The applications of curcumin have been limited by its poor water solubility and low bioavailability. In this study, we successfully synthesized a new curcumin derivative, curcumin-8′-O-4″-O-methyl-β-D-glucopyranoside, by biotransformation with the fungal strain Beauveria bassiana ATCC 7159. The structure of this new product was determined on the basis of spectroscopic data. This is the first record of a curcumin glycoside that has been synthesized by a fungus.
AnandP, ThomasSG, KunnumakkaraAB, SundaramC, HarikumarKB, SungB, TharakanST, MisraK, PriyadarsiniIK, RajasekharanKN, AggarwalBB. (2008) Biological activities of curcumin and its analogues (congeners) made by man and Mother Nature. Biochemical Pharmacology, 76, 1590–1611.
2.
AkT, GulcinI. (2008) Antioxidant and radical scavenging properties of curcumin. Chemico-Biological Interactions, 174, 27–37.
3.
AnandP, SundaramC, JhuraniS, KunnumakkaraAB, AggarwalBB. (2008) Curcumin and cancer: An “old-age” disease with an “age-old” solution. Cancer Letters, 267, 133–164.
4.
KulkarniSK, BhutaniMK, BishnoiM. (2008) Antidepressant activity of curcumin: involvement of serotonin and dopamine system. Psychopharmacology, 201, 435–442.
5.
ChenD, NieM, FanM, BianZ. (2008) Antiinflammatory activity of curcumin in macrophages stimulated by lipopolysaccharides from Porphyromonas gingivalis. Pharmacology, 82, 264–269.
6.
CikrikciS, MoziogluE, YilmazH. (2008) Biological activity of curcuminoids isolated from Curcuma longa. Records of Natural Products, 2, 19–24.
7.
AliBH, MarrifH, NoureldayemSA, BakheitAO, BlundenG. (2006) Some biological properties of curcumin: A review. Natural Product Communications, 1, 509–521.
8.
AnandP, KunnumakkaraAB, NewmanRA, AggarwalBB. (2007) Bioavailability of curcumin: problems and promises. Molecular pharmaceutics, 4, 807–818.
9.
BishtS, FeldmannG, SoniS, RaviR, KarikarC, MaitraA, MaitraA. (2007) Polymeric nanoparticle-encapsulated curcumin (“nanocurcumin”): a novel strategy for human cancer therapy. Journal of Nanobiotechnology, 5, 3.
10.
KaminagaY, NagatsuA, AkiyamaT, SugimotoN, YamazakiT, MaitaniT, MizukamiH. (2003) Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus. FEBS Letters, 555, 311–316.
11.
HollandHL, MorrisTA, NavaPJ, ZabicM. (1999) A new paradigm for biohydroxylation by Beauveria bassiana ATCC 7159. Tetrahedron, 55, 7441–7460.
12.
ZhanJ, GunatilakaAAL. (2005) Microbial transformation of curvularin. Journal of Natural Products, 68, 1271–1273.
13.
ZhanJ, GunatilakaAAL. (2006) Selective 4′-O-methylglycosylation of the pentahydroxy-flavonoid quercetin by Beauveria bassiana ATCC 7159. Biocatalysis and Biotransformation, 24, 396–399.
14.
ZhanJ, GunatilakaAAL. (2006) Microbial transformation of amino- and hydroxyanthraquinones by Beauveria bassiana ATCC 7159. Journal of Natural Products, 69, 1525–1527.
15.
ZhanJ, GunatilakaAAL. (2008) Microbial metabolism of 1-aminoanthracene by Beauveria bassiana. Bioorganic & Medicinal Chemistry, 16, 5085–5089.
16.
OlivoHF, PeeplesTL, RíosM, VelázquezF, KimJ, NarangS. (2003) Microbial C-hydroxylation and β-4-O-methylglucosidation of methyl-benzamide 7-azanorbornane ethers with Beauveria bassiana. Journal of Molecular Catalysis B: Enzymatic, 21, 97–105.
17.
ParvathyKS, NegiPS, SrinivasP. (2009) Antioxidant, antimutagenic and antibacterial activities of curcumin-β-diglucoside. Food Chemistry, 115, 265–271.
18.
SaladiniM, LazzariS, PignedoliF, RosaR, SpagnoloF, FerrariE. (2009) New synthetic glucosyl-curcuminoids, and their 1H and 13C NMR characterization, from Curcuma longa L. Plant Foods for Human Nutrition, 64, 224–229.
