Natural products from the medicinal plant Duguetia staudtii (Annonaceae)

Ngouonpe, Alain Wembe; Mbobda, Alexis Sylvain W.; Happi, Gervais Mouthé; Mbiantcha, Marius; Tatuedom, Ostend K.; Ali, Muhammad; Lateef, Mehreen; Tchouankeu, Jean Claude; Kouam, Siméon F.

doi:10.1016/j.bse.2018.12.015

Cited by 11 publications

(5 citation statements)

References 8 publications

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“…Antibiotics 2020, 9, x FOR PEER REVIEW 2 of 11 various parts of this plant are used to treat several human ailments [12,13]. Previous chemical studies reported various compounds such as lignans, alkaloids, styrens, triterpenes and flavonoids [10][11][12][13][14]. From the fresh apparently healthy bark of D. staudtii, four endophytic fungi strains were isolated, among which was a Simplicillium sp.…”

Section: Resultsmentioning

confidence: 99%

Simplicilones A and B Isolated from the Endophytic Fungus Simplicillium subtropicum SPC3

et al. 2020

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Two new tetracyclic polyketides with a spirocenter, simplicilones A (1) and B (2) were isolated from the broth-culture of the endophytic fungus Simplicilliumsubtropicum (SPC3) in the course of our screening for new bioactive secondary metabolites. This endophytoic fungus is naturally harboured in the fresh bark of the Cameroonian medicinal plant Duguetia staudtii (Engl. and Diels) Chatrou. The planar structures of the simplicilones were elucidated by MS and 1D as well as 2D NMR spectroscopic techniques. The relative configuration was assigned by NOESY experiments in conjunction with coupling constants; subsequently, the absolute configurations were assigned by the modified Mosher’s method. The compounds showed weak cytotoxic effects against the cell line KB3.1 (in vitro cytotoxicity (IC50) = 25 µg/mL for 1, 29 µg/mL for 2), but were inactive against the tested Gram-positive and Gram-negative bacteria as well as fungi.

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Section: Resultsmentioning

confidence: 99%

Simplicilones A and B Isolated from the Endophytic Fungus Simplicillium subtropicum SPC3

et al. 2020

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“…Para el extracto de AcOEt, los valores son similares en ambos ensayos; mientras que, en el extracto de alcaloides totales, uno no es confiable y por tanto la comparación entre los valores no es óptima (ver tabla 1). (Fuentes, 2020;da Silva et al, 2007;Cunha, 2009;Ngouonpe et al, 2019;Dantas et al, 2020;Nardelli et al, 2021).…”

Section: Resultsunclassified

Evaluación de la actividad antioxidante in vitro de extractos de duguetia vallicola j.f. Macbr. – Annonaceae

Fuentes¹,

Contreras²,

Angulo³

2022

RFCB

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Se evalúa la actividad antioxidante de los extractos etanólico, de acetato de etilo y de alcaloides totales de la madera de D. vallicola J.F. Macbr., frente a la capacidad atrapadora del radical libre 2,2-difenil-1-picrilhidrazilo (DPPH) y 2,2’-azino-bis-(3-etilbenztiazolin-6-sulfonato de amonio) (ABTS), y se identifican dos alcaloides por primera vez en esta especie. La fracción de alcaloides totales obtenida del extracto etanólico crudo, se fraccionó por cromatografía de columna sucesivas, usando fases móviles de diclorometano (DCM)/metanol (MeOH) desde 99:1 hasta 90:10, lo que condujo posteriormente a la identificación de los alcaloides con núcleo oxoaporfína, liriodenina (1) y lanuginosina (2), empleando técnicas de RMN mono y bidimensional. Por otra parte, se determinó que todos los extractos tuvieron actividad antioxidante frente a los dos radicales usados, siendo el extracto de EtOH el más eficaz frente al radical ABTS (IC50=7,19 μM) y el extracto de AcOEt frente al radical DPPH (IC50= 12,79 μM). Los resultados obtenidos en este estudio permiten considerar a esta planta como fuente promisoria de componentes químicos con potencial actividad antioxidante.

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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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Natural products from the medicinal plant Duguetia staudtii (Annonaceae)

Cited by 11 publications

References 8 publications

Simplicilones A and B Isolated from the Endophytic Fungus Simplicillium subtropicum SPC3

Simplicilones A and B Isolated from the Endophytic Fungus Simplicillium subtropicum SPC3

Evaluación de la actividad antioxidante in vitro de extractos de duguetia vallicola j.f. Macbr. – Annonaceae

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

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