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Lepidiline A Sale

目录号 : GC66014

Lepidiline A 对HL-60细胞具有细胞毒活性,IC50值为 32.3 μM.

Lepidiline A Chemical Structure

Cas No.:596093-98-0

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10mg
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Lepidiline A shows cytotoxic activity against HL-60 cells with an IC50 of 32.3 μM.

Chemical Properties

Cas No. 596093-98-0 SDF Download SDF
分子式 C19H21ClN2 分子量 312.84
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1 mM 3.1965 mL 15.9826 mL 31.9652 mL
5 mM 0.6393 mL 3.1965 mL 6.393 mL
10 mM 0.3197 mL 1.5983 mL 3.1965 mL
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Research Update

Lepidiline A Improves the Balance of Endogenous Sex Hormones and Increases Fecundity by Targeting HSD17B1

Mol Nutr Food Res 2020 May;64(10):e1900706.PMID:32239630DOI:10.1002/mnfr.201900706.

Scope: Maca (Lepidium meyenii), a well-known plant from the Andean highlands of Peru, has been used widely as a nutritional supplement to increase sexual function and fecundity. However, the identity of its active ingredients and how they function remain unknown. Methods and results: Chemical substances in maca are identified by UPLC-Q-TOF, and the active ingredients are screened through HotMap coupled with an artificial neural network. Lepidiline A (LA), an imidazole alkaloid, is identified as the key active compound. LA affects the balance of endogenous sex hormones in mice and improves fecundity in Drosophila. Using a molecular LA probe, 17ß-hydroxysteroid dehydrogenase type 1 (HSD17B1) is revealed to be the potential target of LA using a fishing-rod strategy. It is demonstrated with experimental data that LA targets HSD17B1 to enhance the enzyme's activity and increases its bioconversion efficiency of actively formed sex hormones including estrogen to 17β-estradiol and 4-androsten-3,7-dione to testosterone, which ultimately improves reproductive activity. Conclusion: LA improves the balance of endogenous sex hormones and increases fecundity by targeting HSD17B1. This underlying mechanism of action provides a useful insight into the application of maca in the regulation of dietary nutrition and healthy fertility.

Novel Anticancer NHC*-Gold(I) Complexes Inspired by Lepidiline A

Molecules 2020 Jul 30;25(15):3474.PMID:32751607DOI:10.3390/molecules25153474.

N-Heterocyclic carbene gold(I) complexes derived from 1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene (NHC*) represent a promising class of anticancer drugs. Complexes of the type NHC*-Au-L (L = Br-, I-, C≡C-R) and [NHC*-Au-L]+ (L = NHC*, PPh3) have been synthesised. The X-ray crystal structures of all gold(I) complexes are presented; aurophilic interactions were observed in five of the complexes. The anticancer activity was assessed via MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide)-based proliferation assays against the human colon carcinoma cell line HCT-116wt and the multidrug-resistant human breast carcinoma cell line MCF-7topo. Most complexes showed good cytotoxicity with IC50 values in the low micromolar range, while excellent sub-micromolar activity was observed for 2c, 3a and 3b. Generally, the activity of the ligands studied was as follows: carbene > phosphine > alkyne > halide, with an exception for the highly active iodido derivative 2c.

Synthesis and Cytotoxicity Studies of Novel NHC*-Gold(I) Complexes Derived from Lepidiline A

Molecules 2018 Aug 14;23(8):2031.PMID:30110951DOI:10.3390/molecules23082031.

Ten novel N-heterocyclic carbene gold(I) complexes derived from Lepidiline A (1,3-dibenzyl-4,5-dimethylimidazolium chloride) are reported here with full characterisation and biological testing. (1,3-Dibenzyl-4,5-diphenylimidazol-2-ylidene)gold(I) chloride (NHC*-AuCl) (1) was modified by substituting the chloride for the following: cyanide (2), dithiocarbamates (3⁻5), p-mercaptobenzoate derivatives (12⁻14) and N-acetyl-l-cysteine derivatives (15⁻17). All complexes were synthesised in good yields of 57⁻78%. Complexes 2, 12, 13, and 14 were further characterised by X-ray crystallography. Initial evaluation of the biological activity was conducted on all ten complexes against the multidrug resistant MCF-7topo breast cancer, HCT-116wt, and p53 knockout mutant HCT-116-/- colon carcinoma cell lines. Across the three cell lines tested, mainly single-digit micromolar IC50 values were observed. Nanomolar activity was exhibited on the MCF-7topo cell line with 3 displaying an IC50 of 0.28 μM ± 0.03 μM. Complexes incorporating a Au⁻S bond resulted in higher cytotoxic activity when compared to complexes 1 and 2. Theoretical calculations, carried out at the MN15/6⁻311++G(2df,p) computational level, show that NHC* is the more favourable ligand for Au(I)-Cl when compared to PPh₃.

Imidazole alkaloids from Lepidium meyenii

J Nat Prod 2003 Aug;66(8):1101-3.PMID:12932133DOI:10.1021/np030031i.

Two new imidazole alkaloids (Lepidiline A and lepidiline B) have been isolated from a root extract of Lepidium meyenii with the common name Maca and identified as 1,3-dibenzyl-4,5-dimethylimidazolium chloride (1) and 1,3-dibenzyl-2,4,5-trimethylimidazolium chloride (2), respectively. The structures of these two new compounds were determined by spectroscopic methods, as well as single-crystal X-ray diffraction performed on compound 1.