Two anthrones and one oxanthrone from Picramnia teapensis

Rodrı́guez-Gamboa, Tatiana; Fernandes, João B.; Fo, Edson Rodrigues; Silva, Maria Fátima das Graças Fernandes da; Vieira, Paulo C.; C, Oscar Castro

doi:10.1016/s0031-9422(99)00023-0

Cited by 15 publications

(22 citation statements)

References 8 publications

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“…Fractions 19±23 yielded after crystallization uveoside (2; 20 mg), [a] D : ±3 (c 0.36, MeOH), R f 0.45 [5]. Fractions 24±30 were further chromatographed on a silica gel column (10 g) using C 6 H 6 /Me 2 CO (7 [7]. The MeOH extract (10 g) was chromatographed over a silica gel column (200 g) and eluted with CHCl 3 /MeOH (4 : 1).…”

Section: Methodsmentioning

confidence: 99%

Cytotoxic Anthraquinone Derivatives from Picramnia antidesma

Hernández‐Medel¹,

Pereda‐Miranda²

2002

Planta med

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Activity-guided investigation of crude extracts prepared from the root bark of Picramnia antidesma, a medicinal plant long used for the treatment of malaria in tropical areas of the Americas, when tested on KB cells led to the isolation of a new compound, 10-epi-uveoside, from a cytotoxic fraction containing a rich mixture of anthrone glycosides. The antiplasmodial activity proved to be a result of the high levels of cytotoxicity displayed by the anthraquinone derivatives and therefore infusions from this crude drug lack the selectivity index needed to be an effective antimalarial agent.

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Section: Methodsmentioning

confidence: 99%

Cytotoxic Anthraquinone Derivatives from Picramnia antidesma

Hernández‐Medel¹,

Pereda‐Miranda²

2002

Planta med

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“…We have previously described our findings on the chemical study of P. teapensis, a tree found in Central America 2,3 . The study of the ethyl acetate extract of the stem bark from this plant has led to the isolation and characterization of two C-glycosylated anthrones (picramniosides D, E); two C-glycosylated oxanthrones (mayoside and mayoside B); a C,O-diglycosylated anthrone (picramnioside F); a C,O-diglycosylated oxanthrone (mayoside C); two anthraquinone glycosides (1-O-b-Dglucopyranosyl emodin and 8-O-b-D-glucopyranosyl emodin) as well as emodin and umbelliferone 2,3 .…”

Section: Introductionmentioning

confidence: 91%

“…The study of the ethyl acetate extract of the stem bark from this plant has led to the isolation and characterization of two C-glycosylated anthrones (picramniosides D, E); two C-glycosylated oxanthrones (mayoside and mayoside B); a C,O-diglycosylated anthrone (picramnioside F); a C,O-diglycosylated oxanthrone (mayoside C); two anthraquinone glycosides (1-O-b-Dglucopyranosyl emodin and 8-O-b-D-glucopyranosyl emodin) as well as emodin and umbelliferone 2,3 . Some of them showed antifungal activity against Leucoagaricus gongylophorus the symbiotic fungus cultivated by the leafcutting ants Atta sexdens L 3 .…”

Section: Introductionmentioning

confidence: 99%

Triterpene benzoates from the bark of Picramnia teapensis (Simaroubaceae)

Rodrı́guez-Gamboa¹,

Fernandes²,

Filho³

et al. 2001

J. Braz. Chem. Soc.

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“…Picramnia species (Picramniaceae, previously Simaroubaceae) are commonly used in folk medicine to treat or prevent dermatosis, external ulcers (sores), and skin irritations [ 4 ]. Phytochemical investigation in some of these Picramnia species resulted in isolation of several metabolites [ 5 , 6 ], mainly triterpenes [ 7 – 9 ], anthrones and anthraquinone glycosides [ 10 – 14 ], and oxanthrones [ 10 – 12 , 15 ] with cytotoxic, antimicrobial, antifungal, or antiparasitic activities [ 16 – 18 ]. Picramnia gracilis Tul.…”

Section: Introductionmentioning

confidence: 99%

Antileishmanial Effect of 5,3′-Hydroxy-7,4′-dimethoxyflavanone ofPicramnia gracilisTul. (Picramniaceae) Fruit:In VitroandIn VivoStudies

Robledo

Cardona

Ligardo

et al. 2015

Advances in Pharmacological Sciences

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Species of Picramnia genus are used in folk medicine to treat or prevent skin disorders, but only few species have been studied for biological activity and chemical composition. P. gracilis Tul. is a native species from Central and South America and although its fruits are edible, phytochemical analysis or medicinal uses of this species are not known. In the search of candidates to antileishmanial drugs, this work aimed to evaluate the antileishmanial activity of P. gracilis Tul. in in vitro and in vivo studies. Only ethanolic extract of fruits showed leishmanicidal activity. The majoritarian metabolite was 5,3′-hydroxy-7,4′-dimethoxyflavanone ether that exhibited high activity against L. (V.) panamensis (EC50 17.0 + 2.8 mg/mL, 53.7 μM) and low toxicity on mammalian U-937 cells, with an index of selectivity >11.8. In vivo studies showed that the flavanone administered in solution (2 mg/kg/day) or cream (2%) induces clinical improvement and no toxicity in hamsters with CL. In conclusion, this is the first report about isolation of 5,3′-hydroxy-7,4′-dimethoxyflavanone of P. gracilis Tul. The leishmanicidal activity attributed to this flavanone is also reported for the first time. Finally, the in vitro and in vivo leishmanicidal activity reported here for 5,3′-hydroxy-7,4′-dimethoxyflavanone offers a greater prospect towards antileishmanial drug discovery and development.

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Two anthrones and one oxanthrone from Picramnia teapensis

Cited by 15 publications

References 8 publications

Cytotoxic Anthraquinone Derivatives from Picramnia antidesma

Cytotoxic Anthraquinone Derivatives from Picramnia antidesma

Triterpene benzoates from the bark of Picramnia teapensis (Simaroubaceae)

Antileishmanial Effect of 5,3′-Hydroxy-7,4′-dimethoxyflavanone ofPicramnia gracilisTul. (Picramniaceae) Fruit:In VitroandIn VivoStudies

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