Crocetin, dimethylcrocetin, and safranal bind human serum albumin: Stability and antioxidative properties

dc.contributor.author	Kanakis, CD	en
dc.contributor.author	Tarantilis, PA	en
dc.contributor.author	Tajmir-Riahi, HA	en
dc.contributor.author	Polissiou, MG	en
dc.date.accessioned	2014-06-06T06:47:39Z
dc.date.available	2014-06-06T06:47:39Z
dc.date.issued	2007	en
dc.identifier.issn	00218561	en
dc.identifier.uri	http://dx.doi.org/10.1021/jf062638l	en
dc.identifier.uri	http://62.217.125.90/xmlui/handle/123456789/3740
dc.subject	Antioxidant activity	en
dc.subject	Binding constant	en
dc.subject	Binding mode	en
dc.subject	Crocetin	en
dc.subject	Crocus sativus L.	en
dc.subject	Dimethylcrocetin	en
dc.subject	FT-IR	en
dc.subject	Human serum albumin	en
dc.subject	Protein	en
dc.subject	Saffron	en
dc.subject	Safranal	en
dc.subject	UV - vis spectroscopy	en
dc.subject.other	Crocus	en
dc.subject.other	Crocus sativus	en
dc.subject.other	antioxidant	en
dc.subject.other	carotenoid	en
dc.subject.other	crocetin	en
dc.subject.other	cyclohexene derivative	en
dc.subject.other	dimethylcrocetin	en
dc.subject.other	safranal	en
dc.subject.other	serum albumin	en
dc.subject.other	terpene	en
dc.subject.other	unclassified drug	en
dc.subject.other	article	en
dc.subject.other	drug stability	en
dc.subject.other	human	en
dc.subject.other	hydrogen bond	en
dc.subject.other	infrared spectroscopy	en
dc.subject.other	metabolism	en
dc.subject.other	protein binding	en
dc.subject.other	spectrophotometry	en
dc.subject.other	Antioxidants	en
dc.subject.other	Carotenoids	en
dc.subject.other	Cyclohexenes	en
dc.subject.other	Drug Stability	en
dc.subject.other	Humans	en
dc.subject.other	Hydrogen Bonding	en
dc.subject.other	Protein Binding	en
dc.subject.other	Serum Albumin	en
dc.subject.other	Spectrophotometry	en
dc.subject.other	Spectroscopy, Fourier Transform Infrared	en
dc.subject.other	Terpenes	en
dc.title	Crocetin, dimethylcrocetin, and safranal bind human serum albumin: Stability and antioxidative properties	en
heal.type	journalArticle	en
heal.identifier.primary	10.1021/jf062638l	en
heal.publicationDate	2007	en
heal.abstract	Crocetin (CRT) and dimethylcrocetin (DMCRT) are derived from crocins which are found in the stigmas of saffron (Crocus sativus L.), while safranal is the main component of saffron's essential oil. The aim of the present study was to examine their interaction with human serum albumin in aqueous solution at physiological conditions using constant protein concentration and various ligand contents. FT-IR and UV-visible spectroscopic methods were used to determine the ligands' binding mode, the binding constant, and the effects of ligand complexation on protein secondary structure. Structural analysis showed that crocetin, dimethylcrocetin, and safranal bind nonspecifically (H-bonding) via protein polar groups with binding constants of Kcrt =2.05 (±0.30) × 103 M-1, Kdmcrt = 9.60 (±0.35) × 104 M1, and Ksaf = 2.11 (±0.35) × 103 M-1. The protein secondary structure showed no major alterations at low ligand concentrations (1 μM), whereas at higher content (1 mM), decrease of α-helix from 55% (free HSA) to 43-45% and increase of β-sheet from 17% (free HSA) to 18-22% and random coil 7% (free HSA) to 10-14% occurred in the ligand - HSA complexes. The results point to a partial unfolding of protein secondary structure at high ligand content. The antioxidant activity of CRT, DMCRT, and safranal was also tested by the DPPH• antioxidant activity assay, and their IC50 values were compared to that of well-known antioxidants such as Trolox and butylated hydroxy toluene (BHT). The IC50 values of CRT and safranal were 17.8 ± 1 μg/mL and 95 ± 1 μg/mL, respectively, while the inhibition of DMCRT reached a point of 38.8%, which corresponds to a concentration of 40 μ/mL, and then started to decrease. The IC50 values of Trolox and BHT were 5.2 ± 1 μg/mL and 5.3 ± 1 μg/mL, respectively. © 2007 American Chemical Society.	en
heal.journalName	Journal of Agricultural and Food Chemistry	en
dc.identifier.issue	3	en
dc.identifier.volume	55	en
dc.identifier.doi	10.1021/jf062638l	en
dc.identifier.spage	970	en
dc.identifier.epage	977	en