Helenalin

Specifications / Handling

More Information
Product Details
Synonyms	Helenalin A; NSC 85236
Product Type	Chemical
Properties
Formula	C₁₅H₁₈O₄
MW	262.3
CAS	6754-13-8
Source/Host Chemicals	Isolated from Arnica montana.
Purity Chemicals	≥96% (HPLC)
Appearance	White to off-white solid.
Solubility	Soluble in ethanol or DMSO.
Identity	Determined by ¹H-NMR.
InChi Key	ZVLOPMNVFLSSAA-XEPQRQSNSA-N
Smiles	[H][C@@]12C=CC(=O)[C@@]1(C)[C@@H](O)[C@H]1[C@@H](C[C@H]2C)OC(=O)C1=C
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C. Working aliquots are stable for up to 3 months when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Anticancer compound.
NF-κB inhibitor.
Apoptosis inducer.
Potent anti-inflammatory agent.
Telomerase inhibitor.
Anti-trypanosomal and antiprotozoal compound
Antibiotic.
Shows anti-proliferative effects in 3T3-L1 preadipocytes.
Autophagy inducer.

Product References

Constituents of Helenium species.XIII. The structure of Helenalin and Mexicanin A: W. Herz, et al.; JACS 85, 19 (1963)
Antitumor agents. 21. A proposed mechanism for inhibition of cancer growth by tenulin and helenalin and related cyclopentenones: I.H. Hall, et al.; J. Med. Chem. 20, 333 (1977)
Inhibition of nucleic acid synthesis in P-388 lymphocytic leukemia tumor cells by helenalin and bis(helenalinyl)malonate in vivo: W.L. Williams Jr, et al.; J. Pharm. Sci. 77, 178 (1988)
Helenalin, an anti-inflammatory sesquiterpene lactone from Arnica, selectively inhibits transcription factor NF-kappaB: G. Lyss, et al.; J. Biol. Chem. 378, 951 (1997)
The anti-inflammatory sesquiterpene lactone helenalin inhibits the transcription factor NF-kappaB by directly targeting p65: G. Lyss, et al; J. Biol. Chem. 273, 33508 (1998)
Helenalin triggers a CD95 death receptor-independent apoptosis that is not affected by overexpression of Bcl-x(L) or Bcl-2: V.M. Dirsch, et al.; Cancer Res. 61, 5817 (2001)
Anti-trypanosomal activity of helenalin and some structurally related sesquiterpene lactones: T.J. Schmidt, et al.; Planta Med. 68, 750 (2002)
Induction of human leukemia HL-60 cell differentiation via a PKC/ERK pathway by helenalin, a pseudoguainolide sesquiterpene lactone: S.H. Kim, et al.; Eur. J. Pharmacol. 511, 89 (2005)
Potent inhibition of human telomerase by helenalin: P.R. Huang, et al.; Cancer Lett. 227, 169 (2005)
Novel effect of helenalin on Akt signaling and Skp2 expression in 3T3-L1 preadipocytes: C.A. Auld, et al.; BBRC 346, 314 (2006)
Helenalin reduces Staphylococcus aureus infection in vitro and in vivo: D. Boulanger, et al.; Vet. Microbiol. 119, 330 (2007)
Helenalin-mediated post-transcriptional regulation of p21(Cip1) inhibits 3T3-L1 preadipocyte proliferation: K.M. Fernandes, et al.; J. Cell Biochem. 105, 913 (2008)
Helenalin suppresses essential immune functions of activated CD4+ T cells by multiple mechanisms: C. Berges, et al.; Mol. Immunol. 46, 2892 (2009)
Helenalin bypasses Bcl-2-mediated cell death resistance by inhibiting NF-κB and promoting reactive oxygen species generation: R. Hoffmann, et al.; Biochem. Pharmacol. 82, 453 (2011)
NF-κB p65 repression by the sesquiterpene lactone, Helenalin, contributes to the induction of autophagy cell death: C.B. Lim, et al.; BMC Complement. Altern. Med. 12, 93 (2012)
Natural sesquiterpene lactones induce programmed cell death in Trypanosoma cruzi: a new therapeutic target?: V. Jimenez, et al.; Phytomedicine 21, 1411 (2014)

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