Hederagenin

Modify Date: 2024-01-02 18:08:57

Hederagenin Structure
Hederagenin structure
 Common Name Hederagenin
CAS Number 465-99-6 Molecular Weight 472.700
Density 1.1±0.1 g/cm3 Boiling Point 589.4±50.0 °C at 760 mmHg
Molecular Formula C30H48O4 Melting Point 332 - 334ºC
MSDS N/A Flash Point 324.3±26.6 °C

 Use of Hederagenin


Hederagenin is a triterpenoid saponin. It can inhibit LPS-stimulated expression of iNOS, COX-2, and NF-κBHederagenin can Exhibits multiple pharmacological activities in the treatment of hyperlipidemia, antilipid peroxidation, antiplatelet aggregation, liver protection, antidepression, anti-inflammation.[1]In vitro:1) Hederagenin can correct the imbalance of endothelial function by inhibiting the release of large amounts of iNOS and increasing eNOS contents and inhibits the IKKβ/NF-κB signaling pathway to reduce the release of IL-6, IFN-γ, TNF-α, and other inflammatory factors. [1]2) The EC50 of hederagenin is 39 ± 6 μM in A549 cancer cell line, but it's inactive for DLD-1 cells. [2]3) Hederagenin inhibited LPS-induced production of NO, PGE2and cytokines in cells.[3]4) Hederagenin had an anti-edema effect on the CA-induced mouse hind paw edema assay. [3]5) Hederagenin inhibited the CA-induced increase in skin thicknesses. [3]In vivo: The rats in the hederagenin group were administered hederagenin at 20 mg/kg/d via gavage.(More details please refer to the protocol below). In AS rat models induced by a high-lipid diet plus VD3, hederagenin can effectively reduce serum lipid, ALT, and AST levels, in addition to improving liver function, relieving high blood coagulation, and slowing blood flow and stasis by improving blood rheology. [1]

 Names

Name (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonym More Synonyms

 Hederagenin Biological Activity

Description Hederagenin is a triterpenoid saponin. It can inhibit LPS-stimulated expression of iNOS, COX-2, and NF-κBHederagenin can Exhibits multiple pharmacological activities in the treatment of hyperlipidemia, antilipid peroxidation, antiplatelet aggregation, liver protection, antidepression, anti-inflammation.[1]In vitro:1) Hederagenin can correct the imbalance of endothelial function by inhibiting the release of large amounts of iNOS and increasing eNOS contents and inhibits the IKKβ/NF-κB signaling pathway to reduce the release of IL-6, IFN-γ, TNF-α, and other inflammatory factors. [1]2) The EC50 of hederagenin is 39 ± 6 μM in A549 cancer cell line, but it's inactive for DLD-1 cells. [2]3) Hederagenin inhibited LPS-induced production of NO, PGE2and cytokines in cells.[3]4) Hederagenin had an anti-edema effect on the CA-induced mouse hind paw edema assay. [3]5) Hederagenin inhibited the CA-induced increase in skin thicknesses. [3]In vivo: The rats in the hederagenin group were administered hederagenin at 20 mg/kg/d via gavage.(More details please refer to the protocol below). In AS rat models induced by a high-lipid diet plus VD3, hederagenin can effectively reduce serum lipid, ALT, and AST levels, in addition to improving liver function, relieving high blood coagulation, and slowing blood flow and stasis by improving blood rheology. [1]
Related Catalog
References

[1]. Su-Hong Lu et al. Experimental Study of Antiatherosclerosis Effects with Hederagenin in Rats. Evid Based Complement Alternat Med, 2015, Oct 19

[2]. Diego Rodríguez-Hernández et al. Hederagenin as a triterpene template for the development of new antitumor compounds. Eur J Med Chem, 2015 Nov 13, 105:57-62

[3]. Chul Won Lee et al. Hederagenin, a major component of Clematis mandshurica Ruprecht root, attenuates inflammatory responses in RAW 264.7 cells and in mice. Int Immunopharmacol, 2015 Dec, 29(2):528-37.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 589.4±50.0 °C at 760 mmHg
Melting Point 332 - 334ºC
Molecular Formula C30H48O4
Molecular Weight 472.700
Flash Point 324.3±26.6 °C
Exact Mass 472.355255
PSA 77.76000
LogP 7.41
Vapour Pressure 0.0±3.8 mmHg at 25°C
Index of Refraction 1.569

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RJ8948000
CHEMICAL NAME :
Olean-12-en-28-oic acid, 3,23-dihydroxy-, (3-beta,4-alpha)-
CAS REGISTRY NUMBER :
465-99-6
LAST UPDATED :
199806
DATA ITEMS CITED :
1

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 :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YAHOA3 Yakhak Hoe Chi. Journal of the Pharmaceutical Society. (Taehan Yakkakhoe, c/o College of Pharmacy, Seoul National Univ., Seoul 151, S. Korea) V.1- 1956(?)- Volume(issue)/page/year: 39,137,1995

 Safety Information

Hazard Codes Xi: Irritant;
Risk Phrases R22
Safety Phrases 22-45

 Synthetic Route

 Synonyms

Olean-12-en-28-oic acid, 3,23-dihydroxy-, (3β)-
(3beta,4alpha)-3,23-Dihydroxyolean-12-en-28-oic acid
(4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-10-Hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-4a(2H)-picenecarboxylic acid
Hederagenol
Astrantiagenin E
3,23-dihydroxyolean-12-en-28-oic acid
Caulosapogenin
Hederagenic acid
Hederagenin
EINECS 207-369-9
Melanthigenin
3,23-Dihydroxyolean-12-en-28-acid
(3b,4a)-3,23-Dihydroxyolean-12-en-28-oic Acid
23-hydroxyoleanolic acid
(3β)-3,23-Dihydroxyolean-12-en-28-oic acid
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