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Mushroom tyrosinase inhibitory activity and major fatty acid constituents of Amazonian native flora oils


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In order to treat hyperpigmentation-related problems, there has been a global trend in developing cosmetics claiming to have skin-whitening properties, which act by inhibiting melanin biosynthesis. The objective of this work was to evaluate the in vitro mushroom tyrosinase inhibitory activity of five Amazonian native flora oils, and so to verify the possibility of their incorporation into cosmetic products. In addition, the fatty acid composition of the essential oils was determined by gas chromatography-flame ionisation detection in order to determine the main components of these oils. The tyrosinase inhibitory activity of the tested oils was found to be in the following order: açaí (IA 50 = 66.08 μg mL -1) > tucumã > patauá > pracaxi > castanha do Brasil. This study suggests that açaí oil has great potential in the treatment of hyperpigmentation and other related disorders, due to its considerable tyrosinase inhibitory activity.
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*Correspondence: N. R. B. Raposo. Universidade Federal de Juiz de
Fora, Campus Universitário. Rua José Lourenço Kelmer, s/n, São Pedro -
36036-900 - Juiz de Fora - MG, Brazil. Tel/fax: 55 32 3229 3809. E-mail:
Brazilian Journal of
Pharmaceutical Sciences
vol. 48, n. 3, jul./sep., 2012
Mushroom tyrosinase inhibitory activity and major fatty acid
constituents of Amazonian native flora oils
Raquel da Silva Teixeira1, Paula Rafaela Rocha1, Hudson Caetano Polonini1,2, Marcos Antônio
Fernandes Brandão1,2, Maria das Graças Afonso Miranda Chaves2, Nádia Rezende Barbosa Raposo1, 2,*
1NIQUA, Federal University of Juiz de Fora, 2NUPICS, Federal University of Juiz de Fora
In order to treat hyperpigmentation-related problems, there has been a global trend in developing cosmetics
claiming to have skin-whitening properties, which act by inhibiting melanin biosynthesis. The objective
of this work was to evaluate the in vitro mushroom tyrosinase inhibitory activity of ve Amazonian
native ora oils, and so to verify the possibility of their incorporation into cosmetic products. In addition,
the fatty acid composition of the essential oils was determined by gas chromatography-ame ionisation
detection in order to determine the main components of these oils. The tyrosinase inhibitory activity of
the tested oils was found to be in the following order: açaí (IA50 = 66.08 µg mL-1) > tucumã > patauá
> pracaxi > castanha do Brasil. This study suggests that açaí oil has great potential in the treatment of
hyperpigmentation and other related disorders, due to its considerable tyrosinase inhibitory activity.
Uniterms: Amazonian plants/evaluation/dermatological use. Skin lightening agents. Tyrosinase/
inhibition/in vitro evaluation. Melanin. Hyperpigmentation/treatment.
Com o intuito de se tratar problemas dermatológicos de hiperpigmentação, há uma tendência mundial no
desenvolvimento de cosméticos que possuam propriedades despigmentantes, os quais agem inibindo a
biossíntese de melanina. O objetivo deste trabalho foi avaliar in vitro a atividade de inibição da tirosinase
de cogumelo de cinco óleos de plantas nativas da Amazônia e, desta forma, vericar a possibilidade de sua
incorporação em produtos cosméticos. Ainda, a composição de ácidos graxos dos óleos foi determinada
por cromatograa gasosa com detecção por ionização de chama, no intuito de determinar os principais
componentes destes óleos. A atividade de inibição da tirosinase dos óleos testados foi encontrada na
seguinte ordem: açaí (IA50 = 66,08 µg mL-1) > tucumã > patauá > pracaxi > castanha do Brasil. Este
estudo sugere que o óleo de açaí possui grande potencial para o tratamento da hiperpigmentação cutânea
e doenças correlatas, devido à sua considerável atividade de inibição da tirosinase.
Unitermos: Plantas amazônicas/avaliação/uso dermatológico. Despigmentantes. Tirosinase/inibição/
avaliação in vitro. Melanina. Hiperpigmentação cutânea/tratamento.
The major determinant of the colour of mammalian
skin and hair is the content and distribution in keratino-
cytes of the melanins, coloured polymorphous biopoly-
mers produced from complex and multi-step oxidative
reactions involving the amino acid L-tyrosine (Adhikari
et al., 2008; Lin et al., 2011). This pigment acts primarily
by defending animals from ultraviolet (UV) radiation.
However, its abnormal production is related to an increase
in the number of melanocytes and/or increased activity
of melanogenic enzymes. This can result in considerable
aesthetic problems due to hyperpigmentation, namely
freckles, melasma, liver spots, age spots and others (Ad-
hikari et al., 2008).
In order to treat hyperpigmentation-related prob-
lems, there has been a global trend in developing cosmetics
claiming to have skin-whitening properties, which act by
inhibiting melanin biosynthesis (Lin et al., 2011). This can
be achieved by protecting the skin from solar light expo-
sure, removing melanin by corneal ablation, blocking or
diminishing the proliferation of melanocytes or inhibiting
R. S. Teixeira, P. R. Rocha, H. C. Polonini, M. A. F. Brandão, M. G. A. M. Chaves, N. R. B. Raposo
tyrosinase activity, since melanin is derived from tyrosine
and its biosynthesis is to a large extent regulated by this
copper-containing enzyme (Wang et al., 2006; Ha et al.,
Current research is focused on both synthetic and
natural sources for reducing melanin formation (Arung
et al., 2011; Park et al.., 2011). With respect to natural
substances, the Amazon biome is a major source of new
species and therefore molecules that may have pharma-
cological activity, skin-whitening included. In this light,
the objective of this work was to evaluate the mushroom
tyrosinase inhibitory activity of ve Amazonian native
ora oils, and so to verify the possibility of their incorpo-
ration into cosmetic products. In addition, the fatty acid
composition of the essential oils was determined by gas
chromatography in order to determine the main compo-
nents of these oils.
Plant material
Vegetable oils of Astrocaryum vulgare Mart. (Are-
caceae, popular name tucumã), Bertholletia excelsa Bonpl.
(Lecythidaceae, popular name castanha do Brasil). Euter-
pe oleraceae M. (Areaceae, popular name açaí) Oenocar-
pus bataua Mart. (Arecaceae, popular name patauá) and
Pentaclethra macroloba (Willd.) Kuntze (Mimosaceae,
popular name pracaxi) were acquired from the Amazonian
oil industry (Pará, Brazil).
Tyrosinase inhibition: qualitative enzymatic
reaction screening
The assay was performed according to the protocol
described by Macrini et al. (2009), with some modifi-
cations. Aliquots of 10 µL of a solution composed of
125 U mL-1 of mushroom tyrosinase (Sigma-Aldrich,
USA) were added to 96-well microplates, and then 70 µL
of pH 6.8 phosphate buffer solution and 60 µL of the
Amazonian native ora oils (350 µg mL-1, in 25% dimethyl
sulphoxide, DMSO) were also added. For the positive
control, 60 µL of kojic acid (17.5 µg mL-1 in 25% DMSO)
was used instead of the Amazonian oil, and for the negative
control, 60 µL of 2.5% DMSO was added. To the resultant
mixture, 70 µL of L-tyrosine (Sigma-Aldrich, USA) were
added at a concentration of 0.3 mg mL-1 in distilled water
(the nal volume in the wells was 210 µL).
The absorbance of the microplate wells was read
using a microplate spectrophotometer (SpectraCount,
Packard, USA) at 510 nm (T0). Then, the microplates were
incubated at 30 ± 1ºC for 60 min and the absorbance was
measured again (T1). An additional incubation period of
60 min at 30 ± 1ºC was done and, after this period, a new
spectrophotometric reading was taken (T2).
The inhibitory percentage at the two time points (T1
and T2) was obtained according to the formula:
where IA% = inhibitory activity; C = negative control ab-
sorbance; S = sample or positive control absorbance (ab-
sorbance at time T1 or T2 minus the absorbance at time T0).
Tyrosinase inhibition: quantitative enzymatic
reaction assay
For the samples that reached an IA% greater than
35%, a quantitative assay was conducted. For this pur-
pose, the above experimental protocol was followed,
with modications (a 500 U mL-1 tyrosinase solution was
used instead of 125 U mL-1 and the optical densities were
measured every 10 min for 1 h).
The quantitative determination was obtained
through an analytical curve and the respective equation
of the line. For this, the oils were diluted in the microplate
wells to concentrations of 100, 80, 40, 20 and 10 µg mL-1
with 25% DMSO, and the kojic acid was diluted to con-
centrations of 10, 5, 2.5, 1.25 and 0.625 µg mL-1. The
analytical curve was plotted between tyrosinase inhibition
activity percentages at each time point and the concentra-
tions of the oils/ positive control. Using the equation of
the line, the inhibitory activity at 50% (IA50, in µg mL-1)
was calculated.
Fatty acids assay
For essential oil lipid hydrolysis, 10 mg of the oils
were dissolved in 100 µL of a mixture of ethanol and
1 mol L-1 potassium hydroxide (95:5, v/v) in 2 mL cryo-
genic tubes. After 10 s of vigorous mechanical agitation,
the oils were hydrolysed in a microwave (Panasonic, Ja-
pan), using 80 W of power for 5 min; they were then cooled
and the following reagents were added to the tubes, in this
order: 400 µL of 20% hydrochloric acid, one spatula tip of
sodium chloride and 600 µL of ethyl acetate. Sample were
agitated for a further 10 s, followed by a 5 min rest period.
A 300 µL aliquot from the organic layer was transferred
to a microcentrifuge tube and dried in an oven in order to
obtain the free fatty acids. The residues were methylated
with 14% boron triuoride in methanol and heated in a
Mushroom tyrosinase inhibitory activity and major fatty acid constituents of Amazonian native ora oils 401
water bath for 10 min at 80 ºC. The resulting solution was
injected into an HP5890 gas chromatograph (HP, USA)
with a flame ionisation detector. The instrument was
equipped with a 15 m x 0.25 mm HP-INNOWax column,
1 µL injection (1/50 split) with hydrogen as the carrier
gas (2 mL min-1). The temperature of both the detector
and the injector was maintained at 250 ºC, and the column
was subjected to a temperature gradient (initial = 80 ºC,
then an increase of 7 ºC min-1 to 240 ºC). The identica-
tion of the peaks was made by comparison with Supelco
37 methylated fatty acids (Supelco, USA) using the same
conditions described above.
Statistical analysis
All data were reported as mean (n=3). The com-
parison between the values obtained with the different oils
and the reference drug (kojic acid) was achieved through
a Student’s t-test to calculate p-values (α = 0.05), using
the software Statistical Package for the Social Sciences®
(SPSS) v. 14.0.
Oils from plants are increasingly gaining more at-
tention from pharmacists, physicians and chemists due to
their great scope of applications in different elds such
as cosmetics, perfumery, pharmaceuticals and the food
industry. Since they have a wide range of pharmacological
applications due to their highly complex chemical compo-
sition, currently, there is a global trend toward replacing
synthetic substances with natural extracts (Al-Mamary et
al., 2011).
One of the abilities of plant materials currently being
researched is the inhibition of the tyrosinase enzyme, but
these studies have mainly been focused on crude drugs or
plant extracts, and not on plant oils (Adhikari et al., 2008).
Since the Brazilian Amazon is renowned worldwide for
its great plant diversity and potential for new pharmaceu-
ticals, this study selected five well-known Amazonian
species for screening their capability in being used as raw
materials for skin-whitening agents, which are sought after
by the cosmetic market.
According to Momtaz et al. (2008), vegetable oils
are rich in compounds containing hydrophobic compo-
nents, which can act as competitive inhibitors for the en-
zyme tyrosinase, and so on melanin synthesis. According
to these authors, plant oils have great reducing power, this
being the principle for exploring the tyrosinase inhibitory
potential of plants, which may also have phytoconstitu-
ents that chelate the copper ions present in the active site
of the tyrosinase enzyme. It is also important to discover
new skin-whitening agents because some of the currently
used substances are characterised by high toxicity, as hy-
droquinone (Macrini et al., 2009).
To our knowledge, this is the first report of such
activity for these species, and all of the ve Amazonian
vegetable oils screened for their tyrosinase inhibition
activity showed some degree of activity, as can be seen
in Table I. The tyrosinase inhibitory activity of tested oils
was found to be in the following order: açaí > tucumã >
patauá > pracaxi > castanha do Brasil. Thus, the natural oil
obtained from the açaí was the most active in the present
study, as it had an IA50 close to kojic acid, the gold standard
for this activity.
Our methodology included two screenings and a
nal quantitative step. The tyrosinase concentration of
125 U mL-1 in the rst test was adopted to increase the
chances of discovering an oil with potential skin-whit-
ening activity. As all oils seemed to possess such activity
(p < 0.05), they were submitted to the second screening,
and as they continued to show some activity, they were all
subjected to the quantitative analysis in order to discover
which was the most effective and therefore has the greatest
potential for the cosmetic/pharmaceutical industry.
According to Table I, it can be noted that the oils
maintained their 60 min activity in the second screening,
and so one can infer that they did not lose their tyrosinase
inhibition activity. Conversely, kojic acid went from
73.13% inhibition in the rst hour to 42.77% in the second
hour. Açaí oil, with a good IA50, had the longest duration of
action, compared to kojic acid, which may be a desirable
characteristic for a skin-whitening product as it decreases
the need for constant reapplication of the product to the
TABLE I - Tyrosinase inhibitory activity of oils from the Amazon
Sample IA 60 min
IA 120 min
(µg mL-1)
Açaí 38.56* 38.98 66.08*
Castanha do
Brasil 34.69* 34.70 1605.27
Patauá 35.15* 34.86 668.03
Pracaxi 37.75* 35.43 781.52
Tucumã 38.38* 37.69 557.91
Kojic acid 73.13 42.77 5.86
IA (%) = percentage of inhibitory activity; IA50 = inhibitory
activity at 50%; * p < 0.05 versus control.
R. S. Teixeira, P. R. Rocha, H. C. Polonini, M. A. F. Brandão, M. G. A. M. Chaves, N. R. B. Raposo
In order to know the composition of the studied oils,
a gas chromatography analysis was also performed, as can
be seen in Table II and Figure 1. The results show that the
oils possessed both saturated and unsaturated fatty acids,
the latter being considered essential fatty acids. This,
coupled with the tyrosinase inhibition results, led to the
inference that they can be included in functional foods
and cosmetics.
Theoretically, one can imagine that the high skin-
whitening property found in açaí oil may be due to the
presence of oleic acid (C18:1) in its composition, since this
was the main component in the chromatographic analysis.
However, further studies must be conducted with its com-
ponents separately in order to determine which specic
compound is responsible for enzyme inhibition. However,
it has been noted that natural products generally exert their
activity by synergy between their various compounds,
and a single substance is generally not responsible for the
biological effects found in natural products.
FIGURE 1 - Gas chromatograms of the studied Amazonian oils. Acids: C12:0 – lauric; C14:0 – myristic; C16:0 palmitic; C16:1
palmitoleic; C18:0 – stearic; C18:1 oleic; C18:2 linoleic; C18:3 – linolenic; C20:0 arachidic; C22:1 erucid; C24:0 – lignoceric.
Mushroom tyrosinase inhibitory activity and major fatty acid constituents of Amazonian native ora oils 403
TABLE II - Main constituents of Amazonian native oils
Fatty acid (%) Oil
Açaí Castanha do Brasil Patauá Pracaxi Tucumã
C12:0 nd 0.3 nd nd nd
C14:0 nd 0.4 nd nd nd
C16:0 22.8 15.3 11.8 2.7 21.2
C16:1 4.2 0.3 0.5 nd nd
C18:0 1.9 10.6 3.8 5.3 5.1
C18:1 60.7 42.6 79.1 53.3 66.6
C18:2 9.6 30.2 4.5 25.5 5.3
C18:3 0.3 nd nd 2.5 1.8
C20:0 nd nd nd 1.3 nd
C22:0 nd nd nd 5.0 nd
C22:1 nd nd nd 1.6 nd
C24:0 nd nd nd 1.8 nd
nd = not detectable. Acids: C12:0 – lauric; C14:0 – myristic; C16:0 palmitic; C16:1 – palmitoleic; C18:0 – stearic; C18:1 oleic;
C18:2 – linoleic; C18:3 – linolenic; C20:0 – arachidic; C22:0 – behenic; C22:1 – erucid; C24:0 – lignoceric.
This study suggests that açaí oil has great potential
for the treatment of hyperpigmentation and other related
disorders due to its considerable tyrosinase inhibitory
activity. Thus, this may be an interesting candidate for
evaluation in more complex biological assays such as me-
lanocyte cultures and eventually in animal/human assays.
However, for the raw material be effectively incorporated
into the cosmetic market, it is now required to develop an
adequate delivery system/formulation for its topical use
in humans and for this activity be assessed in animal cells.
This research was supported by FAPEMIG, CNPq,
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Received for publication on 10th February 2012
Accepted for publication on 3rd May 2012
... The SFAs are composed of palmitic (21-25%), stearic (2.6-5.1%), and arachidic (4%) acids. The oil presents a low amount of PUFAs such as linoleic (<5%) and linolenic (<3%) [12,134,148,159]. Other FAs reported in small concentrations (<1%) include tricosanoic, myristic, lauric, arachidonic, gondoic, docosadienoic, margaric, palmitoleic, lignoceric, and behenic acids [160]. ...
... ACP oil is mainly composed of oleic acid (52-62%) and palmitic acid (23-27%). ACP oil also presents linoleic (7-11%), palmitoleic (4-5%), and stearic (<2%) acids [139,141,159]. A concentration between 3.39 and 4.80% of cis-11-octadecenoic acid (or cis-vaccenic acid, C18:1n11) has been reported. ...
... Oleic and palmitic acids are the major FAs in PTP oil [10][11][12]57,159]. The oleic acid content in PTP oil can vary depending on the country. ...
Full-text available
Arecaceae palm tree fruits (APTFs) with pulp or kernel rich in oil are widely distributed in six Brazilian biomes. APTFs represent a great potential for the sustainable exploitation of products with high added value, but few literature studies have reported their properties and industrial applications. The lack of information leads to underutilization, low consumption, commercializa-tion, and processing of these fruit species. This review presents and discusses the occurrence of 13 APTFs and the composition, physicochemical properties, bioactive compounds, and potential applications of their 25 oils and fats. The reported studies showed that the species present different lipid profiles. Multivariate analysis based on principal component analysis (PCA) and hierarchical cluster analysis (HCA) indicated a correlation between the composition of pulp and kernel oils. Myristic, caprylic, capric, and lauric acids are the main saturated fatty acids, while oleic acid is the main unsaturated. Carotenoids and phenolic compounds are the main bioactive compounds in APTFs, contributing to their high oxidative stability. The APTFs oils have a potential for use as foods and ingredients in the cosmetic, pharmaceutical, and biofuel industries. However, more studies are still necessary to better understand and exploit these species.
... The current skin-whitening agents for improving skin pigmentation such as hydroquinone (benzene-1,4-diol or quinol), a derivative of benzene and antimelanogenic agents including retinol, are characterized by high toxicity, burning, redness, allergy, and cancer. 20,21 Researchers have been focusing on developing natural whitening agents with selective activity on TYR to reduce hyperpigmentation without toxicity to normal and healthy cells. 19 Naturally occurring hydrolyzable tannins such as coumaric acid and caffeic acid were reported to have inhibited melanin production with no significant cytotoxicity. ...
Full-text available
This study extracted ellagitannins from rambutan peel using the Soxhlet technique. The extract was further partitioned and fractionated to get extract rich in ellagitannin and geraniin, respectively. The partitioning of the extract significantly increased total phenolic content (TPC) by 36.3% and its biological properties. Mineral elements such as Ca, Cr, Cu, Fe, K, Mg, Mn, Na, Ni, and Zn were identified in both peel and extract. Ellagitannins such as geraniin and corilagin with metabolites (gallic acid and ellagic acid) were identified as the major compounds. Analysis of antioxidant activities shows that the ellagitannin rich extract is as powerful as vitamin C. Geraniin was the main contributor to the free radical scavenging activity. The study also revealed that extract with a fraction rich in geraniin has antioxidant activity equivalent to commercial geraniin (1.56 ± 0.11 Trolox equivalent g/g). It also showed low cytotoxicity on fibroblast L929 cells, moderate tyrosinase activity, and good efficacy against Staphylococcus aureus, Staphylococcus epidermidis, and Cutibacterium acnes strains. Successive fractionation of the extract is a promising technique to produce geraniin rich fractions with enhanced antioxidant property. Rambutan peel, as a natural product, is a good source of mineral elements and biologically active compounds for pharmaceutical, nutraceutical, and cosmetic formulations.
... Quantitative assay was conducted for the extracts that exhibited an IA% greater than 35% (Teixeira et al., 2012). The quantitative evaluation of tyrosinase inhibition activity was determined via a calibration curve and the respective line equation. ...
Context: Sage (Salvia officinalis) is an ancient valuable plant used in the treatment of variant health issues. Aims: To evaluate the depigmentation activity of S. officinalis leaf chloroformic (SOCF) and ethanolic (SOMF) extracts via its efficacy to inhibit tyrosinase enzyme using in vitro model and bioassay-guided identification and quantification of the main active constituents. Methods: Plant extracts efficacy as a depigmentation agent has been studied via mushroom tyrosinase inhibition using in vitro model at two concentrations (100 and 200 µg/mL). Extracts were analyzed for phenolic compounds that could be responsible for the biological activity using LC-MS/MS analysis. Results: Significant potency at a high concentration of 200 µg/mL for the methanolic extract were recorded (p≤0.05). The LC-MS/MS analysis of S. officinalis leaf extracts revealed the presence of eight and fourteen analytes of origin of thirty-seven analytes in both SOCF and SOMF, respectively. Analytes’ quantification recorded the highest amount for rosmarinic acid (46 016 µg/g) in SOMF and the lowest was hesperidin (0.6 µg/g) in SOCF. Conclusions: S. officinalis extracts recorded significant tyrosinase inhibition potency could control the melanin synthesis process and exhibit beneficiary effect in hyperpigmentation issues.
... Tucumã-do-Pará fruit extract (0.1 g/mL) was classified by Baurin et al. (2002) as a poor tyrosinase inhibitor, since it was only capable to inhibit 16% of the mushroom tyrosinase enzyme. On the other hand, the oil from the same species exerted a much higher antityrosinase potential, inhibiting 50% of the enzyme activity at 557.91 μg/mL (Teixeira et al., 2012). That being said, A. vulgare lipophilic bioactive compounds should be separately evaluated to understand its anti-tyrosinase mechanisms. ...
Latin America has a wide range of native plants spread through its territory. The palms of the Astrocaryum genus are examples of crops occurring in Central and South America, including the large plant life in Brazil. Although not very well known, the Astrocaryum spp. possess edible and non-edible fractions with potential technological and medicinal uses, as evidenced by recent research. Two native Brazilian fruits, tucumã-do-Amazonas (Astrocaryum aculeatum) and tucumã-do-Pará (Astrocaryum vulgare), typically found in the north and northeast of the country, respectively, stand out for their high antioxidant capacity and rich content in bioactive compounds, mainly carotenoids and phenolic compounds. Accordingly, experimental studies indicate their potential to prevent and treat inflammatory and oxidative stress-related conditions, including cancer. The tucumã plants have also been suggested as tools in the industry, for example for biofuel production, activated carbon technology, and as alternative packaging. Considering the importance of bringing light to underestimated yet culturally relevant native crops with potential benefits for small and large communities, this review aims to present and discuss the characteristics, bioactive composition, health effects, and technological potential of tucumã-do-Amazonas and tucumã-do-Pará fruits.
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Apesar da enorme diversidade de espécies produtoras de óleo existentes na Amazônia e das numerosas possibilidades de aplicação destes, poucas espécies têm sido exploradas, assim para melhor compreensão sobre a utilização e o potencial desses óleos, o presente trabalho traz, por meio de uma revisão integrativa narrativa, inferências científicas sobre produção, uso e potencialidades de óleos extraídos de açaís (Euterpe oleracea) da Amazônia legal. A revisão foi elaborada, durante o período de fevereiro de 2022 a agosto de 2022, por meio das principais bases de dados e selecionou, por leitura inicial de títulos e resumos e posteriormente leitura dos textos completos, artigos que tratassem do óleo de açaí, excluindo trabalhos que investigaram apenas açaí, ou apenas óleos de outras espécies vegetais, além de publicações que não fossem revisadas por pares e publicadas nos últimos. A compilação dos artigos elegíveis evidenciou as potencialidades tecnológicas da espécie para produção de óleo, a segurança do uso como alimento para espécies humana e animal, mostrou sucesso e problemas relacionados à exploração industrial, alimentícia, cosmética e farmacêutica desse produto e alerta para necessidade de maiores incentivos e novos avanços em pesquisa, desenvolvimento e inovação no uso dessa espécie para produção de óleo. Palavras-chave: Óleo Vegetal, Óleo de Açaí, Planta Amazônica.
Background: Essential oils (EOs) have been considered as a potential alternative therapy for wound healing and scar reduction. Objective: To provide a comprehensive review examining the effects of EOs on wound healing and scars. Data sources: PubMed, Cochrane, Ovid and Embase computerized searches were performed through June 2020. Review methods: Two independent reviewers conducted data extraction reviewed by the senior author following the PRISMA protocol. Results: Three manuscripts examining three different EO-containing topical agents were analyzed. Outcomes include: healing rate, erythema, pain, pruritus, patient discomfort, physician satisfaction, percent wound reduction, wound/scar surface perimeter area, and qualitative dermatological evaluation. All articles concluded that the EO-containing topical agents resulted in either superior or non-inferior outcomes in comparison to controls. Hypericum-Calendula oil obtained lower wound surface perimeter area. Erythema (p=.001) was significantly decreased by the peppermint EO-containing topical agent preparation. Physicians also reported greater satisfaction (p<.001) in wound appearance with use of the peppermint EO-containing topical agent. CONCLUSION: A paucity of studies have examined EO use for wound healing and scar reduction. Treatment with EO-containing topical agents resulted in decreased erythema with increased physician satisfaction of wound appearance. Future studies should assess what level of purity is needed for improved results, and which EO, or combination of EOs is most beneficial.
Hyperpigmentation disorders are characterized by dark spots on the skin. Treatment for hypermelanosis involves the application of tyrosinase inhibitors, chemical peels, or lasers therapy, although they may cause skin irritation and other side effects. Potential natural alternatives for skin hyperpigmentation are quercetin (QT) and olive oil (OL) due to their antioxidant activity and anti-tyrosinase property. However, QT usage drawback is its low water solubility and high chemical instability that may be overcome with nanoencapsulation. To understand if QT and OL could be used as alternative to improve hypermelanosis, we evaluated the physical-chemical and biological properties of quercetin-loaded olive oil nanoemulsion (QT-NE). QT-NE was prepared by the high-energy emulsification method and, through the Box-Behnken design, we analyzed different concentrations of OL, surfactant mixture, and the agitation speed in relation to diameter and polydispersity index (PdI). The optimized formulation was characterized in terms of size, PdI, zeta potential, pH, electrical conductivity, stability and encapsulation efficiency. Besides, we evaluated in vitro antioxidant activity, tyrosinase inhibitory activity, and in vitro toxicity. The optimized QT-NE showed a size of 183.43 ± 9.53 nm with low PdI (∼0.19), zeta potential of −17.13 ± 0.61 mV, pH around 7, conductivity of 163.96 ± 8.92 µS/cm, and high encapsulation efficiency (∼99%). The QT-NE exhibited high antioxidant activity (∼92%) and inhibited 56% of tyrosinase activity, indicating its potential for free radical scavenging and reducing skin hyperpigmentation. Furthermore, no irritation was observed by HET-CAM. Thus, this nanoemulsion (NE) is a promising alternative for hypermelanosis and could substitute the current treatments.
Pentaclethra macroloba (Willd.) Kuntze seeds oil has been used as a topical healing agent, applied mainly to parturients and snake bites. The objective was to investigate the effects of pracaxi oil (POP) on HepG2/C3A cells under cytogenotoxicity, cell cycle and apoptosis influence, and expression of metabolism and other related cell types proliferation genes. Cytotoxicity was analyzed by MTT test and apoptosis and cell cycle interferences by flow cytometry. To identify genotoxicity were used comet and micronucleus tests. RT-qPCR investigated gene expression. PO chemical characterization has shown two significant triterpenes, identified as oleanolic acid and hederagenin. The results showed that the PO did not reduce cell viability at concentrations ranging from 31 to 500 μg/mL. Comet and micronucleus assays revealed the absence of genotoxic effects, and flow cytometry showed no cell cycle or apoptosis disturbance. RT-qPCR indicated that PO up-regulated genes related to metabolism (CYP3A4, CYP1A2, CYP1A1), cell proliferation (mTOR), and oxidative stress (GPX1). The data indicate that PO has no cytogenotoxic effects and suggest that it activated the PI3/AKT/mTOR cascade of cell growth and proliferation. Inside the cells, the PO activated xenobiotic metabolizing genes, responsible for reactive oxygen species (ROS) generation, can neutralize ROS with increased GPX1 gene expression without genetic damage, interruption of the cell cycle, or induction of apoptosis.
Astrocaryum vulgare is an Amazon palm species, popularly known as tucumã. A. vulgare oil has diverse biological purposes, but low solubility in water. Nanoemulsions provide a solution to this problem. This study aimed to evaluate the influence of different surfactants on the development of nanoemulsions. To determine the hydrophilic-lipophilic balance (HLB), the influence of different surfactants on nanoemulsification was determined, the region of nanoemulsion formation on the pseudo-ternary phase diagram was analyzed, nanoemulsions were characterized, and the best candidate was subjected to stability assessment. The HLB was 14, and PPG-5-Ceteth-20 and sorbitan oleate were selected as surfactants. The nanoemulsion had a droplet size of 174.1 nm, a polydispersity index of 0.295, and a zeta potential of 20.7. A. vulgare oil is used in the Amazon for countless pharmaceutical applications. We demonstrate the impact of the chemical structure of surfactants, resulting in the formation of nanoemulsions containing A. vulgare oil.
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Dermatological disorders related to pigmentation result in tenuous hyper or hypopigmentation Cosmetic and pharmaceutical products containing depigmenting substances are used in the treatment of patients who have high pigmentation disorders, such as melasma or chloasma, post-inflammatory hyperpigmentation, senile lentigo and ephelides. Skin lightening agents are not yet totally effective or safe and therefore intensive research for the discovery of new agents is continuous. Enzyme inhibitors involved in melanogenesis, such as tyrosinase, have been discovered in Asian countries, including those isolated from plant extracts. The Brazilian flora has the highest species diversity in the world, and the chemical, pharmacological and cosmetic potential for the discovery of new skin whitening agents is in proportion with this biodiversity. For these reasons, 25 aqueous and 24 organic extracts obtained from 19 plants native to the Amazon rain forest and to the Atlantic forest, belonging to 11 different families, were evaluated as tyrosinase inhibitors. Nine out of 49 extracts showed inhibitory activity in the screening process. The 50% inhibitory activity (IA50) was calculated, revealing that the most active extracts were the organic extracts from the leaves and stem of Ruprechtia sp. (IA50 33.76mg.mL-1) and the organic extract from the aerial organs of Rapanea parviflora (IA50 64.19mg.mL-1).
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The antioxidant and skin whitening properties of essential oils as natural products is the cornerstone to replace synthesized preservatives and to obtain safer source with better biological activities. The present study was designed to investigate the antioxidant and tyrosinase inhibitory activities of twenty essential oils obtained from aromatic plants grown and used in Yemen. Essential oils were hydrodistilled using Clevenger apparatus. The antioxidant activity was examined by three different methods, namely: the ability to scavenge free radicals 2,2-diphenyl-1-picrylhydrazyl (DPPH), the capacity to inhibit lipid peroxidation thiobarbituric acid reactive species (TBARS), and the total reduction power activity (TRPA). The new findings have shown that all the tested essential oils have variable free radical scavenging activity as measured by the DPPH decoloration assay. The new findings have shown that all the tested essential oils have variable antioxidant activities. These activities were dependent on the essential oil and the method used. In addition, the present study showed that most of the tested essential oils have low to high inhibitory effect on tyrosinase inhibitory activity. The current findings suggest that the tested essential oils could be used as an important source for pharmaceutical and neutraceutical applications.
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Melanogenesis inhibition by raspberry ketone (RK) from Rheum officinale was investigated both in vitro in cultivated murine B16 melanoma cells and in vivo in zebrafish and mice. In B16 cells, RK inhibited melanogenesis through a post-transcriptional regulation of tyrosinase gene expression, which resulted in down regulation of both cellular tyrosinase activity and the amount of tyrosinase protein, while the level of tyrosinase mRNA transcription was not affected. In zebrafish, RK also inhibited melanogenesis by reduction of tyrosinase activity. In mice, application of a 0.2% or 2% gel preparation of RK applied to mouse skin significantly increased the degree of skin whitening within one week of treatment. In contrast to the widely used flavoring properties of RK in perfumery and cosmetics, the skin-whitening potency of RK has been demonstrated in the present study. Based on our findings reported here, RK would appear to have high potential for use in the cosmetics industry.
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This study investigated inhibitory effects of N,N-unsubstituted selenourea derivatives on tyrosinase activity. Three types of N,N-unsubstituted selenoureas derivatives exhibited inhibitory effect on dopa (3,4-dihydroxyphenylalanine) oxidase activity of mushroom tyrosinase. Compound D at a concentration of 200 microM exhibited 55.5% of inhibition on dopa oxidase activity of mushroom tyrosinase. This inhibitory effect was higher than that of kojic acid (39.4%), a well known tyrosinase inhibitor. Moreover, the compound D identified as a noncompetitive inhibitor by Lineweaver-Burk plot analysis. In addition, compound D also inhibited the melanin production in melan-a cells.
Artocarpus plants have been a focus of constant attention due to the potential for skin whitening agents. In the in vitro experiment, compounds from the Artocarpus plants, such as artocarpanone, norartocarpetin, artocarpesin, artogomezianol, andalasin, artocarbene, and chlorophorin showed tyrosinase inhibitory activity. Structure-activity investigations revealed that the 4-substituted resorcinol moiety in these compounds was responsible for their potent inhibitory activities on tyrosinase. In the in vitro assay, using B16 melanoma cells, the prenylated polyphenols isolated from Artocarpus plants, such as artocarpin, cudraflavone C, 6-prenylapigenin, kuwanon C, norartocarpin, albanin A, cudraflavone B, and brosimone I showed potent inhibitory activity on melanin formation. Structure-activity investigations revealed that the introduction of an isoprenoid moiety to a non-isoprenoid-substituted polyphenol enhanced the inhibitory activity of melanin production in B16 melanoma cells. In the in vivo investigation, the extract of the wood of Artocarpus incisus and a representative isolated compound from it, artocarpin had a lightening effect on the skin of guinea pigs' backs. Other in vivo experiments using human volunteers have shown that water extract of Artocarpus lakoocha reduced the melanin formation in the skin of volunteers. These results indicate that the extracts of Artocarpus plants are potential sources for skin whitening agents.
Phytochemical investigation of the branches of Ficus erecta var. sieboldii King resulted in the isolation of eight constituents: p-hydroxybenzoic acid (1), methyl p-hydroxybenzoate (2), vanillic acid (3), methyl vanillate (4), syringic acid (5), β-sitosterol (6), α-amyrin acetate (7), and ethyl linoleate (8). Their chemical structures were identified via spectroscopic means as well as by comparing their data with literature values. Studies on tyrosinase inhibition activities were conducted for the isolated compounds. Among them, p-hydroxybenzoic acid (1) and methyl p-hydroxybenzoate (2) were identified as active tyrosinase inhibitors with IC(50) values of 0.98 ± 0.042 and 0.66 ± 0.025 mM, respectively, showing comparable activities to that of arbutin (IC(50) = 0.32 ± 0.015 mM), a standard control. Inhibition kinetics, as analyzed by Lineweaver-Burk plots, indicated that compounds 1 and 2 were competitive inhibitors of diphenolase of mushroom tyrosinase. Notably, isolated compounds 1-8 were reported for the first time as constituents of F. erecta.
South-East Asian population is daily exposed to strong sunlight. As a result, the majority of population will have darker, ethnic skin. Moreover, many people suffer from dark spots, hyperpigmentation, which is considered to be a skin disorder and causes psychological disturbance. To treat dark spots, most of the population will still rely on traditionally used crude drugs, knowledge about which is transferred from generation to generation. Fifty-two crude drugs were selected based on the survey performed among local healers and beauticians of different ethnic origin. These crude drugs were screened for mushroom tyrosinase inhibitory activity, as tyrosinase inhibitors are becoming increasingly important as cosmetic and medicinal products, primarily to control hyperpigmentation. Among the tested crude drugs, methanolic extracts of Glycyrrhiza glabra, Morus alba, Syzygium aromaticum, Citrus aurantifolia, Cypreae moneta, Punica granatum and Citrus aurantium, at the final concentration of 50 microg mL(-1), showed mushroom tyrosinase inhibitory activity of 78.9%, 71.0%, 69.4%, 59.0%, 56.0%, 53.4 and 51.9%, respectively, with 91.4% inhibitory activity of kojic acid taken as positive control. To our knowledge, this is the first report that extracts of Cypreae moneta shell and Syzygium aromaticum flowering bud have tyrosinase inhibitory activity. These potent extracts were further evaluated at different concentration. The final concentration of the extracts in reaction mixtures was 50, 25 and 5 microg mL(-1) for the initial concentration of 1000, 500 and 100 microg mL(-1), respectively. They showed concentration-dependent inhibition of mushroom tyrosinase. Those extracts expressing relatively weak tyrosinase inhibitory activity may act through different inhibition pathway which is not based on tyrosinase activity. Further evaluation of the most potent tyrosinase inhibitors in in vivo conditions would be recommended.
Because tyrosinase catalyzes melanin synthesis, tyrosinase inhibitors are important in cosmetic skin-whitening. Oxidative stress contributes to skin aging and can adversely affect skin health, which means antioxidants active in skin cells may support skin health. We examined 25 traditional Chinese herbal medicines that might be useful for skin-whitening and skin health. Extracts (100microg/mL) were tested for cytotoxicity on human epidermal melanocytes (HEMn); 12 exhibited low cytotoxicity. Their effects on tyrosinase and melanin inhibitory activities and free radical scavenging activities were further assessed. Phenolic contents were evaluated using Folin-Ciocalteu reagent. Four herbs, Pharbitis nil, Sophora japonica, Spatholobus suberectus, and Morus alba, exhibited potent inhibitory effects on tyrosinase (IC(50) values 24.9, 95.6, 83.9, and 78.3microg/mL, respectively). Melanin inhibition was not dose-dependent. Sophora japonica (IC(50): 14.46microg/mL, 1,1-diphenyl-2-picrylhydrazyl (DPPH); 1.95microg/mL, hydroxyl radical) and Spatholobus suberectus (IC(50): 10.51microg/mL, DPPH; 4.36microg/mL, hydroxyl radical) showed good antioxidative activities and high phenolic contents (255 and 189mg of gallic acid/g extract, respectively). Among active anti-tyrosinase extracts, Sophora japonica and Spatholobus suberectus were especially potent in HEMn cells in terms of free radical scavenging effects and high phenolic contents, making them the strongest candidates for cosmetic application found in the current study.
To investigate the stem bark of Sideroxylon inerme L. and its compounds for tyrosinase-inhibition activity and to evaluate the mechanism involved of the most potent compounds in tyrosinase inhibition. Three different extracts (acetone, methanol and dichloromethane) of Sideroxylon inerme L. were evaluated for their inhibitory effect in vitro on the monophenolase and diphenolase activated forms of tyrosinase, using a colorimetric procedure. This test was used for bioactivity-guided isolation of two active compounds using column chromatography and TLC. Active extracts were also investigated for their inhibitory effect on melanogenesis in cultured B16 melanoma cells. Antioxidant activities of the methanolic extract of Sideroxylon inerme and purified compounds were investigated using the 1,2-diphenyl-2-picrylhydrazyl (DPPH) antioxidant assay. The inhibition of tyrosinase activity relative to the inhibition of its activity at the transcriptional level was also studied by determination of the degree of expression of mRNAs for this gene by using extract of Sideroxylon inerme-treated cells (B16F10) and semi-quantitative RT-PCR. Methanolic and acetonic extracts of the stem bark of Sideroxylon inerme showed significant inhibition of monophenolase activity (IC50 values of 63 microg/ml and 82 microg/ml, respectively). The methanolic extract also exhibited 37% reduction of melanin content at 6.2 microg/ml in melanocytes without being significantly toxic to the cells. Examination for inhibition of monophenoloxidase in situ on TLC, followed by column chromatographic purification of the stem bark extract of Sideroxylon inerme, resulted in the isolation of two active compounds, epigallocatechin gallate and procyanidin B1, with IC50 values against monophenolase of 30 microg/ml and > 200 microg/ml, respectively. Epigallocatechin gallate exhibited a greater anti-tyrosinase activity than arbutin. Sideroxylon inerme bark extracts, epigallocatechin gallate and procyanidin B1 exhibited antioxidant DPPH radical scavenging activities with EC50 values of 1.54 microg/ml, 1.33 microg/ml and 1.68 microg/ml, respectively and were not particularly cytotoxic. During mechanism studies it was evident that at the transcription level, Sideroxylon inerme (25 microg/ml) was acting as a potent tyrosinase inhibitor compared to controls (untreated cells and kojic acid). The bark extract of Sideroxylon inerme and the two isolated compounds warrant further investigation in clinical studies to be considered as skin-depigmenting agents.
Cosmetic applications of selected traditional Chinese herbal medicines
  • K H Lin
  • R Hsu
  • F L Huang
  • Y H Chang
  • H C Huang
  • C Y Lee
WANG, K.H.; LIN, R.; HSU, F.L.; HUANG, Y.H.; CHANG, H.C.; HUANG, C.Y.; LEE, M.H. Cosmetic applications of selected traditional Chinese herbal medicines. J. Ethnopharmacol., v.106, p.353-359, 2006.