Narciclasine

Cas：29477-83-6

Product Information：

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 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

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).

HS Tariff Code: 2934.99.9001

In Vitro：

Narciclasine activates Rho and stress fibers in glioblastoma multiforme cells. The mean IC50 of ~50 nM calculated on the 6 human glioblastoma multiforme (U373, Hs683, GL19, GL5, GL16, GL17), The mean IC50 value of 47 nM for Narciclasine across a panel of 60 cancer cell lines[1]. Bioassay-guided fractionation of the A. belladonna extract resulted in the identification of lycorine as the bio-active compound. The IC50 measured for radicle growth inhibition is 0.1 µM for Narciclasine.

In Vivo：

The i.v. regimen of Narciclasine at 1 mg/kg significantly (P=0.02) increases the survival of GL19 glioblastoma multiforme-bearing mice. Narciclasine when given orally at the same dose five times a week for 5 consecutive weeks also significantly increases animal survival in this model (P=0.008). Oral treatment with Narciclasine at 1 mg/kg significantly increases the survival (P=0.004) of Hs683 glioblastoma multiforme-bearing mice. Increasing the number of doses administered per week does not increase the survival of these Hs683 glioblastoma multiforme-bearing mice. Narciclasine appears to show similar increased survival in these models to temozolomide but at appreciable lower doses and following both oral and i.v. administration.

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.

Products are for research use only. Not for human use.