title: Synthesis and biological evaluation of glucosyl curcuminoids.
abstract: Medicinal plants proved to be a rich source in exploring a variety of lead structures in the development of new drugs. The natural curcuminoids have gained considerable attention in recent years for their multiple beneficial pharmacological and biological activities. Clinical application of these curcuminoids is often impaired due to their poor water solubility, resulting in low in vivo bioavailability of the active compound in humans. The objective of the present study is to synthesize glucosyl conjugates of curcumin 1 and tetrahydrocurcumin 4 and to evaluate their biological activities. The study highlights the synthesis of curcumin-β-di-glucoside 3 (yield 71%) and tetrahydrocurcumin-β-di-glucoside 6 (yield 64%) in good yields in a biphasic reaction medium using a phase transfer catalyst under simple and ecofriendly conditions. Both the glucosyl curcuminoids showed enhanced antioxidant, tyrosinase enzyme inhibitory, antimicrobial and potent cytotoxic activity. The improved biological activity may be due to the increased solubility of the glucosyl conjugated compounds compared to the native curcuminoids; this was further confirmed by partition coefficient studies. Thus, the synthesized glucosyl curcumin may serve as promising future therapeutic molecule in the management of cancer, whereas glucosyl tetrahydrocurcumin can be a useful ingredient in achromatic food and in cosmetic applications.
authors.affiliation: Medicinal Chemistry and Pharmacology Division, CSIR - Indian Institute of Chemical Technology, Tarnaka, Hyderabad, India.
authors.forename: Adari
authors.initials: A
authors.lastname: Bhaskar Rao
authors.forename: Ernala
authors.initials: E
authors.lastname: Prasad
authors.forename: Seelam S
authors.initials: SS
authors.lastname: Deepthi
authors.forename: Imtiaz A
authors.initials: IA
authors.lastname: Ansari
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D030024:Curcuma; D003474:Curcumin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D005960:Glucosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D006031:Glycosylation; D019073:HT29 Cells; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D020128:Inhibitory Concentration 50; D061986:MCF-7 Cells; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors / Q000378:metabolism; D008517:Phytotherapy; D010946:Plants, Medicinal; D012995:Solubility; D013329:Structure-Activity Relationship
chemical_list: D000890:Anti-Infective Agents; D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D004791:Enzyme Inhibitors; D005960:Glucosides; C096277:tetrahydrocurcumin; D014442:Monophenol Monooxygenase; D003474:Curcumin
keywords: Antioxidant; Cosmetic; Hyperpigmentation; Tetrahydrocurcumin; Tyrosinase