DIVERSITY OF THE DITERPENES IN THE LEAVES OF Xylopia laevigata (Annonaceae) AND THEIR CYTOTOXICITIES

Costa, Emmanoel V.; Sampaio, Marília Fernanda Chaves; Menezes, Leociley Rocha Alencar; Dutra, Lívia Macedo; Costa, Carlos Maurício de Castro; Pinheiro, Maria Lúcia B.; Silva, Felipe M. A. da; Soares, Milena Botelho Pereira; Bezerra, Daniel P.; Barison, Andersson; Koolen, Héctor H. F.

doi:10.21577/0100-4042.20170504

Cited by 3 publications

(1 citation statement)

References 21 publications

(38 reference statements)

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“…The previous phytochemical investigation with some species of Annonaceae led to the isolation and characterization of different classes of secondary metabolites, such as monoterpenes, diterpenes, triterpenes, lignans, flavonoids, asarone-derived phenylpropanoids, acetogenins and mainly typical isoquinoline-derived alkaloids [ 3 , 4 , 5 , 6 , 7 ]. Some of these secondary metabolites isolated from Annonaceae species exhibited important biological activities, such as anti-inflammatory and urease-inhibiting properties [ 8 , 9 ], trypanocidal [ 10 , 11 ], leishmanicidal [ 11 , 12 ], antimalarial [ 4 , 13 ], antimicrobial [ 4 , 14 , 15 ], antioxidant and antirheumatic actions [ 9 , 15 ] and, particularly, cytotoxic activity against different human tumor cell lines [ 4 , 6 , 11 , 16 , 17 , 18 , 19 , 20 , 21 ].…”

Section: Introductionmentioning

confidence: 99%

Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities

et al. 2021

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Diclinanona calycina R. E. Fries popularly known as “envira”, is a species of the Annonaceae family endemic to Brazil. In our ongoing search for bioactive compounds from Annonaceae Amazon plants, the bark of D. calycina was investigated by classical chromatography techniques that yielded thirteen compounds (alkaloids and flavonoids) described for the first time in D. calycina as well as in the genus Diclinanona. The structure of these isolated compounds were established by extensive analysis using 1D/2D-NMR spectroscopy in combination with MS. The isolated alkaloids were identified as belonging to the subclasses: simple isoquinoline, thalifoline (1); aporphine, anonaine (2); oxoaporphine, liriodenine (3); benzyltetrahydroisoquinolines, (S)-(+)-reticuline (4); dehydro-oxonorreticuline (3,4-dihydro-7-hydroxy-6-methoxy-1-isoquinolinyl)(3-hydroxy-4-methoxyphenyl)-methanone) (5); (+)-1S,2R-reticuline Nβ-oxide (6); and (+)-1S,2S-reticuline Nα-oxide (7); tetrahydroprotoberberine, coreximine (8); and pavine, bisnorargemonine (9). While the flavonoids belong to the benzylated dihydroflavones, isochamanetin (10), dichamanetin (11), and a mixture of uvarinol (12) and isouvarinol (13). Compound 5 is described for the first time in the literature as a natural product. The cytotoxic activity of the main isolated compounds was evaluated against cancer and non-cancerous cell lines. Among the tested compounds, the most promising results were found for the benzylated dihydroflavones dichamanetin (10), and the mixture of uvarinol (12) and isouvarinol (13), which presented moderate cytotoxic activity against the tested cancer cell lines (<20.0 µg·mL−1) and low cytotoxicity against the non-cancerous cell line MRC-5 (>25.0 µg·mL−1). Dichamanetin (11) showed cytotoxic activity against HL-60 and HCT116 with IC50 values of 15.78 µg·mL−1 (33.70 µmol·L−1) and 18.99 µg·mL−1 (40.56 µmol·L−1), respectively while the mixture of uvarinol (12) and isouvarinol (13) demonstrated cytotoxic activity against HL-60, with an IC50 value of 9.74 µg·mL−1, and HCT116, with an IC50 value of 17.31 µg·mL−1. These cytotoxic activities can be attributed to the presence of one or more hydroxybenzyl groups present in these molecules as well as the position in which these groups are linked. The cytotoxic activities of reticuline, anonaine and liriodenine have been previously established, with liriodenine being the most potent compound.

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Section: Introductionmentioning

confidence: 99%

Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities

et al. 2021

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Effect of applied standard wood machining fluid on colour and chemical composition of the machined wood surface

Chuchala,

Sommer,

Orlowski

et al. 2023

Eur. J. Wood Prod.

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Appropriate monitoring of wood machining processes is a key issue to ensure the expected quality of the processed wood, expected efficiency and minimize energy consumption of production processes. A new trend is the design of environmentally friendly machining fluids. In this paper, as a preliminary study in this field, the effect of applied standard wood machining fluid on changes in the colour and chemical composition of the machined wood surface is presented. Scots pine wood (Pinus sylvestris L.) was used for this research. Colour measurements were carried out based on the three-axis CIELab system test in time intervals and coefficients such as: colour chroma (Cab*), colour saturation (Sab*), colour hue (h°), and total colour changes (ΔE*). Changes in chemical composition were analysed on the Attenuated Total Reflectance Fourier Transform Infrared Spectroscopy (ATR FT-IR). The results confirmed that standard machining fluids cause a significant change in the colour of the treated pine surface, which decreases over time but is still present even after 24 h. For the spectral analysis, no chemical changes were observed between the machining fluid and the wood. However, the fluid particles remained in the wood after 24 h. In order to reduce the effect of the machining fluid on the colour of the wood, its composition should be changed to allow and/or accelerate the evaporation of their components from the treated wood surface.

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Larvicidal activity of diterpenes from Xylopia langsdorfiana St. Hilaire & Tulasne (Annonaceae) against Aedes aegypti linn. (diptera: culicidae)

Ribeiro-Júnior,

Souza da Silva,

Araújo-Júnior

et al. 2024

Natural Product Research

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DIVERSITY OF THE DITERPENES IN THE LEAVES OF Xylopia laevigata (Annonaceae) AND THEIR CYTOTOXICITIES

Cited by 3 publications

References 21 publications

Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities

Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities

Effect of applied standard wood machining fluid on colour and chemical composition of the machined wood surface

Larvicidal activity of diterpenes from Xylopia langsdorfiana St. Hilaire & Tulasne (Annonaceae) against Aedes aegypti linn. (diptera: culicidae)

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