Biotransformation using Mucor rouxii for the production of oleanolic acid derivatives and their antimicrobial activity against oral pathogens

Abstract

The goal of this study is to produce oleanolic acid derivatives by biotransformation process using Mucor rouxii and evaluate their antimicrobial activity against oral pathogens. The microbial transformation was carried out in shake flasks at 30°C for 216 h with shaking at 120 rpm. Three new derivatives, 7β-hydroxy-3-oxo-olean-12-en-28-oic acid, 7β,21β-dihydroxy-3-oxo-olean-12-en-28-oic acid, and 3β,7β,21β-trihydroxyolean-12-en-28-oic acid, and one know compound, 21β-hydroxy-3-oxo-olean-12-en-28-oic acid, were isolated, and the structures were elucidated on the basis of spectroscopic analyses. The antimicrobial activity of the substrate and its transformed products was evaluated against five oral pathogens. Among these compounds, the derivative 21β-hydroxy-3-oxo-olean-12-en-28-oic acid displayed the strongest activity against Porphyromonas gingivalis, which is a primary etiological agent of periodontal disease. In an attempt to improve the antimicrobial activity of the derivative 21β-hydroxy-3-oxo-olean-12-en-28-oic acid, its sodium salt was prepared, and the minimum inhibitory concentration against P. gingivalis was reduced by one-half. The biotransformation process using M. rouxii has potential to be applied to the production of oleanolic acid derivatives. Research and antimicrobial activity evaluation of new oleanolic acid derivatives may provide an important contribution to the discovery of new adjunct agents for treatment of dental diseases such as dental caries, gingivitis, and periodontitis.

Antioxidant and antimicrobial activity of Kielmeyera coriacea Mart. and Zucc

“…The ethanolic extract was more effective against the major etiologic agent of dental caries, the aerobic oral ), a MIC value lower than the positive control and is below to the isolated substances (Capel et al, 2011), to the same plant part. The cyclohexane fraction was more effective against the aerobic oral bacteria S. mutans (ATCC 25175), S. sanguinis (ATCC 10566) and against the anaerobic oral bacteria A. naesllundi (ATCC 19039) (all with MIC 6.2 µg ml -1 ).…”

Antimicrobial Activity of Oleanolic Acid for Foodborne Bacteria

“…Oleanolic acid는 pentacyclic triterpene으로 유리산이나 triterpenoid saponin의 아글리콘 형태로 자연계에 흔히 존 재하면서 3) , 항산화 11,12) , 염증반응 억제 13) , 간 보호 14) , 위 보 호 15) , 암세포에 대한 독성 16) , 항 궤양 17) , 항고지혈증 18) 등 에 대한 생리활성을 가지고 있다 [19][20][21] . , 특히 정향 잎(Syzygium aromaticum; 1.65 g/100 g 건조중량) 24) , 올리브 잎(Olea europaea; 3.1 g/100 g 건조중량) [25][26][27] , 로즈마리 잎(Rosmarinus officinalis; 1.23/100 g 건조중량) [28][29][30] 등에서 추출 된다.…”

Microbial-Catalyzed Biotransformation of Multifunctional Triterpenoids Derived from Phytonutrients

“…Microbial cell-based transformations of triterpenoids have been developed primarily in the past two decades to produce novel lead molecules, new pharmaceuticals, and agrochemical compounds [7,8,27,28,29,30,31]. Some synthetic oleanane triterpenoids derived from microbial transformation act as multifunctional drugs that regulate the activity of entire networks [32,33,34,35,36]. Microbial biocatalysis has already been proven as powerful tool in the generation of structural diversity in triterpenoid skeletons for future structure-activity relationship studies [5,6,7,8].…”