lenticin
lenticin Basic information
- Product Name:
- lenticin
- Synonyms:
-
- lenticin
- N,N,N-Trimethyl-1-carboxylato-2-(1H-indole-3-yl)ethanaminium
- α-Carboxylato-N,N,N-trimethyl-1H-indole-3-ethan-1-aminium
- tryptophan betaine
- (1-Carboxy-2-indol-3-ylethyl)trimethylammonium hydroxide inner salt
- Glyyunnanenine
- Lenticine
- L-Hypaphorine
- CAS:
- 487-58-1
- MF:
- C14H18N2O2
- MW:
- 246.30492
- Mol File:
- 487-58-1.mol
lenticin Chemical Properties
- Melting point:
- 255℃ (decomposition)
- alpha
- D27 +113° (c = 0.52)
- storage temp.
- -20°C
- solubility
- DMF: Slightly soluble; DMSO: Slightly soluble; Ethanol: Slightly soluble; PBS (pH 7.2): 5 mg/ml
- form
- A solid
- color
- White to off-white
- Stability:
- Hygroscopic
lenticin Usage And Synthesis
Chemical Properties
White crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents.
Uses
Hypaphorine is an indole alkaloid isolated from Caragana korshinskii. Hypaphorine has neurological and glucose-lowering effects. Hypaphorine prevents Lipopolysaccharides (LPS) (HY-D1056)-mediated acute lung injury (ALI) and proinflammatory response via inactivating the p38/JNK signaling pathway by upregulating DUSP1[1][2][3][4].
Definition
ChEBI: An amino acid betaine obtaine by exhaustive methylation of the alpha-amino group of L-tryptophan with concomitant deprotonation of the carboxy group.
in vivo
Hypaphorine (10 mg/kg; i.p.; 2 hours after the LPS injection) relieves LPS induced acute lung injury (ALI) in rats with anti-inflammatory effects[2].
Hypaphorine (50 mg/kg; i.p.; once) has antihyperglycemic activity[4].
| Animal Model: | Male albino rats of Wistar/Sprague-Dawley strain (8-10 weeks, 160 g) made diabetic by intraperitoneal injection of Streptozotocin (HY-13753)[4] |
| Dosage: | 50 mg/kg |
| Administration: | Intraperitoneal injection (i.p.); once |
| Result: | Showed significant anti-hyperglycemic activity (27.8% at 5 h and 20.4% at 24 h). |
| Animal Model: | Male Sprague-Dawley rats (200-220 g) treated with LPS[2] |
| Dosage: | 10 mg/kg |
| Administration: | Intraperitoneal injection (i.p.); 2 hours after the LPS injection |
| Result: | Alleviated the histological changes in lung tissues induced by LPS, including severe inflammatory cell infiltration, thickened alveolar walls, obvious diffuse edema, narrowed alveolar space, strengthened interstitial congestion, serious pathological damage and higher scores. Reduced BALF cells and neutrophils increased by LPS. Attenuated the wet/dry weight ratio, capillary permeability and d myeloperoxidase (MPO) activity facilitated by LPS. |
References
[1] Keller BO, et al. Hypaphorine is present in human milk in association with consumption of legumes. J Agric Food Chem. 2013 Aug 7;61(31):7654-60. DOI:10.1021/jf401758f
[2] Ding YH, et al. Hypaphorine exerts anti-inflammatory effects in sepsis induced acute lung injury via modulating DUSP1/p38/JNK pathway. Kaohsiung J Med Sci. 2021 Oct;37(10):883-893. DOI:10.1002/kjm2.12418
[3] Ditengou FA, et al. Hypaphorine from the ectomycorrhizal fungus Pisolithus tinctorius counteracts activities of indole-3-acetic acid and ethylene but not synthetic auxins in eucalypt seedlings. Mol Plant Microbe Interact. 2000 Feb;13(2):151-8. DOI:10.1094/MPMI.2000.13.2.151
[4] Chand K, et al. Major alkaloidal constituent from Impatiens niamniamensis seeds as antihyperglycemic agent. Med Chem Res 20, 1505–1508 (2011).
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