Biotransformation of Erythrodiol for New Food Supplements with Anti-Inflammatory Properties

Abstract

Erythrodiol, a typical pentacyclic triterpenic diol in olive oil and its byproduct, olive pomace, frequently appears in food additives for the prevention of cardiovascular diseases because of its antioxidation, anti-inflammatory, and antitumor activities.To develop new derivatives of erythrodiol (1), preparative biotransformations were investigated through Streptomyces griseus ATCC 13273, Penicilium griseofulvum CICC 40293, and Bacillus subtilis ATCC 6633, and ten new (1a−1j) and one known metabolites were isolated. Their structures were elucidated by high resolution electrospray ionization mass spectrometry (HR-ESI-MS) and onedimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) spectroscopy. Furthermore, relative to 1, most metabolites exhibited lower toxicity and more potent inhibitory activities against nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. In particular, the glycosylated metabolite 1k showed a dramatically increased inhibitory effect with an IC 50 value of 2.40 μM, which is even lower than that of quercetin. Thus, biotransformation of erythrodiol is a viable strategy for discovering new triterpenes as food supplements with anti-inflammatory properties.

Systematic Review of Potential Anticancerous Activities of Erythrina senegalensis DC (Fabaceae)

“…Despite their better in vitro potency, the effects of maniladiol and erythrodiol against cancer models have been poorly investigated. Interest seems to be turned onto some less hydrophobic derivatives [ 142 , 143 , 144 ]. Noteworthy, the introduction of an oxygen substituent into the C-ring increases the biological activities, including cytotoxic effects [ 145 ].…”

Derivatization of Soyasapogenol A through Microbial Transformation for Potential Anti-inflammatory Food Supplements

“…The biotransformation was carried out according to the standard two-stage fermentation protocol previously reported in our lab. , Briefly, B. megaterium CGMCC 1.1741, P. griseofulvum CICC 40293, and S. griseus ATCC 13273 were incubated in soybean meal glucose medium, whereas B. subtilis ATCC 6633 was cultured in potato dextrose (PD) medium. The culture control contained a sterile medium, microorganisms but no substrate, and the substrate control contained a sterile medium as well as substrate but no microorganisms.…”

“…21,25 The biotransformation of erythrodiol, a dietary pentacyclic triterpenic diol, has been carried out previously in our laboratory. 26 Driven by the intense interest in exploiting soybean waste residues to develop pentacyclic triterpenoids as food supplements from oilseed crops, the soyasaponins were extracted from soybean oil residues and were acid hydrolyzed to obtain soyasapogenol A. The soyasapogenol A was used as a primary substance and subsequently was subjected to microbial transformation using four selected microorganism strains, i.e., Bacillus megaterium CGMCC 1.1741, Penicillium griseof ulvum CICC 40293, Bacillus subtilis ATCC 6633, and Streptomyces griseus ATCC 13273.…”

“…Biotransformation is a biochemical reaction in which exogenous substrates are selectively modified by multienzyme systems of microorganisms in a highly efficient, cost-effective, and eco-friendly manner, thereby producing novel bioactive derivatives that are difficult to obtain by conventional methods . Using microorganisms such as bacteria and fungi as a biocatalytic system can simulate the metabolism to perform selective conversion reactions in an environmentally friendly way. − Recent studies have shown that a microbial transformation is an effective tool for modifying the structures of natural bioactive compounds having diverse scaffolds, such as triterpenoids. , The biotransformation of erythrodiol, a dietary pentacyclic triterpenic diol, has been carried out previously in our laboratory …”

Biotransformation of Betulonic Acid by the Fungus Rhizopus arrhizus CGMCC 3.868 and Antineuroinflammatory Activity of the Biotransformation Products

“…Biotransformation is an alternative approach for achieving structural diversity, especially for particularly complex natural products. − It can be employed to target positions that would be difficult to functionalize by conventional chemical methods. Common enzymes to catalyze biotransformation reactions include cytochrome p450, glycosyltransferases, and acetyltransferase. , In our previous research, microbial transformation was proven to be powerful in achieving structural diversification of triterpenoids because of its significant stereo- and regioselective catalytic abilities. − Several microbial transformations of betulonic acid to obtain derivatives with improved polarity and pharmacological properties have been reported. − Thus, it is highly valuable to prepare betulonic acid derivatives using biotransformations.…”