Senegenin

Names

[ Name ]:
Senegenin

[Synonym ]:
Tennifolsaeure
(2S,3R,4S,4aR,6aR,8aS,12aS,13S,14aR,14bR)-13-(Chloromethyl)-2,3-dihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4,4a,5,6,6a,7,8,9,10,11,12,12a,13,14,14a,14b-octadecahydro-4,8a(1H)-picenedicarboxylic acid
13-(Chloromethyl)-2,3-dihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4,4a,5,6,6a,7,8,9,10,11,12,12a,13,14,14a,14b-octadecahydro-4,8a(1H)-picenedicarboxylic acid
4,8a(1H)-Picenedicarboxylic acid, 13-(chloromethyl)-2,3,4,4a,5,6,6a,7,8,9,10,11,12,12a,13,14,14a,14b-octadecahydro-2,3-dihydroxy-4,6a,11,11,14b-pentamethyl-
12-(Chloromethyl)-2,3-dihydroxy-27-norolean-13-ene-23,28-dioic acid,Tenuigenin
Senegenin
tenuifolic acid
(2b,3b,4a,12a)-12-(Chloromethyl)-2,3-dihydroxy-27-norolean-13-ene-23,28-dioic acid
4,8a(1H)-Picenedicarboxylic acid, 13-(chloromethyl)-2,3,4,4a,5,6,6a,7,8,9,10,11,12,12a,13,14,14a,14b-octadecahydro-2,3-dihydroxy-4,6a,11,11,14b-pentamethyl-, (2S,3R,4S,4aR,6aR,8aS,12aS,13S,14aR,14bR)-
Tenuifolsaeure
(2S,3R,4S,4aR,6aR,8aS,12aS,13S,14aR,14bR)-13-(Chloromethyl)-2,3-dihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4,4a,5,6,6a,7,8,9,10,11,12,12a,13,14,14a,14b-octadecahydropicene-4,8a(1H)-dicarboxylic acid
Senegin

Biological Activity

[Description]:

Tenuigenin is a major active component isolated from the root of the Chinese herb Polygala tenuifolia. Tenuigenin protects against S.aureus-induced pneumonia by inhibiting NF-κB activation. Tenuigenin has anti-inflammatory effect[1].

[Related Catalog]:

Research Areas >> Infection

Research Areas >> Inflammation/Immunology

[Target]

NF-κB

[In Vivo]

Tenuigenin (2, 4, 8 mg/kg) significantly attenuates S.aureus-induced lung histopathological changes. Tenuigenin also inhibits lung wet/dry (W/D) ratio, and inflammatory cytokines TNF-α and IL-1β production in Male BALB/c mice[1].

[References]

[1]. Yu B, et al. Protective effects of tenuigenin on Staphylococcus aureus-induced pneumonia in mice. Microb Pathog. 2017 Sep;110:385-389.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
674.1±55.0 °C at 760 mmHg

[ Melting Point ]:
290-292ºC

[ Molecular Formula ]:
C₃₀H₄₅ClO₆

[ Molecular Weight ]:
537.128

[ Flash Point ]:
361.5±31.5 °C

[ Exact Mass ]:
536.290466

[ PSA ]:
115.06000

[ LogP ]:
6.39

[ Vapour Pressure ]:
0.0±4.7 mmHg at 25°C

[ Index of Refraction ]:
1.591

[ Storage condition ]:
2-8C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RC8815000

CHEMICAL NAME :: 27-Noro-13-ene-23,28-dioic acid, 12-(chloromethyl)-2-beta,3-beta-dihydroxy-

CAS REGISTRY NUMBER :: 2469-34-3

BEILSTEIN REFERENCE NO. :: 2714357

LAST UPDATED :: 199612

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C30-H45-Cl-O6

MOLECULAR WEIGHT :: 537.20

WISWESSER LINE NOTATION :: L F6 E6 B666 EU- NTJ A1 D1G H1 H1 KVQ O1 SVQ S1 TQ UQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 gm/kg

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

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1289,1935

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3 mg/kg

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

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(2),259,1982

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 30 mg/kg

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

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1289,1935

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 45 mg/kg

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

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1289,1935

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
RC8815000