| Identification | Back Directory | [Name]
SENEGENIN | [CAS]
2469-34-3 | [Synonyms]
SENEGIN
SENEGENIN
Tenuigenin
Tenuifgenin
Tenuifolic acid
Senegenin, >=98%
12-(Chloromethyl)-2,3-dihydroxy-27-norolean-13-ene-23,28-dioic acid
12α-Chloromethyl-2β,3β-dihydroxy-27-norolean-1-ene-23,28-dioic acid
28-dioicacid,12-(chloromethyl)-2-beta,3-beta-dihydroxy-27-noro-13-ene-2
12α-(Chloromethyl)-2β,3β-dihydroxy-27-nor-5α-olean-13-ene-23,28-dioic acid
27-Norolean-13-ene-23,28-dioicacid, 12-(chloromethyl)-2,3-dihydroxy-, (2β,3β,4α,12α)-
(2beta,3beta,4alpha,12alpha)-12-(Chloromethyl)-2,3-dihydroxy-27-norolean-13-ene-23,28-dioic acid
13-(chloromethyl)-2,3-dihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1H-picene-4,8a-dicarboxylic acid | [Molecular Formula]
C30H45ClO6 | [MDL Number]
MFCD00466906 | [MOL File]
2469-34-3.mol | [Molecular Weight]
537.13 |
| Chemical Properties | Back Directory | [Melting point ]
290-292℃ | [alpha ]
D +19° (c = 0.70 in ethanol) | [Boiling point ]
674.1±55.0 °C(Predicted) | [density ]
1.28 | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble10mg/mL, clear | [form ]
powder | [pka]
4.27±0.70(Predicted) | [color ]
white to beige | [InChIKey]
CWHJIJJSDGEHNS-JEKQWPLRNA-N | [SMILES]
C[C@]12C[C@H](O)[C@H](O)[C@@](C)(C(=O)O)[C@]1([H])CC[C@]1(C3CC[C@]4(CCC(C)(C)C[C@@]4([H])C=3[C@@H](CCl)C[C@]21[H])C(=O)O)C |&1:1,3,5,7,12,16,20,27,30,34,r| |
| Safety Data | Back Directory | [WGK Germany ]
3 | [RTECS ]
RC8815000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral | [Toxicity]
LD50 intraperitoneal in mouse: 3mg/kg |
| Hazard Information | Back Directory | [Description]
Tenuigenin is a triterpenoid sapogenin that has been found in P. tenuifolia and has diverse biological activities, including antioxidant, anti-inflammatory, and neuroprotective properties.1,2,3 It inhibits IL-1β and reactive oxygen species (ROS) production from LPS-induced mouse BV2 microglia at a concentration of 4 μM.2 Tenuigenin (25 mg/kg per day) decreases NOD-, LRR-, and pyrin domain-containing protein 3 (NLRP3) inflammasome activation and prevents dopaminergic neuronal degeneration in the mouse substantia nigra pars compacta in an MPTP-induced model of Parkinson''s disease. Tenuigenin (2 mg/kg) also reduces increases in lung edema and the levels of IL-1β and TNF-α in bronchoalveolar lavage fluid (BALF) in a mouse model of intranasal S. aureus-induced pneumonia.3 | [Chemical Properties]
White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Polygala tenuifolia. | [Uses]
Tenuifgenin is a Chinese herbal extract with anti-oxidative and anti-inflammatory effects involving toxin induced cell models of Parkinson’s disease. | [Definition]
ChEBI: Senegenin is a 12alpha-hydroxy steroid. | [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]. | [IC 50]
NF-κB | [References]
[1] J. J. DUGAN A S P Mayo. TERPENOIDS: V. SENEGENIN: FUNCTIONAL GROUPS AND PART STRUCTURE[J]. Canadian Journal of Chemistry, 1964, 143 1: 491-501. DOI: 10.1139/v64-073
[2] ZHENG FAN. Tenuigenin protects dopaminergic neurons from inflammation via suppressing NLRP3 inflammasome activation in microglia.[J]. Journal of Neuroinflammation, 2017: 256. DOI: 10.1186/s12974-017-1036-x
[3] BIN YU . Protective effects of tenuigenin on Staphylococcus aureus-induced pneumonia in mice[J]. Microbial pathogenesis, 2017, 110: Pages 385-389. DOI: 10.1016/j.micpath.2017.07.023 |
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