Five novel naphthylisoquinoline alkaloids with growth inhibitory activities against human leukemia cells HL-60, K562 and U937 from stems and leaves of Ancistrocladus tectorius

Microsatellites facilitate species delimitation in Congolese Ancistrocladus (Ancistrocladaceae), a genus with pharmacologically potent naphthylisoquinoline alkaloids

“…Fungicidal and insecticidal activities (e.g., Bringmann & al., 1992;Grimm & al., 1992), but also antiviral (HIV) and anti-protozoal activities (Leishmania, Plasmodium) have been reported (see, e.g., Boyd & al., 1994;François & al., 1997;Hallock & al., 1997;Ponte-Sucre & al., 2007, Bringmann & al., 2013a. Recently, growth-inhibitory effects on human leukemia cells have been attributed to these compounds (Jiang & al., 2013). Consequently, Ancistrocladus has been the subject of a large number of chemical and pharmacological studies aimed at investigating the alkaloids in different species, with ongoing research effort in this field.…”

First Atroposelective Total Synthesis of Enantiomerically Pure Ancistrocladidine and Ancistrotectorine

“…Once again, the final product was identicali na ll respects to authentic ancistrotectorine (2)i solated from A. tectorius. [19,21]…”

“…5,1'-, [11][12][13] 7,1'-, [11,14,15] 5, 8'-, [11, 16, 17] and N,8'-coupled representatives [18] have already been synthesized in an atropisomerically pure form, whereast his has not yet been achieved for 7,3'coupled representatives, such as ancistrocladidine (1)o ra ncis-trotectorine (2,F igure 1), which occur in various Ancistrocladus species. [19][20][21] Morris' group [22] described the first synthesis of ancistrocladidine (1)b yu sing aP inhey-Barton ortho-arylation as the key step for the construction of the biaryl axis between the naphthalene unit and the isoquinolinem oiety,b ut atroposelectivity was not achievedi nt he CÀCb ond formation.M oreover,t he synthesis required the use of toxic lead and mercury reagents. Thus far,ancistrotectorine (2)h as not been synthesized.…”

Ancistrolikokines E–H and related 5,8′-coupled naphthylisoquinoline alkaloids from the Congolese lianaAncistrocladus likokowith antiausterity activities against PANC-1 human pancreatic cancer cells

“…Southeast Asian and East African Ancistrocladaceae typically produce 3S-congured and 6-oxygenated compounds (i.e., 'Ancistrocladaceae-type' alkaloids). 4,5,[16][17][18][30][31][32][33] The only other plant family that likewise produces naphthylisoquinolines, the West African Dioncophyllaceae, exclusively contains alkaloids with R-conguration at C-3, always lacking an oxygen function at C-6 (i.e., 'Dioncophyllaceae-type' alkaloids). 4,5,34 West African and some of the Central African Ancistrocladus plants produce both, typical Dioncophyllaceae-and Ancistrocladaceae-type alkaloids, and all possible hybrid forms thereof, 4,5,11,19 while 'Ancistrocladaceae/Dioncophyllaceae hybrid-type' alkaloids are frequently found in Central African species together with Ancistrocladaceae-type compounds.…”

“…4,5 These secondary metabolites are the rst natural polyketide-derived isoquinoline alkaloids since not only the naphthalene part, but also the isoquinoline moiety originates from acetate-malonate units. [6][7][8] Depending on their individual structures, they display pronounced antiplasmodial, [9][10][11][12] antitrypanosomal, 9,13,14 antileishmanial, 9,[14][15][16] antileukemic, [17][18][19] or anti-HIV activities. 20,21 Previous phytochemical investigations on the roots and leaves of A. likoko had led to the isolation of six naphthylisoquinoline alkaloids, 22,23 viz., korupensamine A (1a), the ancistrolikokines A-D (2-4 and 6), and ancistroealaine A (7), along with the biosynthetically related tetralone cis-isoshinanolone (8) (Fig.…”