Naphthylisoquinoline alkaloids from Ancistrocladus cochinchinensis

The Lactone Concept: An Efficient Pathway to Axially Chiral Natural Products and Useful Reagents

“…148 Figure 11 shows just a selection of ten additional representatives synthesized by the method, with any desired configuration at centers and axes. 2,29,109,[154][155][156][157][158][159][160][161]36 $WURSRVHOHFWLYH 6\QWKHVLV RI 1LWURJHQ'H YRLG %LDU\O 1DWXUDO 3URGXFWV Figure 12 shows two examples of nitrogen-GHYRLG natural products nicely fitting into the lactone concept: mastigophorenes A (3-) and B (0-), dimeric sesquiterpenes from liverworts of the genus 0DVWLJRSKRUD. 17 They are accompanied by their monomer, herbertenediol (), and have a remarkable nerve-growth stimulating activity, 17 which makes them worth synthesizing Different from the naphthylisoquinoline alkaloids, 2,9 the mastigophorenes are constitutionally symmetric, so that it seemed tempting to likewise try a first synthesis of these biaryls just by oxidative biomimetic coupling of the monomer, herbertenediol (), even at the price of a possibly low stereoselectivity.…”

Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

“…These and more than 80 further naphthylisoquinoline alkaloids (1 12,113,[856][857][858][859][860][861][862][863][864][865][866] all have in common a 4,5-dioxy-2-methylnaphthalene 24 A (see Fig_ 77) and a 1, 3-dimethyl-8-oxy-or -6,8-dioxyisoquinoline (or -di-or -tetrahydroisoquinoline) moiety B, which may additionally be equipped with stereocenters. Typically, the Dioncophyllaceae plants produce naphthylisoquinolines with (R)-configuration at C-3, always lacking an oxygen function at C-6 (like e.g.…”

“…(863,(882)(883)(884)(885)(886). This results in a broad range of different atropisomerization barriersfrom rapidly rotating axes, e.g.…”

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

“…2) including two new 7-6′ coupled ones (1 and 2), two new 5-3′ coupled ones (3 and 4) and one new 7-8′ (5) coupled naphthylisoquinoline alkaloid were isolated from the CH 2 Cl 2 extract. Compounds 6-14 were identified as hamatine (6) [5], ancistrobertsonine B (7) [11], ancistrocladinine (8) [7], hamatinine (9) [7], ancistrotanzanine A (10) [8], ancistrotanzanine B (11) [8], ancistrotectoriline B (12) [6], 7-epi-ancistrobrevine D (13) [7], and ancistrotectorine (14) [9], by comparison with the published spectroscopic data. Herein, we present the isolation and structure elucidation of compounds 1-5, and the evaluation of the growth inhibitory activities against HL-60 [20], K562 [21], and U937 [22] cells of all the isolates.…”

“…Structurally, naphthylisoquinoline alkaloids can be sorted into different subtypes according to the location of biaryl axis between naphthyl and isoquinoline moieties. To date, the coupling modes of 5-1′ [5][6][7][8], 5-3′ [8], 5-8′ [3,4,6], 7-1′ [6][7][8]11], 7-3′ [2,9,15], 7-6′ [8,10], 7-8′ [1,2,4,17,18] and C-N [4] were reported, however, there is limited data of 5,3′ and 7,6′-coupled compounds (Fig. 1).…”