Name: Luteolin 7-O-glucoside
Brand: BOC Sciences
Price: 299 USD
Availability: MadeToOrder

Synonyms

2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl-D-glucopyranoside; Cynaroside; Luteoloside; Luteolin 7-glucoside

IUPAC Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Canonical SMILES

C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O)O

InChI

InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1

InChIKey

PEFNSGRTCBGNAN-QNDFHXLGSA-N

Density

1.7±0.1 g/cm3

Solubility

Soluble in dimethylsulfoxid, dimethylformamid, insoluble in ethanol and water

Melting Point

240 - 242°C

Flash Point

296.8±27.8 °C

Index Of Refraction

1.740

PSA

190.28000

Vapor Pressure

0.0±3.2 mmHg at 25°C

Appearance

Dark Yellow Solid

Quantity

Milligrams-Grams

Quality Standard

Enterprise Standard

Shipping

Room temperature

Storage

Hygroscopic, Refrigerator, under inert atmosphere

Boiling Point

838.10°C at 760 mmHg (est)

Form

Powder

In Vitro

Cynaroside inhibited the expression of iNOS, COX-2, TNF-α, and IL-6 in LPS-stimulated hPDL and RAW264.7 cells without cytotoxicity. Furthermore, cynaroside significantly suppressed LPS-induced protein expression of matrix metalloproteinase 3. Additionally, cynaroside prevented LPS-induced NF-κB p65 subunit translocation to the nucleus by inhibiting the phosphorylation and degradation of IκB-α. Moreover, cynaroside could restore the mineralization ability of hPDL cells reduced by LPS.

In Vivo

Building upon a sepsis mouse model, it was observed cynaroside alleviated serum levels of inflammatory factors including IL-1β and TNF-α at 5 and 10 mg/kg. The pathological injury of heart, kidney and lung was remarkedly attenuated as the levels of blood urea nitrogen, creatinine, creatine kinase-MB and lactate dehydrogenase were reduced nearly 2.8-, 2.7-, 2.4-, and 2.5-fold as compared with the sepsis mice, respectively. The research further demonstrated cynaroside suppressed the biomarker of pro-inflammatory macrophage M1 phenotype (iNOS+) and promotes the anti-inflammatory M2 polarization (CD206+) in the injury organs of septic mice. Mechanistic research verified cynaroside inhibited LPS-induced polarization of macrophage into M1 phenotype, which can be highly blocked by Nrf2 inhibitor. Expectedly, Nrf2 and its downstream (Heme oxygenase-1 (HO-1)) was upregulated in injury organs after treating with cynaroside, indicating the involvement of Nrf2 signaling.

Luteolin 7-O-glucoside is a flavonoid glycoside that can function as an ADC cytotoxin in antibody-drug conjugates. Its cytotoxic mechanism involves modulation of cellular signaling pathways, inhibition of proliferation, and induction of apoptosis in tumor cells. The glucoside moiety enhances solubility and enables efficient conjugation to antibodies via cleavable or non-cleavable linker chemistries, allowing targeted delivery of the payload.

In antibody-drug conjugates, Luteolin 7-O-glucoside is covalently attached to monoclonal antibodies using linker strategies designed for systemic stability and controlled intracellular release. The ADC remains inactive in circulation, reducing off-target effects, while enzymatic cleavage within tumor cells releases the active payload. This selective delivery ensures that cytotoxic effects occur specifically in antigen-expressing cells, maintaining precision in tumor-targeted therapy.

Applications of Luteolin 7-O-glucoside include its incorporation into ADCs targeting solid tumors and hematologic malignancies. Its chemical structure is compatible with a variety of linker systems, allowing optimization of conjugation efficiency, intracellular release kinetics, and pharmacokinetic properties. The compound exhibits reproducible cytotoxic activity in target-expressing cell lines and supports the design of ADCs with defined mechanisms of action and controlled antitumor effects.

1.Superheated liquid extraction of oleuropein and related biophenols from olive leaves.

Japón-Luján R;Luque de Castro MD J Chromatogr A. 2006 Dec 15;1136(2):185-91. Epub 2006 Oct 11.

Oleuropein and other healthy olive biophenols (OBPs) such as verbacoside, apigenin-7-glucoside and luteolin-7-glucoside have been extracted from olive leaves by using superheated liquids and a static-dynamic approach. Multivariate methodology has been used to carry out a detailed optimisation of the extraction. Under the optimal working conditions, complete removal without degradation of the target analytes was achieved in 13 min. The extract was injected into a chromatograph-photodiode array detector assembly for individual separation-quantification. The proposed approach - which provides more concentrated extracts than previous alternatives - is very useful to study matrix-extractant analytes partition. In addition, the efficacy of superheated liquids to extract OBPs, the simplicity of the experimental setup, its easy automation and low acquisition and maintenance costs make the industrial implementation of the proposed method advisable.

2.Dietary Exposure Risk Assessment of Flonicamid and Its Effect on Constituents after Application in Lonicerae Japonicae Flos.

Li J;Wang Y;Xue J;Wang P;Shi S Chem Pharm Bull (Tokyo). 2018 Jun 1;66(6):608-611. doi: 10.1248/cpb.c17-00985. Epub 2018 Mar 14.

To investigate the dietary exposure risk of flonicamid application on Lonicerae Japonicae Flos and the effect of flonicamid on constituents of Lonicerae Japonicae Flos, field experiments were conducted in Fengqiu, Henan province, and flonicamid residue in samples collected was detected by gas chromatography equipped with electron capture detector (GC-ECD). And chlorogenic acid and luteoloside were determined by HPLC. Dietary exposure risk assessment was conducted through comparing the estimated daily intake (EDI) which was calculated by using the consumed residual level along with the acceptable daily intake (ADI). The effect of flonicamid on chlorogenic acid and luteoloside were obtained by ANOVA statistical analysis and least significant difference (LSD)-t test. The results showed that the terminal-residue contents of flonicamid were under 1.6 mg kg;-1;. And risk quotient ranged from 0.0011 to 0.0028, indicating the long-term exposure to flonicamid residual through consumption of Lonicerae Japonicae Flos in consumers was relatively low. Flonicamid could suppress the generation of luteoloside, so it was not advised to be used in L. japonica flowering phase. The study aims at providing the useful suggestion on the reasonable flonicamid usage and the reference for the establishment of maximum residue limits (MRLs) of flonicamid in Lonicerae Japonicae Flos.

3.Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102.

Edenharder R;Grünhage D Mutat Res. 2003 Sep 9;540(1):1-18.

Mutagenicity induced by tert-butyl hydroperoxide (BHP) or cumene hydroperoxide (CHP) in Salmonella typhimurium TA102 was effectively reduced by flavonols with 3',4'-hydroxyl groups such as fisetin, quercetin, rutin, isoquercitrin, hyperoxide, myricetin, myricitrin, robinetin, and to a lesser extent also by morin and kaempferol (ID50=0.25-1.05 micromol per plate). With the exception of isorhamnetin, rhamnetin, morin, and kaempferol, closely similar results were obtained with both peroxides. Hydrogenation of the double bond between carbons 2 and 3 (dihydroquercetin, dihydrorobinetin) as well as the additional elimination of the carbonyl function at carbon 4 (catechins) resulted in a loss of antimutagenicity with the notable exception of catechin itself. Again, all flavones and flavanones tested were inactive except luteolin, luteolin-7-glucoside, diosmetin, and naringenin. The typical radical scavenger butylated hydroxytoluene also showed strong antimutagenicity against CHP (ID50=5.4 micromol per plate) and BHP (ID50=11.4 micromol per plate). Other lipophilic scavengers such as alpha-tocopherol and N,N'-diphenyl-1,4-phenylenediamine exerted only moderate effects, the hydrophilic scavenger trolox was inactive.

What is Luteolin 7-O-glucoside?

Luteolin 7-O-glucoside is a flavonoid glycoside with potential cytotoxic activity, often studied as a payload in ADC development. It can modulate cellular signaling and apoptosis pathways, making it suitable for selective delivery to target cells via antibody conjugation.

5/4/2018

Dear team, how does Luteolin 7-O-glucoside function in ADCs?

When used as an ADC payload, Luteolin 7-O-glucoside exerts its effects by interfering with key signaling and apoptotic mechanisms in targeted cancer cells. Conjugation to antibodies ensures selective delivery, reducing systemic toxicity and enhancing therapeutic index.

21/11/2020

Dear team, which linkers are compatible with Luteolin 7-O-glucoside?

Luteolin 7-O-glucoside can be conjugated using cleavable linkers such as peptide-based or chemically sensitive linkers. Proper linker selection enables controlled intracellular release and maintains stability of the ADC in systemic circulation.

9/3/2019

Could you please let me know if Luteolin 7-O-glucoside can be used in preclinical ADC studies?

Yes, Luteolin 7-O-glucoside is commonly used in preclinical ADC research to evaluate cytotoxicity, efficacy, and pharmacokinetics. These studies help optimize payload delivery and ADC design for potential clinical applications.

7/1/2021

Good afternoon! What safety precautions are recommended when handling Luteolin 7-O-glucoside?

Handling Luteolin 7-O-glucoside requires strict laboratory safety protocols, including personal protective equipment, containment measures, and proper waste management to prevent exposure to its cytotoxic effects during conjugation and research.

5/12/2016

— Dr. Peter Hall, Senior Scientist (USA)

Luteolin 7-O-glucoside delivered by BOC Sciences showed excellent purity and stability.

9/3/2019

— Dr. Thomas White, Research Director (USA)

Luteolin 7-O-glucoside was delivered with outstanding quality, helping us evaluate its role in novel linker systems.

5/12/2016

— Ms. Anna Müller, Senior Scientist (Germany)

The team at BOC Sciences provided detailed analytical data for Luteolin 7-O-glucoside, which gave us confidence in the results.

7/1/2021

— Dr. Patrick Lewis, Laboratory Head (UK)

We tested Luteolin 7-O-glucoside in conjugation studies, and its performance was consistent across multiple trials.