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Tyrosinase Inhibitor from Black Rice Bran
Abstract
The inhibitor of tyrosinase activity in black rice bran was investigated. The methanol extract from black rice bran was re-extracted with hexane, chloroform, ethyl acetate, or water. The ethyl acetate extract had the most potent inhibition against tyrosinase activity by 80.5% at a concentration of 0.4 mg/mL. Inhibitory compound in the ethyl acetate fraction was isolated by silica gel column chromatography, and identified as protocatechuic acid methyl ester (compound 1) by GC, GC-MS, IR, and 1H and 13C NMR spectroscopy. Compound 1 inhibited 75.4% of tyrosinase activity at a concentration of 0.50 micromol/mL. ID(50) (50% inhibition dose) value of compound 1 was 0.28 micromol/mL. To study the structure-activity relationship, protocatechuic acid (2), vanillic acid (3), vanillic acid methyl ester (4), isovanillic acid (5), isovanillic acid methyl ester (6), veratric acid (7), and veratric acid methyl ester (8) were also assayed.
... Phenolic acids such as coumaric, sinapic and ferulic acids were reported to be positively correlated with the antioxidant capacity and tyrosinase inhibitory activity of fermented rice extracts [10]. A previous study identified protocatechuic methyl ester and protocatechuic acid in black rice bran extracts as being responsible for tyrosinase inhibition [11]. Flavonoids also act as strong antioxidants by donating electrons or hydrogen atoms to free radicals, delocalizing the unpaired electrons of the free radicals, and chelating metal ions [8]. ...
In the modern cosmetics industry, there exists a major trend for replacement of synthetic chemicals with plant-based ingredients in skincare formulation. This research aimed to assess the efficiency of different methods to extract bioactive compounds (as measured by total phenolic content; TPC and total flavonoid content; TFC) responsible for three important cosmeceutical properties (antioxidation, anti-tyrosinase, and anti-elastase) from selected rice grains. The grains of two varieties of purplish-black rice (Neaw Leum Pua; NLP) and black rice (Hom Nil; HN) were extracted with phosphate buffered saline (PBS) and then supplementary treated with sonication, heating, and proteolytic enzyme digestion or fermented with Aspergillus niger. The results showed that sonication slightly enhanced TPC and TFC, but significantly increased antioxidant capacity and anti-tyrosinase activity. The high temperature of 60℃ and 100℃ significantly increased antioxidant capacity based on FRAP assay but reduced that based on DPPH radical scavenging assay. Anti-tyrosinase activity was enhanced by high temperature but that of anti-elastase was inhibited. The addition of papain to the seed extracts slightly enhanced anti-elastase and anti-tyrosinase activity. Notably, fermented rice grains exhibited much greater yields of TPC and TFC, and higher biochemical activities than other methods. The fermented rice exhibited the highest TFC after 3 days; the highest TPC, antioxidant capacity, and tyrosinase inhibition after 6 days; and the highest elastase inhibition activity after 9 days. Therefore, fermentation was the most promising technique to enhance all three desirable properties for cosmetic ingredients when pigmented rice was used as the raw material.
... This inhibitory effect was found to be even stronger than that of arbutin (with an IC50 concentration of 0.52 mg/mL). The protocatechuic acid methyl ester from the extracts of black rice bran inhibited 75.4% of tyrosinase activity at 0.5 µmol/mL [44]. The IC50 values of the extract from defatted rice bran were 0.99 mg/mL for monophenolase activity and 1.92 mg/mL for diphenolase activity, which were equivalent to the standard arbutin with no significant difference [45]. ...
Hot air-assisted radio frequency (HARF) is considered a rapid heating process. In order to improve the circular economy of agricultural byproducts, this study used different proportions of HARF stabilized rice bran (R) from milling rice, HARF dried ginseng residue (G) from ultrasonic extraction, and peanut residue (P) from HARF roasting and oil extraction as the Hericium erinaceus solid-state fermented media. Then, the whitening effects of water extracts from media and fermented products were analyzed. First, the surface temperature of 1 kg rice bran exceeded 90 °C after 3 min of 5 kW HARF heating, effectively deactivating lipase. The combinations of 1 kg of rice bran with 0.5, 1, 1.5, and 2 kg of ginseng residue (85% moisture content) were dried using 5 kW HARF. Each of the drying rates was about 27 g/min, and the drying periods were 14, 30, 46, and 62 min, respectively, which were used to reduce the moisture content below 10%. Compared to traditional air drying for ginseng residue, HARF drying may save up to 96% of time and 91% of energy consumption. Then, the ratio of dried R, G, and P was 4:1:1, mixed with 45% moisture as solid-state media for Hericium erinaceus and 5 weeks of cultivation at 25 °C. In comparison to the control group, the water extracts at 100 µg/mL from media R4G1, R4G1P1, and fermented HER4G1P1 products exhibited tyrosinase inhibition of 29.7%, 52.4%, and 50.7%, respectively. These extracts also reduced the relative melanin area of 78 hpf zebrafish embryos by 21.57%, 40.20%, and 58.03%, respectively. Therefore, HARF can quickly dry agricultural byproducts as media for Hericium erinaceus solid-state fermentation while also providing a significant whitening effect for cosmetic applications.
... Some of the bioactive components of rice have been investigated for the treatment of diabetes mellitus (Sansenya et al., 2021). Due to their anti-melanin production properties, such as suppression of tyrosinase activity, several bioactive compounds from rice have also found use in cosmetic products (Miyazawa et al., 2003). Rice is used as a food source and a medical therapy in many countries. ...
Rice contains many bioactive compounds that perform various biological activities. Some of these compounds have been identified as -glucosidase and -amylase inhibitors, including guaiacol, vanillin, methyl vanillate, vanillic acid, syringic acid, and 2-pentyl furan. In this study, we assessed the growth rate, photosynthetic pigment content, phenolic content , and flavonoid content of gamma-irradiated Thai pigmented rice. Bioactive components of gamma-irradiated rice that had been subjected to salt treatment were also investigated. The findings showed that production of photosynthetic pigments , which are associated with plant growth, was induced by low gamma exposure. Phenolic and flavonoid content of rice was increased after gamma irradiation at 5 to 1,000 Gy. Both gamma irradiation and the salt conditions changed the quantity of vanillin, methyl vanillate, and vanillic acid in the rice. However, at a salt concentration of 40 mM, the salt stress had more of an effect than the gamma dosage. However, the high concentrations of methyl vanillate and vanillic acid detected in the rice under salt conditions were ameliorated by gamma irradiation. Guaiacol served as the substrate of guaiacol perox-idase for catalyzed reactive oxygen species, as evidenced by the observation that the guaiacol content of rice decreased between increased gamma dosages. A gamma dose of 40 to 1,000 Gy resulted in the production of syringic acid. Under salt stress, syringic acid buildup was also seen to be ameliorated by gamma irradiation. In comparison to salt conditions, particularly for 20 mM salt, gamma irradiation had less of an impact on the 2-pentyl furan in rice.
... Tyrosinase is also responsible for the enzymatic browning of plant foods [13]. Scientists pay special attention to phytochemicals to treat dermatological disorders in the medical field and their skin whitening potential in cosmetics [14]. ...
Onosma species have been used by the public for centuries to treat various diseases. This study aimed to analyze the chemical composition, antioxidant, and enzyme inhibitory activity potentials of the methanol extracts of O. cappadocica and O. rutilum, endemic to Turkish flora. The chemical compositions of the extracts were determined by using spectrophotometric and chromatographic methods. The biological activities of the extracts were determined by using antioxidant and enzyme inhibitory test systems. It was determined that the extracts contain high amounts of hesperidin, hyperoside, and rosmarinic acid. While O. rutilum exhibited higher activity in phosphomolybdenum, ABTS radical scavenging and ferrous ion chelating assays, reducing power, and DPPH radical scavenging tests resulted in the superiority of O. cappadocica. O. rutilum exhibited higher inhibition activity on all enzymes (acetylcholinesterase, butyrylcholinesterase, tyrosinase, and a-amylase), except for a-glucosidase. It was concluded that the extracts in question could be used as alternative agents in the food, cosmetic and medical industries due to their antioxidant and enzyme inhibitory activities.
... In order to prevent pigmentation and browning, tyrosinase inhibitors from natural sources such as plants, mushrooms, rhizomes or marine algae can be used not only for food applications but also as skin antipigmentation agents. Kojic acid, among other wellknown tyrosinase inhibitors such as hydroquinone and azelaic acid, has been reported and tested as a cosmetic and pharmaceutical ingredient to be used to prevent melanin overproduction in epidermal layers of the skin (Miyazawa et al., 2003). Previous studies also reported the enhancement of tyrosinase inhibition activity of samples through fungal fermentation (Jamaluddin et al., 2014;Wu et al., 2018). ...
This study was carried out to evaluate the tyrosinase inhibition activity, which represents anti-pigmentation/browning property and bioactive compounds of sub-fractions of Schizophyllum commune extracts. In this study, two types of crude extracts, namely K4C and K30C, were subjected to chromatographic fractionation in vacuum column chromatography packed with silica gel. The columns were stepwise eluted with different ratios of solvent acetone: methanol (A:M) to obtain several fractions. Anti-pigmentation activity was measured by tyrosinase inhibition assay. The fraction with the highest activity for K4C extract was 7A:3M (30.46±3.22%) while fraction 100M (34.32±2.14%) was the highest for K30C extract. Biological components such as organic acids, amino acids, as well as phenolic acids were also assessed by ultra and high-performance liquid chromatography (UPLC and HPLC). The results revealed that the amounts of bioactive compounds were varied; the major organic acids detected were citric acid (313.142±1.069 mg/L), tartaric acid (37.656±8.807 mg/L) and L-malic (23.748±2.565 mg/L) in the fraction K4C-7A:3M compared to fraction K30C-100M. The same fraction showed the highest amount of amino acids while phenolic acids were detected in low amounts in K4C -7A:3M and K30C-100M fractions. The fraction with the highest biological activity has the potential to be used as a bio-ingredient in food applications and nutricosmetic product formulations. The potential product derived from this project may diversify mushroombased downstream products available in Malaysia, and subsequently further expand our mushroom industry.
... However, hyperpigmentation i.e., melanin accumulation in the skin paves the way for numerous skin ailments like freckles, age spots, melasma, etc. (Karioti et al., 2007). The browning in foods associated with quality losses and disorder due to hyperpigmentation in human skin can be effectively controlled with therapeutic agents like tyrosinase inhibitors (Miyazawa et al., 2003). With emerging trends, a lighter skin tone is preferable further boosting the ever-growing cosmetic industries (Ko et al., 2014). ...
Background
Kaempferia galanga (L.) is one of the prospective therapeutic plants with an aromatic rhizome, and belongs to the Zingiberaceae family. This herb is commonly used by local practitioners in traditional Asian medicine.
Methods
In the present investigation, the novel Kaempferia galanga rhizome essential oil rich in ethyl p-methoxy cinnamate (EMCKG) was evaluated using GC/MS for chemical composition analysis. EMCKG was analyzed for its possible antimicrobial, neurodegenerative inhibitory, acetylcholinesterase, anti-inflammatory, and antioxidant activities as well as for the genotoxic effects using the standard methodologies. ANOVA and post hoc was performed to test the statistical significance of the study.
Results
GC/MS analysis identified ethyl p-methoxy cinnamate as the major component of EMCKG essential oil with an area percentage of 66.39%. The EMCKG exhibited moderate (DPPH assay IC 50 = 15.64 ± 0.263 µg/mL; ABTS assay IC 50 = 16.93 ± 0.228 µg/mL) antioxidant activity than standard ascorbic acid (DPPH assay IC 50 = 21.24 ± 0.413 µg/mL; ABTS assay IC 50 = 21.156 ± 0.345 µg/mL). Similarly, EMCKG showed comparable activity in albumin denaturation (IC 50 = 2.93 ± 0.59 µg/mL) and protease inhibitor assay (IC 50 = 17.143 ± 0.506 µg/mL) to that of standard sodium diclofenac (IC 50 = 23.87 ± 0.729 µg/mL and IC 50 = 19.18 ± 0.271 µg/mL, respectively). The EMCKG exhibited a dose-dependent antimicrobial activity pattern with the highest inhibitory activity at 500 µg/mL against Staphylococcus aureus and considerable anticholinesterase activities (IC 50 = 21.94 ± 0.109 µg/mL) compared to the standard galanthamine (IC 50 = 27.18 ± 0.511 µg/mL). EMCKG also showed strong anti-diabetic activity (IC 50 = 18.503 ± 0.480 µg/mL) and anti-tyrosinase activity (IC 50 = 14.756 ± 0.325 µg/mL) as compared to the standards used (acarbose IC 50 = 20.39 ± 0.231 µg/mL and kojic acid IC 50 = 17.73 ± 0.192 µg/mL) in the study. Genotoxicity analysis of EMCKG revealed that at 1 µg/mL concentration has no toxic effects in mitosis of Allium cepa roots (Mitotic Index MI = 13.56% and chromosomal aberration CA = 07.60%). The ANOVA confirmed that except for the anticholinesterase activity, there is insignificant difference for essential oil and standards used for all the other bioactivities thus confirming their interchangeable applicability.
Conclusions
Current research provides the basis for the fact that besides being a rich source of ethyl p-methoxycinnamate, EMCKG has the potential for future formulation and development of an inexpensive skin-care agent and for the preparation of anti-diabetic drugs.
... Plant extracts rich in benzaldehyde and benzoate derivatives have a weak-to-moderate tyrosinase inhibitory activity; examples of these compounds include benzoic acid, benzaldehyde, anisic acid, anisaldehyde, cinnamic acid, and methoxycinnamic acid from the roots of Pulsatilla cernua [61]; 4-benzaldehydes from cumin [62]; p-coumaric acid from the leaves of Panax ginseng [63]; hydroxycinnamoyl derivatives from green coffee beans [64]; and vanillic acid and its derivatives from black rice bran [65]. Their inhibitory mechanism can be through Schiff bases with a primary amino group in the enzyme or by copper chelating mechanism [66,67]. ...
The sugarcane processing industry generates a large amount of straw, which has a negative environmental impact, and high costs are associated with their elimination, wasting their potential bioactive value attributed to their richness in polyphenols. In this study, an ethanolic extract produced from sugarcane straw was screened for its phenolic compounds content, and the potential use of this extract in the development of a food ingredient was further evaluated. Fifty different secondary metabolites belonging to the hydroxybenzoic acids, hydroxycinnamic acids, and flavonoids were identified by liquid chromatography–electrospray ionization–ultrahigh-resolution—quadrupole time of flight–mass spectrometry (LC-ESI-UHR-QqTOF-MS). The predominant phenolic compounds found were 4-hydroxybenzaldehyde, chlorogenic acid, and 5-O-feruloylquinic acid. The obtained extracts showed strong potential as food preservatives by exhibiting (a) antioxidant activity using both 2.2′-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt radical cation (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) methods; and (b) antimicrobial capacity, with a minimum inhibitory concentration of 50 mg/mL for Staphylococcus aureus, 74% inhibition for Bacillus cereus, and 44% for Salmonella enterica; and (c) the capacity to inhibit a food browning enzyme, tyrosinase (28–73% for 1–8 mg/ mL). Moreover, the extracts showed antidiabetic potential by inhibiting the enzymes α-glucosidase (15–38% for 1.25–5.00 mg/mL) and dipeptidyl peptidase-IV (DPP-IV) (62–114% for 0.31–5.00 mg/mL). The extract (0.625 mg/mL) also exhibited the capacity to reduce proinflammatory mediators (i.e., interleukins 6 and 8, and tumor necrosis factor alpha) when Caco-2 cells were stimulated with interleukin 1 beta. Thus, sugarcane straw extract, which is rich in phenolic compounds, showed high potential to be used in the development of food-preservative ingredients owing to its antioxidant and antimicrobial potential, and to be explored as a food supplement in diabetes prevention and as coadjuvant to reduce intestinal inflammation by reducing proinflammatory mediators.
... Benzoic acid and derivatives [86] (benzaldehyde [150], benzoic acid [151], anisic acid [152], anisaldehyde [153], cinnamic acid [154], methoxycinammic acid [155], and vanillic acid [156] also perform anti-Tyr potency through different mechanisms, though lower tan kojic acid. Benzaldehyde compounds, when interacting with the amino groups of Tyr, produce a Schiff base [157], whereas benzoate compounds chelate the copper ions in Tyr's active site, leading to its inhibition [158]. ...
Natural products bear a multivariate biochemical profile with antioxidant, anti-inflammatory, antibacterial, and antitumoral properties. Along with their natural sources, they have been widely used both as anti-aging and anti-melanogenic agents due to their effective contribution in the elimination of reactive oxygen species (ROS) caused by oxidative stress. Their anti-aging activity is mainly related to their capacity of inhibiting enzymes like Human Neutrophil Elastase (HNE), Hyaluronidase (Hyal) and Tyrosinase (Tyr). Herein, we accumulated literature information (covering the period 1965–2020) on the inhibitory activity of natural products and their natural sources towards these enzymes. To navigate this information, we developed a database and server termed ANTIAGE-DB that allows the prediction of the anti-aging potential of target compounds. The server operates in two axes. First a comparison of compounds by shape similarity can be performed against our curated database of natural products whose inhibitory potential has been established in the literature. In addition, inverse virtual screening can be performed for a chosen molecule against the three targeted enzymes. The server is open access, and a detailed report with the prediction results is emailed to the user. ANTIAGE-DB could enable researchers to explore the chemical space of natural based products, but is not limited to, as anti-aging compounds and can predict their anti-aging potential. ANTIAGE-DB is accessed online.
... Tyrosinase is the key enzyme that regulates the biosynthesis of melanin. Recently, the potential application of tyrosinase inhibitors to improve food quality and prevent pigmentation disorders has become important [44,45]. In the antityrosinase assay, the acetone extract of Morus alba L. exhibited stronger tyrosinase inhibitory activity than the positive control, arbutin. ...
The root bark of Morus alba L. (Mori Cortex) is used to treat diuresis and diabetes in Chinese traditional medicine. We evaluated different solvent extracts and bioactive components from the root bark of Morus alba L. for their antioxidant, anti-α-glucosidase, antityrosinase, and anti-inflammatory activities. Acetone extract showed potent antioxidant activity, with SC50 values of 242.33 ± 15.78 and 129.28 ± 10.53 µg/mL in DPPH and ABTS radical scavenging assays, respectively. Acetone and ethyl acetate extracts exhibited the strongest anti-α-glucosidase activity, with IC50 values of 3.87 ± 1.95 and 5.80 ± 2.29 μg/mL, respectively. In the antityrosinase assay, the acetone extract showed excellent activity, with an IC50 value of 7.95 ± 1.54 μg/mL. In the anti-inflammatory test, ethyl acetate and acetone extracts showed significant anti-nitric oxide (NO) activity, with IC50 values of 10.81 ± 1.41 and 12.00 ± 1.32 μg/mL, respectively. The content of the active compounds in the solvent extracts was examined and compared by HPLC analysis. Six active compounds were isolated and evaluated for their antioxidant, anti-α-glucosidase, antityrosinase, and anti-inflammatory properties. Morin (1) and oxyresveratrol (3) exhibited effective antioxidant activities in DPPH and ABTS radical scavenging assays. Additionally, oxyresveratrol (3) and kuwanon H (6) showed the highest antityrosinase and anti-α-glucosidase activities among all isolates. Morusin (2) demonstrated more significant anti-NO and anti-iNOS activities than the positive control, quercetin. Our study suggests that the active extracts and components from root bark of Morus alba should be further investigated as promising candidates for the treatment or prevention of oxidative stress-related diseases, hyperglycemia, and pigmentation disorders.
... HMBC correlations ( Figures 5 and S33) between H-2' and the carbon at δ 80.5 (C-2), 198.2 (C-4'), 70.5 (C-1'), and 30.9 (C-6') and between H-3' and carbons at δ 70.5 (C-1') and 33.9 (C-5') supposed the connectivity between the non-aromatic B-ring and C-ring. According to the above evidence, the structure of 4 was elucidated as 4-hydroxy-4-(7-methoxy-8methylchroman-2-yl)-cyclohex-2-enone, which was further confirmed by COSY ( Figure S30), NOESY ( Figures 5 and S31), 13 (26) [42], kukulkanin B (27) [42]; 3 chromones, noreugenin (28) [43] and 5,7-dihydroxy-2,8-dimethylchromen-4-one (29) [44], 5,7-dihydroxy-2-tricosylchromone (30) [45]; 15 aromatics, 1H,3H-5,7-dimethoxyisobenzofuran-l-one (31) [46], syringic acid (32) [47], 2,4-dimethoxy-6-methylbenzoic acid (33) [48], methyl 2,6-dihydroxy-3,4-dimethylbenzoate (34) [49], methyl 3,4-dihydroxybenzoate (35) [50], 3,5-dimethoxy-4-hydroxybenzaldehyde (36) [51], vanillic acid (37) [52], methyl 2,4-dimethoxy-6-methylbenzoate (38) [48], methyl 4-hydroxy-2-methoxy-6-methylbenzoate (39) [53], methyl 4-hydroxybenzoate (40) ...
Dianella ensifolia is a perennial herb with thickened rhizome and is widely distributed in tropical and subtropical regions of Asia, Australia, and the Pacific islands. This plant has the potential to be used as a source of herbal medicine. This study investigated further phytochemistry and tyrosinase inhibitory effect of some constituents isolated from D. ensifolia. Four new flavans, (2S)-4’-hydroxy-6,7-dimethoxyflavan (1), (2S)-3’,4’-dihydroxy-7-methoxy-8-methylflavan (2), (2S)-2’-hydroxy-7-methoxyflavan (3), and (2S,1′S)-4-hydroxy-4-(7-methoxy-8-methylchroman-2-yl)-cyclohex-2-enone (4), together with 67 known compounds, including 10 flavans (5–14), 5 flavanones (15–19), 3 flavone (20–22), 5 chalcones (23–27), 3 chromones (28–30), 15 aromatics (31–45), 7 phenylpropanoids (46–52), one lignan (53), 7 steroids (54–60), one monoterpene (61), one diterpene (62), 4 triterpenes (63–66), a carotenoid (67), 2 alkaloids (68 and 69), and 2 fatty acids (70 and 71) were isolated from D. ensifolia. Their structures were elucidated on the basis of physical and spectroscopic data analyses. Moreover, compounds 1–4, 8, 10–15, 20, 21, and 41 were evaluated for their mushroom tyrosinase inhibitory effect. Compounds 11 and 14 strongly inhibited mushroom tyrosinase activity with IC50 values of 8.6 and 14.5 μM, respectively.
... Antosianin diketahui mampu secara kuat mengabsorbsi spektrum sinar ultraviolet dan sinar tampak dengan absorbansi berkisar 500-550 nm dan 280-320 nm. Kemampuan antosianin yang dapat meningkatkan adsorpsi radiasi UVB memungkinkan potensi sebagai aktivitas inhibitor tirosinase yang tinggi (Miyazawa et al., 2003;Rojo et al., 2013). Tirosinase merupakan enzim utama yang bertanggung jawab pada biosintesis melanin dan efektif dalam melindungi kerusakan kulit yang disebabkan oleh radiasi sinar ultraviolet (Jung et al., 2019). ...
Beras telah lama dimanfaatkan sebagai bahan dasar sediaan kecantikan. Sediaan kecantikan tradisional yang berbahan dasar beras banyak digunakan untuk perawatan kulit seperti masker, bedak dingin dan scrub. Salah satu beras yang dimanfaatkan di Indonesia yaitu beras merah (Oryza nivara). Senyawa antosianin dalam beras merah merupakan senyawa polifenol yang diketahui dapat melindungi kulit dari radiasi sinar ultraviolet, mampu meningkatkan jumlah kolagen, elastin, maupun asam hialuronat pada kulit manusia. Artikel ini mengkaji beberapa artikel ilmiah yang meneliti ekstrak beras merah yang digunakan sebagai sediaan farmasi, khususnya dalam perawatan kulit. Tujuan kajian artikel dimaksudkan untuk menyediakan informasi ilmiah terkait aplikasi penggunaan ekstrak beras merah sebagai sediaan perawatan kulit. Hasil dari kajian artikel ini menunjukkan bahwa ekstrak beras merah dapat diaplikasikan menjadi sediaan perawatan kulit berupa losio tabir surya, krim, masker peel off, sabun antibakteri, body butter, dan body scrub.
... The major enzyme for melanogenesis in epidermal layers is tyrosinase (phenol oxidase), and a variety of tyrosinase inhibitors are developed and introduced in cosmeceutical preparations to minimize the excessive production of melanin [34]. The mechanism of mushroom tyrosinase assay involves the formation of L-dopa as a result of L-tyrosine hydroxylation [35]. ...
Antioxidants from natural sources are extensively attaining consideration to avert the skin
from damage and aging caused by free radicals. Flaxseed (Linum usitatissimum L.), a natural therapeutic agent was meant to be explored cosmeceutical by quantifying its potential phytoconstituents and to be incorporated into a microemulgel for topical use. Hydroalcoholic fractions (both methanolic and ethanolic; 80%) flaxseed extracts were subjected to phytochemical screening by quantifying total phenolic content (TPC), total flavonoid content (TFC), and high-performance liquid chromatography-ultraviolet (HPLC-UV); and for biological activities through 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, tyrosinase inhibition assay, and sun protection factor (SPF). Ethanolic fraction was selected for further study by TPC (18.75 mg gallic acid equivalent/g), and TFC (1.34 mg quercetin equivalent/g). HPLC-UV analysis showed the existence of benzoic, quercetin, caffeic, vanillic, p-coumaric, gallic, cinnamic, syringic and sinapic acids. Biological activities showed 87.00%, 72.00% and 21.75 values for DPPH assay, tyrosinase inhibition and SPF assays, respectively. An oil-in-water (OW) microemulsion containing the flaxseed extract, with 99.20 nm Zeta size, -19.3 Zeta potential and 0.434 polydispersity index was developed and incorporated in Carbopol-940 gel matrix to formulate an active microemulgel with 59.15% release in in-vitro studies. The successfully formulated stable active microemulgel produced statistically significant effects (p < 0.05), in comparison to a placebo, on skin erythema, melanin, sebum, moisture and elasticity, in a non-invasive in-vivo study performed on 13 healthy human female volunteers. Other cosmeceutical products can also be formulated from flaxseed, making it a considerable candidate for further utilization in the pharmaceutical industry.
... Additionally, it was appeared that increasing the chain length above two carbon atoms changed the type of braking from competitive to non-competitive 93 . (22) Another study 94 determined the effect of methoxylation of hydroxyl groups on the tested acids' activity and their esters. Protocatechuic acid methyl ester, protocatechuic acid, vanillic acid methyl ester, vanillic acid, isovanillic acid methyl ester, isovanillic acid, veratric acid methyl ester, and veratric acid were used in the study. ...
Human has used plants to treat many civilisation diseases for thousands of years. Examples include reserpine (hypertension therapy), digoxin (myocardial diseases), vinblastine and vincristine (cancers), and opioids (palliative treatment). Plants are a rich source of natural metabolites with multiple biological activities, and the use of modern approaches and tools allowed finally for more effective bioprospecting. The new phytochemicals are hyaluronidase (Hyal) inhibitors, which could serve as anti-cancer drugs, male contraceptives, and an antidote against venoms. In turn, tyrosinase inhibitors can be used in cosmetics/pharmaceuticals as whitening agents and to treat skin pigmentation disorders. However, the activity of these inhibitors is stricte dependent on their structure and the presence of the chemical groups, e.g. carbonyl or hydroxyl. This review aims to provide comprehensive and in-depth evidence related to the anti-tyrosinase and anti-Hyal activity of phytochemicals as well as confirming their efficiency and future perspectives.
... Rice bran, an abundant rice mill by-product containing gamma oryzanol, could be used as a skin brightening agent (3). Miyazawa et al. (7) reported that 0.4 mg/ml black rice bran extract inhibited tyrosinase activity by 80.5%. The dry black rice bran (Oryza sativa L. indica) contained 118.572 mg/g of gamma oryzanol, and the extract inhibited tyrosinase activity at an IC50 of 74.8 µg/mL (8). ...
Background: Ultraviolet exposure is an extrinsic factor to initiate melanogenesis, the process of melanin formation in the skin. Nowadays, natural ingredients tend to be more prevalent in cosmetic formulations due to consumers’ concern about synthetic ingredients and the risks they may represent for human health. Rice bran, the outer layer of a rice grain, can be utilized as a skin-lightening agent. Objectives: This study aimed to determine the efficacy of a lotion containing black rice bran (Oryza sativa L. indica) ethanolic extract as a skin lightening agent. Methods: The black rice bran ethanolic extract was formulated into oil in water (o/w) lotion. In this study, 34 women applied the lotion at one side of the forearm and base placebo lotion as control at the other side of forearm. The results were tested with a paired t-test by GraphPad Prism 8.3.0 software. Results: There was a significant decrease in the melanin index and erythema index in the forearm with a lotion containing black rice bran extract (P-value < 0.0001). Conclusions: The lotion containing 10% black rice bran extract was effective as a skin lightener because it effectively reduced skin melanin production when applied topically.
... Since tyrosinase catalyzes the formation of melanin pigment, inhibition of this enzyme by hydroquinone and kojic acid is gaining importance in the cosmetic industry due to their anti-pigmenting effect (Momtaz et al., 2008). In addition to skin whitening agents, tyrosinase inhibitors are also used as food additives and alternative of insect control agents (Miyazawa et al., 2003). The CBEA showed maximum inhibition potential (96.02 §3.24 mgKAE/g) against tyrosinase, whereas, CBB and CBM exhibited mild inhibition (40.61 §4.56 and 39.44 §4.44 mgKAE/g) of tyrosinase. ...
Caragana is one of the most important genera of the plant family Fabaceae, and is famous for conventional folklore medicines applications. Therefore, the present investigation was designed to explore therapeutical potentials of various extracts of Caragana brachyantha Rech.f (Hexane, Ethyl acetate, n-Butanol, Methanol, aqueous) through in-vitro biological screening. The UHPLC-MS analysis of the extracts disclosed phytochemical composition and total bioactive contents. Ethyl acetate extract (CBEA) offered the highest phenolic (48.49±1.23 mgGAE/g extract) and flavonoid (16.48±0.26 mgRE/g extract) contents and also exhibited significant antioxidant activities. The observed antioxidant potential was further supported by Pearson correlation studies, which depicted a positive relationship between total phenolic contents (TPC) and total flavonoid contents (TFC). Methanolic extract (CBM) exhibited the highest anti-α-glucosidase activity (2.02±0.02 mmolACAE/g extract) while CBEA was found more active (96.02±3.24 mgKAE/g extract) in tyrosinase inhibition assay. This investigation suggests potential uses of Caragana brachyantha in nutraceutical and pharmaceutical products and thus offers a great industrial application.
... All of the tested extracts exhibited inhibitory effects against tyrosinase, however the most potent was the ethanolic extract. As the protocatechuic acid was the most prevalent in this extract, inhibitory effects may be attributed to this compound, as previous papers have also reported its inhibitory activity towards tyrosinase [59,60]. ...
Bioactive compounds from natural sources are of great importance because of their potential pharmacological activity and tremendous structural diversity. In this study, the chemical composition of different moss extracts of Hedwigia ciliata P. Beauv. have been examined, as well as their antioxidant, antineurodegenerative/anti-neuroinflammatory, antidiabetic, and antiproliferative potential. The extracts were prepared by Soxhlet extractor using solvents of different polarity. Chemical characterization of the extracts revealed the presence of phenolics and flavonoid compounds, together with triterpenoids as secondary metabolites of high biological activity. Significant antioxidant properties of all the extracts were exhibited using the β-carotene assay. The highest activities were found for water:ethanol extract (with the highest inhibition rate of 96%), but also significant inhibition was measured for ethanol and ethyl acetate extracts (80% and 70%, respectively). Confirmation of biocompatibility of investigated moss extracts has been performed using normal human fibroblast cell line, MRC-5. The H. ciliata extracts exhibited significant antiproliferative activity (~ 50%) against the MDA-MB-231 (human breast adenocarcinoma cell line), which has not previously been reported elsewhere. The Griess assay confirmed the potential anti-neuroinflammatory activity of the extracts, as significant effects in reducing NO production by LPS-stimulated BV2 (normal murine microglia cell line) was observed. This data is in line with noted antineurodegenerative potential measured by the inhibition of acetylcholinesterase (with the highest inhibition rate of 60% for ethyl acetate extract) and tyrosinase (with the highest inhibition rate of 70% for ethanol extract). Additionally, the H. ciliata extracts exhibited significant antidiabetic effect mediated by α-glucosidase inhibition (with the highest inhibition rate of 80% for ethyl acetate extract). The obtained data suggest the presence of immunomodulatory effects of the moss extracts in vitro, which allows the design of new experiments aimed at detecting and characterizing bioactive compounds of the extracts and additionally elucidate detailed mechanisms of their effects.
... The enzyme catalyzed two consecutive oxidation reactions: The first step, the hydroxylation of L-tyrosine to 3,4-dihydroxy-L-phenylalanine (L-DOPA), and the second step, the oxidation of the L-DOPA to dopaquinone. Dopaquinone is a highly reactive substance that can polymerize spontaneously to generate melanin [1][2][3]. Hence, tyrosinase inhibitors can be used as treatments for hyperpigmentation-related skin disorders and as skin-whitening agents. ...
Vitis amurensis roots have been reported to have the potential for skin whitening through the evaluation of melanogenesis and tyrosinase inhibitory activities. In this study, V. amurensis roots were utilized to quickly select whitening ingredients using LC-Q-TOF-MS coupled with tyrosinase inhibitory assay, and to optimize the extraction process for use as a skin whitening functional material by response surface methodology. Results showed that V. amurensis roots exhibited tyrosinase inhibitory effects by two stilbene oligomers, ε-viniferin (1) and vitisin B (2), as predicted by LC-Q-TOF-MS coupled with bioassay. The optimal extraction conditions (methanol concentration 66%, solvent volume 140 mL, and extraction time 100 min) for skin whitening ingredients were established with the yields 6.20%, and tyrosinase inhibitory activity was 87.27%. The relationship between each factor and its corresponding response was confirmed by Pearson’s correlation analysis. The solvent volume showed clear linear relationship with yields, and methanol concentration had a strong linear relationship with tyrosinase inhibitory activity for compounds 1 and 2, as well as their combination. Overall, LC-Q-TOF-MS coupled with bioassay was proved to have the potential to effectively find new active constituents, as well as known active constituents; vitisin B can be proposed as a new natural potential whitening agent.
... Moreover, sulforaphane increased the expression of ERK protein that further suppressed the melanogenesis [28]. Several studies reported the tyrosinase inhibition of phenolics such as ferulic acid and p-coumaric acid [23], but not for vanillic acid [29]. It should be noted that sulforaphane, ferulic acid was only found in DCM extract, while vanillic was only found in aqueous extract. ...
This study was aimed to determine antioxidant and tyrosinase inhibition effects of the pod of Raphanus sativus L. var. caudatus Alef extract. The compounds consisted in the extracts were identified by HPLC from standard peak comparison. Pod was extracted by using 2 different solvents-dichloromethane (DCM) and water. The antioxidant activity was evaluated based on free radical scavenging (DPPH) activity and ferric reducing ability (FRAP) assay. The lightening effect was determined from the inhibition of mushroom tyrosinase in vitro. The results showed that DCM extract contained sulforaphene, protocatechuic acid, p-hydroxybenzoic acid, caffeic acid, and ferulic acid. The aqueous extract contained sulforaphene, protocatechuic acid, p-hydroxybenzoic acid, caffeic acid, vanillic acid, and p-coumaric acid. The DPPH· scavenging effect expressed as the IC50 values for DCM and aqueous extracts were 883.38 ± 22.9 and 1,160.49 ± 22.30 µg/mL, respectively. The reducing power of aqueous extract (218.27 ± 0.010 µM FeSO4 equivalent) was greater than DCM extract (166.34 ± 0.018 µM FeSO4 equivalent) at the same concentration (2,000 µg/mL). However, both extracts showed lesser antioxidant activity than gallic acid, a positive control. DCM extract showed higher tyrosinase inhibitory effect than aqueous extract but lesser than kojic acid, a positive control. Both extracts at 2,000 µg/mL concentration exerted 42 and 19 % tyrosinase inhibition, respectively. In conclusion, the extraction solvent yielded different chemical constituents and thus the activities. The DCM extract exerted greater antioxidant activity and tyrosinase inhibition activity than the aqueous extract. The extract fractionation is required to get higher yields of bioactive compounds prior to further study and for cosmetics product development.
... On the other hand, our results showed that the highest tyrosinase inhibition potential was obtained from WR, followed by RR and BR; however, the inhibition potential of all rice extracts was lower than that of the standard inhibitor KA. In contrast with our results, Miyazawa et al. (2003) reported on a study of BR bran compounds 1 to 8, which showed high tyrosinase inhibitory activity. However, Soradech et al. (2016) showed that the different coloured rice extract cultivars also showed significant differences in tyrosinase inhibitory activity, with the highest and lowest potentials obtained for Rice Berry and Sri-Nin (both rice cultivars are the coloured rice), respectively. ...
Rice is produced for consumption and traditional medicine. Rice is also used as an ingredient in cosmetic products. In this study, the author investigated the biological activity and inhibition potential against α‐glucosidase, α‐amylase and tyrosinase activity of rice extract (black rice [BR], red rice [RR] and white rice [WR]), rice volatile compounds, rice extract combined with volatile compounds, rice extract combined with standard inhibitors and volatile compounds combined with standard inhibitors. The results revealed that the free‐radical scavenging capacity of rice extract is related to the phenolic content and flavonoids. BR showed the highest potential to inhibit α‐glucosidase and α‐amylase activity, whereas WR showed the highest potential to inhibit tyrosinase activity. Among rice volatile compounds, vanillin and vanillyl alcohol had the highest inhibition potential against α‐glucosidase and α‐amylase, respectively, whereas guaiacol had the highest inhibitory activity against tyrosinase. Molecular docking supported by the high binding efficiency was also obtained from vanillin and guaiacol when located at the active site of these enzymes. The combination of RR with acarbose (AB) had the highest inhibition potential and showed a synergic effect on both α‐glucosidase and α‐amylase. Interestingly, the combination of rice extract (BR, RR and WR) and vanillin and vanillyl alcohol had a synergic effect on α‐amylase. Moreover, the combination of WR and vanillyl alcohol had the highest inhibition potential and showed a synergic effect on tyrosinase, whereas rice volatile compounds had a synergic effect on tyrosinase obtained from 2‐pentylfuran/kojic acid (KA), vanillin/KA and vanillyl alcohol/KA.
... Moreover, rice bran which formulated in cosmetic products are found to be stable, free from heavy metals, and microbial contamination [8]. Miyazawa et al. reported that 0.4-mg/ml black rice bran extract inhibited tyrosinase activity by as much as 80.5% [9]. ...
Objective: The objectives of this study were to quantify γ-oryzanol in an ethanolic extract of Oryza sativa L. Indica (black rice) bran and to evaluate its activity as a tyrosinase inhibitor. Methods: Black rice bran was extracted via maceration in 96% ethanol, and the γ-oryzanol concentration in the extract was measured through high-performance liquid chromatography. The applicability of the extract as a skin lightening agent was determined by evaluating its tyrosinase inhibition activity. Results: The dry rice bran contained 118.572 mg/g of γ-oryzanol, and the extract inhibited tyrosinase activity at an IC50 of 74.8%. Conclusion: The black rice bran extract was sufficiently potent for use in skin lightening formulations.
... Rice and its products were investigated as outstanding sources for the treatment of skin diseases as well [24,25]. Among identified cosmeceutical compounds from rice, flavonoids [26], ferulic acid, γ-oryzanol, and phytic acid [27] were the most common. Also, previous studies signified the cosmeceutical property of the complex terpene-lactone compounds such as 2,3-epoxyjuanislamin [28], ginkgolide B [29], and α-cyclocostunolide [30] which potently inhibited the melanogenesis. ...
We previously reported the inhibitory potentials of momilactones A (MA) and B (MB) against key enzymes related to type 2 diabetes and obesity. In this study, antioxidant and anti-skin-aging activities of MA and MB were investigated and compared with tricin, a well-known antioxidant and antiaging flavonoid in rice. MA, MB, and tricin were purified from rice husk by column chromatography and their biological activities were subsequently assayed by in vitro trials. The contents of MA, MB, and tricin of different commercial rice cultivars in Japan were quantified and confirmed by ultra-performance liquid chromatography-electrospray ionization-mass spectrometry (UPLC-ESI-MS) and high-performance liquid chromatography (HPLC) analyses. The antioxidant assays revealed a synergistic activity of the mixture MA and MB (MAB, 1:1, v/v). In addition, in 2,2’-azino-bis (ABTS) assay, IC50 values of MAB (0.3 mg/mL) and tricin (0.3 mg/mL) was 4-fold and 9-fold greater than that of individual MB (1.3 mg/mL) or MA (2.8 mg/mL), respectively. The in vitro enzymatic assays on pancreatic elastase and tyrosinase indicated that MA and MB were potential to relief skin wrinkles and freckles. In detail, MA exerted higher inhibition on both enzymatic activities (30.9 and 37.6% for elastase and tyrosinase inhibition, respectively) than MB (18.5 and 12.6%) and MAB (32.0 and 19.7%) at a concentration of 2.0 mg/mL. Notably, MA and the mixture MAB exhibited stronger inhibitions on elastase and tyrosinase in comparison with tricin and vanillin. MA, MB, and tricin in rice are potential to develop cosmetics as well as supplements for skin aging treatments.
... In 2003 Mitsuo Miyazawa investigated the inhibitor of tyrosinase activity in black rice bran. Their data implied that the depigmenting effect of black rice bran components likely involves an inhibition of tyrosinase activity (Miyazawa et al., 2003). In 2009 Venkateswara isolated 5 secondary metabolites from Chloroxylon swieteniaDC, namely 6, 8-diprenylumbelliferone, bergaptan, isopimpinellin, tritriacontanol, and isoquercetrin, and investigated them for their tyrosinase inhibition activity (Venkateswara et al., 2009). ...
... Protocatechuic acid from black rice bran extract also exhibited on inhibitory effect on enzymatic browning. (40) Macrae and Duggleby (41) reported that the p-coumaric, ferulic and cinnamic acids exhibited the most potent inhibitory effect against potato PPO. These acids from full-fatted, commercially defatted rice bran extracts exhibited inhibitory effects against enzymatic browning on potato and apple PPO (10). ...
Enzymatic browning is a serious quality deterioration of fresh-cut fruits and vegetables. Recently, consumers and fruit and vegetable industrial processors have demanded the use of natural antibrowning agents to replace the use of chemicals. Mango (Mangifera indica cv. Chok Anan) peel was prepared in the form of mango peel liquid nitrogen powder. This included extraction by ultrasound or ultrasound combined with stirring. The total phenolic content of mango peel liquid nitrogen powder extract (further in the text: mango peel extract) was the highest after the extraction for 15 min using ultrasound followed by stirring for 15 min. The browning value of potato puree treated with mango peel extract was lower, while its L* value and the hue angle were larger than of samples treated with ascorbic or citric acids during storage for 6 h. Mango peel extract had a competitive inhibitory effect on potato polyphenol oxidase (PPO), which was larger than either ascorbic or citric acid. Its IC50 value was 0.3 mg/mL. Mangiferin, protocatechuic and gallic acid found in mango peel extract had high inhibitory effect on potato PPO, making mango peel a potential natural source of enzymatic browning inhibitor.
... Results presented in Table 5 showed the inhibitory action of the different extracts of B. abyssinica and S. dulcis on tyrosinase. Tyrosinase inhibition is considered as an ideal target in the management of epidermal hyperpigmentation conditions linked to melanin overproduction (Zengin et al. 2018a (Miyazawa et al. 2003;Sharifi Far et al. 2013;Nakamura et al. 2017). Benzenetriol derivative, identified in B. abyssinica (Zekeya et al. 2014), demonstrated tyrosinase inhibition (Choi et al. 2010). ...
In the present study, two medicinal plants from Africa, namely Bersama abyssinica Fresen. and Scoparia dulcis L., were extracted using ethyl acetate, methanol, and water. The antioxidant, enzyme (α-amylase, α-glucosidase, acetyl- and butyrylcholinesterase, lipase, and tyrosinase) inhibitory action, and phytochemical profiles of extracts of Bersama abyssinica and Scoparia dulcis were determined. The aqueous (180.62 and 61.81 mg gallic acid equivalent/g extract, for B. abyssinica and S. dulcis respectively) and methanol (75.21 and 57.81 mg rutin equivalent/g extract, for B. abyssinica and S. dulcis, respectively) extracts contained high concentrations of phenolic and flavonoids, respectively. The ethyl acetate extracts of both plants were potent inhibitors of α-glucosidase and tyrosinase. Several phytochemical groups were determined by HPLC-MS/MS. The study tend to suggest that B. abyssinica and S. dulcis are potential candidates for the development of novel therapeutical agents.
... The inhibition of tyrosinase activity of the fermented brewer's rice extract may be attributed to the presence of kojic acid in the extract. Kojic acid has been tested, reported and used extensively in cosmetic preparations as prevention of melanin overproduction in epidermal layers of the skin (Miyazawa et al., 2003). On the other hand, elastase inhibition activity of fermented brewer's rice extract may be contributed by ferulic and caffeic acids detected in the extract. ...
Aims: Brewer's rice is one of the by-products from rice processing industry that is rich in bioactive compounds but currently underutilized. Exploitation of agro-industrial by-products as substrates in solid-state fermentation processes provides value-addition to these underutilized by-products. The purpose of this research is to evaluate the potentiality of brewer's rice as a source of cosmeceutical or cosmetic bio-ingredient by utilizing solid-state fermentation process.
Methodology and results: Brewer's rice was submitted to solid-state fermentation with Aspergillus oryzae from MARDI's Collection of Functional Food Culture (CFFC). Extracts of unfermented and fermented brewer's rice were later subjected to determination of biological content and biological activities, as well as measurement of their phenolic and organic acids content. The extract of fermented brewer's rice exhibited an increase in total phenolic and total flavonoid content and showed enhanced 2, 2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging and ferric-reducing activities. Additionally, it was also found that the tyrosinase and elastase inhibition activities of fermented brewer's rice extract is significantly higher with nearly 7-and 57-fold, respectively, than the unfermented extract. Ferulic and kojic acid-two of the most important compounds in cosmeceutical formulations, were also detected in fermented brewer's rice extract.
Conclusion, significance and impact of study: Antioxidant, anti-pigmentation and anti-wrinkle properties of brewer's rice were successfully enhanced by fermentation with A. oryzae. Fermented brewer's rice extract has high potential to be developed as functional bio-ingredient for cosmeceutical as well as nutraceutical products.
... Can Tyrosinase inhibitor activity of sample be seen from IC50 values greater than kojic acid (16.68 µg / mL) as standard. When referring to the classification of activities according to [18,19] leaves and fruits belimbing wuluh extracts were classified as inactive because the IC50 value was <1000 ppm. ...
Hyperpigmentation is an event that occurs due to excessive production of skin pigments, where the presence of melanin. Belimbing wuluh as Indonesian plant is rich compounds that function as antioxidants and tyrosinase inhibitor. The aim this research to test the potency of belimbing wuluh extracts as antioxidant and tyrosinase inhibitors for active ingredients whitening for skin. The method used in the study is experimental laboratory with some testing among others test for antioxidant activity with DPPH. Rutin as a standard for antioxidant activity. Tyrosinase inhibitor activity using tyrosinase from mushroom as enzym and L-tyrosine as a substrate with kojic acid as a standard. The IC50 value of antioxidant activity of belimbing wuluh fruits extract is 2331.69±339.09 g/ml and 320.76±79.54 g/ml from leaves extract. The IC50 value of antioxidant activity greater than rutin 5.92 g/ml. Tyrosinase inhibitor activity can be seen from IC50 values is 186.85±9.37 g/ml from fruits extract and 150.57±6.25 g/ml from leaves extract. The IC50 value of tyrosinase inhibitor greater than kojic acid 16.68 g/ml. Our findings showed that belimbing wuluh leaves extract better than fruits extract. These results suggest that belimbing wuluh is a natural ingredient that has potential to be used in halal skin whitening product.
... [14][15][16][17][18] It has been reported that veratric acid and its methyl ester do not show significant inhibitory effect on tyrosinase. 19 Hydrazides, acylated derivatives of hydrazine, are a class of organic compounds containing azomethine group (eN]CH) linked to an amide group. Hydrazide derivatives are pharmaceutically important, as they have been reported to possess a number of biological effects such as anti-inflammatory, antitumoral, antitubercular, anticonvulsant, antioxidant, analgesic, antiplatelet, antimalarial, antimicrobial, antimycobacterial, vasodilator, antiviral and antiulcer activities. ...
... Then, the structure of 2 was deduced by 2D NMR [HSQC and HMBC spectra ( Figure 2)] as shown in Figure 1. Other known compounds were identified as 3-O-trans-caffeoylbetulinic acid (1) (Pan et al. 1994), betulinic acid methyl ester (3) (Choi et al. 2008), betulinic acid (4) (Bisoli et al. 2008), lupeol (5) (Jain and Bari 2010), 4-hydroxybenzoic acid (6) (Liu et al. 2012), 3,4-dihydroxybenzoic acid methyl ester (7) (Miyazawa et al. 2003), 4-hydroxy-3, 5-dimethoxybenzoic acid (8) (Liu et al. 2012), 5,8-dihydroxy-7,4 0 -dimethoxyflavone (9) (Teles et al. 2015), isoscutellarein 4'-methyl ether 8-O-b-D-glucopyranoside (10) (Sharaf et al. 1998), methyl caffeate (11) (Roosevelt et al. 2011) and stigmasterol (12) (Jain and Bari 2010). ...
Phytochemical study on the extract of Vietnamese medicinal plant Helicteres hirsuta Lour. has led to the isolation and structural elucidation of twelve secondary metabolites, 3-O-trans-caffeoylbetulinic acid (1), 3β-benzoylbetulinic acid (2), betulinic acid methyl ester (3), betulinic acid (4), lupeol (5), 4-hydroxybenzoic acid (6), 3,4-dihydroxybenzoic acid methyl ester (7), 4-hydroxy-3,5-dimethoxybenzoic acid (8), 5,8-dihydroxy-7,4'-dimethoxyflavone (9), isoscutellarein 4'-methyl ether 8-O-β-D-glucopyranoside (10), methyl caffeate (11) and stigmasterol (12). Especially, compound 2 was reported as a new natural product. Their structures were elucidated by a combination of 2D NMR and ESI-FT-ICR-MS spectroscopies. Furthermore, eight compounds were tested for their cytotoxicity against five cancer cell lines (Hela, HepG2, SK-LU-1, AGS and SK-MEL-2). The results showed that compounds (1, 3-5, 9) have moderate activities. This is the first study on the chemical constituents and their cytotoxicity of the Vietnamese Helicteres hirsuta L.
... Furthermore, black rice anthocyanin extracts have been studied in various types of cancer, and have been shown to suppress cancer cell invasion (17), metastasis (18), and angiogenesis (19,20). Additionally, black rice bran inhibits tyrosinase activity in cell-free in vitro systems, suggesting its potential as a melanogenesis inhibitor (21). Germinated black rice also enhances hyaluronan production in HacaT keratinocytes (22). ...
Exposure of the skin to ultraviolet (UV) radiation causes extracellular matrix (ECM) collapse in the dermis, owing to an increase in matrix metalloproteinase (MMP) production in both the epidermis and dermis, and a decrease in type I collagen expression in the dermis. Recently, black rice (Oryza sativa L.) was reported to have a wide range of pharmacological effects in various settings. However, the effects of black rice extract (BRE) on UV‑irradiated skin cells have not yet been characterized. BRE treatment did not affect cell morphology and viability of HaCaT and human dermal fibroblasts (HDF). We demonstrated that BRE downregulated basal and UV‑induced MMP‑1 expression in HaCaT cells. Furthermore, BRE significantly increased type I procollagen expression, and decreased MMP‑1 and MMP‑3 expression in UV‑irradiated HDF. The underlying mechanisms of these results involve a decrease in p38 and c‑Jun N‑terminal kinase activity, and suppression of UV‑induced activation of activator protein‑1 (AP‑1). BRE reduced UV‑induced reactive oxygen species production in HaCaT cells in a dose‑dependent manner. Indeed, mass spectrometry revealed that BRE contained antioxidative flavonoid components such as cyanidin‑3‑O‑β‑D‑glycoside and taxifolin‑7‑O‑glucoside. These findings suggest that BRE attenuates UV‑induced ECM damage by modulating mitogen‑activated protein kinase and AP‑1 signaling, and could be used as an active ingredient for preventing photoaging of the skin.
... However, the accumulation of high levels of melanin in the skin, also known as hyperpigmentation, leads to the development of various dermatological problems (melasma, freckles, and age spots) (Karioti et al., 2007). Tyrosinase inhibitors are the most effective therapeutic agents for eliminating the quality losses associated with browning in foods and the disorders that occur as a result of hyperpigmentation in human skin (Miyazawa et al., 2003). As well known, men and women prefer to have a lighter skin colour. ...
Onosma species have traditionally been used as laxative and anthelmintic agents as well as their uses in eye, blood diseases, bronchitis, abdominal pain, strangury, thirst, itch, leucoderma, fever, wounds, burns, piles, and urinary calculi. This study examines the investigation of biological activities of ethyl acetate, methanolic, and aqueous extracts from Onosma gigantea Lam. The extracts were evaluated for the antioxidant and enzyme inhibitory activities. Phenolic compounds in the extracts were also detected by RP-HPLC-DAD. The aqueous extract showed remarkable antioxidant activity in phosphomolybdenum [134.31 μmol trolox equivalents (TEs)/g air dry matter (adm)], chelating effect [32.97 μmol ethylenediaminetetraacetic acid (disodium salt) equivalents (EDTAEs)/g adm], radical scavenging [on DPPH (32.14 μmol TEs/g adm) and ABTS (58.68 μmol TEs/g adm)], and reducing power [CUPRAC (50.23 μmol TEs/g adm) and FRAP (40.96 μmol TEs/g adm)] assays. The aqueous extract also exhibited considerable inhibitory activity of tyrosinase (10.48 μmol kojic acid equivalents/g adm) and α-glucosidase [1320.53 μmol acarbose equivalents (ACEs)/g adm]. It has been determined that the methanolic extract showed significant AChE (31.57 μmol galanthamine equivalents (GALAEs)/g adm) and α-amylase (6.75 μmol ACEs/g adm) inhibitory activity. The ethyl acetate, which contains low polarity compounds, showed the highest BChE inhibitory activity (6.87 μmol GALAEs/g adm). In general, it is found that there is a positive correlation between the phytochemical contents of the extracts and their biological activities. The results indicate that O. gigantea extracts could be considered as a novel source of bioactive agents with functional connections.
... Rice bran oil (RBO) is rich in unsaturated fatty acids (oleic, linoleic, and α-linolenic acids) and saturated fatty acids (palmitic and stearic acids). RBOs are used in the cosmetic products, mainly in sunscreen, antiaging, and skin-lightening products, because of its bioactivities and moisturizing properties on the skin [11][12][13][14][15]. Thai-pigmented rice has been reported as an active ingredient in cosmetics, pharmaceuticals, and functional foods [16]. ...
Objective: The rice bran (RB) phytochemicals are known for several pharmacological properties. The current study aimed to extract the active principles from Thai purple rice bran, formulate the cosmetic products, evaluate the physical property, and stability of the products.Methods: The RB was prepared by 80% ethanolic extraction, and measured the total phenolic and anthocyanin content by HPLC, and spectrophotometric methods. The antioxidant capacity of RB oil (RBO), RB extract (RBE) was assessed by spectrophotometric methods. The cosmetic products were formulated with rice bran extract and fermented and distilled purple rice solution (FDPRS). The stability of the formulations was assessed. The heavy metal and microbial contamination were determined by atomic absorption spectrometry, and plating assay, respectively.Results: The yield of PRE and RBO was 0.92, and 1.62%, respectively. The total phenolic and anthocyanin content of PRE was 305.30 ± 6.15 mg gallic acid/g of extract, and 877.33 ± 87.73 mg cyanidin chloride /g of extract, respectively. RBO, PRE, and FDPRS exhibited high antioxidant capacity. The cosmetic formulations were physically stable in the heat-cool cycle, and the stability of active compounds was not affected while stored at 30°C for two months. The storage temperature affected the phenolic compounds present in the cosmetic formulations, especially at 45°C. There was no significant decrease in oryzanol content of soap formulation. All the formulations were free microbial and heavy metal contamination.Conclusion: The rice bran phytochemical based cosmetic products are rich in antioxidants, stable, free from heavy metals and microbial contaminations, and further fine tuning of the formulation may achieve the market quality.
BACKGROUND
Velvetleaf (Abutilon theophrasti Medik.), primarily a cropland weed, exerts adverse impacts on the productivity of various crops, including soybean (Glycine max L.), wheat (Triticum aestivum L.), and maize (Zea mays L.), by hindering their vegetative growth. However, the interference mechanism of velvetleaf on the three crops remains unclear.
RESULTS
The inhibitory effect of velvetleaf water extract on the germination and growth of soybean, wheat, and maize was determined in pot experiments and field trials. Four phenolic acids were identified as allelochemicals: protocatechuic acid (PA), gallic acid (GA), chlorogenic acid (CHA), and vanillic acid (VA). These allelochemicals were detected in different parts (leaves, roots, and stems) of velvetleaf, and in the rhizosphere soil of tested crops over the range of 1.19–556.23 μm kg⁻¹. These allelochemicals were administered in approximate concentrations as in velvetleaf roots and rhizosphere soil, and their effects varied with crop species and velvetleaf parts. The allelochemicals generally had low‐dose stimulation and high‐dose inhibition effects on the growth of soybean, wheat, and maize. Furthermore, the biomass distribution of these crops was affected by allelochemicals in the soil. In field trials, the allelochemicals significantly (P < 0.05) inhibited the growth of all tested crops over the whole growth period, and PA showed a significant (P < 0.05) inhibitory effect on the yield of soybean, wheat, and maize.
CONCLUSION
GA, PA, CHA, and VA in velvetleaf aqueous extracts were identified as allelochemicals that play an inhibitory role on three crops. © 2022 Society of Chemical Industry.
This research was conducted to evaluate the bioactive compounds content and biological activity of legume extract (mung bean (MB), job’s tears (JT), red kidney bean (RB) and black bean (BB)), sesame extract (white sesame (WS) and black sesame (BS)) and lemon basil seed extract (LB). The research also investigated the combined LB extract with kojic acid, acarbose and five rice volatile compounds against α-glucosidase, α-amylase and tyrosinase activity. The inhibitory activity of three enzymes and the extracts’ antioxidant capacity was closely related to the total phenolic and total flavonoid content. LB methanol extract (LB(ME)) had the highest total phenolic content, total flavonoid content and antioxidant capacity. LB water extract (LB(WE)) with the IC50 of 0.04 ± 0.004 and 0.14 ± 0.01 mg/mL had the highest inhibition potent against α-glucosidase and tyrosinase enzymes. In comparison, LB(ME) with the IC50 of 0.13 ± 0.01 mg/mL represented the highest inhibition potent on the α-amylase enzyme. Five rice volatile compounds with the α-glucosidase, α-amylase and tyrosinase inhibitory activity, low cytotoxicity and high anti-nitric oxide production were combined with LB extract to investigate the enzymatic inhibitory effect. The results indicated that LB(WE)/2-methoxy-4-vinylphenol and LB(WE)/2-pentyl furan had a synergic effect on α-glucosidase activity. We also investigated LB extract combined with acarbose and kojic acid against these enzymes. The results showed that LB(ME)/acarbose had the highest inhibition potent on α-glucosidase and α-amylase activity and LB(WE)/kojic acid had the highest on tyrosinase activity. Thus, these results suggest that using LB extract and the combined may be a useful therapeutic approach for diabetes and melanogenesis treatment.
To clarify preservation mechanism and flavor variation of postharvest button mushroom (Agaricus Bisporus) coated compounds of protocatechuic acid-CaCl2-NaCl-pullulan, the protocatechuic acid (118 mg/L)-CaCl2 (0.83%)-NaCl (0.55%)-pullulan (0.30%) composite preservative (CP) at the spray rate of 13:1 was used to coating on button mushroom and storage at 4 ± 1 °C. Compared to the negative control (NC) group, the respiration rate, browning degree, malondialdehyde (MDA) content, polyphenol oxidase (PPO), and total phenolic content of CP treatment decreased 26%, 27%, 25%, 26% and 37% respectively after 12days. On the contrary, the peroxidase (POD), catalase (CAT), phenylalanine ammonia-lyase (PAL) and total superoxide dismutase (T-SOD) of CP treatment increased 57%, 40%, 39% and 30% respectively. Further, button mushroom coated with CP maintained a higher content of soluble protein and nucleic acid, but lower content of free amino acid (FAA) than NC group. Characteristic flavor substance of button mushroom coated by CP, 3-octanone was higher than that in the NC group, but lower alkanes. Moreover, there was no significant difference in 3-octanone between the CP and fresh button mushroom. Hence, the CP treatment had improved postharvest button mushroom texture and flavors, and storage at 4 ± 1 °C, its shelf life is prolonged to 12 days after coated compounds of protocatechuic acid (118 mg/L)-CaCl2 (0.83%)-NaCl (0.55%)-pullulan (0.30%).
Background
Melanin plays an important role in protecting human skin, while excessive synthesis of melanin can cause abnormal pigmentation and induce skin diseases. Long-term use of commercial whitening agents in managing skin melanin such as kojic acid and arbutin can lead to some negative effects such as dermatitis and liver cancer. Although past studies have researched the melanin inhibitory effect of plant extracts, the effective dose and mechanisms are not well summarized and discussed. This study aims to explore the melanin inhibitory property of phytochemicals and tries to answer the following research questions: 1) Which plant extracts and phytochemicals could inhibit melanin biosynthesis in the skin? what is the mechanism of action? 2) Have human trials been conducted to confirm their melanin inhibitory effect? 3) If not, which phytochemicals are recommended for further human trials? This article would provide information for future research to develop natural and safe skin whitening products.
Methods
A preferred reporting items for systematic reviews and meta-analyses (PRISMA) systematic review method and OHAT risk-of-bias tool were applied to screen literature from 2000-2021 and 50 research articles met the selection criteria.
Results
Flavonoids, phenolic acids, stilbenes and terpenes are main classes of phytochemicals responsible for the melanin inhibitory effects. The in vitro/in vivo melanin inhibitory effects of these plant extracts/phytochemicals are achieved via three main mechanisms: 1) the ethyl acetate extract of Oryza sativa Indica cv., and phytochemicals such as galangin and origanoside could manage melanin biosynthesis through competitive inhibition, non-competitive inhibition or mixed-type inhibition of tyrosinase; 2) phytochemicals such as ginsenoside F1, ginsenoside Rb1 and 4-hydroxy-3-methoxycinnamaldehyde could inhibit melanogenesis through down-regulating microphthalmia-related transcription factor (MITF) gene expression via different signaling pathways; 3) the ethanolic extracts of Dimorphandra gardneriana, Dimorphandra gardneriana, Lippia microphylla and Schinus terebinthifolius have a good ultraviolet absorption ability and high sun protective factor (SPF) values, thereby inhibiting UV induced melanogenesis in the skin.
Conclusion
Although many plant extracts and phytochemicals have been found to inhibit melanin production, most of the results were only proved in cellular and/or animal models. Only the ethyl acetate extract of Oryza sativa Indica cv. panicle, and ginsenoside F1 were proved effective in human trials. Animal studies proved the effectiveness of galangin, origanoside, ginsenoside Rb1 and 4-hydroxy-3-methoxycinnamaldehyde with effective dose below 3 mM, and therefore recommended for future human trial. In addition, cellular studies have demonstrated the effectiveness of oxyresveratrol, mulberroside A, kurarinol, kuraridinol, plumbagin, (6aR,11aR)-3,8-dihydroxy-9-methoxy pterocarpan, ginsenoside Rh4, cardamonin, nobiletin, curcumin, β-mangostin and emodin in inhibiting melanin synthesis at low concentrations of 20 µM and proved the low SPF values of Dimorphandra gardneriana, Dimorphandra gardneriana, Lippia microphylla and Schinus terebinthifolius extracts, and therefore recommended for further animal and human trials.
Background
Cymbopogon khasianus is a widely used industrial and pharmacologically important aromatic grass species.
Objective
The present investigation was designed to study and compare the elemicin rich Cymbopogon khasianus essential oil (EREO) and its pharmacological effects, genotoxicity with pure compound elemicin
Materials and Methods
Chemical composition, identification was performed using GC/MS and NMR techniques. 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH), reducing power assay for antioxidant; albumin denaturation, protease inhibitor for anti-inflammatory; acetylcholinesterase (AChE) for anti-cholinesterase; amylase inhibitory for anti-diabetic; tyrosine inhibitory for skin whitening; disc diffusion and minimum inhibitory concentration assay for antimicrobial, and Allium cepa assay for genotoxicity were used.
Results
GC/MS analysis identified 38 compounds; among them elemicin 72.34%, D-limonene 3.81%; methyl eugenol 3.34% were the major compounds. A significant amount of antioxidant activity IC50 31.38 µg/mL; anti-inflammatory activity (protein denaturation assay) IC50 16.77 µg/mL; protease inihibitor assay IC50 51.08 µg/mL; anticholinesterase IC50 12.095 µg/mL; antidiabetic activity IC50 17.36 µg/mL; and anti-tyrosinase activity IC50 17.69 µg/mL were reported. Antimicrobial activity analysis against 13 microbial strains revealed negative effect. Genotoxicity study using Allium cepa assay revealed negative toxicity of EREO with aberration percentage of 04.30% and pure elemicin 05.30% which was very low in comparison to ethyl-methanesulfonate (EMS) 13.90%.
Conclusion
To the best of our knowledge this is the first scientific evaluation of novel elemicin rich EREO pharmacological properties and to compare with pure compound elemicin. Together, it can be stated that EREO possesses antioxidant, anti-inflammatory, anti-cholinesterase activities way better than pure compound elemicin as well as standard drugs used.
Developing rice varieties with enhanced levels of functional bioactives is an important intervention for achieving food and nutritional security in Asia where rice is the staple food and Type II diabetes incidences are higher. The present study was aimed at dissecting out the molecular events underlying the accumulation of bio active compounds in pigmented traditional rice Kavuni. Comparative transcriptome profiling in the developing grains of Kavuni and a white rice variety ASD 16 generated 37.7 and 29.8 million reads respectively. Statistical analysis identified a total of 9177 exhibiting significant differential expression (DEGs) between the grains of Kavuni and ASD 16. Pathway mapping of DEGs revealed the preferential up-regulation of genes involved in the biosynthesis of amylose and dietary fibres in Kavuni accounting for its low glycemic index (GI). Transcripts involved in the biosynthesis of carotenoids, flavonoids, anthocyanins, phenolic acids and phenylpropanoids were also found to be up-regulated in the grains of Kavuni. This study identified up-regulation of key transcripts involved in the accumulation of phenolic acids having potential for inhibiting major hydrolytic enzymes α-amylase and α-glucosidase and thus accounting for the slow digestibility leading to low GI. Overall, this study has identified molecular targets for the genetic manipulation of anti-diabetic and anti-oxidant traits in rice.
Bamboo is a widely distributed graminaceous plant in China and is a potential source of bioactive substances. Incidentally, bamboo's fruit is rich in phytochemicals such as polyphenols and flavonoids, which are significant to human health. In this study, we identified the phenolic compounds of the fruit and investigated the antioxidant activities of Cephalostachyum fuchsianum Gamble (CFG) fruit polyphenols with in vitro and in vivo tests for the first time. UPLC-Q-TOF-MS/MS analysis results showed that the fruit contained 43 phenolic compounds, including 7 hydroxybenzoic acids, 12 flavonoids, 7 coumarins, 10 hydroxycinnamic acids, 1 terpenoid, and 5 lignans. The TPC of SP extracts was higher than that of IBPs extracts in FP and FF. The SP extracts in FP showed better antioxidant activities in vitro compared to those in FF. In addition, polyphenols from CFG fruits protected against H2O2-induced oxidative damage in HepG2 cells, and the protective effect of polyphenols in FP was superior to that in FF. The analysis results showed that CFG fruit has great potential in exploiting natural chemical substances, which can provide valuable pieces of information for the further development and utilization of CFG.
Portulaca oleracea is a well-known species for traditional medicine and food homology in Taiwan. In traditional medicine, P. oleracea is also used to treat gastrointestinal disorders, liver inflammation, fever, severe inflammation, and headaches. We investigated antioxidant, anti-tyrosinase, and anti-α-glucosidase activities of various solvent extracts and major bioactive components from P. oleracea. Ethanol and acetone extracts showed potent DPPH, ABTS, and hydroxyl radical scavenging activities. Chloroform and n-hexane extracts displayed significant superoxide radical scavenging activity. Furthermore, ethyl acetate and acetone extracts of P. oleracea showed potent anti-tyrosinase and anti-α-glucosidase activities. Examined and compared to the various solvent extracts for their chemical compositions using HPLC analysis, we isolated seven major compounds and analyzed their antioxidant, anti-tyrosinase, and anti-α-glucosidase activities. Seven active compounds of P. oleracea, especially quercetin, rosmarinic acid, and kaempferol, exhibited obvious antioxidant, anti-tyrosinase, and anti-α-glucosidase activities. The molecular docking model and the hydrophilic interactive mode of tyrosinase and α-glucosidase revealed that active compounds might have a higher antagonistic effect than commonly inhibitors. Our result shows that the active solvent extracts and their components of P. oleracea have the potential as natural antioxidants, tyrosinase and α-glucosidase inhibitors. Our results suggest that the active solvent extracts of P. oleracea and their components have potential as natural antioxidants, tyrosinase and α-glucosidase inhibitors.
Rice is a source of bioactive compounds related to human health and has been used for both consumption and traditional medicine. The authors investigated the synergistic and additive effect of rice extract (RE) combined with five aromatic compounds against three enzymes: α-glucosidase, α-amylase and tyrosinase. RE was purified by thin-layer chromatography (TLC) and preparative TLC (PTLC) with different solvent systems. RE had higher α-glucosidase and α-amylase inhibitory activity than the five aromatic compounds, while the five aromatic compounds had higher tyrosinase inhibitory activity than RE. The combination of RE/acarbose produced synergic inhibition of α-glucosidase and α-amylase, whereas RE showed additive inhibition of both enzymes when combined with aromatic compounds. The five aromatic compounds showed additive inhibition of tyrosinase when combined with RE. The combination of 2-methoxy-4-vinylphenol/vanillin/guaiacol produced synergistic inhibition of α-amylase while showing antagonism of α-glucosidase and tyrosinase. Interestingly, the RE produced additive inhibition of α-glucosidase, α-amylase and tyrosinase when combined with the 2-methoxy-4-vinylphenol/vanillin/guaiacol combination. RE had rich bioactive compounds related to α-glucosidase, α-amylase and tyrosinase inhibitory activity. Volatile compounds, including 2-methoxy-4-vinylphenol, vanillin and guaiacol, enhanced the inhibitory activity of RE against α-glucosidase, α-amylase and tyrosinase activities.
Antioxidant plays an important role in reducing the risk of chronic diseases. By using DPPH radical scavenging assay-guided fractionation, a bioactive compound has been isolated from the methanol extract of the leaves of Myristica fatua Houtt and subsequently identified as methyl 3,4-dihydroxybenzoic (MDB). The structure of MDB was confirmed by UV, FT-IR, MS, 1- and 2-D NMR spectroscopy. This compound exhibit antioxidant activity together with previous compounds i.e (7S,8R,8′S,7′S)-7,7′-bis(3-hydroxy-5-methoxyphenyl)-8,8′-dimethylbuthane-7,7′-diol and 3”-hydroxy demethyldactyloidin with IC 50 values 7.96, 101.1 and 15.4 μg/mL, respectively. These findings demonstrate that MDB can be considered as a natural antioxidant.
Objective
To evaluate the anti‐aging activity of cream containing the methanolic purple glutinous rice extract loaded in niosomes.
Methods
The in vitro biological activities of the purple glutinous rice extracted by methanol maceration were determined. The extract loaded in niosomes and the cream containing the niosomes were developed. The in vivo anti‐aging activity in 20 human volunteers including skin hydration, pigmentation, roughness and elasticity after daily application for 28 days compared to at initial was evaluated by Corneometer, Mexameter, Visiometer and Cutometer, respectively.
Results
The purple glutinous rice extract showed free radical scavenging (SC50), lipid peroxidation inhibition (IPC50), metal ion chelating (CC50) and tyrosinase inhibition (IC50) values at 32.31±1.28, 57.40±2.12, 85.05±5.43 and 43.89±2.14 mg/ml which were 0.00031, 0.011, 0.0078 and 0.0016 times of the standards (0.01±0.00, 0.62±0.14, 0.66±0.05 and 0.07±0.01), respectively. The purple glutinous rice extract contained 0.35 µg of anthocyanin/ 1 mg of the extract determined by HPLC. After loaded in niosomes, the solubility of the extract was not only increased in various solvents, but also the chemical stability in different environments (weak base, reducing agent and acid salt) was improved. The cream formulation containing niosomes loaded with 1%w/v of the purple glutinous rice extract indicated the anthocyanin remaining percentages after 6 cycles of heating and cooling test at 52.28% of the initial. For in vivo anti‐aging activities, cream containing niosomes loaded with the extract gave significant decreased melanin index and skin roughness reduction of ‐14.05 and ‐9.95% of the initial, respectively. The % changes of the increased skin hydration, skin elastic extension and skin elastic recovery when applied on human volunteers’ skin with this formulation were +48.73, ‐24.51 and +35.98%, respectively.
Conclusion
The cream containing niosomes loaded with the 1%w/v methanolic purple glutinous rice extract gave not only the suitable in vitro antioxidant activity and physical stability of the active anthocyanin, but also the superior in vivo anti‐aging activity on human skin compared to the cream base and before application which can be further developed as a novel anti‐aging cosmeceutical product.
Background: Tyrosinase is a multifunctional, glycosylated and copper containing oxidase, and is found in fungi, microorganisms, plants and animals. The most important function of tyrosinase in mammals is melanogenesis. Hyperpigmentation is a serious problem for beauty. It is possible to cure these diseases with inhibition of tyrosinase. There have been attempts to control the metabolism of pigmentations by means of natural chemical agents.
Objective: The aim of this study was to find new potent inhibitors for ،tyrosinase among plant extracts.
Method: The subject of this study was anti-tyrosinase activity of methanolic extracts of 70 plant species, using mushroom tyrosinase inhibition method. All extracts were screened for their tyrosinase inhibitory activity at 400, 100, 25, 6.2 µg/ml final concentrations in reaction mixture. Assay method was based on spectrophotometric study of absorption in 492 nm and kojic acid was used as positive controls.
Results: The results showed that nine plant extracts including Bongardia chrysogonum (L.) Spach, Podophylaceae, Heptaptera anatolica (Boiss.) Tutin, Apiaceae, Hyoscyamus kurdicus Bornm, Solanaceaes, Hypericum scabrum, Marrubium cuneatum, Nonea hypoleia, Salvia suffruticosa, Scrophularia pruinosa Boiss, Scrophulariaceae and Verbascum phoenicum L, Scrophulariaceae, (400 µg/ml) and two plant extracts including Asperugo procumbens L, Boraginaceae and Astragalus siliquosus Boiss. subsp. siliquosus, Papilionaceae (25µg/ml) have inhibitory activity more than 60%. Saliva suffruticosa showed a considerable inhibition value, 92.62% (400 µg/ml) and low IC50 (94.77 µg/ml) and according to kinetic analysis its type of inhibition on tyrosinase is noncompetitive.
Conclusion: Because of its high inhibitory activity and low IC50, Saliva suffruticosa extract would be interesting for further studies.
Investigation of components of the chloroform-soluble and ethyl acetate-soluble extracts of the aerial parts of Chromolaena odorata L. selected by PCSK9 mRNA expression monitoring assay in HepG2 cells led to the isolation of a new stilbene dimer, (+)-8b-epi-ampelopsin A (1), and 30 known compounds (2–31). The structures of the isolates were established by interpretation of NMR spectroscopic data and the stereochemistry of the new stilbene (1) was proposed based on ECD and NMR calculations. Among the isolates, 1, 5,6,7,4′-tetramethoxyflavanone (6), 5,6,7,3′,4′-pentamethoxyflavanone (7), acacetin (18), and uridine (21) were found to inhibit PCSK9 mRNA expression with IC50 values of 20.6, 21.4, 31.7, 15.0, and 13.7 µM, respectively. Furthermore, the most abundant isolate among the selected compounds, 6, suppressed PCSK9 and low-density lipoprotein receptor protein expression in addition to downregulating the mRNA expression of HNF-1α.
Background
Pigment melanin has primarily a photo defensive role in human skin, its unnecessary production and irregular distribution can cause uneven skin tone ultimately results in hyper pigmentation. Melanin biosynthesis is initiated by tyrosine oxidation through tyrosinase, the key enzyme for melanogenesis. Not only in humans, tyrosinase is also widely distributed in plants and liable for browning of vegetables and fruits. Search for the inhibitors of tyrosinase have been an important target to facilitate development of therapies for the prevention of hyperpigmentary disorders and an undesired browning of vegetables and fruits.
Methods
Different natural and synthetic chemical compounds have been tested as potential tyrosinase inhibitors, but the mechanism of inhibition is not known, and the quest for information regarding interaction between tyrosinase and its inhibitors is one of the recent areas of research. Computer based methods hence are useful to overcome such issues. Successful utilization of in silico tools like molecular docking simulations make it possible to interpret the tyrosinase and its inhibitor’s intermolecular interactions and helps in identification and development of new and potent tyrosinase inhibitors.
Results
The present review has pointed out the prominent role of computer aided approaches for the explication of promising tyrosinase inhibitors with a focus on molecular docking approach. Highlighting certain examples of natural compounds whose antityrosinase effects has been evaluated using computational simulations.
Conclusion
The investigation of new and potent inhibitors of tyrosinase using computational chemistry and bioinformatics will ultimately help millions of peoples to get rid of hyperpigmentary disorders as well as browning of fruits and vegetables.
Five compounds were isolated from the BuOH fraction of Polygonum bistorta (Polygonaceae). On the basis of spectral data, these compounds were established as caffeic acid, quecimeritrin, avicularin, gallic acid and protocatechuic acid. The inhibitory activities on 3 α-hydroxysteroid dehydrogenase (3 α-HSD) of isolated compounds were compared. IC50 value of isolated compounds were 133.57 μg/ml (caffeic acid), 89.1 μg/ml (quercimeritrin), 189.85 μg/ml (avicularin), 140.69 μg/ml (gallic acid) and 165.27 μg/ml (protocatechuic acid) respectively. Although all compounds showed lower inhibition activities than BuOH fraction (IC50<50 μg/ml) of Polygonum bistorta, it showed higher inhibition activities than aspirin (IC50 246.81 μg/ml).
Anthocyanin pigments in ten pigmented rice cultivars were isolated with cellulose thin-layer chromatography and preparative high performance liquid chromatography (HPLC), and further identified with conventional chromatographic techniques. Individual anthocyanins were then quantified by HPLC using a reversed ODS-5 column and detected at 280 nm. Ten rice varieties contained two major anthocyanins, cyanidin 3-glucoside and peonidin 3-glucoside. Total anthocyanin contents varied greatly in the range of 0-493 mg/100 g grain among varieties. Cyanidin 3-glucoside, an agent having important oxygen radical absorbing capacity (ORAC), was most abundant in Suwon #415 variety (470 mg/100 g grain), while Jawangdo (10 mg/100 g grain) and Ilpumbyeo (not detected) had the smallest amount of anthocyanin among the samples examined. As for the distribution ratio of individual anthocyanin, Suwon #415 was characterized by a relatively high percentage of cyanidin 3-glucoside (95.3%); whereas, Suwon #425 and Heugjinmi were characterized by a relatively larger amount of peonidin 3-glucoside.
The EtOAC extractable constituents of the bark of C. haematocephala were active against selected bacteria. Fractionation by chromatographic methods, gave known compounds p-hydroxybenzoic acid, caffeic acid, protocatechuic acid, astilbin, neo-isoastilbin, and catechin-3-O-rhamnoiside, which showed varied antibacterial activity. In addition the non-active n-C6H14 fraction gave lupeol and betulinic acid.
Thin as well as fat people may chronically underbreathe and, though their lungs are normal, the resulting hypoxia may lead to pulmonary hypertension and even to cor pulmonale. Cardiac therapy may then allow a level of breathing which partly corrects hypoxia and hypercapnia, thus breaking the vicious cycle which contributed to the heart failure initially. One cannot treat the lesion in the medullary respiratory center, but treatment of heart failure, artificial ventilation, and oxygen may, as in the present case, permit the patient to return to work. Prevention of heart failure then allows a level of breathing which partly corrects anoxia and hypercapnia and, in turn, prevents recurrent episodes of heart failure.
Hydroquinone is known to inhibit melanogenesis both in vitro and in vivo. In this study, 2% and 5% hydroquinone creams were topically applied to the hyperpigmented skin of 56 patients. Used in this way, hydroquinone was a moderately effective depigmenting agent in 80% of cases. The 2% cream appeared to be as effective therapeutically as the 5% cream and to evoke untoward side effects (primary irritation) much less often. Therapy with topically applied hydroquinone did not lead to complete disappearance of pathological hypermelanosis, but results were satisfactory enough to help most patients become less self-conscious about their pigmentary abnormalities.
Background and Design:
Melasma is an acquired, masklike, facial hyperpigmentation. The pathogenesis and treatment of melasma in black (African-American) patients is poorly understood. We investigated the efficacy of topical 0.1% all-trans-retinoic acid (tretinoin) in the treatment of melasma in black patients. Twenty-eight of 30 black patients with melasma completed a 10-month, randomized, vehicle-controlled clinical trial in which they applied either 0.1% tretinoin or vehicle cream daily to the entire face. They were evaluated clinically (using our Melasma Area and Severity Index), colorimetrically, and histologically.
Results:
After 40 weeks, there was a 32% improvement in the Melasma Area and Severity Index score in the tretinoin treatment group compared with a 10% improvement in the vehicle group. Colorimetric measurements showed lightening of melasma after 40 weeks of tretinoin treatment vs vehicle. Lightening of melasma, as determined clinically, correlated well with colorimetric measurements. Histologic examination of involved skin revealed a significant decrease in epidermal pigmentation in the tretinoin group compared with the vehicle group. Side effects were limited to a mild ''retinoid dermatitis'' occurring in 67% of tretinoin-treated patients. Among the patients in this study in comparison with comparably recruited white patients, melasma was reported to have begun at a later age and was more likely to be in a malar distribution.Conclusions: This controlled study demonstrates that topical 0.1% tretinoin lightens melasma in black patients, with only mild side effects.(Arch Dermatol. 1994;130:727-733)
Complete depigmentation of the normal skin of adult male blacks was procured by the daily application for five to seven weeks of a formula consisting of 0.1% tretinoin, 5.0% hydroquinone, 0.1% dexamethasone, and hydrophilic ointment. Depigmentation was not attainable when any one of the components was omitted.The formula was therapeutically effective in treatment of melasma, ephelides, and postinflammatory hyperpigmentation. Senile lentigines were resistant to this therapy.
A simple method for the isolation of γ-oryzanol from rice bran acid oil has been developed. The basis of the present isolation protocol is calcium ion induced precipitation of anionic micellar aggregates. Rice bran acid oil, a byproduct of rice bran oil processing industries, is subjected to conventional vacuum distillation to remove free fatty acids. Aqueous alkaline hydrolysis of the resultant residue, upon dilution with water, produces anionic micellar aggregates containing solubilized γ-oryzanol. Addition of calcium ions to this aqueous micellar aggregate induces instant coprecipitation of the calcium salts of the fatty acids and the aggregate-associated γ-oryzanol. The dried precipitate is extracted with ethyl acetate. Ethyl acetate is evaporated from the extract, and γ-oryzanol is purified from the residue by silica gel column chromatography. Experimental details for the isolation and characterization procedure are described. The present method will give ready access to the physiologically beneficial and value-added pharmaceutical product γ-oryzanol. Keywords: γ-Oryzanol; ferulic acid esters; CAD esters; HPLC; LSIMS
Ethanolic extracts of buckwheat (Fagopyrum esculentum Möench) hulls were separated by Sephadex LH-20 column chromatography into eight fractions. Five of the fractions exhibited peroxyl radical-scavenging activity by inhibiting the oxidation of methyl linoleate in solution. Two of the antioxidant fractions contained proanthocyanidins (condensed tannins) from the color reaction of these fractions with HCl under heat treatment. Five antioxidant compounds were isolated by preparative HPLC and identified as quercetin, hyperin, rutin, protocatechuic acid, and 3,4-dihydroxybenzaldehyde. The contents of these active compounds in the buckwheat hulls were as follows: protocatechuic acid (13.4 mg/100 g of dried hulls), 3,4-dihydroxybenzaldehyde (6.1 mg/100 g), hyperin (5.0 mg/100 g), rutin (4.3 mg/100 g), and quercetin (2.5 mg/100 g). Besides the isolation of these compounds, two major compounds that showed no peroxyl radical-scavenging activity in the extract were isolated and identified as vitexin and isovitexin. Keywords: Fagopyrum esculentum; antioxidant activity; flavonoids; phenolic compounds; proanthocyanidin
The difference in the distribution of sesamin, sesamolin, sesaminol glucosides and sesamolinol components in representative varieties of sesame were compared. Quantitation was achieved by HPLC determination using an external standard. The most abundant lignan glucosides in sesame seed were sesaminol triglucoside. The content of sesaminol triglucoside in 100 g seeds ranged from 14.1 to 91.3 mg with an average value of 68.4 mg; that of sesaminol diglucoside from 8.2 to 18.3 mg with an average value of 11.6 mg; and that of sesaminol monoglucoside from 5.4 to 19.5 mg with an average value of 8.3 mg. The total content of sesaminol glucoside was 88.3 mg in 100 g of sesame seeds. Also, the sesamolinol content in 100 g sesame seed ranged from 17.6 to 28.5 mg, the average being 20.5 mg. Within
Constituents of the fruit of Amomum tsao-ko were investigated following a preliminary screening of the antioxidant activity of several extracts of the fruit of this
plant that showed that the dichloromethane extract and the ethyl acetatesoluble and water-soluble fractions of the 70% aqueous
acetone extract had higher activity than α-tocopherol and butylated hydroxytoluene (BHT). Eleven compounds were isolated from
the ethyl acetate-soluble fraction, and their structures were elucidated as (+)-hannokinol (1), meso-hannokinol (2), (+)-epicatechin (3), (−)-catechin (4), β-sitosterol (5), β-sitosterol 3-O-glucoside (6), 2,6-dimethoxyphenol (7), protocatechualdehyde (8), protocatechuic acid (9), vanillic acid (10), and p-hydroxybenzoic acid (11) based on mass and various nuclear magnetic resonance (NMR) spectroscopic techniques. This is the first isolation of epicatechin
and catechin from the genus Amomum. The radical scavenging activity of the isolated compounds was evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and colorimetric
and electron spin resonance (ESR) analyses. The antioxidant activity of the compounds was also determined based on the oxidative
stability index (OSI). The catechins and catechol derivatives showed strong activities in both the DPPH radical scavenging
activity and antioxidant activity assays.
Progress in the plant polyphenol oxidases in the period 1978–1986 is summarized. Methodology, occurrence, properties and physiological function of laccases and catechol oxidases are critically reviewed. The advances in the understanding of reaction mechanisms are cited. The plant polyphenoloxidases remain enzymes in search of a function.
"Graduate Program in Food Science." Includes abstract. Thesis (M.S.)--Rutgers University, 1998. Includes bibliographical references (leaves 72-75).
Complete depigmentation of the noraml skin of adult male blacks was procured by the daily application for five to seven weeks of a formula consisting of 0.1% tretinoin, 5.0% hydroquinone, 0.1% dexamethasone, and hydrophilic ointment. Depigmentation was not attainable when any one of the components was omitted. The formula was therapeutically effective in treatment of melasma, ephelides, and postinflammatory hyperpigmentation. Senile lentigines were resistant to this therapy.
15 patients with melasma were treated with betamethasone 17-valerate in a cream base containing DMSO. One patient with secondary pigmentation was also entered in the trial. In nine patients results were favourable and in three results were moderate. This effect could be ascribed to the steroid.
--Melasma is a difficult medical problem to treat. Hydroquinone is administered to many patients, but it is unstable and local irritation and dermatitis may develop after a prolonged use at a high concentration. This study introduces a new depigmenting agent, N-acetyl-4-S-cysteaminylphenol, for better management of melanoderma in patients with melasma.
--Our study, based on a retrospective observation of 12 patients using 4% N-acetyl-4-S-cysteaminylphenol in oil-in-water emulsion, showed a complete loss (8%), a marked improvement (66%), or a moderate improvement (25%) of melasma lesions. Visible changes of melanoderma can be seen in 2 to 4 weeks after daily topical application. This depigmentation was associated with a decrease in the number of functioning melanocytes and in the number of melanosomes transferred to keratinocytes. N-acetyl-4-S-cysteaminylphenol is the tyrosinase substrate, and, on exposure to tyrosinase, it formed a melanin-like pigment.
--A phenolic thioether, N-acetyl-4-S-cysteaminylphenol, is a new type of depigmenting agent for the better management of melasma. It is much more stable and less irritating to the skin than hydroquinone, and it is specific to melanin-synthesizing cells.
Melasma is a macular hypermelanosis of the sun-exposed areas of the face and neck. The clinical efficacy of azelaic acid (20%) and hydroquinone creams (2%) in the treatment of this benign pigmentary disorder was compared in a randomized, double-blind study with 155 patients of Indo-Malay-Hispanic origin. The creams were applied twice daily. A broad spectrum sunscreen was used concomitantly. Over a period of 24 weeks, 73% of the azelaic acid patients, compared with 19% of the hydroquinone patients, had good to excellent overall results, as measured by the reduction of melasma pigmentary intensity and lesion size. Transient mild to moderate irritant reactions were initially seen with both test drugs.
Azelaic acid (COOH(CH2)7COOH), is a medium chain-length saturated, 9-carbon atom dicarboxylic acid, which has recently been shown to have important biologic activities and some useful practical therapeutic applications. It can be obtained by oxidation of fatty acids, such as oleic acid, which are unsaturated in the 9-C position, and in humans it has been reported present in the urine of noncompensated diabetics and of patients with congenital inability to oxidize monocarboxylic acids.1During investigations on the causation of the hypochromia in pityriasis versicolor, dicarboxylic acids of chain-length C6–C12 were found to be formed in cultures of Pityrosporum to which unsaturated fatty acids with double bonds in the 6 to 12 positions were added.2,3 An ascending gradient of competitive anti-tyrosinase activity of the diacids was demonstrated and in another study,4 damage to melanocytes. Because of these findings, it seemed possible the diacids might be involved in the hypochromia of pityriasis versicolor, and perhaps useful in the topical treatment of hyperpigmentary disorders as an alternative to phenolic compounds, such as monobenzoyl ester of hydroquinone, which are alternative substrates of tyrosinase. These latter often produce residual hypochromia of both hyperpigmented and adjacent uninvolved normal skin, which is a disadvantage of their use. The final choice of dicarboxylic acid for original application and investigation fell upon azelaic acid, mainly because it occupies the middle range of anti-tyrosinase activity, is relatively cheap, and more easily soluble and capable of being incorporated into a base cream than those at the higher level of activity. A 15% cream was originally employed, but a 20% one is now standard; occasionally, we have studied the effects of a 35% cream. Early limited open trials established a beneficial effect of the cream on some hyperpigmentary disorders and showed that it had no clinical depigmenting effect on normal skin.2,5 These preliminary results encouraged further clinical studies extending over the years, and initiated parallel laboratory investigations aimed at elucidating the mechanism of action of azelaic acid. An outline of these will be given first because they provide a background and rationale (often post hoc) for the clinical use of the diacid.
Recent elucidation of regulatory mechanisms of eu- and pheomelanogenesis has led us towards an exciting new era of melanogenesis control. I will chiefly address our progress on inhibitory control of melanogenesis from the macromolecular level to human skin colour.
In the past, the exploration and search for skin depigmenting agents has been focussed on and initiated from substances which can suppress isolated tyrosinase in vitro. Now, as I have classified below, many new melanogenic inhibitors have been discovered which, in spite of their non-suppressive effect on isolated naked tyrosinase, suppress melanin formation in the living pigment cell in vitro as well as in the natural world. I will also discuss a recently found unique disorder: unilateral suppression of mixed melanogenesis.
Melasma is an acquired, masklike, facial hyperpigmentation. The pathogenesis and treatment of melasma in black (African-American) patients is poorly understood. We investigated the efficacy of topical 0.1% all-trans-retinoic acid (tretinoin) in the treatment of melasma in black patients. Twenty-eight of 30 black patients with melasma completed a 10-month, randomized, vehicle-controlled clinical trial in which they applied either 0.1% tretinoin or vehicle cream daily to the entire face. They were evaluated clinically (using our Melasma Area and Severity Index), colorimetrically, and histologically.
After 40 weeks, there was a 32% improvement in the Melasma Area and Severity Index score in the tretinoin treatment group compared with a 10% improvement in the vehicle group. Colorimetric measurements showed lightening of melasma after 40 weeks of tretinoin treatment vs vehicle. Lightening of melasma, as determined clinically, correlated well with colorimetric measurements. Histologic examination of involved skin revealed a significant decrease in epidermal pigmentation in the tretinoin group compared with the vehicle group. Side effects were limited to a mild "retinoid dermatitis" occurring in 67% of tretinoin-treated patients. Among the patients in this study in comparison with comparably recruited white patients, melasma was reported to have begun at a later age and was more likely to be in a malar distribution.
This controlled study demonstrates that topical 0.1% tretinoin lightens melasma in black patients, with only mild side effects.
Melasma is a common disorder of cutaneous hyperpigmentation predominantly affecting the faces of women. Little is known about the aetiology of melasma, and treatment is frequently disappointing. Topical tretinoin is of benefit in treating other forms of hyperpigmentation, for example liver spots, and we therefore investigated its effectiveness in melasma. Thirty-eight women completed a randomized, vehicle-controlled study, in which they applied 0.1 % tretinoin (n=19) or vehicle cream (n=19) once daily to the face for 40 weeks.
At the end of treatment 13 (68%) of 19 tretinoin-treated patients were clinically rated as improved or much improved, compared with 1 (5%) of 19 in the vehicle group (P=0.0006). Significant improvement first occurred after 24 weeks of tretinoin treatment. Colorimetry (an objective measure of skin colour) demonstrated a 0.9 unit lightening of tretinoin-treated melasma and a 0.3 unit darkening with vehicle (P=0.01); these results correlated with clinical lightening (r=0.55, P=0.0005). Histologically, epidermal pigment was reduced 36% following tretinoin treatment, compared with a 50% increase with vehicle (P=0.002). Reduction in epidermal pigment also correlated with clinical lightening (r=0.41, P=0.01). Moderate cutaneous side-effects of erythema and desquamation occurred in 88% of tretinoin-treated and 29% of vehicle-treated patients.
Topical 0.1% tretinoin produces significant clinical improvement of melasma, mainly due to reduction in epidermal pigment, but improvement is slow.
1. The effect of the phenolic compounds protocatechuic acid, chlorogenic acid, tannic acid, gallates and silybin on ethoxyresorufin O-dealkylase (CYP1A1), methoxyresorufin O-dealkylase (CYP1A2) and pentoxy-O-dealkylase (CYP2B) was examined in mouse liver microsomes from induced animals. 2. All compounds tested could inhibit cytochrome P450-mediated enzyme activities, but to different extents. Tannic acid was the most potent inhibitor, especially toward EROD activity with an IC50=2.6 microM. Synthetic dodecyl gallate was also relatively selective toward this enzyme activity with an IC50=120 microM. 3. Protocatechuic acid, chlorogenic and silybin were more selective towards PROD and MROD activities. Their relative inhibitory potency for PROD activity was as follows: chlorogenic acid > protocatechuic acid > silybin > dodecyl gallate > propyl gallate. Protocatechuic acid was a more effective inhibitor of MROD activity than chlorogenic acid, and propyl gallate more effective than dodecyl gallate. Thus, no clear structure-activity or selectivity relationship was observed. 4. Analysis of the kinetics of inhibition revealed that the inhibition in most cases was non-competitive in nature.
Olive oil contains several phenolic compounds with antioxidant activity, whose levels depend strongly on the kind of cultivar grown, fruit ripening effects and the oil extraction process. Therefore, the beneficial effects exerted by olive oil consumption on the resistance of low density lipoproteins (LDLs) to oxidation depend not only on an increased intake of mono-unsaturated fatty acids (e.g. oleate) which are less prone to oxidation, but also phenolic antioxidants. The aim of this study was to analyze in vitro effects exerted on the oxidative modification of Cu-stimulated human LDL by two olive oil biophenols, i.e. 3,4-dihydroxyphenylethanol-elenolic acid (3,4-DHPEA-EA) and protocatecuic acid. These compounds have not been investigated in as much detail as the better-known olive oil biophenols - such as tyrosol (p-HPEA), o-coumaric acid, vanillic acid, caffeic acid, oleuropein and 3,4-dihydroxyphenylethanol (3,4-DHPEA). Modification of LDL was tested by measuring the formation of intermediate and end products of lipid peroxidation such as conjugated dienes, lipid hydroperoxides, cholesterol and cholesteryl ester oxides, as well as studying the decrease in oxidizable substrates like polyunsaturated fatty acids. In addition, the increase in LDL negative charges was evaluated. The results demonstrate the two-tested olive oil biophenols show high antioxidant activities. In particular, protocatecuic acid and 3,4-DHPEA-EA show an antioxidant activity comparable with that of caffeic acid, oleuropein and 3,4-DHPEA. They are not only able to retard lipid peroxidation, but also to reduce the extent of its activity.
Rice is a staple diet in Asia, where the incidence of breast and colon cancer is markedly below that in the Western world. We investigated potential colon and breast tumor-suppressive properties of rice, testing the hypothesis that rice contains phenols that interfere with the proliferation or colony-forming ability of breast or colon cells. Brown rice, its white milled counterpart, and bran from brown rice were boiled and extracted with ethyl acetate. The extracts were analyzed by high pressure liquid chromatography-mass spectrometry. Eight phenols, protocatechuic acid, p-coumaric acid, caffeic acid, ferulic acid, sinapic acid, vanillic acid, methoxycinnamic acid, and tricin, were identified in the extracts of bran and intact brown rice. These extracts were separated into nine fractions by column chromatography. The effect of bran extract and its fractions at 100 microg/ml on cell viability and colony-forming ability of human-derived breast and colon cell lines was assessed. Bran extract decreased numbers of viable MDA MB 468 and HBL 100 breast cells and colon-derived SW 480 and human colonic epithelial cells as judged by the 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4 -sulfophenyl)-2H-tetrazolium assay. It also reduced colony formation of SW 480 colon and MDA MB 468 breast cells. Of the eight phenols identified in the brown rice bran, when applied at 50 microM, caffeic acid decreased numbers of all cell types except HBL 100. Tricin, ferulic acid, and methoxycinnamic acid interfered with cell viability in one or more cell lines. Tricin (50 microM) and the other phenols (200 microM) inhibited colony formation of SW 480 cells. Clonogenicity of MDA MB 468 cells was inhibited by caffeic acid, ferulic acid, and tricin (50 microM). Tricin was the most potent anticlonogenic of the compounds with IC50s of 16 microM in the SW 480 colon cells and 0.6 microM in the MDA MB 468 breast cells. The results suggest that: (a) brown rice and bran contain compounds with putative cancer chemopreventive properties; (b) certain phenols contained in brown rice bran, e.g., tricin, may be associated with this activity; and (c) these phenols are present at much lower levels in white than in brown rice. Thus, the consumption of rice bran or brown rice instead of milled white rice may be advantageous with respect to cancer prevention.
Isolation of oryzanol concentrate from rice bran oil
- R P Singh
- R K Khanna
- A Mathur
- R Srivastava
Singh, R. P.; Khanna, R. K.; Mathur, A.; Srivastava, R. Isolation
of oryzanol concentrate from rice bran oil. J. Oil Technol. Assoc.
India 2000, 32, 55-58.
Coumarins, benzoic acids and terpenoids from Palicourea demissa Received for review May 21
- El
- H R Seedi
El-Seedi, H. R. Coumarins, benzoic acids and terpenoids from Palicourea demissa. ReV. Latinoam. Quim. 1999, 27, 13-16. Received for review May 21, 2003. Revised manuscript received August 15, 2003. Accepted September 2, 2003. JF030388S
Antioxidant activity and phenolic acid content in rosemary (Rosmarinus officinalis L.) and myrtle (Myrtus communis)
- A Hadafi
- M Ismaili Alaoui
- A Chaouch
- B Benjilali
- S Zrira
Hadafi, A.; Ismaili Alaoui, M.; Chaouch A.; Benjilali, B.; Zrira,
S. Antioxidant activity and phenolic acid content in rosemary
(Rosmarinus officinalis L.) and myrtle (Myrtus communis). RiV.
Ital. EPPOS 1998, 325-340.
Phytic acid and myo-inositol from ricebran
- T N B Kaimal
Kaimal, T. N. B. Phytic acid and myo-inositol from ricebran. J.
Oil Technol. Assoc. India 1998, 30, 183, 189, 191, 193, 195.
Antioxidant Compounds from Buckwheat (Fagopyrum esculentum Moeench) Hulls Baer-Dubowska, W.; Szaefer, H.; Krajka-Kuzniak, V. Inhibition of murine hepatic cytochrome P450 activities by natural and synthetic phenolic compounds
- M Watanabe
- Y Ohshita
- T Tsushida
Watanabe, M.; Ohshita, Y.; Tsushida, T. Antioxidant Compounds from Buckwheat (Fagopyrum esculentum Moeench) Hulls. J. Agric. Food Chem. 1997, 45, 1039-1044. (26) Baer-Dubowska, W.; Szaefer, H.; Krajka-Kuzniak, V. Inhibition of murine hepatic cytochrome P450 activities by natural and synthetic phenolic compounds. Xenobiotica 1998, 28, 735-743.
Coumarins, benzoic acids and terpenoids from Palicourea demissa
- H R El-Seedi
El-Seedi, H. R. Coumarins, benzoic acids and terpenoids from
Palicourea demissa. ReV. Latinoam. Quim. 1999, 27, 13-16.
Revised manuscript received
- Miyazawa
Received for review May 21, 2003. Revised manuscript received August 15, 2003. Accepted September 2, 2003. JF030388S 6956 J. Agric. Food Chem., Vol. 51, No. 24, 2003 Miyazawa et al.
El-Seedi, H. R. Coumarins, benzoic acids and terpenoids from Palicourea demissa
(29) El-Seedi, H. R. Coumarins, benzoic acids and terpenoids from
Palicourea demissa. ReV. Latinoam. Quim. 1999, 27, 13-16.
Topical use of hydroquinine as a depigmenting agent
- K A Arandt
- T B Fitzpatrick
Arandt, K. A.; Fitzpatrick, T. B. Topical use of hydroquinine
as a depigmenting agent. J. Am. Med. Assoc. 1965, 194, 117-119.
- Jimbow K.