Bioactive Annonaceous Acetogenins from the Bark of Xylopia aromatica

Abstract

Bioactive Annonaceous acetogenins have been isolated from the EtOH extract of the bark of Xylopia aromatica by bioactivity-directed fractionation using lethality to brine shrimp. These acetogenins include xylopianin [1 , xylopiacin [2], and xylomaticin [3], which are three new mono-tetrahydrofuran ring type acetogenins, in addition to the known compounds, annomontacin, gigantetronenin, gigantetrocin A, and annonacin. Compounds 1 and 2 are unusual in having hydroxylation at C-8; 3 has the same functionalities as annonacin but with 37 carbons instead of 35 carbons. The structures were elucidated by spectral analysis of the parent compounds and/or simple chemical derivatives. These acetogenins showed cytotoxicities, comparable to adriamycin, against three human solid tumor cell lines.

Antimalarial activity of some Colombian medicinal plants

“…Bioactive annonaceous acetogenins, xylopine and xylomatenin, have been isolated from the bark of Xylopia aromatica; these acetogenins showed cytotoxicities, comparable to adriamycin, against human solid tumor cell lines (Colman-Saizarbitoria et al, 1994). Oxoaporphine alkaloids, oxophoebine and liriodenine, have been isolated from Xylopia aethiopica; both showed selective toxicity against DNA repair and recombination deficient mutants of the yeast Saccharomyces cerevisae (Harrigan et al, 1994).…”

Acetogenins from Annonaceae

“…Annona montana (seeds) (28); Goniothalamus giganteus (bark) (29); X y/opia aromatica (167) OH OH 34 10 threo trans threo C37H6S07; M = 624 mp = 34-36 °c (28), 70-72 °c (29) [IXJn = + 81 ° (c = 1, MeOH) (28), [ …”

Goniotriocin and (2,4-cis- and -trans)-Xylomaticinones, Bioactive Annonaceous Acetogenins from Goniothalamus giganteus

“…The existence of the three OH moieties was indicated by an IR hydroxyl absorption at 3454 cm -1 and three successive losses of H 2 O from the [MH] + in the CIMS. Furthermore, the13 C NMR spectrum of 2 showed three resonances due to oxygen-bearing carbons at δ 71.7, 73.97, and 74.04, indicating the existence of three secondary hydroxyls. The presence of a mono-THF ring, with two OH groups flanking the ring, was suggested by proton resonances at δ 3.41 (H-15 and H-20) and 3.80 (H-16 and H-19) and the carbon signals at δ 82.60 (H-16) and 82.66 (H-19)…”

“…Consequently, the structure of 2 is proposed as illustrated, and it was named (2,4-cis and -trans)-xylomaticinone, honoring the parent acetogenin, xylomaticin, 13 which has previously been found in Xylopia aromatica, 13 Asimina longifolia, 21 and Goniothalamus giganteus. 5 We, thus, suggest that xylomaticin, whose absolute stereochemistry has not been previously determined, 13 has the same absolute stereochemistry as that of (2,4-cis and -trans)-xylomaticinone (2) reported herein.…”

“…1): white, waxy solid (2 mg); [R] 23 D +10.0°( c 0.03, CHCl3); IR (film on NaCl plate) νmax 3378, 2925, 2853, 1750, 1718, 1458, 1066; 1 H,13 C NMR (CDCl3), seeTable 1;CIMS (isobutane) m/z 637 [MH] + (23),619 [MH -H2O] + (47), 601 [MH -2H2O] + (100), 583 [MH -3H2O] + (38); HRCIMS (isobutane) m/z 637.4672 for C37H65O8 [MH] + (calcd 637.4679); EIMS see Figure 2. (2,4-cis and trans)-Xylomaticinone (2): white, waxy solid (7 mg); [R] 23 D +26.2°(c 0.08, CHCl3); IR (film on NaCl plate) νmax 3454, 2916, 2848, 1756, 1716, 1470, 1070; 1 H, 13 C NMR (CDCl3), see Tables 2 and 3; CIMS (isobutane) m/z 625 [MH] + (100), 607 [MH -H2O] + (35), 589 [MH -2H2O] + (73), 571 [MH -3H2O] + (14); HRCIMS (isobutane) m/z 625.5061 for C37H69O7 [MH] + (calcd 625.5043); EIMS see Figure 3.…”