Narcissoside | CAS# 604-80-8 | Antioxidant

MedKoo Cat#: 573971 | Name: Narcissoside

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Description:

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

Narcissoside is a flavonoid glycoside that has been found in the plant Z. simplex and has antioxidative and antitumor activities. It scavenges 27.74, 33.41, and 63% of 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals and inhibits activation of Epstein-Barr virus early antigen (EBV-EA) induced by phorbol 12-myristate 13-acetate (TPA) in Raji cells. Narcissoside has also been shown to inhibit TPA-induced papilloma formation.

Chemical Structure

Narcissoside

CAS#604-80-8

Theoretical Analysis

MedKoo Cat#: 573971

Name: Narcissoside

CAS#: 604-80-8

Chemical Formula: C28H32O16

Exact Mass: 624.1690

Molecular Weight: 624.55

Elemental Analysis: C, 53.85; H, 5.16; O, 40.99

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 205.00
5mg	USD 405.00
10mg	USD 650.00
25mg	USD 1,000.00

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Synonym

Narcissoside

IUPAC/Chemical Name

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

InChi Key

UIDGLYUNOUKLBM-GEBJFKNCSA-N

InChi Code

InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(43-16)44-26-20(34)17-13(31)6-11(29)7-15(17)42-25(26)10-3-4-12(30)14(5-10)39-2/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9-,16+,18-,19+,21+,22-,23+,24+,27+,28-/m0/s1

SMILES Code

OC1=CC(O)=C(C(C(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]3[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O3)O2)=C(C4=CC=C(O)C(OC)=C4)O5)=O)C5=C1

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

>3 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:

Narcissin (Narcissoside), a flavonol glycoside, exhibits evident scavenging activity against both authentic ONOO- and SIN-1-derived ONOO- with IC50s of 3.5 and 9.6 μM, respectively.

In vitro activity:

Narcissoside's radical scavenging activities were evaluated by DPPH• and ABTS•+ scavenging activities. On the other hand, IC50 values were calculated for DPPH•, and ABTS•+ scavenging, acetylcholinesterase, and α-glucosidase inhibition effects of narcissoside. IC50 values narcissoside, as 11.54 nM for AChE and 65.58 nM for α-glucosidase were calculated with % Activity-[Inhibitory] graphs. Reference: Arch Physiol Biochem. 2023 Apr;129(2):405-415. https://pubmed.ncbi.nlm.nih.gov/33075241/

In vivo activity:

To further evaluate the utility of NCS in animals, this study used the widely used C. elegans model. First, this study determined the optimal NCS treatment dose for this model using a food clearance assay. The results showed that the food clearance curves of the N2, BZ555, NL5901, and DA2123 strains were significantly slower when the medium was supplemented, with more than 4-mM NCS compared to the untreated group (Figure 9A). Additionally, nematode body size and number of offspring were significantly reduced under a dissecting microscope (data not shown). These data reflect that NCS above 4 mM is toxic to nematode feeding, growth, and reproduction. Reference: Antioxidants (Basel). 2022 Oct 23;11(11):2089. https://pubmed.ncbi.nlm.nih.gov/36358461/

	Solvent	mg/mL	mM
Solubility
	DMF	5.0	8.01
	DMSO	51.5	82.46
	PBS (pH 7.2)	5.0	8.01

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 624.55 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.

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. Liu T, Cao L, Zhang T, Fu H. Molecular docking studies, anti-Alzheimer's disease, antidiabetic, and anti-acute myeloid leukemia potentials of narcissoside. Arch Physiol Biochem. 2023 Apr;129(2):405-415. doi: 10.1080/13813455.2020.1828483. Epub 2020 Oct 19. PMID: 33075241. 2. Dubey K, Dubey R. Computation screening of narcissoside a glycosyloxyflavone for potential novel coronavirus 2019 (COVID-19) inhibitor. Biomed J. 2020 Aug;43(4):363-367. doi: 10.1016/j.bj.2020.05.002. Epub 2020 May 18. PMID: 32426388; PMCID: PMC7233213. 3. Fu RH, Tsai CW, Liu SP, Chiu SC, Chen YC, Chiang YT, Kuo YH, Shyu WC, Lin SZ. Neuroprotective Capability of Narcissoside in 6-OHDA-Exposed Parkinson's Disease Models through Enhancing the MiR200a/Nrf-2/GSH Axis and Mediating MAPK/Akt Associated Signaling Pathway. Antioxidants (Basel). 2022 Oct 23;11(11):2089. doi: 10.3390/antiox11112089. PMID: 36358461; PMCID: PMC9686521. 4. Ha T, Kim MS, Kang B, Kim K, Hong SS, Kang T, Woo J, Han K, Oh U, Choi CW, Hong GS. Lotus Seed Green Embryo Extract and a Purified Glycosyloxyflavone Constituent, Narcissoside, Activate TRPV1 Channels in Dorsal Root Ganglion Sensory Neurons. J Agric Food Chem. 2022 Apr 6;70(13):3969-3978. doi: 10.1021/acs.jafc.1c07724. Epub 2022 Mar 28. PMID: 35343690.

In vitro protocol:

In vivo protocol:

1. Fu RH, Tsai CW, Liu SP, Chiu SC, Chen YC, Chiang YT, Kuo YH, Shyu WC, Lin SZ. Neuroprotective Capability of Narcissoside in 6-OHDA-Exposed Parkinson's Disease Models through Enhancing the MiR200a/Nrf-2/GSH Axis and Mediating MAPK/Akt Associated Signaling Pathway. Antioxidants (Basel). 2022 Oct 23;11(11):2089. doi: 10.3390/antiox11112089. PMID: 36358461; PMCID: PMC9686521. 2. Ha T, Kim MS, Kang B, Kim K, Hong SS, Kang T, Woo J, Han K, Oh U, Choi CW, Hong GS. Lotus Seed Green Embryo Extract and a Purified Glycosyloxyflavone Constituent, Narcissoside, Activate TRPV1 Channels in Dorsal Root Ganglion Sensory Neurons. J Agric Food Chem. 2022 Apr 6;70(13):3969-3978. doi: 10.1021/acs.jafc.1c07724. Epub 2022 Mar 28. PMID: 35343690.

1. Ito, H., Miyake, M., Nishatani, E., et al. Anti-tumor promoting activity of polyphenols from Cowania mexicana and Coleogyne ramosissima. Cancer Lett. 143(1), 5-13 (1999). 2. Abdallah, H.M., and Edmat, A. Antioxidant and anti-inflammatory activities of the major phenolics from Zygophyllum simplex L. J. Ethnaopharmacol. 205, 51-56 (2017).