Enmein

Names

[ Name ]:
Enmein

[Synonym ]:
(1S,4S,6S,8R,9R,12S,13S,16R)-6,9-Dihydroxy-7,7-dimethyl-17-methylene-3,10-dioxapentacyclo[14.2.1.0.0.0]nonadecane-2,18-dione
5H-5a,8-Methano-11H-cyclohepta[c]furo[3,4-e][1]benzopyran-5,6(7H)-dione, decahydro-2,13-dihydroxy-1,1-dimethyl-7-methylene-, (2S,3aS,5aS,8R,10aS,10bS,13R,13aR)-
5H-5a,8-Methano-11H-cyclohepta(c)furo(3,4-e)(1)benzopyran-5,6(7H)-dione, decahydro-2,13-dihydroxy-1,1-dimethyl-7-methylene-, (2S,3as,5as,7R,8R,10aS,10bS,13R,13aR)-

Biological Activity

[Description]:

Enmein is isolated from I. serra with immunosuppressive effect[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

[In Vitro]

Enmein shows significant inhibitory effect toward K562 with an IC50 value ranging from 3.2 μg/ml to 8.2 μg/ml[2]. Enmein (3.13-25 μg/ml; 48 hours) has inhibitory effect on lymphocytes with significant difference within concentration from 6.25 μg/ml to 25 μg/ml[1]. Enmein (5.5-22 μg/ml; 48 hours) causes the percentage of S stage cells decreased from 19% to 6%, causes the percentage of G2/M stage cells to decrease from 2% to 0.4%[1]. Cell Viability Assay[1] Cell Line: Splenic lymphocyte cells Concentration: 3.13, 6.25, 12.5, 25 μg/ml Incubation Time: 48 hours Result: Exhibited an IC50 value of 17 μg/ml in splenic lymphocytes. Cell Cycle Analysis[1] Cell Line: Splenic lymphocyte cells Concentration: 5.5 μg/ml, 11 μg/ml, 22 μg/ml Incubation Time: 48 hours Result: Caused S stage cells and G2/M stage cells decreased.

[In Vivo]

Enmein (inject to ear; 6.52-13.04 mg/kg; 5 days) inhibits the xylene-induced ear swelling and inhibits IL-2 expression[1]. Animal Model: Balb/c mice[1] Dosage: 6.52 mg/kg, 9.78 mg/kg or 13.04 mg/kg Administration: Injected to ear; 6.52 mg/kg, 9.78 mg/kg or 13.04 mg/kg; 5 days Result: Had inhibitory effect on IL-2 release in blood.

[References]

[1]. Zhang Y, et al. Distinct immunosuppressive effect by Isodon serra extracts. Int Immunopharmacol. 2005 Dec;5(13-14):1957-65. Epub 2005 Jul 13.

[2]. Jiang B, et al. Cytotoxic ent-kaurane diterpenoids from Isodon sculponeata. Planta Med. 2002 Oct;68(10):921-5.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
610.3±55.0 °C at 760 mmHg

[ Melting Point ]:
274-276℃ (Decomposition) (ethanol )

[ Molecular Formula ]:
C₂₀H₂₆O₆

[ Molecular Weight ]:
362.417

[ Flash Point ]:
220.1±25.0 °C

[ Exact Mass ]:
362.172943

[ PSA ]:
93.06000

[ LogP ]:
-0.30

[ Vapour Pressure ]:
0.0±4.0 mmHg at 25°C

[ Index of Refraction ]:
1.602

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: PB9183000

CHEMICAL NAME :: 5H-5a,8-Methano-11H-cyclohepta(c)furo(3,4-e)(1)benzop yran-5,6(7H)-dione, decahydro-2, 13-dihydroxy-1,1-dimethyl-7-methylene-, (2S,3as,5as,7R,8R,10aS,10bS,13R,13aR)-

CAS REGISTRY NUMBER :: 3776-39-4

BEILSTEIN REFERENCE NO. :: 0047118

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C20-H26-O6

MOLECULAR WEIGHT :: 362.46

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 145 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JAJAAA Journal of Antibiotics, Series A. (Tokyo, Japan) V.6-20, 1953-67. For publisher information, see JANTAJ. Volume(issue)/page/year: 16,132,1963

Safety Information

[ Hazard Codes ]:
Xi

Precursor & DownStream

Precursor

DownStream

Related Compounds

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