Bioactive Benzophenones from Garcinia xanthochymus Fruits

Baggett, Scott; Protiva, Petr; Mazzola, Eugene P.; Yang, Hui; Ressler, Elizabeth T; Basile, Margaret; Weinstein, I. Bernard; Kennelly, Edward J.

doi:10.1021/np0497595

Cited by 137 publications

(125 citation statements)

References 39 publications

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“…A lupane derivative was isolated from C. densifolia (Gunasekera et al 1983). Xanthones (Mahabusakaram et al 2005) and benzophenones (Baggett et al 2005) were isolated from Garcinia species, and some of them showed antibacterial activity (Rukachaisirikul et al 2003). …”

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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“…5). Cell death resulting from xanthochymol treatment of C. albicans appeared to be similar to its caspase-dependent apoptotic effects in human cancer cells (15,16,29,39). Xanthochymol-treated biofilms showed externalization of PS and DNA cleavage, as evidenced by TUNEL fluorescence (Fig.…”

Section: Fig 4 Inhibition Of Biofilm Maturation By Garcinia Benzophenmentioning

confidence: 72%

“…Xanthochymol and garcinol are catechols, compounds containing a 1,2-benzenediol moiety ( Fig. 1) (12,14,15). Both garcinol and xanthochymol display biological activity against methicillin-resistant Staphylococcus aureus (MRSA) (16).…”

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confidence: 99%

“…Both garcinol and xanthochymol display biological activity against methicillin-resistant Staphylococcus aureus (MRSA) (16). These compounds can also induce apoptosis in numerous human cancer cell lines, including leukemia and breast, prostate, colon, and pancreatic cancer cell lines (15)(16)(17). Garcinol inhibits histone acetyltransferase (HAT) p300 and pCAF at micromolar concentrations (18).…”

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confidence: 99%

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Garcinia xanthochymus Benzophenones Promote Hyphal Apoptosis and Potentiate Activity of Fluconazole against Candida albicans Biofilms

Jackson

Yang

et al. 2015

Antimicrob Agents Chemother

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c Xanthochymol and garcinol, isoprenylated benzophenones purified from Garcinia xanthochymus fruits, showed multiple activities against Candida albicans biofilms. Both compounds effectively prevented emergence of fungal germ tubes and were also cytostatic, with MICs of 1 to 3 M. The compounds therefore inhibited development of hyphae and subsequent biofilm maturation. Xanthochymol treatment of developing and mature biofilms induced cell death. In early biofilm development, killing had the characteristics of apoptosis, including externalization of phosphatidyl serine and DNA fragmentation, as evidenced by terminal deoxynucleotidyltransferase-mediated dUTP-biotin nick end labeling (TUNEL) fluorescence. These activities resulted in failure of biofilm maturation and hyphal death in mature biofilms. In mature biofilms, xanthochymol and garcinol caused the death of biofilm hyphae, with 50% effective concentrations (EC 50 s) of 30 to 50 M. Additionally, xanthochymol-mediated killing was complementary with fluconazole against mature biofilms, reducing the fluconazole EC 50 from >1,024 g/ml to 13 g/ml. Therefore, xanthochymol has potential as an adjuvant for antifungal treatments as well as in studies of fungal apoptosis.

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“…Among those PPAPs, garcinol isolated from Garcinia indica or several other Garcinia plants was found to possess antibiotic and antitumor activities as well as anti-inflammatory and anticarcinogenic properties [4][5][6][7][8][9][10][11]. Other members of PPAPs like guttiferones A-E, xanthochymol and their analogues exhibit antibiotic, anti-HIV and cytotoxic activities [12][13][14]. In our laboratory, the continuous investigation on Garcinia species, including Garcinia xipshuanbannaensis [15], Garcinia kola [16], Garcinia lancilimba [17], Garcinia xanthochymus [18], Garcinia yunnanensis [19], Garcinia oblongifolia [20] and Garcinia hanburyi [21][22][23][24] has led to a series of reports on xanthones and PPAPs derivatives and their anticancer activities.…”

Section: Introductionmentioning

confidence: 99%