Alantolactone (BioDeep_00000000468)

 

Secondary id: BioDeep_00001867506

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


Naphtho(2,3-b)furan-2(3H)-one, 3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylene-, (3aR-(3a alpha,5beta,8a beta,9a alpha))-

化学式: C15H20O2 (232.14632200000003)
中文名称: 木香油內酯, 土木香内酯, 土木香脑, 阿兰内酯, 木香腦, 土木香内酯
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 6.45%

分子结构信息

SMILES: C=C1C(=O)OC2CC3(C)CCCC(C)C3=CC12
InChI: InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h7,9,11,13H,2,4-6,8H2,1,3H3

描述信息

Alantolactone is a sesquiterpene lactone that is 3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2-one bearing two methyl substituents at positions 5 and 8a as well as a methylidene substituent at position 3. It has a role as a plant metabolite, an apoptosis inducer and an antineoplastic agent. It is a sesquiterpene lactone, a naphthofuran and an olefinic compound.
Alantolactone is a natural product found in Eupatorium cannabinum, Pentanema britannicum, and other organisms with data available.
Alantolactone is found in herbs and spices. Alantolactone is a constituent of Inula helenium (elecampane)
Constituent of Inula helenium (elecampane). Alantolactone is found in herbs and spices.
Alantolactone is a selective STAT3 inhibitor, with potent anticancer activity. Alantolactone induces apoptosis in cancer[1][2][3].
Alantolactone is a selective STAT3 inhibitor, with potent anticancer activity. Alantolactone induces apoptosis in cancer[1][2][3].

同义名列表

41 个代谢物同义名

Naphtho(2,3-b)furan-2(3H)-one, 3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylene-, (3aR-(3a alpha,5beta,8a beta,9a alpha))-; [3aR-(3a alpha,5 beta,8a beta,9a alpha)]-3a,5,6,7,8,8a,9,9a-Octahydro-5,8a-dimethyl-3-methylenenaphtho[2,3-b]furan-2(3H)-one; (3AR-(3aalpha,5beta,8abeta,9aalpha))-3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylenenaphtho(2,3-b)furan-2(3H)-one; Naphtho[2, 3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylene-, [3aR-(3a.alpha.,5.beta.,8a.beta.,9a.alpha.)]-; Naphtho[2,3-b]furan-2(3H)-one, 3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylene-, (3aR,5S,8aR,9aR)-; Naphtho[2,3-b]furan-2(3H)-one,3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylene-,(3aR,5S,8aR,9aR)-; (3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylidene-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one; (3aR,5S,8aR,9aR)-3a,5,6,7,8,8a,9,9a-Octahydro-5,8a-dimethyl-3-methylenenaphtho[2,3-b]furan-2(3H)-one; (3aR,5S,8aR,9aR)-5,8a-Dimethyl-3-methylene-3,3a,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(5H)-one; (3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylene-5,6,7,8,9,9a-hexahydro-3aH-benzo[f]benzofuran-2-one; 5,8a-dimethyl-3-methylidene-2H,3H,3aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one; 4alphaH-Eudesma-5,11(13)-dien-12-oic acid, 8beta-hydroxy-, gamma-lactone; 8.BETA.-HYDROXY-4.ALPHA.H-EUDESM-5-EN-12-OIC ACID .GAMMA.-LACTONE; 4.alpha.H-Eudesma-5, 8.beta.-hydroxy-, .gamma.-lactone; (+)-Alantolactone; Alant camphor; Inula camphor; Alantolactone, >=98\\% (HPLC); ALANTOLACTONE [MI]; Elecampane camphor; (+)-Alantolactone; Alantic anhydride; Spectrum4_001772; Spectrum5_000383; Spectrum3_001358; Spectrum2_000297; UNII-M7GSN5Q1M6; BOHLMANN K2631; Inula camphor; Alant camphor; Alantolactone; KBio3_002395; KBio2_003345; KBio2_005913; KBio2_000777; NCI60_042073; Alantcamphor; M7GSN5Q1M6; Helenine?; AI3-31147; helenine; helenin; Eupatal



数据库引用编号

25 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)

54 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

  • Zhi-E Fang, Yan Wang, Shuyi Bian, Shuanglin Qin, Huanying Zhao, Jincai Wen, Tingting Liu, Lutong Ren, Qiang Li, Wei Shi, Jia Zhao, Huijie Yang, Rui Peng, Qin Wang, Zhaofang Bai, Guang Xu. Helenine blocks NLRP3 activation by disrupting the NEK7-NLRP3 interaction and ameliorates inflammatory diseases. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2024 Jan; 122(?):155159. doi: 10.1016/j.phymed.2023.155159. [PMID: 37931457]
  • Yueyue Sun, Mengnan Yang, Shujun Li, Ying Hu, Biao Yang, Xu Li, Rong Yan, Kesheng Dai. Alantolactone induces platelet apoptosis by activating the Akt pathway. Platelets. 2023 Feb; ?(?):2173505. doi: 10.1080/09537104.2023.2173505. [PMID: 36813739]
  • Weifeng Li, Haowen Xu, Jingjing Shao, Jiahao Chen, Yimin Lin, Zhiwei Zheng, Yi Wang, Wu Luo, Guang Liang. Discovery of alantolactone as a naturally occurring NLRP3 inhibitor to alleviate NLRP3-driven inflammatory diseases in mice. British journal of pharmacology. 2023 Jan; ?(?):. doi: 10.1111/bph.16036. [PMID: 36668704]
  • Yiqun Hu, Qingliang Wen, Yefeng Cai, Yunye Liu, Wenli Ma, Qinglin Li, Fahuan Song, Yawen Guo, Lei Zhu, Jingyan Ge, Qian Zeng, Jiahui Wang, Changtian Yin, Guowan Zheng, Minghua Ge. Alantolactone induces concurrent apoptosis and GSDME-dependent pyroptosis of anaplastic thyroid cancer through ROS mitochondria-dependent caspase pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Jan; 108(?):154528. doi: 10.1016/j.phymed.2022.154528. [PMID: 36343549]
  • 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]
  • Romit Seth, Amna Devi, Balraj Sharma, Mamta Masand, Gopal Singh, Poonam Pal, Ashlesha Holkar, Shikha Sharma, Vishal Sharma, Shivanti Negi, Ram Kumar Sharma. An Integrative Transcriptional Network Revealed Spatial Molecular Interplay Underlying Alantolactone and Inulin Biosynthesis in Inula racemosa Hook f. International journal of molecular sciences. 2022 Sep; 23(19):. doi: 10.3390/ijms231911213. [PMID: 36232516]
  • Yeon-Seop Jung, Yun-Jeong Jeong, Joung-Hee Kim, Chang-Hwan Jeon, Syng-Ook Lee. Elecampane (Inula helenium) Root Extract and Its Major Sesquiterpene Lactone, Alantolactone, Inhibit Adipogenesis of 3T3-L1 Preadipocytes. Molecules (Basel, Switzerland). 2022 Jul; 27(15):. doi: 10.3390/molecules27154765. [PMID: 35897937]
  • Zhijian Luo, Yantao Luo, Xiaoling Liang, Qingyang Lyu, Fanliang Meng, Xuncai Chen, Yupeng Wang, Weiyi Fang, Aimin Li, Dongfang Zhou. Alantolactone-Loaded Pegylated Prodrug Nanocarriers for Synergistic Treatment of Cisplatin-Resistant Ovarian Cancer via Reactivating Mitochondrial Apoptotic Pathway. ACS biomaterials science & engineering. 2022 06; 8(6):2526-2536. doi: 10.1021/acsbiomaterials.2c00316. [PMID: 35612599]
  • Qiang Shen, Ji-Xia Kuang, Chun-Xiao Miao, Wan-Li Zhang, Yi-Wei Li, Xiong-Wen Zhang, Xuan Liu. Alantolactone ameliorates cancer cachexia-associated muscle atrophy mainly by inhibiting the STAT3 signaling pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Jan; 95(?):153858. doi: 10.1016/j.phymed.2021.153858. [PMID: 34861585]
  • Miaomiao Liu, Panpan Liu, Bin Zheng, Yu Liu, Li Li, Xue Han, Yangshuang Liu, Li Chu. Cardioprotective effects of alantolactone on isoproterenol-induced cardiac injury and cobalt chloride-induced cardiomyocyte injury. International journal of immunopathology and pharmacology. 2022 Jan; 36(?):20587384211051993. doi: 10.1177/20587384211051993. [PMID: 34986670]
  • Feng Zhou, Zhenzhi Wang, Kang Xiong, Meiling Zhang, Yuan Wang, Maode Wang. Alantolactone reduced neuron injury via activating PI3K/Akt signaling pathway after subarachnoid hemorrhage in rats. PloS one. 2022; 17(6):e0270410. doi: 10.1371/journal.pone.0270410. [PMID: 35749405]
  • Xin Liu, Lijuan Bian, Xiaoqin Duan, Xinming Zhuang, Yujie Sui, Longfei Yang. Alantolactone: A sesquiterpene lactone with diverse pharmacological effects. Chemical biology & drug design. 2021 12; 98(6):1131-1145. doi: 10.1111/cbdd.13972. [PMID: 34624172]
  • Yijing Ren, Cheng Lv, Jing Zhang, Beibei Zhang, Bei Yue, Xiaoping Luo, Zhilun Yu, Hao Wang, Junyu Ren, Zhengtao Wang, Wei Dou. Alantolactone exhibits antiproliferative and apoptosis-promoting properties in colon cancer model via activation of the MAPK-JNK/c-Jun signaling pathway. Molecular and cellular biochemistry. 2021 Dec; 476(12):4387-4403. doi: 10.1007/s11010-021-04247-6. [PMID: 34460036]
  • Xiaodong Sun, Hongxia Xu, Tianyu Dai, Lixia Xie, Qiang Zhao, Xincai Hao, Yan Sun, Xuanbin Wang, Nan Jiang, Ming Sang. Alantolactone inhibits cervical cancer progression by downregulating BMI1. Scientific reports. 2021 04; 11(1):9251. doi: 10.1038/s41598-021-87781-z. [PMID: 33927214]
  • 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]
  • Tomáš Zárybnický, Petra Matoušková, Lenka Skálová, Iva Boušová. The Hepatotoxicity of Alantolactone and Germacrone: Their Influence on Cholesterol and Lipid Metabolism in Differentiated HepaRG Cells. Nutrients. 2020 Jun; 12(6):. doi: 10.3390/nu12061720. [PMID: 32521813]
  • Yu Zhu, Yuanliang Ling, Xiao'ai Wang. Alantolactone mitigates renal injury induced by diabetes via inhibition of high glucose-mediated inflammatory response and macrophage infiltration. Immunopharmacology and immunotoxicology. 2020 Apr; 42(2):84-92. doi: 10.1080/08923973.2020.1725039. [PMID: 32064988]
  • Barbara Gierlikowska, Wojciech Gierlikowski, Katarzyna Bekier, Krystyna Skalicka-Woźniak, Monika E Czerwińska, Anna K Kiss. Inula helenium and Grindelia squarrosa as a source of compounds with anti-inflammatory activity in human neutrophils and cultured human respiratory epithelium. Journal of ethnopharmacology. 2020 Mar; 249(?):112311. doi: 10.1016/j.jep.2019.112311. [PMID: 31644941]
  • Xing Kang, Hijuan Wang, Yanwei Li, Ying Xiao, Lili Zhao, Tingting Zhang, Shaohe Zhou, Xiaolun Zhou, Yi Li, Zhexing Shou, Chao Chen, Bin Li. Alantolactone induces apoptosis through ROS-mediated AKT pathway and inhibition of PINK1-mediated mitophagy in human HepG2 cells. Artificial cells, nanomedicine, and biotechnology. 2019 Dec; 47(1):1961-1970. doi: 10.1080/21691401.2019.1593854. [PMID: 31116036]
  • Jing Zhang, Limei Shen, Xiang Li, Wantong Song, Yun Liu, Leaf Huang. Nanoformulated Codelivery of Quercetin and Alantolactone Promotes an Antitumor Response through Synergistic Immunogenic Cell Death for Microsatellite-Stable Colorectal Cancer. ACS nano. 2019 11; 13(11):12511-12524. doi: 10.1021/acsnano.9b02875. [PMID: 31664821]
  • Yijing Ren, Bei Yue, Gaiyan Ren, Zhilun Yu, Xiaoping Luo, Aning Sun, Jingjing Zhang, Mengqing Han, Zhengtao Wang, Wei Dou. Activation of PXR by alantolactone ameliorates DSS-induced experimental colitis via suppressing NF-κB signaling pathway. Scientific reports. 2019 11; 9(1):16636. doi: 10.1038/s41598-019-53305-z. [PMID: 31719637]
  • Yibing Zhang, Yong Zhao, Yongwang Ran, Jianyou Guo, Haifeng Cui, Sha Liu. Alantolactone exhibits selective antitumor effects in HELA human cervical cancer cells by inhibiting cell migration and invasion, G2/M cell cycle arrest, mitochondrial mediated apoptosis and targeting Nf-kB signalling pathway. Journal of B.U.ON. : official journal of the Balkan Union of Oncology. 2019 Nov; 24(6):2310-2315. doi: . [PMID: 31983099]
  • 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]
  • Meiting Yang, Hanhan Zhao, Huihan Ai, Hongbin Zhu, Shuyue Wang, Yongli Bao, Yuxin Li. Alantolactone suppresses APOC3 expression and alters lipid homeostasis in L02 liver cells. European journal of pharmacology. 2018 Jun; 828(?):60-66. doi: 10.1016/j.ejphar.2018.03.021. [PMID: 29555504]
  • Bo-Kyung Lee, Soo-Jin Park, So-Yeon Nam, Saeromi Kang, Jin Hwang, Seung-Jin Lee, Dong-Soon Im. Anti-allergic effects of sesquiterpene lactones from Saussurea costus (Falc.) Lipsch. determined using in vivo and in vitro experiments. Journal of ethnopharmacology. 2018 Mar; 213(?):256-261. doi: 10.1016/j.jep.2017.11.018. [PMID: 29158156]
  • Li Cui, Weiquan Bu, Jie Song, Liang Feng, Tingting Xu, Dan Liu, Wenbo Ding, Jianhua Wang, Changyang Li, Binge Ma, Yi Luo, Ziyu Jiang, Chengcheng Wang, Juan Chen, Jian Hou, Hongmei Yan, Lei Yang, Xiaobin Jia. Apoptosis induction by alantolactone in breast cancer MDA-MB-231 cells through reactive oxygen species-mediated mitochondrion-dependent pathway. Archives of pharmacal research. 2018 Mar; 41(3):299-313. doi: 10.1007/s12272-017-0990-2. [PMID: 29214600]
  • 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]
  • Lin Chen, Jian-Ping Zhang, Xin Liu, Jiang-Jiang Tang, Ping Xiang, Xing-Ming Ma. Semisynthesis, an Anti-Inflammatory Effect of Derivatives of 1β-Hydroxy Alantolactone from Inula britannica. Molecules (Basel, Switzerland). 2017 Oct; 22(11):. doi: 10.3390/molecules22111835. [PMID: 29077042]
  • 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]
  • Minjee Kim, Kwangho Song, Yeong Shik Kim. Alantolactone improves palmitate-induced glucose intolerance and inflammation in both lean and obese states in vitro: Adipocyte and adipocyte-macrophage co-culture system. International immunopharmacology. 2017 Aug; 49(?):187-194. doi: 10.1016/j.intimp.2017.05.037. [PMID: 28599253]
  • Donggui Yao, Zhe Li, Changhong Huo, Yufang Wang, Yibing Wu, Manli Zhang, Ligeng Li, Qingwen Shi, Hiromasa Kiyota, Xiaowei Shi. Identification of in vitro and in vivo metabolites of alantolactone by UPLC-TOF-MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2016 Oct; 1033-1034(?):250-260. doi: 10.1016/j.jchromb.2016.08.034. [PMID: 27571685]
  • Jae-Young Lee, Sang-Bum Kim, Jaemoo Chun, Kwang Ho Song, Yeong Shik Kim, Suk-Jae Chung, Hyun-Jong Cho, In-Soo Yoon, Dae-Duk Kim. High body clearance and low oral bioavailability of alantolactone, isolated from Inula helenium, in rats: extensive hepatic metabolism and low stability in gastrointestinal fluids. Biopharmaceutics & drug disposition. 2016 Apr; 37(3):156-67. doi: 10.1002/bdd.2005. [PMID: 26861967]
  • Caidan Rezeng, Dongping Yuan, Jun Long, Dengdeng Suonan, Fang Yang, Wenyuan Li, Li Tong, Pengcuo Jiumei. Alantolactone exhibited anti-herpes simplex virus 1 (HSV-1) action in vitro. Bioscience trends. 2015 Dec; 9(6):420-2. doi: 10.5582/bst.2015.01171. [PMID: 26781801]
  • Hye-Sun Lim, Sung-Eun Jin, Ohn-Soon Kim, Hyeun-Kyoo Shin, Soo-Jin Jeong. Alantolactone from Saussurea lappa Exerts Antiinflammatory Effects by Inhibiting Chemokine Production and STAT1 Phosphorylation in TNF-α and IFN-γ-induced in HaCaT cells. Phytotherapy research : PTR. 2015 Jul; 29(7):1088-96. doi: 10.1002/ptr.5354. [PMID: 25881570]
  • Chong-Zhen Qin, Qiao-Li Lv, Na-Yiyuan Wu, Lin Cheng, Yun-Chen Chu, Tang-Yuan Chu, Lei Hu, Yu Cheng, Xue Zhang, Hong-Hao Zhou. Mechanism-based inhibition of Alantolactone on human cytochrome P450 3A4 in vitro and activity of hepatic cytochrome P450 in mice. Journal of ethnopharmacology. 2015 Jun; 168(?):146-9. doi: 10.1016/j.jep.2015.03.061. [PMID: 25858508]
  • 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]
  • Jin Wang, Yong-ming Zhao, Man-li Zhang, Qing-wen Shi. Simultaneous determination of chlorogenic acid, caffeic acid, alantolactone and isoalantolactone in Inula helenium by HPLC. Journal of chromatographic science. 2015 Apr; 53(4):526-30. doi: 10.1093/chromsci/bmu079. [PMID: 24996657]
  • 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]
  • Chunhui Yang, Jingbo Yang, Meiyan Sun, Jiangzhou Yan, Xiuxiang Meng, Tonghui Ma. Alantolactone inhibits growth of K562/adriamycin cells by downregulating Bcr/Abl and P-glycoprotein expression. IUBMB life. 2013 May; 65(5):435-44. doi: 10.1002/iub.1141. [PMID: 23441067]
  • 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]
  • Muhammad Khan, Fei Yi, Azhar Rasul, Ting Li, Nan Wang, Hongwen Gao, Rong Gao, Tonghui Ma. Alantolactone induces apoptosis in glioblastoma cells via GSH depletion, ROS generation, and mitochondrial dysfunction. IUBMB life. 2012 Sep; 64(9):783-94. doi: 10.1002/iub.1068. [PMID: 22837216]
  • Z Stojanović-Radić, Lj Comić, N Radulović, P Blagojević, M Denić, A Miltojević, J Rajković, T Mihajilov-Krstev. Antistaphylococcal activity of Inula helenium L. root essential oil: eudesmane sesquiterpene lactones induce cell membrane damage. European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology. 2012 Jun; 31(6):1015-25. doi: 10.1007/s10096-011-1400-1. [PMID: 21901633]
  • 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]
  • 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]
  • 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]
  • Xiangrong Cheng, Qi Zeng, Jie Ren, Jiangjiang Qin, Shoude Zhang, Yunheng Shen, Jiaxian Zhu, Fei Zhang, Ruijie Chang, Yan Zhu, Weidong Zhang, Huizi Jin. Sesquiterpene lactones from Inula falconeri, a plant endemic to the Himalayas, as potential anti-inflammatory agents. European journal of medicinal chemistry. 2011 Nov; 46(11):5408-15. doi: 10.1016/j.ejmech.2011.08.047. [PMID: 21924800]
  • Caroline van Haaften, Colin C Duke, Arij M Weerheim, Nico Pm Smit, Paul Mm van Haard, Firouz Darroudi, Baptist Jmz Trimbos. Potent cytotoxic effects of Calomeria amaranthoides on ovarian cancers. Journal of experimental & clinical cancer research : CR. 2011 Mar; 30(?):29. doi: 10.1186/1756-9966-30-29. [PMID: 21401934]
  • Evy Paulsen, Klaus E Andersen. Screening for Compositae sensitization with pure allergens: implications of molecular structure, strength of reaction, and time of testing. Contact dermatitis. 2011 Feb; 64(2):96-103. doi: 10.1111/j.1600-0536.2010.01822.x. [PMID: 21138444]
  • 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]
  • Antoaneta Trendafilova, Christo Chanev, Milka Todorova. Ultrasound-assisted extraction of alantolactone and isoalantolactone from Inula helenium roots. Pharmacognosy magazine. 2010 Jul; 6(23):234-7. doi: 10.4103/0973-1296.66942. [PMID: 20931085]
  • Ji Yeon Seo, Soon Sung Lim, Jia Park, Ji-Sun Lim, Hyo Jung Kim, Hui Jung Kang, Jung Han Yoon Park, Jong-Sang Kim. Protection by Chrysanthemum zawadskii extract from liver damage of mice caused by carbon tetrachloride is maybe mediated by modulation of QR activity. Nutrition research and practice. 2010 Apr; 4(2):93-8. doi: 10.4162/nrp.2010.4.2.93. [PMID: 20461196]
  • Nirmal K Bairwa, Neeraj K Sethiya, S H Mishra. Protective effect of stem bark of Ceiba pentandra linn. against paracetamol-induced hepatotoxicity in rats. Pharmacognosy research. 2010 Jan; 2(1):26-30. doi: 10.4103/0974-8490.60584. [PMID: 21808535]
  • 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]
  • Ji Yeon Seo, Soon Sung Lim, Ju Ryoung Kim, Ji-Sun Lim, Young Ran Ha, In Ae Lee, Eun Ji Kim, Jung Han Yoon Park, Jong-Sang Kim. Nrf2-mediated induction of detoxifying enzymes by alantolactone present in Inula helenium. Phytotherapy research : PTR. 2008 Nov; 22(11):1500-5. doi: 10.1002/ptr.2521. [PMID: 18702092]
  • Soon Sung Lim, Sun Seong Im, Ju Ryoung Kim, Hyun Ae Lim, Chan Ho Jang, Young Kyoon Kim, T Konishi, Eun Ji Kim, Jung Han Yoon Park, Jong-Sang Kim. Induction of detoxifying enzyme by sesquiterpenes present in Inula helenium. Journal of medicinal food. 2007 Sep; 10(3):503-10. doi: 10.1089/jmf.2006.209. [PMID: 17887945]
  • Anna Stojakowska, Klaudia Michalska, Janusz Malarz. Simultaneous quantification of eudesmanolides and thymol derivatives from tissues of Inula helenium and I. royleana by reversed-phase high-performance liquid chromatography. Phytochemical analysis : PCA. 2006 May; 17(3):157-61. doi: 10.1002/pca.900. [PMID: 16749422]
  • M Jovanović, N Mimica-Dukić, M Poljacki, P Boza. Erythema multiforme due to contact with weeds: a recurrence after patch testing. Contact dermatitis. 2003 Jan; 48(1):17-25. doi: 10.1034/j.1600-0536.2003.480104.x. [PMID: 12641574]
  • J C Meng, Y F Hu, J H Chen, R X Tan. Antifungal highly oxygenated guaianolides and other constituents from Ajania fruticulosa. Phytochemistry. 2001 Dec; 58(7):1141-5. doi: 10.1016/s0031-9422(01)00389-2. [PMID: 11730880]
  • C L Cantrell, S G Franzblau, N H Fischer. Antimycobacterial plant terpenoids. Planta medica. 2001 Nov; 67(8):685-94. doi: 10.1055/s-2001-18365. [PMID: 11731906]
  • E Paulsen, K E Andersen, B M Hausen. Sensitization and cross-reaction patterns in Danish Compositae-allergic patients. Contact dermatitis. 2001 Oct; 45(4):197-204. doi: 10.1034/j.1600-0536.2001.450402.x. [PMID: 11683829]
  • L Kanerva, T Estlander, K Alanko, R Jolanki. Patch test sensitization to Compositae mix, sesquiterpene-lactone mix, Compositae extracts, laurel leaf, Chlorophorin, Mansonone A, and dimethoxydalbergione. American journal of contact dermatitis : official journal of the American Contact Dermatitis Society. 2001 Mar; 12(1):18-24. doi: 10.1053/ajcd.2000.9547. [PMID: 11244135]
  • M P Mateo, M Velasco, F J Miquel, J de la Cuadra. Erythema-multiforme-like eruption following allergic contact dermatitis from sesquiterpene lactones in herbal medicine. Contact dermatitis. 1995 Dec; 33(6):449-50. doi: 10.1111/j.1600-0536.1995.tb02100.x. [PMID: 8706423]
  • N Alonso Blasi, R Fraginals, J P Lepoittevin, C Benezra. A murine in vitro model of allergic contact dermatitis to sesquiterpene alpha-methylene-gamma-butyrolactones. Archives of dermatological research. 1992; 284(5):297-302. doi: 10.1007/bf00372584. [PMID: 1444579]
  • J M Pinedo, F Gonzalez de Canales, J L Hinojosa, P Llamas, B M Hausen. Contact dermatitis to sesquiterpene lactones in Inula viscosa Aiton. Contact dermatitis. 1987 Nov; 17(5):322-3. doi: 10.1111/j.1600-0536.1987.tb01492.x. [PMID: 3325222]
  • P Azoulay, J P Reynier, G Balansard, M Gasquet, P Timon-David. [Helenine and santonine, the 12-carboxy-eudesma-3,11(13) diene]. Pharmaceutica acta Helvetiae. 1986; 61(12):345-52. doi: ". [PMID: 3809210]
  • ". Alantolactone in chrysanthemum extract. Contact dermatitis. 1978 Dec; 4(6):368-9. doi: 10.1111/j.1600-0536.1978.tb03853.x. [PMID: 738042]