An isocarbostyril alkaloid with diverse biological activities
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Narciclasine

Item No. 20361

Technical Information
Formal Name
(2S,3R,4S,4aR)-3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one
CAS Number
29477-83-6
Synonyms
  • (+)-Lycoricidinol
  • (+)-Narciclasine
  • NSC 266535
Molecular Formula
C14H13NO7
Formula Weight
Purity
≥98%
A crystalline solid
λmax
213, 252, 302 nm
SMILES
OC1=C(C(N[C@]2([H])C3=C[C@H](O)[C@@H](O)[C@H]2O)=O)C3=CC4=C1OCO4
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
InChi Key
LZAZURSABQIKGB-AEKGRLRDSA-N
Origin
Plant/Narcissus sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Narciclasine is an isocarbostyril alkaloid that has been found in Narcissus and has diverse biological activities.1,2,3,4,5 It selectively induces apoptosis in PC3 prostate and MCF-7 and MDA-MB-231 breast cancer cells over CCD-25Lu fibroblasts at 1 µM.1 Narciclasine has antiproliferative activity against a panel of six glioblastoma cancer cell lines (mean IC50 = ~50 nM), induces actin stress fiber formation in U373 MG glioblastoma cells, and increases survival in an orthotopic Hs 683 glioblastoma mouse xenograft model.2 It also inhibits neurite outgrowth in SH-SY5Y cells with a 10% effective concentration (EC10) value of 4.44 nM and suppresses the proliferation of isolated human T cells (IC50 = 14 nM).3,4 Intradermal administration of narciclasine (2 mg/kg) decreases disease severity and prevents increases in spleen weight in a mouse model of psoriasis induced by imiquimod (Item No. 14956).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dumont, P., Ingrassia, L., Rouzeau, S., et alThe Amaryllidaceae isocarbostyril narciclasine induces apoptosis by activation of the death receptor and/or mitochondrial pathways in cancer cells but not in normal fibroblasts. Neoplasia 9(9), 766-776 (2007).

    2. Lefranc, F., Sauvage, S., Van Goietsenoven, G., et alNarciclasine, a plant growth modulator, activates Rho and stress fibers in glioblastoma cells. Mol. Cancer Ther. 8(7), 1739-1750 (2009).

    3. Braun, G., Herberth, G., Krauss, M., et alNeurotoxic mixture effects of chemicals extracted from blood of pregnant women. Science 386(6719), 301-309 (2024).

    4. Wang, W.-L., Wu, X.-Y., Luo, X.-Y., et alImmunosuppressive alkaloids from Narcissus tazetta subsp. Chinensis and the mechanism of (+)-narciclasine in vitro and in vivo. Phytochemistry 225:114198, (2024).

    5. Kong, Y., Jiang, J., Huang, Y., et alNarciclasine inhibits phospholipase A2 and regulates phospholipid metabolism to ameliorate psoriasis-like dermatitis. Front. Immunol. 13:1094375, (2023).