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JP-2026076348-A - Collagen production promoter

JP2026076348AJP 2026076348 AJP2026076348 AJP 2026076348AJP-2026076348-A

Abstract

[Problem] The objective is to provide a collagen production promoter that can efficiently promote collagen production. [Solution] A collagen production promoter containing a 3-hydroxypyridinium derivative represented by the following general formula (1) as an active ingredient. In the formula, A1 independently represents a hydroxyl group, a C1-C10 alkoxy group, a peptide structure having 1-100 amino acids bonded at the N-terminus, a hydrogen atom, an amino group, or a C1-C10 hydrocarbon group, and A2 independently represents a hydrogen atom, a C1-C10 hydrocarbon group, an acyl group, or a peptide structure having 1-100 amino acids bonded at the C-terminus. [Selection Diagram] None

Inventors

  • 渡辺 寛人
  • 早瀬 文孝

Assignees

  • 学校法人明治大学

Dates

Publication Date
20260511
Application Date
20260218
Priority Date
20170719

Claims (10)

  1. A collagen production promoter containing a 3-hydroxypyridinium derivative represented by the following general formula (1) as an active ingredient. (In formula (1), A1 is independently a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, a peptide structure having 1 to 100 amino acids bonded at the N-terminus, a hydrogen atom, an amino group (-NR 4 2 ), or a hydrocarbon group having 1 to 10 carbon atoms; A2 is independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, an acyl group (-COR 5 ), or a peptide structure having 1 to 100 amino acids bonded at the C-terminus; R is independently a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms; R1 is independently a single bond or a divalent hydrocarbon group having 1 to 10 carbon atoms which may have at least one functional group selected from the group consisting of a hydroxyl group, an amino group (-NR 4 2 ), and an oxa group (-O-); R2 is independently a hydroxyl group, a carboxyl group, and an amino group (-NR 4 2) R3 represents a hydrocarbon group having 1 to 10 carbon atoms, which may have at least one functional group selected from the group consisting of (1) and ( 2 ), R4 represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, which may have at least one functional group selected from the group consisting of a hydroxyl group, a carboxyl group and an amino group ( -NR42 ) , R5 represents a hydrocarbon group having 1 to 10 carbon atoms, and m and n each independently represent an integer from 0 to 4. However, m and n are numerical values such that m + n is an integer from 0 to 4. (In formula (2), A1 is independently a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, a peptide structure having 1 to 100 amino acids bonded at the N-terminus, a hydrogen atom, an amino group (-NR 4 2 ), or a hydrocarbon group having 1 to 10 carbon atoms, A2 is independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, an acyl group (-COR 5 ), or a peptide structure having 1 to 100 amino acids bonded at the C-terminus, R is independently a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, R4 is independently a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, R5 is independently a hydrocarbon group having 1 to 10 carbon atoms, R6 is a single bond, or a hydroxyl group and an amino group (-NR 4 2 ) This represents a divalent hydrocarbon group having 1 to 10 carbon atoms, which may have at least one functional group selected from the group consisting of the following:
  2. The collagen production promoter according to claim 1, characterized in that it contains 0.00001% by weight or more of the 3-hydroxypyridinium derivative as an active ingredient.
  3. The collagen production promoter according to claim 1 or 2, characterized in that the 3-hydroxypyridinium derivative is derived from a natural product.
  4. A cosmetic composition comprising a collagen production promoter according to any one of claims 1 to 3.
  5. A food or beverage composition containing a collagen production promoter according to any one of claims 1 to 3.
  6. A cell culture composition comprising a collagen production promoter according to any one of claims 1 to 3.
  7. A wound healing pharmaceutical composition comprising a collagen production promoter according to any one of claims 1 to 3.
  8. A composition for promoting bone formation, comprising a collagen production promoter according to any one of claims 1 to 3.
  9. A collagen hydrolysate characterized by containing 0.015% by weight or more of a 3-hydroxypyridinium substructure represented by the following general formula (3).
  10. A collagen hydrolysate characterized by containing 0.07% by weight or more of 3-hydroxypyridinoline represented by the following general formula (4).

Description

This invention relates to a collagen production promoter, and to cosmetic compositions, food and beverage compositions, cell culture compositions, wound healing pharmaceutical compositions, and bone formation promoting compositions containing the collagen production promoter. Collagen is present in all multicellular animals and is the most abundant protein in vertebrates, existing extracellularly. It is known to act as a major component in resisting strain forces in connective tissues such as bones, teeth, cartilage, tendons, ligaments, skin, and blood vessels, forming highly tensile insoluble fibers. Furthermore, while it is known that collagen consists of three polypeptide chains, with each peptide chain being cross-linked by a compound having a 3-hydroxypyridinium structure, there have been no reports whatsoever of its degradation products, 3-hydroxypyridinium derivatives, exhibiting physiological effects via receptors. Furthermore, collagen is an important component for skin elasticity and moisturizing function, and a decrease in collagen levels is known to cause a decline in skin firmness and elasticity, as well as the manifestation of aging-like symptoms such as rough skin and wrinkles. Therefore, research has been conducted on food ingredients, cosmetic ingredients, and pharmaceutical compositions that increase the amount of collagen in the skin, with the aim of maintaining skin health or suppressing skin aging. On the other hand, bone metabolism is normally maintained by a balance between the activity of osteoclasts, which break down old bone, and osteoblasts, which create new bone. It is known that calcium phosphate is deposited around type I collagen fibers secreted by osteoblasts, forming hydroxyapatite, which then contributes to bone formation. In recent years, with the aging population and the increase in underlying diseases such as diabetes, there has been a growing trend of patients with various bone diseases caused by decreased bone mass and bone quality, such as fractures and osteoporosis. As mentioned above, bone mass and bone quality are maintained in healthy individuals by a balance between bone resorption (bone breakdown) and bone formation. However, it is known that bone resorption becomes dominant due to factors such as aging and decreased hormone secretion due to menopause, leading to brittle bones. In response to this, treatments such as administering oral calcium preparations, vitamin D3 preparations, and parathyroid hormone preparations to suppress the activity of osteoclasts are commonly performed. Regarding collagen production promoters, for example, Patent Document 1 describes compounds represented by 1-acetoxy-1-(2,4-diacetoxyphenyl)-2-propene. Patent Document 2 describes an anti-aging topical skin preparation characterized by containing a synthetic peptide or derivative thereof composed of 3 to 8 amino acids and hydrolyzed collagen or a derivative thereof having a molecular weight in the range of 500 to 5000. Furthermore, pyridinoline, a representative compound of the present invention, is a known collagen-degrading component, as described in Non-Patent Document 1, and is used as a diagnostic agent for osteoporosis, as described in Patent Documents 3 and 4. Japanese Patent Publication No. 2009-79004Japanese Patent Publication No. 2011-042613Special Publication No. 05-502942Japanese Patent Application Publication No. 05-209870 Daisaburo Fujimoto, Takahiko Moriguchi, Torao Ishida, and Hiroshi Hayashi:‘The structure of pyridinoline, a collagen crosslink.’Biochem. Biophysics. Res. Commun. 84, 52-57 (1978). Purity testing of purified PYR by reverse-phase HPLCStructural identification of PYR by mass spectral analysisResults of RNA expression analysis of type I collagen type A in human tubular epithelial cellsResults of RNA expression level analysis of type I collagen A in TGFβ1Data showing the osteoblast differentiation-promoting effect of CHHPRT-PCR data on the effect of CHHP on promoting osteoblast collagen production. In describing the details of this invention, specific examples will be given, but the invention is not limited to the following, and can be modified as appropriate, without departing from the spirit of the invention. [Collagen production promoter] The collagen production promoter of the present invention is characterized by containing a 3-hydroxypyridinium derivative represented by the following general formula (1) as an active ingredient. (In formula (1), A1 is independently a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, a peptide structure having 1 to 100 amino acids bonded at the N-terminus, a hydrogen atom, an amino group (-NR 4 2 ), or a hydrocarbon group having 1 to 10 carbon atoms; A2 is independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, an acyl group (-COR 5 ), or a peptide structure having 1 to 100 amino acids bonded at the C-terminus; R is independently a hydrogen atom or a hydrocarbon group having 1 to 10 car