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Homovanillyl alcohol (HVA), hva isomer, methods of making compositions comprising such compounds, and methods using such compounds

A technique for homovanillyl alcohol, isomers, for use in maintaining or improving bone and/or cartilage health, homovanillyl alcohol and its previously unidentified isomer 3-hydroxy-4-methoxyphenethyl alcohol, containing olive Field of composition of picroside metabolites

Pending Publication Date: 2020-06-26
SOC DES PROD NESTLE SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Furthermore, the use of these drugs is often associated with side effects such as gastrointestinal or cardiovascular risks

Method used

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  • Homovanillyl alcohol (HVA), hva isomer, methods of making compositions comprising such compounds, and methods using such compounds
  • Homovanillyl alcohol (HVA), hva isomer, methods of making compositions comprising such compounds, and methods using such compounds
  • Homovanillyl alcohol (HVA), hva isomer, methods of making compositions comprising such compounds, and methods using such compounds

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Embodiment approach

[0096] One aspect of the present disclosure is a composition comprising homovanillyl alcohol and / or isomers of homovanillyl alcohol. In one embodiment, homovanillyl alcohol and / or at least a portion of the isomers of homovanillyl alcohol may be obtained by chemical synthesis, for example by catechol-O-transmethylation on any hydroxyl group of hydroxytyrosol An enzyme (COMT) that subjects hydroxytyrosol to methylation of the catechol moiety (either at the 3-OH or 4-OH of the benzene ring).

[0097] Additionally or alternatively, homovanillyl alcohol and / or at least a portion of homovanillyl alcohol isomers may be obtained by extraction. For example, homovanillyl alcohol and / or at least a part of homovanillyl alcohol isomers can be obtained by extracting from plants such as Oleaceae, preferably stems, leaves, fruits or stones of plants belonging to Oleaceae such as Oleaceae (olive tree) one or more of them.

[0098] In one embodiment, the composition comprises a plant extract ...

Embodiment 1

[0136] Example 1: Validated methods for the quantification of oleuropein metabolites hydroxytyrosol, homovanillyl alcohol and new identifications in urine LC-MS method for the defined homovanillyl alcohol isomers

[0137] overview

[0138]Oleuropein (OE) is the main phenolic compound of the olive tree (Olectus oleifera) and is present in relatively high amounts in raw olive fruit and leaves. The metabolism of olive leaf extract was studied by identifying its metabolites in urine after ingestion. The LC-MS method was developed and targeted for hydroxytyrosol, homovanillyl alcohol, and the homovanillyl isomer 3-hydroxy-4-methoxyphenethyl alcohol (alternatively known as 3-hydroxy-4-methoxyphenethyl alcohol It has been fully validated by the quantification of base alcohols, which is the first time that it has been identified.

[0139] Specifically, urine samples were enzymatically treated to hydrolyze the glucuronide and sulfate moieties and release quantified amounts of t...

Embodiment 2

[0217] Example 2: Chondrocyte Data

[0218] Chondrocytes in alginate microbeads were subjected to a two-hour polyphenol pretreatment followed by a twenty-four-hour IL1-α stimulation. The results are shown in Figures 16A-16C , which showed that oleuropein metabolites prevent inflammation-induced catabolism.

[0219] about Figure 16A , an anabolic-related gene for collagen II, a major structural component of the joint extracellular matrix. The data on this gene showed a tendency for polyphenols to have a protective effect at 10 μM. The isomer of homovanillyl alcohol, 3-hydroxy-4-methoxyphenethyl alcohol (or alternatively 3-hydroxy-4-methoxyphenethyl alcohol), had a pronounced effect ("isoHVOH").

[0220] about Figure 16B and Figure 16C , matrix metalloproteinases (eg, MMP-3 and MMP-13) are associated with collagen degradation and joint inflammation. With the exception of hydroxytyrosol, each polyphenol tested was protective at 10 μM.

[0221] The anti-inflammatory ...

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Abstract

A composition contains at least one of homovanillyl alcohol (HVA) or its previously unidentified isomer (isoHVA). Additionally or alternatively, the composition contains a precursor of HVA and / or isoHVA (e.g., hydroxytyrosol, oleuropein aglycone, oleuropein, demethyloleuropein, oleuroside, verbascoside or mixtures thereof) and also contains at least one probiotic and / or at least one enzyme which convert the precursor to HVA and / or isoHVA in vivo (and / or an intermediate compound then subjected to methylation in vivo to form HVA and / or isoHVA). The composition can be administered to an individual to treat or reduce incidence of impaired mobility in an older adult; stimulate bone formation and / or inhibit bone resorption; treat or reduce incidence of synovitis in an individual in need or at risk thereof; treat or reduce incidence of articular cartilage degradation subsequent to synovitis in an individual having or recovering from synovitis; or treat or reduce incidence of cartilage breakdown.

Description

Background technique [0001] The present disclosure relates generally to oleuropein metabolites and also to compositions comprising oleuropein metabolites, and also to maintaining or improving bone and / or cartilage health. Additionally or alternatively, the composition prevents, alleviates and / or treats bone and / or cartilage disorders. More specifically, the present disclosure relates to homovanillyl alcohol (HVA) and its previously unidentified isomer 3-hydroxy-4-methoxyphenethyl alcohol (which may alternatively be referred to as 3-hydroxy-4-methoxy phenylethyl alcohol). For example, an oral composition may comprise HVA isomers. [0002] Bone mass evolves throughout life and is regulated by genetic, mechanical and hormonal mechanisms. Bone mineral collection occurs during childhood and peak bone mass is achieved around the age of twenty. During this period, bone formation exceeds bone resorption. Later in life, and especially in menopausal or elderly populations, bone mas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/7048A61K36/63A23L33/135C12Q1/6809A61K35/741C12Q1/689A61K31/7042A61P19/00
CPCA61K45/06A61K31/085A61K31/7042C12Q1/689A61K2236/00A61P19/00A61K36/63A61K2300/00A23L33/105A23L33/135A23L33/40A23V2002/00A61K35/741A61K38/465A61K38/47C12P7/22
Inventor M·N·奥卡亚达L·波盖
Owner SOC DES PROD NESTLE SA
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