Carotenoid Nostoxanthin Production by Sphingomonas sp. SG73 Isolated from Deep Sea Sediment.

Carotenoids are used commercially for dietary supplements, cosmetics, and pharmaceuticals because of their antioxidant activity. In this study, colored microorganisms were isolated from deep sea sediment that had been collected from Suruga Bay, Shizuoka, Japan. One strain was found to be a pure yellow carotenoid producer, and the strain was identified as Sphingomonas sp. (Proteobacteria) by 16S rRNA gene sequence analysis; members of this genus are commonly isolated from air, the human body, and marine environments. The carotenoid was identified as nostoxanthin ((2,3,2',3')-ß,ß-carotene-2,3,2',3'-tetrol) by mass spectrometry (MS), MS/MS, and ultraviolet-visible absorption spectroscopy (UV-Vis). Nostoxanthin is a poly-hydroxy yellow carotenoid isolated from some photosynthetic bacteria, including some species of Cyanobacteria. The strain Sphingomonas sp. SG73 produced highly pure nostoxanthin of approximately 97% (area%) of the total carotenoid production, and the strain was halophilic and tolerant to 1.5-fold higher salt concentration as compared with seawater. When grown in 1.8% artificial sea salt, nostoxanthin production increased by 2.5-fold as compared with production without artificial sea salt. These results indicate that Sphingomonas sp. SG73 is an efficient producer of nostoxanthin, and the strain is ideal for carotenoid production using marine water because of its compatibility with sea salt.

Effect of astaxanthin-rich extract derived from Paracoccus carotinifaciens on the status of stress and sleep in adults.

This study investigated the effect of a dietary supplement containing astaxanthin-rich extract derived from Paracoccus carotinifaciens (astaxanthin supplement) on the status of stress and sleep in individuals aged 20-64 years. Twenty-five subjects orally administered 12 mg astaxanthin/day of astaxanthin supplement for 8 weeks (astaxanthin group) and 29 subjects given a placebo (placebo group) were evaluated with Profile of Mood States 2nd Edition for stress and Oguri-Shirakawa-Azumi Sleep Inventory for Middle-aged and Aged version for sleep. We did not observe any significant intergroup differences in the stress and sleep. A subgroup analysis was performed after dividing the subjects into two groups: those who scored >65 and those who scored ≤65 in the "Depression-Dejection" dimension of Profile of Mood States 2nd Edition. The sleep of subjects who scored >65 ("Depression-Dejection") showed significant improvement in the astaxanthin group compared with the placebo group, whereas no significant improvement was observed in stress and the other subjects. Our results indicate that people who tend to be strongly depressed may experience improved sleep after ingesting astaxanthin supplement. On the basis of the parameters tested, administration of astaxanthin supplement was not associated with any problems related to safety. Clinical registration: This study has been registered at the University Hospital Medical Information Network (https://upload.umin.ac.jp/cgi-open-bin/ctr/ctr_view.cgi?recptno=R000038619) on August 24, 2018 as "A study to evaluate the effect of intake of astaxanthin on the status of stress and sleep in adults," Identification No. UMIN000033863.

Carotenoids as natural functional pigments.

Carotenoids are tetraterpene pigments that are distributed in photosynthetic bacteria, some species of archaea and fungi, algae, plants, and animals. About 850 naturally occurring carotenoids had been reported up until 2018. Photosynthetic bacteria, fungi, algae, and plants can synthesize carotenoids de novo. Carotenoids are essential pigments in photosynthetic organs along with chlorophylls. Carotenoids also act as photo-protectors, antioxidants, color attractants, and precursors of plant hormones in non-photosynthetic organs of plants. Animals cannot synthesize carotenoids de novo, and so those found in animals are either directly accumulated from food or partly modified through metabolic reactions. So, animal carotenoids show structural diversity. Carotenoids in animals play important roles such precursors of vitamin A, photo-protectors, antioxidants, enhancers of immunity, and contributors to reproduction. In the present review, I describe the structural diversity, function, biosyntheses, and metabolism of natural carotenoids.

Effect of Oral Paprika Xanthophyll Intake on Abdominal Fat in Healthy Overweight Humans: A Randomized, Double-blind, Placebo-controlled Study.

PURPOSE: Xanthophylls that exist in various vegetables and fruits have beneficial actions, such as antioxidant activity and an anti-metabolic syndrome effect, and daily intake of xanthophylls could play an important role in preventing lifestyle-related diseases. We investigated whether intake of xanthophylls from red paprika could decrease the abdominal fat area in the healthy overweight volunteers with a body mass index (BMI) ranging from 25 to < 30 kg/m2. METHODS: In a randomized, double-blind, placebo-controlled, parallel-group study, 100 healthy volunteers were assigned to oral administration of paprika xanthophyll capsules (containing 9.0 mg of paprika xanthophylls) or placebo capsules for 12 weeks. The primary endpoint was the effect of paprika xanthophyll intake on the abdominal visceral fat area (VFA) as determined by computed tomography. The secondary endpoints were as follows: 1) changes of the abdominal subcutaneous fat area (SFA), total fat area (TFA), and BMI; 2) changes of lipid metabolism parameters, glucose metabolism parameters, and other blood parameters. RESULTS: After 12 weeks, VFA was smaller in the paprika xanthophyll group than in the placebo group. In the paprika xanthophyll group, there was a significant decrease of SFA, TFA, and BMI after 12 weeks compared with baseline, and the reduction of SFA, TFA, and BMI was significantly greater in the paprika xanthophyll group than in the placebo group. Moreover, total cholesterol and low-density lipoprotein cholesterol decreased significantly in the paprika xanthophyll group, but not in the placebo group. No adverse effects were caused by intake of paprika xanthophyll capsules. CONCLUSIONS: Intake of paprika xanthophylls for 12 weeks significantly reduced the abdominal fat area and BMI in healthy overweight volunteers without causing any adverse effects. These findings suggest that paprika xanthophyll is a safe food ingredient that improves lipid metabolism and reduces abdominal fat. TRIAL REGISTRATION: UMIN-CTR UMIN000021529.

Efficacy of Astaxanthin for the Treatment of Atopic Dermatitis in a Murine Model.

Atopic dermatitis (AD) is a common chronic inflammatory skin disease associated with various factors, including immunological abnormalities and exposure to allergens. Astaxanthin (AST) is a xanthophyll carotenoid that has recently been demonstrated to have anti-inflammatory effects and to regulate the expression of inflammatory cytokines. Thus, we investigated whether AST could improve the dermatitis and pruritus in a murine model of AD using NC/Nga mice. In addition to a behavioral evaluation, the effects of AST on the AD were determined by the clinical skin severity score, serum IgE level, histological analyses of skin, and by reverse transcription-PCR and Western blotting analyses for the expression of inflammation-related factors. AST (100 mg/kg) or vehicle (olive oil) was orally administered once day and three times a week for 26 days. When compared with vehicle-treated group, the administration of AST significantly reduced the clinical skin severity score. In addition, the spontaneous scratching in AD model mice was reduced by AST administration. Moreover, the serum IgE level was markedly decreased by the oral administration of AST compared to that in vehicle-treated mice. The number of eosinophils, total and degranulated mast cells all significantly decreased in the skin of AST-treated mice compared with vehicle-treated mice. The mRNA and protein levels of eotaxin, MIF, IL-4, IL-5 and L-histidine decarboxylase were significantly decreased in the skin of AST-treated mice compared with vehicle-treated mice. These results suggest that AST improves the dermatitis and pruritus in AD via the regulation of the inflammatory effects and the expression of inflammatory cytokines.

Accumulation of Paprika Carotenoids in Human Plasma and Erythrocytes.

The accumulation (incorporation) of paprika carotenoid in human plasma and erythrocytes was investigated. A paprika carotenoid supplement (14 mg/day) was ingested for 4 weeks by 5 young healthy volunteers (3 men and 2 women). After 2 weeks of carotenoid ingestion, the carotenoid levels in plasma and erythrocytes increased by 1.2-fold and 2.2-fold, respectively. Characteristic carotenoids found in paprika (capsanthin, cucurbitaxanthin A, and cryptocapsin) were detected in both plasma and erythrocytes. An oxidative metabolite of capsanthin (capsanthone) was also found in both plasma and erythrocytes.

Oxidative metabolites of lycopene and γ-carotene in gac (Momordica cochinchinensis).

Three new oxidative metabolites of lycopenes, (erythro)-lycopene-5,6-diol, (threo)-lycopene-5,6-diol, and 1,16-dehydro-2,6-cyclolycopene-5-ol B, and four new oxidative metabolites of γ-carotenes, 2',6'-cyclo-γ-carotene-1',5'-diol A, 2',6'-cyclo-γ-carotene-1',5'-diol B, (erythro)-γ-carotene-5,6-diol, and (threo)-γ-carotene-5,6-diol, were isolated as minor components from the aril of gac, Momordica cochinchinensis. These structures were determined on the basis of spectroscopic data, and some of them were compared to the structures of synthetic samples. Furthermore, the oxidative metabolic conversion pathways of lycopene and γ-carotene were discussed.

Accumulation of xanthophylls from the phaffia yeast (Xanthophyllomyces dendrorhrous) in calves.

An investigation into the absorption and accumulation of carotenoids from phaffia yeast in two to three-week-old calves was carried out. Carotenoid contents of the control cattle (n=1) were 615.0 ng/g in the liver, 263.7 ng/g in the duodenum, 218.0 ng/g in the pancreas, 170.0 ng/g in the blood, 140.3 ng/g in the jejunum, 115.0 ng/g in the spleen. Among the accumulated carotenoids, ß-carotene was presented as a major component (86.0 to 94.3%) along with lutein (5.7 to 14.0%) as a minor component. On the other hand, carotenoid contents in phaffia yeast-supplemented (5 g/day for one month) calves (n=3) were 4 to 10 times higher than those of the control calf. Carotenoid contents of phaffia yeast-supplemented calves were 2570.1±782 ng/g in the liver, 1806.6±1064 ng/g in the pancreas, 1648.4±630.2 ng/g in the spleen, and 1255.9±300.2 ng/g in the blood. In addition to ß-carotene, keto-carotenoids from phaffia yeast, echinenone, (3R)-3-hydroxyechinenone, and (3R,3'R)-astaxanthin, were accumulated in all organs of phaffia yeast-supplemented calves. ß-Carotene and (3R)-3-hydroxyechinenone were present as major carotenoids followed by echinenone. However, (3R,3'R)-astaxanthin, which was the major carotenoid in phaffia yeast, was found to be a minor carotenoid in calves. This indicated that calves well absorbed fewer polar xanthophylls, echinenone and (3R)-3-hydroxyechinenone compared to the polar xanthophyll, astaxanthin.

ß-Cryptoxanthin suppresses UVB-induced melanogenesis in mouse: involvement of the inhibition of prostaglandin E2 and melanocyte-stimulating hormone pathways.

OBJECTIVE: ß-cryptoxanthin (ß-CPX) is a carotenoid that is widely contained in the fruits of citrus plants. We evaluated the effect of ß-CPX on UVB-induced pigmentation and mRNA expression related to melanogenesis in mouse skin. In addition, changes in melanogenic molecules were evaluated in cultured melanocytes stimulated with prostaglandin (PG) E(2), melanocyte-stimulating hormone (MSH) and endothelin (ET)-1. METHODS: Mice were irradiated with UVB and were given ß-CPX (0.1, 1 and 10 mg/kg) orally for 14 days. Pigmentation was evaluated by skin colour change and microscopic observation. Total RNA was obtained from the skin and the expression of melanogenic mRNA was evaluated by RT-PCR. In cell culture studies, human melanocytes were cultured with ß-CPX and melanogenic stimulants (PGE(2), MSH and ET-1) for 6-10 days. Melanin contents, dendricity, melanogenic mRNA and phosphorylation of cyclic AMP response element-binding protein (CREB) were evaluated. KEY FINDINGS: ß-CPX (10 mg/kg) significantly suppressed skin pigmentation and mRNA expression of cyclooxygenase-2, ET-1 receptors, low-affinity neurotrophin receptor, PGE(2) receptor (EP1), melanocortin 1 receptor (MC1R), tyrosinase (Tyr), tyrosinase-related protein (Tyrp) 1 and microphthalmia transcription factor. ß-CPX (10 µg/ml) suppressed melanogenesis induced by PGE(2), MSH and ET-1. In the PGE(2)-stimulated melanocytes, mRNA expressions of EP-1, Tyr and Tyrp1 and phosphorylation of CREB protein were suppressed. In the ET-1-stimulated cells, only expression of CREB protein was suppressed. In the MSH-induced cells, mRNA expression of MC1R and Tyrp1 and protein expression of CREB were suppressed. CONCLUSION: Oral administration of ß-CPX was found to suppress UVB-induced melanogenesis. Suppression of melanogenic enzymes, receptors of melanogenic stimulators, expression and phosphorylation of CREB are thought to be involved in the mechanism.

Pharmacokinetics of fucoxanthinol in human plasma after the oral administration of kombu extract.

Dietary fucoxanthin has been reported to exert several physiological functions, and fucoxanthinol is considered to be the primary active metabolite of fucoxanthin. However, there is no information about the pharmacokinetics of fucoxanthinol in human subjects. In the present study, eighteen human volunteers were orally administered kombu extract containing 31 mg fucoxanthin, and their peripheral blood was collected 5 min before and 0·5, 1, 2, 4, 8 and 24 h after the treatment. Plasma fucoxanthinol concentrations were measured by HPLC, and the pharmacokinetics of fucoxanthinol were as follows: maximum concentration, 44·2 nmol/l; time at maximum concentration, 4 h; terminal half-time, 7·0 h; area under the curve (AUC) for 1-24 h, 578·7 nmol/l × h; AUC(∞), 663·7 nmol/l × h. In addition to fucoxanthinol, we also attempted to detect amarouciaxanthin A, a hepatic metabolite of fucoxanthinol, using HPLC, but it was not present in the volunteers' plasma. On the other hand, a peak that was suspected to represent the cis-isomer of fucoxanthinol was found in the HPLC chromatogram. By comparing the present results with those of a previous study using mice, we found that the bioavailability and metabolism of fucoxanthinol differ between human subjects and mice.

Functional compounds in fermented buckwheat sprouts.

Fermented buckwheat sprouts (FBS) are used as multifunctional foods. Their production process includes fermentation with lactic acid bacteria. The major strains were found to include Lactobacillus plantarum, Lactobacillus brevis, Lactobacillus pentosus, Lactococcus lactis subsp. lactis, and Pediococcus pentosaceus in an investigation of the lactic acid bacteria. We searched for the functional components, and nicotianamine (NA) and 2″-hydroxynicotianamine (HNA) were identified as angiotensin I-converting enzyme (ACE) inhibitors. NA and HNA increased during fermentation. Indole-3-ethanol was identified as an antioxidant (a SOD active substance), and may have been generated from tryptophan during fermentation because it was not contained in green buckwheat juice. A safety test demonstrated that FBS contained were safe functional food components, showing negative results in buckwheat allergy tests. Any buckwheat allergy substances might have been degraded during the fermentation process.

New chromone derivative terminalianone from African plant Terminalia brownii Fresen (Combretaceae) in Tanzania.

A new chromone derivative named terminalianone (1) was isolated from the African plant, Terminalia brownii Fresen (Combretaceae) in Tanzania. Its structure was determined to be 7-hydroxy-3-[6'-hydroxyphenyl-2'-oxo-ethyl]chromone by FAB-MS and NMR spectral data.

Anti-pigmentary activity of fucoxanthin and its influence on skin mRNA expression of melanogenic molecules.

OBJECTIVES: Carotenoids and retinoic acid derivatives are topically applied for sun-protective and whitening purposes. Fucoxanthin is a carotenoid derived from edible sea algae, but its effect on melanogenesis has not been established. Therefore, we examined the effect of fucoxanthin on melanogenesis. METHODS: Inhibitory effects on tyrosinase activity, melanin formation in B16 melanoma and skin pigmentation in UVB-irradiated guinea-pigs were evaluated. To elucidate the action of fucoxanthin on melanogenesis, its effect on skin melanogenic mRNA expression was evaluated in UVB-irradiated mice. Fucoxanthin was given topically or orally to mice once a day and UVB irradiation was applied for 14 days. The effect of fucoxanthin on skin melanogenic mRNA expression was evaluated by real time reverse transcription polymerase chain reaction. KEY FINDINGS: Fucoxanthin inhibited tyrosinase activity, melanogenesis in melanoma and UVB-induced skin pigmentation. Topical application of fucoxanthin (1%) significantly suppressed mRNA expression of cyclooxygenase (COX)-2, endothelin receptor A, p75 neurotrophin receptor (NTR), prostaglandin E receptor 1 (EP1), melanocortin 1 receptor (MC1R) and tyrosinase-related protein 1. The suppression of p75NTR, EP1 and MC1R expressions was observed at 0.01% application. Also, oral application of fucoxanthin (10 mg/kg) significantly suppressed expression of COX-2, p75NTR, EP1 and MC1R. CONCLUSIONS: These results suggest that fucoxanthin exhibits anti-pigmentary activity by topical or oral application in UVB-induced melanogenesis. This effect of fucoxanthin may be due to suppression of prostaglandin (PG) E(2) synthesis and melanogenic stimulant receptors (neurotrophin, PGE(2) and melanocyte stimulating hormone expression).

Straightforward approach to the discrimination of (4R)- and (4S)-beta-isocryptoxanthin from a conformationally insensitive CD band.

A straightforward strategy is reported for chiral discrimination in a specified carotenoid using a CD band, which is insensitive to conformational changes, computed by quantum chemical calculation.

Bioavailability of astaxanthin in Haematococcus algal extract: the effects of timing of diet and smoking habits.

Astaxanthin is a caroteonid that possesses strong antioxidant activity. Recently, many studies on biological activity have been reported. In general, the absorption of carotenoids is affected greatly by diet and by smoking. In this report, we investigated astaxanthin pharmacokinetics after administration of Haematococcus algal extract, a source of astaxanthin, to smokers and nonsmokers before and after a meal; astaxanthin was given before the meal to nonsmokers (n = 7), after the meal to nonsmokers (n = 6), and after the meal to smokers (n = 7), then serum samples were analyzed. The timing of administration greatly affected astaxanthin bioavailability including the area under the curve (AUC(0-168), 2,968 + or - 959 microg h/l in the before-meal group vs. 7,219 + or - 3,118 microg h/l in the after-meal group), indicating high availability in the after-meal group. Smoking also affected the pharmacokinetic parameters and reduced the half-life (t(1/2)) of astaxanthin elimination significantly.

Effects of dietary supplementation of ferulic acid and gamma-oryzanol on integument color and suppression of oxidative stress in cultured red sea bream, Pagrus major.

The effects of ferulic acid (FA) and gamma-oryzanol (OZ) supplementation on cultured red sea bream were examined. Commercial brown fish meal diets supplemented with FA (0.01-0.5%) or OZ (0.05-0.5%) were given to zero-year, cultured red sea bream for 98 days. After the experiment, the brightness of the integument color ("L" value) of FA- and OZ-administrated fish was higher than that of control fish. Furthermore, 2-Thiobarbituric acid reactive substances (TBARS) in the liver of FA- and OZ-administrated fish was lower than in control fish. These results indicate that FA and OZ suppressed not only dark-color pigmentation but also oxidative stress in cultured red sea bream.

Analysis of carotenoid composition in petals of calendula (Calendula officinalis L.).

Nineteen carotenoids were identified in extracts of petals of orange- and yellow-flowered cultivars of calendula (Calendula officinalis L.). Ten carotenoids were unique to orange-flowered cultivars. The UV-vis absorption maxima of these ten carotenoids were at longer wavelengths than that of flavoxanthin, the main carotenoid of calendula petals, and it is clear that these carotenoids are responsible for the orange color of the petals. Six carotenoids had a cis structure at C-5 (C-5'), and it is conceivable that these (5Z)-carotenoids are enzymatically isomerized at C-5 in a pathway that diverges from the main carotenoid biosynthesis pathway. Among them, (5Z,9Z)-lycopene (1), (5Z,9Z,5'Z,9'Z)-lycopene (3), (5'Z)-gamma-carotene (4), and (5'Z,9'Z)-rubixanthin (5) has never before been identified. Additionally, (5Z,9Z,5'Z)-lycopene (2) has been reported only as a synthesized compound.

Structure of new carotenoids with the 6-oxo-kappa end group from the fruits of paprika, Capsicum annuum.

New carotenoids 1 and 2 were isolated as minor components from the ripe fruits of paprika (Capsicum annuum). The structures of 1 and 2 were determined to be (3R,5'R)-3-hydroxy-beta,kappa-caroten-6'-one and (5'R)-3,4-didehydro-beta,kappa-caroten-6'-one, respectively, from UV-vis, NMR, CD, HRFABMS, and FABMS/MS spectra.

Astaxanthin limits exercise-induced skeletal and cardiac muscle damage in mice.

Dietary antioxidants may attenuate oxidative damage from strenuous exercise in various tissues. Beneficial effects of the antioxidant astaxanthin have been demonstrated in vitro, but not yet in vivo. We investigated the effect of dietary supplementation with astaxanthin on oxidative damage induced by strenuous exercise in mouse gastrocnemius and heart. C57BL/6 mice (7 weeks old) were divided into groups: rested control, intense exercise, and exercise with astaxanthin supplementation. After 3 weeks of exercise acclimation, both exercise groups ran on a treadmill at 28 m/min until exhaustion. Exercise-increased 4-hydroxy-2-nonenal-modified protein and 8-hydroxy-2'-deoxyguanosine in gastrocnemius and heart were blunted in the astaxanthin group. Increases in plasma creatine kinase activity, and in myeloperoxidase activity in gastrocnemius and heart, also were lessened by astaxanthin. Astaxanthin showed accumulation in gastrocnemius and heart from the 3 week supplementation. Astaxanthin can attenuate exercise-induced damage in mouse skeletal muscle and heart, including an associated neutrophil infiltration that induces further damage.

New bis-secolabdane diterpenoids from Excoecaria agallocha.

Two new bis-secolabdane diterpenoids, excoecarins R1 (1) and R2 (2), were isolated from the resinous wood of Excoecaria agallocha. The structures of 1 and 2 were established on the basis of spectroscopic data interpretation and chemical evidence.