The guttiferones, HIV-inhibitory benzophenones from Symphonia globulifera, Garcinia livingstonei, Garcinia ovalifolia and Clusia rosea

Non-toxic melanin production inhibitors from Garcinia livingstonei (Clusiaceae)

“…Sordat-Diserens et al (1992b) isolated the xanthone dimer garcilivin A, which has since been shown to display trypanosomal activity against T. brucei brucei (Mbwambo et al, 2006). Bioassay-guided fractionation of the fruit has yielded the HIV-inhibitory tetraprenylated benzophenone guttiferone A (3) (Gustafson et al, 1992), and the biflavanoid ent-naringeninyl- which is moderately active against a Ghanaian CQS strain of P. falciparum (Mbwambo et al, 2006). Several tree species are used traditionally on the eastern seaboard of South Africa for the treatment of skin diseases and cosmetic purposes, such as for skin lightening, often under the Xhosa and Zulu name umemezi (Earle, 1976;Khan, 1996;Cocks & Dold, 2004;Momtaz et al, 2008).…”

“…Twelve known compounds, morelloflavone (1) (Li et al, 2002), morelloflavone-7"-sulphate (2) (Li et al, 2002), guttiferone A (3) (Gustafson et al, 1992), sargaol (2-geranyl-6-hydroxy-2,8-dimethylchromene) (4) (Numuta et al, 1992;Voutquenne et al, 1999), isojacareubin (5) (Helesbeux et al, 2004), 6-deoxyisojacareubin (6) (Ishiguro et al, 1993) and the common triterpenoids, betulin, betulin aldehyde, lupeol, lupenone, euphol and stigmasterol were isolated in this investigation The structures of the isolated compounds were established using NMR spectroscopy and mass spectrometry and by comparison against literature data as referenced above.…”

“…In addition to its HIV-inhibitory activity (Gustafson et al, 1992), guttiferone A (3) has also been shown to be a potent inhibitor of cholinesterase (Lenta et al, 2007) and glutathione transferase enzymes (Muleya et al, 2008), as well as exhibiting antioxidant (Ngouela et al, 2006), leishmanicidal (Lenta et al, 2007), antiplasmodial (Ngouela et al, 2006), trypanocidal (Abe et al, 2004), and cytotoxic (Williams et al, 2003) effects. The activity of morelloflavone (1) as an antiinflammatory (Gil et al, 1997;Castardo et al, 2008) and antioxidant (Sanz et al, 1994;Deachathai et al, 2005;Hutadilok-Towatana et al, 2007) are well-documented; it has also been found to be a potent tyrosinase inhibitor (Masuda et al, 2005), anti-HIV-1 (Lin et al, 1997), and anti-bacterial (Verdi et al, 2004) agent, and to have antimalarial (Ngouamegne et al, 2008) and analgesic (Luzzi et al, 1997) properties.…”

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

“…Secondary cyclizations involve the ␤-diketone and pendant olefinic groups affording adamantanes, homoadamantanes and dihydrofuran-or pyran-fused structures [1]. PPBs exhibit a wide variety of biological activities, the most interesting of which are cytoprotection against HIV-1 [2,3], antibacterial activity against methicillin-resistant Staphylococcus aureus [4 -6], antioxidant [7][8][9], and cytotoxic activity [9 -14].…”

Qualitative and quantitative analysis of polycyclic polyprenylated acylphloroglucinols from Garcinia species using ultra performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry

“…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.…”