Lycoramine

CAS# 21133-52-8

Lycoramine

Catalog No. BCN2866----Order now to get a substantial discount!

Product Name & Size Price Stock
Lycoramine: 5mg $69 In Stock
Lycoramine: 10mg Please Inquire In Stock
Lycoramine: 20mg Please Inquire Please Inquire
Lycoramine: 50mg Please Inquire Please Inquire
Lycoramine: 100mg Please Inquire Please Inquire
Lycoramine: 200mg Please Inquire Please Inquire
Lycoramine: 500mg Please Inquire Please Inquire
Lycoramine: 1000mg Please Inquire Please Inquire

Quality Control of Lycoramine

Number of papers citing our products

Chemical structure

Lycoramine

3D structure

Chemical Properties of Lycoramine

Cas No. 21133-52-8 SDF Download SDF
PubChem ID 443723 Appearance Cryst.
Formula C17H23NO3 M.Wt 289.4
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Lycoramin;Dihydrogalanthamine;1,2-Dihydrogalanthamine
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1R,12S,14S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9-trien-14-ol
SMILES CN1CCC23CCC(CC2OC4=C(C=CC(=C34)C1)OC)O
Standard InChIKey GJRMHIXYLGOZSE-JDFRZJQESA-N
Standard InChI InChI=1S/C17H23NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-4,12,14,19H,5-10H2,1-2H3/t12-,14-,17-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Lycoramine

The bulbs of Lycoris radiata

Biological Activity of Lycoramine

DescriptionFlavokawain C is a melanogenesis inhibitor, it inhibited melanogenesis with IC50 values of 6.9 uM. Flavokawain C has anti-tumor activity, it inhibited cell cycle and promoted apoptosis, associated with endoplasmic reticulum stress and regulation of MAPKs and Akt signaling pathways in HCT 116 human colon carcinoma cells.
TargetsNADPH-oxidase | AChR | MAPK | Akt
In vitro

The flavokawains: uprising medicinal chalcones[Reference: WebLink]

Cancer Cell International 2013, 13:102

Plant-based compounds have been in the spotlight in search of new and promising drugs.
METHODS AND RESULTS:
Flavokawain A, Flavokawain B and Flavokawain C are naturally occurring chalcones that have been isolated from several medicinal plants; namely the piper methysticum or commercially known as the kava-kava. Multiple researches have been done to evaluate the bioactivities of these compounds. It has been shown that all three flavokawains may hold promising anti-cancer effects. It has also been revealed that both flavokawain A and Flavokawain B are involved in the induction of cell cycle arrest in several cancer cell lines. Nevertheless, flavokawain B was shown to be more effective in treating in vitro cancer cell lines as compared to flavokawain A and Flavokawain C. Flavokawain B also exerts antinociceptive effects as well as antiinflammation properties.
CONCLUSIONS:
This mini-review attempts to discuss the biological properties of all the flavokawains that have been reported

Flavokawains B and C, melanogenesis inhibitors, isolated from the root of Piper methysticum and synthesis of analogs.[Pubmed: 25597012]

Bioorg Med Chem Lett. 2015 Feb 15;25(4):799-802.

The ethanolic extract of the root of Piper methysticum was found to inhibit melanogenesis in MSH-activated B16 melanoma cells.
METHODS AND RESULTS:
Flavokawain B and Flavokawain C were isolated from this extract based on their anti-melanogenesis activity and found to inhibit melanogenesis with IC50 values of 7.7μM and 6.9μM, respectively. Flavokawain analogs were synthesized through a Claisen-Schmidt condensation of their corresponding acetophenones and benzaldehydes and were evaluated in terms of their tyrosinase inhibitory and anti-melanogenesis activities.
CONCLUSIONS:
Compound 1b was the most potent of these with an IC50 value of 2.3μM in melanogenesis inhibition assays using MSH-activated B16 melanoma cells.

Protocol of Lycoramine

Cell Research

Flavokawain C Inhibits Cell Cycle and Promotes Apoptosis, Associated with Endoplasmic Reticulum Stress and Regulation of MAPKs and Akt Signaling Pathways in HCT 116 Human Colon Carcinoma Cells.[Pubmed: 26859847 ]

PLoS One. 2016 Feb 9;11(2):e0148775.

Flavokawain C (FKC) is a naturally occurring chalcone which can be found in Kava (Piper methysticum Forst) root. The present study evaluated the effect of FKC on the growth of various human cancer cell lines and the underlying associated mechanisms.
METHODS AND RESULTS:
FKC showed higher cytotoxic activity against HCT 116 cells in a time- and dose-dependent manner in comparison to other cell lines (MCF-7, HT-29, A549 and CaSki), with minimal toxicity on normal human colon cells. The apoptosis-inducing capability of FKC on HCT 116 cells was evidenced by cell shrinkage, chromatin condensation, DNA fragmentation and increased phosphatidylserine externalization. FKC was found to disrupt mitochondrial membrane potential, resulting in the release of Smac/DIABLO, AIF and cytochrome c into the cytoplasm. Our results also revealed that FKC induced intrinsic and extrinsic apoptosis via upregulation of the levels of pro-apoptotic proteins (Bak) and death receptors (DR5), while downregulation of the levels of anti-apoptotic proteins (XIAP, cIAP-1, c-FlipL, Bcl-xL and survivin), resulting in the activation of caspase-3, -8 and -9 and cleavage of poly(ADP-ribose) polymerase (PARP). FKC was also found to cause endoplasmic reticulum (ER) stress, as suggested by the elevation of GADD153 protein after FKC treatment. After the cells were exposed to FKC (60μM) over 18hrs, there was a substantial increase in the phosphorylation of ERK 1/2. The expression of phosphorylated Akt was also reduced. FKC also caused cell cycle arrest in the S phase in HCT 116 cells in a time- and dose-dependent manner and with accumulation of cells in the sub-G1 phase. This was accompanied by the downregulation of cyclin-dependent kinases (CDK2 and CDK4), consistent with the upregulation of CDK inhibitors (p21Cip1 and p27Kip1), and hypophosphorylation of Rb.

Lycoramine Dilution Calculator

Concentration (start)
x
Volume (start)
=
Concentration (final)
x
Volume (final)
 
 
 
C1
V1
C2
V2

calculate

Lycoramine Molarity Calculator

Mass
=
Concentration
x
Volume
x
MW*
 
 
 
g/mol

calculate

Preparing Stock Solutions of Lycoramine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.4554 mL 17.2771 mL 34.5543 mL 69.1085 mL 86.3856 mL
5 mM 0.6911 mL 3.4554 mL 6.9109 mL 13.8217 mL 17.2771 mL
10 mM 0.3455 mL 1.7277 mL 3.4554 mL 6.9109 mL 8.6386 mL
50 mM 0.0691 mL 0.3455 mL 0.6911 mL 1.3822 mL 1.7277 mL
100 mM 0.0346 mL 0.1728 mL 0.3455 mL 0.6911 mL 0.8639 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

Organizitions Citing Our Products recently

 
 
 

Calcutta University

University of Minnesota

University of Maryland School of Medicine

University of Illinois at Chicago

The Ohio State University

University of Zurich

Harvard University

Colorado State University

Auburn University

Yale University

Worcester Polytechnic Institute

Washington State University

Stanford University

University of Leipzig

Universidade da Beira Interior

The Institute of Cancer Research

Heidelberg University

University of Amsterdam

University of Auckland
TsingHua University
TsingHua University
The University of Michigan
The University of Michigan
Miami University
Miami University
DRURY University
DRURY University
Jilin University
Jilin University
Fudan University
Fudan University
Wuhan University
Wuhan University
Sun Yat-sen University
Sun Yat-sen University
Universite de Paris
Universite de Paris
Deemed University
Deemed University
Auckland University
Auckland University
The University of Tokyo
The University of Tokyo
Korea University
Korea University
Featured Products
New Products
 

References on Lycoramine

Cooperative hydrogen bonds and mobility of the non-aromatic ring as selectivity determinants for human acetylcholinesterase to similar anti-Alzheimer's galantaminics: a computational study.[Pubmed:29697300]

J Biomol Struct Dyn. 2019 Apr;37(7):1843-1856.

Galantamine (Gnt) is a natural alkaloid inhibitor of acetylcholinesterase and is presently one of the most used drugs in the treatment against Alzheimer's disease during both the initial and intermediate stages. Among several natural Gnt derivatives, sanguinine (Sng) and Lycoramine (Lyc) attract attention because of the way their subtle chemical differences from Gnt lead to drastic and opposite distinctions in inhibitory effects. However, to date, there is no solved structure for these natural derivatives. In the present study, we applied computational modeling and free energy calculation methods to better elucidate the molecular basis of the subtle distinctions between these derivatives and Gnt. The results showed that differences in the mobility of the non-aromatic ring carried by the Lyc-like sp(2)-sp(3) modification display drastic conformational, vibrational, and entropic penalties at binding compared to Gnt. Additionally, the establishment of a stronger hydrogen bond network added enthalpic advantages for the linkage of the Sng-like methoxy-hydroxy substituted ligands. These results, which suggest an affinity ranking in agreement with that found in the literature, provided insights that are helpful for future planning and development of new anti-Alzheimer's disease drugs.

Catalytic asymmetric total synthesis of (-)-galanthamine and (-)-lycoramine.[Pubmed:25847447]

Angew Chem Int Ed Engl. 2015 May 18;54(21):6255-9.

The catalytic asymmetric total syntheses of (-)-galanthamine (1) and (-)-Lycoramine (2) have been achieved by using a conceptually new strategy featuring two metal-catalyzed reactions as the key steps. A new method for the construction of 3,4-fused benzofurans has been developed through a palladium-catalyzed intramolecular Larock annulation reaction, which was successfully applied to the construction of the ABD tricyclic skeleton of 1 and 2. To achieve the asymmetric synthesis of 1 and 2, a Sc(III)/N,N'-dioxide complex was used to catalyze the enantioselective conjugate addition of 3-alkyl-substituted benzofuranone to methyl vinyl ketone for the construction of a chiral quaternary carbon center.

Formal synthesis of (+/-)-galanthamine and (+/-)-lycoramine using Rh(I)-catalyzed [(3 + 2) + 1] cycloaddition of 1-ene-vinylcyclopropane and CO.[Pubmed:25558884]

J Org Chem. 2015 Feb 6;80(3):1952-6.

An efficient strategy using Rh(I)-catalyzed [(3 + 2) + 1] cycloaddition of 1-ene-vinylcyclopropane and CO as a key step to build the cis-hydrodibenzofuran skeleton has been developed and applied for the formal synthesis of (+/-)-galanthamine and (+/-)-Lycoramine.

Alkaloid metabolite profiles by GC/MS and acetylcholinesterase inhibitory activities with binding-mode predictions of five Amaryllidaceae plants.[Pubmed:25305596]

J Pharm Biomed Anal. 2015 Jan;102:222-8.

Acetylcholinesterase (AChE) enzymatic inhibition is an important target for the management of Alzheimer disease (AD) and AChE inhibitors are the mainstay drugs for its treatment. In order to discover new sources of potent AChE inhibitors, a combined strategy is presented based on AChE-inhibitory activity and chemical profiles by GC/MS, together with in silico studies. The combined strategy was applied on alkaloid extracts of five Amaryllidaceae species that grow in Colombia. Fifty-seven alkaloids were detected using GC/MS, and 21 of them were identified by comparing their mass-spectral fragmentation patterns with standard reference spectra in commercial and private library databases. The alkaloid extracts of Zephyranthes carinata exhibited a high level of inhibitory activity (IC50 = 5.97 +/- 0.24 mug/mL). Molecular modeling, which was performed using the structures of some of the alkaloids present in this extract and the three-dimensional crystal structures of AChE derived from Torpedo californica, disclosed their binding configuration in the active site of this AChE. The results suggested that the alkaloids 3-epimacronine and Lycoramine might be of interest for AChE inhibition. Although the galanthamine group is known for its potential utility in treating AD, the tazettine-type alkaloids should be evaluated to find more selective compounds of potential benefit for AD.

[Effect of precursor on growth and accumulation of alkaloids of Lycoris radiata suspension cells].[Pubmed:24945053]

Sheng Wu Gong Cheng Xue Bao. 2014 Feb;30(2):247-54.

In order to investigate the effects of phenylalanine, tyrosine and tyramine on the growth of Lycoris radiata suspension cells and the accumulation of alkaloids, the growth quantity of the cells as well as the content of alkaloids in cells were determined, which were treated with above three kinds of precursors alone and phenylalanine combined with tyrosine respectively. The results indicate that the addition of phenylalanine alone and addition of phenylalanine on the basis of tyrosine at high concentration (200 micromol/L) had no significant effect on the growth of Lycoris radiata suspension cells and the content of alkaloids in cells; whereas tyrosine and tyramine promoted the growth of the cells and alkaloids accumulation. Treated with tyrosine at high concentration (200 micromol/L), the content of alkaloids of the cells was 2.56-fold higher than that of the control group, the amounts of Lycoramine (3.77 mg/g) and galanthamine (4.46 mg/g) were 6.61-fold and 6.97-fold higher than that of the control group, respectively. When treated with tyramine (200 micromol/L), the amount of alkaloids in Lycoris radiata suspension cells was 2.63-fold higher than that of the control group, and the amounts of Lycoramine (4.45 mg/g) and galanthamine (5.14 mg/g) were 9.08-fold and 9.18-fold higher than that of the control group, respectively. The above results demonstrate that adding tyrosine and tyramine in the media significantly promoted the growth of the Lycoris radiata suspension cells and alkaloids accumulation in the cells.

Four new compounds from the bulbs of Lycoris aurea with neuroprotective effects against CoCl(2) and H(2)O(2)-induced SH-SY5Y cell injuries.[Pubmed:23775477]

Arch Pharm Res. 2014 Mar;37(3):315-23.

Three new alkaloids, 2alpha-hydroxy-6-O-n-butyloduline, O-n-butyllycorenine, (-)-N-(chloromethyl)Lycoramine (1-3), and a new phenolic compound, ((7S)-7-(4-hydroxyphenyl)-7-hydroxypropyl)-2'-methylbenzene-3',6'-diol (14), along with ten known alkaloids (4-13), were isolated from the bulbs of Lycoris aurea collected from Huaihua County of Hunan Province, China. Their structures were elucidated by spectroscopic methods including HRESIMS, UV, IR, and NMR. All the isolated compounds were tested for their neuroprotective effects against CoCl2 and H2O2-induced SH-SY5Y cell death. Compounds 1-7 and 10 exhibited significant neuroprotective effects against CoCl2-induced SH-SY5Y cell injury, while compounds 1-5, 7, 10 and 12 showed obvious neuroprotective effects against H2O2-induced SH-SY5Y cell death.

Zephgrabetaine: a new betaine-type amaryllidaceae alkaloid from Zephyranthes grandiflora.[Pubmed:23513717]

Nat Prod Commun. 2013 Feb;8(2):161-4.

Zephgrabetaine (1), a new betaine type Amaryllidaceae alkaloid, along with seven known alkaloids, lycorine, galanthine, Lycoramine, hamayne, haemanthamine, tortuosine, and ungeremine were isolated from the bulbs of Zephyranthes grandiflora and their structures elucidated by spectroscopic data analysis. The isolated alkaloids were tested for in vitro cytotoxic activities against two cell lines, C-6 (rat glioma cells) and CHO-K1 (Chinese hamster ovary cells). A dose dependent cytotoxic effect was exhibited by all the alkaloids on these two cancer cell lines with prominent activity of lycorine and haemanthamine.

Nonaqueous CE ESI-IT-MS analysis of Amaryllidaceae alkaloids.[Pubmed:23436771]

J Sep Sci. 2013 Mar;36(6):1078-84.

The Amaryllidaceae are widely distributed medical plants. Lycorine, Lycoramine, lycoremine, and lycobetaine are the major active alkaloids in Amaryllidaceae plants. A nonaqueous CE ESI-IT-MS method for separation, identification, and quantification of the Amaryllidaceae alkaloids has been developed. The MS(1-3) behavior has been studied and the fragmentation pathways of main fragment ions have been proposed. The effects of several factors such as composition and concentration of buffer, applied voltage, composition, and flow rate of the sheath liquid, nebulizing gas pressure, flow rate, and temperature of drying gas were investigated. Under the optimal conditions, the linear concentration range of these compounds was wide with the correlation coefficient (R(2) ) >0.99. RSDs of migration time and peak areas were <10%. The LODs were <240 ng/mL. The proposed method can be successfully applied to the determination of the related alkaloids in the Lycoris radiata roots.

Simultaneous quantification of Amaryllidaceae alkaloids from Zephyranthes grandiflora by UPLC-DAD/ESI-MS/MS.[Pubmed:22939505]

J Pharm Biomed Anal. 2012 Dec;71:187-92.

A rapid, simple and sensitive ultra performance liquid chromatography-diode array detection method (UPLC-DAD) was developed and validated for quantification of four biologically important Amaryllidaceae alkaloids viz. Lycoramine, hamayne, haemanthamine and tortuosine in Zephyranthes grandiflora. The method employed BEH C(18) column (2.1mmx100mm, 1.7mum particle size) with linear gradient elution of acetonitrile and water (0.05% formic acid) in a flow rate of 0.3mL/min and at lambda(max) 280nm. Standard calibration curve for the analytes were linear (r(2)>/=0.9999), precise (intra-day RSDs<1.33% and inter-day RSDs<2.67%) and accurate (97.8-105.3%). The developed method was applied to the quality assessment of samples collected during different seasons and showed significant variation with an optimum amounts of these alkaloids in rainy season. The method was also applied for identification of Amaryllidaceae alkaloids in the plant and overall, seventeen Amaryllidaceae alkaloids of different structural types lycorine, haemanthamine, galanthamine, narciclasine were characterised. This study provides a qualitative and quantitative method for analysis of Amaryllidaceae alkaloids.

Total synthesis of (-)-galanthamine and (-)-lycoramine via catalytic asymmetric hydrogenation and intramolecular reductive Heck cyclization.[Pubmed:22612349]

Org Lett. 2012 Jun 1;14(11):2714-7.

A synthetic strategy featuring efficient ruthenium-catalyzed asymmetric hydrogenation of racemic alpha-aryloxy cyclic ketone via dynamic kinetic resolution and palladium-catalyzed intramolecular reductive Heck cyclization has been developed for the asymmetric total synthesis of (-)-galanthamine (20.1%, 12 steps) and (-)-Lycoramine (40.2%, 10 steps).

Asymmetric synthesis of bioactive hydrodibenzofuran alkaloids: (-)-lycoramine, (-)-galanthamine, and (+)-lunarine.[Pubmed:21748835]

Angew Chem Int Ed Engl. 2011 Aug 22;50(35):8161-6.

Divergent route: a direct C-C bond-forming approach to the key aryl-substituted all-carbon quaternary stereogenic center present in bioactive hydrodibenzofuran alkaloids has been discovered. This approach involves an unprecedented organocatalytic enantioselective Michael addition of alpha-cyanoketones with acrylates and was used in a novel and divergent synthetic strategy for the title compounds in asymmetric fashion.

Alkaloid accumulation in different parts and ages of Lycoris chinensis.[Pubmed:20737914]

Z Naturforsch C. 2010 Jul-Aug;65(7-8):458-62.

The galanthamine, lycorine, and Lycoramine content of Lycoris chinensis was researched during development from young to old plants, i.e. in seeds, ten-day-old seedlings, three-month-old seedlings, one-year-old seedlings, and perennial seedlings. Notably the alkaloid level reduced to its lowest content 10 days after seed germinating. Then the accumulation of galanthamine tended to increase with age, reaching a higher value in perennial seedlings. The production pattern of lycorine and Lycoramine was found similar to that of galanthamine. Different plant organs were also evaluated for their galanthamine, lycorine, and Lycoramine contents. Mature seeds had the highest content of galanthamine (671.33 microg/g DW). Kernels, seed capsules, and root-hairs were the main repository sites for galanthamine, lycorine, and Lycoramine. The leaves were the least productive organs.

Domino double Michael-Claisen cyclizations: a powerful general tool for introducing quaternary stereocenters at C4 of cyclohexane-1,3-diones and total synthesis of diverse families of sterically congested alkaloids.[Pubmed:18781800]

J Org Chem. 2008 Oct 3;73(19):7498-508.

Reactions of substituted acetone derivatives with acrylic acid esters (>200 mol %) in the presence of t-BuOK (200 mol %) in t-BuOH-THF (1:1 by volume) turned out to proceed as a cascade process consisting of the first Michael addition, the second Michael addition, and the last Claisen reaction to afford 4,4-disubstituted cyclohexane-1,3-diones. Only more substituted enolates play the role of a Michael donor in this cascade process, and therefore the ketone took up two alkoxycarbonylethyl groups on the same carbon bearing more substituents. Such intermediates were followed by intramolecular Claisen reactions leading to cyclohexane-1,3-diones bearing quaternary stereogenic centers at C(4), which bears an alkoxycarbonylethyl group and the substituent of the starting acetone derivatives. Thus-obtained 4,4-disubstituted cyclohexane-1,3-diones were successfully employed for total syntheses of intricate alkaloids of biological interest such as (+)-aspidospermidine, (+/-)-galanthamine, (+/-)-Lycoramine, and (+/-)-mesembrine, all featuring quaternary stereogenic centers. DFT calculations provided us with clear-cut explanations for the observed chemoselectivity of the cascade process involving ketone-based enolates under thermodynamically controlled conditions.

The enantioselective synthesis of (-)-lycoramine with the Birch-Cope sequence.[Pubmed:17676911]

J Org Chem. 2007 Aug 31;72(18):6792-6.

The first enantioselective synthesis of (-)-Lycoramine has been achieved in 14 steps and 5% overall yield from the biaryl derivative 1. The synthesis applies the previously developed Birch-Cope sequence to create the key arylic quaternary stereocenter of (-)-Lycoramine with excellent enantioselective control. The product of the Birch-Cope sequence, a versatile 4,4-disubstituted-2-carboxamide-2-cyclohexen-1-one, was elaborated through an intramolecular conjugate addition of a phenol to create the dihydrofuran ring. Chemoselective elaboration of the allyl group into an amide followed by a modified Pictet-Spengler reaction generated the azepine ring.

Alkaloids of the flowers of Pancratium maritimum.[Pubmed:17253308]

Planta Med. 1998 Oct;64(7):669-70.

The defatted ethanolic extract of the fresh flowers of Pancratium maritimum L. yielded the four known alkaloids lycorine, maritidine, Lycoramine, and galanthamine. The structures of the isolated alkaloids were determined mainly through spectroscopic studies including one- and two-dimensional NMR (COSY, NOESY, DEPT, HETCOR, and HMBC) and CD techniques. Some spectral data are newly reported or revised.

Keywords:

Lycoramine,21133-52-8,Lycoramin;Dihydrogalanthamine;1,2-Dihydrogalanthamine,Natural Products, buy Lycoramine , Lycoramine supplier , purchase Lycoramine , Lycoramine cost , Lycoramine manufacturer , order Lycoramine , high purity Lycoramine

Online Inquiry for:

      Fill out the information below

      • Size:Qty: - +

      * Required Fields

                                      Result: