Identification of Coumarins and Antimicrobial Potential of Ethanolic Extracts of Dipteryx odorata and Dipteryx punctata

Sousa, Bruna Cristine Martins de; Castro, Santana Pinto de; Lourido, Katiane Araújo; Kasper, Aline Aparecida München; Paulino, Geomarcos da Silva; Delarmelina, Camila; Duarte, Marta Cristina Teixeira; Sartoratto, Adilson; Vieira, Thiago Almeida; Lustosa, Denise Castro; Barata, Lauro Euclides Soares

doi:10.3390/molecules27185837

Cited by 8 publications

(10 citation statements)

References 36 publications

(29 reference statements)

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“…They are commonly found in various dietary plants, particularly in cinnamon and many fruits and vegetables [ 18 ]. Different derivatives of these compounds exhibit diverse biological activities, including antioxidant, anti-inflammatory, antimicrobial, and in vitro and in vivo platelet anti-aggregation effects [ 10 , 11 , 18 , 19 , 20 , 21 ]. Natural coumarins and their derivatives have always provided an invaluable source for the discovery of novel melanogenic and/or tanning agents.…”

Section: Discussionmentioning

confidence: 99%

A 7-Hydroxy 4-Methylcoumarin Enhances Melanogenesis in B16-F10 Melanoma Cells

Kim

Hyun

2023

Molecules

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The objectives of this study were to investigate the melanogenetic potentials of the naturally occurring 7-hydroxy coumarin derivatives 7-hydroxy 5,6-dimethoxycoumarin (7H-5,6DM), 7-hydroxy 6,8-dimethoxycoumarin (7H-6,8DM), 7-hydroxy 6-methoxycoumarin (7H-6M), and 7-hydroxy 4-methylcoumarin (7H-4M) in the melanogenic cells model for murine B16F10 melanoma cells. The initial results indicated that melanin production and intracellular tyrosinase activity were significantly stimulated by 7H-4M but not by 7H-5,6DM, 7H-6,8DM, or 7H-6M. Therefore, our present study further investigated the melanogenic effects of 7H-4M in B16-F10 cells, as well as its mechanisms of action. In a concentration-dependent manner, 7H-4M increased intracellular tyrosinase activity, leading to the accumulation of melanin without affecting the viability of B16-F10 cells. Our study further investigated the effects of 7H-4M on melanogenesis, including its ability to promote tyrosinase activity, increase melanin content, and activate molecular signaling pathways. The results indicate that 7H-4M effectively stimulated tyrosinase activity and significantly increased the expression of melanin synthesis-associated proteins, such as microphthalmia-associated transcription factor (MITF), tyrosinase, tyrosinase-related protein-1 (TRP1), and TRP2. Based on our findings, we can conclude that 7H-4M has the ability to activate the melanogenesis process through the upregulation of cAMP-dependent protein kinase (PKA) and the cAMP response element-binding protein (CREB). Additionally, our study showed that 7H-4M induced melanogenic effects by downregulating the extracellular signal-regulated kinase (ERK) and the phosphatidylinositol 3 kinase (PI3K)/protein kinase B (Akt)/glycogen synthesis kinase-3β (GSK-3β) cascades, while upregulating the JNK and p38 signaling pathways. Finally, the potential of using 7H-4M in topical applications was tested through primary human skin irritation tests. During these tests, no adverse reactions were induced by 7H-4M. In summary, our results indicate that 7H-4M regulates melanogenesis through various signaling pathways such as GSK3β/β-catenin, AKT, PKA/CREB, and MAPK. These findings suggest that 7H-4M has the potential to prevent the development of pigmentation diseases.

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Section: Discussionmentioning

confidence: 99%

A 7-Hydroxy 4-Methylcoumarin Enhances Melanogenesis in B16-F10 Melanoma Cells

Kim

Hyun

2023

Molecules

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“…Extractions of leaves, branches, residues (separated into epicarp + mesocarp, and endocarp) and seeds of Dipteryx odorata and Dipteryx punctata have also been performed in a Soxhlet apparatus and, as in this study, the highest yields were obtained for extracts of fruit residues (epicarp + mesocarp) (44.1% and 54.2%) and for the seeds (48.9% and 44.5%) of the two species, respectively [10]. The yield of Dipteryx odorata seed extractions also resulted in values as high as 46.5% [34].…”

Section: Discussionmentioning

confidence: 65%

“…However, other species of the genus, such as Dipteryx punctata (S. F. Blake) Amshoff, can also be exploited to obtain coumarin and other plant products [10].…”

Section: Introductionmentioning

confidence: 99%

Phytochemical Analysis and Antioxidant Activity of Ethanolic Extracts from Different Parts of Dipteryx punctata (S. F. Blake) Amshoff

Sousa,

Gomes,

Viana

et al. 2023

Applied Sciences

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The genus Dipteryx, to which the cumaru tree belongs, contains neotropical species native to Central and South American countries. They are used both in the sale of timber and seeds and for the extraction of the active compound coumarin, used as a flavoring agent. This study evaluated the phytochemical profile and antioxidant activity of extracts of leaves, branches, and fruits (residues and seeds) of the species Dipteryx punctata. The plant material for analysis was collected in five seed-producing areas, in Mojuí dos Campos, Pará, Brazil. The extracts were obtained via Soxhlet extractor using 92.8% distilled ethanol as the solvent and operated till exhaustion (8 h). Chromatographic analyses were performed by thin-layer chromatography (TLC) and gas chromatography coupled to mass spectrometry (GC-MS), followed by phytochemical determination of phenolics and flavonoids and analysis of antioxidant activity (TLC and free radical scavenging 2,2-diphenyl-1-picrylhydrazyl (DPPH). The highest extract yields were obtained from D. punctata fruit residues and seeds from all areas, with maximum values of 26.1% and 47.2%, respectively, in Boa Fé (area 3). In the evaluation by TLC, the extracts of leaves, branches, and residues presented the classes of terpenes, condensed and hydrolysable tannins, and flavonoids; coumarin (1,2-benzopyrone) was identified only in residue and seed extracts. The major constituents highlighted in the collection areas were: lupeol in leaves (34.4% in area 5), 4-O-methylmannose in branches and residues (85.5% in area 2 and 90.6% in area 5, respectively), and coumarin in seeds (99.3% in area 3). The best results for the antioxidant action were obtained for extracts from leaves and residues, requiring a concentration of 117.6 µg.mL−1 of the extract from the leaves and 160.4 µg.mL−1 of the extract from the residues to reduce the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical by 50%. This phytochemical study contributes to reducing the scarcity of information on D. punctata. The chemical classes and compounds identified corroborate the antioxidant activity and add value to the species, and the data obtained reinforce the importance of reusing fruit residues, which are chemically rich but discarded in the environment.

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“…Part of the interest of producers is related to the possibility of multiple uses of the species and its growth potential in degraded areas [18,19]. Its use is extremely diverse; however, it stands out for containing an aromatic essential oil in its seeds that is widely used in the cosmetics, perfumery, and pharmaceutical industries [20], as well as showing potential for antifungal action [21]. In regard to the production of tonka beans, the state of Pará is responsible for a significant portion of it, with a production of 79 tons per year [1].…”

Section: Introductionmentioning

confidence: 99%

“…has been the subject of study in a large number of recent research projects. However, these studies are primarily concentrated on wood production in native forests [29,34] and the potential use of almonds and coumarin [21,35,36].…”

Section: Introductionmentioning

confidence: 99%

Dendrometric Relationships and Biomass in Commercial Plantations of Dipteryx spp. in the Eastern Amazon

de Sousa Lopes,

Pauletto,

Gomes

et al. 2023

Forests

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The objective of this study is to characterize and compare the relationships between dendrometric variables in Dipteryx spp. stands in the Western Amazon by fitting linear regression equations for total height (ht) and crown diameter (dc). Six forest stands were evaluated in three municipalities. The variables collected included diameter at 1.3 m height (dbh), ht, and dc. Simple and multiple linear regression equations were fitted to characterize the relationships between ht and dc. The aboveground biomass and carbon stock of the stands were estimated. Most dendrometric variables were positively correlated (97.5%). The general equations presented an R2adj. greater than 0.7, and all coefficients were significant. Equations with non-significant coefficients were common in settlement adjustments (45%). The error for these equations varied between 1.1 and 23.6 m. The trees averaged 22 t ha−1 of aboveground biomass in the stands. There was a variation in carbon sequestration potential among stands, ranging from 5.12 to 88.91 t CO2 ha−1. Single-input equations using dbh as an independent variable are recommended for estimating dc and ht for individual Dipteryx spp. stands. Stands in the Western Amazon play a significant role in carbon sequestration and accumulation. Trees can sequester an average of 4.8 tons of CO2 per year.

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Identification of Coumarins and Antimicrobial Potential of Ethanolic Extracts of Dipteryx odorata and Dipteryx punctata

Cited by 8 publications

References 36 publications

A 7-Hydroxy 4-Methylcoumarin Enhances Melanogenesis in B16-F10 Melanoma Cells

A 7-Hydroxy 4-Methylcoumarin Enhances Melanogenesis in B16-F10 Melanoma Cells

Phytochemical Analysis and Antioxidant Activity of Ethanolic Extracts from Different Parts of Dipteryx punctata (S. F. Blake) Amshoff

Dendrometric Relationships and Biomass in Commercial Plantations of Dipteryx spp. in the Eastern Amazon

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