| 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: | 6754-13-8 |  3D/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, Edge or firefox) |
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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:
Suppliers:
Safety Information:
| |
| 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 |
| AIDS Citations:Search |
| 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:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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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