Narciclasine
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    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.


Price and Availability

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Price

1mg
USD 250
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Price

Size
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Narciclasine, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 326780
Name: Narciclasine
CAS#: 29477-83-6
Chemical Formula: C14H13NO7
Exact Mass: 307.0692
Molecular Weight: 307.258
Elemental Analysis: C, 54.73; H, 4.26; N, 4.56; O, 36.45


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


Technical Data

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).

Harmonized System Code:
2934.99.90.01


References

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.