Cytotoxic chalcones and antioxidants from the fruits of Syzygium samarangense (Wax Jambu)

Simirgiotis, Mario J.; Adachi, Seiji; To, Satoshi; Yang, Hui; Reynertson, Kurt A.; Basile, Margaret; Gil, Roberto R.; Weinstein, I. Bernard; Kennelly, Edward J.

doi:10.1016/j.foodchem.2007.08.086

Cited by 107 publications

(71 citation statements)

References 32 publications

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“…7 The compounds generally associated with this genus are flavonoids and triterpenoids, although chalcones 8 and tannins 9 are also present. Among the flavonoids, such as glycosides or aglycone, there is a predominance of polyhydroxylated flavanols.…”

Section: Introductionmentioning

confidence: 99%

Bioactive triterpenes and phenolics of leaves of Eugenia brasiliensis

Magina¹,

Dalmarco²,

Dalmarco³

et al. 2012

Quím. Nova

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Recebido em 10/10/11; aceito em 17/1/12; publicado na web em 15/5/12 A chemical investigation of Eugenia brasiliensis Lam. (Myrtaceae) leaves led to the isolation of a-amyrin and b-amyrin (in a mixture), betulin, 29-hydroxy-oleanolic acid, quercetin, catechin and gallocatechin. Herein, the identification of 29-hydroxy-oleanolic acid is reported for the first time in the Myrtaceae family. Moreover, in this study, the extract, fractions and six of the seven compounds were monitored for toxicity toward Artemia salina, antibacterial and acetylcholinesterase inhibitory activity. The crude ethanol extract of the leaves and fractions were found be active on A. salina toxicity bioassay.

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Section: Introductionmentioning

confidence: 99%

Bioactive triterpenes and phenolics of leaves of Eugenia brasiliensis

Magina¹,

Dalmarco²,

Dalmarco³

et al. 2012

Quím. Nova

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“…Chalconas O-metiladas apresentaram atividade contra linhagens de células tumorais humanas KB, KB-VCR e A-549. Outra investigação mostrou que muitas chalconas com metoxilas no anel A exibiram atividade por inibição da polimerização da tubulina contra uma variedade de células tumorais com baixas concentrações (CI 50 < 50 mM) 28 . Os compostos 1 e 2 possuem nas posições 2' e 4' um grupo hidroxila e na posição 6' um grupamento metoxila.…”

Section: Resultsunclassified

Avaliação das atividades antiproliferativa e antioxidante em frutos de Campomanesia pubescens

Cardoso

Salvador

Carvalho

et al. 2014

Rev. Inst. Adolfo Lutz

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Avaliação das atividades antiproliferativa e antioxidante em frutos de Campomanesia pubescensEvaluation of antioxidant and antiproliferative activities in fruits of Campomanesia pubescens RESUMO A investigação química dos extratos bioativos dos frutos de Campomanesia pubescens (Myrtaceae) resultou no isolamento de duas chalconas. Os compostos isolados foram identificados pelas análises espectroscópicas ( 1 H, 13C e 2D RMN) e, por comparação com os dados descritos na literatura. A capacidade antioxidante dos extratos e frações foi determinada utilizando-se os ensaios de capacidade de absorção de oxigênio radical (ORAC-FL) e de DPPH; e os teores de fenólicos solúveis foram medidos utilizando-se o reagente de Folin-Ciocalteau. Os efeitos antiproliferativos dos extratos e de isolados de chalconas 1 e 2 foram determinados in vitro contra as seguintes células cancerosas humanas U251 (glioma), UACC-62 (melanoma), MCF-7 (mama), NC1-ADR/RES (ovário resistente), 786,0 (rim), NCI-H460 (pulmão), PC-3 (próstata), OVCAR-3 (ovário), HT-29 (cólon) e K562 (leucemia), e contra linhagem celular não cancerígena VERO. O extrato hexânico e os compostos isolados de chalconas 1 e 2 demonstraram efeito antiproliferativo potente contra linhagens de células cancerosas com valores de inibição de crescimento total (TGI) menores dos aqueles observados na linhagem celular controle. A atividade mais elevada das chalconas 1 e 2 foi detectada nas células MCF-7, PC-3 e HT-29. Palavras-chave. guavira, Campomanesia pubescens, DPPH, antiproliferativa, chalconas. ABSTRACTChemical investigation on the bioactive extracts from fruits of Campomanesia pubescens (Myrtaceae) resulted in the isolation of two chalcones. The isolated compounds were identified by means of spectroscopic analysis ( 1 H, 13C and 2D NMR), and by comparing with the data reported in the specific literature. Antioxidant capacity of extracts and fractions was determined using the oxygen radical absorbance capacity (ORAC-FL) and DPPH assays; and the total soluble phenolic contents were measured by using Folin-Ciocalteau reagent. The anti-proliferative effects of the extracts and of the chalcone isolates 1 and 2 were determined in vitro against human cancer cells lineages U251 (glioma), UACC-62 (melanoma), MCF-7 (breast), NC1-ADR/RES (ovarian-resistant), 786.0 (kidney), NCI-H460 (lung), PC-3 (prostate), OVCAR-3 (ovarian), HT-29 (colon) and K562 (leukemia), and against non-cancerous cell line VERO. Hexanic extract and chalcone isolated compounds 1 and 2 showed potent antiproliferative effect against cancer cell lineages with lower total growth inhibition (TGI) values than those found in control cell line. The highest activity of the chalcones 1 and 2 was observed against the MCF-7, PC-3 and HT-29 cell lines.

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“…It caused G1 phase cell cycle arrest and led to inhibition of phosphorylation of cell cycle regulatory proteins (Rao et al 2010a). Three chalcones, isolated from Syzygium samarangense, compounds 125, 110 (stercurensin) and 5 (cardamonin), displayed cytotoxic activity (with IC 50 of 10, 35 and 35 lM, respectively) against SW-480 human colon cancer cell line (Simirgiotis et al 2008). Flavokawain B (7), a chalcone from Alpinia pricei, significantly inhibited the growth of colon cancer cells.…”

Section: Antiprotozoal Propertiesmentioning

confidence: 99%

Naturally occurring chalcones and their biological activities

2014

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The aim of this review is to summarize the various naturally occurring chalcone compounds which have been isolated from different plants. Chalcones considered as obligate intermediated in flavonoid biosynthesis but they do not accumulate to appreciable degree in most plants. The largest number of natural chalcones has been isolated from species of the Leguminosae, Asteraceae and Moraceae families. Chalcone accumulating plants have often been used in traditional medicine and chalcones have therefore been studied and reported to possess many beneficial biological effects including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and chemopreventive activities. Previously published reviews on this topic survey the biological activities of natural and synthetic chalcones but there are no comprehensive contributions on occurrence and biological activities of natural chalcones. The present study provides an overview of hydroxy or/and methoxy-substituted chalcones, methylated, prenylated, geranylated and other monomeric derivatives, chromeno-and furanochalcones, dimeric chalcones and dihydrochalcone derivatives focusing on their biosynthesis, natural sources and biological activities. On the basis of 608 references, this review covers the phytochemistry and biological activity of natural chalcones, describing 646 compounds have been appeared in the literature since 1975. The summary is aimed to initiate further pharmacobotanical, biotechnological and medicinal studies on the field of chalcone research.

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Cytotoxic chalcones and antioxidants from the fruits of Syzygium samarangense (Wax Jambu)

Cited by 107 publications

References 32 publications

Bioactive triterpenes and phenolics of leaves of Eugenia brasiliensis

Bioactive triterpenes and phenolics of leaves of Eugenia brasiliensis

Avaliação das atividades antiproliferativa e antioxidante em frutos de Campomanesia pubescens

Naturally occurring chalcones and their biological activities

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