Helenalin

Modify Date: 2024-01-06 13:37:55

Helenalin Structure
Helenalin structure
 Common Name Helenalin
CAS Number 6754-13-8 Molecular Weight 262.30100
Density 1.25g/cm3 Boiling Point 473ºC at 760 mmHg
Molecular Formula C15H18O4 Melting Point 167-168ºC
MSDS N/A Flash Point 179.9ºC

 Use of Helenalin


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[1][2].

 Names

Name helenalin
Synonym More Synonyms

 Helenalin Biological Activity

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[1][2].
Related Catalog
In Vitro Helenalin (10 μM; 20-120 minutes) causes complete inhibition of NF-κB DNA binding after 80 minutes[1]. The anti-inflammatory, anti-carcinogenic phytochemical, Helenalin is a potent inhibitor of periodic Skp2 accumulation, an F-box protein mediating SCF E3 ligase ubiquitylation and degradation of both CKIs during S phase progression[3]. Western Blot Analysis[1] Cell Line: Jurkat T cells Concentration: 10 μM Incubation Time: 20-120 minutes Result: Caused complete inhibition of NF-κB DNA binding after 80 minutes.
In Vivo Helenalin (25 mg/kg; i.p.; 6 to 12 hours) administers to immature male ICR mice caused a rapid decrease in hepatic glutathione levels[2]. Animal Model: Immature male ICR mice[2] Dosage: 25 mg/kg Administration: i.p.; 6 to 12 hours Result: Caused a rapid decrease in hepatic glutathione levels.
References

[1]. Merrill JC, et al. Role of glutathione in the toxicity of the sesquiterpene lactones hymenoxon and helenalin. J Toxicol Environ Health. 1988;23(2):159-69.

[2]. Lyss G, et al. The anti-inflammatory sesquiterpene lactone helenalin inhibits the transcription factor NF-kappaB by directly targeting p65. J Biol Chem. 1998 Dec 11;273(50):33508-16.

[3]. Fernandes KM, et al. Helenalin-mediated post-transcriptional regulation of p21(Cip1) inhibits 3T3-L1 preadipocyteproliferation. J Cell Biochem. 2008 Oct 15;105(3):913-21.

 Chemical & Physical Properties

Density 1.25g/cm3
Boiling Point 473ºC at 760 mmHg
Melting Point 167-168ºC
Molecular Formula C15H18O4
Molecular Weight 262.30100
Flash Point 179.9ºC
Exact Mass 262.12100
PSA 63.60000
LogP 1.24630
Index of Refraction 1.565

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
BD9630000
CHEMICAL NAME :
Ambrosa-2,11(13)-dien-12-oic acid, 6-alpha,8-beta-dihydroxy-4-oxo-, 12,8-lactone
CAS REGISTRY NUMBER :
6754-13-8
BEILSTEIN REFERENCE NO. :
0028081
LAST UPDATED :
199712
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C15-H18-O4
MOLECULAR WEIGHT :
262.33
WISWESSER LINE NOTATION :
T C575 DYVO MV KUTJ A1 BQ DU1 I1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
125 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - food intake (animal) Gastrointestinal - peritonitis
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
90 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
85 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - domestic
DOSE/DURATION :
100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
45 mg/kg/3D-I
TOXIC EFFECTS :
Liver - changes in liver weight Endocrine - changes in spleen weight Endocrine - changes in thymus weight
TYPE OF TEST :
DNA inhibition

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Rodent - hamster Ovary
DOSE/DURATION :
780 ppb
REFERENCE :
BSECBU Biochemical Systematics and Ecology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.2- 1974- Volume(issue)/page/year: 13,365,1985

 Safety Information

RIDADR UN 2811
Packaging Group III
Hazard Class 6.1(b)

 Synonyms

dl-Mexicanin I
Helenalin A
HELENALIN
PF 56
(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
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