Structural revision of clusianone and 7-epi-clusianone and anti-HIV activity of polyisoprenylated benzophenones

Piccinelli, Anna Lisa; Cuesta‐Rubio, Osmany; Chica, Mariano Barrios; Mahmood, Naheed; Pagano, Bruno; Pavone, Michele; Barone, Vincenzo; Rastrelli, Luca

doi:10.1016/j.tet.2005.06.030

Cited by 145 publications

(129 citation statements)

References 24 publications

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“…Out of sixteen extracts tested in an HIV-1 viral replication assay, two extracts (fruit extracts of G. semseii and G. livingstoneii) showed moderate to mild anti-HIV activities, respectively. The literature indicated that some polyisoprenylated benzophenone derivatives isolated from Clusia (Piccinelli et al, 2005) and Garcinia (Gustafson et al, 1992) genera exhibited potent anti-HIV-1 activities. Similar findings have been reported by Gustafson, et al, 1992 of the isolation of guttiferones, benzophenone compounds with anti-HIV activities from Garcinia plants.…”

Section: Discussionmentioning

confidence: 99%

Cytotoxic and anti-HIV activities of some Tanzanian Garcinia species

Magadula

Suleimani

2010

Tanzania J Hlth Res

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Cancer and HIV/AIDS remains the greatest public health and humanitarian challenges in the current world's health sector. For many decades now, millions of lives have been compromised by the two diseases. This study has evaluated ethanol extracts from nine Garcinia plant species collected in Tanzania for their in vitro cytotoxicity against four human cancer cell lines and for anti-HIV activity against HIV-1 viral replication in MT4 cells. Among the tested extracts, the fruit extracts of G. livingstoneii and G. semseii showed moderate to mild cytotoxic activities against A549, DU145, KB and Kbivin human cell lines with 50 % cytotoxic (CC50) values ranging from 5.7-20.0 μg/ml. Furthermore, only fruit extracts of G. livingstonei and G. semseii showed significant anti-HIV-1 activity with EC50 values of 2.25 ± 0.51 and 0.93 ± 0.67 μg/ml respectively. This study has shown the potential of the Garcinia extracts to be the source of possible lead compounds and anti-HIV drug candidates currently needed for the management of HIV/AIDS. Phytochemical screening indicated dominance of phenolic compounds in Garcinia species while isolation of active principles from active fractions will be further undertaken.

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Section: Discussionmentioning

confidence: 99%

Cytotoxic and anti-HIV activities of some Tanzanian Garcinia species

Magadula

Suleimani

2010

Tanzania J Hlth Res

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“…resin and propolis [19,22]. Besides antimicrobial activity, nemorosone exhibits activity as a free radical scavenger of the same order of magnitude as ␣-tocopherol [19], and has moderate anti-HIV activity [23]. It has also been demonstrated that it exerts a strong cytotoxic activity against a panel of tumor cell lines [19,24,25] showing IC 50 values comparable to those of doxorubicin [19].…”

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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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“…Chemical investigation of the hexane-soluble extract of the fruits and methanol-soluble extract of the leaves of G. preussii resulted in the isolation and characterization of eight known compounds garciniagifolone (1) (Shan et al, 2012), garcimultiflorone E (2) (Liu et al, 2010), garcinialiptone B (3) (Zhang et al, 2010), garcinol (4) (Krishnamurthy et al, 1981), 7-epi-clusianone (5) (Piccinelli et al, 2005), garcimangosone (6) (Huang et al, 2001), astragalin (7) (Nakabayashi, 1955) and eriodictyol (8) (Hussain & Waterman, 1982) (Figure 1). Each constituent was identified on the basis of its 1 H-NMR spectra and HR-MS analysis by comparison with the literature.…”

Section: Resultsmentioning

confidence: 99%

Isolation and biological activity of compounds fromGarcinia preussii

Messi

Lannang

et al. 2014

Pharmaceutical Biology

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Context: Plants of the genus Garcinia (Clusiaceae) are traditionally used to relieve stomachaches, toothaches, and as a chew stick. Objective: In order to determine which compounds were responsible for these activities, a phytochemical investigation of the fruits and leaves of Garcinia preussii Engl. was pursued. Materials and methods: Plants were extracted by solvents of various polarities. Compounds isolation was then carried out using chromatography methods (medium-and high-pressure liquid chromatography, open column and thin-layer chromatography). The isolated compounds were identified and characterized by using 1D and 2D NMR spectroscopies. The antioxidant activity was evaluated using DPPH , ABTS À , ALP, and ORAC assays. The antimicrobial activity was assayed against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Enterococcus faecalis by determining the minimum inhibitory concentration (MIC) value. The cytotoxic activity of most of the isolated compounds was evaluated on a small panel of human cancer cell lines (DU145, HeLa, HT-29, and A431) using the XTT method. Results: The phytochemical investigation of G. preussii led to the isolation of eight known compounds, six benzophenones and two flavonoids. These compounds were tested for their biological activities. 1, 2, 3, 4, 7 and 8 demonstrated a high free radical scavenging activity with ER 50 ranging from 0.1 to 0.7. The antimicrobial activity was shown only against Gram-positive bacteria for 1, 4, and 5. A moderate cytotoxic activity with IC 50 ranging from 7 to 50 mM was observed, except for 6 which was not active. Conclusion: These results appear to support some of the properties reported for Garcinia species.

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Structural revision of clusianone and 7-epi-clusianone and anti-HIV activity of polyisoprenylated benzophenones

Cited by 145 publications

References 24 publications

Cytotoxic and anti-HIV activities of some Tanzanian Garcinia species

Cytotoxic and anti-HIV activities of some Tanzanian Garcinia species

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

Isolation and biological activity of compounds fromGarcinia preussii

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