Nemorosone, the major constituent of floral resins of Clusia rosea

Cuesta‐Rubio, Osmany; Vélez-Castro, Hermán; Frontana‐Uribe, Bernardo A.; Cárdenas, Jorge

doi:10.1016/s0031-9422(00)00510-0

Cited by 100 publications

(109 citation statements)

References 9 publications

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“…Nemorosone (1) was extracted from the floral resin of C. rosea and isolated as previously reported [18]. It was identified by 1D-and 2D-NMR experiments [18], and its purity was verified by HPLC-DAD and HPLC-MS.…”

Section: Standards and Samplesmentioning

confidence: 97%

“…It was identified by 1D-and 2D-NMR experiments [18], and its purity was verified by HPLC-DAD and HPLC-MS. Compounds 2-7 were isolated from Cuban propolis samples and identified by spectroscopic methods as previously reported [29,30].…”

Section: Standards and Samplesmentioning

confidence: 99%

“…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.…”

mentioning

confidence: 99%

“…A number of oxidized derivatives of hyperforin and adhyperforin were identified by HPLC-MS analyses as their degradation products (furohyperforin isomers, furohyperforin hydroperoxide, furoadhyperforin isomers, furoadhyperforin hydroperoxide) [27]. The instability of PPBs that contain the enolizable 1,3-diketone system has also been suggested: organic or inorganic acids rapidly converted these compounds to the corresponding pyran ether derivatives [4,13,18]; besides, this reactivity has been hypothesized to be involved in polymerization reactions, which occur in propolis, responsible for the "waterproof" protection [15]. Recently, the chemical lability of nemorosone was observed by Tsukano et al [28] during its total synthesis.…”

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confidence: 99%

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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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Section: Standards and Samplesmentioning

confidence: 97%

Section: Standards and Samplesmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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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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“…The National Cancer Institute (USA), which considers that a pure compound is active when its IC50 is lower than 4 µg/ mL (Cordell et. al., 1993); nemorosone showed IC50 values lower than 3.6 µg/mL against several cancer cell lines (Cuesta-Rubio et al 2001).…”

Section: Introductionmentioning

confidence: 96%

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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Polyprenylated Phloroglucinols and Xanthones

Theodorakis

2011

Biomimetic Organic Synthesis

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Nemorosone, the major constituent of floral resins of Clusia rosea

Cited by 100 publications

References 9 publications

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

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

Assessment of estrogenic, mutagenic and antimutagenic activity of nemorosone

Polyprenylated Phloroglucinols and Xanthones

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