ChemicalBook Product Catalog Natural Products Terpenes Hederagenin

Hederagenin

Product NameHederagenin
CAS465-99-6
MFC30H48O4
MW472.71
EINECS207-369-9
MOL File465-99-6.mol

Chemical Properties

Melting point	332-334°
alpha	D20 +81° (c = 0.7 in pyridine)
Boiling point	493.44°C (rough estimate)
Density	0.9871 (rough estimate)
refractive index	1.4800 (estimate)
storage temp.	Sealed in dry,2-8°C
solubility	methanol: soluble1mg/mL
pka	4.63±0.70(Predicted)
form	Solid
color	White to Off-White
λmax	405nm(H2SO4)(lit.)
Merck	14,4624
InChIKey	PGOYMURMZNDHNS-MYPRUECHSA-N
SMILES	C[C@@]12CC[C@]3(CCC(C)(C)C[C@@]3([H])C1=CC[C@]1([H])[C@]3(CC[C@H](O)[C@@](C)(CO)[C@]3([H])CC[C@@]21C)C)C(=O)O \|&1:1,4,11,16,18,21,23,27,31,r\|
LogP	7.410 (est)

Safety Information

Hazard Codes	Xi
Risk Statements	22
Safety Statements	22-45-24/25
WGK Germany	3
HS Code	29181990

MSDS

Provider	Language
Hederagenin	English

Usage And Synthesis

Description

Hederagenin is a triterpene saponin that has been found in P. eximia with diverse biological activities. It increases production of reactive oxygen species (ROS), reduces colony formation, and induces apoptosis in cisplatin-resistant head and neck carcinoma (HNC) cells. In vivo, hederagenin (50, 100, and 200 mg/kg) suppresses tumor growth in a cisplatin-resistant HNC mouse xenograft model. It reduces aortic atherosclerotic lesion area, serum cholesterol and LDL levels, and inducible nitric oxide synthase (iNOS) protein levels in a rat model of atherosclerosis. Hederagenin (50 mg/kg) reduces ethanol-induced production of TNF-α, IL-6, and COX-2, alcohol dehydrogenase 2 (ALDH2) mRNA expression, and liver damage in a rat model of alcohol-induced hepatotoxicity. It also induces autophagy and inhibits oligomerization of α-synuclein in a mouse model of Parkinson''s disease induced by MPTP.

Chemical Properties

White Solid

Uses

Triterpenoid which can inhibit the proliferation of leukemia HL-60 cells.

Definition

ChEBI: A sapogenin that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 3 and 23 (the 3beta stereoisomer).

in vivo

Hederagenin (25 mg/kg; po; 11 d) alone did not affect tumor growth in NCI-H1299 xenograft mice. However, it has a synergistic effect with Cisplatin (1 mg/kg) to inhibit tumor growth^[4].
Hederagenin (50 mg/kg; po; once daily for 21 days) exerts anti-inflammatory and anti-apoptotic activities and reduces liver damage induced by 25% ethanol in mice^[5].

References

[1] LALITH JAYASINGHE . Hederagenin glycosides from Pometia eximia[J]. Phytochemistry, 1995, 40 3: Pages 891-897. DOI: 10.1016/0031-9422(95)00360-j
[2] EUN HYE KIM. Hederagenin Induces Apoptosis in Cisplatin-Resistant Head and Neck Cancer Cells by Inhibiting the Nrf2-ARE Antioxidant Pathway.[J]. Oxidative Medicine and Cellular Longevity, 2017: 5498908. DOI: 10.1155/2017/5498908
[3] SU-HONG LU. Experimental Study of Antiatherosclerosis Effects with Hederagenin in Rats[J]. Evidence-based Complementary and Alternative Medicine, 2015, 35 1. DOI: 10.1155/2015/456354
[4] GYEONG-JI KIM. Hederagenin Supplementation Alleviates the Pro-Inflammatory and Apoptotic Response to Alcohol in Rats[J]. Nutrients, 2017. DOI: 10.3390/nu9010041
[5] AN-GUO WU . Hederagenin and α-hederin promote degradation of proteins in neurodegenerative diseases and improve motor deficits in MPTP-mice[J]. Pharmacological research, 2017, 115: Pages 25-44. DOI: 10.1016/j.phrs.2016.11.002

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