, Ajit Kumar Saxena. Activation of caspases and poly (ADP-ribose) polymerase cleavage to induce apoptosis in leukemia HL-60 cells by Inula racemosa. Toxicology in vitro : an international journal published in association with BIBRA. 2010 Sep; 24(6):1599-609. doi: 10.1016/j.tiv.2010.06.007. [PMID: 20600805]
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  • Ji Yeon Seo, Jia Park, Hyo Jung Kim, In Ae Lee, Ji-Sun Lim, Soon Sung Lim, Se-Jin Choi, Jung Han Yoon Park, Hui Jung Kang, Jong-Sang Kim. Isoalantolactone from Inula helenium caused Nrf2-mediated induction of detoxifying enzymes. Journal of medicinal food. 2009 Oct; 12(5):1038-45. doi: 10.1089/jmf.2009.0072. [PMID: 19857067]
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