| Identification | Back Directory | [Name]
Hederagenin | [CAS]
465-99-6 | [Synonyms]
Hederidin
NSC 24954
Rangefinder
Hederogenin
HEDERAGENIN
hederagenol
Hederagenine
Kalosapogenin
Vaccaric acid
MELANTHIGENIN
CAULOSAPOGENIN
HEDERAGENIN(RG)
astrantiagenine
hederagenicacid
Hederagenin, >=98%
CAULOSAPOGENIN hplc
Hederagenin 465-99-6
HEDERAGENIN WITH HPLC
3,23-Dihydroxyolean-12-en-28-acid
3,23-DIHYDROXYOLEAN-12-EN-28 OIC ACID
3-beta,23-dihydroxy-olean-12-en-28-oicaci
(4R)-3β,23-Dihydroxyolean-12-en-28-oic acid
(3b,4a)-3,23-Dihydroxyolean-12-en-28-oic acid
(3β,4α) -3,23-Dihydroxy-olean-12-en- 28-oic acid
Olean-12-en-28-oicacid, 3,23-dihydroxy-, (3b,4a)-
Hederagenin, 98%, from Hedera nepalensisvar.sinensis
(3-beta,4-alpha)-3,23-dihydroxyolean-12-en-28-oicacid
3,23-dihydroxy-,(3-beta,4-alpha)-olean-12-en-28-oicaci
(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-9-methylol-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
(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-carboxylicaci
(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 | [EINECS(EC#)]
207-369-9 | [Molecular Formula]
C30H48O4 | [MDL Number]
MFCD00017385 | [MOL File]
465-99-6.mol | [Molecular Weight]
472.7 |
| Chemical Properties | Back Directory | [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. ]
2-8°C | [solubility ]
methanol: soluble1mg/mL | [form ]
Solid | [pka]
4.63±0.70(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
22 | [Safety Statements ]
22-45-24/25 | [WGK Germany ]
3 | [HS Code ]
29181990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Description]
Hederagenin is a triterpene saponin that has been found in P. eximia with diverse biological activities.1,2,3,4,5 It increases production of reactive oxygen species (ROS), reduces colony formation, and induces apoptosis in cisplatin-resistant head and neck carcinoma (HNC) cells.2 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.3 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.4 It also induces autophagy and inhibits oligomerization of α-synuclein in a mouse model of Parkinson''s disease induced by MPTP.5 | [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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