Narciclasine
featured

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

MedKoo CAT#: 326780

CAS#: 29477-83-6

Description: Narciclasine is a toxic alkaloid found in various Amaryllidaceae species. Narciclasine is a potential allelochemical and affects subcellular trafficking of auxin transporter proteins and actin cytoskeleton dynamics in Arabidopsis roots. Narciclasine inhibits the responses of Arabidopsis roots to auxin. Narciclasine modulates polar auxin transport in Arabidopsis roots.

Chemical Structure

img
Narciclasine
CAS# 29477-83-6
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326780
Name: Narciclasine
CAS#: 29477-83-6
Chemical Formula: C14H13NO7
Exact Mass: 307.07
Molecular Weight: 307.258
Elemental Analysis: C, 54.73; H, 4.26; N, 4.56; O, 36.45

Price and Availability

Size Price Availability Quantity
1mg USD 250
Bulk inquiry

Synonym: Lycorcidinol; Lycoricidin-A; NSC 266535; Narciclasine.

IUPAC/Chemical Name: (2S,3R,4S,4aR)-2,3,4,7-tetrahydroxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

InChi Key: LZAZURSABQIKGB-AEKGRLRDSA-N

InChi Code: InChI=1S/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h1-2,6,9-10,12,16-19H,3H2,(H,15,20)/t6-,9+,10+,12-/m0/s1

SMILES Code: O=C1N[C@@]2([H])[C@H](O)[C@H](O)[C@@H](O)C=C2C3=CC(OCO4)=C4C(O)=C13

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:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Narciclasine is a plant growth modulator.
In vitro activity: Narciclasine (1) is a plant growth regulator that has been previously demonstrated to be proapoptotic to cancer cells at high concentrations (> or = 1 microM). Data generated in the present study show that narciclasine displays potent antitumor effects in apoptosis-resistant as well as in apoptosis-sensitive cancer cells by impairing the organization of the actin cytoskeleton in cancer cells at concentrations that are not cytotoxic (IC(50) values of 30-90 nM). Reference: J Med Chem. 2009 Feb 26;52(4):1100-14. https://pubmed.ncbi.nlm.nih.gov/19199649/
In vivo activity: To evaluate the cardioprotective effects of narciclasine on inflammation in LPS-induced AMI, the levels of inflammatory indicators were measured. An indicator of neutrophil infiltration, MPO, was increased in the LPS group, and narciclasine effectively abrogated this increase (Figure 3A). Additionally, the mRNA expression levels of IL-6, IL-1β, TNF-α, and VEGF in heart tissues were significantly increased in LPS-induced AMI but were notably attenuated by narciclasine treatment (Figure 3B). These results demonstrated that narciclasine could attenuate heart inflammation in LPS-induced AMI. Reference: Aging (Albany NY). 2021 May 25;13(11):15151-15163. https://pubmed.ncbi.nlm.nih.gov/34035183/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 39.2 127.72

Preparing Stock Solutions

The following data is based on the product molecular weight 307.26 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.

Recalculate based on batch purity %
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: 1. Lefranc F, Sauvage S, Van Goietsenoven G, Mégalizzi V, Lamoral-Theys D, Debeir O, Spiegl-Kreinecker S, Berger W, Mathieu V, Decaestecker C, Kiss R. Narciclasine, a plant growth modulator, activates Rho and stress fibers in glioblastoma cells. Mol Cancer Ther. 2009 Jul;8(7):1739-50. doi: 10.1158/1535-7163.MCT-08-0932. Epub 2009 Jun 16. Erratum in: Mol Cancer Ther. 2012 May;11(5):1216-7. PMID: 19531573. 2. Ingrassia L, Lefranc F, Dewelle J, Pottier L, Mathieu V, Spiegl-Kreinecker S, Sauvage S, El Yazidi M, Dehoux M, Berger W, Van Quaquebeke E, Kiss R. Structure-activity relationship analysis of novel derivatives of narciclasine (an Amaryllidaceae isocarbostyril derivative) as potential anticancer agents. J Med Chem. 2009 Feb 26;52(4):1100-14. doi: 10.1021/jm8013585. PMID: 19199649. 3. Tang R, Jia L, Li Y, Zheng J, Qi P. Narciclasine attenuates sepsis-induced myocardial injury by modulating autophagy. Aging (Albany NY). 2021 May 25;13(11):15151-15163. doi: 10.18632/aging.203078. Epub 2021 May 25. PMID: 34035183; PMCID: PMC8221305. 4. Zhao D, Zhang LJ, Huang TQ, Kim J, Gu MY, Yang HO. Narciclasine inhibits LPS-induced neuroinflammation by modulating the Akt/IKK/NF-κB and JNK signaling pathways. Phytomedicine. 2021 May;85:153540. doi: 10.1016/j.phymed.2021.153540. Epub 2021 Mar 9. PMID: 33773188.
In vitro protocol: 1. Lefranc F, Sauvage S, Van Goietsenoven G, Mégalizzi V, Lamoral-Theys D, Debeir O, Spiegl-Kreinecker S, Berger W, Mathieu V, Decaestecker C, Kiss R. Narciclasine, a plant growth modulator, activates Rho and stress fibers in glioblastoma cells. Mol Cancer Ther. 2009 Jul;8(7):1739-50. doi: 10.1158/1535-7163.MCT-08-0932. Epub 2009 Jun 16. Erratum in: Mol Cancer Ther. 2012 May;11(5):1216-7. PMID: 19531573. 2. Ingrassia L, Lefranc F, Dewelle J, Pottier L, Mathieu V, Spiegl-Kreinecker S, Sauvage S, El Yazidi M, Dehoux M, Berger W, Van Quaquebeke E, Kiss R. Structure-activity relationship analysis of novel derivatives of narciclasine (an Amaryllidaceae isocarbostyril derivative) as potential anticancer agents. J Med Chem. 2009 Feb 26;52(4):1100-14. doi: 10.1021/jm8013585. PMID: 19199649.
In vivo protocol: 1. Tang R, Jia L, Li Y, Zheng J, Qi P. Narciclasine attenuates sepsis-induced myocardial injury by modulating autophagy. Aging (Albany NY). 2021 May 25;13(11):15151-15163. doi: 10.18632/aging.203078. Epub 2021 May 25. PMID: 34035183; PMCID: PMC8221305. 2. Zhao D, Zhang LJ, Huang TQ, Kim J, Gu MY, Yang HO. Narciclasine inhibits LPS-induced neuroinflammation by modulating the Akt/IKK/NF-κB and JNK signaling pathways. Phytomedicine. 2021 May;85:153540. doi: 10.1016/j.phymed.2021.153540. Epub 2021 Mar 9. PMID: 33773188.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Hu Y, Na X, Li J, Yang L, You J, Liang X, Wang J, Peng L, Bi Y. Narciclasine, a potential allelochemical, affects subcellular trafficking of auxin transporter proteins and actin cytoskeleton dynamics in Arabidopsis roots. Planta. 2015 Dec;242(6):1349-60. doi: 10.1007/s00425-015-2373-6. Epub 2015 Aug 2. PubMed PMID: 26232920.

2: Fuchs S, Hsieh LT, Saarberg W, Erdelmeier CA, Wichelhaus TA, Schaefer L, Koch E, Fürst R. Haemanthus coccineus extract and its main bioactive component narciclasine display profound anti-inflammatory activities in vitro and in vivo. J Cell Mol Med. 2015 May;19(5):1021-32. doi: 10.1111/jcmm.12493. Epub 2015 Mar 5. PubMed PMID: 25754537; PubMed Central PMCID: PMC4420604.

3: Vshyvenko S, Reisenauer MR, Rogelj S, Hudlicky T. Synthesis and biological evaluation of unnatural derivatives of narciclasine: 7-aza-nornarciclasine and its N-oxide. Bioorg Med Chem Lett. 2014 Sep 1;24(17):4236-8. doi: 10.1016/j.bmcl.2014.07.034. Epub 2014 Jul 19. PubMed PMID: 25108300; PubMed Central PMCID: PMC4146675.

4: Hu Y, Li J, Yang L, Nan W, Cao X, Bi Y. Inhibition of root growth by narciclasine is caused by DNA damage-induced cell cycle arrest in lettuce seedlings. Protoplasma. 2014 Sep;251(5):1113-24. doi: 10.1007/s00709-014-0619-y. Epub 2014 Jan 31. PubMed PMID: 24482192.

5: Hu Y, Yang L, Na X, You J, Hu W, Liang X, Liu J, Mao L, Wang X, Wang H, Bi Y. Narciclasine inhibits the responses of Arabidopsis roots to auxin. Planta. 2012 Aug;236(2):597-612. doi: 10.1007/s00425-012-1632-z. Epub 2012 Apr 5. PubMed PMID: 22476291.

6: Van Goietsenoven G, Mathieu V, Lefranc F, Kornienko A, Evidente A, Kiss R. Narciclasine as well as other Amaryllidaceae isocarbostyrils are promising GTP-ase targeting agents against brain cancers. Med Res Rev. 2013 Mar;33(2):439-55. doi: 10.1002/med.21253. Epub 2012 Mar 14. Review. PubMed PMID: 22419031.

7: Na X, Hu Y, Yue K, Lu H, Jia P, Wang H, Wang X, Bi Y. Concentration-dependent effects of narciclasine on cell cycle progression in Arabidopsis root tips. BMC Plant Biol. 2011 Dec 28;11:184. doi: 10.1186/1471-2229-11-184. PubMed PMID: 22204558; PubMed Central PMCID: PMC3282671.

8: Lu H, Wan Q, Wang H, Na X, Wang X, Bi Y. Oxidative stress and mitochondrial dysfunctions are early events in narciclasine-induced programmed cell death in tobacco Bright Yellow-2 cells. Physiol Plant. 2012 Jan;144(1):48-58. doi: 10.1111/j.1399-3054.2011.01521.x. Epub 2011 Nov 10. PubMed PMID: 21916896.

9: Na X, Hu Y, Yue K, Lu H, Jia P, Wang H, Wang X, Bi Y. Narciclasine modulates polar auxin transport in Arabidopsis roots. J Plant Physiol. 2011 Jul 15;168(11):1149-56. doi: 10.1016/j.jplph.2011.01.025. Epub 2011 Apr 20. PubMed PMID: 21511360.

10: Lefranc F, Sauvage S, Van Goietsenoven G, Mégalizzi V, Lamoral-Theys D, Debeir O, Spiegl-Kreinecker S, Berger W, Mathieu V, Decaestecker C, Kiss R. Narciclasine, a plant growth modulator, activates Rho and stress fibers in glioblastoma cells. Mol Cancer Ther. 2009 Jul;8(7):1739-50. doi: 10.1158/1535-7163.MCT-08-0932. Epub 2009 Jun 16. Erratum in: Mol Cancer Ther. 2012 May;11(5):1216-7. PubMed PMID: 19531573.

11: Matveenko M, Banwell MG, Joffe M, Wan S, Fantino E. Biological evaluation of ent-narciclasine, ent-lycoricidine, and certain enantiomerically-related congeners. Chem Biodivers. 2009 May;6(5):685-91. doi: 10.1002/cbdv.200800319. PubMed PMID: 19479847.

12: Ingrassia L, Lefranc F, Dewelle J, Pottier L, Mathieu V, Spiegl-Kreinecker S, Sauvage S, El Yazidi M, Dehoux M, Berger W, Van Quaquebeke E, Kiss R. Structure-activity relationship analysis of novel derivatives of narciclasine (an Amaryllidaceae isocarbostyril derivative) as potential anticancer agents. J Med Chem. 2009 Feb 26;52(4):1100-14. doi: 10.1021/jm8013585. PubMed PMID: 19199649.

13: Kornienko A, Evidente A. Chemistry, biology, and medicinal potential of narciclasine and its congeners. Chem Rev. 2008 Jun;108(6):1982-2014. doi: 10.1021/cr078198u. Epub 2008 May 20. Review. PubMed PMID: 18489166; PubMed Central PMCID: PMC2856661.

14: Dumont P, Ingrassia L, Rouzeau S, Ribaucour F, Thomas S, Roland I, Darro F, Lefranc F, Kiss R. The Amaryllidaceae isocarbostyril narciclasine induces apoptosis by activation of the death receptor and/or mitochondrial pathways in cancer cells but not in normal fibroblasts. Neoplasia. 2007 Sep;9(9):766-76. PubMed PMID: 17898872; PubMed Central PMCID: PMC1993861.

15: Pettit GR, Melody N, Herald DL, Knight JC, Chapuis JC. Antineoplastic agents. 550. Synthesis of 10b(s)-epipancratistatin from (+)-narciclasine. J Nat Prod. 2007 Mar;70(3):417-22. Epub 2007 Mar 9. PubMed PMID: 17346078.

16: Ibn-Ahmed S, Khaldi M, Chrétien F, Chapleur Y. A short route to enantiomerically pure benzophenanthridinone skeleton: synthesis of lactone analogues of narciclasine and lycoricidine. J Org Chem. 2004 Oct 1;69(20):6722-31. PubMed PMID: 15387596.

17: Bi Y, Guo J, Zhang L, Wong Y. Changes in some enzymes of microbodies and plastid development in excised radish cotyledons: effect of narciclasine. J Plant Physiol. 2003 Sep;160(9):1041-9. PubMed PMID: 14593805.

18: Hudlicky T, Rinner U, Gonzalez D, Akgun H, Schilling S, Siengalewicz P, Martinot TA, Pettit GR. Total synthesis and biological evaluation of Amaryllidaceae alkaloids: narciclasine, ent-7-deoxypancratistatin, regioisomer of 7-deoxypancratistatin, 10b-epi-deoxypancratistatin, and truncated derivatives. J Org Chem. 2002 Dec 13;67(25):8726-43. Erratum in: J Org Chem. 2003 Jan 24;68(2):674. PubMed PMID: 12467383.

19: Elango S, Yan TH. A short synthesis of (+)-narciclasine via a strategy derived from stereocontrolled epoxide formation and SnCl(4)-catalyzed arene-epoxide coupling. J Org Chem. 2002 Oct 4;67(20):6954-9. PubMed PMID: 12353988.

20: Pettit GR, Melody N, Herald DL. Antineoplastic agents. 450. Synthesis of (+)-pancratistatin from (+)-narciclasine as relay(1a). J Org Chem. 2001 Apr 20;66(8):2583-7. PubMed PMID: 11304174.