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(+-)-Homoeriodictyol

$455

  • Brand : BIOFRON

  • Catalogue Number : AV-C10500

  • Specification : 98%

  • CAS number : 107657-60-3

  • Formula : C16H14O6

  • Molecular Weight : 302.28

  • PUBCHEM ID : 3512637

  • Volume : 10mg

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Catalogue Number

AV-C10500

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

302.28

Appearance

Botanical Source

Structure Type

Category

Standards;Natural Pytochemical;API

SMILES

COC1=C(C=CC(=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O)O

Synonyms

4'-methoxy-5,7,3'-trihydroxyflavanone/5,7,4'-trihydroxy-3'-methoxyflavanone/2-phenyl-2,3-dihydro-1H-quinolin-4-one/2-phenyl-1,2,3,4-tetrahydroquinolone/eriodictyol-3'-methyl ether/2-phenyl-1,2,3,4-tetrahydro-4-quinolone/4',5,7-trihydroxy-3'-methoxyflavanone

IUPAC Name

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one

Applications

Density

Solubility

Apoptosis; Homoeriodictyol; Mitochondrial dysfunction; Nrf2; Reactive oxygen stress

Flash Point

Boiling Point

Melting Point

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:107657-60-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

29902531

Abstract

Excess intracellular reactive oxygen species (ROS) production is a significant causative factor of many diseases, exemplified by vascular diseases. Mitochondria are a major source of endogenous ROS, which simultaneously induce mitochondrial dysfunction. Nuclear factor-erythroid 2-related factor 2 (Nrf2) represents an important intracellular defense system that protects cells against oxidative insults caused by ROS. Therefore, molecules with the capacities of inducing Nrf2, and preventing mitochondrial dysfunction can inhibit cell apoptosis, and thus are potential drug candidates for the therapy of ROS-mediated vascular diseases. Homoeriodictyol (HE), previously isolated from Viscum articulatum Burm, has been found to be an Nrf2 inducer. In the present study, we investigated its protection on ROS-induced endothelial cell injury using a H2O2-induced human umbilical vein EA.hy926 cell oxidative insult model. Our results indicated that HE activated Nrf2 signaling pathway and protected cells against H2O2-induced cell damage. HE alleviated H2O2-induced loss of mitochondrial membrane potential (MMP), blocked the releases of cytochrome C and apoptosis inducing factor (AIF) from mitochondria, and thus inhibited mitochondria-mediated cell apoptosis. Furthermore, HE inhibited H2O2-induced changes of apoptosis-related proteins, such as Bcl-2, Bcl-xL, caspases -3, -9 and PARP. Further study demonstrated that the protection of HE against H2O2-induced endothelial cell damage was Nrf2-dependent. Collectively, our observations suggest that HE is capable of counteracting oxidative insults in endothelial cells, and has a potential to be a therapeutic agent against ROS-mediated vascular diseases.

Copyright ? 2018 Elsevier Inc. All rights reserved.

KEYWORDS

Apoptosis; Homoeriodictyol; Mitochondrial dysfunction; Nrf2; Reactive oxygen stress

Title

Homoeriodictyol protects human endothelial cells against oxidative insults through activation of Nrf2 and inhibition of mitochondrial dysfunction.

Author

Shen T1, Li HZ1, Li AL1, Li YR1, Wang XN1, Ren DM2.

Publish date

2018 Oct

PMID

28834253

Abstract

SCOPE:
Anorexia of aging, characterized by a decrease in appetite and/or food intake, is a major risk factor of under-nutrition and adverse health outcomes in elderly people. Recent in vitro evidence suggests homoeriodictyol (HED), a naturally occurring, bitter-masking flavanone, as a promising agent to increase appetite and food intake.

METHODS AND RESULTS:
In two cross-over intervention trials, 30 mg NaHED, either solely (n = 10, Study I) or in combination with a 75 g glucose load (n = 17, study II) were administered to healthy adult subjects. Ratings of hunger were assessed at fasting and either 30 min (Study I) or 120 min (Study II) post intervention. Ad libitum energy intake from a standardized breakfast and plasma changes in hunger-/satiety-associated hormones PYY, GLP-1, ghrelin and serotonin were determined after blood drawings. Effects were more pronounced when NaHED was administered in combination with 75 g glucose since ad libitum energy (+ 9.52 ± 4.60%) and protein (+ 7.08 ± 7.97%) intake as well as plasma ΔAUC ghrelin values increased in study II solely, whereas plasma serotonin concentrations decreased after both interventions.

CONCLUSIONS:
NaHED demonstrated appetizing effects in healthy adults when administered with a glucose load. Long-term intervention studies are warranted to verify these effects in compromised subjects.

? 2017 The Authors. Published by WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KEYWORDS

appetizers; food intake; homoeriodictyol; peripheral serotonin; plasma ghrelin

Title

Appetite-Inducing Effects of Homoeriodictyol: Two Randomized, Cross-Over Interventions.

Author

Hochkogler CM1, Liszt K1, Lieder B2, Stoger V1, Stubler A1, Pignitter M2, Hans J3, Widder S3, Ley JP3, Krammer GE3, Somoza V1,2.

PMID

23906843

Abstract

In this work, we attempted to synthesize homoeriodictyol by transferring one methyl group of S-adenosyl-L-methionine (SAM) to eriodictyol using flavone 3′-O-methyltransferase ROMT-9, which was produced by recombinant Yarrowia lipolytica. Specifically, the ROMT-9 gene from rice was synthesized and cloned into the multi-copy integrative vector pINA1297, and was further expressed in Y. lipolytica with a growth phase-dependent constitutive promoter hp4d. The highest ROMT-9 activity reached 5.53 U/L after 4 days of culture in shake flask. The optimal pH and temperature of the purified ROMT-9 were 8.0 and 37 °C, respectively. The purified enzyme was stable up to 40 °C, and retained more than 80% of its maximal activity between pH 6.5 and 9.0. The recombinant ROMT-9 did not require Mg²? for catalysis, while was completely inhibited in the presence of 5 mM Zn²?, Cu²?, Ba²?, Al³?, or Ni²?. The purified ROMT-9 was used to synthesize homoeriodictyol, and the maximal transformation ratio reached 52.4% at 16 h under the following conditions: eriodictyol 0.2 g/L, ROMT-9 0.16 g/L, SAM 0.2 g/L, CH₃OH 6% (v/v), temperature 37 °C, and pH 8.0. This work provides an alternative strategy for efficient synthesis of homoeriodictyol and compared to the traditional plant extraction or chemical synthesis, the biotransformation approach generates less environmental pollution and has a great potential for the sustainable production of homoeriodictyol.

Copyright ? 2013 Elsevier B.V. All rights reserved.

KEYWORDS

Yarrowia lipolytica; Biotransformation; Flavone 3′-O-methyltransferase; Heterologous expression; Homoeriodictyol

Title

Biosynthesis of homoeriodictyol from eriodictyol by flavone 3'-O-methyltransferase from recombinant Yarrowia lioplytica: Heterologous expression, biochemical characterization, and optimal transformation.

Author

Liu Q1, Liu L, Zhou J, Shin HD, Chen RR, Madzak C, Li J, Du G, Chen J.

Publish date

2013 Sep 20