943330-36-7Relevant articles and documents
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.
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.
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