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New flavone, and cytotoxicity activity of Rauia resinosa ethanolic extract and constituents
Abstract
The ethanolic extract from leaves of Rauia resinosa, Rutaceae, provided a new flavone, 5-hydroxy-5',6,7-trimethoxy-3',4'-methylenedioxyflavone (1), in addition to four known compounds: 3',4',5,5',7-pentamethoxyflavone (2), 5,7,8-trimethoxy-3'4'-methylenedioxyflavone (3), 3',4',5,7,8-pentamethoxyflavone (4) and β-sitosterol (5). The structures of all compounds were established on the basis of spectroscopic methods, mainly 1D and 2D NMR, UPLC-DAD-MS and UPLC-ESI-MS/MS, involving comparison with literature data. Cytotoxicity of leaves and stems extracts, their fractions and compounds (2), (3), (4) and (5) were evaluated against T24 (bladder carcinoma), TOV-21-G (ovarian adenocarcinoma) and HepG2 (liver carcinoma) cell lines.
RESUMO Revisão taxonômica das Rutaceae do Estado do Amazonas que conta com 16 gêneros e 29 espécies (inclusive 2 variedades), cujas características morfológicas externas são suficientemente distintas para permitir a separação intergenérica e interespecífica dos taxa estudados. Os gêneros que ocorrem na região são Adiscanthus, Cusparia, Decagonocorpus, Erythrochiton, Esenbeckia, Galipea, Hortia, Leptothyrsa, Mannieria, Myllanthus, Nycticalanthus, Raputia, Ravenia, Spathelia, Ticorea e Zanthoxylum. Como auxílio à classificação dos gêneros e dos espécies das Rutaceas do Estado do Amazonas são apresentadas oito chaves analíticas baseadas nos caracteres morfológicos das plantas estudadas. Ilustram o trabalho 40 fotografias das 29 espécies dos 16 gêneros e 16 figuras mostrando a distribuição geográfica dos taxa estudados.
The powder of root bark of Malva parviflora (Malvaceae) was successively extracted with petroleum ether (b.p. 60–80 °C), chloroform and ethanol. The chloroform extract showed antibacterial activity against Staphylococcus aureus and Escherichia coli, whereas the ethanolic extract showed antibacterial activity against only S. aureus. The chloroform extract, after column chromatographic separation on silica gel using petroleum ether:chloroform (3:1) as eluent, furnished 98 mg of white crystalline compound. The yield of the compound is 0.316 % (w/w). The compound has a melting point of 134–136 °C and the Rf value 0.56 in benzene:chloroform:acetone (1:15:1) on silica gel TLC. The compound was characterized as β-sitosterol by physical properties, chemical test, spectral analysis (FTIR, NMR and MS) and comparing the data obtained from the literature.
Recebido em 3/7/10; aceito em 29/9/10; publicado na web em 8/11/10 COUMARINS AND ALKALOIDS FROM Rauia resinosa (RUTACEAE). The genus Rauia, that is poorly chemically studied, belongs to the Rutaceae family. This family has been known to contain a large variety of secondary metabolites. Our phytochemical investigation of the stem and leaves of Rauia resinosa has led to the identification of the structurally related coumarins: murralongin (1), murrangatin (2), munomicrolin (3), murrangatin diacetate (4), umbelliferone (5), rauianin (6) and one novel coumarin: 3-ethylrauianin (7); the alkaloids: N-methyl-4-methoxy-2-quinolone (8), mirtopsine (9), dictamine (10), g-fagarine (11), skimmianine (12), Z-dimethylrhoifolinate (13), zantodioline (14), zantobungeanine (15), veprissine (16), one novel alkaloid 7-hydroxy-8-methoxy-N-methylflindersine (17) and 8-hydroxy-N-methylflindersine (18) that is described as a natural product for the first time, and a mixture of steroids: as sitosterol and stigmasterol.
Purpose: To evaluate the anti-cancer activity of Limonia acidissima Linn (Rutaceae) which has long
been used traditionally for various infectious and malignant diseases.
Methods: The fruit extract of Limonia acidissima Linn was obtained by macerating 3 times with
methanol and then concentrating it at reduced pressure. Bioassay of the extract was carried out to
assess the anticancer activity. Breast cancer cell lines, SKBR3 and MDA MB435, were used for in-vitro
cell proliferation, cell viability assay, and cell cycle analysis of the extract.
Results: Bioassay of the extract of Limonia acidissima Linn. showed that a fraction (fraction 3) of the
ethanol extract had anticancer activity against SKBR3 and MDA-MB435 human breast cancer cells. The
effective dose (ED50) of Limonia acidissima Linn. fraction 3 was 56.1 and 30.6 μg/ml for SKBR3 and
MDA-MB435, respectively. After 48 h of exposure, this fraction (100 μg/ml) significantly reduced cell
proliferation in both cancer cell lines. In MDA-MB435 cells, cell cycle analysis showed that fraction 3
induced the accumulation of cells in G2/M phase, but no significant change in cell cycle was detected in
SKBR3 cells.
Conclusion: The results indicate that the extract fraction could induce cell cycle arrest. However,
further investigation is needed to assess the molecular mechanisms of the anticancer activities of this
plant.
In an ethanolic extract of leaves of Ottonia corcovadensis (Piperaceae) were identified sixteen terpenoids of essential oil and the three flavonoids 3',4',5,5',7-pentamethoxyflavone (1), 3',4',5,7-tetramethoxyflavone (2) and 5-hydroxy-3',4',5',7-tetramethoxyflavone (3) and cafeic acid (4). Two amides (5 and 6) were isolated from an ethanolic extract of the roots. The structures were established by spectral analysis, meanly NMR (1D and 2D) and mass spectra. Extensive NMR analysis was also used to complete ¹H and 13C chemical shift assignments of the flavonoids and amides. The components of the essential oil were identified by computer library search, retention indices and visual interpretation of mass spectra.
From the peels of Citrus hassaku hOrt.ex tANAKA (Rutaceae), eight flavonoid aglycones were isolated and characterized as 4',5,6,7,8-pentamethoxyflavone (I), 3',4’,5,6,7,8-hexamethoxyflavone (II), 3,3',4’,5,6,7,8-heptamethoxyflavone (III), 3',4’,5,6,7-pentamethoxyflavone (IV), 4’,5,7-trimethoxyflavone (V), 3,3‘,4’,5,7,8-hexamethoxyflavone (VI), 4’,5,7,8-tetramethoxyflavone (VII) and 3/,4/,5,7,8-pentamethoxyflavone (VIII), based on spectral and chemical data. © 1989, The Pharmaceutical Society of Japan. All rights reserved.
Flavones have antioxidant, anti-proliferative, anti-tumor, anti-microbial, estrogenic, acetyl cholinesterase, anti-inflammatory activities and are also used in cancer, cardiovascular disease, neurodegenerative disorders etc. Due to the wide range of biological activities of flavones have generated interest among medicinal chemists. This review may provide an opportunity to scientists of medicinal chemistry discipline to design selective, optimize as well as poly-functional flavone derivatives for the treatment of multi-factorial diseases.
The chemical composition of the volatile oil of the fresh leaves of Murraya koenigii growing wild in Dehra Dun was analyzed by gas chromatography-mass spectrometry. Thirty-four compounds consisting of 97.4% of the oil were identified. The major constituents identified were α-pinene (51.7%), sabinene (10.5%), β-pinene (9.8%), β-caryophyllene (5.5%), limonene (5.4%), bornyl acetate (1.8%), terpinen-4-ol (1.3%), γ-terpinene (1.2%) and α-humulene (1.2%).
Twenty six compounds (coumarins, flavonoids and alkaloids) were evaluated for their ability to inhibit the growth of three human tumour cell lines: breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and melanoma (A375-C5). Three of them [3-hydroxyflavone (6), 2'-hydroxy-3,4,4',5,6'-pentamethoxychalcone (11), Siderin (20)] were very potent in inhibiting all human tumour cell lines tested. The structure / activity relationship is discussed.
A new coumarin rauianin (1) was isolated from Rauia resinosa (Rutaceae) and its structure was elucidated by NMR spectral analysis and X-ray diffraction.
Aqueous leachates and a CHCl3-MeOH (1:1) extract of roots of Stauranthus perforatus showed a significant phytotoxic effect on Amaranthus hypochondriacus and Echinochloa crus-galli. Bioassay-directed fractionation of the active organic extract led to the isolation and characterization of ten secondary metabolites, which included two pyranocoumarins [xanthyletin (1) and 3-(1',1'-dimethylallyl)-xanthyletin (2)], four furanocoumarins [chalepensin (3), ammirin (4), chalepin (5) and 2'-isopropyl-psoralene (6)], two lignans [asarinin (7) and fargesin (8)], one sesquiterpene [4,5-epoxi-beta-caryophyllene (9)], and one alkamide [pellitorine (10)]. From these compounds, 2'-isopropyl-psoralene (6) or anhydromarmesin, is reported for the first time as a natural product, whereas compounds 4-10 are now reported as being present in S. perforatus. Metabolites 1, 3-5 and 10 caused significant inhibition of radicle growth of A. hypochondriacus and E. crus-galli. Furthermore, in a greenhouse experiment the decomposition of the leaves and roots in the soil had a significant inhibitory effect on the growth of weeds. The allelopathic action of the decomposition of roots was evident up to the sixth week of the experiment. The effect of leaves was comparable to that of DPCA (dimethyl tetrachloroterephthalate), a commercial herbicide. Finally different concentrations of Stauranthus root powder were combined with maize kernels and used to feed corn weevil. The treatments resulted in high mortality of this insect.
As part of an ongoing study of the medicinal plants of the Yucatec Maya, Casimiroa tetrameria was investigated for its phytochemistry. From an ethyl acetate partition of an ethanol extract of the leaves, eight flavonoids and a furanocoumarin were isolated and characterised as 5,6,2',3',5,6'-hexamethoxyflavone, 5,6,2,3',6'-pentamethoxyflavone and 5-methoxy-8-(3"-hydroxymethyl-but-2"-enyloxy)-psoralen using a combination of H-1, C-13 NMR and NOESY spectroscopy. (c) 2004 Elsevier Ltd. All rights reserved.
Further Pyrano Flavones from Neoraputia alba
- C A Arruda
- P C Vieira
- B J Fernandes
- Da Silva