Ancistectorine D, a naphthylisoquinoline alkaloid with antiprotozoal and antileukemic activities, and further 5,8'- and 7,1'-linked metabolites from the Chinese liana Ancistrocladus tectorius

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.…”

“…22 It was therefore named ancistrolikokine A 2 . Alternately, the as yet unknown metabolite 13 might be addressed as the 8-O-methyl analog of the cooccurring ancistrocongoline A (18). 25 The second new compound within this series of ve Nmethylated naphthylisoquinoline alkaloids isolated from the twig extract of A. likoko corresponded to a molecular formula of C 26 H 31 NO 4 , according to HRESIMS.…”

“…It was the new 5 0 -O-methyl analog of 13, and (13), A 3 (14), C 2 (5), H 1 (15), and H 2 (16) was thus named ancistrolikokine A 3 (14). It could likewise be addressed as the 5 0 ,8-O,O-dimethyl analog of the co-occurring ancistrocongoline A (18). 25 HRESIMS analysis of the third of these ve N-methylated naphthylisoquinoline alkaloids gave the same molecular formula of C 26 H 31 NO 4 as determined for ancistrolikokine A 3 (14).…”

“…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.…”

“…Furthermore, ve new N-methylated naphthyltetrahydroisoquinoline alkaloids with a 5,8 0 -biaryl linkage were discovered in the twigs of A. likoko, named ancistrolikokines A 2 (13), A 3 (14), C 2 (5), H (15), and H 2 (16). As part of our ongoing studies on the antiproliferative potential of naphthylisoquinoline alkaloids towards cancer cell lines, 18,19,33 the new ancistrolikokines presented here, as well as related known, 20,25-29 but yet not investigated 5,8 0 -coupled alkaloids, were tested for their activities against PANC-1 human pancreatic cancer cells under nutrient-deprived conditions. Fig.…”