Narciclasine

CHF 90.00
In stock
AG-CN2-0524-C500500 µgCHF 90.00
AG-CN2-0524-M0011 mgCHF 160.00
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Product Details
Synonyms (+)-Narciclasine; (+)-Lycoricidinol; BRN1087400; NSC266535
Product Type Chemical
Properties
Formula

C14H13NO7

MW 307.3
CAS 29477-83-6
RTECS JI5000000
Source/Host Chemicals Isolated from Narcissus sp.
Purity Chemicals ≥98% (HPLC)
Appearance Pale grey powder.
Solubility Soluble in DMSO (30mg/ml).
Identity Determined by 1H-NMR.
InChi Key LZAZURSABQIKGB-AEKGRLRDSA-N
Smiles OC1=C(C(N[C@]2([H])C3=C[C@H](O)[C@@H](O)[C@H]2O)=O)C3=CC4=C1OCO4
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Protect from light.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • Plant growth modulator/inhibitor.
  • Anticancer agent. Exhibits antiproliferative and pro-apoptotic effects in carcinoma cells and displays cytotoxic activity against a panel of 60 cancer cell lines.  Shown to promote autophagy-induced apoptosis and to slow cell cycle progression.
  • Inhibits protein synthesis by interacting with the 60S ribosome subunit.
  • Regulates the Rho/ROCK/LIM kinase/cofilin pathway. Stimulates RhoA activation and induces actin polymerization.
  • Anti-obesity agent. Attenuates diet-induced obesity (DIO) in mice by promoting oxidative metabolism in skeletal muscle and energy expenditure.
  • Anti-inflammatory agent suppressing NF-κB-dependent gene transcription.
  • Antiviral agent in vitro.
  • Antifungal agent.
  • Shown to inhibit amyloid plaque formation in an Alzheimer's disease model.
Product References
  1. Narciclasine: an antimitotic substance from Narcissus bulbs:  G. Ceriotti; Nature 213, 595 (1967)
  2. Narciclasine: an antitumour alkaloid which blocks peptide bond formation by eukaryotic ribosomes: L. Carrasco, et al.; FEBS Lett. 52, 236 (1975)
  3. Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances: B. Gabrielsen, et al.; J. Nat. Prod. 55, 1569 (1992)
  4. The Amaryllidaceae isocarbostyril narciclasine induces apoptosis by activation of the death receptor and/or mitochondrial pathways in cancer cells but not in normal fibroblasts: P. Dumont, et al.; Neoplasia 9, 766 (2007)
  5. Chemistry, biology and medicinal potential of Narciclasine and its congeners: A. Kornienko & A. Evidente: Chem. Rev. 108, 1982 (2008) (Review)
  6. Structure-activity relationship analysis of novel derivatives of narciclasine (an Amaryllidaceae isocarbostyril derivative) as potential anticancer agents: L. Ingrassia, et al.; J. Med. Chem. 52, 1100 (2009)
  7. Narciclasine, a plant growth modulator, activates Rho and stress fibers in glioblastoma cells: F. Lefranc, et al.; Mol. Cancer Ther. 8, 1739 (2009)
  8. Narciclasine as well as other Amaryllidaceae isocarbostyrils are promising GTP-ase targeting agents against brain cancers: G. Van Goietsenoven, et al.; Med. Res. Rev. 33, 439 (2013) (Review)
  9. Narciclasine inhibits the responses of Arabidopsis roots to auxin: Y. Hu, et al.; Planta 236, 597 (2012)
  10. Haemanthus coccineus extract and its main bioactive component narciclasine display profound anti-inflammatory activities in vitro and in vivo: S. Fuchs, et al.; J. Cell Mol. Med. 19, 1021 (2015)
  11. Effect of Lycoris chejuensis and Its Active Components on Experimental Models of Alzheimer's Disease: J. Kim, et al.; J. Agric. Food Chem. 63, 6979 (2015)
  12. Narciclasine - an Amaryllidaceae alkaloid with potent antitumor and anti-inflammatory properties: R. Furst, et al.; Planta Med. 82, 1389 (2016) (Review)
  13. Narciclasine attenuates diet-induced obesity by promoting oxidative metabolism in skeletal muscle: S.G. Julien, et al.; PLoS Biol. 15, e1002597 (2017)
  14. Metabolism: Narciclasine boosts energy metabolism: C. Greenhill; Nat. Rev. Endocrinol. 13, 189 (2017) (Review)
  15. Narciclasine induces autophagy-dependent apoptosis in triple-negative breast cancer cells by regulating the AMPK-ULK1 axis: C. Cao, et al.; Cell Prolif. 51, e12518 (2018)
  16. Insight to the antifungal properties of Amaryllidaceae constituents: J.J Nair & J. van Staden; Phytomedicine (Epub ahead of print) (2018) (Review)
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