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helenalin
(3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-octahydro-4-hydroxy-4abeta,8 alpha-dimethyl-3-methylene azuleno(6,5-b)furan-2,5-dione

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Name:(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
CAS Number: 6754-13-8Picture of molecule3D/inchi
FDA UNII:4GUY9L896T
Nikkaji Web:J21.229F
Beilstein Number:0028081
XlogP3-AA:1.40 (est)
Molecular Weight:262.30526000
Formula:C15 H18 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 167.00 to 168.00 °C. @ 760.00 mm Hg
Boiling Point: 473.00 to 474.00 °C. @ 760.00 mm Hg (est)
Flash Point: 356.00 °F. TCC ( 179.90 °C. ) (est)
logP (o/w): 0.870
Soluble in:
 water, 1.181e+004 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Flavor Type: bitter
bitter
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Helenalin > 95%
Odor: characteristic
Use: Helenalin is a sesquiterpene lactone found in Arnica montana and Arnica chamissonis foliosa. It is a highly toxic compound, with hepatic and lymphatic tissues particularly vulnerable to its effects.
EMD Millipore
For experimental / research use only.
Helenalin, A. chamissonis ssp. foliosa
Glentham Life Sciences
Helenalin
Santa Cruz Biotechnology
For experimental / research use only.
Helenalin >97%
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 125 mg/kg
Pharmazie in Unserer Zeit. Vol. 10, Pg. 1, 1981.

oral-rabbit LD50 90 mg/kg
Pharmazie in Unserer Zeit. Vol. 10, Pg. 1, 1981.

oral-mouse LD50 150 mg/kg
American Journal of Veterinary Research. Vol. 37, Pg. 859, 1976.

intraperitoneal-mouse LD50 10 mg/kg
Research Communications in Chemical Pathology and Pharmacology. Vol. 28, Pg. 189, 1980.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for helenalin usage levels up to:
 not for fragrance use.
 
Recommendation for helenalin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :23205
National Institute of Allergy and Infectious Diseases:Data
(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
Chemidplus:0006754138
 
References:
 (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
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):23205
Pubchem (sid):134987514
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09473
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 arnica montana
Search Trop Picture
 helenium microcephalum
Search Trop Picture
 
Synonyms:
(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
(3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-octahydro-4-hydroxy-4abeta,8 alpha-dimethyl-3-methylene azuleno(6,5-b)furan-2,5-dione
 

Articles:

PubMed:Natural sesquiterpene lactones induce programmed cell death in Trypanosoma cruzi: A new therapeutic target?
PubMed:Hydrocortisone normalizes phosphodiesterase-5 activity in pulmonary artery smooth muscle cells from lambs with persistent pulmonary hypertension of the newborn.
PubMed:Interleukin 17A promotes gastric cancer invasiveness via NF-κB mediated matrix metalloproteinases 2 and 9 expression.
PubMed:PAR-1-dependent COX-2/PGE2 production contributes to cell proliferation via EP2 in primary human cardiomyocytes.
PubMed:The inhibitory effect of helenalin on telomerase activity is attributed to the alkylation of the CYS445 residue: evidence from QM/MM simulations.
PubMed:Helenalin attenuates alcohol-induced hepatic fibrosis by enhancing ethanol metabolism, inhibiting oxidative stress and suppressing HSC activation.
PubMed:Analysis of gene profiles involved in the enhancement of all-trans retinoic acid-induced HL-60 cell differentiation by sesquiterpene lactones identifies asparagine synthetase as a novel target for differentiation-inducing therapy.
PubMed:Inhibitory effects of β-cyclodextrin-helenalin complexes on H-TERT gene expression in the T47D breast cancer cell line - results of real time quantitative PCR.
PubMed:TBK1-targeted suppression of TRIF-dependent signaling pathway of Toll-like receptors by helenalin.
PubMed:Delta-opioid receptors attenuate TNF-α-induced MMP-2 secretion from human ONH astrocytes.
PubMed:The archaic roles of the amphioxus NF-κB/IκB complex in innate immune responses.
PubMed:NF-κB-dependent and -independent pathways in the protective effects of activated protein C in hippocampal and cortical neurons at excitotoxicity.
PubMed:Natural sesquiterpene lactones as inhibitors of Myb-dependent gene expression: structure-activity relationships.
PubMed:IL-8 production in response to cigarette smoke is decreased in epithelial cells from COPD patients.
PubMed:Helenalin-induced apoptosis is dependent on production of reactive oxygen species and independent of induction of endoplasmic reticulum stress in renal cell carcinoma.
PubMed:Th17-associated cytokines promote human airway smooth muscle cell proliferation.
PubMed:Hepatitis B virus surface antigen can activate human monocyte-derived dendritic cells by nuclear factor kappa B and p38 mitogen-activated protein kinase mediated signaling.
PubMed:NF-κB p65 repression by the sesquiterpene lactone, Helenalin, contributes to the induction of autophagy cell death.
PubMed:Sesquiterpene lactones and the diterpene 5-epi-icetexone affect the intracellular and extracellular stages of Trypanosoma cruzi.
PubMed:PI3-K/Akt/JNK/NF-κB is essential for MMP-9 expression and outgrowth in human limbal epithelial cells on intact amniotic membrane.
PubMed:Supercritical fluid extraction assisted isolation of sesquiterpene lactones with antiproliferative effects from Centipeda minima.
PubMed:Solution and solid-state effects on NMR chemical shifts in sesquiterpene lactones: NMR, X-ray, and theoretical methods.
PubMed:Helenalin bypasses Bcl-2-mediated cell death resistance by inhibiting NF-κB and promoting reactive oxygen species generation.
PubMed:Inhibition of pattern recognition receptor-mediated inflammation by bioactive phytochemicals.
PubMed:Mycobacterium tuberculosis-infected human monocytes down-regulate microglial MMP-2 secretion in CNS tuberculosis via TNFα, NFκB, p38 and caspase 8 dependent pathways.
PubMed:Perspectives on sesquiterpene lactones in inflammation and cancer.
PubMed:Activation and induction of cytosolic phospholipase A2 by TNF-α mediated through Nox2, MAPKs, NF-κB, and p300 in human tracheal smooth muscle cells.
PubMed: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.
PubMed:Quantitative analysis of sesquiterpene lactones in extract of Arnica montana L. by 1H NMR spectroscopy.
PubMed:A novel phycobiliprotein alleviates allergic airway inflammation by modulating immune responses.
PubMed:Japanese encephalitis virus induces matrix metalloproteinase-9 in rat brain astrocytes via NF-κB signalling dependent on MAPKs and reactive oxygen species.
PubMed:Interleukin-1beta induces ICAM-1 expression enhancing leukocyte adhesion in human rheumatoid arthritis synovial fibroblasts: involvement of ERK, JNK, AP-1, and NF-kappaB.
PubMed:EV71 induces COX-2 expression via c-Src/PDGFR/PI3K/Akt/p42/p44 MAPK/AP-1 and NF-kappaB in rat brain astrocytes.
PubMed:Surface plasmon resonance analysis of nuclear factor-kappaB protein interactions with the sesquiterpene lactone helenalin.
PubMed:Cooperation of TLR2 with MyD88, PI3K, and Rac1 in lipoteichoic acid-induced cPLA2/COX-2-dependent airway inflammatory responses.
PubMed:Variation of sesquiterpene lactone contents in different Arnica montana populations: influence of ecological parameters.
PubMed:Activation and induction of cytosolic phospholipase A2 by IL-1beta in human tracheal smooth muscle cells: role of MAPKs/p300 and NF-kappaB.
PubMed:Involvement of MAPKs and NF-kappaB in tumor necrosis factor alpha-induced vascular cell adhesion molecule 1 expression in human rheumatoid arthritis synovial fibroblasts.
PubMed:Induction of COX-2/PGE(2)/IL-6 is crucial for cigarette smoke extract-induced airway inflammation: Role of TLR4-dependent NADPH oxidase activation.
PubMed:Cigarette smoke extract induces COX-2 expression via a PKCalpha/c-Src/EGFR, PDGFR/PI3K/Akt/NF-kappaB pathway and p300 in tracheal smooth muscle cells.
PubMed:Helenalin suppresses essential immune functions of activated CD4+ T cells by multiple mechanisms.
PubMed:IL-1 beta promotes A549 cell migration via MAPKs/AP-1- and NF-kappaB-dependent matrix metalloproteinase-9 expression.
PubMed:Effects of hyaluronan oligosaccharide on the expression of MMP-1 in periodontal ligament cells.
PubMed:Quantitative structure--antiprotozoal activity relationships of sesquiterpene lactones.
PubMed:An immunomodulatory protein, Ling Zhi-8, induced activation and maturation of human monocyte-derived dendritic cells by the NF-kappaB and MAPK pathways.
PubMed:Dimethylfumarate inhibits NF-{kappa}B function at multiple levels to limit airway smooth muscle cell cytokine secretion.
PubMed:Cigarette smoke extract induces cytosolic phospholipase A2 expression via NADPH oxidase, MAPKs, AP-1, and NF-kappaB in human tracheal smooth muscle cells.
PubMed:Sesquiterpene lactones in Arnica montana: helenalin and dihydrohelenalin chemotypes in Spain.
PubMed:Functional coupling expression of COX-2 and cPLA2 induced by ATP in rat vascular smooth muscle cells: role of ERK1/2, p38 MAPK, and NF-kappaB.
PubMed:IL-1 beta induces urokinase-plasminogen activator expression and cell migration through PKC alpha, JNK1/2, and NF-kappaB in A549 cells.
PubMed:New eudesmane derivatives and other sesquiterpenes from the epigeal parts of Dittrichia graveolens.
PubMed:Helenalin-mediated post-transcriptional regulation of p21(Cip1) inhibits 3T3-L1 preadipocyte proliferation.
PubMed:Differential enhancement of leukaemia cell differentiation without elevation of intracellular calcium by plant-derived sesquiterpene lactone compounds.
PubMed:Involvement of MAPKs, NF-kappaB and p300 co-activator in IL-1beta-induced cytosolic phospholipase A2 expression in canine tracheal smooth muscle cells.
PubMed:Calbindin-D28K expression induced by glial cell line-derived neurotrophic factor in substantia nigra neurons dependent on PI3K/Akt/NF-kappaB signaling pathway.
PubMed:Charting calcium-regulated apoptosis pathways using chemical biology: role of calmodulin kinase II.
PubMed:Natural sesquiterpene lactones are active against Leishmania mexicana.
PubMed:PKC-delta/c-Src-mediated EGF receptor transactivation regulates thrombin-induced COX-2 expression and PGE(2) production in rat vascular smooth muscle cells.
PubMed:Tumor necrosis factor-alpha induces MMP-9 expression via p42/p44 MAPK, JNK, and nuclear factor-kappaB in A549 cells.
PubMed:Effect of vehicles on topical application of aloe vera and arnica montana components.
PubMed:Sphingosine 1-phosphate induces EGFR expression via Akt/NF-kappaB and ERK/AP-1 pathways in rat vascular smooth muscle cells.
PubMed:EV71 induces VCAM-1 expression via PDGF receptor, PI3-K/Akt, p38 MAPK, JNK and NF-kappaB in vascular smooth muscle cells.
PubMed:The effect of 17beta-estradiol on IL-6 secretion and NF-kappaB DNA-binding activity in human retinal pigment epithelial cells.
PubMed:The opioid antagonist, beta-funaltrexamine, inhibits chemokine expression in human astroglial cells.
PubMed:Interleukin-1beta induces MMP-9 expression via p42/p44 MAPK, p38 MAPK, JNK, and nuclear factor-kappaB signaling pathways in human tracheal smooth muscle cells.
PubMed:Involvement of MAPKs and NF-kappaB in LPS-induced VCAM-1 expression in human tracheal smooth muscle cells.
PubMed:Transactivation of Src, PDGF receptor, and Akt is involved in IL-1beta-induced ICAM-1 expression in A549 cells.
PubMed:Sesquiterpene lactone content in leaves of in vitro and field cultivated Arnica montana.
PubMed:TNF-alpha induces MMP-9 expression via activation of Src/EGFR, PDGFR/PI3K/Akt cascade and promotion of NF-kappaB/p300 binding in human tracheal smooth muscle cells.
PubMed:The autocrine TNFalpha signalling loop in keratinocytes requires atypical PKC species and NF-kappaB activation but is independent of cholesterol-enriched membrane microdomains.
PubMed:Helenalin reduces Staphylococcus aureus infection in vitro and in vivo.
PubMed:BK-induced COX-2 expression via PKC-delta-dependent activation of p42/p44 MAPK and NF-kappaB in astrocytes.
PubMed:Skin penetration behaviour of sesquiterpene lactones from different Arnica preparations using a validated GC-MSD method.
PubMed:Sesquiterpene lactone helenalin suppresses Leydig and adrenocortical cell steroidogenesis by inhibiting expression of the steroidogenic acute regulatory protein.
PubMed:Lipopolysaccharide induces CXCL2/macrophage inflammatory protein-2 gene expression in enterocytes via NF-kappaB activation: independence from endogenous TNF-alpha and platelet-activating factor.
PubMed:Novel effect of helenalin on Akt signaling and Skp2 expression in 3T3-L1 preadipocytes.
PubMed:BLIMP-1 is a target of cellular stress and downstream of the unfolded protein response.
PubMed:Low doses of ouabain protect from serum deprivation-triggered apoptosis and stimulate kidney cell proliferation via activation of NF-kappaB.
PubMed:Hyaluronan oligosaccharides induce matrix metalloproteinase 13 via transcriptional activation of NFkappaB and p38 MAP kinase in articular chondrocytes.
PubMed:TNF-alpha-induced optic nerve degeneration and nuclear factor-kappaB p65.
PubMed:Delayed radioprotection by nuclear transcription factor kappaB -mediated induction of manganese superoxide dismutase in human microvascular endothelial cells after exposure to the free radical scavenger WR1065.
PubMed:Nuclear factor-kappaB p65 and upregulation of interleukin-6 in retinal ischemia/reperfusion injury in rats.
PubMed:Porphyromonas gingivalis enhances FasL expression via up-regulation of NFkappaB-mediated gene transcription and induces apoptotic cell death in human gingival epithelial cells.
PubMed:Sphingosine-1-phosphate induces COX-2 expression via PI3K/Akt and p42/p44 MAPK pathways in rat vascular smooth muscle cells.
PubMed:Development and stability of semisolid preparations based on a supercritical CO2 Arnica extract.
PubMed:Pseudomonas aeruginosa- and IL-1beta-mediated induction of human beta-defensin-2 in keratinocytes is controlled by NF-kappaB and AP-1.
PubMed:Involvement of Nrf2, p38, B-Raf, and nuclear factor-kappaB, but not phosphatidylinositol 3-kinase, in induction of hemeoxygenase-1 by dietary polyphenols.
PubMed:New sesquiterpene lactones from Arnica tincture prepared from fresh flowerheads of Arnica montana.
PubMed:NOD2/CARD15 mediates induction of the antimicrobial peptide human beta-defensin-2.
PubMed:Transcriptional regulation of VCAM-1 expression by tumor necrosis factor-alpha in human tracheal smooth muscle cells: involvement of MAPKs, NF-kappaB, p300, and histone acetylation.
PubMed:Induction of cytosolic phospholipase A2 by lipopolysaccharide in canine tracheal smooth muscle cells: involvement of MAPKs and NF-kappaB pathways.
PubMed:Induction of clusterin/apoJ expression by histone deacetylase inhibitors in neural cells.
PubMed:Potent inhibition of human telomerase by helenalin.
PubMed:Activation of nuclear factor-kappaB contributes to induction of death receptors and apoptosis by the synthetic retinoid CD437 in DU145 human prostate cancer cells.
PubMed:BK-induced cytosolic phospholipase A2 expression via sequential PKC-delta, p42/p44 MAPK, and NF-kappaB activation in rat brain astrocytes.
PubMed:Apoptosis induction by a novel retinoid-related molecule requires nuclear factor-kappaB activation.
PubMed:Pseudoguanolide sesquiterpene lactones from Vernoniopsis caudata and their in vitro antiplasmodial activities.
PubMed:Polysaccharide purified from Ganoderma lucidum induced activation and maturation of human monocyte-derived dendritic cells by the NF-kappaB and p38 mitogen-activated protein kinase pathways.
PubMed:Effects of mechanistically distinct NF-kappaB inhibitors on glial inducible nitric-oxide synthase expression.
PubMed:The trypanocidal effect of sesquiterpene lactones helenalin and mexicanin on cultured epimastigotes.
PubMed:Induction of human leukemia HL-60 cell differentiation via a PKC/ERK pathway by helenalin, a pseudoguainolide sesquiterpene lactone.
PubMed:NF-kappaB activation plays a role in superoxide-mediated cerebral endothelial dysfunction after hypoxia/reoxygenation.
PubMed:New triterpene esters from flowerheads of Arnica lonchophylla.
PubMed:Skin penetration studies of Arnica preparations and of their sesquiterpene lactones.
PubMed:Involvement of p42/p44 MAPK, p38 MAPK, JNK, and NF-kappaB in IL-1beta-induced VCAM-1 expression in human tracheal smooth muscle cells.
PubMed:Involvement of p42/p44 MAPK, JNK, and NF-kappaB in IL-1beta-induced ICAM-1 expression in human pulmonary epithelial cells.
PubMed:NF-kappaB- and AP-1-mediated induction of human beta defensin-2 in intestinal epithelial cells by Escherichia coli Nissle 1917: a novel effect of a probiotic bacterium.
PubMed:Involvement of p42/p44 MAPK, p38 MAPK, JNK and nuclear factor-kappa B in interleukin-1beta-induced matrix metalloproteinase-9 expression in rat brain astrocytes.
PubMed:Intracellular signalings underlying bradykinin-induced matrix metalloproteinase-9 expression in rat brain astrocyte-1.
PubMed:In vitro behaviour of sesquiterpene lactones and sesquiterpene lactone-containing plant preparations in human blood, plasma and human serum albumin solutions.
PubMed:Involvement of nuclear factor kappa B in the regulation of rat luteal function: potential roles as survival factor and inhibitor of 20alpha-hydroxysteroid dehydrogenase.
PubMed:Pseudoguaianolide sesquiterpene lactones with high activities against the human malaria parasite Plasmodium falciparum.
PubMed:Sesquiterpene lactones in Arnica montana: a rapid analytical method and the effects of flower maturity and simulated mechanical harvesting on quality and yield.
PubMed:Influence of helenanolide-type sesquiterpene lactones on gene transcription profiles in Jurkat T cells and human peripheral blood cells: anti-inflammatory and cytotoxic effects.
PubMed:Regulation of microglial inflammatory response by histone deacetylase inhibitors.
PubMed:Modulation of human beta-defensin-2 transcription in pulmonary epithelial cells by lipopolysaccharide-stimulated mononuclear phagocytes via proinflammatory cytokine production.
PubMed:Apoptosis induction by the dual-action DNA- and protein-reactive antitumor drug irofulven is largely Bcl-2-independent.
PubMed:Characterization of the molecular events following impairment of NF-kappaB-driven transcription in neurons.
PubMed:Melanoma cell migration to type IV collagen requires activation of NF-kappaB.
PubMed:Anti-trypanosomal activity of helenalin and some structurally related sesquiterpene lactones.
PubMed:Inhibitory effects of helenalin and related compounds on 5-lipoxygenase and leukotriene C(4) synthase in human blood cells.
PubMed:Cytotoxic sesquiterpene lactones mediate their death-inducing effect in leukemia T cells by triggering apoptosis.
PubMed:The influence of glutathione and cysteine levels on the cytotoxicity of helenanolide type sesquiterpene lactones against KB cells.
PubMed:Helenalin triggers a CD95 death receptor-independent apoptosis that is not affected by overexpression of Bcl-x(L) or Bcl-2.
PubMed:Effect of sesquiterpene lactones on antioxidant enzymes and some drug-metabolizing enzymes in rat liver and kidney.
PubMed:Glutathione adducts of helenalin and 11 alpha,13-dihydrohelenalin acetate inhibit glutathione S-transferase from horse liver.
PubMed:Helenanolide type sesquiterpene lactones. Part 5: the role of glutathione addition under physiological conditions.
PubMed:Cytotoxic activities of hypocretenolides from Leontodon hispidus.
PubMed:Effect of several sesquiterpene lactones on lipid peroxidation and glutathione level.
PubMed:Cytotoxic sesquiterpene lactones from Inula britannica.
PubMed:The anti-inflammatory sesquiterpene lactone helenalin inhibits the transcription factor NF-kappaB by directly targeting p65.
PubMed:Helenalin, an anti-inflammatory sesquiterpene lactone from Arnica, selectively inhibits transcription factor NF-kappaB.
PubMed:Granny's remedy explained at the molecular level: helenalin inhibits NF-kappaB.
PubMed:Helenanolide-type sesquiterpene lactones--III. Rates and stereochemistry in the reaction of helenalin and related helenanolides with sulfhydryl containing biomolecules.
PubMed:Structure-cytotoxicity relationships of some helenanolide-type sesquiterpene lactones.
PubMed:Decreased helenalin-induced cytotoxicity by flavonoids from Arnica as studied in a human lung carcinoma cell line.
PubMed:Recent studies on the zoopharmacognosy, pharmacology and neurotoxicology of sesquiterpene lactones.
PubMed:[Reductive effect of the sesquiterpenic lactone "Helenalin " and its metallic derivatives in the formation of the estradiol receptor complex in breast tumor tissue].
PubMed:Cytotoxicity of flavonoids and sesquiterpene lactones from Arnica species against the GLC4 and the COLO 320 cell lines.
PubMed:Structure-activity relationship in the cytoprotective effect of helenalin and related compounds.
PubMed:Increased intracellular Ca2+ signaling caused by the antitumor agent helenalin and its analogues.
PubMed:Helenalin Acetate in in vitro Propagated Plants of Arnica montana.
PubMed:The cytotoxicity of helenalin, its mono and difunctional esters, and related sesquiterpene lactones in murine and human tumor cells.
PubMed:Disposition of an antineoplastic sesquiterpene lactone, [3H]-plenolin, in BDF1 mice.
PubMed:In vivo and in vitro effects of helenalin on mouse hepatic microsomal cytochrome P450.
PubMed:Renal, hepatic, cardiac and thymic acute toxicity afforded by bis(helenalinyl)malonate in BDF1 mice.
PubMed:Helenalin and 11 alpha,13-dihydrohelenalin, two constituents from Arnica montana L., inhibit human platelet function via thiol-dependent pathways.
PubMed:Role of thiol agents in protecting against the toxicity of helenalin in tumor-bearing mice.
PubMed:In vitro inhibition of mouse hepatic mixed-function oxidase enzymes by helenalin and alantolactone.
PubMed:Effects of sesquiterpene lactones on mitochondrial oxidative phosphorylation.
PubMed:Acute toxicity of helenalin in BDF1 mice.
PubMed:Inhibition of nucleic acid synthesis in P-388 lymphocytic leukemia tumor cells by helenalin and bis(helenalinyl)malonate in vivo.
PubMed:Role of glutathione in the toxicity of the sesquiterpene lactones hymenoxon and helenalin.
PubMed:Inhibition of nucleic acid synthesis in P-388 lymphocytic leukemia cells in culture by sesquiterpene lactones.
PubMed:Effect of helenalin and bis(helenalinyl)malonate on nucleic acid and protein synthesis in human KB carcinoma cells.
PubMed:The influence of the sesquiterpene lactones from Geigeria on mast cell degranulation.
PubMed:Effects of glutathione depletion on the cytotoxicity of agents toward a human colonic tumour cell line.
PubMed:Anti-inflammatory agents; IV. Structure activity relationships of sesquiterpene lactone esters derived from helenalin.
PubMed:Mode of cardiotonic action of helenalin, a sesquiterpene lactone, on guinea pig ventricular myocardium.
PubMed:Inhibition of macrophage adenylate cyclase by the alpha-methylene-gamma-lactone moiety of sesquiterpene lactones from forage plants.
PubMed:Helenalin: mechanism of toxic action.
PubMed:Depletion and resynthesis of tissue thiols by helenalin and tenulin.
PubMed:Antitumor agents 68: effects of a series of helenalin derivatives on P-388 lymphocytic leukemia nucleic acid and protein synthesis.
PubMed:Indirect inactivation of rabbit reticulocyte initiation factor eIF-2 by helenalin and bis(helenalinyl) malonate.
PubMed:[Helenalin- and 11,13-Dihydrohelenalinester from Flowers of Arnica montana.].
PubMed:Considerations of the structure of sesquiterpene lactones on biological activity: influence of the alpha-methylene-gamma-lactone moiety on mast cell degranulation.
PubMed:Antitumor agents LXIII: the effects of microlenin on nucleic acid and protein syntheses of Ehrlich ascites cells.
PubMed:Selective inactivation of rabbit reticulocyte initiation factor eIF-3 by helenalin.
PubMed:Positive inotropic effect of helenalin, a sesquiterpene lactone, on guinea-pig myocardium.
PubMed:Investigation of sesquiterpene lactones as protein synthesis inhibitors of P-388 lymphocytic leukemia cells.
PubMed:Inhibition of glutathione synthesis augments lysis of murine tumor cells by sulfhydryl-reactive antineoplastics.
PubMed:[Helenalin und seine Derivate, die herzwirksamen Verbindungen der Arnikablüten.]
PubMed:Antitumor agents XLII: Comparison of antileukemic activity of helenalin, brusatol, and bruceantin and their esters on different strains of P-388 lymphocytic leukemic cells.
PubMed:DNA damaging effects of three sesquiterpene lactones in repair-deficient mutants of Bacillus subtilis.
PubMed:Toxicity of sesquiterpene lactones.
PubMed:[Arnica allergy].
PubMed:Anti-inflammatory activity of sesquiterpene lactones and related compounds.
PubMed:Antitumor agents 32. Synthesis and antitumor activity of cyclopentenone derivatives related to helenalin.
PubMed:Antitumor agents. 31. Helenalin sym-dimethylethylenediamine reaction products and related derivatives.
PubMed:Antitumor agents XXVII: Effects of helenalin on anaerobic and aerobic metabolism of Ehrlich ascites cells.
PubMed:The sensitizing capacity of Compositae plants. I. Occupational contact dermatitis from Arnica longifolia Eaton.
PubMed:Antitumor agents XXIII: Helenalin, and antitumor principle from Anaphalis morrisonicola HAY.
PubMed:Sesquiterpene antitumor agents: inhibitors of cellular metabolism.
PubMed:Antitumor agents. 21. A proposed mechanism for inhibition of cancer growth by tenulin and helenalin and related cyclopentenones.
PubMed:Mammalian toxicity of helenalin, the toxic principle of Helenium microcephalum CD (smallhead sneezeweed).
PubMed:Antitumor agents. 11. Synthesis and cytotoxic activity of epoxides of helenalin related derivatives.
PubMed:Reaction of helenalin with hydrogen chloride.
PubMed:Antitumor agents. V. Effect of epoxidation on cytotoxicity of helenalin-related derivatives.
PubMed:Antitumor agents. 4. Cytotoxicity and in vitro activity of helenalin esters and related derivatives.
PubMed:Antineoplastic agents. 32. The pseudoguaianolide helenalin.
PubMed:Antitumor agents. 3. Synthesis and cytotoxic activity of helenalin amine adducts and related derivatives.
PubMed:The mass spectra of pseudoguaianolides related to helenalin.
 
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