Aegeline | CAS#456-12-2

Aegeline
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 329870

CAS#: 456-12-2

Description: Aegeline is a main alkaloid isolated from Aegle marmelos Correa collected in Yogyakarta Indonesia. Aegeline inhibited the histamine release from RBL-2H3 cells induced by DNP(24)-BSA. Aegeline showed strong inhibition when RBL-2H3 cells induced by Ca(2+) stimulants such as thapsigargin and ionomycin. Tthe inhibitory effects of aegeline on the histamine release from mast cells depended on the type of mast cell and also involved some mechanisms related to intracellular Ca(2+) signaling events via the same target of the action of thapsigargin or downstream process of intracellular Ca(2+) signaling in mast cells.

Chemical Structure

Aegeline

CAS# 456-12-2

Instruction

Theoretical Analysis

MedKoo Cat#: 329870
Name: Aegeline
CAS#: 456-12-2
Chemical Formula: C18H19NO3
Exact Mass: 297.14
Molecular Weight: 297.354
Elemental Analysis: C, 72.71; H, 6.44; N, 4.71; O, 16.14

Price and Availability

Size	Price	Availability	Quantity
2g	USD 250
5g	USD 450
10g	USD 750
25g	USD 1250
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Aegeline,

IUPAC/Chemical Name: N-[2-hydroxy-2(4-methoxyphenyl) ethyl]-3-phenyl-2-propenamide

InChi Key: QRFDENJATPJOKG-KPKJPENVSA-N

InChi Code: InChI=1S/C18H19NO3/c1-22-16-10-8-15(9-11-16)17(20)13-19-18(21)12-7-14-5-3-2-4-6-14/h2-12,17,20H,13H2,1H3,(H,19,21)/b12-7+

SMILES Code: O=C(NCC(O)C1=CC=C(OC)C=C1)/C=C/C2=CC=CC=C2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 297.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Gautam S, Ishrat N, Singh R, Narender T, Srivastava AK. Aegeline from Aegle marmelos stimulates glucose transport via Akt and Rac1 signaling, and contributes to a cytoskeletal rearrangement through PI3K/Rac1. Eur J Pharmacol. 2015 Sep 5;762:419-29. doi: 10.1016/j.ejphar.2015.05.021. Epub 2015 Jun 20. PubMed PMID: 26102565.

2: Nugroho AE, Riyanto S, Sukari MA, Maeyama K. Effects of aegeline, a main alkaloid of Aegle Marmelos Correa leaves, on the histamine release from mast cells. Pak J Pharm Sci. 2011 Jul;24(3):359-67. PubMed PMID: 21715270.

3: Avula B, Chittiboyina AG, Wang YH, Sagi S, Raman V, Wang M, Khan IA. Simultaneous Determination of Aegeline and Six Coumarins from Different Parts of the Plant Aegle marmelos Using UHPLC-PDA-MS and Chiral Separation of Aegeline Enantiomers Using HPLC-ToF-MS. Planta Med. 2016 Apr;82(6):580-8. doi: 10.1055/s-0042-103160. Epub 2016 Apr 7. PubMed PMID: 27054911.

4: Manda VK, Avula B, Chittiboyina AG, Khan IA, Walker LA, Khan SI. Inhibition of CYP3A4 and CYP1A2 by Aegle marmelos and its constituents. Xenobiotica. 2016;46(2):117-25. doi: 10.3109/00498254.2015.1053006. Epub 2015 Aug 6. PubMed PMID: 26247834.

5: Klontz KC, DeBeck HJ, LeBlanc P, Mogen KM, Wolpert BJ, Sabo JL, Salter M, Seelman SL, Lance SE, Monahan C, Steigman DS, Gensheimer K. The Role of Adverse Event Reporting in the FDA Response to a Multistate Outbreak of Liver Disease Associated with a Dietary Supplement. Public Health Rep. 2015 Sep-Oct;130(5):526-32. PubMed PMID: 26327730; PubMed Central PMCID: PMC4529836.

6: Karmase A, Jagtap S, Bhutani KK. Anti adipogenic activity of Aegle marmelos Correa. Phytomedicine. 2013 Nov 15;20(14):1267-71. doi: 10.1016/j.phymed.2013.07.011. Epub 2013 Aug 23. PubMed PMID: 23972792.

7: Nugroho AE, Agistia DD, Tegar M, Purnomo H. Interaction of active compounds from Aegle marmelos CORREA with histamine-1 receptor. Bioinformation. 2013 Apr 30;9(8):383-7. doi: 10.6026/97320630009383. Print 2013. PubMed PMID: 23750086; PubMed Central PMCID: PMC3670119.

8: Sarkar S, Sonkar R, Bhatia G, Tadigoppula N. Synthesis of new N-acryl-1-amino-2-phenylethanol and N-acyl-1-amino-3-aryloxypropanols and evaluation of their antihyperlipidemic, LDL-oxidation and antioxidant activity. Eur J Med Chem. 2014 Jun 10;80:135-44. doi: 10.1016/j.ejmech.2014.04.020. Epub 2014 Apr 8. PubMed PMID: 24769351.

9: Mohammed MM, Ibrahim NA, El-Sakhawy FS, Mohamed KM, Deabes DA. Two new cytotoxic furoquinoline alkaloids isolated from Aegle marmelos (Linn.) Correa. Nat Prod Res. 2016 Jan 4:1-8. [Epub ahead of print] PubMed PMID: 26729368.

10: Roytman MM, Pörzgen P, Lee CL, Huddleston L, Kuo TT, Bryant-Greenwood P, Wong LL, Tsai N. Outbreak of severe hepatitis linked to weight-loss supplement OxyELITE Pro. Am J Gastroenterol. 2014 Aug;109(8):1296-8. doi: 10.1038/ajg.2014.159. PubMed PMID: 25091255.

11: BANERJEE SK, CHAKRAVARTI RN. ACTION OF RANEY NICKEL ON AEGELINE, AEGELONE AND DIHYDROAEGELINE. Bull Calcutta Sch Trop Med. 1965 Jan;13:16-7. PubMed PMID: 14281049.

12: Heidemann LA, Navarro VJ, Ahmad J, Hayashi PH, Stolz A, Kleiner DE, Fontana RJ. Severe Acute Hepatocellular Injury Attributed to OxyELITE Pro: A Case Series. Dig Dis Sci. 2016 Sep;61(9):2741-8. doi: 10.1007/s10620-016-4181-7. Epub 2016 May 3. Erratum in: Dig Dis Sci. 2016 Oct 6;:. PubMed PMID: 27142670; PubMed Central PMCID: PMC4982804.

13: Narender T, Rajendar K, Sarkar S, Singh VK, Chaturvedi U, Khanna AK, Bhatia G. Synthesis of novel N-(2-hydroxy-2-p-tolylethyl)-amide and N-(2-oxo-2-p-tolylethyl)-amide derivatives and their antidyslipidemic and antioxidant activity. Bioorg Med Chem Lett. 2011 Nov 1;21(21):6393-7. doi: 10.1016/j.bmcl.2011.08.099. Epub 2011 Aug 28. PubMed PMID: 21930379.

14: Narender T, Shweta S, Tiwari P, Papi Reddy K, Khaliq T, Prathipati P, Puri A, Srivastava AK, Chander R, Agarwal SC, Raj K. Antihyperglycemic and antidyslipidemic agent from Aegle marmelos. Bioorg Med Chem Lett. 2007 Mar 15;17(6):1808-11. Epub 2006 Dec 15. PubMed PMID: 17197179.

15: Williams C, Espinosa OA, Montenegro H, Cubilla L, Capson TL, Ortega-Barría E, Romero LI. Hydrosoluble formazan XTT: its application to natural products drug discovery for Leishmania. J Microbiol Methods. 2003 Dec;55(3):813-6. PubMed PMID: 14607426.

16: Baeza A, Nájera C, Sansano JM, Saá JM. Binolam-AlCl: a two-centre catalyst for the synthesis of enantioenriched cyanohydrin O-phosphates. Chemistry. 2005 Jun 20;11(13):3849-62. PubMed PMID: 15776489.

17: Pawar RS, Grundel E. Overview of regulation of dietary supplements in the USA and issues of adulteration with phenethylamines (PEAs). Drug Test Anal. 2017 Mar;9(3):500-517. doi: 10.1002/dta.1980. Epub 2016 Jun 3. Review. PubMed PMID: 27259162.

18: Singh SP, Sashidhara KV. Lipid lowering agents of natural origin: An account of some promising chemotypes. Eur J Med Chem. 2017 Sep 14;140:331-348. doi: 10.1016/j.ejmech.2017.09.020. [Epub ahead of print] Review. PubMed PMID: 28987600.

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Aegeline featured