Biotransformation of curcumin and structure–activity relationship (SAR) of its analogues: A systematic review

Abstract

Curcumin has been widely acclaimed for several pharmacological properties, such as antioxidant, antimicrobial, anticancer, and anti-inflammation. Curcumin's poor aqueous solubility, bioavailability, and cellular uptake hamper its ability to display maximum pharmacological effect in the human body. Synthesis of curcumin analogues to enhance its properties can be achieved through biotransformation. Greener, simpler, and higher selectivity and specificity make biotransformation an alternative approach when preparing curcumin analogues for the structure-activity relationship (SAR) study intended for drug design. This work systematically reviews the biotransformation of curcumin by utilizing fungi, gut microbiota, and enzymes. The SAR study of curcumin and its analogues for several bioactivities is also highlighted.

Microbial Transformation of Curcumin and Synergistic Investigation of Its Derivatives with Piperine

“…In the 1 M2 (yellow powder, 16 mg, 2.56 % yield), second metabolite purified from the fungal extract, has been revealed to have the same structure as the metabolite referred to as "Demethoxyoctahydrocurcumin," identified in a paper published by Younis and colleagues in 2016. [1,2] In the HR-ESI-MS spectrum of metabolite M2, the base ion peak at m/z 369.1669 [M + Na] + (calcd for C 20 H 26 O 5 Na, 369.1672). It exhibited blue fluorescence under UV at 365 nm, and gave faint purple spot when sprayed with the reagent containing anisaldehyde, sulfuric acid, methanol, and acetic acid.…”

“…Curcumin is widely used as a spice, and food coloring agent in yellow/orange powder form. [1,2] Curcumin has been extensively studied in the literature due to its wide range of pharmacological properties, leading to ongoing research in this field. [3][4][5][6][7][8][9][10][11][12] Curcumin exhibits a range of significant properties, including anti-inflammatory, antibacterial and strong antioxidant effects.…”

“…[23] Literature results support the possibility of curcumin derivatives having more potent biological effects than curcumin. [2] Synthetic reactions often require extreme conditions in comparison with microbial transformation. According to the literature, microbial transformation of curcumin has been the subject of a relatively small number of previously published studies.…”

“…It exists as a keto‐enol tautomer with a major keto form or a stable enol form in different solutions (neutral, acidic, and alkaline) (See Scheme 1.). Curcumin is widely used as a spice, and food coloring agent in yellow/orange powder form [1,2] …”

“…In research studies, curcumin derivatives are typically synthesized, and these synthetic derivatives, especially enone and dienone curcumin derivatives, have been noted for their superior antiangiogenic effects compared to curcumin [23] . Literature results support the possibility of curcumin derivatives having more potent biological effects than curcumin [2] . Synthetic reactions often require extreme conditions in comparison with microbial transformation.…”