Helenalin

CAS# 6754-13-8

Helenalin

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Chemical structure

Helenalin

3D structure

Chemical Properties of Helenalin

Cas No. 6754-13-8 SDF Download SDF
PubChem ID 23205 Appearance Powder
Formula C15H18O4 M.Wt 262.30
Type of Compound Sesquiterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical 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
SMILES CC1CC2C(C(C3(C1C=CC3=O)C)O)C(=C)C(=O)O2
Standard InChIKey ZVLOPMNVFLSSAA-XEPQRQSNSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Helenalin

The herbs of Helenium microce-phalum

Biological Activity of Helenalin

Description1. Helenalin is a promising experimental cytotoxic agent that possibly points to new strategies to overcome apoptosis resistance attributable to overexpression of antiapoptotic Bcl-2 proteins. 2. Helenalin has anti-inflammatory activity, it inhibits the transcription factor NF-kappaB by directly targeting p65. 3. Helenalin is a new immunosuppressive compound suited for the treatment of deregulated and unwanted T cell-mediated immune responses. 4. Helenalin has anti-trypanosomal activity against the African Trypanosoma brucei rhodesiense and American T. cruzi. 5. Helenalin reduces Staphylococcus aureus infection in vitro and in vivo. 6. Helenalin has anticancer activity, it contributes to the induction of autophagy cell death by NF-κB p65 repression.
TargetsBcl-2/Bax | Caspase | P450 (e.g. CYP17) | NF-kB | p65

Helenalin Dilution Calculator

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Helenalin Molarity Calculator

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Preparing Stock Solutions of Helenalin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.8124 mL 19.0621 mL 38.1243 mL 76.2486 mL 95.3107 mL
5 mM 0.7625 mL 3.8124 mL 7.6249 mL 15.2497 mL 19.0621 mL
10 mM 0.3812 mL 1.9062 mL 3.8124 mL 7.6249 mL 9.5311 mL
50 mM 0.0762 mL 0.3812 mL 0.7625 mL 1.525 mL 1.9062 mL
100 mM 0.0381 mL 0.1906 mL 0.3812 mL 0.7625 mL 0.9531 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Helenalin

The anti-inflammatory sesquiterpene lactone helenalin inhibits the transcription factor NF-kappaB by directly targeting p65.[Pubmed:9837931]

J Biol Chem. 1998 Dec 11;273(50):33508-16.

The sesquiterpene lactone Helenalin is a potent anti-inflammatory drug whose molecular mechanism of action remains unclear despite numerous investigations. We have previously shown that Helenalin and other sesquiterpene lactones selectively inhibit activation of the transcription factor NF-kappaB, a central mediator of the human immune response. These drugs must target a central step in NF-kappaB pathway, since they inhibit NF-kappaB induction by four different stimuli. It has previously been reported that sesquiterpene lactones exert their effect by inhibiting degradation of IkappaB, the inhibitory subunit of NF-kappaB. These data contradicted our report that IkappaB is not detectable in Helenalin-treated, ocadaic acid-stimulated cells. Here we use confocal laser scanning microscopy to demonstrate the presence of IkappaB-released, nuclear NF-kappaB in Helenalin-treated, tumor necrosis factor-alpha stimulated cells. These data show that neither IkappaB degradation nor NF-kappaB nuclear translocation are inhibited by Helenalin. Rather, we provide evidence that Helenalin selectively alkylates the p65 subunit of NF-kappaB. This sesquiterpene lactone is the first anti-inflammatory agent shown to exert its effect by directly modifying NF-kappaB.

Helenalin reduces Staphylococcus aureus infection in vitro and in vivo.[Pubmed:17010538]

Vet Microbiol. 2007 Jan 31;119(2-4):330-8.

Staphylococcus (S.) aureus is a major udder pathogen causing bovine mastitis. Some pro-inflammatory cytokines, including tumor necrosis factor-alpha (TNF-alpha), enhance extracellular and intracellular growth of S. aureus, indicating that the inflammatory process favors S. aureus infection. Helenalin is a sesquiterpene lactone with potent anti-inflammatory properties. This study was designed to evaluate the effects of Helenalin on S. aureus infection. First, in vitro experiments were conducted. These studies revealed that proliferation of S. aureus in bovine mammary epithelial MAC-T cells treated in the presence or absence of TNF-alpha was markedly reduced in the presence of Helenalin. Secondly, in vivo effects of Helenalin were investigated. Lactating mice treated in the presence or absence of Helenalin were challenged by the intramammary route with S. aureus and the bacteria in the mammary glands were counted 12 h after infection. Significantly less numbers of bacteria were recovered from the infected glands of Helenalin-treated mice compared with untreated mice. Moreover, histological examination of mammary tissue from Helenalin-treated mice that were challenged with S. aureus indicated that Helenalin is able to significantly reduce leukocyte infiltration in the mammary gland following S. aureus inoculation. Our results show that Helenalin reduces S. aureus intracellular growth and experimental S. aureus infection. We conclude that Helenalin may be of potential interest in the treatment of S. aureus-induced mastitis in the bovine species.

NF-kappaB p65 repression by the sesquiterpene lactone, Helenalin, contributes to the induction of autophagy cell death.[Pubmed:22784363]

BMC Complement Altern Med. 2012 Jul 11;12:93.

BACKGROUND: Numerous studies have demonstrated that autophagy plays a vital role in maintaining cellular homeostasis. Interestingly, several anticancer agents were found to exert their anticancer effects by triggering autophagy. Emerging data suggest that autophagy represents a novel mechanism that can be exploited for therapeutic benefit. Pharmacologically active natural compounds such as those from marine, terrestrial plants and animals represent a promising resource for novel anticancer drugs. There are several prominent examples from the past proving the success of natural products and derivatives exhibiting anticancer activity. Helenalin, a sesquiterpene lactone has been demonstrated to have potent anti-inflammatory and antitumor activity. Albeit previous studies demonstrating Helenalin's multi modal action on cellular proliferative and apoptosis, the mechanisms underlying its action are largely unexplained. METHODS: To deduce the mechanistic action of Helenalin, cancer cells were treated with the drug at various concentrations and time intervals. Using western blot, FACS analysis, overexpression and knockdown studies, cellular signaling pathways were interrogated focusing on apoptosis and autophagy markers. RESULTS: We show here that Helenalin induces sub-G1 arrest, apoptosis, caspase cleavage and increases the levels of the autophagic markers. Suppression of caspase cleavage by the pan caspase inhibitor, Z-VAD-fmk, suppressed induction of LC3-B and Atg12 and reduced autophagic cell death, indicating caspase activity was essential for autophagic cell death induced by Helenalin. Additionally, Helenalin suppressed NF-kappaB p65 expression in a dose and time dependent manner. Exogenous overexpression of p65 was accompanied by reduced levels of cell death whereas siRNA mediated suppression led to augmented levels of caspase cleavage, autophagic cell death markers and increased cell death. CONCLUSIONS: Taken together, these results show that Helenalin mediated autophagic cell death entails inhibition of NF-kappaB p65, thus providing a promising approach for the treatment of cancers with aberrant activation of the NF-kappaB pathway.

Helenalin triggers a CD95 death receptor-independent apoptosis that is not affected by overexpression of Bcl-x(L) or Bcl-2.[Pubmed:11479221]

Cancer Res. 2001 Aug 1;61(15):5817-23.

Apoptosis is required for proper tissue homeostasis. Defects in apoptosis signaling pathways, thus, contribute to carcinogenesis and chemoresistance. A major goal in chemotherapy is, therefore, to find cytotoxic agents that restore the ability of tumor cells to undergo apoptosis. We show here that the sesquiterpene lactone Helenalin (10-50 microM) induces apoptosis in leukemia Jurkat T cells even if they lack the CD95 death receptor or overexpress the antiapoptotic proteins Bcl-x(L) or Bcl-2. Activated peripheral blood mononuclear cells, however, are not affected (10-50 microM Helenalin). Helenalin led to a time-dependent (0-24 h) cleavage of the specific caspase-3-like substrate Asp-Glu-Val-Asp-7-amino-4-trifluoromethylcoumarin as well as to the proteolytic processing of procaspase-3 and -8. Caspase activation was a necessary requirement for apoptosis because the broad-spectrum caspase inhibitor benzyloxycarbonyl-Val-Ala-Asp(OMe)-fluoromethylketone (zVAD-fmk, 50 microM) completely abrogated Helenalin-induced DNA fragmentation as well as phosphatidylserin translocation. Although the initiator caspase-8 was activated, the Helenalin-induced signaling pathway did not require the CD95 death receptor as shown using cells without or with an antibody (ZB4)-blocked CD95 receptor. Helenalin also did not induce CD95 or CD95-ligand expression. On the other hand, Helenalin was found to induce the release of cytochrome c from mitochondria that was not inhibited by the caspase inhibitor zVAD-fmk, which indicated that cytochrome c release precedes caspase activation. Cytochrome c release was accompanied by dissipation of the mitochondrial transmembrane potential (DeltaPsi(m)), which was partly inhibited by zVAD-fmk, which suggests that caspases are involved in loss of DeltaPsi(m). Most importantly, overexpression of the mitochondria protecting proteins Bcl-x(L) or Bcl-2 failed to confer resistance to Helenalin-induced apoptosis, although the data presented here suggest that Helenalin induces a mitochondria-dependent pathway. Thus, Helenalin is a promising experimental cytotoxic agent that possibly points to new strategies to overcome apoptosis resistance attributable to overexpression of antiapoptotic Bcl-2 proteins.

Description

Helenalin is an anti-inflammatory sesquiterpene lactone. Helenalin selectively inhibits transcription factor NF-κB by directly targeting p65. Helenalin has alkylating activity, targets the cysteine sulfhydryl groups in the p65 subunit of NF-κB, thereby inhibits its DNA binding.

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