Sustainable methods for the carboxymethylation and methylation of ursolic acid with dimethyl carbonate under mild and acidic conditions.


Journal

RSC advances
ISSN: 2046-2069
Titre abrégé: RSC Adv
Pays: England
ID NLM: 101581657

Informations de publication

Date de publication:
22 May 2024
Historique:
received: 20 03 2024
accepted: 07 05 2024
medline: 27 5 2024
pubmed: 27 5 2024
entrez: 27 5 2024
Statut: epublish

Résumé

Ursolic acid is a triterpene plant extract that exhibits significant potential as an anti-cancer, anti-tumour, and anti-inflammatory agent. Its direct use in the pharmaceutical industry is hampered by poor uptake of ursolic acid in the human body coupled with rapid metabolism causing a decrease in bioactivity. Modification of ursolic acid can overcome such issues, however, use of toxic reagents, unsustainable synthetic routes and poor reaction metrics have limited its potential. Herein, we demonstrate the first reported carboxymethylation and/or methylation of ursolic acid with dimethyl carbonate (DMC) as a green solvent and sustainable reagent under acidic conditions. The reaction of DMC with ursolic acid, in the presence of PTSA, ZnCl

Identifiants

pubmed: 38799212
doi: 10.1039/d4ra02122c
pii: d4ra02122c
pmc: PMC11124730
doi:

Types de publication

Journal Article

Langues

eng

Pagination

16921-16934

Informations de copyright

This journal is © The Royal Society of Chemistry.

Déclaration de conflit d'intérêts

There are no conflicts to declare.

Auteurs

Nuttapong Kadsanit (N)

Materials Chemistry Research Center (MCRC), Department of Chemistry and Centre of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University Khon Kaen 40002 Thailand andrew@kku.ac.th.

Pattamabhorn Worsawat (P)

Materials Chemistry Research Center (MCRC), Department of Chemistry and Centre of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University Khon Kaen 40002 Thailand andrew@kku.ac.th.

Chadamas Sakonsinsiri (C)

Department of Biochemistry, Faculty of Medicine, Khon Kaen University Khon Kaen 40002 Thailand.

Con R McElroy (CR)

School of Chemistry, University of Lincoln Brayford Pool Campus Lincoln LN6 7TS UK.
Green Chemistry Centre of Excellence, Department of Chemistry, University of York Heslington York YO10 5DD UK.

Duncan Macquarrie (D)

Green Chemistry Centre of Excellence, Department of Chemistry, University of York Heslington York YO10 5DD UK.

Pakin Noppawan (P)

Department of Chemistry, Faculty of Science, Mahasarakham University Maha Sarakham 44150 Thailand.

Andrew J Hunt (AJ)

Materials Chemistry Research Center (MCRC), Department of Chemistry and Centre of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University Khon Kaen 40002 Thailand andrew@kku.ac.th.

Classifications MeSH