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Luteolin 7-O-glucuronide

$300

  • Brand : BIOFRON

  • Catalogue Number : BF-L4011

  • Specification : 98%(HPLC)

  • CAS number : 29741-10-4

  • Formula : C21H18O12

  • Molecular Weight : 462.36

  • PUBCHEM ID : 5280601

  • Volume : 25mg

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Catalogue Number

BF-L4011

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

462.36

Appearance

Yellow crystalline powder

Botanical Source

Chrysanthemum morifolium,Agrimonia pilosa,Callicarpa macrophylla

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

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

Synonyms

(2S,3S,4S,5R)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid/luteolin 7-O-beta-D-glucosiduronic acid/Luteolin-7-glucuronide/2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl β-D-glucopyranosiduronic acid/4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(β-D-glucopyranuronosyloxy)-5-hydroxy-/Luteolin 7-O-glucuronide

IUPAC Name

(2S,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid

Density

1.8±0.1 g/cm3

Solubility

Methanol

Flash Point

315.2±27.8 °C

Boiling Point

892.5±65.0 °C at 760 mmHg

Melting Point

242-244℃

InChl

InChI=1S/C21H18O12/c22-9-2-1-7(3-10(9)23)13-6-12(25)15-11(24)4-8(5-14(15)32-13)31-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-24,26-28H,(H,29,30)/t16-,17-,18+,19-,21?/m0/s1

InChl Key

VSUOKLTVXQRUSG-DAZJWRSOSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:29741-10-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31484378

Abstract

Antialgal compounds from plants have been identified as promising candidates for controlling harmful algal blooms (HABs). In our previous study, luteolin-7-O-glucuronide was used as a promising algistatic agent to control Phaeocystis globosa (P. globose) blooms; however, its antialgal mechanism on P. globosa have not yet been elaborated in detail. In this study, a liquid chromatography linked to tandem mass spectrometry (LC-MS/MS)-based untargeted metabolomic approach was used to investigate changes in intracellular and extracellular metabolites of P. globosa after exposure to luteolin-7-O-glucuronide. Significant differences in intracellular metabolites profiles were observed between treated and untreated groups; nevertheless, metabolic statuses for extracellular metabolites were similar among these two groups. For intracellular metabolites, 20 identified metabolites showed significant difference. The contents of luteolin, gallic acid, betaine and three fatty acids were increased, while the contents of α-Ketoglutarate and acetyl-CoA involved in tricarboxylic acid cycle, glutamate, and 11 organic acids were decreased. Changes in those metabolites may be induced by the antialgal compound in response to stress. The results revealed that luteolin played a vital role in the antialgal mechanism of luteolin-7-O-glucuronide on P. globosa, because luteolin increased the most in the treatment groups and had strong antialgal activity on P. globosa. α-Ketoglutarate and acetyl-CoA were the most inhibited metabolites, indicating that the antialgal compound inhibited the growth through disturbed the tricarboxylic acid (TCA) cycle of algal cells. To summarize, our data provides insights into the antialgal mechanism of luteolin-7-O-glucuronide on P. globosa, which can be used to further control P. globosa blooms.

KEYWORDS

Phaeocystis globosa; luteolin-7-O-glucuronide; metabolomic analysis.

Title

The Antialgal Mechanism of Luteolin-7-O-Glucuronide on Phaeocystis globosa by Metabolomics Analysis

Author

Jingyi Zhu 1 , Yeyin Yang 1 , Shunshan Duan 2 , Dong Sun 3

Publish date

2019 Sep 3

PMID

31340457

Abstract

Enhalus acoroides (E. acoroides) is one of the most common species in seagrass meadows. Based on the application of allelochemicals from aquatic plants to inhibit harmful algal blooms (HABs), we used E. acoroides aqueous extract against harmful algae species Phaeocystis globosa (P. globosa). The results showed that E. acoroides aqueous extract could significantly inhibited the growth of P. globosa, decrease the chlorophyll-a content and photosynthetic efficiency (Fv/Fm) values of P. globosa, followed by vacuolization, plasmolysis, and the destruction of organelles. Twelve types of major chemical constituents were identified in E. acoroides aqueous extracts by ultraperformance liquid chromatography-high resolution mass spectrometry (UPLC-HRMS), including six flavonoids, two homocyclic peptides, two long-chain aliphatic amides, one tannin, and one nitrogen heterocyclic compound. Flavonoids were the characteristic chemical constituents of E. acoroides aqueous extract. Furthermore, the antialgal activity of luteolin-7-O-glucuronide (68.125 μg/mL in 8 g/L E. acoroides aqueous extract) was assessed. The EC50-96 h value was 34.29 μg/mL. In conclusion, the results revealed that luteolin 7-O-glucuronide was one of the antialgal compounds of E. acoroides aqueous extract, with potential application as novel algaecide.

KEYWORDS

Phaeocystis globosa; luteolin-7-O-glucuronide; metabolomic analysis.

Title

Growth Inhibition of Phaeocystis Globosa Induced by Luteolin-7-O-glucuronide From Seagrass Enhalus Acoroides

Author

Jingyi Zhu 1 , Han Xiao 1 , Qi Chen 1 , Min Zhao 1 , Dong Sun 2 , Shunshan Duan 3

Publish date

2019 Jul 23

PMID

32187984

Abstract

Various herbal extracts containing luteolin-7-O-glucuronide (L7Gn) have been traditionally used to treat inflammatory diseases. However, systemic studies aimed at elucidating the anti-inflammatory and anti-oxidative mechanisms of L7Gn in macrophages are insufficient. Herein, the anti-inflammatory and anti-oxidative effects of L7Gn and their underlying mechanisms of action in macrophages were explored. L7Gn inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages by transcriptional regulation of inducible NO synthase (iNOS) in a dose-dependent manner. The mRNA expression of inflammatory mediators, including cyclooxygenase-2 (COX-2), interleukin-6 (IL-6), IL-1β, and tumor necrosis factor-α (TNF-α), was inhibited by L7Gn treatment. This suppression was mediated through transforming growth factor beta-activated kinase 1 (TAK1) inhibition that leads to reduced activation of nuclear factor-κB (NF-κB), p38, and c-Jun N-terminal kinase (JNK). L7Gn also enhanced the radical scavenging effect and increased the expression of anti-oxidative regulators, including heme oxygenase-1 (HO-1), glutamate-cysteine ligase catalytic subunit (GCLC), and NAD(P)H quinone oxidoreductase 1 (NQO1), by nuclear factor-erythroid 2 p45-related factor 2 (Nrf2) activation. These results indicate that L7Gn exhibits anti-inflammatory and anti-oxidative properties in LPS-stimulated murine macrophages, suggesting that L7Gn may be a suitable candidate to treat severe inflammation and oxidative stress.

KEYWORDS

RAW 264.7 macrophages; anti-inflammation; anti-oxidation; luteolin-7-O-glucuronide; nuclear factor-erythroid 2 p45-related factor 2; transforming growth factor beta-activated kinase 1.

Title

Anti-Inflammatory and Anti-Oxidative Effects of luteolin-7- O-glucuronide in LPS-Stimulated Murine Macrophages Through TAK1 Inhibition and Nrf2 Activation

Author

Young-Chang Cho 1 , Jiyoung Park 2 , Sayeon Cho 2

Publish date

2020 Mar 16


Description :

Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively.