HELENALIN Chemical Properties

Melting point:

167-168°

alpha 

D25 -102.8° (c = 3.64 in 95% ethanol)

Boiling point:

325.55°C (rough estimate)

Density 

1.0772 (rough estimate)

refractive index 

1.4300 (estimate)

storage temp. 

-20°

solubility 

Soluble in DMSO (up to 20 mg/ml) or in Ethanol (up to 10 mg/ml).

form 

White to off-white solid.

pka

13.29±0.60(Predicted)

color 

White

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.

LogP

0.870

Safety Information

RIDADR 

2811

HazardClass 

6.1(b)

PackingGroup 

III

Hazardous Substances Data

6754-13-8(Hazardous Substances Data)

Toxicity

LD50 in mice, rats (mg/kg): 150, 125 orally (Witzel)

HELENALIN Usage And Synthesis

Description

Helenalin (6754-13-8) is a novel sesquiterpene lactone which inhibits NFκB1?and displays potent anti-inflammatory activity2. It suppresses essential immune functions of activated CD4+ T cells by multiple mechanisms.3 Helenalin also inhibits telomerase and this activity may be partially responsible for its anti-tumor effects.4

Uses

Helenalin is a highly toxic compound, with hepatic and lymphatic tissues particularly vulnerable to its effects. It is believed to be responsible for the toxicity and skin irritation associated with Arnica. If enough of the plant is ingested, the helenalin produces severe gastroenteritis and internal bleeding of the digestive tract.

Definition

ChEBI: 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.

in vivo

storage

+4°C

References

[1] G LYSS. The anti-inflammatory sesquiterpene lactone helenalin inhibits the transcription factor NF-kappaB by directly targeting p65.[J]. The Journal of Biological Chemistry, 1998, 273 50: 33508-33516. DOI:10.1074/jbc.273.50.33508
[2] G LYSS. Helenalin, an anti-inflammatory sesquiterpene lactone from Arnica, selectively inhibits transcription factor NF-kappaB.[J]. Biological Chemistry, 1997, 378 9: 951-961. DOI:10.1515/bchm.1997.378.9.951
[3] CARSTEN BERGES. Helenalin suppresses essential immune functions of activated CD4+ T cells by multiple mechanisms[J]. Molecular immunology, 2009, 46 15: Pages 2892-2901. DOI:10.1016/j.molimm.2009.07.004
[4] PEI-RONG HUANG  Tzu C V W  Yuan Ming Yeh. Potent inhibition of human telomerase by helenalin[J]. Cancer letters, 2005, 227 2: Pages 169-174. DOI:10.1016/j.canlet.2004.11.045

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