Rosmarinic acid and its ester derivatives for enhancing antibacterial, α-glucosidase inhibitory, and lipid accumulation suppression activities.

Rosmarinic acid (RA), commonly found in Nepetoidae subfamily of Lamiaceae family, possesses various biological activities. To expand its application, RA was modified by esterification with methyl (me), propyl (pro), and hexyl (hex) alcohols and then tested antibacterial, α-glucosidase inhibitory, and lipid accumulation suppression activities. Consequently, RA derivatives enhanced antibacterial activity, especially the RA-pro and RA-hex, which effectively inhibited the growth of Bacillus cereus rather than tannic acid, a natural antibacterial agent. RA-hex also inhibited α-glucosidase inhibitory activity greater than luteolin. By computational molecular docking, dihydroxyphenyl group and hexyl group were selected as essential groups for interaction with the active site of α-glucosidase through hydrogen bonding and hydrophobic interaction, contributing to the great inhibitory activity. Furthermore, RA-pro and RA-hex effectively suppressed lipid accumulation of 3T3-L1 cells, superior to EGCG, a well-known anti-obesity phytochemical. These biological effects of RA derivatives commonly attributed to hydrophobicity, hydrogen bonding, and steric bulkiness of the side chain. PRACTICAL APPLICATIONS: Rosmarinic acid (RA), a fundamental compound in the family Lamiaceae, is one of powerful naturally occurring antioxidants as well as other biological activities. Furthermore, its abundance in nature was also high in amount in the plant kingdom. So, natural RA can be one of possible natural resources for creating potent natural drugs and biologically useful substances after chemical modification. Studies on various biological activities may intensively expand usage and application of RA. In this study, RA was derivatized to corresponding ester such as methyl, propyl, and hexyl alcohols with higher hydrophobicity, and found great antibacterial, α-glucosidase inhibitory, and lipid accumulation suppression activities. RA-pro and RA-hex significantly suppressed lipid accumulation and cell differentiation. Therefore, RA derivatives with multiple biological activities have the potential to be applied in the food and pharmaceutical industries as food ingredients and supplements.

A fast and sensitive isocratic high performance liquid chromatography method for determination of guaraná (Paullinia cupana) flavan-3-ols.

Most methods for quantification of catechins in guaraná and other food matrices rely on lengthy gradients to resolve all peaks, and the analysis time for one sample is around 45-135 min. The present method is a fast, sensitive and simple HPLC-UV method, with a 16-minute isocratic run that deliver the high throughput needed to process a large number of samples without compromising the analyte stability. This method is suitable for the determination of catechins, procyanidins (up to degree of polymerisation 2) and caffeine in guaraná extracts, in vitro digesta, and Caco-2 cell permeates. The higher sensitivity was achieved by detection at 210 nm, after checking for the absence of interfering substances in the matrices. The method was validated and LODs of 0.019, 0.030, 0.028, 0.030, and 0.043 nmol/mL were achieved for catechin, epicatechin, procyanidin B1, procyanidin B2 and caffeine, respectively. Standard recovery at three different concentrations were within 97-109%. Intra- and inter-day variabilities (RSD) were both under 4%. •This is an isocratic HPLC-UV method for the quantification of flavan-3-ols from guaraná (Paullinia cupana), which is 3-8 times faster and >80 times sensitive than previously published methods using UV or diode array detectors.•It is cost-effective as it uses the widely available and affordable UV detector and consumes less solvent due the short analysis time.•With low LODs, fast sample preparation and the short analytical run, this method can be used for the quantification of flavan-3-ols and caffeine in guaraná extracts as well as guaraná in vitro digesta and its Caco-2 permeates.

Does kappa-carrageenan thermoreversible gelation affect ß-carotene oxidative degradation and bioaccessibility in o/w emulsions?

In the present work oil-in-gel (o/g) emulsions comprising 0.4-1% w/w κ-carrageenan in the absence and presence of Ca2+ (20mM) were investigated for their ability to hamper the oxidative degradation under isothermal (5, 20 and 37°C) ambient air storage conditions and promote the in vitro bioaccessibility of ß-carotene. The mechanical and structure conformational aspects of the o/g emulsions throughout in vitro digestion were measured by means of oscillatory rheology and optical microscopy. Although the addition of κ-carrageenan reduced by more than 50% (from 0.85 to 0.40day-1) the ß-carotene oxidative degradation rates, only minor differences were detected in terms of gelation method (ca. 0.42 and 0.39day-1 for ionotropic and coldset systems) and biopolymer concentration (0.38-0.42day-1). The bioaccessibility of ß-carotene was significantly higher in coldset o/g emulsions (ca. 43%) compared to the ionically mediated ones (ca. 36%). With the exception of 0.4% κ-carrageenan containing o/g emulsions (55.4 and 49.7% for control and 0.4% κ-carrageenan respectively), the ß-carotene bioaccessibility was significantly reduced with the increase in κ-carrageenan concentration (ranging from 34 to 38.9%).

Modulation of chemical stability and in vitro bioaccessibility of beta-carotene loaded in kappa-carrageenan oil-in-gel emulsions.

In the present paper, ionotropically structured κ-carrageenan based oil-in-gel (o/g) emulsions were tested as potential carrier systems for the delivery of ß-carotene. In situ ionic gelation was induced by Na+, K+ or Ca2+ added at the level of 0.2-0.6% (w/w). All o/g emulsions exerted a true gel like behaviour with storage modulus (G') being reduced according to the order: K+>Ca2+>Na+. Ionic gelation induced a moderate increase in the microscopically assessed lipid droplets radii. O/g emulsions containing monovalent ions exerted the highest ß-carotene retention throughout isothermal storage particularly at high (37 and 55°C) temperatures. Notwithstanding, increasing ionic strength resulted in acceleration of ß-carotene degradation rates for all cation species. ß-Carotene bioaccessibility was significantly lower in Ca2+o/g emulsions due to the formation of complexes between the biopolymer matrix containing ß-carotene and bile salts. A good correlation between ß-carotene bioaccessibility, physical and colloidal aspects of the micellar digesta fractions was observed.

Bioavailability of catechins from guaraná (Paullinia cupana) and its effect on antioxidant enzymes and other oxidative stress markers in healthy human subjects.

We assessed the effects of guaraná (Paullinia cupana) consumption on plasma catechins, erythrocyte antioxidant enzyme activity (superoxide dismutase, catalase and glutathione peroxidase) and biomarkers of oxidative stress (ex vivo LDL oxidation, plasma total antioxidant status and ORAC, and lymphocyte single cell gel electrophoresis) in healthy overweight subjects. Twelve participants completed a 15-day run-in period followed by a 15-day intervention with a daily intake of 3 g guaraná seed powder containing 90 mg (+)-catechin and 60 mg (-)-epicatechin. Blood samples were taken on the first and last day of the intervention period, fasting and 1 h post-dose. The administration of guaraná increased plasma ORAC, while reducing ex vivo LDL oxidation (only in the first study day) and hydrogen peroxide-induced DNA damage in lymphocytes, at 1 h post-dose. Plasma catechin (0.38 ± 0.12 and 0.44 ± 0.18 nmol mL(-1)), epicatechin (0.59 ± 0.18 and 0.64 ± 0.25 nmol mL(-1)) and their methylated metabolites were observed at 1 h post-dose but were almost negligible after overnight fasting. The activities of catalase (in both study days) and glutathione peroxidase (in the last intervention day) increased at 1 h post-dose. Furthermore, the activity of both enzymes remained higher than the basal levels in overnight-fasting individuals on the last intervention day, suggesting a prolonged effect of guaraná that continues even after plasma catechin clearance. In conclusion, guaraná catechins are bioavailable and contribute to reduce the oxidative stress of clinically healthy individuals, by direct antioxidant action of the absorbed phytochemicals and up-regulation of antioxidant/detoxifying enzymes.

Absorption, Metabolism, and Excretion by Freely Moving Rats of 3,4-DHPEA-EDA and Related Polyphenols from Olive Fruits (Olea europaea).

Absorption, metabolism, and excretion of 3,4-DHPEA-EDA, oleuropein, and hydroxytyrosol isolated from olive fruits were newly evaluated after oral and intravenous administration in freely moving rats cannulated in the portal vein, jugular vein, and bile duct. Orally administered 3,4-DHPEA-EDA, an important bioactive compound in olive pomace, was readily absorbed and metabolized to hydroxytyrosol, homovanillic acid, and homovanillyl alcohol, as shown by dose-normalized 4 h area under the curve (AUC0→4 h/Dose) values of 27.7, 4.5, and 4.2 µM·min·kg/µmol, respectively, in portal plasma after oral administration. The parent compound 3,4-DHPEA-EDA was not observed in the portal plasma, urine, and bile after oral and intravenous administration. Additionally, hydroxytyrosol, homovanillic acid, and homovanillyl alcohol in the portal plasma after oral administration of hydroxytyrosol showed 51.1, 22.8, and 7.1 µM·min·kg/µmol AUC0→4 h/Dose, respectively. When oleuropein, a polar glucoside, was injected orally, oleuropein in the portal plasma showed 0.9 µM·min·kg/µmol AUC0→4 h/Dose. However, homovanillic acid was detected from oleuropein in only a small amount in the portal plasma. Moreover, the bioavailability of hydroxytyrosol and oleuropein for 4 hours was 13.1% and 0.5%, respectively. Because the amount of 3,4-DHPEA-EDA in olive fruits is about 2-3 times greater than that of hydroxytyrosol, the metabolites of 3,4-DHPEA-EDA will influence biological activities.

Lysoglyceroglycolipids Improve the Intestinal Absorption of Micellar Fucoxanthin by Caco-2 Cells.

To improve the intestinal absorption of fucoxanthin, we evaluated the effects of dietary glyceroglycolipids on the uptake and secretion of fucoxanthin solubilized in mixed micelles by human intestinal Caco-2 cells. Although digalactosyldiacylglycerol and sulfoquinovosyldiacylglycerol suppressed fucoxanthin uptake and secretion, their lyso-types, digalactosylmonoacylglycerol and sulfoquinovosylmonoa cylglycerol, remarkably enhanced them. Thus, some dietary glyceroglycolipids may be potential enhancers of fucoxanthin bioavailability in humans.

Glyceroglycolipids Affect Uptake of Carotenoids Solubilized in Mixed Micelles by Human Intestinal Caco-2 Cells.

We previously reported that phospholipids markedly affected the uptake of carotenoids solubilized in mixed micelles by human intestinal Caco-2 cells. In the present study, we found that two classes of dietary glyceroglycolipids and the corresponding lysoglyceroglycolipids affected uptake of ß-carotene and lutein by differentiated Caco-2 cells. The levels of carotenoid uptake from micelles containing digalactosyldiacylglycerol or sulfoquinovosyldiacylglycerol were significantly lower than that from control micelles. On the other hand, the uptakes from micelles containing digalactosylmonoacylglycerol or sulfoquinovosylmonoacylglycerol were significantly higher than that from control micelles. In dispersed cells and Caco-2 cells with poor cell-to-cell adhesion, however, the levels of uptake from micelles containing these lyso-lipids were much lower than that from control micelles. The uptake levels from control micelles were markedly decreased depending on the development of cell-to-cell/cell-matrix adhesion in Caco-2 cells, but the uptake levels from the micelles containing these lyso-lipids were not substantially changed, suggesting that the intercellular barrier formed by cell-to-cell/cell-matrix adhesion inhibited the uptake from control micelles, but not from the lyso-lipid-containing micelles. The lyso-lipids appeared to enhance carotenoid uptake by decreasing the intercellular barrier integrity. The results showed that some types of glyceroglycolipids have the potential to modify the intestinal uptake of carotenoids.

Antiallergic activity of rosmarinic acid esters is modulated by hydrophobicity, and bulkiness of alkyl side chain.

Methyl, propyl and hexyl esters of rosmarinic, caffeic and p-coumaric acids were tested for antiallergic activity, and rosmarinic acid propyl ester exhibited the greatest ß-hexosaminidase release suppression (IC50, 23.7 µM). Quadratic correlations between pIC50 and cLogP (r(2) = 0.94, 0.98, and 1.00, respectively) were observed in each acid ester series. The antiallergic activity is modulated by hydrophobicity, and alkyl chain bulkiness.

Probiotic edible films as a new strategy for developing functional bakery products: The case of pan bread.

In the present paper, a novel approach for the development of probiotic baked cereal products is presented. Probiotic pan bread constructed by the application of film forming solutions based either on individual hydrogels e.g. 1% w/w sodium alginate (ALG) or binary blends of 0.5% w/w sodium alginate and 2% whey protein concentrate (ALG/WPC) containing Lactobacillus rhamnosus GG, followed by an air drying step at 60 °C for 10 min or 180 °C for min were produced. No visual differences between the bread crust surface of control and probiotic bread were observed. Microstructural analysis of bread crust revealed the formation of thicker films in the case of ALG/WPC. The presence of WPC improved significantly the viability of L. rhamnosus GG throughout air drying and room temperature storage. During storage there was a significant reduction in L. rhamnosus GG viability during the first 24 h, viable count losses were low during the subsequent 2-3 days of storage and growth was observed upon the last days of storage (day 4-7). The use of film forming solutions based exclusive on sodium alginate improved the viability of L. rhamnosus GG under simulated gastro-intestinal conditions, and there was no impact of the bread crust matrix on inactivation rates. The presence of the probiotic edible films did not modify cause major shifts in the mechanistic pathway of bread staling - as shown by physicochemical, thermal, texture and headspace analysis. Based on our calculations, an individual 30-40 g bread slice can deliver approx. 7.57-8.98 and 6.55-6.91 log cfu/portion before and after in-vitro digestion, meeting the WHO recommended required viable cell counts for probiotic bacteria to be delivered to the human host.

Microencapsulation of Lactobacillus acidophilus NCIMB 701748 in matrices containing soluble fibre by spray drying: Technological characterization, storage stability and survival after in vitro digestion.

We evaluated sodium alginate, chitosan and hydroxypropyl methylcellulose (HPMC) as co-encapsulants for spray dried Lactobacillus acidophilus NCIMB 701748 by assessing their impact on cell viability and physicochemical properties of the dried powders, viability over 35 days of storage at 25 °C and survival after simulated digestion. Fibres were added to a control carrier medium containing whey protein concentrate, d-glucose and maltodextrin. Sodium alginate and HPMC did not affect cell viability but chitosan reduced viable counts in spray dried powders, as compared to the control. Although chitosan caused large losses of viability during spray-drying, these losses were counteracted by the excellent storage stability compared to control, sodium alginate and HPMC, and the overall effect became positive after the 35-day storage. Chitosan also improved survival rates in simulated GI conditions, however no single fibre could improve L. acidophilus NCIMB 701748 viability in all steps from production through storage and digestion.

Stability of Lactobacillus rhamnosus GG in prebiotic edible films.

The concept of prebiotic edible films as effective vehicles for encapsulating probiotic living cells is presented. Four soluble fibres (inulin, polydextrose, glucose-oligosaccharides and wheat dextrin) were selected as prebiotic co-components of gelatine based matrices plasticised with glycerol and used for the immobilisation of Lactobacillus rhamnosus GG. The addition of prebiotics was associated with a more compact and uniform film structure, with no detectable interspaces or micropores; probiotic inclusion did not significantly change the structure of the films. Glucose-oligosaccharides and polydextrose significantly enhanced L. rhamnosus GG viability during air drying (by 300% and 75%, respectively), whilst a 33% and 80% reduction in viable counts was observed for inulin and wheat dextrin. Contrarily, inulin was the most effective at controlling the sub-lethal effects on L. rhamnosus GG during storage. However, in all cases the supplementation of edible films with prebiotics ameliorated the storage stability of L. rhamnosus GG.

Comparison of ambient solvent extraction methods for the analysis of fatty acids in non-starch lipids of flour and starch.

BACKGROUND: Lipids are minor components of flours, but are major determinants of baking properties and end-product quality. To the best of our knowledge, there is no single solvent system currently known that efficiently extracts all non-starch lipids from all flours without the risk of chemical, mechanical or thermal damage. This paper compares nine ambient solvent systems (monophasic and biphasic) with varying polarities: Bligh and Dyer (BD); modified Bligh and Dyer using HCl (BDHCL); modified BD using NaCl (BDNaCl); methanol-chloroform-hexane (3:2:1, v/v); Hara and Radin (hexane-isopropanol, 3:2, v/v); water-saturated n-butanol; chloroform; methanol and hexane for their ability to extract total non-starch lipids (separated by lipid classes) from wheat flour (Triticum aestivum L.). Seven ambient extraction protocols were further compared for their ability to extract total non-starch lipids from three alternative samples: barley flour (Hordeum vulgare L.), maize starch (Zea mays L.) and tapioca starch (Manihot esculenta Crantz). RESULTS: For wheat flour the original BD method and those containing HCl or NaCl tended to extract the maximum lipid and a significant correlation between lipid extraction yield (especially the glycolipids and phospholipids) and the polarity of the solvent was observed. For the wider range of samples BD and BD HCl repeatedly offered the maximum extraction yield and using pooled standardized (by sample) data from all flours, total non-starch lipid extraction yield was positively correlated with solvent polarity (r = 0.5682, P < 0.05) and water ratio in the solvent mixture (r = 0.5299, P < 0.05). CONCLUSION: In general, BD-based methods showed better extraction yields compared to methods without the addition of water and, most interestingly, there was much greater method dependence of lipid yields in the starches when compared to the flour samples, which is due to the differences in lipid profiles between the two sample types (flours and starches).

Development and validation of methods for the extraction of phenolic acids from plasma, urine, and liver and analysis by UPLC-MS.

This study developed and validated a method for the extraction and determination of 11 phenolic acids in rat plasma, urine, and liver by ultraperformance liquid chromatography-mass spectrometry (UPLC-MS). A system suitability test (instrumental linearity, area, and retention time precision) was performed and recovery, intraday and between-day precisions, detection limits (LOD), and quantification limits (LOQ) were determined for all compounds in each biological matrix. Recoveries varied between 88 and 117% in plasma, between 87 and 102% in urine, and between 38 and 100% in liver. Precision was higher than 13.7% intraday and 14.0% interday in all matrices, at three concentration levels. To demonstrate the applicability, the method was used to estimate the concentrations of phenolic acids in samples from animals that received 5-caffeoylquinic acid (5-CQA) by gavage. The excellent validation results and the applicability of the method to real samples confirmed the suitability for studies on absorption, bioavailability, and pharmacokinetics of phenolic acids derived from foods rich in phenolic compounds.

Keto-carotenoids are the major metabolites of dietary lutein and fucoxanthin in mouse tissues.

Fucoxanthin, a xanthophyll present in brown algae consumed in Eastern Asia, can suppress carcinogenesis and obesity in rodents. We investigated the metabolism, tissue distribution, and depletion of fucoxanthin in ICR mice by comparison with those of lutein. The experiments comprised 14-d dietary supplementation with lutein esters or fucoxanthin, followed by 41- or 28-d, respectively, depletion periods with carotenoid-free diets. After lutein ester supplementation, 3'-hydroxy-ε,ε-caroten-3-one and lutein were the predominant carotenoids in plasma and tissues, accompanied by ε,ε-carotene-3,3'-dione. The presence of these keto-carotenoids in mouse tissues is reported here for the first time, to our knowledge. Lutein and its metabolites accumulated most in the liver (7.51 µmol/kg), followed by plasma (2.11 µmol/L), adipose tissues (1.01-1.44 µmol/kg), and kidney (0.87 µmol/kg). The half-life of the depletion (t(1/2)) of lutein metabolites varied as follows: plasma (1.16 d) < liver (2.63 d) < kidney (4.44 d) < < < adipose tissues (>41 d). Fucoxanthinol and amarouciaxanthin A were the main metabolites in mice fed fucoxanthin and partitioned more into adipose tissues (3.13-3.64 µmol/kg) than into plasma, liver, and kidney (1.29-1.80 µmol/kg). Fucoxanthin metabolites had shorter t(1/2) in plasma, liver, and kidneys (0.92-1.23 d) compared with those of adipose tissues (2.76-4.81 d). The tissue distribution of lutein and fucoxanthin metabolites was not associated with their lipophilicity, but depletion seemed to be slower for more lipophilic compounds. We concluded that mice actively convert lutein and fucoxanthin to keto-carotenoids by oxidizing the secondary hydroxyl groups and accumulate them in tissues.

Effect of glycerophospholipid class on the beta-carotene uptake by human intestinal Caco-2 cells.

The effects were evaluated of various glycerophospholipids on the uptake of beta-carotene solubilized in mixed micelles by human intestinal Caco-2 cells. Phosphatidylethanolamine markedly enhanced the transfer of beta-carotene from the micelles to the cells, whereas phosphatidylcholine suppressed it. All the lysoglycerophospholipids enhanced the transfer, irrespective of the polar head group. Glycerophospholipids therefore have the potential to modify the intestinal absorption of carotenoids.

Soluble fibers inhibit carotenoid micellization in vitro and uptake by Caco-2 cells.

We evaluated the effects of soluble fibers on beta-carotene and lutein micellization during simulated digestion in vitro, and on carotenoid uptake from mixed micelles by Caco-2 cells. Medium- and high-viscosity alginates and pectins inhibited carotenoid micellization and cellular uptake relative to the fiber-free control. Alginates, carboxy-methylcelluloses, and methylcelluloses inhibited beta-carotene uptake mainly by increasing medium viscosity, but pectins might inhibit carotenoid uptake by additional mechanisms.

Low bioavailability of dietary epoxyxanthophylls in humans.

Epoxyxanthophylls (epoxide-containing xanthophylls), a group of carotenoids, are ubiquitously distributed in edible plants. Among them, neoxanthin in green leafy vegetables and fucoxanthin in brown algae have been reported to exhibit an antiproliferative effect on several human cancer cells in vitro. However, there is little information about the intestinal absorption and metabolic fate of dietary epoxyxanthophylls in humans. To estimate the intestinal absorption of neoxanthin and fucoxanthin in humans, we evaluated the plasma epoxyxanthophyll concentrations before and after 1-week dietary interventions with spinach (Spinacia oleracea) and wakame (Undaria pinnatifida). The epoxyxanthophylls and their metabolites in the plasma extracts were determined by HPLC after partial purification and concentration with solid-phase extraction cartridges. Even after 1 week of spinach intake (3.0 mg neoxanthin/d), the plasma concentrations of neoxanthin and its metabolites (neochrome stereoisomers) remained very low (about 1 nmol/l), whereas those of beta-carotene and lutein were markedly increased. Similarly, the plasma concentration of fucoxanthinol, a gastrointestinal metabolite of fucoxanthin, was < 1 nmol/l after 1 week of wakame intake (6.1 mg fucoxanthin/d). These results indicated that the plasma response to dietary epoxyxanthophylls was very low in humans even after 1-week intake of epoxyxanthophyll-rich diets.

Intestinal absorption of dietary carotenoids.

The assessment of carotenoid bioavailability has long been hampered by the limited knowledge of their absorption mechanisms. However, recent reports have elucidated important aspects of carotenoid digestion and absorption. Disruption of food matrix and increasing amounts of fat seem to enhance the absorption of carotenes to a larger extent than that of xanthophylls. Comparing different carotenoid species, xanthophylls seem to be more easily released from the food matrix and more efficiently micellized than the carotenes. On the other hand, carotenes are more efficiently taken up by the enterocytes. However, carotenoid emulsification and micellization steps are largely affected by the food matrix and dietary components, being the main determinant of carotenoid bioavailability from foodstuffs. Although the intestinal uptake of carotenoids has been thought to occur by simple diffusion, recent studies reported the existence of receptor-mediated transport of carotenoids in enterocytes. Comparisons between the intestinal absorption of a wide array of carotenoids would be useful to elucidate the absorption mechanism of each carotenoid species, in view of the recent indications that intestinal carotenoid uptake may involve the scavenger receptor class B type I and possibly other epithelial transporters. The unraveling of the whole mechanism underlying the absorption of carotenoids will be the challenge for future studies.

Acyl moieties modulate the effects of phospholipids on beta-carotene uptake by Caco-2 cells.

The intestinal absorption of carotenoids is thought to be mediated by the carotenoid assembly in mixed micelles, followed by its transfer into the enterocytes and subsequent secretion to the lymph as chylomicron particles. In the present study we investigated the effects of phospholipids and lysophospholipids with diverse fatty acyl moieties on the uptake of beta-carotene solubilized in mixed micelles by Caco-2 cells. Compared with phospholipid-free mixed micelles (NoPL), those containing long-chain PC inhibited beta-carotene uptake (16:0,18:1-PC approximately equal to 16:0,18:2-PC < 14:0,14:0-PC approximately equal to 16:0, 14:0-PC < 16:0,16:0-PC < NoPL). However, mixed micelles containing medium-chain PC enhanced beta-carotene uptake (NoPL < 8:0,8:0-PC < 12:0,12:0-PC < 10:0,10:0-PC), and short-chain PC did not affect the uptake. Among the lysophosphatidylcholine (LysoPC) class, a marked increase of beta-carotene uptake by medium-to-long-chain LysoPC was observed (NoPL < 12:0-LysoPC < 14:0-LysoPC < 18:1-LysoPC < 16:0-LysoPC), although short-to-medium-chain LysoPC (6:0-LysoPC to 10:0-LysoPC) did not affect beta-carotene uptake. The long-chain 16:0,18:1-PC increased the beta-carotene efflux from cells and drastically changed the beta-carotene UV-visible absorbance spectrum, compared with those of NoPL micelles. The acyl moieties of long-chain PC may interact with the carotenoid in the micelle interior, shifting the beta-carotene partition toward the micellar phase. Medium-chain PC and long-chain LysoPC, which have nearly equivalent hydrophobicities, may enhance beta-carotene uptake through their interaction with the cell membrane.