Helenalin (BioDeep_00000000649)

   

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


{Azuleno[6,} 5-b]furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a, 8-dimethyl-3-methylene-, {[3aS-(3a.alpha.,4.alpha.,4a.beta.,} 7a.alpha.,8.alpha.,9a.alpha.)]-

化学式: C15H18O4 (262.1205028)
中文名称: 心菊内酯
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 26.09%

分子结构信息

SMILES: C=C1C(=O)OC2CC(C)C3=CC(=O)C(C)C3C(O)C12
InChI: InChI=1S/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7,9-10,12-13,17H,2,6H2,1,3H3/t7-,9+,10-,12-,13+,15+/m1/s1

描述信息

Helenalin is a sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer). It has a role as an anti-inflammatory agent, an antineoplastic agent, a plant metabolite and a metabolite. It is a gamma-lactone, a cyclic ketone, an organic heterotricyclic compound, a sesquiterpene lactone and a secondary alcohol.
Helenalin is a natural product found in Pentanema britannicum, Psilostrophe cooperi, and other organisms with data available.
A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer).
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors
D002491 - Central Nervous System Agents > D000700 - Analgesics
D020011 - Protective Agents > D002316 - Cardiotonic Agents
D000893 - Anti-Inflammatory Agents
D000970 - Antineoplastic Agents
D002317 - Cardiovascular Agents
D018501 - Antirheumatic Agents

同义名列表

53 个代谢物同义名

Azuleno[6,5-b]furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, [3aS-(3a.alpha.,4.alpha.,4a.beta.,7a.alpha.,8.alpha.,9a.alpha.)]-; (3AS-(3A.ALPHA.,4.ALPHA.,4A.BETA.,7A.ALPHA.,8.ALPHA.,9A.ALPHA.))-3,3A,4,4A,7A,8,9,9A-OCTAHYDRO-4-HYDROXY-4A,8-DIMETHYL-3-METHYLENEAZULENO(6,5-B)FURAN-2,5-DIONE; Azuleno[6,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, [3aS-(3a.alpha.,4.alpha.,4a.beta.,7a.alpha.,8.alpha.,9a.alpha.)]-; Azuleno(6,5-b)furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, (3aS-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))-; (3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-Octahydro-4-hydroxy-4abeta,8 alpha-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione; (3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-octahydro-4-hydroxy-4abeta,8alpha-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione; (3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylidene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione; (3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione; (3aR,5R,5aR,8aR,9S,9aS)-5,8a-dimethyl-1-methylidene-9-oxidanyl-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione; (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-quinone; (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione; (3aR,5R,5aR,8aR,9S,9aS)-9-Hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[7,6-d]furan-2,8-dione; (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione; 4-Hydroxy-4a,8-dimethyl-3-methylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione; Ambrosa-2,11(13)-dien-12-oic acid, 6.alpha.,8.beta.-dihydroxy-4-oxo-, 12,8-lactone; Ambrosa-2,11(13)-dien-12-oic acid, 6-alpha,8-beta-dihydroxy-4-oxo-, 12,8-lactone; 6.ALPHA.,8.BETA.-DIHYDROXY-4-OXOAMBROSA-2,11(13)-DIEN-12-OIC ACID 12,8-LACTONE; Ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone; 6alpha,8beta-Dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oic acid 12,8-lactone; Ambrosa-2, 6.alpha.,8.beta.-dihydroxy-4-oxo-, 12,8-lactone; 4-18-00-01434 (Beilstein Handbook Reference); NF-kappaB inhibitor; dihydrohelenalin; HELENALIN [HSDB]; UNII-4GUY9L896T; HELENALIN [MI]; (-)-HELENALIN; NCI60_041870; Helenalin A; 4GUY9L896T; Helenalin; PF 56; {Azuleno[6,} 5-b]furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a, 8-dimethyl-3-methylene-, {[3aS-(3a.alpha.,4.alpha.,4a.beta.,} 7a.alpha.,8.alpha.,9a.alpha.)]-; Azuleno(6,5-b)furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, (3aS-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))- (9CI); (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[7,6-d]furan-2,8-quinone; (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[7,6-d]furan-2,8-dione; Ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone (8CI); Ambrosa-2,11(13)-dien-12-oic acid, 6.alpha., 8.beta.-dihydroxy-4-oxo-, 12,8-lactone; WLN: T C575 DYVO MV KUTJ A1 BQ DU1 I1; NCGC00163416-01; BSPBio_001312; MLS000728512; SMR000445626; BRN 0028081; AIDS-125803; AIDS125803; NSC 85236; HSDB 3490; 6754-13-8; NSC85236; C09473; Helenalin extract; Helenalin



数据库引用编号

19 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。

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65 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

  • Mei Yang, Weihua Zhang, Xiuxiu Yu, Feng Wang, Yeping Li, Yan Zhang, Yu Yang. Helenalin Facilitates Reactive Oxygen Species-Mediated Apoptosis and Cell Cycle Arrest by Targeting Thioredoxin Reductase-1 in Human Prostate Cancer Cells. Medical science monitor : international medical journal of experimental and clinical research. 2021 Jun; 27(?):e930083. doi: 10.12659/msm.930083. [PMID: 34125740]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Priyanka Kriplani, Kumar Guarve. Recent Patents on Anti-Cancer Potential of Helenalin. Recent patents on anti-cancer drug discovery. 2020; 15(2):132-142. doi: 10.2174/1574892815666200702142601. [PMID: 32614752]
  • Yan Li, Yongmei Zeng, Quanfang Huang, Shujuan Wen, Yuanyuan Wei, Ya Chen, Xiaolin Zhang, Facheng Bai, Zhongpeng Lu, Jinbin Wei, Xing Lin. Helenalin from Centipeda minima ameliorates acute hepatic injury by protecting mitochondria function, activating Nrf2 pathway and inhibiting NF-κB activation. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2019 Nov; 119(?):109435. doi: 10.1016/j.biopha.2019.109435. [PMID: 31520915]
  • Jingxin Liu, Yanan Zhao, Zhangzhen Shi, Yuansong Bai. Antitumor effects of helenalin in doxorubicin-resistant leukemia cells are mediated via mitochondrial mediated apoptosis, loss of mitochondrial membrane potential, inhibition of cell migration and invasion and downregulation of PI3-kinase/AKT/m-TOR signalling pathway. Journal of B.U.ON. : official journal of the Balkan Union of Oncology. 2019 Sep; 24(5):2068-2074. doi: . [PMID: 31786877]
  • Joanna Drogosz, Anna Janecka. Helenalin - A Sesquiterpene Lactone with Multidirectional Activity. Current drug targets. 2019; 20(4):444-452. doi: 10.2174/1389450119666181012125230. [PMID: 30317996]
  • Imke F Wulsten, Thais A Costa-Silva, Juliana T Mesquita, Marta L Lima, Mariana K Galuppo, Noemi N Taniwaki, Samanta E T Borborema, Fernando B Da Costa, Thomas J Schmidt, Andre G Tempone. Investigation of the Anti-Leishmania (Leishmania) infantum Activity of Some Natural Sesquiterpene Lactones. Molecules (Basel, Switzerland). 2017 Apr; 22(5):. doi: 10.3390/molecules22050685. [PMID: 28441357]
  • Xing Lin, Shijun Zhang, Renbin Huang, Ling Wei, Shimei Tan, Shuang Liang, Yuanchun Tian, Xiaoyan Wu, Zhongpeng Lu, Quanfang Huang. Helenalin attenuates alcohol-induced hepatic fibrosis by enhancing ethanol metabolism, inhibiting oxidative stress and suppressing HSC activation. Fitoterapia. 2014 Jun; 95(?):203-13. doi: 10.1016/j.fitote.2014.03.020. [PMID: 24704336]
  • Ji Hoon Jang, Taha Iqbal, Kyoung-Jin Min, Shin Kim, Jong-Wook Park, Eun-Ik Son, Tae-Jin Lee, Taeg Kyu Kwon. Helenalin-induced apoptosis is dependent on production of reactive oxygen species and independent of induction of endoplasmic reticulum stress in renal cell carcinoma. Toxicology in vitro : an international journal published in association with BIBRA. 2013 Mar; 27(2):588-96. doi: 10.1016/j.tiv.2012.10.014. [PMID: 23123298]
  • Chuan Bian Lim, Pan You Fu, Nung Ky, Hong Shuang Zhu, XiaoLing Feng, Jinming Li, Kandhadayar Gopalan Srinivasan, Mohamed Sabry Hamza, Yan Zhao. NF-κB p65 repression by the sesquiterpene lactone, Helenalin, contributes to the induction of autophagy cell death. BMC complementary and alternative medicine. 2012 Jul; 12(?):93. doi: 10.1186/1472-6882-12-93. [PMID: 22784363]
  • Peng Wu, Miao-Xian Su, Ying Wang, Guo-Cai Wang, Wen-Cai Ye, Hau-Yin Chung, Juan Li, Ren-Wang Jiang, Yao-Lan Li. Supercritical fluid extraction assisted isolation of sesquiterpene lactones with antiproliferative effects from Centipeda minima. Phytochemistry. 2012 Apr; 76(?):133-40. doi: 10.1016/j.phytochem.2012.01.003. [PMID: 22277736]
  • Jordanka Staneva, Pavletta Denkova, Milka Todorova, Ljuba Evstatieva. Quantitative analysis of sesquiterpene lactones in extract of Arnica montana L. by 1H NMR spectroscopy. Journal of pharmaceutical and biomedical analysis. 2011 Jan; 54(1):94-9. doi: 10.1016/j.jpba.2010.08.018. [PMID: 20837387]
  • Kuo-Hsiung Lee. Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach. Journal of natural products. 2010 Mar; 73(3):500-16. doi: 10.1021/np900821e. [PMID: 20187635]
  • Ji Yun Lee, Bong Jae Cho, Tae Wook Park, Byoung Eun Park, Soo Jung Kim, Sang Soo Sim, Chang Jong Kim. Dibenzylbutyrolactone lignans from Forsythia koreana fruits attenuate lipopolysaccharide-induced inducible nitric oxide synthetase and cyclooxygenase-2 expressions through activation of nuclear factor-κb and mitogen-activated protein kinase in RAW264.7 cells. Biological & pharmaceutical bulletin. 2010; 33(11):1847-53. doi: 10.1248/bpb.33.1847. [PMID: 21048310]
  • Kirandeep Kaur, Meenakshi Jain, Tarandeep Kaur, Rahul Jain. Antimalarials from nature. Bioorganic & medicinal chemistry. 2009 May; 17(9):3229-56. doi: 10.1016/j.bmc.2009.02.050. [PMID: 19299148]
  • Nigel B Perry, Elaine J Burgess, Manuel A Rodríguez Guitián, Rosa Romero Franco, Elvira López Mosquera, Bruce M Smallfield, Nigel I Joyce, Roger P Littlejohn. Sesquiterpene lactones in Arnica montana: helenalin and dihydrohelenalin chemotypes in Spain. Planta medica. 2009 May; 75(6):660-6. doi: 10.1055/s-0029-1185362. [PMID: 19235681]
  • Shurong Huang, Ling Zhao, Kihoon Kim, Dong Seok Lee, Daniel H Hwang. Inhibition of Nod2 signaling and target gene expression by curcumin. Molecular pharmacology. 2008 Jul; 74(1):274-81. doi: 10.1124/mol.108.046169. [PMID: 18413660]
  • Valentina Bergamante, Gian Carlo Ceschel, Sergio Marazzita, Celestino Ronchi, Adamo Fini. Effect of vehicles on topical application of aloe vera and arnica montana components. Drug delivery. 2007 Oct; 14(7):427-32. doi: 10.1080/10717540701202960. [PMID: 17994359]
  • Mary Kaileh, Wim Vanden Berghe, Arne Heyerick, Julie Horion, Jacques Piette, Claude Libert, Denis De Keukeleire, Tamer Essawi, Guy Haegeman. Withaferin a strongly elicits IkappaB kinase beta hyperphosphorylation concomitant with potent inhibition of its kinase activity. The Journal of biological chemistry. 2007 Feb; 282(7):4253-4264. doi: 10.1074/jbc.m606728200. [PMID: 17150968]
  • Steen Lisby, Annesofie Faurschou, Robert Gniadecki. The autocrine TNFalpha signalling loop in keratinocytes requires atypical PKC species and NF-kappaB activation but is independent of cholesterol-enriched membrane microdomains. Biochemical pharmacology. 2007 Feb; 73(4):526-33. doi: 10.1016/j.bcp.2006.11.006. [PMID: 17145042]
  • Steffen Wagner, Irmgard Merfort. Skin penetration behaviour of sesquiterpene lactones from different Arnica preparations using a validated GC-MSD method. Journal of pharmaceutical and biomedical analysis. 2007 Jan; 43(1):32-8. doi: 10.1016/j.jpba.2006.06.008. [PMID: 16930911]
  • Vichit Supornsilchai, Olle Söder, Konstantin Svechnikov. Sesquiterpene lactone helenalin suppresses Leydig and adrenocortical cell steroidogenesis by inhibiting expression of the steroidogenic acute regulatory protein. Reproductive toxicology (Elmsford, N.Y.). 2006 Nov; 22(4):631-5. doi: 10.1016/j.reprotox.2006.04.011. [PMID: 16777379]
  • Hyung S Youn, Shin I Saitoh, Kensuke Miyake, Daniel H Hwang. Inhibition of homodimerization of Toll-like receptor 4 by curcumin. Biochemical pharmacology. 2006 Jun; 72(1):62-9. doi: 10.1016/j.bcp.2006.03.022. [PMID: 16678799]
  • Anna Rita Bilia, Maria Camilla Bergonzi, Giovanni Mazzi, Franco Francesco Vincieri. Development and stability of semisolid preparations based on a supercritical CO2 Arnica extract. Journal of pharmaceutical and biomedical analysis. 2006 May; 41(2):449-54. doi: 10.1016/j.jpba.2005.12.024. [PMID: 16457981]
  • Laura Casu, Leonardo Bonsignore, Manuela Pinna, Mariano Casu, Costantino Floris, Jürg Gertsch, Filippo Cottiglia. Cytotoxic diacetylenic spiroketal enol ethers from Plagius flosculosus. Journal of natural products. 2006 Feb; 69(2):295-8. doi: 10.1021/np0504513. [PMID: 16499337]
  • Eske Voss, Jan Wehkamp, Kai Wehkamp, Eduard F Stange, Jens M Schröder, Jürgen Harder. NOD2/CARD15 mediates induction of the antimicrobial peptide human beta-defensin-2. The Journal of biological chemistry. 2006 Jan; 281(4):2005-11. doi: 10.1074/jbc.m511044200. [PMID: 16319062]
  • Verónica Jimenez-Ortiz, Silvia D Brengio, Oscar Giordano, Carlos Tonn, Matías Sánchez, Mario H Burgos, Miguel A Sosa. The trypanocidal effect of sesquiterpene lactones helenalin and mexicanin on cultured epimastigotes. The Journal of parasitology. 2005 Feb; 91(1):170-4. doi: 10.1645/ge-3373. [PMID: 15856894]
  • S Tornhamre, T J Schmidt, B Näsman-Glaser, I Ericsson, Lindgren JA. Inhibitory effects of helenalin and related compounds on 5-lipoxygenase and leukotriene C(4) synthase in human blood cells. Biochemical pharmacology. 2001 Oct; 62(7):903-11. doi: 10.1016/s0006-2952(01)00729-8. [PMID: 11543725]
  • W Schaffner. Granny's remedy explained at the molecular level: helenalin inhibits NF-kappaB. Biological chemistry. 1997 Sep; 378(9):935. doi: ". [PMID: 9348102]
  • G Lyss, T J Schmidt, I Merfort, H L Pahl. Helenalin, an anti-inflammatory sesquiterpene lactone from Arnica, selectively inhibits transcription factor NF-kappaB. Biological chemistry. 1997 Sep; 378(9):951-61. doi: 10.1515/bchm.1997.378.9.951. [PMID: 9348104]
  • G Powis, A Gallegos, R T Abraham, C L Ashendel, L H Zalkow, G B Grindey, R Bonjouklian. Increased intracellular Ca2+ signaling caused by the antitumor agent helenalin and its analogues. Cancer chemotherapy and pharmacology. 1994; 34(4):344-50. doi: 10.1007/bf00686043. [PMID: 8033301]
  • D E Chapman, D J Holbrook, S G Chaney, I H Hall, K H Lee. In vivo and in vitro effects of helenalin on mouse hepatic microsomal cytochrome P450. Biochemical pharmacology. 1991 Jan; 41(2):229-35. doi: 10.1016/0006-2952(91)90481-j. [PMID: 1989634]
  • I H Hall, A A Grippo, D J Holbrook, J J Chang, L M Yang, S G Chaney, K H Lee. Renal, hepatic, cardiac and thymic acute toxicity afforded by bis(helenalinyl)malonate in BDF1 mice. Toxicology. 1990 Nov; 64(2):205-16. doi: 10.1016/0300-483x(90)90136-5. [PMID: 2219141]
  • I H Hall, A A Grippo, D J Holbrook, G Roberts, H C Lin, H L Kim, K H Lee. Role of thiol agents in protecting against the toxicity of helenalin in tumor-bearing mice. Planta medica. 1989 Dec; 55(6):513-7. doi: 10.1055/s-2006-962083. [PMID: 2616670]
  • D E Chapman, G B Roberts, D J Reynolds, A A Grippo, D J Holbrook, I H Hall, S G Chaney, J Chang, K H Lee. Acute toxicity of helenalin in BDF1 mice. Fundamental and applied toxicology : official journal of the Society of Toxicology. 1988 Feb; 10(2):302-12. doi: . [PMID: 3356317]
  • A R Gaspar, J A Verschoor, A W Neitz, N M Vermeulen. The influence of the sesquiterpene lactones from Geigeria on mast cell degranulation. Biochemical pharmacology. 1987 Aug; 36(15):2461-5. doi: 10.1016/0006-2952(87)90517-x. [PMID: 2440443]
  • M Itoigawa, K Takeya, H Furukawa, K Ito. Mode of cardiotonic action of helenalin, a sesquiterpene lactone, on guinea pig ventricular myocardium. Journal of cardiovascular pharmacology. 1987 Feb; 9(2):193-201. doi: 10.1097/00005344-198702000-00011. [PMID: 2435998]
  • A C Anderson, H L Kim. Depletion and resynthesis of tissue thiols by helenalin and tenulin. Drug and chemical toxicology. 1986; 9(1):75-81. doi: 10.3109/01480548609042832. [PMID: 3743464]
  • B M Hausen. [Arnica allergy]. Der Hautarzt; Zeitschrift fur Dermatologie, Venerologie, und verwandte Gebiete. 1980 Jan; 31(1):10-7. doi: . [PMID: 6993423]
  • K H Lee, M Haruna, H C Huang, B S Wu, I H Hall. Antitumor agents XXIII: Helenalin, and antitumor principle from Anaphalis morrisonicola HAY. Journal of pharmaceutical sciences. 1977 Aug; 66(8):1194-5. doi: 10.1002/jps.2600660836. [PMID: 561183]
  • K H Lee, I H Hall, E C Mar, C O Starnes, S A ElGebaly, T G Waddell, R I HADGRAFT, C G Ruffner, I Weidner. Sesquiterpene antitumor agents: inhibitors of cellular metabolism. Science (New York, N.Y.). 1977 Apr; 196(4289):533-6. doi: 10.1126/science.191909. [PMID: 191909]
  • D A Witzel, W Ivie, J W Dollahite. Mammalian toxicity of helenalin, the toxic principle of Helenium microcephalum CD (smallhead sneezeweed). American journal of veterinary research. 1976 Jul; 37(7):859-61. doi: . [PMID: 937811]