2,4-Pentadienoic acid,5-phenyl-,(2S,3aR,3bS,3cS,4aR,5S,5aS,8aR,8bR,9R,10R,10aS)-3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-(hydroxymethyl)-7,9-dimethyl-10a-(1-methylethenyl)-6-oxo-2-phen

Names

[ Name ]:
2,4-Pentadienoic acid,5-phenyl-,(2S,3aR,3bS,3cS,4aR,5S,5aS,8aR,8bR,9R,10R,10aS)-3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-(hydroxymethyl)-7,9-dimethyl-10a-(1-methylethenyl)-6-oxo-2-phen

[Synonym ]:
meserein
12BETA-[(E,E)-5-PHENYL-2,4-PENTADIENOYLOXY]DAPHNETOXIN
MFCD00135953

Biological Activity

[Description]:

Mezerein is a PKC activator that exhibits antileukemic properties. Mezerein inhibits the growth of yeast expressing PKC alpha (IC50=1190 nM), PKC beta1 (IC50=908 nM), and PKC delta (IC50=141 nM) but not of yeast expressing PKC[1][2].

[Related Catalog]:

Signaling Pathways >> Epigenetics >> PKC

Research Areas >> Cancer

Signaling Pathways >> TGF-beta/Smad >> PKC

[In Vitro]

Mezerein is an antileukemic principle isolated from Daphne mezereum L[2]. Mezerein (50 ng/mL; 72 hours) potently inhibit tumorigenic murine macrophage cell line M5076 cellular proliferation[3]. Cell Proliferation Assay[3] Cell Line: M5076 cells Concentration: 50 ng/mL Incubation Time: 72 hours Result: Inhibited cellular proliferation (by greater than 90%).

[In Vivo]

Mezerein exhibits antileukemic activity against the P-388 lymphocytic leukemia in mice. Mezerein (50 μg/kg) shows significant inhibitory activity against the P-388 and L-1210 leukemias in mice[2].

[References]

[1]. L Saraiva, et al. Differential activation by daphnetoxin and mezerein of PKC-isotypes alpha, beta I, delta and zeta. Planta Med. 2001 Dec;67(9):787-90.

[2]. S M Kupchan,et al.Mezerein: antileukemic principle isolated from Daphne mezereum L. Science. 1975 Feb 21;187(4177):652-3.

[3]. N T Goode, et al. Protein kinase C-induced stimulation or inhibition of cellular proliferation in a murine macrophage tumor cell line. Cancer Res. 1990 Mar 15;50(6):1828-33.

Chemical & Physical Properties

[ Density]:
1.43 g/cm3

[ Melting Point ]:
258-262ºC

[ Molecular Formula ]:
C₃₈H₃₈O₁₀

[ Molecular Weight ]:
654.70200

[ Exact Mass ]:
654.24600

[ PSA ]:
144.28000

[ LogP ]:
3.12420

[ Index of Refraction ]:
1.68

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HB5425500

CHEMICAL NAME :: Daphnetoxin, 12-((1-oxo-5-phenyl-2,4-pentadienyl)oxy)-, (12-beta(E,E))-

CAS REGISTRY NUMBER :: 34807-41-5

LAST UPDATED :: 199612

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C38-H38-O10

MOLECULAR WEIGHT :: 654.76

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3560 ug/kg/20W-I

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - primary irritation (after topical exposure) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other Enzymes

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 18 mg/kg/20W-I

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - primary irritation (after topical exposure) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other Enzymes

TYPE OF TEST :: Unscheduled DNA synthesis

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 340 nmol/kg

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 43,4126,1983 *** REVIEWS *** TOXICOLOGY REVIEW BLFSBY Basic Life Sciences. (Plenum Pub. Corp., 223 Spring St., New York, NY 10003) V.1- 1973- Volume(issue)/page/year: 24,253,1983

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H317

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S22;S24/25

[ RIDADR ]:
UN 2811

[ RTECS ]:
HB5425500

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Articles

Models of acute inflammation in the ear.

Methods Mol. Biol. 225 , 129-37, (2003)

Gateway synthesis of daphnane congeners and their protein kinase C affinities and cell-growth activities.

Nature Chemistry 3(8) , 615-9, (2011)

The daphnane diterpene orthoesters constitute a structurally fascinating family of natural products that exhibit a remarkable range of potent biological activities. Although partial activity informati...

Analysis of daphnane orthoesters in poisonous Australian pimelea species by liquid chromatography-tandem mass spectrometry.

J. Agric. Food Chem. 58(12) , 7482-7, (2010)

Cattle grazing in arid rangelands of Australia suffer periodic extensive and serious poisoning by the plant species Pimelea trichostachya, P. simplex, and P. elongata. Pimelea poisoning (also known as...

Related Compounds

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