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The significance of arbutin and its derivatives in therapy and cosmetics

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Abstract

The ongoing studies on biological activity of arbutin and its derivatives show a wide range of their possible applications. Arbutin containing plant substances are used mostly in the treatment of urinary tract infections (UTI). However, several in vitro and in vivo studies revealed anti-melanogenic activity of arbutin, which can be useful in hyperpigmentation therapy. Moreover, it was found that the modifications in arbutin structure lead to an increase of the above-mentioned activity. The lack of significant adverse effects of arbutin and its derivatives makes them a valuable alternative to hydroquinone. Therefore, an increasing interest in arbutin and its derivatives is observed especially in the cosmetics industry.

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... It has good compatib with various components of cosmetics. Furthermore, it is stable under ultraviolet irra tion [68,69]. Compared to GC-MS, LC-QTOF-MS is a more in-depth data test. ...
... loss of mass at stage II was relatively slow, which showed that the pyrolysis rate steady. The mass loss mainly owed to the depolymerization and recombination of a sm [68,69] Isocryptotanshinone is a natural bioactive product with anti-cancer effects [70], it's an effective STAT3 inhibitor induction lung cancer cell apoptosis and promotion of autophagy [62]. One of the active chemical composition is celastrol, which is also known as South Snake. ...
... It has good compatibility with various components of cosmetics. Furthermore, it is stable under ultraviolet irradiation [68,69]. Compared to GC-MS, LC-QTOF-MS is a more in-depth data test. ...
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Biomass has been recognized as the most common source of renewable energy. In recent years, researchers have paved the way for a search for suitable biomass resources to replace traditional fossil fuel energy and provide high energy output. Although there are plenty of studies of biomass as good biomaterials, there is little detailed information about Staphylea holocarpa wood (S. holocarpa) as a potential bio-oil material. The purpose of this study is to explore the potential of S. holocarpa wood as a bio-oil. Nanocatalyst cobalt (II) oxide (Co3O4) and Nickel (II) oxide (NiO) were used to improve the production of bio-oil from S. holocarpa wood. The preparation of biofuels and the extraction of bioactive drugs were performed by the rapid gasification of nanocatalysts. The result indicated that the abundant chemical components detected in the S. holocarpa wood extract could be used in biomedicine, cosmetics, and biofuels, and have a broad industrial application prospect. In addition, nanocatalyst cobalt tetraoxide (Co3O4) could improve the catalytic cracking of S. holocarpa wood and generate more bioactive molecules at high temperature, which is conducive to the utilization and development of S. holocarpa wood as biomass. This is the first time that S. holocarpa wood was used in combination with nanocatalysts. In the future, nanocatalysts can be used to solve the problem of sustainable development of biological resources.
... L-Ascorbic acid ( Figure 1) and its derivatives, such as kojic acids (Figure 1), are combined with cosmetics for their antioxidant activities against tyrosinase and for their chelating properties to copper atoms in metalloenzyme tyrosinase. In addition, α-arbutin (manufactured by Shiseido; depicted in Figure 1) and rucinol (4-butyl-benzol-1,3-diol manufactured by POLA; depicted in Figure 1) have been included in functional cosmetics as anti-melanogenic ingredients for their competitive inhibition activities of tyrosinase [16,17]. On the contrary, rhododenol (4-hydroxyphenyl-2-butanol; depicted in Figure 1) was manufactured by Kanebo but is currently banned for causing vitiligo [18]. ...
... In the meantime, the SP aglycones tend to display advances in their in vivo absorption and metabolism rates, and when they are combined as formulations, their chemical stability is known to decline. However, when it comes to their corresponding glycosides, although their bio-absorption rate is not as high, their solubility and bioavailability can be enhanced more than aglycones [1,3,16,18]. In this regard, several studies [22][23][24][25][26][27][28] in which various organic or enzymatic synthesis methods were employed have consistently reported the manufacture of a series of SP glycosides. ...
... Indeed, the enzyme displayed the lowest K m value (0.16 mM) for the glucosylation of HPP2 compared to those for HPP3 (0.22 mM), displaying StSPGT's preference for HPP2 as the acceptor substrate over HPP3. These apparent K m values appear to be comparable to those reported for other microbialor plant-origin simple phenolic glycosyltransferases [1,16,22,28]. Depending upon the donor substrates, several fold differences were found in the K m values; 0.16 and 0.22 mM when a Glc moiety was incorporated into each aglycone vs. 0.41 and 0.50 mM when a 2 dGlc-moiety was. In particular, the glycosyl donor supplement, especially UDP-Glc onto StSPGT's enzymatic reactions with HPP2 aglycone, gave the highest turnover number (k cat = 19.41 ...
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Article
Simple phenolics (SPs) and their glycosides have recently gained much attention as functional skin-care resources for their anti-melanogenic and antioxidant activities. Enzymatic glycosylation of SP aglycone make it feasible to create SP glycosides with updated bioactive potentials. Herein, a glycosyltransferase (GT)-encoding gene was cloned from the fosmid libraries of Streptomyces tenjimariensis ATCC 31603 using GT-specific degenerate PCR followed by in silico analyses. The recombinant StSPGT was able to flexibly catalyze the transfer of two glycosyl moieties towards two SP acceptors, (hydroxyphenyl-2-propanol [HPP2] and hydroxyphenyl-3-propanol [HPP3]), generating stereospecific α-anomeric glycosides as follows: HPP2-O-α-glucoside, HPP2-O-α-2″-deoxyglucoside, HPP3-O-α-glucoside and HPP3-O-α-2″-deoxyglucoside. This enzyme seems not only to prefer UDP-glucose and HPP2 as a favorable glycosyl donor and acceptor, respectively but also differentiates the positional difference of the hydroxyl function as acceptor catalytic sites. Paired in vitro and in vivo antioxidant assays represented SPs and their corresponding glycosides as convincing antioxidants in a time- and concentration-dependent manner by scavenging DPPH radicals and intracellular ROS. Even compared to the conventional agents, HPP2 and glycoside analogs displayed improved tyrosinase inhibitory activity in vitro and still suppressed in vivo melanogenesis. Both HPP2 glycosides are further likely to exert the best inhibitory activity against elastase, eventually highlighting these glycosides with enhanced anti-melanogenic and antioxidant activities as promising anti-wrinkle hits.
... Similarly, arbutin from leaves is light and pH stable, making it suitable for uses in cosmetics, while through the processes of hydrolysis and oxidation in the aqueous matrix, it can be transformed into benzoquinone, which has antibacterial properties [135,136]. For this reason, and due to the fact that arbutin is a good alternative to hydroquinone, it is suitable for the apical products for the treatment of hyperpigmentation [137]. Figure 5 summarizes the economic properties and further economic prospects of strawberry tree fruits and leaves. ...
... it can be transformed into benzoquinone, which has antibacterial properties [135,136]. For this reason, and due to the fact that arbutin is a good alternative to hydroquinone, it is suitable for the apical products for the treatment of hyperpigmentation [137]. Figure 5 summarizes the economic properties and further economic prospects of strawberry tree fruits and leaves. ...
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Article
The strawberry tree (Arbutus unedo L.) is a Mediterranean plant known for the traditional use of its fruits and leaves due to their health benefits. Thus, it has been used for years in folk medicine to relieve various health conditions such as urological and kidney problems, dermatological, cardiovascular and gastrointestinal diseases. The fruits are traditionally used for making jams, jellies, and strong alcoholic beverages, while the leaves are mostly used for preparing tea. Since leaves were more researched, previous results indicated that they have important biological effects, so further research should focus on the fruits. Due to its chemical composition, rich polyphenolic profile and the biological potential derived from it, the plant has great prospects for the production of functional foods and nutraceuticals. However, the plant’s potential is underutilized in terms of processing. Therefore, this review summarizes the properties and the potential of the fruits and leaves of A. unedo and their possible benefits for processing with respect to agricultural, nutritive, biological and economic values.
... Arbutin is an active compound widely used in the cosmetic industry because of its ability to inhibit human tyrosinase activity [67]. The beneficial properties of arbutin on the integumentary system are based on its powerful ability to treat hyperpigmentation [68]. The pharmacological properties of arbutin also include urinary antiseptic effect [69], antimicrobial agent [70], anti-inflammatory effect [68], anti-diabetic effect [71], and antioxidant agent [72]. ...
... The beneficial properties of arbutin on the integumentary system are based on its powerful ability to treat hyperpigmentation [68]. The pharmacological properties of arbutin also include urinary antiseptic effect [69], antimicrobial agent [70], anti-inflammatory effect [68], anti-diabetic effect [71], and antioxidant agent [72]. Other major compounds proved their ability to provide different pharmacological properties [73]. ...
Article
Fruit vinegar is a popular functional food with multifaceted purposes, it is widely used in traditional medicine as a natural agent for many health critical conditions. The chemical composition of vinegars varies depending on their raw matter and the used technique to produce it. The current study aimed to characterize the physicochemical (pH, conductivity, °Brix, color parameters, total polyphenols content, total flavonoid content, total antioxidant capacity, and antiradical DPPH effect) and phytochemical contents of Moroccan fruit vinegars. The results showed that the physicochemical parameters are in the range of 3.4–3.72, 2.97–4.94%, 2.81–5.94 mS/cm, 4.85–7.95°, 1.019–1.03 for pH, acidity, conductivity, °Brix, and density. Concerning phytochemical content showed that FV1 has a high content of total phenolic content and vitamin C and exhibited high antioxidant activities. A total of 44 compounds were detected in different amounts and the prominent phenolic compounds were arbutin (77.16% for FV1, 21.76% for FV2, 53.33% for FV3), trans-ferulic acid (3.74% for FV1, 29.88% for FV2, 23.32% for FV3), ferulic acid (2.37% for FV1, 21.25% for FV2, 15.99% for FV3), apigenin (3.47% for FV1, 6.02% for FV2, 0.75% for FV3), trans-cinnamic acid (0.49% for FV1, 1.10% for FV2, 2.37% for FV3), and chlorogenic acid (0.99% for FV1, 1.43% for FV2, 0.76% for FV3). The findings of the current work showed that the fruit vinegars contain numerous bioactive compounds known for their ability to fulfill the basic requirements of being efficacious and safe in vivo.
... The large amount of tannins in the bark make the species useful for tanning (Gomes et al. 2010). Moreover, several chemical compounds with bioactive properties have been identified in different parts of the plant with applications in the pharmaceutical, cosmetic and food industries (Migas and Krauze-Baranowska 2015). ...
... Because of the several bioactivities identified, these natural compounds can be exploited for pharmaceutical and chemical applications in the prevention or treatment of several human diseases. In fact, arbutin is already used by cosmetic industries as a skin whitening agent, and along with its precursor hydroquinone, is used in the formulation of commercial remedies for the treatment of urinary infections (Migas and Krauze-Baranowska 2015;Jurica et al. 2017). Due to the economic value of arbutin, our group has been working on the development of a biotransformation protocol in order to produce arbutin (data not published). ...
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Article
Arbutus unedo L. (strawberry tree, Ericaceae) is a woody species with a circum-Mediterranean distribution. It has considerable ecological relevance in southern European forests due to its resilience to abiotic and biotic stressors. Its edible red berries are used in the production of traditional products, including an expensive spirit. Several compounds extracted from the species have bioactive properties used by the cosmetic and pharmaceutical industries. The strawberry tree has gone from a neglected species to become a highly valuable crop with large cultivated areas in southern European and North African countries. Due to an increasing demand from farmers for plants with improved features, researchers have been trying to improve this species through conventional and biotechnological tools, focusing mainly on population analysis using molecular markers, in vitro cloning, tolerance to biotic and abiotic stresses, and intraspecific crosses to obtain genotypes with new characteristics. The objective of this review is to gather and update information about the species and make it available to researchers and stakeholders. Future research areas that are considered a priority for this species are highlighted.
... Arbutin (p-hydroxyphenyl-β-D-glucopyranoside) is a bioactive hydrophilic polyphenol with two isomers including alpha-arbutin (4-hydroxyphenyl-α-glucopyranoside) and β-arbutin (4-hydroxyphenylβ-glucopyranoside) (Couteau & Coiffard, 2016). It has been used as a medicinal plant in phytotherapy and phytocosmetics (Migas & Krauze-Baranowska, 2015). It is obtained from various types of natural and synthetic sources including various species of plants, enzymatic processes, and metabolic engineering of microorganisms ( Figure 1 and Table 1). ...
... In various studies, evaluation of oral administration of arbutin showed that arbutin and other arbutin-rich herbal preparations can metabolize into hydroquinone and glucose in the liver by the process of β-glucosidase. It then forms conjugations with glucuronic and sulfuric acids that are rapidly eliminated through urine and it is not a significant threat (Jurica, Benkovi c, Sikiri c, Kopjar, & Brči c Karačonji, 2020;Migas & Krauze-Baranowska, 2015;Schindler et al., 2002). ...
Article
Cosmetic dermatology preparations such as bleaching agents are ingredients with skin‐related biological activities for increasing and improving skin beauty. The possibility of controlling skin hyperpigmentation disorders is one of the most important research goals in cosmetic preparations. Recently, cosmetics containing herbal and botanical ingredients have attracted many interests for consumers of cosmetic products because these preparations are found safer than other preparations with synthetic components. However, high‐quality trial studies in larger samples are needed to confirm safety and clinical efficacy of phytotherapeutic agents with high therapeutic index. Arbutin (p‐hydroxyphenyl‐β‐d‐glucopyranoside) is a bioactive hydrophilic polyphenol with two isomers including alpha‐arbutin (4‐hydroxyphenyl‐α‐glucopyranoside) and β‐arbutin (4‐hydroxyphenyl‐β‐glucopyranoside). It is used as a medicinal plant in phytopharmacy. Studies have shown that alpha‐arbutin is 10 times more effective than natural arbutin. A comparison of IC50 values showed that α‐arbutin (with concentration 2.0 mM) has a more potent inhibitory activity on human tyrosinase against natural arbutin (with higher concentration than 30 mM). A review of recent studies showed that arbutin could be beneficial in treatment of various diseases such as hyperpigmentation disorders, types of cancers, central nervous system disorders, osteoporosis, diabetes, etc. This study was designed to describe the therapeutic efficiencies of arbutin.
... The research accelerated as the findings disfavored hydroquinone use for its undesirable side effects [3]. Therefore, β-arbutin (Fig. 1), a natural plant substance, and its synthetic counterpart, α-arbutin came to the center of attention [4]. However, despite the valuable works, the findings do not seem to be conclusive so that, in some aspects, they have increased the confusion. ...
... To avoid the effect of the accompanying molecules and the other environmental parameters on the enzyme activity [4], Qin et al. (2014) examined the impact of α-arbutin on MT. They showed that α-arbutin could inhibit cresolase (monophenolase) activity of MT but activated its catecholase activity [9]. ...
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Article
As a safe substitute for hydroquinone, β-arbutin, a natural plant substance, and its synthetic counterpart, α-arbutin, are used in depigmentation formulations. However, there are debatable points regarding the impact of arbutin on tyrosinase and the pigmentation process. To shed light on this issue, the effects of Pyrus biossieriana leaves extract (PbLE) and β-arbutin, extracted from PbLE, on mushroom tyrosinase (MT) were comprehensively examined. The study was focused on cresolase activity as the characteristic reaction of a tyrosinase. Kinetics studies disclosed that β-arbutin can modulate MT monophenolase activity from inhibition to activation or vice versa. β-Arbutin inhibited l-tyrosine (LTy) oxidation at concentrations < 0.3 mM but it increased (more than 400%) the enzymatic oxidation of l-tyrosine at the concentrations > 0.3 mM. An opposite pattern (activation then inhibition) was observed when a synthetic substrate was used instead of LTy. Computational studies, focused on the heavy chain of MT, indicated that β-arbutin effect could be overruled by the enzyme's ability to provide the ligand with a non-specific binding site (MTPc). A plausible mechanism was presented to show the influence of MTPc on the substrate pose in the active site. The possible determinant correlation between the findings of this research and the current studies on human tyrosinase role in the pigmentation process has been presented.
... β-arbutin (10) is a simple phenol glucoside known for its antibacterial activity. Therefore, arbutin-containing plant substances are used mostly in the treatment of urinary tract infections [64]. β-arbutin (10) also possesses an anti-inflammatory effect. ...
... The lack of significant adverse effects of arbutin and its derivatives makes them a valuable alternative to hydroquinone. Therefore, an increasing interest in arbutin and its derivatives is observed especially in the cosmetics industry [64]. ...
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Three germacranolides, as well as five flavonoids, natural steroid and simple phenolic compounds, were isolated from the inflorescence of Stizolophus balsamita growing in Iran. The paper presents active compounds found for the first time in the inflorescence of this species. The flavonoids, simple phenolic compounds and natural steroids have been isolated for the first time in the genus Stizolophus. The MTT assay was employed to study in vitro cytotoxic effects of the taxifolin against human fibroblasts. We also evaluate the possible biological properties/cosmetic effects of Stizolophus balsamita extract and taxifolin on the human skin. Sixty healthy Caucasian adult females with no dermatological diseases were investigated. We evaluate the effects of S. balsamita extract and taxifolin on skin hydration and transepidermal water loss (TEWL). It was revealed that S. balsamita extract might decrease TEWL level and fixed the barrier function of the epidermis. The presence of bioactive phytochemical constituents in S. balsamita inflorescences makes them a valuable and safe source for creating new cosmetics and medicines.
... Additionally known as p-hydroxyphenyl-β-d-glucopyranoside, arbutin is a bioactive hydrophilic polyphenol that has two isomers such as α-arbutin and β-arbutin [59]. Arbutin and its derivatives can directly control the overproduction of melanin by converting tyrosinase into L-DOPA (levodopa) and obstructing the tyrosinase activity without altering the mRNA expression [60]. Arbutin can introduce anti-inflammatory activity by decreasing the production of nitric oxide (NO) and expression of iNOS and cyclooxygenase-2 (COX-2) in lipopolysaccharide-stimulated BV2 cells (murine microglial cells) which also simultaneously suppressed the production of pro-inflammatory cytokines such as interleukin-1β (IL-1β) and tumor necrosis factor-α (TNF-α) and monocyte chemoattractant protein-1 (MCP-1) [61]. ...
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Article
Herbal products have been used in traditional systems of medicine and by ethnic healers for ages to treat various diseases. Currently, it is estimated that about 80% of people worldwide use herbal traditional medicines against various ailments, partly due to easy accessibility and low cost, and the lower side effects they pose. Bergenia ligulata, a herb ranging from the Himalayas to the foothills, including the northeastern states of India, has traditionally been used as a remedy against various diseases, most prominently kidney stones. The medicinal properties of B. ligulata have been attributed to bergenin, its most potent bioactive component. Apart from bergenin, the other compounds available in B. ligulata are arbutin, gallic acid, protocatechuic acid, chlorogenic acid, syringic acid, catechin, ferulic acid, afzelechin, paashaanolactone, caryophyllene, 1,8-cineole, β-eudesmol, stigmasterol, β-sitosterol, parasorbic acid, 3-methyl-2-buten-1-ol, phytol, terpinen-4-ol, tannic acid, isovalaric acid, avicularin, quercetin, reynoutrin, and sitoinoside I. This review summarizes various medicinal properties of the herb, along with providing deep insight into its bioactive molecules and their potential roles in the amelioration of human ailments. Additionally, the possible mechanism(s) of action of the herb's anti-urolithiatic, antioxidative, antipyretic, anti-diabetic, anti-inflammatory and hepatoprotective properties are discussed. This comprehensive documentation will help researchers to better understand the medicinal uses of the herb. Further studies on B. ligulata can lead to the discovery of new drug(s) and therapeutics for various ailments.
... Nevertheless, even though, among the materials, that are concede to this class, it is mostly found that, in a proper status, plants components may have good effects. For example the ability of anti-carcinogenic properties of phyto-oestroneges (Migas & Krauze-Baranowska, 2015) and glucosinolates (Nugon-Baudon & Rabot, 1994), the anti-oxidative and anti-atherogenic effects of disuphide and allyl thiosulphinate and the potential coccidiostatic action of artmisin (Allen et al., 1999). While these possibly useful effects have reported mostly with health of human, it is possible, that some of components will be of worth in animal diet such as fit. ...
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Article
Background: This study was carried out to assess the effects of enriched feed with Japanese Pepper Seeds (1 and
... Arbutin (hydroquinone-β-D-glucopyronoside) and its derivatives, such as 2,3-di-Ogalloylarbutin, are naturally occurring glucopyranosides found in many plant species. It is known to have antiparasitic characteristics that deter both fungal and herbivore attack, as well as antioxidant, anti-inflammatory, and antitumour properties in vitro and in vivo [49][50][51]. This compound offers control and protection against cell damage caused by oxidative injury stress [52] and cell viability restoration, a useful property for protection of the intestinal cell wall lining in growing chicks. ...
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Article
Myrothamnus flabellifolius (Welw.) is used in African traditional medicine for the treatment of depression and mental disorder, asthma, infectious diseases, respiratory, inflammation, epilepsy, heart, wound, backaches, diabetes, kidney ailments, hypertension, hemorrhoids, gingivitis, shingles, stroke, and skins conditions. The effectiveness of M. flabellifolius is due to the presence of several secondary metabolites that have demonstrated efficacy in other cell and animal models. These metabolites are key in cell regulation and function and have potential use in animal production due to antimicrobial and antioxidant properties, for an improvement in growth performance, feed quality and palatability, gut microbial environment, function, and animal health. The purpose of this review is to provide a detailed account on the potential use of M. flabellifolius in animal nutrition. Limitations towards the use of this plant in animal nutrition, including toxicity, economic, and financial issues are discussed. Finally, novel strategies and technologies, e.g., microencapsulation, microbial fermentation, and essential oil extraction, used to unlock and improve nutrient bioaccessibility and bioavailability are clearly discussed towards the potential use of M. flabellifolius as a phytogenic additive in animal diets.
... The main mode of action for arbutin is inhibit the synthesis of melanin by acting as a tyrosinase inhibitor [70]. Besides, it is also Amer and Metwalli [51] Results: Patients with melasma, post-inflammatory hyperpigmentation, and freckles was achieved in good to excellent responses at 89.5%, 75%, and 44.4% respectively Side effects: Local irritation was found in most patients Ennes et al. [52] Results: 38% of patients showed total improvement, partial improvement in 57% and 5% of patients discontinued therapy Side effects: 28 possesses anti-inflammatory and antioxidant properties [71]. It is highly hydrophilic and hygroscopic due to its chemical structure which contains multiple hydroxyl groups. ...
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Article
Hyperpigmentation is a common and major skin problem that affects people of all skin types. Despite the availability of various depigmentation active ingredients for skin hyperpigmentation disorder, none of them are completely satisfactory due to their poor permeability through the skin layer and significant toxicity, thereby causing severe side effects such as irritative dermatitis, erythema, itching, and skin flaking. Nanotechnology plays an important role in advancing the cosmeceutical formulation by improving the solubility, stability, safety, loading efficiency, and dermal permeability of the active ingredients. The aim of this review is to offer a comprehensive discussion on the application of various nanomaterials in improving cosmeceutical formulations used to treat hyperpigmentation. Focus is placed on elucidating the advantages that nanotechnology can bring to some common hyperpigmentation active ingredients such as hydroquinone, arbutin, kojic acid, azelaic acid, and retinoic acid to improve their efficacy in treating hyperpigmentation. Lastly, a total of 44 reported patents and articles of depigmenting compounds encapsulated by nanoparticles were filed and analyzed. Overall, lipid nanoparticles were found to be the most widely used nanomaterial in treating hyperpigmentation. Graphical abstract
... It is a key enzyme involved in melanin synthesis and is widely used as a skin lightening agent for cosmetic products. 48 In another study, ARB showed weak but long-lasting radical scavenging activity and at the same time showing exactly the same antioxidant activity as hydroquinone; ...
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Background: In the presented study; the Effects of Arbutin (ARB) on the Rat Erythrocyte and serum fatty acid profile which is exposed to potassium bromate (KBrO 3) were investigated. Materials and Methods: In this study, 32 Wistar albino rats weighing 250-300 g were used divided into 4 groups. Groups 1: control, group 2: KBrO 3 (single dose 100 mg / kg gavage), group 3: ARB (50 mg / kg / day (ip) for 5 days), group 4: KBrO 3 + ARB. At the end of the 5 th day, alteration of fatty acid profile in erythrocyte and serum of rats in all groups was examined. Results: Rat serum essential fatty acid; palmitic acid (C16:0), myristic acid (C14:0), stearic acid (C18:0), oleic acid (C18:1), linoleic acid (C18:2), erythrocyte major fatty acids; palmitic acid (C16:0), myristic acid (C14:0), stearic acid (C18:0), oleic acid (C18:1), linoleic acid (C18:2), arachidic acid (C20:0), eicosenoic acid (C20:1), and lignoceric acid (C24:0). In addition, in our studied serum and erythrocytes; Total monounsaturated fatty acids (MUFA) varied between 8.91 ± 0.53-11.71 ± 2.55 and 33.71 ± 2.12-37.11 ± 2.12, respectively. It was determined that total polyunsaturated fatty acids (PUFA) varied between 5.90 ± 1.29-9.96 ± 1.18 and 14.72 ± 3.66-22.13 ± 4.82, respectively. Conclusion: In our study, alterations in fatty acid contents were observed, and results suggesting that arbutine affects the enzymes involved in Fatty acid metabolism and has an effect on fatty acid amounts.
... The primary natural source of β-arbutin is bearberry leaves (Arctostaphylos uvaursi) (Asensio et al., 2020). It is also found in pears (Cui et al., 2005), wheat, coffee, and tea (Migas & Krauze-Baranowska, 2015) (Figure 1). Although β-arbutin is widely available in plants, its extraction from plants is hindered by its low content, the complicated extraction process, and low purity of the extracted product. ...
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Article
Arbutin is a hydroquinone glucoside and a natural product present in various plants. Arbutin potently inhibits melanin formation. This property has been exploited in whitening cosmetics and pharmaceuticals. Arbutin production relies mainly on chemical synthesis. The multi-step and complicated process can compromise product purity. With the increasing awareness of sustainable development, the current research direction prioritizes environment-friendly, biobased arbutin production. In this review, current strategies for arbutin production are critically reviewed, with a focus on plant extraction, chemical synthesis, biotransformation, and microbial fermentation. Furthermore, the bottlenecks and perspectives for future direction on arbutin biosynthesis are discussed.
... Arbutin, a hydroquinone glucoside hydroquinone, is a natural active substance extracted from different plants [7][8][9]. It has certain specific physiological functions and exists widely in animal, plant and microbial cells [10]. ere are few reports on the effect of sepsis pneumonia. ...
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The aim of this study was to investigate the effects of arbutin (AR) on lipopolysaccharide (LPS)-induced sepsis pneumonia. LPS-induced mice and A549 cells were used to establish septic pneumonia model. AR significantly decreased lung wet-to-dry weight (W/D) ratio, lung myeloperoxidase (MPO) activity and ameliorated lung histopathological changes. In addition, AR increased super oxide dismutase (SOD) activity, decreased malondialdehyde (MDA) content and levels of cytokines including tumor necrosis factor-α (TNF-α), interleukin-1β (IL-β) and interleukin-6 (IL-6) in bronchoalveolar lavage fluid (BALF) in mice. Furthermore, the results demonstrated that AR inhibited the JAK2/STAT3/NF-κB pathway in LPS-induced A549 cells which was further confirmed by siRNA JAK2 experiment. The experimental results indicated that the protective mechanism of AR on sepsis pneumonia might be attributed partly to the inhibition of cytokine production and JAK2/STAT3/NF-κB pathway.
... Besides, radioprotective effects of arbutin have been reported in the literature [25]. Arbutin suppressed the activity of 5,6-dihydroksyindole-2-carboxylic acid polymerase and inhibited oxidative polymerization of melanogenic intermediates, being the mechanism anti-oxidant agents use to protect cells from free radicals induced by UV-radiation [27]. It has been reported that radioprotective agents act through various mechanisms, including free radical elimination, hypoxia induction, stimulation, and proliferation of hematopoietic and immunopoietic stem cells [28]. ...
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Purpose Efforts to produce radioprotective agents of high potentials are appropriate strategies for overcoming possible IR toxicity in organisms. The present research aims to evaluate the signaling pathways and mechanisms through which arbutin exerts radioprotective effects on organisms. Methods The databases of PubMed, Web of Sciences, Google Scholar, and Scopus were searched to find studies that reported radioprotective effects for arbutin. Besides, the data were searched within the time period from 2010 to 2020. Result Five research articles met our criteria, which were included in the analysis based on their relevance to the topic. The present systematic review provides conclusions about various mechanisms and pathways through which arbutin induces radioprotection. Conclusions Based on the relevant studies, various mechanisms can be proposed for inducing radioprotective effects by arbutin, including inhibition of oxidative stress, apoptosis, and inflammation.
... Due to the abundance of arbutin and its conjugates, lingonberry raw materials especially leaves act as antiseptics on the urinary tract (Jurica et al., 2015). However, the ability to act against common UTIs bacteria is affected mainly by the activity of deglycosylated product-hydroquinone (Migas and Krauze-Baranowska, 2015). One of the strongest (p < 0.05) inhibitory effects against S. typhimurium (i.z. ...
Article
Ethnopharmacological relevance Vaccinium vitis-idaea L. (lingonberry) leaves and fruits have traditionally been used in Asian and European countries as a natural solution for urinary tract infections, gastrointestinal distress, neurodegenerative diseases, and related inflammatory disorders, which are overall associated with free radical damage and presence of triggering pathogenic strains in the human body. Considering growing attention to natural products, there are not enough scientific data to confirm predominant specialized metabolites, responsible for the traditional therapeutic use of lingonberries. Aim of the study: The present study aimed at an in-depth study of specialized metabolite profiling and biological activity evaluation of lingonberry crude extracts and isolated fractions. Materials and methods Crude dry extracts and fractions from lingonberry leaves and fruits were analyzed by the UPLC-MS method. Potential inhibiting properties against different bacterial strains and hyaluronidase, ability to scavenge hydrogen peroxide, and effect on its production in a macrophage culture J774 were examined. Results Findings suggested the tentative presence of 59 compounds, mainly phenolics, displayed higher bioactivities of particular fractions than that of crude extracts and elucidated particular compounds as candidates in pharmaceuticals. Trimeric and dimeric proanthocyanidins from lingonberry leaves and fruits were shown to have the strongest antimicrobial, antioxidant, and anti-inflammatory potential. Conclusions This study revealed specialized metabolites responsible for the traditional medicinal properties of lingonberries and pointed out demand for further purification and new research directions of proanthocyanidins in the frame of their multipharmacological perspectives.
... The fourth natural compound was STOCK1N-07141 (arbutin), which was first discovered in the leaves of the bearberry plant and is widely found in animals, plants, and microbes [43,44]. Arbutin has been shown to have antioxidant, anti-inflammatory, and antibacterial properties [45][46][47]. Hydroxymethyl in STOCK1N-07141 formed an OH-O interaction with the oxygen from carboxyl in Asp30 with a distance of 2.4 Å and formed an O-HN interaction with the -NH from Asn33 with a distance of 1.9 Å. The two OH in STOCK1N-07141 formed an O-HN interaction with the -NH from Arg393 with a distance of 2.0 Å and formed an OH-O interaction with the oxygen from carboxyl in Glu37 with a distance of 1.7 Å. ...
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The angiotensin-converting enzyme II (ACE2) is a multifunctional protein in both health and disease conditions, which serves as a counterregulatory component of RAS function in a cardioprotective role. ACE2 modulation may also have relevance to ovarian cancer, diabetes, acute lung injury, fibrotic diseases, etc. Furthermore, since the outbreak of the coronavirus disease in 2019 (COVID-19), ACE2 has been recognized as the host receptor of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). The receptor binding domain of the SARS-CoV-2 S-protein has a strong interaction with ACE2, so ACE2 may be a potent drug target to prevent the virus from invading host cells for anti-COVID-19 drug discovery. In this study, structure- and property-based virtual screening methods were combined to filter natural product databases from ChemDiv, TargetMol, and InterBioScreen to find potential ACE2 inhibitors. The binding affinity between protein and ligands was predicted using both Glide SP and XP scoring functions and the MM-GBSA method. ADME properties were also calculated to evaluate chemical drug-likeness. Then, molecular dynamics (MD) simulations were performed to further explore the binding modes between the highest-potential compounds and ACE2. Results showed that the compounds 154-23-4 and STOCK1N-07141 possess potential ACE2 inhibition activities and deserve further study.
... Only a few compounds are currently used for clinical purposes as skin-whitening agents. Arbutin, characterized by its wide distribution in the Ericaceae and Caprifoliaceae families, exhibits anti-melanogenic activity in vitro and in vivo and can be useful in hyperpigmentation therapy [24]. The aqueous extract of Arbutus andrachne L. (Ericaceae) is used topically as skin lightener in some areas of Jordan. ...
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Secondary metabolites derived from hydroquinone are quite rare in nature despite the original simplicity of its structure, especially when compared to other derivatives with which it shares biosynthetic pathways. However, its presence in a prenylated form is somewhat relevant, especially in the marine environment, where it is found in different algae and invertebrates. Sometimes, more complex molecules have also been identified, as in the case of polycyclic diterpenes, such as those possessing an abietane skeleton. In every case, the presence of the dihydroxy group in the para position gives them antioxidant capacity, through its transformation into para-quinones.This review focuses on natural hydroquinones with antioxidant properties referenced in the last fifteen years. This activity, which has been generally demonstrated in vitro, should lead to relevant pharmacological properties, through its interaction with enzymes, transcription factors and other proteins, which may be particularly relevant for the prevention of degenerative diseases of the central nervous system, or also in cancer and metabolic or immune diseases. As a conclusion, this review has updated the pharmacological potential of hydroquinone derivatives, despite the fact that only a small number of molecules are known as active principles in established medicinal plants. The highlights of the present review are as follows: (a) sesquiterpenoid zonarol and analogs, whose activity is based on the stimulation of the Nrf2/ARE pathway, have a neuroprotective effect; (b) the research on pestalotioquinol and analogs (aromatic ene-ynes) in the pharmacology of atherosclerosis is of great value, due to their agonistic interaction with LXRα; and (c) prenylhydroquinones with a selective effect on tyrosine nitration or protein carbonylation may be of interest in the control of post-translational protein modifications, which usually appear in chronic inflammatory diseases.
... Furthermore, trans-ferulic acid ameliorates antioxidant enzyme levels [83]. Arbutin and apigenin were multifunctional molecules used in phytotherapy and phytocosmetics [84]. ...
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This study aims to examine the ability of apple vinegar on phenylhydrazine (PHZ)-induced hemolytic anemia in Wistar rats. In vitro, phenolic and flavonoid content and antioxidant activity were determined. In vivo, phenylhydrazine (10 mg/kg) was injected intravenously into rats for 4 days and then treated with apple vinegar daily by gavage (1 mL/kg) for five weeks. high level of polyphenols and flavonoids (90 ± 1.66 mg GAE/100 mL and 7.29 ± 0.23 mg QE/100 mL, respectively) were found in the apple vinegar which gives it a good ability to scavenge free radicals (TAC = 4.22 ± 0.18 mg AAE/100 mL and DPPH, IC50= 0.49 ± 0.004 µL/mL). The phytochemical composition of apple vinegar revealed the presence of numerous bioactive compounds including arbutin, apig-enin, sinapic, ferulic and trans-ferulic acids. The major antioxidant components in apple vinegar were ferulic and trans-ferulic acids (40% and 43%, respectively). PHZ treatment induced changes in platelets, blood cell count, mean corpuscular volume, hemoglobin concentration and mean capsu-lated hemoglobin. However, the co-administration of apple vinegar revealed its capacity to ameliorate the changes induced by phenylhydrazine. Therefore, apple vinegar use could have a positive impact on the prevention of hemolytic anemia induced by phenylhydrazine due to the antioxidant properties of its major components.
... Its young leaves and flower buds have been traditionally processed as herbal tea beverage, which was locally named as "Que Zui Tea" in the "Yi" minority areas of China . Long-term consumption of Que Zui Tea has health effects on the treatment or prevention of rheumatoid arthritis, diabetes, hyperlipidemia, and depression-like symptoms (Migas & Krauze-Baranowska, 2015;Xu, Liang, Zhang, & Zhao, 2015). V. dunalianum presented a series of phenolic acids, flavonoids and arbutin derivatives, and has been reported many pharmacological effects, such as antioxidant, anti-inflammatory, antidiabetic, and hepaprotective effects. ...
Article
Vaccinium dunalianum Wight is an important healthy tea resource in China with health benefits. The chemical compositions and the possible bioactive substances in its fruits, leaves and flower buds extracts (FE, LE and FBE) were identified and characterized by UHPLC-HRMS/MS. Consequently, FE, LE and FBE were rich in phenolic and flavonoid compounds. Among them, 21 compounds were identified, and the main components were chlorogenic acid, quinic acid and 6′-O-caffeoylarbutin. Furthermore, their neuroprotection and mechanism on H2O2-induced neurotoxicity in PC12 cells were investigated. All the different concentrations of FE, LE and FBE were apparently inhibited the H2O2-induced ROS generation and apoptosis on PC12 cells. FBE showed stronger neuroprotective activity against H2O2-induced PC12 cell damage than those of FE and LE. The mechanism of neuroprotective effect might be related to the upregulation of endogenous antioxidant enzymes expressions and activation of the Nrf2/HO-1 signaling pathway
... And all this time, arbutin has been applied to possess anti-inflammatory, anti-apoptosis, antimicrobial, and antioxidant effects. Even today, arbutin has also been used for the treatment of asthma (Migas and Krauze-Baranowska, 2015;Ortiz-Ruiz et al., 2015;Tang and Chen, 2015). Due to its mildly therapeutic properties, arbutin is also widely used in food, health-care, and cosmetic industries. ...
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Cholestasis is a kind of stressful syndrome along with liver toxicity, which has been demonstrated to be related to fibrosis, cirrhosis, even cholangiocellular or hepatocellular carcinomas. Cholestasis usually caused by the dysregulated metabolism of bile acids that possess high cellular toxicity and synthesized by cholesterol in the liver to undergo enterohepatic circulation. In cholestasis, the accumulation of bile acids in the liver causes biliary and hepatocyte injury, oxidative stress, and inflammation. The farnesoid X receptor (FXR) is regarded as a bile acid–activated receptor that regulates a network of genes involved in bile acid metabolism, providing a new therapeutic target to treat cholestatic diseases. Arbutin is a glycosylated hydroquinone isolated from medicinal plants in the genus Arctostaphylos , which has a variety of potentially pharmacological properties, such as anti-inflammatory, antihyperlipidemic, antiviral, antihyperglycemic, and antioxidant activity. However, the mechanistic contributions of arbutin to alleviate liver injury of cholestasis, especially its role on bile acid homeostasis via nuclear receptors, have not been fully elucidated. In this study, we demonstrate that arbutin has a protective effect on α -naphthylisothiocyanate–induced cholestasis via upregulation of the levels of FXR and downstream enzymes associated with bile acid homeostasis such as Bsep, Ntcp, and Sult2a1, as well as Ugt1a1. Furthermore, the regulation of these functional proteins related to bile acid homeostasis by arbutin could be alleviated by FXR silencing in L-02 cells. In conclusion, a protective effect could be supported by arbutin to alleviate ANIT-induced cholestatic liver toxicity, which was partly through the FXR pathway, suggesting arbutin may be a potential chemical molecule for the cholestatic disease.
... Arbutin, a tyrosinase inhibitor, etc. is widely marketed. (Migas and Krauze-Baranowska, 2015). However, arbutin derivatives are generally cytotoxic, limiting their application to some range (Rainforest et al., 2019). ...
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In this research, we sought to surmount the poor dissolvability and transdermal absorption rate of licorice flavonoids (LFs) by fabricating a LFs microemulsion. LFs content was determined using high performance liquid chromatography. Initial studies such as dissolution testing, emulsification testing, and pseudo ternary phase diagram generation were implemented for screening components and optimized adopting the central composite design. While the tested responses were solubility, droplet size and PDI, thirteen trials were performed using two different variables, oil percentage and optimized emulsifier and co-emulsifier ratio. Microemulsions were then characterized for droplet size, PDI, transmission electron microscopy, viscosity, electrical conductivity, pH, entrapment efficiency, drug content and stability. Additionally, skin release profile, percutaneous absorption and retention were investigated adopting Franz diffusion cell. The optimal formulation was found to compose of laureth-9 (emulsifier, 6.72 g), propylene glycol (co-emulsifier, 1.80 g), isopropyl myristate (IPM, oil, 1.48 g), LFs (1.50 g) and at least more than 85% deionized water. The optimized and storage for 3 months of microemulsion was found to clear, light yellow color without phase separation or precipitation indicated the stability of the preparation to long-term placement. The mean droplet size, PDI, entrapment efficiency and drug content were discovered as 12.68 ± 0.12 nm, 0.049 ± 0.005, 97.28 ± 0.13% and 122.67 ± 0.40 mg·g ⁻¹ , respectively. Furthermore, the optimal formulation sustained release LFs, remarkably deliver more LFs through the skin layer (644.95 ± 6.73 μg cm ⁻² ) and significantly retained LFs in the skin layer (9.98 μg cm ⁻² ). The study concluded that optimized microemulsion has potential and enhanced the dissolvability and cumulative penetration amount of LFs.
... Arbutin, well-known for diuretic, antiseptic properties [42], was the prevailing compound in the phenolic profiles, contributing 46-68% of identified phenolics in all tested lingonberry leaf samples (CV = 17%) with the highest (p < 0.05) content determined in a sample collected from Jurgionys forest and 2.4-fold lower level in Pažemys sample ( Figure 5). Arbutin-related compounds varied significantly (CV = 41%) among samples from different collecting locations, with predominance in samples from Galvokai, Kernai, and Jurgionys. ...
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Article
Lingonberry leaves have been proposed as a potential raw material for nutraceutical products and functional food due to the richness of phenolic and triterpenic compounds. However, contents of these bioactive compounds tend to vary greatly with physiological, climatic, and edaphic conditions, resulting in lingonberry leaves’ nutritional-pharmaceutical quality changes. In this context, we examined the effects of seasonal and geographical factors on phenolic and triterpenoid contents in lingonberry leaves. Quantitative and qualitative differences between samples were determined using validated HPLC-PDA methods. A total of 43 bioactive compounds were found at a detectable level throughout the year in young and old lingonberry leaves, with the highest contents of most compounds observed in samples collected in autumn–first half of spring. This suggests the potential to exploit the continuous biosynthesis for a longer harvesting season. Considerable variations in phytochemical profiles of lingonberry leaves, obtained from 28 locations in Lithuania, were found. Correlation analyses revealed significant negative correlations between contents of particular constituents and sunshine duration, temperature, and precipitation, and positive correlation with air humidity, longitudes, and altitudes of collecting locations and macronutrients in soil. These results suggest that harsh weather is favorable for most identified compounds and it may be possible to achieve appropriate accumulation of secondary metabolites by adjusting edaphic conditions. Taken together, the accumulation of phenolics and triterpenoids in lingonberry leaves highly depends on phenological and geographical factors and the influence of both variables differ for the particular compounds due to different metabolic processes in response to stresses.
... It normalized skin barriers with decreased production of IgE in mice serum. In addition, some studies showed that arbutin of different pear parts exhibited antiinflammatory effects on pro-inflammatory cytokines, such as IL-1β, TNF-α, and MCP-1 [9,89]. These proinflammatory cytokines attribute the cytokine storm of COVID-19. ...
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Background Pears have been world-widely used as a sweet and nutritious food and a folk medicine for more than two millennia. Methods We conducted a review from ancient literatures to current reports to extract evidence-based functions of pears. Results We found that pears have many active compounds, e.g., flavonoids, triterpenoids, and phenolic acids including arbutin, chlorogenic acid, malaxinic acid, etc. Most of researchers agree that the beneficial compounds are concentrated in the peels. From various in vitro , in vivo , and human studies, the medicinal functions of pears can be summarized as anti-diabetic,-obese, −hyperlipidemic, −inflammatory, −mutagenic, and -carcinogenic effects, detoxification of xenobiotics, respiratory and cardio-protective effects, and skin whitening effects. Therefore, pears seem to be even effective for prevention from Covid-19 or PM 2.5 among high susceptible people with multiple underlying diseases. Conclusion For the current or post Covid-19 era, pears have potential for functional food or medicine for both of communicable and non-communicable disease.
... Regarding kojic acid, skin irritation and allergic dermatitis were developed after using skincare products containing it 85 . In relation to arbutin, the application of higher concentrations caused skin irritation and hyperpigmentation 86 . Additionally, they have high toxicity, low stability, poor skin penetration, and insufficient activity 87 . ...
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Article
As the largest organ in human body, skin acts as a physicochemical barrier, offering protection against harmful environmental stressors, such as chemicals, pathogens, temperature and radiation. Nonetheless, skins prominence goes further, with a significant psychosocial role in an increasingly ageing population. Prompted by consumers’ concern regarding skincare, cosmetic industry has been developing new formulas capable of lessening the most visible signs of ageing, including reduction in skin density and elasticity, wrinkling and hyperpigmentation. Allied to skincare is the rising importance set on natural products, sustainably obtained from less environmental impacting methods. Cyanobacteria and microalgae are adding importance in this field, given their ability to biosynthesize secondary metabolites with anti-ageing potential. In this review, we present an overview on the potential of cyanobacteria and microalgae compounds to overcome skin-ageing, essentially by exploring their effects on the metalloproteinases collagenase, elastase, gelatinase and hyaluronidase, and in other enzymes involved in the pigmentation process.
... In this study, the APC-treated cells were not just compared to untreated cells, but also to arbutin, the positive control. Arbutin is a D-glucopyranoside derivative of hydroquinone, which is a widely used skin lightning agent in cosmetic and healthcare industry [43,44]. Our microarray data revealed that Nfkbia, which is involved in nuclear factor kappa B (NF-κB) binding, and cytoplasmic sequestering were down-regulated by arbutin. ...
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The beneficial effect on health of argan oil is recognized worldwide. We have previously reported that the cake that remains after argan oil extraction (argan press-cake or APC) inhibits melanogenesis in B16 melanoma cells in a time-dependent manner without cytotoxicity. In this study, the global gene expression profile of B16 melanoma cells treated with APC extract was determined in order to gain an understanding of the possible mechanisms of action of APC. The results suggest that APC extract inhibits melanin biosynthesis by down-regulating microphthalmia-associated transcription factor (Mitf) and its downstream signaling pathway through JNK signaling activation, and the inhibition of Wnt/β-catenin and cAMP/PKA signaling pathways. APC extract also prevented the transport of melanosomes by down-regulating Rab27a expression. These results suggest that APC may be an important natural skin whitening product and pharmacological agent used for clinical treatment of pigmentary disorders.
... This has grabbed the scientific interest in alternative chemicals to treat hyperpigmentation disorders, i.e., melasma. Other examples are arbutin [78], aloesin [79], azelaic acid [80], kojic acid [81], etc. have frequently applied as skin whitening formulations. ...
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Article
Ligninolytic enzymes are potential candidates in whitening cosmetics because of their high melanin decolorization potential. Lignin peroxidase (LiP) owns a special place in dermatology and cosmetology industries among ligninolytic enzymes due to its comparatively high redox potential than other enzymes. The unpurified LiPs after fungal fermentation are commonly studied in cosmetics formulations due to difficulties in enzyme purification. The deconstruction potential of LiP could be attributed to the versatility of substrates, including both non-phenolic and phenolic compounds and xenobiotics. The exploration of ligninolytic enzymes for potential biotechnological applications has commonly been reported over the years. This review aimed to summarize the futuristic applications and current functionalities of ligninolytic enzymes in modern cosmetics formulations as a skin-lightening agent through melanin decolorization applications. Studies suggest high throughput applications of LiP in the cosmetic sector, where it has the potential to replace hydroquinone and other skin-lightening agents whose safety has resulted in controversies. Moreover, pigmentation disorders such as hyperpigmentation could be treated in a sustainable manner using such enzyme-based approaches. Graphic Abstract
... respectively, close to the known melanogenesis inhibitor, arbutin (4-hydroxyphenyl β-D-glucopyranoside; 26.21±0.58%), which has been used as an effective skin-whitening agent in the cosmetic industry [28]. However, their analogues 6-9 showed weaker inhibitory activities. ...
Article
A new hydrocinnamoyl glucoside, 1-O-(4-hydroxyhydrocinnamoyl)-β-D-glucopyranose (1), together with fifteen known glycosides, including two phenylethanoid glycosides (2–3), two cinnamoyl glycosides (4–5), six phenolic glycosides (6–11), one lignan glycoside (12) and four megastigmane glycosides (13–16) were isolated from a 95% EtOH extract of the Typhonium giganteum rhizomes. The sixteen glycosides were structurally characterized by NMR, HRESIMS, enzymatic hydrolysis and comparison with literature. Upon evaluating inhibitory activities of compounds 1–16 against mushroom tyrosinase at 25 μM, compounds 10 and 11 exhibited obvious inhibitory activities, with %inhibition values of 20.94±0.59%, 23.28±1.09%, respectively, with arbutin used as the positive control (26.21±0.58%).
... Chitosan nanoparticles have been used for entrapping α-arbutin and βarbutin. These 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 A c c e p t e d M a n u s c r i p t chitosan NPs entrapped α and βarbutin have been observed to show higher stability and greater bioavailability as compared to their free forms thus proving chitosan NPs a promising carrier for topical delivery in skin whitening formulations [123,124]. ...
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The field of nanotechnology is being greatly explored by cosmetic industries in order to improve the efficacy of cosmetic products. The increased use of nanomaterials in the field of cosmetics can have two sides as health-related benefits and detrimental effects. This review mainly seeks the pros and cons of the use of nanomaterials in cosmetics along with some examples of nanomaterials that are widely used in cosmetic industries along with different types of nanotechnology-based cosmetic products. The benefits of nanomaterials in cosmetic formulations are huge. Moreover the study regarding the toxic effects on the health also equally matters. This review gives a brief outline of the advantages as well as disadvantages of nanotechnology in cosmetics.
... Both of them exhibit different activities. Arbutin is a whitening agent and has anti-inflammatory properties, whereas coumarin is a fragrant substance (Lee and Kim, 2012;Migas and Miroslawa, 2015). A previous study found that Thanaka had many activities, such as antioxidant and tyrosinase inhibitory activity as well as anti-bacterial and anti-inflammatory properties (Wanthong et al., 2010). ...
Article
Thanaka powder is made from the stem bark of the Hesperethusa crenulata plant. Most Burmese women use it on the skin of the face as sun protection, a moisturizing agent and acne treatment. For a hygiene purpose, gamma radiation is currently used to control microorganisms and insect contamination in many products. In this experiment, the the effects of gamma radiation on the microbial numeration, total phenolic content, antioxidant activity, and chemical constituent alterations in Thanaka powder were investigated. Gamma irradiation was applied to powder samples at 5, 10, 15 and 20 kGy. The total bacterial count and total yeast and mold count were decreased with increasing irradiation dose. Gamma irradiation at a dose of 5 kGy was sufficient to reduce the microbial load in the powder to meet the standards of microbial quality for cosmetic products in Thailand. No significant change in the DPPH activity of the Thanaka powder was observed after irradiation. Additionally, the radiation process caused significant increases in total phenolic content, FRAP value and arbutin content. At a dose of 20 kGy, the total phenolic content, FRAP value and arbutin content were significantly higher than the non-irradiated Thanaka powder at 7.45, 9.59 and 16.04%, respectively.
... 77 This simple phenol glucoside can be extracted from plants and can also be biosynthesized especially by Ericaceae (silvan undershrub species) and Saxifragaceae family. 78 It is a famous tyrosinase inhibitor (inhibitory effect on the hydroxylation reaction of tyrosinase) that has an application in skin whitening. 79 Substituted arbutin derivatives such as 6-p-coumaryl, 6-cafferyl, and 6-p-hydroxybenzoyl arbutin have also been isolated from plants. ...
Chapter
Drug likeness is a qualitative conception applied in drug design for how “drug-like” an element is related to factors such as bioavailability and extensively incorporated into the initial phases of lead and drug discovery. It is projected from the molecular structure earlier that the substance is at least synthesized and tested. A traditional technique to estimate drug likeness is to verify compliance of Lipinski’s Rule of Five, which contains the amounts of hydrophilic groups, molecular weight, and hydrophobicity. Methods to recognize drug-like molecules are grounded on their capability to discriminate known drugs from nondrugs in the groups of compounds by associating with one or more of the succeeding extensively available drug databases. There are different databases to categorize drug-like molecules which are based on their capability to discriminate known drugs from nondrugs in the set of compounds and have different methods to assess the drug likeness. The concept of drug likeness has numerous applications in drug discovery.
... 77 This simple phenol glucoside can be extracted from plants and can also be biosynthesized especially by Ericaceae (silvan undershrub species) and Saxifragaceae family. 78 It is a famous tyrosinase inhibitor (inhibitory effect on the hydroxylation reaction of tyrosinase) that has an application in skin whitening. 79 Substituted arbutin derivatives such as 6-p-coumaryl, 6-cafferyl, and 6-p-hydroxybenzoyl arbutin have also been isolated from plants. ...
... 77 This simple phenol glucoside can be extracted from plants and can also be biosynthesized especially by Ericaceae (silvan undershrub species) and Saxifragaceae family. 78 It is a famous tyrosinase inhibitor (inhibitory effect on the hydroxylation reaction of tyrosinase) that has an application in skin whitening. 79 Substituted arbutin derivatives such as 6-p-coumaryl, 6-cafferyl, and 6-p-hydroxybenzoyl arbutin have also been isolated from plants. ...
Chapter
Molecular docking is a computational tool of the molecules of complexes molded by different interactions of molecules. The aim of molecular docking is to predict the 3D structure. Molecular docking shows a significant role in the coherent design of drugs. To achieve an optimized conformation for both the protein and ligand, and relative orientation amongst protein and ligand, several types of docking are used often such as rigid docking, flexible docking, and full flexible docking so that the free energy of the overall system is minimized. De-novo drug design is a process in which the 3D structure of receptor is used to design newer molecules. It involves structural determination of the lead target complexes and lead modifications using molecular modeling tools.
... subtilis CJ 151 and B. subtilis GJ 614) might be more adapted to the Cheonggukjang model system used in this study and thereby produced a larger amount of arbutin, compared to the other B. subtilis strains tested. Hydroquinone has been known to be the primary precursor of arbutin [12]. Although studies related to hydroquinone content in soybeans have not been found in literature, arbutin production in fermented soybeans was observed in the present study. ...
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Article
The production of arbutin, an effective tyrosinase inhibitor as well as an outstanding antioxidant, by 691 Bacillus strains isolated from soybean-based foods was tested to enhance the tyrosinase inhibitory activity of soybeans via fermentation with the strains. Among the strains tested, the 5 strains capable of significantly producing arbutin were identified as B. subtilis via 16S rRNA sequencing. When soybeans were fermented with each of the selected strains, the arbutin content was highest on day 1 of fermentation and decreased thereafter. However, the tyrosinase inhibitory activity of the fermented soybeans continuously increased as fermentation progressed, whereas the activity of non-inoculated soybeans was consistently low. The results indicate that arbutin enhances the tyrosinase inhibitory activity of soybeans in the early period of fermentation, while other substances besides arbutin contribute to the activity in the later period. Consequently, soybeans fermented with arbutin-producing B. subtilis strains could be considered as a natural source of cosmeceuticals and nutricosmetics used in skin lightening and may be of interest in the food industry because they contain well-known and powerful antioxidants such as arbutin and other substances.
... Arbutin is also found in common foods, including pears, wheat products, coffee and tea 3 , culinary herbs including marjoram and oregano 4 , and free hydroquinone also occurs in trace quantities in coffee, red wine, wheat cereals and broccoli 3 . Both hydroquinone and arbutin are used topically in the cosmetic industry for their ability to suppress melanin biosynthesis 5 (Figure 1). ...
Article
Aim: To quantify and assess adverse events reported in the literature from the oral ingestion by humans of Arctostaphylos uva-ursi, Turnera diffusa and Achillea millefolium. Method: A systematic literature search for human case reports and clinical trials reporting adverse events from the oral ingestion of A. uva-ursi, T. diffusa and A. millefolium was conducted. Case reports were evaluated for quality using the Quality of Case Reports of Adverse Events instrument, and for causality using the WHO-UMC instrument. Clinical trials were evaluated for adherence to the CONSORT Extensions for Herbal Medicinal Interventions and Harms. Results: Two case reports and 15 clinical trials were included for analysis. One case report and two clinical trials reported adverse events for A. millefolium, one case report and no clinical trials reported adverse events for A. uva-ursi, and no case reports and one clinical trial reported adverse events for T. diffusa. Quality and causality assessment of case reports varied, and low adherence to CONSORT Extensions for Herbal Medicinal Interventions and Harms was observed in clinical trials. Conclusion: There appears to be very limited evidence of harm in humans from the oral ingestion of A. uva-ursi, A. millefolium and T. diffusa. The quality of reporting of both case reports and clinical trials involving herbal medicines needs to be improved to better understand the complex issue of herbal safety.
Article
Ethnopharmacological relevance Morus alba L. has long been used for beauty in many Asian countries and regions, including anti-aging and hyperpigmentation. Aim of the study This study aimed at the inhibitory effect of Morus alba L. root on melanogenesis in B16F10 melanoma cells and the mechanism involved. Materials and methods This study evaluated the anti-melanogenic effect of Morus alba L. root extract (MAR) on B16F10 melanoma cells by assessing cell viability, melanin accumulation, cellular tyrosinase activity, intra/inter-cellular S1P levels, cellular S1P-related metabolic enzyme activity, and western blot analysis. In addition, the potential S1P lyase (S1PL) inhibitory constituents in MAR were identified by LC-MS/MS. Results Without affecting the viability of B16F10 melanoma cells, MAR inhibited intracellular tyrosinase activity in a dose-dependent manner, thereby reducing the accumulation of melanin. MAR also downregulated the expression level of MITF via activating the ERK signaling pathway. Furthermore, MAR increased the intra/inter-cellular S1P by inhibiting S1PL. Several compounds with inhibitory S1PL activity have been identified in MAR, such as mulberroside A and oxyresveratrol. Conclusions The anti-melanogenic effects of MAR mainly involve promoting MITF degradation mediated via S1P–S1PR3-ERK signaling through increasing cellular S1P levels by inhibiting S1PL activity.
Article
The cactus pear fruit (Opuntia ficus-indica L. Mill.) is a product that has been recognized for the health benefits that it can provide, and it has also drawn scientific interest for several years. The objective of this study is to identify chemically the residues (Cakes oil) of Opuntia ficus indica l seed oil of eastern region of Morocco. A mechanical extraction is used to obtained this oil residues then we used maceration for the analysis extraction. Various phytochemical assays were used to determine the qualitative chemical composition, which was subsequently characterized using GC–MS and HPLC-DAD, LC-MS/MS. According to GC–MS analyses, which allow the identification of tree major fatty acids, (linoleic acid, oleic acid and palmitic acid), linoleic acid is abundant (37.218 %) for OFI seeds oil on the contrary, oleic acid is abundant (27.169 %) for OFI. HPLC-DAD analysis allows the identification of tocopherols, with the γ-tocopherols is the major tocopherol for with 310.01 ± 3.33 mg/Kg, the LC-MS/MS allow the identification of polyphenols and flavonoids, Among phenolic acids, residues of OFI was marked by the predominant of syringic acid (18.33 %), Arbutin (14.46 %), oleuropein (11.50 %) and p coumaric acid with (7.10 %).
Article
Melasma is acquired hyperpigmentation that mainly affects the face, can cause negative changes in self‐esteem, and mostly affects women. Treatment is difficult, and different drugs can be used in mono or combination therapy. In this article, we present a brief overview of melasma, how to evaluate it, and a synthesis of the most commonly used topical therapies and their indications, including sunscreens, pharmacological agents, and plant extracts. Hydroquinone (4%) in monotherapy or combined with corticosteroids (dexamethasone and fluocinolone acetonide) and retinoids (tretinoin); arbutin (1%); methimazole (5%); kojic (2%), azelaic (20%), and tranexamic (5%) acids are the pharmacological agents that stand out. Correct application of these substances determines a variable improvement in melasma but often causes adverse reactions such as erythema, itching, and burning at the application site. Vitamin C can contribute to the reduction of melasma and have little or no adverse effects while sunscreens are normally used as coadjuvant therapies. In conclusion, we have compiled specific topical therapies for treating melasma and discussed those that are the most used currently. We consider it important that prescribers and researchers evaluate the best cost–benefit ratio of topical therapeutic options and develop new formulations, enabling efficacy in the treatment with safety and comfort during application, through the reduction of adverse effects.
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Arbutin, the glucoside of hydroquinone, exists in two isomers, α-arbutin and β-arbutin. The synthetic α isomer is mainly used as a skin brightening agent, while β-arbutin occurs naturally, for instance in bearberry, and is used in drugs for treatment of lower urinary tract infections and as a food supplement. Since both isomers can be harmful at high concentrations, methods for their quantification are required. Classically they have been determined by reversed-phase chromatography, but separation of both isomers is often unsatisfactory. Here we present a simple and reliable method for quantification of α- and β-arbutin based on hydrophilic-interaction chromatography. Prior to analysis, interfering compounds that would frequently be present in cosmetics and drugs, particularly biopolymers, were efficiently removed by precipitation with acetonitrile. In this paper, for separation, a Cyclobond I 2000 5 µm 250 × 4.6 mm column was employed as stationary phase and acetonitrile/water 92/8 (v/v) was used as an eluent at a flow rate of 0.8 mL min−1. For quantification, a UV detector operating at 284 nm was applied. Although analysis took less than 10 min, baseline separation of α- and β-arbutin was achieved. The response was highly linear (r > 0.999) and the method had, for both α- and β-arbutin, a LOD of 0.003% (w/w) and a LOQ of 0.009% (w/w). Moreover, the method showed excellent intra-day and inter-day repeatability with relative standard deviations in the range of 0.5% to 2.3% and 1.0% to 2.2%, respectively, with cosmetics, drugs and food supplements as samples.
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The health benefits of non‐nutritive polyphenolic compounds present in plant sources and often constituting part of dietary intake, such as fruits, vegetables, cereals, and beverages (coffee/tea) have been well supported by several epidemiological studies, spanning over last few decades. Despite conflicting claims, the advancement beyond traditional understanding that health benefits originate from the antioxidant properties of these polyphenolics by the way of removing reactive oxygen species (ROS), has spurred renewed interest in the recent times. The varied pharmacological properties associated with these polyphenolics and their O‐glycosides from nature have inspired their use as valuable leads for further development and application as therapeutics. This perspective presents a brief overview of important dietary phenolics and their biological properties severing as a lead for ongoing research in their applications for health benefits.
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Natural products, remains the most important source for the discovery of new drugs for the treatment of human diseases. This has inspired the synthetic community to design and develop mimics of natural products either to answer important questions in biology or to explore their therapeutic potentials. Glycosides present themselves abundantly in nature, right from the cell surface receptors to natural products of any origin. The O-Glycosides are hydrolytically less stable compared to C-glycosides and this feature has presented a great opportunity for drug discovery. The discovery of Dapagliflozin, an SGLT inhibitor and C-glucoside, for the treatment of diabetes is one such example. Aryl acyl-anion chemistry has been explored for the synthesis of 2-deoxy-C-aryl furanoside/pyranoside/septanosides. Besides success, the studies have provided valuable insight into the natural propensities of the architectural framework for the cascade to furan derivatives. The aryl acyl-anion chemistry has also enabled the synthesis of biologically active diaryl heptanoids. Inspired from sucesss of Dapagliflozin, new analogues have been synthesized with pyridine and isocoumarin heterocycle as the proximal ring. C-glucosides of isoliquiritigenin have been synthesized for the first time and evaluated as an efficient aldose reductase inhibitor. The synthesis and evaluation of acyl-C-β-D-glucosides and benzyl-C-β-D-glucoside as glucose-uptake promoters has revealed promise in small molecules. The concept of building blocks has been used to obtain natural oxylipins, D-xylo and L-xylo-configured alkane tetrols and novel lipophilic ketones with erythro/threo configured trihydroxy polar head-group as possible anti-mycobacterial agents.
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Arbutin is a simple phenolic glucoside biosynthesised in many plant families. Some of the everyday foods that contain arbutin are species of the genus Origanum, peaches, cereal products, coffee and tea and Arctostaphyllos uva ursi L. leaves. Arbutin possesses various beneficial effects in the organism, and was confirmed effective in the treatment of urinary tract infections as well as in preventing skin hyperpigmentation. It shows antioxidant and anti-inflammatory properties, and antitumor activity. The aim of this study was to explore potential radioprotective properties of arbutin in concentrations of 11.4 μg/mL, 57 μg/mL, 200 μg/mL and 400 μg/mL administered as a pre-treatment for one hour before exposing human leukocytes to ionising radiation at a therapeutic dose of 2 Gy. The alkaline comet assay was used to establish the levels of primary DNA damage, and cytokinesis-block micronucleus (CBMN) cytome assay to determine the level of cytogenetic damage. None of the tested concentrations of single arbutin showed genotoxic and cytotoxic effects. Even at the lowest tested concentration, 11.4 μg/mL, arbutin demonstrated remarkable potential for radioprotection in vitro, observed both at the level of primary DNA damage, and using CBMN cytome assay. The best dose reduction compared with amifostine was observed after pre-treatment with the highest concentration of arbutin, corresponding to 400 μg/mL. Promising results obtained on the leukocyte model speak in favour of extending similar experiments on other cell and animal models.
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The pear quantity is not consistent with the quality of pear paste products due to different proportions of edible cane sugar (sucrose) added during food processing. To determine sucrose addition rate in pear paste, a mathematical model was established to quantify soluble solid concentration, sucrose-adding ratio and d-allose concentration. Gas chromatography-mass spectrometer (GC-MS) results showed that 18 compounds were detected in pear paste. When the total soluble solids (TSS) concentration of pear paste was constant, there was a negative linear relationship between d-allose content and the Ratio of Sucrose Added (RSA) (0.97 ≤R² ≤ 0.99)., Accordingly, the mathematical model of TSS-RSA-Allose concentration was fitted. It was found that the theoretical values of the pear paste at varied RSAs were comparable with the actual values under different conditions: 85% of the verified values differed by ≤ 10%. This study provides some reference for product testing departments to analyze products and establish the evaluation standard of sucrose ratioin pear paste.
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Molecularly imprinted polymers (MIPs) for glycosides, arbutin (ARB) and rutin (RUT), were prepared using methacrylamide (MAM) and 4-vinylpyridine (4-VPY) as functional monomers and divinylbenzene as a crosslinker by modified precipitation polymerization. The template molecule, ARB or RUT, was first dissolved in methanol, followed by precipitation polymerization using a mixture of acetonitrile and toluene as a porogenic solvent. The molar ratios of the template molecule, MAM and 4-VPY were optimized to achieve a high molecular recognition ability for ARB and RUT. The retention and molecular recognition properties of these MIPs were evaluated in HILIC or normal-phase mode. With an increase in the acetonitrile content in the mobile phase, the retention factor of ARB or RUT was increased. Furthermore, the MIPs for ARB and RUT showed the highest imprinting factors of 3.65 and 66.5 for the template molecules, respectively. Hydrogen bonding interactions such as N•••H-O, C = O•••H-O and NH•••O-H between 4-VPY or MAM and hydroxy groups of D-glucose or D-rutinose could function in the recognition of a glycone. Furthermore, hydrogen bonding interactions between functional monomers and the hydroxy group(s) of hydroquinone or quercetin could function in the recognition of an aglycone. These results suggest that the MIPs could recognize both a glycone and aglycone via hydrogen bonding interactions. Furthermore, MIPs for RUT were successfully applied to extract RUT in nutritional supplements.
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Background: Hydroquinone, arbutin and kojic acid are herbal-based skin whitening compounds that are used in many cosmetics. Today, the lack of side effects of arbutin and kojic acid has made them a valuable alternative to hydroquinone. Due to the toxic effects of whitening compounds, it is necessary to control the amount of use of these in the whitening products so that their concentration is within the permissible range. Objective: Therefore, the purpose of this study was to identify and quantify these three compounds in anti-lacquer products. In this research, the best separation of analytes has been tried by changing the HPLC mobile phase. Methods: Different samples were taken from the supply level. After extraction and preparation of samples, the solution was injected into HPLC-UV. In order to optimize the method, three different mobile phases were used to identify the compounds. By comparing the obtained peaks with the standard peaks, the Whitening compounds were identified and quantified. Results: The results showed that hydroquinone and kojic acid were applied in three products and arbutin in one product and the concentration of all the compounds used were within the standard range. Four out of the eight companies surveyed did not correctly identify the compounds used in their products. Conclusion: Reverse Phase HPLC-UV is also one of the best methods for determination and quantification the whitening compounds and water composition: acetonitrile with a ratio of 80:20 v/v is the most appropriate mobile phase in this method.
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Six undescribed compounds (1–6) were isolated from the leaves of Viburnum erosum along with four known compounds 7–10. The structures were determined by NMR and MS spectroscopic analyses, and their absolute configurations were established by chemical and spectroscopic methods. Compounds 1–6 were α-glucosidic hydroquinone derivatives with different linear monoterpenoid structures. Compounds 1–10 were also evaluated for their tyrosinase inhibitory activities, and 10 showed potent inhibition of tyrosinase enzyme with IC50 value of 37.9 μM compared to 47.6 μM of the positive control (β-arbutin).
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The tender leaves and buds of Vaccinium dunalianum Wight have been traditionally processed as folk tea, known as Que Zui tea (QT), with a wide range of benefits to humans. In this study, Que Zui tea hot-water extract (QTW) and aqueous-ethanol extract (QTE) were tested for their effectiveness to alleviate acetaminophen (APAP)-induced liver damage. QTW and QTE significantly inhibited the alanine aminotransaminase, aspartate aminotransaminase, tumor necrosis factor-α, interleukin-6, and interleukin-1β levels in the serum. Both extracts also ameliorated pathological damage and inhibited oxidative stress in the liver of APAP-induced mice. In addition, QTW and QTE activated the nuclear erythroid related factor 2 signal pathway, and inhibited mitogen-activated protein kinase activation. QTW and QTE also suppressed hepatocyte apoptosis by improvement of Bcl-2/Bax and inhibition of caspase-3 and caspase-9 expression. The results demonstrated that QTW and QTE could effectively protect APAP hepatotoxicity, which might be attributed to their antioxidant, anti-inflammatory and anti-apoptosis activities.
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A simple, fast method of high-performance liquid chromatography for the determination and quantification of arbutin and hydroquinone in many different raw materials was developed and validated. The optimum conditions for the separation and detection of these two constituents were achieved on a LiChro-CARD 125-4 Superspher®100 RP-18 column with the water-methanol (gradient elution) mobile phase and recorded at 289 nm. The purities of peaks were verified by PDA analysis of impurities. The results of validation have shown that the HPLC method is stable and accurate for the simultaneous determination of arbutin and hydroquinone in extracts from various plants. The developed method gave a good sensitivity (LOD 1μg/ml for arbutin and 0.49 μg/ml for hydroquinone) with linearity R2 >0.9993 (for both). The relative standard deviation of the method was less than 2.53% for intra-day assays and 3.23% for inter-day assay, the accuracy of the recovery test ranged from 98.96% to 106.4%. This method was used in comparative qualitative analysis of arbutin and hydroquinone in 16 different raw materials from families Lamiaceae, Ericacaeae, Saxifragaceae, Rosaceae. The content of arbutin in B. ciliata, B. cordifolia and Ledum palustre was examined for the first time.
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Urinary tract infection (UTI) is a common disease. Continued allopathic treatment with various antibiotics may cause side effects. It is also known that the bacteria causing infection can develop resistance to the existing antibiotics that have been prescribed, if the medication is used for a long time. These issues have led to a continuous exploration of different modes of treatment and alternate therapies. Herbs have a long history and proven to be very effective in preventing and treating urinary tract infections. This review article is about some commonly accepted herbs like Vaccinium macrocarpon [Cranberry], Hydrastis Canadensis [Goldenseal], Agathosma betulina [Buchu], Arctostaphylos uva-ursi [Bearberry], Echinaceae purpurea[Cone flower] and Equisetum arvense [Horse tail] that have been clinically proven for urinary tract infection cure as well as bladder infection treatment.
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Secondary metabolites are chemical found in plants. These have no role in plant growth but these are important for human because it have many pharmacological activity. Bergenia species such as Bergenia stracheyi, Bergenia ligulata And Bergenia ligulata etc. have many secondary metabolites such as 1. Bergenin 2. Tannic acid 3. Gallic acid 4. Stigmesterol 5. β-Sitosterol 6. catechin 7. (+)-Afzelechin 8. 1, 8-cineole 9. Isovalaric acid 10. (+)-(6S)-parasorbic acid 11. Arbutin 12. Phytol 13. Caryophyllene 14. Damascenone 15. β-eudesmol 16. 3-methyl-2-buten-1-ol 17. (Z)-asarone 18. Terpinen-4-ol 19. Paashaanolactone which are medicinally important.
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Arbutin (hydroquinone β-D-glucoside) is a compound of plant origin possessing valuable therapeutic (urinary tract disinfection) and cosmetic (skin whitening) properties, which can be obtained from in vitro cultures of plants belonging to different taxa via biotransformation of exogenously supplemented hydroquinone. Agitating cultures of Aronia melanocarpa were maintained on the Murashige and Skoog medium containing growth regulators: the cytokinin - BAP (6-benzylaminopurine), 2 mg/l and the auxin NAA (α-naphthaleneacetic acid), 2 mg/l. The biomass was cultured for 2 weeks and then hydroquinone was supplemented at the following doses: 96, 144, 192, 288 and 384 mg/l either undivided or divided into two or three portions added at 24-hour intervals. The content of the reaction product - arbutin, was determined using an HPLC method in methanolic extracts from biomass and lyophilized medium samples collected 24 hours after the addition of the last precursor dose. The total amounts of arbutin were very diverse, from 2.71 to 8.27 g/100g d.w. The production of arbutin rose with increasing hydroquinone concentration. The maximum content of the product was observed after hydroquinone addition at 384 mg/l divided into two portions. Biotransformation efficiency also varied widely, ranging from 37.04% do 73.80%. The identity of the product - arbutin, after its isolation and purification was confirmed by spectral analysis ((1)H-NMR spectrum). The maximum amount of arbutin obtained was higher than that required by the latest 9(th) Edition of the Polish Pharmacopoeia and by the newest 8th Edithion of European Pharmacopoeia for Uvae ursi folium (7.0 g/100g d.w.), and is interesting from practical point of view.
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Uva-ursi folium (bearberry leaf) has been traditionally used to treat symptoms of lower urinary tract infections. The most representative constituent of this herbal drug is arbutin that is rapidly absorbed in the small intestine and undergoes hepatic conjugation to form hydroquinone (HQ) conjugates. As free HQ is crucial for the safety of the herbal preparation, we reviewed published and unpublished experimental and human studies to clarify some outdated assumptions and to support the safety of therapeutic daily doses of Uva-ursi folium extract. Specifically, data on pharmacokinetics and the human exposure of arbutin and HQ were reviewed. A therapeutic recommended human daily dose of bearberry leaf extract (420 mg hydroquinone derivatives calculated as anhydrous arbutin) liberates free HQ in urine at a maximum exposure level of 11 µg/kg body weight (bw)/d. By means of an experimental no observed effect level value, a permitted daily exposure dose below which there is a negligible risk to human health was estimated for free HQ (100 µg/kg bw/d). Dietary sources of arbutin/HQ that are regularly consumed long term by humans generate comparable free HQ exposure levels. There is no direct evidence, regarding human data, supporting the fact that free HQ causes convulsion, hepatotoxicity, nephrotoxicity, or promotion of tumors in humans. Free HQ had no activity promoting pancreatic, bladder, stomach, or liver carcinogenesis. In conclusion, under the recommended use conditions Uva-ursi folium is a safe therapeutic option for treating lower urinary tract infections.
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Increased production and accumulation of melanin are characteristics of a large number of skin diseases, including melasma, post-inflammatory hyperpigmentation and lentigo. A number of clinical agents can reduce normal or abnormal pigmentation, but none of these have achieved satisfactory effects. This review discusses the mechanisms behind the different approaches. Tyrosinase is a pivotal enzyme in melanin synthesis. The majority of whitening or lightening agents act by specifically reducing the activity of tyrosinase via several mechanisms: (1) prior to melanin synthesis (interfering with its transcription and/or glycosylation); (2) during melanin synthesis (tyrosinase inhibition, peroxidase inhibition and reduction of byproducts); and (3) after melanin synthesis (tyrosinase degradation, inhibition of melanosome transfer, acceleration of skin turnover). Additional melanogenesis-associated mechanisms are also discussed.
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Abstract: Arbutin has antioxidative properties with potential benefits in many diseases. In this study, the cytoprotective and antioxidant effects of arbutin against t-BPH induced oxidative stress in Hep G2 cells were evaluated. HepG2 cells were cultured in 24-well plates (2.5×105 cells in 1 ml RPMI-1640 + 10% FBS+1% Pen. Strep). Arbutin at different concentrations (0, 50, 100 and 150 μM) were added into the wells. After 24 h exposure to arbutin, t-BHP at different concentrations (0, 100, 150, 200 and 250 μM) were added. Viability was measured (t = 72 h) using MTT assay and TB test. Furthermore, the antioxidant effect of arbutin was evaluated by FRAP assay. Arbutin significantly increased the total antioxidative power and antagonized the t-BHP oxidative effects. The cytotoxicity of t-BHP was significantly reduced by arbutin pretreatment. In the TB test and MTT assay, there was a significant difference between cell viability of group containing arbutin and t-BHP with group containing only t-BHP in a dose-dependent manner. Arbutin increased the total antioxidative power and it had cytoprotective effect. Increasing of cell viability might be an explanation to these effects. Key words: Arbutin % Antioxidant % Cell viability % HepG2 cell line % Tert-butyl hydroperoxid (t-BHP) % Oxidative stress
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Arbutin has been used as a whitening agent in cosmetic products. Melanin, the major pigment that gives color to skin, may be over-produced with sun exposure or in conditions such as melasma or hyperpigmentary diseases. Tyrosinase is a key enzyme that catalyzes melanin synthesis in melanocytes; therefore, inhibitors of the tyrosinase enzyme could be used for cosmetic skin whitening. A recent study has reported that arbutin decreases melanin biosynthesis through the inhibition of tyrosinase activity. However, this inhibitory mechanism of arbutin was not sufficiently demonstrated in skin tissue models. We found that arbutin both inhibits melanin production in B16 cells induced with α-MSH and decreases tyrosinase activity in a cell-free system. Furthermore, the hyperpigmentation effects of α-MSH were abrogated by the addition of arbutin to brownish guinea pig and human skin tissues. These results suggest that arbutin may be a useful agent for skin whitening.
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Melanin is produced in melanocytes and stored in melanosomes. In spite of its beneficial sun-protective effect, abnormal accumulation of melanin results in esthetic problems. Hydroquinone, competing with tyrosine, is a major ingredient in topical pharmacological agents. However, frequent adverse reactions are amongst its major limitation. To solve this problem, several alternatives such as arbutin, kojic acid, aloesin, and 4-n-butyl resorcinol have been developed. Herein, we classify hypopigmenting agents according to their mechanism of action; a) regulation of enzyme, which is subdivided into three categories, i) regulation of transcription and maturation of tyrosinase, ii) inhibition of tyrosinase activity, and iii) post-transcriptional control of tyrosinase; b) inhibition of melanosome transfer, and c) additional mechanisms such as regulation of the melanocyte environment and antioxidant agents.
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Arbutin is a glycosylated hydroquinone extracted from the bearberry plant (Arctostaphylos species). In the present study, we determined the effects of arbutin on TCCSUP human bladder carcinoma cell proliferation. Arbutin did not exhibit any cytotoxic effects in TCCSUP cells at concentrations of < 500 microg/ml. To determine the effects of arbutin on cell proliferation, TCCSUP cells were treated with arbutin at various concentrations, and the cell proliferation was measured using the MTT assay. Arbutin significantly decreased TCCSUP cell proliferation in a concentration- and time-dependent manner. Furthermore, cell cycle analysis revealed that arbutin strongly disrupted the cell cycle in a time-dependent manner. Western blot analysis demonstrated that arbutin led to the inactivation of extracellular signal-regulated kinase (ERK), which is known to critically regulate cell proliferation. In addition, arbutin markedly increased the expression of p21WAF1/CIP1 (p21), which is known to be highly involved in cell cycle regulation. Therefore, this study suggests that arbutin inhibits TCCSUP cell proliferation via ERK inactivation and p21 up-regulation.
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This work is part of a series of chemical investigations of the genus Grevillea. Two new arbutin derivatives, seven new bisresorcinols, including a mixture of two isomers, three known flavonol glycosides, and four known resorcinols, including a mixture of two homologous compounds, were isolated from the ethyl acetate extract of the leaves and methanol extract of the stems of Grevillea banksii. The new compounds were identified, on the basis of spectroscopic data, as 6′-O-(3-(2-(hydroxymethyl)acryloyloxy)-2- methylpropanoyl)arbutin (1), 6′-O-(2-methylacryloyl)arbutin (2), 5,5′-(4(Z)-dodecen-1,12-diyl)bisresorcinol (6), 2′-methyl-5, 5′-(4(Z)-tetradecen-1,14-diyl)bisresorcinol (8), 2,2′-di(4- hydroxyprenyl)-5,5′-(6(Z)-tetradecen-1,14-diyl)bisresorcinol (9), 2-(4-acetoxyprenyl)-2′-(4-hydroxyprenyl) 5,5′-(6(Z)-tetradecen-1,14- diyl)bisresorcinol (10), 2-(4-acetoxyprenyl)-2′-(4-hydroxyprenyl)5, 5′-(8(Z)-tetradecen-1,14-diyl)bisresorcinol (11), 5,5′-(10(Z)- tetradecen-1-ondiyl) bisresorcinol (12) and 5,5′-(4(Z)-tetradecen-1-on- diyl)bisresorcinol (13).
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Postinflammatory hyperpigmentation is a common sequelae of inflammatory dermatoses that tends to affect darker skinned patients with greater frequency and severity. Epidemiological studies show that dyschromias, including postinflammatory hyperpigmentation, are among the most common reasons darker racial/ethnic groups seek the care of a dermatologist. The treatment of postinflammatory hyperpigmentation should be started early to help hasten its resolution and begins with management of the initial inflammatory condition. First-line therapy typically consists of topical depigmenting agents in addition to photoprotection including a sunscreen. Topical tyrosinase inhibitors, such as hydroquinone, azelaic acid, kojic acid, arbutin, and certain licorice extracts, can effectively lighten areas of hypermelanosis. Other depigmenting agents include retinoids, mequinol, ascorbic acid, niacinamide, N-acetyl glucosamine, and soy with a number of emerging therapies on the horizon. Topical therapy is typically effective for epidermal postinflammatory hyperpigmentation; however, certain procedures, such as chemical peeling and laser therapy, may help treat recalcitrant hyperpigmentation. It is also important to use caution with all of the above treatments to prevent irritation and worsening of postinflammatory hyperpigmentation.
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A simple flow injection (FI) manifold with spectrophotometric detection was fabricated and tested for arbutin determination. It is based on the measurement of a red-coloured product at 514 nm formed by the complexation reaction between arbutin and 4-aminoantipyrine (4-AP) in the presence of hexacyanoferrate (III) in an alkaline medium. On injecting 300 μL standard solutions at various concentrations of arbutin into the FI system under optimum conditions, a linear calibration graph over the range of 1.0-30.0 μg mL-1 arbutin was established. It is expressed by the regression equation y = 0.2188 ± 0.0036x + 0.1019 ± 0.0366 (r2 = 0.9990, n = 5). The detection limit (3σ) and the limit of quantitation (10σ) were 0.04 μg mL-1 and 0.13 μg mL-1, respectively. The RSD of intraday and interday precisions were found to be 1.2-1.4% and 1.7-2.7%, respectively. The method was successfully applied in the determination of arbutin in four selected fruits and three commercial whitening cream extracts with the mean recoveries of the added arbutin over the range of 96.2-99.0%. No interference effects from some common excipients used in commercial whitening creams were observed. The method is simple, rapid, selective, accurate, reproducible and relatively inexpensive. © 2009 Society of Cosmetic Scientists and the Société Française de Cosmétologie.
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The kinetic behavior of the melanin biosynthesis pathway from L-tyrosine up to dopachrome has been studied from experimental and simulation assays. The reaction mechanism proposed is based on a single active site of tyrosinase. The diphenolase and monophenolase activities of tyrosinase involve one single (oxidase) and two overlapped (hydroxylase and oxidase) catalytic cycles, respectively. The stoichiometry of the pathway implies that one molecule of tyrosinase must accomplish two turnovers in the hydroxylase cycle for each one in the oxidase cycle. Furthermore, the steady-state rates of dopachrome production and O2 consumption from tyrosine and L-dopa, also fulfill the stoichiometry of the pathway: VO2T/VDCT = 1.5 and VO2T/VDCD = 1.0, where T represents L-tyrosine, DC represents dopachrome, and D represents L-dopa. It has been ascertained by high performance liquid chromatography that in the steady-state, a quantity of dopa is accumulated ([D]ss) which fulfills the constant ratio [D]ss = R[T]0. Taking this ratio into account, an analytical expression has been deduced for the monophenolase activity of tyrosinase. In this expression kcatT congruent to (2/3)k3(K1/K2)R, revealing that kcatT is not a true catalytic constant, since it also depends on equilibrium constants and on the experimental R = 0.057. This low value explains the lower catalytic efficiency of tyrosinase on tyrosine than on dopa, (VmaxT/KmT)/(VmaxD/KmD) congruent to (2/3)R, since a significant portion of tyrosinase is scavenged from the catalytic turnover as dead-end complex EmetT in the steady-state of the monophenolase activity of tyrosinase.
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High background levels of phenol and hydroquinone are present in the blood and urine of virtually all individuals, but vary widely. Phenol and hydroquinone have been strongly implicated in producing leukemia associated with benzene exposure, because they reproduce the hematotoxicity of benzene, cause DNA and chromosomal damage found in leukemia, inhibit topoisomerase II, and alter hematopoiesis and clonal selection. The widely varying background levels of phenol and hydroquinone in control individuals stem mainly from direct dietary ingestion, catabolism of tyrosine and other substrates by gut bacteria, ingestion of arbutin-containing foods, cigarette smoking, and the use of some over-the-counter medicines. We hypothesize that these background sources of phenol and hydroquinone and associated adducts play a causal role in producing some forms of de novo leukemia in the general population. This hypothesis is consistent with recent epidemiological findings associating leukemia with diets rich in meat and protein, the use of antibiotics (which change gastrointestinal flora make-up), lack of breastfeeding, and low activity of NAD(P)H quinone oxidoreductase which detoxifies quinones derived from phenol and hydroquinone and protects against benzene hematotoxicity. An attractive feature of our hypothesis is that it may explain why many people who have no known occupational exposures or significant smoking history develop leukemia. The hypothesis predicts that susceptibility to the disease would be related to diet, medicinal intake, genetics and gut-flora composition. The latter two of these are largely beyond our control, and thus dietary modification and reduced use of medicines that elevate phenol levels may be the best intervention strategies for lowering leukemia risk.
Chapter
Throughout history and cross-culturally, healers have employed procedures and medicinal substances to expel toxins, poisons, evil spirits, etc. from a sick patient's body. Purging, blood-letting, sweat induction and the use of natural laxatives, expectorants, and diuretics are all prominently featured in traditional medical systems. Diuretic herbs have been frequently prescribed to rid the body of excess fluids through increased urine production, as well as for detoxification and dehydration for such conditions as high blood pressure, kidney infections, obesity, and the edema associated with pre-menstrual syndrome (PMS) or traumatic injuries. A survey of 92 medicinal plant shops (“botanicas”) in Miami, Florida discovered 13 botanical species sold specifically for their diuretic effects. An additional 394 species used for this purpose worldwide were catalogued in the literature for a total of 407. These plants contain a number of phytochemical compounds that induce diuresis, including saponin (C27H42O3) and arbutin (C12H16O7). Research suggests that saponin ingestion is associated with reduced incidence of kidney stones, and arbutin has an anti-bacterial effect on the urinary tract. Many of the plants contain a number of flavonoids and polyphenols which also may impart therapeutic benefits for the renal system. The two main preparation methods of herbal medicines—decoction and infusion—permit the extraction and concentration of their curative bioactive constituents while simultaneously eliminating or neutralizing toxins, irritants and impurities. The most commonly utilized plant parts to produce traditional diuretic medications are leaves, stems, seeds, roots, berries, barks, saps, resins, pollens, and fruit juices. Many of the plants used as diuretics are also recommended by traditional healers for a variety of other health problems, including high and low blood pressure, dental disorders, and fertility-related applications. Rigorous double-blind/placebo trials are needed to verify the therapeutic value and safety of botanical diuretics.
Article
The presence of yet to be explored radical scavengers in the leaf extracts of Cnestis ferruginea (De Candolle) have been reported. Thus, the present study is focused on isolating and characterizing these radical scavengers for possible therapeutic use as lead drug candidates against oxidatively induced pathological conditions. The defatted methanol extracts (MECF) of the leaves of Cnestis ferruginea was fractionated into Chloroform (CF), Ethylacetate (EF), Butanol (BF) and Water (WF) fractions. Total antioxidant property, superoxide anion, l,l-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activities and inhibition of xanthine oxidase activity by the fractions were determined. The extent of inhibition of Fe 2+/ascorbate stimulated lipid peroxidation in mitochondrial membranes was also evaluated. All fractions and crude extracts exhibited antioxidant properties at different degrees. The pattern of DPPH radical scavenging activity and inhibition of mitochondrial membrane lipid peroxidation by MECF and EF were similar, β-sitosterol, para-hydroxyphenol and six other sub-fractions were isolated from EF. The DPPH radical scavenging activities of the sub-fractions were not significantly (p>0.05) different from one another. Robustaside B or 6'-(3", 4"-dihydroxycinnamoyl) arbutin was also isolated from sub-fraction III from EF using sephadex LH 20. Structural elucidation of all compounds was determined by spectroscopy (IR, UV, ID and 2D 1H and 13C NMR). The present study reported for the first time the isolation and radical scavenging activity of Robustaside B-an arbutin derivative and para-hydroxyphenol from leaves of Cnestis ferruginea. Leaf extracts of Cnestis ferruginea was demonstrated to be a rich source of antioxidants.
Article
Arbutus unedo leaf is used traditionally for gastrointestinal complaints. Ethanol extracts from Arbutus unedo collected in both Montenegro (AuM) and Greece (AuG) were found to decrease the ileal basal tonus, with AuG producing a significantly higher (p < 0.05) reduction in contractile response to acetylcholine. AuM and AuG relaxed 80 mM K(+) induced contractions and shifted the Ca(++) concentration-response curves to the right, similar to that caused by verapamil, suggesting that the spasmolytic effect was induced through calcium channel inhibition. The antioxidant activity of AuM and AuG and the phenolic content of the extracts and dry plant material were studied, and both extracts were found to possess considerable antioxidant properties. AuG showed a stronger in vitro antioxidative activity in the DPPH assay and in the TBA test. Polyphenol, tannin and flavonoid levels were higher in AuG, supporting the more potent spasmolytic and antioxidative effects, whereas the arbutin content was higher in dry plant material collected in Montenegro.
Article
From the 1-BuOH-soluble fraction of a MeOH extract of the leaves of Grevillea robusta, new arbutin derivatives and related compounds, named grevillosides J-Q (1-8), together with eight known compounds (9-18) were isolated. Various kind of acyl groups were attached to β-D-glucose at the 6-position through an ester linkage. Their structures were mainly elucidated from one- and two-dimensional NMR spectroscopic data. For exploitation as skin-lightening and anti-chloasma agents, the inhibitory activities of the isolated compounds as well as ones isolated in previous experiments (19-31) toward tyrosinase and melanin-producing B16 cells were assayed. Several compounds showed promising activity.
Article
This work is part of a series of chemical investigations of the genus Grevillea. Two new arbutin derivatives, seven new bisresorcinols, including a mixture of two isomers, three known flavonol glycosides, and four known resorcinols, including a mixture of two homologous compounds, were isolated from the ethyl acetate extract of the leaves and methanol extract of the stems of Grevillea banksii. The new compounds were identified, on the basis of spectroscopic data, as 6′-O-(3-(2-(hydroxymethyl)acryloyloxy)-2- methylpropanoyl)arbutin (1), 6′-O-(2-methylacryloyl)arbutin (2), 5,5′-(4(Z)-dodecen-1,12-diyl)bisresorcinol (6), 2′-methyl-5, 5′-(4(Z)-tetradecen-1,14-diyl)bisresorcinol (8), 2,2′-di(4- hydroxyprenyl)-5,5′-(6(Z)-tetradecen-1,14-diyl)bisresorcinol (9), 2-(4-acetoxyprenyl)-2′-(4-hydroxyprenyl) 5,5′-(6(Z)-tetradecen-1,14- diyl)bisresorcinol (10), 2-(4-acetoxyprenyl)-2′-(4-hydroxyprenyl)5, 5′-(8(Z)-tetradecen-1,14-diyl)bisresorcinol (11), 5,5′-(10(Z)- tetradecen-1-ondiyl) bisresorcinol (12) and 5,5′-(4(Z)-tetradecen-1-on- diyl)bisresorcinol (13).
Article
6′-0-[(2R)-methyl-3-veratroyloxy-propanoyl] arbutin [1] and 4′-0-[(2R)-methyl-3-veratroyloxy-propanoyl] arbutin [2], two new arbutin derivatives, have been isolated from the leaves of Gentiana pyrenaica. Their structures were determined by spectral and chemical means.
Article
Arbutin is a hydroquinone derivative that has been found in species of several plant families. Within the genus Origanum the formation of arbutin is polymorphic, with arbutin present in considerable amounts (O. dubium 20.8±15.3mg/g; wild O. majorana 51.3±15.4mg/g, cultivated O. majorana 40.6±11.2mg/g), minor amounts (O. microphyllum 0.1±0.1mg/g, wild O. onites 0.3±0.1mg/g, cultivated O. onites 0.1±0.1mg/g, O. saccatum 0.1±0.1mg/g, O. solymicum 0.4±1.0mg/g) or completely absent (O. husnucan-baseri, O. syriacum, O. vulgare). Whereas the most important commercial oregano species (O. onites and O. vulgare) contain no or only minor amounts of arbutin, marjoram (O. majorana) has considerably high amounts. The high variability of arbutin in O. majorana would allow a selection into cultivars with high arbutin content and low arbutin varieties. In a segregating F2-generation of a species crossing between O. majorana (high content of arbutin) and O. vulgare ssp. vulgare (free of arbutin), the presence of arbutin followed a Mendelian segregation of 3:1, indicating that only one gene is responsible for the polymorphism of arbutin in the genus Origanum. The absence of arbutin in O. vulgare ssp. vulgare or O. syriacum would even enable the breeding of marjoram with no arbutin at all.
Article
A mutant Xanthomonas maltophilia BT-112 with high α-anomer-selective glycosylation activity was screened by a series of mutation methods including UV light, N-methyl-N-nitro-N-nitroso-guanidine treatment and quick neutron mutation. The α-arbutin titer increased 15-folds compared with the parent strain. The optimal conditions for culture medium and the operational conditions for lab-scale fermenter were investigated. Under optimized conditions, the maximal hydroquinone (HQ) tolerance of cells and yield of α-arbutin were 120 mM and 30.6 g/l, respectively. The molar conversion yield of α-arbutin based on the amount of HQ supplied reached 93.6 %. The product was identified as α-arbutin by 13C NMR and 1H NMR analysis. In conclusion, the results in this work provide a one-step and cost-effective method for the large-scale production of α-arbutin.
Article
Safety is a major concern in developing commercial skin-lightening agents. Here, we report the modulating effects of deoxyArbutin (dA) and its second-generation derivatives - deoxyFuran (dF), 2-fluorodeoxyArbutin (fdA), and thiodeoxyArbutin (tdA) - on tyrosinase, and consequently, on melanization. Results demonstrate that dA and its derivatives inhibit tyrosine hydroxylase and dopa oxidase activity of tyrosinase. The inhibition is dose-dependent, thereby inhibiting melanin synthesis in intact melanocytes, when used at concentrations that retain 95% viability of the treated cells in culture. Herein we demonstrate that dA, and its second-generation derivatives dF, fdA, and tdA, exhibit dose-dependent reductions in melanocyte cell number, primarily due to inhibition of proliferation rather than initiation of apoptosis as exemplified by hydroquinone (HQ), ie, cytostatic as opposed to cytotoxic. Human and murine melanocytes with functional mutations in either tyrosinase or tyrosinase-related protein 1 (Tyrp1) are less sensitive to the cytostatic effects of dA and its derivatives. Minimal amounts of reactive oxygen species (ROS) were generated upon treatment with dA and its derivatives, in contrast to a dramatic amount of ROS induced by HQ. This increase in ROS subsequently induced the expression of the endogenous antioxidant catalase in treated melanocytes. Treatment with exogenous antioxidants provided protection for melanocytes treated with HQ, but not dA and its derivatives, suggesting that HQ exerts more oxidative stress. These studies demonstrate that dA and its derivatives are relatively safe tyrosinase inhibitors for skin lightening or for ameliorating hyperpigmented lesions.
Article
Organic solvent extracts from fresh twig bark of Japanese pear cultivars (Pyrus serotina) Shinko and Nijisseiki, and European pear cultivar (P. communis) Le Lectier were obtained by maceration with n-hexane and EtOAc, and analyzed in GC-EIMS experiments. In these two Japanese cultivars, the lupeol, betulin, epifriedelinol, friedelin and arbutin contents of Nijisseiki were higher than those of Shinko. In the case of the lupane-type triterpenes, lupeol and betulin, the lupeol content of Japanese pears Shinko and Nijisseiki was higher than that of European pear Le Lectier. The betulin content of Le Lectier was higher than those of Shinko and Nijisseiki. Friedelane-type triterpenes, epifriedelinol and friedelin, were not detected in twig bark of Le Lectier. Quantitative and qualitative differences in the constituents of these three pear cultivars were observed.