Deuterated proanthocyanidin metabolite 5-(3 ',4 '-dihydroxyphenyl)-gamma-valerolactone has been successfully produced. This metabolite is responsible for several proanthocyanidin protective effects in the field of cancer chemoprevention, skin wrinkle-prevention, and antimicrobials. The synthetic approach applied employs a short reaction sequence and allows the incorporation of four deuterium atoms on non-exchangeable sites, making it an attractive strategy to produce a stable isotopically labeled internal standard for quantitative mass spectrometry isotope dilution-based methods, as demonstrated by developing an LC-MS/MS method to quantify DHPV in urine samples. Overall, this efficient synthesis provides a valuable analytical tool for the study of the metabolic conversion of proanthocyanidins thus helping to investigate the biological effect and establishing the active dose of the key catabolite 5-(3 ',4 '-dihydroxyphenyl)-gamma-valerolactone.Deuterated proanthocyanidin metabolite 5-(3 ',4 '-dihydroxyphenyl)-gamma-valerolactone has been successfully produced.

Concise synthesis of deuterium-labelled proanthocyanidin metabolite 5-(3′,4′-dihydroxyphenyl)-γ-valerolactone as an analytical tool / A. Artasensi, S. Mazzotta, G. Baron, G. Aldini, L. Fumagalli. - In: RSC ADVANCES. - ISSN 2046-2069. - 14:9(2024 Feb 14), pp. 6410-6415. [10.1039/d3ra08665h]

Concise synthesis of deuterium-labelled proanthocyanidin metabolite 5-(3′,4′-dihydroxyphenyl)-γ-valerolactone as an analytical tool

A. Artasensi
Co-primo
;
S. Mazzotta
Co-primo
;
G. Baron
Secondo
;
G. Aldini
Penultimo
;
L. Fumagalli
Ultimo
2024

Abstract

Deuterated proanthocyanidin metabolite 5-(3 ',4 '-dihydroxyphenyl)-gamma-valerolactone has been successfully produced. This metabolite is responsible for several proanthocyanidin protective effects in the field of cancer chemoprevention, skin wrinkle-prevention, and antimicrobials. The synthetic approach applied employs a short reaction sequence and allows the incorporation of four deuterium atoms on non-exchangeable sites, making it an attractive strategy to produce a stable isotopically labeled internal standard for quantitative mass spectrometry isotope dilution-based methods, as demonstrated by developing an LC-MS/MS method to quantify DHPV in urine samples. Overall, this efficient synthesis provides a valuable analytical tool for the study of the metabolic conversion of proanthocyanidins thus helping to investigate the biological effect and establishing the active dose of the key catabolite 5-(3 ',4 '-dihydroxyphenyl)-gamma-valerolactone.Deuterated proanthocyanidin metabolite 5-(3 ',4 '-dihydroxyphenyl)-gamma-valerolactone has been successfully produced.
Settore CHIM/06 - Chimica Organica
   MIND FoodS HUB
   REGIONE LOMBARDIA
14-feb-2024
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/1058968
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