Concise Synthesis of Catechin Metabolites 5-(3′,4′-Dihydroxyphenyl)-γ-valerolactones (DHPV) in Optically Pure Form and Their Stereochemical Effects on Skin Wrinkle-Reducing Activities

Hur, Joonseong; Kim, Aram; Kim, Hyun Su; Lim, Changjin; Kim, Taewoo; Kim, Tae-Aug; Sim, Jaehoon; Suh, Young‐Ger

doi:10.3390/molecules25081970

Cited by 4 publications

(6 citation statements)

References 29 publications

(35 reference statements)

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“…These results indicated that (S)-DHPV can protect against LPS-induced inflammation by inhibiting NF-κB activation through repression of IκBα degradation. The enantiomeric purities of asymmetric dihydroxylation products, 2a and 2b, and final (S)-and (R)-DHPV, 1a and 1b, were confirmed by the analytical chiral HPLC experiment (Supplementary Materials), according to previous report of Suh group [23]. The synthetic final enantiomers were pure enough for further biological study, with the enantioselectivity of 97.3:2.7 for 1a and 95.1:4.9 for 1b.…”

Section: Anti-inflammatory Activity Of (R)-and (S)-dhpv On Iec-6 Cellssupporting

confidence: 58%

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Efficient and Divergent Enantioselective Syntheses of DHPVs and Anti-Inflammatory Effect on IEC-6 Cells

et al. 2020

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Despite numerous reports on the beneficial effects of catechin or epicatechin contained in tea and cacao extract on human health, a conclusive and precise molecular mechanism has not been elucidated. Metabolism of chemical compounds in gut microbiota recently gained significant attention, and extensive studies have been devoted in this field. In conjunction with these results, our group focused on the anti-inflammatory effects of both enantiomers of DHPV (5-(3′,4′-dihydroxyphenyl)-γ-valerolactone), produced in the intestine by microbiota metabolism, on IEC-6 cells. Divergent and efficient enantioselective synthesis of (S)- and (R)-DHPV was efficiently achieved by cross-metathesis and Sharpless asymmetric dihydroxylation as a key reaction for four steps in 16% and 14% overall yields, respectively. The anti-inflammatory effects of two enantiomers were tested on IEC-6 cells, and we found that (S)-DHPV was more active than (R)-DHPV. This result implicates that the metabolite produced in the gut has beneficial effects on IEC-6 cells of rat intestines, and the chirality of the metabolite is important for its anti-inflammatory activity. This also provided information for the future discovery of novel small molecular therapeutics for the treatment of inflammatory bowel disease.

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Section: Anti-inflammatory Activity Of (R)-and (S)-dhpv On Iec-6 Cellssupporting

confidence: 58%

“…25, x FOR PEER REVIEW 4 of 9Materials), according to previous report of Suh group[23]. The synthetic final enantiomers were pure enough for further biological study, with the enantioselectivity of 97.3:2.7 for 1a and 95.1:4.9 for 1b Divergent and enantioselective synthesis of DHPV.…”

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confidence: 97%

Efficient and Divergent Enantioselective Syntheses of DHPVs and Anti-Inflammatory Effect on IEC-6 Cells

et al. 2020

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“…These results imply that they might make good lead compounds for anti-inflammatory medications. 50 Two enantiomers of DHPV, a flavanol synthesized in the gastrointestinal tract by intestinal microbes' metabolic processes and present in nutritional plants, particularly green tea, red wine, and cocoa extracts, [118] were studied for their antiinflammatory properties on IEC-6 cells. The metabolite formed in the gut has positive effects on the IEC-6 cells of the rat intestine, as evidenced by the researchers' finding that (S)-DHPV was more active than (R)-DHPV.…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%

Enantioselective Synthesis of Flavonoids and Their Diverse Applications in Nutrition, Health, and Medicine: A Mini Review

Qayyum,

Shahid,

Mansoor

et al. 2024

ChemistrySelect

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Enantioselective synthesis, which yields one enantiomer in higher concentration or purity than the other, has transformed the production of flavonoids. Flavonoids, which are found in large quantities in nature and are known to exhibit a diverse array of physiological activities, are an ideal choice for enantioselective synthesis due to the significance of chirality in their therapeutic effects. Enantioselective synthesis is used in the medicinal, nutraceutical, and agrochemical sectors to produce flavonoids, which are useful in the development of novel therapeutics with improved effectiveness and fewer adverse reactions. The ability to obtain specific enantiomers of flavonoids facilitates the elucidation of biochemical strategies and the relationship between structure and activity, thereby providing avenues for tailored drug design and optimization. This review highlights the critical role that enantioselective synthesis plays in achieving the full potential of flavonoids for a variety of therapeutic and non‐therapeutic applications. It also discusses the challenges and prospects of enantioselective syntheses to create relevant classes of flavonoid monomers, emphasizing their applications in the field. The review focused on the synthetic methods for fabricating native flavonoids and their analogs, highlighting the critical role that enantioselective synthesis of flavonoids plays in maximizing their therapeutic potential for enhancing human health and wellbeing.

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“…3 S ‐Flavanols yield 4 S‐ C 6 –C 5 metabolites and 3 R ‐flavanols yield 4 R ‐C 6 –C 5 metabolites. [ 90 ]…”

Section: Reporting Of Enantiomers and Diastereo‐isomersmentioning

confidence: 99%

LC–MS Characterization and Quantification of Known and Unknown (Poly)phenol Metabolites—Possible Pitfalls and Their Avoidance

Clifford

Kuhnert

2022

Molecular Nutrition Food Res

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This review focuses on the LC–MS characterization and quantification of dietary (poly)phenols and their metabolites. It draws attention to errors, omissions, and misunderstandings that appear frequently in published papers, and suggests strategies for their avoidance. Aspects covered include the use of authentic standards and surrogate reference materials, the importance of collecting and archiving Total Ion Current MS data, the limitations of using on‐line compilations of accurate mass MS data to assign unknown components when multiple isomers are possible, and the often understated magnitude of person‐to‐person variation that may significantly impact at population level any potential health benefit.

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Concise Synthesis of Catechin Metabolites 5-(3′,4′-Dihydroxyphenyl)-γ-valerolactones (DHPV) in Optically Pure Form and Their Stereochemical Effects on Skin Wrinkle-Reducing Activities

Cited by 4 publications

References 29 publications

Efficient and Divergent Enantioselective Syntheses of DHPVs and Anti-Inflammatory Effect on IEC-6 Cells

Efficient and Divergent Enantioselective Syntheses of DHPVs and Anti-Inflammatory Effect on IEC-6 Cells

Enantioselective Synthesis of Flavonoids and Their Diverse Applications in Nutrition, Health, and Medicine: A Mini Review

LC–MS Characterization and Quantification of Known and Unknown (Poly)phenol Metabolites—Possible Pitfalls and Their Avoidance

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