A New Biflavonoid from Calophyllum panciflorum with Antitumor-Promoting Activity

Abstract

A new biflavonoid named pancibiflavonol (1) was isolated from an EtOH extract of the stem bark of Calophyllum panciflorum, along with six known biflavonoids, and its structure was elucidated by spectroscopic methods. These biflavonoids all exhibited significant inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate-induced Epstein-Barr virus early antigen activation in Raji cells.

Cancer chemopreventive activity of the prenylated coumarin, umbelliprenin, in vivo

“…In earlier reports, anticancer activity was reported from some terpenoid coumarins obtained from Ferula species against human cancer cell lines (Barthomeuf et al, 2006;Shahverdi et al, 2006;Barthomeuf et al, 2008). The promising cancer chemopreventive activity of umbelliprenin could be mainly attributed to the presence of a prenyl moiety on the structure of the umbelliferone nucleus, which is hypothesized to play an important role in the antitumor activity of prenyl-containing xanthones, coumarins, cinnamylphenols, flavonoids, and phenylpropanoids as reported earlier (Ito et al, 1998(Ito et al, , 1999(Ito et al, , 2000Baba et al, 2002;Fraigui et al, 2002;Itoigawa et al, 2004). Moreover, some other prenyloxycoumarins, such as auraptene, collinin, and 7-isopentenyloxycoumarin have also been shown to possess significant cancer chemopreventive effects (Tanaka et al, 1997(Tanaka et al, , 1998a(Tanaka et al, , 1998bBaba et al, 2002;Kohno et al, 2006;Iranshahi et al, 2008).…”

Amentoflavone Inhibits UVB-Induced Matrix Metalloproteinase-1 Expression Through the Modulation of AP-1 Components in Normal Human Fibroblasts

“…Investigation of the phytochemical constituents of S. tamariscina revealed it to be a rich source of biflavonoids. Biflavonoids have a variety of biological activities, such as anti-inflammatory [3][4][5][6], mast cell histamine release inhibitory activity [7,8], anti-tumor, and phospholipase A2 inhibitory activity [9,10]. A previous report showed the action of amentoflavone on the inhibition of inducible nitric oxide synthase expression by suppressing NF-κB activation in macrophages [11].…”

Gênero Calophyllum: importância química e farmacológica

“…Nesta espécie predominam compostos como xantonas, cumarinas e triterpenóides, tanto nas folhas como os galhos, sendo os principais compostos isolados: cordatolide A, B, oblongulide, ácido cordato-oblôngico (42)(43)(44)(45), ácido isocordato-oblôngico, fridelina, canofilol e sitosterol 41,42 .…”

“…Da C. panciflorum algumas substâncias inéditas foram isoladas, incluindo 2 novos biflavonóides, denominados de pancibiflavonol (46) e garcinianina (47), juntamente com GB-2, GB-1, GB-2 A, GB-1A e GD-IV 43 .…”

“…As caledonixantonas E e F (52,53) foram efetivas contra os fungos A. fumigatus e C. albicans 17,44 . Em outro estudo com o extrato diclorometano das folhas, foram isoladas duas novas xantonas substituídas, denominadas de caledol e dicaledol, as quais apresentaram atividade antifúngica, especialmente contra A. fumigatus 43 . As xantonas caloxantona C, dimetilcalabaxantona, calothwaitesixantona, calozeyloxantona e dombakinaxantona, isoladas desta espécie, mostraram atividade antimalárica, sendo ainda mais potentes contra Plasmodium falciparum resistente à cloroquina, quando modificadas quimicamente pela trioxigenação e prenilação das xantonas, demonstrando a relação entre atividade antimalárica e estrutura química destes compostos 46 .…”