Two New Protopines Argemexicaines A and B and the Anti-HIV Alkaloid 6-Acetonyldihydrochelerythrine from FormosanArgemone mexicana

Abstract

Two new protopine-type alkaloids, argemexicaine A (1) and argemexicaine B (2), along with thirteen known alkaloids, were isolated from MeOH extracts of Formosan Argemone mexicana L. (Papaveraceae). Physical and spectral analyses, particularly IR and thermo-modulated 1D and 2D NMR, were used to determine the transannular conformations of the isolated protopine-type alkaloids. The known benzo[ c]phenanthridine (+/-)-6-acetonyldihydrochelerythrine (5) exhibited significant anti-HIV activity in H9 lymphocytes with EC50 and TI (Therapeutic Index) values of 1.77 microg/mL and 14.6, respectively.

Synthesis, structure, antimycobacterial and anticancer evaluation of new pyrrolo-phenanthroline derivatives

“…Recently, compounds with phenathroline skeleton have been synthesized and biologically evaluated [11][12][13][14][15] as analogues of benzo[c]phenanthridine alkaloids (e.g. nitidine, fagaronine, sanguinarine) that attracted attention due to their interesting biological properties [16][17][18][19] . Compared to 1,10-phenanthroline that has been widely studied both for synthesis and applications, 4,7-phenanthroline received much less interest due to difficulties in its synthesis.…”

Isolation of functional total RNA from Argemone mexicana tissues

“…Most A. mexicana tissues contain high amounts of latex, which besides being rich in polysaccharides, represent a source of polyphenols (Chang et al 2003), that rapidly oxidize during grinding. This method produced a white, water soluble RNA precipitate with a significant yield (ca 150 µg per gram of fresh weight, (Table 1).…”

“…The absence of most polysaccharides, polyphenols and pigments in the RNA extracts from tissues of A. mexicana avoided interferences in two different methods employed for the detection of specific transcripts: northern blot ( Figure 2a) and semiquantitative RT-PCR (Figure 2b). Moreover, the method can also be applied to A. mexicana cell cultures, which also are rich in phenols and sugars (Chang et al 2003). This method was developed after unsuccessful attempts with other RNA isolation protocols for polysaccharide-rich tissues (Valenzuela-Avendaño et al 2005).…”

“…The occurrence of diverse alkaloids, flavonoids and fatty acids in its tissues may explain these properties (Shaukat et al 2002;Chang et al 2003). In fact, berberine and sanguinarine, two of the main alkaloids isolated from Argemone tisúes , display significant *Corresponding author cytotoxic and antimicrobial properties (Villinski et al 2003;Beuria et al 2005).…”

Zanthoxylum Genus as Potential Source of Bioactive Compounds

“…Representatives of these alkaloids have exhibited antimalarial (Nyangulu et al, 2005;Ross et al, 2004), antileukemic (Dupont et al, 2005), antioxidant (Pérez et al, 2003), nematicide (Matsuhashi et al, 2002), HIV (Chang et al, 2003), antibacterial (Gonzaga et al, 2003), antimicrobial (Nissanka et al, 2001) and antifungal activities (Queiroz et al, 2006), among others. Their distribution is very limited in plants, and only they have been isolated from some genera belonging to the families Papaveraceae, Rutaceae and Fumiraceae mainly, where they are considered chemotaxonomic markers.…”