Scolymoside | CAS#20633-84-5 | Diverse flavonoid glycoside

MedKoo Cat#: 464798 | Name: Scolymoside

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Description:

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

Scolymoside, also known as luteolin 7-O-rutinoside, is a polyketide-derived flavonoid glycoside that has been found in V. bugulifolium. Scolymoside has both anti-arthritic and antifungal activities.

Chemical Structure

Scolymoside

CAS#20633-84-5

Theoretical Analysis

MedKoo Cat#: 464798

Name: Scolymoside

CAS#: 20633-84-5

Chemical Formula: C27H30O15

Exact Mass: 594.1585

Molecular Weight: 594.52

Elemental Analysis: C, 54.55; H, 5.09; O, 40.37

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 750.00	2 Weeks

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Synonym

Scolymoside; Skolimoside; Luteolin 7-β-Rutinoside; Luteolin 7-Rutinoside; Luteolin 7-O-Rutinoside;

IUPAC/Chemical Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-(((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

MGYBYJXAXUBTQF-FOBVWLSUSA-N

InChi Code

InChI=1S/C27H30O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-7,9,18,20-30,32-37H,8H2,1H3/t9-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1

SMILES Code

O=C1C2=C(C=C(C=C2OC(C3=CC(O)=C(O)C=C3)=C1)O[C@@H]4O[C@H](CO[C@H]5[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O5)[C@@H](O)[C@H](O)[C@H]4O)O

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Scolymoside scavenges DPPH radicals in a cell-free assay when used at concentrations ranging from 1 to 50 µM. Scolymoside is active against B. subtilis, S. aureus, A. tumefaciens, M. luteus, E. coli, and P. aeruginosa (MICs = 100-200 µg/ml). It is also active against C. albicans, S. cerevisiae, and C. lusitaniae (MICs = 100, 200, and 50 µg/ml, respectively) and the plant pathogenic fungus A. niger (MIC = 100 µg/ml). Scolymoside decreases hepatic and renal injury and increases survival in a mouse model of polyphosphate-induced lethal endotoxemia.

In vitro activity:

The results of this study suggest that vicenin-2 and scolymoside have therapeutic potential for various systemic inflammatory diseases. Vicenin-2 and scolymoside inhibited polyP-mediated barrier disruption, cell adhesion molecules expression, and leukocyte to HUVEC adhesion/migration. In HUVECs, vicenin-2 and scolymoside inhibited polyP-induced NF-κB activation and TNF-α and IL-6 production. Reference: Inflamm Res. 2016 Mar;65(3):203-12. https://pubmed.ncbi.nlm.nih.gov/26621502/

In vivo activity:

In a murine model of lipopolysaccharide- mediated vascular inflammation, vicenin-2 and scolymoside demonstrated anti-inflammatory functions by inhibiting hyperpermeability, expression of CAMs, and adhesion and migration of leukocytes. Each compound suppressed the production of TNF-α or IL-6 and the activation of NF-κB or ERK 1/2 by lipopolysaccharides. Reference: Inflamm Res. 2015 Dec;64(12):1005-21. https://pubmed.ncbi.nlm.nih.gov/26482935/

Preparing Stock Solutions

The following data is based on the product molecular weight 594.52 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. Lee IC, Bae JS. Anti-inflammatory effects of vicenin-2 and scolymoside on polyphosphate-mediated vascular inflammatory responses. Inflamm Res. 2016 Mar;65(3):203-12. doi: 10.1007/s00011-015-0906-x. Epub 2015 Nov 30. PMID: 26621502. 2. Yoon EK, Ku SK, Lee W, Kwak S, Kang H, Jung B, Bae JS. Antitcoagulant and antiplatelet activities of scolymoside. BMB Rep. 2015 Oct;48(10):577-82. doi: 10.5483/bmbrep.2015.48.10.044. PMID: 25887749; PMCID: PMC4911185. 3. Lee IC, Bae JS. Hepatoprotective effects of vicenin-2 and scolymoside through the modulation of inflammatory pathways. J Nat Med. 2020 Jan;74(1):90-97. doi: 10.1007/s11418-019-01348-x. Epub 2019 Jul 26. PMID: 31350693. 4. Kang H, Ku SK, Jung B, Bae JS. Anti-inflammatory effects of vicenin-2 and scolymoside in vitro and in vivo. Inflamm Res. 2015 Dec;64(12):1005-21. doi: 10.1007/s00011-015-0886-x. PMID: 26482935.

In vitro protocol:

In vivo protocol:

1. Lee IC, Bae JS. Hepatoprotective effects of vicenin-2 and scolymoside through the modulation of inflammatory pathways. J Nat Med. 2020 Jan;74(1):90-97. doi: 10.1007/s11418-019-01348-x. Epub 2019 Jul 26. PMID: 31350693. 2. Kang H, Ku SK, Jung B, Bae JS. Anti-inflammatory effects of vicenin-2 and scolymoside in vitro and in vivo. Inflamm Res. 2015 Dec;64(12):1005-21. doi: 10.1007/s00011-015-0886-x. PMID: 26482935.

1: Lee IC, Bae JS. Hepatoprotective effects of vicenin-2 and scolymoside through the modulation of inflammatory pathways. J Nat Med. 2020 Jan;74(1):90-97. doi: 10.1007/s11418-019-01348-x. Epub 2019 Jul 26. PMID: 31350693.

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