Novel cytotoxic polyprenylated xanthonoids from Garcinia gaudichaudii (Guttiferae)

Prenylated caged xanthones: Chemistry and biology

“…Most of them except for gaudichaudiic acid B, C showed potent activities with to all tested cell lines with the ED 50 value are mostly in range of 0.5-8.0 μg/mL (Cao et al, 1998a(Cao et al, , 1998b.…”

“…Compounds 53-59 were evaluated for cytotoxicity against a panel of several cancer cell lines (P388, WEHI1640, MOLT4, HePG2 and LL/2). Most of them showed potent activities to all tested cell lines except for gaudichaudiic acid B, C (Cao et al, 1998a(Cao et al, , 1998bWu et al, 2000). Moreover, gaudichaudiic acids F-I (68-71) (Xu et al, 2000), 7-isoprenylmorellic acid (72) (Wu et al, 2001), the polyprenylated heptacyclic xanthonoids, were reported from the bark of G. gaudichaudii (Figure 3).…”

“…Natural sources of prenylated caged xanthones. Plants Parts Caged xanthones G. morella (Figure 2) seeds desoxymorellin (1), morellin (2), morellinol (6), dihydroisomorellin (22), moreollin (25), isomoreollin (26) (Adawadkar et al, 1976;Bhat et al, 1964;Kartha et al, 1963;Rao, 1937;Subba et al, 1978) resin isomorellin (3), morellic acid (4), isomorellic acid (5) (Karanjgaonkar et al, 1966;) G. hanburyi (Figure 2) resin desoxymorellin (1), isomorellin (3), morellic acid (4), isomorellic acid (5), isomorellinol (7), morellin dimethyl acetal (8), gambogin (9), gambogic aldehyde (10), gambogic acid (11), epigambogic acid (12), isogambogic acid (13) (Asano et al, 1996;Feng et al, 2008;Han et al, 2006aHan et al, , 2006bHan et al, , 2006cLee & Chen, 2006;Lin et al, 1993;Ollis et al, 1965;Reutrakul et al, 2007;Tao et al, 2009;Wang et al, 2008a) fruits desoxymorellin (1), isomorellin (3), morellic acid (4), isomorellinol (7), gambogic acid (11), 8,8a-epoxymorellic acid (21), dihydroisomorellin (22), isomoreollin B (23), moreollic acid (27), hanburinone (33), forbesione (39), 2-isoprenylforbesione (desoxyqaudichaudione A) (40), desoxygambogenin (43) (Reutrakul et al, 2007;Sukpondma et al, 2005a) whole plant gambogic acid (11), neogambogic acid (35) (Lu et al, 1984) G. forbesii (Figure 2) branches forbesione (39) (Leong et al, 1996) G. gaudichaudii (Figure 3) leaves morellic acid (4), forbesione (39), gaudichaudiones A-H (53-60), gaudichaudiones I-J (61-62), gaudichaudiic acids A-E (63-67) (Cao et al, 1998a(Cao et al, , 1998bWu et al, 2000) barks gaudichaudiic acids F-I (68-71), 7-isoprenylmorellic acid (72) (Wu et al, 2001;Xu et al, 2000 Garcinia hanburyi has been reported as a rich source of cytotoxic caged xanthones. Its orange gum-resin from stem bark, gamboge, is used in Thai traditional medicine as a purgative and an anthelm...…”

Polyprenylated Phloroglucinols and Xanthones

“…This concept is exemplified by the structure of forbesione (125), a natural product isolated from Garcinia forbesii [75] and Garcinia hanburyi [76]. Specifically, prenylation at the C5 center of forbesione (gambogic acid numbering) gives access to the gaudichaudione scaffold [77], represented here by deoxygaudichaudione A (126) [78]. Alternatively, prenylation of 125 at C5 followed by cyclization with the pendant phenol gives access to the morellin scaffold, represented here by desoxymorellin (123) [79].…”

Antibacterial Caged-Tetraprenylated Xanthones from the Fruits of Garcinia hanburyi

“…Caged-polyprenylated xanthones have been isolated from several Garcinia species, e.g., G. bracteata, 3) G. gaudichaudii, [4][5][6][7] G. morella [8][9][10] and G. scortechinii. [11][12][13] Compounds of this type exhibited cytotoxic [2][3][4][5][6] and antibacterial 11,13) activities. During our search for antibacterial substances from Garcinia plants, we found that the crude methanol extract from the fruits of G. hanburyi exhibited a significant antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) with a minimum inhibition concentration (MIC) of 16 mg/ml.…”