narciclasine
- CAS No.
- 29477-83-6
- Chemical Name:
- narciclasine
- Synonyms
- rciclasin;NSC 266535;Narciclasin;BRN 1087400;Lycorcidinol;narciclasine;Lycoricidin-A;Narciclasine, 99.9%;(13β)-1,19-Didehydro-2α,3β,4β,7-tetrahydroxy-11,12-dinor-5,19-secocrinan-6-one;3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one
- CBNumber:
- CB41341322
- Molecular Formula:
- C14H13NO7
- Molecular Weight:
- 307.26
- MDL Number:
- MFCD01729949
- MOL File:
- 29477-83-6.mol
- MSDS File:
- SDS
narciclasine price More Price(23)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | SML2805 | Narciclasine ≥98% (HPLC) | 29477-83-6 | 1MG | $143 | 2024-03-01 | Buy |
| Sigma-Aldrich | SML2805 | Narciclasine ≥98% (HPLC) | 29477-83-6 | 5MG | $583 | 2024-03-01 | Buy |
| Sigma-Aldrich | PHL82604 | Narciclasine phyproof? Reference Substance | 29477-83-6 | 10MG | $1030 | 2024-03-01 | Buy |
| Cayman Chemical | 20361 | Narciclasine ≥98% | 29477-83-6 | 500μg | $93 | 2024-03-01 | Buy |
| Cayman Chemical | 20361 | Narciclasine ≥98% | 29477-83-6 | 1mg | $166 | 2024-03-01 | Buy |
narciclasine Chemical Properties,Uses,Production
Description
Narciclasine is a plant growth inhibitor that can be isolated from Narcissus bulbs. At 1 μM, it has been shown to induce apoptosis-mediated cytotoxicity in human cancer cells in vitro but not in normal fibroblasts. Narciclasine has been shown to regulate the Rho/Rho kinase/LIM kinase/cofilin signaling pathway by increasing GTPase RhoA activity, as well as inducing actin stress fiber formation in a RhoA-dependent manner.
Description
The bulbs of several Narcissus species contain this alkaloid which crystallizes in the form of pale yellow needles with a pronounced yellow-green fluorescence. It is best purified by recrystallization from either acetic acid or an aqueous mixture of methoxyethyl alcohol. It is dextrorotatory with [α]589 + 145° or [Qh64 + 983° (c 1.5, EtOH). The ultraviolet spectrum in neutral solution (EtOH) has absorption maxima at 252, 302 and 329 mil, while that in alkaline solution (0.01 N/NaOH) has the maxima at 219, 249,310 and 355 mil. The O-methyl ether forms shiny needles which also exhibit a strong blue fluorescence. The tri_x0002_acetate has been prepared as an amorphous, non-crystallizable substance. With FeC13 the alkaloid gives a violet colour.
Uses
Narciclasine is an antiproliferative and pro-apoptotic inducer.
Uses
Narciclasine is reasonably abundant in some Narcissus spp. and has served as a very useful intermediate for synthetic conversion into (+)-pancratistatin and to conduct a series of structure–activity relationship studies . Bicolorine, another member of the narciclasine series, is an unusual, completely aromatized quaternary alkaloid with an N-methyl group.
Definition
ChEBI: A natural product found in Narcissus pseudonarcissus.
target
Immunology & Inflammation related
storage
Store at -20°C
References
Ceriotti., Nature, 213,595 (1967)
Piozzi et al., Tetrahedron, 24, 1119 (1968)
Revised structure:
Mondon, Krohn., Tetrahedron Lett., 2123 (1970)
Savona, Piozzi, Marino., Chern. Cornrnun., 1006 (1970)
Absolute configuration:
Fuganti, Mazza.,J. Chern. Soc., Chern. Cornrnun., 239 (1972)
Crystal structure:
Immirzi, Fuganti., J. Chern. Soc., Chern. Cornrnun., 240 (1972)
Stereochemistry:
Mondon, Krohn., Tetrahedron Lett., 2085 (1972)
narciclasine Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Shanghai Zheyan Biotech Co., Ltd. | 18017610038 | zheyansh@163.com | CHINA | 3620 | 58 |
| Chengdu Biopurify Phytochemicals Ltd. | +8618080483897 | sales@biopurify.com | China | 3424 | 58 |
| Hubei Jusheng Technology Co.,Ltd. | 18871490254 | linda@hubeijusheng.com | CHINA | 28180 | 58 |
| BOC Sciences | +1-631-485-4226 | inquiry@bocsci.com | United States | 19553 | 58 |
| Neostar United (Changzhou) Industrial Co., Ltd. | +86-519-519-85557386 | marketing1@neostarunited.com | China | 8348 | 58 |
| Wuhan ChemNorm Biotech Co.,Ltd. | +86-27-8439 4403 18971486879 | sales@chemnorm.com | CHINA | 2935 | 58 |
| Aktin Chemicals, Inc. | 028-85159085 | info@aktinchem.com | CHINA | 1025 | 58 |
| InvivoChem | +1-708-310-1919 +1-13798911105 | sales@invivochem.cn | United States | 6393 | 58 |
| ZHEJIANG JIUZHOU CHEM CO., LTD | +86-0576225566889 +86-13454675544 | admin@jiuzhou-chem.com；jamie@jiuzhou-chem.com；alice@jiuzhou-chem.com | China | 19949 | 58 |
| LEAPCHEM CO., LTD. | +86-852-30606658 | market18@leapchem.com | China | 43348 | 58 |
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