The Alkaloids of Telitoxicum peruvianum

Abstract

The alkaloid fraction of the Amazonian species Telitoxicum peruvianum (Menispermaceae) was found to contain the known alkaloids norrufescine (1), lysicamine (6), and subsesseline (2) as well as the new alkaloids telitoxine (3), peruvianine (4), and telazoline (7). Structures are proposed for the new alkaloids on the basis of spectroscopic data.As part of a continuing study of the alkaloids of the family Menispermaceae, we have investigated a number of plants of the South American genus Abuta (1-3). We now wish to report the isolation of some of the alkaloid constituents of Telitoxicum peruvianum, a species of the related and hitherto unexamined Amazonian genus Telitoxicum (4, 5).The total tertiary alkaloids were partitioned into phenolic and nonphenolic bases by extraction with 5% sodium hydroxide. The phenolic alkaloid fraction afforded, after separation by column chromatography on silica gel, the two known alkaloids, norrufescine (1) (1) and subsesseline (2) (6), and the two new alkaloids telitoxine (3) and peruvianine (4).•0 MeO 1 2 Telitoxine (3) was obtained as yellow flakes, mp 273-275°. Its high resolution mass spectrum indicated the molecular composition C17H13NO3. The ultraviolet spectrum of telitoxine was similar to that of the azafluoranthene alkaloid, norrufescine. Its nmr spectrum revealed a substitution pattern slightly different from that of norrufescine. The singlet at 7.18 was assigned to the C-3 proton; the remainder of the spectrum consisted of two methoxyls ( 4.06 and 4.07), a pair of doublets (2 H, 6 Hz) at 8.50 and at 7.53, doublets at 7.82 (1 H, 7 = 9 Hz) and at 7.57 (1 H, 7 = 2 Hz), and a quartet at 6.92 (1 H, 7 = 9 Hz and 2 Hz). The small ortho coupling constant of 6 Hz is consistent with the assignment of the 8.50 and 7.53 signals to pyridine ring protons at C-2 and C-3, respectively. Based on spectral evidence, structure (3) was assigned to telitoxine, making it a hydroxy derivative of triclisine (5) isolated from Triclisia gilletti (Dewild) Staner (7).Peruvianine (4) crystallized from methanol as red orange prisms, mp 252-255°3 20

ChemInform Abstract: Aza‐Polycyclic Aromatic Hydrocarbons from Saruma henryi.

“…The 1 H-NMR spectra ( Table 1) displayed six aromatic H-atom signals (d(H) 7.48 (s), 8.53 (d, J ¼ 1.36), 8.08 (dd, J ¼ 7.84, 1.36), 8.13 (d, J ¼ 7.84), 8.67 (d, J ¼ 5.72), and 7.73 (d, J ¼ 5.72)), and two MeO Hatom signals (d(H) 4.06 (s) and 4.12 (s)). These 1 H-NMR data were similar to those of the known compound telitoxine [4] [5]. However, a discernible C¼O signal at d(C) 167.1 of compound 1 appeared, compared with telitoxine, in the 13 C-NMR spectrum.…”

“…Compound 1 was obtained as yellow crystals with a molecular formula C 18 H 13 NO 4 , deduced from HR-ESI-MS (m/z 308.0930 ([M þ H] þ , C 18 H 14 NO þ 4 ; calc. 308.0923)).…”

Alkaloids: Chemical and Biological Perspectives

“…. Telazoline (35a), one of the so far rare bases containing an oxidized aporphine ring system, is also present (376). The nonphenolic bases from the woody stems of T. glaziovii contain very small amounts of oxoaporphines as well as telazoline and the reddish orange teladiazoline.…”

Bioactive Nitrogenous Compounds from Acorus tatarinowii

“…In addition, nine known compounds were also isolated and characterized, i.e. tatarine A ( 1 ), telitoxine ( 3 ), trans‐N ‐feruloyltyramine ( 4 ), trans‐N ‐feruloyl‐3‐ O ‐methyldopamine ( 5 ), (‐)‐ N ‐( p ‐coumaroyl) octopamine ( 6 ), (‐)‐ trans‐N ‐feruloyloctopamine ( 7 ), (+)‐3‐(4‐hydroxy‐3‐methoxyphenyl)‐ N ‐ [2‐(4‐hydroxyphenyl)‐2‐methoxyethyl]acrylamide ( 8 ), cannabisin D ( 10 ), and cannabisin F ( 11 ) (Fig. ) .…”