Two polyisoprenylated benzophenones from the trunk latex of Clusia grandiflora (Clusiaceae)

Lokvam, John; Braddock, Joan F.; Reichardt, Paul B.; Clausen, Thomas P.

doi:10.1016/s0031-9422(00)00193-x

Cited by 69 publications

(48 citation statements)

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“…Xanthones were isolated from Tovomita species (Seo et al 1999, Marques et al 2000, Zhang et al 2002, polyisoprenylated benzophenones were isolated from Clusia sp. (Lokvam et al 2000, Porto et al 2000, anthraquinones with antiprotozoal activity were found in V. orientalis (Mbwambo et al 2004), and cytotoxic compounds were isolated from three species of Vismia (Hussein et al 2003). A lupane derivative was isolated from C. densifolia (Gunasekera et al 1983).…”

Section: Resultsmentioning

confidence: 99%

Antibacterial and cytotoxic activity of Brazilian plant extracts - Clusiaceae

Suffredini

Paciência

Nepomuceno

et al. 2006

Mem. Inst. Oswaldo Cruz

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Twelve extracts obtained from nine plants belonging to six different genera of Clusiaceae were analyzed against Gram-negative (Escherichia coli and Pseudomonas aeruginosa) and Gram-positive (Staphylococcus aureus and Enterococcus faecalis) bacteria using the microdilution broth assay. Tovomita aff. longifolia, T. brasiliensis, Clusia columnaris, Garcinia madruno, Haploclathra paniculata, and Caraipa grandifolia extracts showed significant results against the bacteria. The organic extract obtained from the leaves of T. aff. longifolia showed minimal inhibitory concentration (MIC) = 70 µg/ml and minimal bactericidal concentration (MBC) = 90 µg/ml against E. faecalis and the organic extract made with the stem of C. columnaris showed MIC = 180 µg/ml and MBC = 270 µg/ml against P. aeruginosa. None of the antibacterial extracts showed lethal activity against brine shrimp nauplii. On the other hand, both aqueous and organic extracts obtained from the aerial organs of Vismia guianensis that were cytotoxic to brine shrimp nauplii did not show a significant antibacterial activity in the assay.Key words: antibacterial -cytotoxicity -Clusiaceae -Amazon rain forest -Brazil Natural products are considered an important source of new antibacterial agents. Drugs derived from unmodified natural products or drugs semi-synthetically obtained from natural sources corresponded to 78% of the new drugs approved by the FDA between 1983 and 1994(Cragg et al. 1997). This evidence contributes to support and quantify the importance of screening natural products. Previous screening works were done with more than 700 Amazon rain forest plant extracts, and results can be seen elsewhere (Frana & Suffredini 2002, Suffredini et al. 2002a, b 2004, Nepomuceno et al. 2003.Less than 20% of the Angiospermae have been screened for biological activity, and taking the Brazilian rain forests in concern, not much has been done so far. Brazil is home to more than 20% of the world's biodiversity, and the Amazon rain forest concentrates 17% of the biodiversity found within the country (Wilson & Peter 1988). For this reason, our research team has been systematically studying the antibacterial activity of organic and aqueous plant extracts obtained from plants native to the rain forest against Gram-positive Staphylococcus aureus ATCC 29213 (Sau) and Enterococcus faecalis ATCC 29212 (Efae) and Gram-negative Pseudomonas aeruginosa ATCC 27853 (Psa) and Escherichia coli ATCC 25922 (Ecol) with the aim of discovering new natural product compounds that can be used as antibiotics. Twelve aqueous and organic extracts obtained from plants belonging to six different genera of Clusiaceae (Vismia, Garcinia, Haploclathra, Tovomita, Caraipa, and Clusia) were submitted to the determination of the minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) using the microdilution broth assay (Suffredini et al. 2004). The extracts were also tested against brine shrimp nauplii in order to evaluate their potential as cytotoxic agents and to determine if ...

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Section: Resultsmentioning

confidence: 99%

Antibacterial and cytotoxic activity of Brazilian plant extracts - Clusiaceae

Suffredini

Paciência

Nepomuceno

et al. 2006

Mem. Inst. Oswaldo Cruz

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“…Clusiaceae, syn. Guttiferae) species (Lokvam et al, 2000) and it is the major constituent of Clusia rosea Jacq. floral resins (CuestaRubio et al, 2001;Popolo et al, 2011) and brown Cuban propolis (Cuesta-Rubio et al, 2002;Cuesta-Rubio et al, 2007;Pardo-Andreu et al, 2011).…”

Section: Introductionmentioning

confidence: 99%

Assessment of estrogenic, mutagenic and antimutagenic activity of nemorosone

Camargo¹,

Varela²,

Oliveira³

et al. 2011

Rev. bras. farmacogn.

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Currently, a wide range of research involving natural products is focused on the discovery of new drugs in many different therapeutic areas. A great number of the synthetic compounds on the market were derived from natural products, especially plants. Nemorosone is the major constituent of the floral resin of Clusia rosea Jacq., Clusiaceae, and in Cuban propolis. In vitro studies have shown cytotoxic activity in this substance against various tumor cell lines, including those resistant to various cytotoxic drugs, whereas it has low cytotoxicity to non-tumoral cells. Therefore, in order to characterize the biological activity of nemorosone, a substance with potential antitumor activity, and in view of preclinical testing of the toxicity of drug candidate compounds, the main aim of this study was to determine the mutagenic and antimutagenic activity of nemorosone by the Ames test, using the strains TA97a, TA98, TA100 and TA102 of Salmonella typhimurium. Secondly, to characterize the estrogenic activity in an experimental recombinant yeast model (Recombinant Yeast Assay) mutagenic activity was observed at in any of the concentrations in any of the test strains. To evaluate the antimutagenic potential, direct and indirect mutagenic agents were used: 4 nitro-o-phenylenediamine (NPD), mitomycin C (MMC) and aflatoxin B1 (AFL). Nemorosone showed moderate antimutagenic activity (inhibition level 31%), in strain TA100 in the presence of AFL, and strong antimutagenic activity in TA102 against MMC (inhibition level 53%). Estrogenic activity was observed, with an EEq of 0.41±0.16 nM at various tested concentrations.

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“…Nemorosone (1), a PPB with a bicyclo-[3.3.1]-nonane-2,4,9-trione system of type A (benzoyl group at C1), [1] is found in resins and latex of Clusia species [15][16][17], and it is the major constituent of C. rosea floral resin [18] and brown Cuban propolis [19,20]. Propolis is a resinous substance produced by honeybees from plant sources and is used to protect the hive against microorganisms and insects.…”

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confidence: 99%

Fragmentation pathways of polycyclic polyisoprenylated benzophenones and degradation profile of nemorosone by multiple-stage tandem mass spectrometry

Piccinelli

Campone

Piaz

et al. 2009

J. Am. Soc. Mass Spectrom.

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Nemorosone is a polycyclic polyisoprenylated benzophenone (PPBs) with strong cytotoxic activity. It is the major constituent of Clusia rosea floral resin and brown Cuban propolis. Other PPBs found in Cuban propolis are oxidized and cyclized derivatives of nemorosone. The instability of PPBs carrying an enolizable 1,3-diketone system has been suggested, and the elucidation of this aspect is very fundamental for the evaluation of their biologic activity. Electrospray ionization multistage tandem mass spectrometry (ESI-MS n ) was employed to shed light on the origin of these derivatives of nemorosone and to define the stability of this natural product. For this purpose, we initially performed MS n experiments on seven related PPBs to obtain useful information for structural characterization of this class of compounds and to identify the degradation products of nemorosone. The proposed fragmentation pathways, supported by exact mass measurements, allowed the nature of side chains on the bicyclo core and the type and position of their modifications to be established. In a second part, the degradation profile of nemorosone under different conditions was investigated to assess the possible effects of isolation procedures, climatic, and storage conditions on its stability. Our results reveal that nemorosone undergoes rapid degradation in n-hexane and chloroform solutions. The degradation products, identified by HPLC-ESI/MS n and NMR, are identical to derivatives of nemorosone previously isolated from propolis and plants. Thus, these PPBs are artefacts formed predominantly during the extraction and purification procedures. (J Am Soc

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Two polyisoprenylated benzophenones from the trunk latex of Clusia grandiflora (Clusiaceae)

Cited by 69 publications

References 5 publications

Antibacterial and cytotoxic activity of Brazilian plant extracts - Clusiaceae

Antibacterial and cytotoxic activity of Brazilian plant extracts - Clusiaceae

Assessment of estrogenic, mutagenic and antimutagenic activity of nemorosone

Fragmentation pathways of polycyclic polyisoprenylated benzophenones and degradation profile of nemorosone by multiple-stage tandem mass spectrometry

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