943330-36-7Relevant academic research and scientific papers
Structural and Biochemical Characterization of the Curcumin-Reducing Activity of CurA from Vibrio vulnificus
Park, Soo-Bong,Bae, Da-Woon,Clavio, Nina Abigail B.,Zhao, Lei,Jeong, Chang-Sook,Choi, Bo Mee,Macalino, Stephani Joy Y.,Cha, Hee-Jeong,Park, Jin-Byung,Lee, Jun Hyuck,Nam, Sang-Jip,Choi, Sun,Kim, Min-Kyu,Cha, Sun-Shin
, p. 10608 - 10616 (2018/10/15)
Curcumin is a yellow-colored ingredient in dietary spice turmeric (Curcuma longa Linn). This nontoxic polyphenol has antitumor, anti-inflammatory, apoptotic, and antioxidant activities. The ingested curcumin is reduced to multihydrated forms with more potent therapeutic potentials by the curcumin reductase (CurA) from commensal Escherichia coli. In this study, we demonstrated that Vibrio vulnificus CurA (VvCurA) with 87% sequence similarity to the E. coli CurA exhibits the curcumin-reducing activity through spectrophotometric detection of NADPH oxidation and high performance liquid chromatographic analysis of curcumin consumption and product generation. Afterward, we determined the crystal structures of VvCurA and the VvCurA/NADPH complex, and made the in silico model of the VvCurA/NADPH/curcumin ternary complex through induced fit docking. Based on structural information, active site residues that play critical roles in catalysis have been identified and characterized by mutational and kinetic studies, leading us to propose the reaction mechanism of CurA.
Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism
Hassaninasab, Azam,Hashimoto, Yoshiteru,Tomita-Yokotani, Kaori,Kobayashi, Michihiko
body text, p. 6615 - 6620 (2012/03/12)
Polyphenol curcumin, a yellow pigment, derived from the rhizomes of a plant (Curcuma longa Linn) is a natural antioxidant exhibiting a variety of pharmacological activities and therapeutic properties. It has long been used as a traditional medicine and as a preservative and coloring agent in foods. Here, curcumin-converting microorganisms were isolated from human feces, the one exhibiting the highest activity being identified as Escherichia coli. We are thus unique in discovering that E. coli was able to act on curcumin. The curcumin-converting enzyme was purified from E. coli and characterized. The native enzyme had a molecular mass of about 82 kDa and consisted of two identical subunits. The enzyme has a narrow substrate spectrum, preferentially acting on curcumin. The microbial metabolism of curcumin by the purified enzyme was found to comprise a two-step reduction, curcumin being converted NADPH-dependently into an intermediate product, dihydrocurcumin, and then the end product, tetrahydrocurcumin. We named this enzyme "NADPH-dependent curcumin/dihydrocurcumin reductase" (CurA). The gene (curA) encoding this enzyme was also identified. A homology search with the BLAST program revealed that a unique enzyme involved in curcumin metabolism belongs to the medium-chain dehydrogenase/reductase superfamily.
Microbial transformation of curcumin by Rhizopus chinensis
Zhang, Xing,Ye, Min,Li, Rui,Yin, Jun,Guo, De-An
experimental part, p. 380 - 386 (2011/10/08)
Curcumin (1) is a potent antioxidant and antitumor natural product. In spite of its efficacy and safety, its clinical use is hindered mainly by poor water solubility and bioavailability. Structural modification to introduce hydrophilic functions is a promising approach to resolve this problem. In the present study we first found that curcumin could be efficiently converted into glucosides by filamentous fungi including Rhizopus chinensis IFFI 03043, Absidia coerulea AS 3.3389 and Cunninghamella elegans AS 3.1207. Curcumin 4′-O-β-d-glucoside (2), together with hexahydrocurcumin (3), was isolated from a preparative-scale biotransformation with R. chinensis IFFI 03043 and characterized fully by NMR and MS. A time-course study revealed that curcumin could be efficiently converted into curcumin 4′-O-β-d- glucoside within 8 h when administered at 0.05 mmol L-1 and the productivity was 57%. Additionally, the biotransformation products of curcumin by different fungal strains were analyzed by LC/MS. At least 15 metabolites were detected, and the predominant biotransformation reaction was glucosylation. This study provides a simple, efficient and less expensive approach for the preparation of curcumin glucosides. The introduction of the glucosyl function might be able to enhance the bioavailability of curcumin.
Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity
Changtam, Chatchawan,Hongmanee, Poonpilas,Suksamrarn, Apichart
experimental part, p. 4446 - 4457 (2010/10/19)
Curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3), the curcuminoid constituents of the medicinal plant Curcuma longa L., have been structurally modified to 55 analogs and antimycobacterial activity against Mycobacterium tuberculosis has been evaluated. Among the highly active curcuminoids, the isoxazole analogs are the most active group, with mono-O-methylcurcumin isoxazole (53) being the most active compound (MIC 0.09 μg/mL). It was 1131-fold more active than curcumin (1), the parent compound, and was approximately 18 and 2-fold more active than the standard drugs kanamycin and isoniazid, respectively. Compound 53 also exhibited high activity against the multidrug-resistant M. tuberculosis clinical isolates, with the MICs of 0.195-3.125 μg/mL. The structural requirements for a curcuminoid analog to exhibit antimycobacterial activity are the presence of an isoxazole ring and two unsaturated bonds on the heptyl chain. The presence of a suitable para-alkoxyl group on the aromatic ring which is attached in close proximity to the nitrogen function of the isoxazole ring and a free para-hydroxyl group on another aromatic ring enhances the biological activity.
Diarylheptanoids from the Rhizomes of Curcuma xanthorrhiza and Alpinia officinarum
Uehara, Shin-ichi,Yasuda, Ichiro,Akiyama, Kazuyuki,Morita, Hiroshi,Takeya, Koichi,Itokawa, Hideji
, p. 3298 - 3304 (2007/10/02)
Five diarylheptanoids including two new compounds were isolated from the rhizomes of Curcuma xanthorrhiza (Zingiberaceae).The structures of the new compounds were determined to be octahydrocurcumin ((3S, 5S)-1,7-bis(4-hydroxy-3-methoxyphenyl)-heptane-3,5-diol) (Ia) and (1ξ)-1-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-6-heptene-3,5-dione (II) on the basis of spectral and chemical evidence.The absolute configurations of Ia and a new similar diarylheptanoid, (3R, 5R)-1-(4-hydroxyphenyl)-7-phenylheptane-3,5-diol (VIa), isolated from the rhizomes of Alpinia officinarum (Zingiberaceae), were established by application of the exciton chirality rule.Keywords--diarylheptanoid; Curcuma xanthorrhiza; Alpinia officinarum; Zingiberaceae; (3S, 5S)-1,7-bis(4-hydroxy-3-methoxyphenyl)-heptane-3,5-diol; (1ξ)-1-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-6-heptene-3,5-dione; (3R, 5R)-1-(4-hydroxyphenyl)-7-phenylheptane-3,5-diol; exciton chirality rule; CD
Synthesis of Dihydrocurcumin
Krishnamurty, H. G.,Ghosh, Sanjukta
, p. 411 - 412 (2007/10/02)
Dihydrocurcumin is synthesised by C-acylation of 4-O-benzylvanillylideneaceton (3b) with 4-O-benzyldihydroferulic acid chloride (2b) in the presence of NaH-THF.
