Chemical Studies on the Annonaceae – VI. The Alkaloids of the Stem and Fruit of Monanthotaxis cauliflora¹

Abstract

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Aporphinoid Alkaloids, III

“…C20HnO,N 351.1105 13C-NMR: (26); also in CDCl3/MeOD (139); values for -, C-2 and C-6a are different between (26) and ( 139) 218 OXOPUTERINE C18Hu04N 305.0687 13C-NMR: (CDCl3/MeOD) (139) C-7 and/or C-4 Substituted Aporphines (76), Annona (69) (120), Desmos (119), Guatteria (75), Hexalobus (4), Mitrella (51), Monanthotaxis (225), Polyalthia (236), Uvaria (118), Xylopia) 122) Monimiaceae: Laurelia (215) (216) Rhamnaceae: Ziziphus (94) 4 N-METHYLASIMILOBINE C1SH1902N 281.1415 SOURCES: Annonaceae: Xylopia (70) Menispermaceae: Stephania ) 110) Papaveraceae: Papaver (52) (4), Polyalthia (236), Xylopia (70) (122) Menispermaceae: Chasmanthera (148) Monimiaceae: Laurelia (212) Rhamnaceae: Ziziphus (94) 6 NUCIFERINE C19H2102N 295.1571 SOURCES: Annonaceae: Monanthotaxis (225) Papaveraceae: Papaver (159) (224) 7 ANONAINE C17H1502N 265.1102 SOURCES: Annonaceae: Annona (69) (120) (165) (233), Desmos (119), Hexalobus (4), Mitrella (51), Monodora (201), Polyalthia (236), Xylopia (70) (122) Magnoliaceae: Magnolia (164) Menispermaceae: Chasmanthera (148) Monimaceae: Laurelia (212) (216) 8 ROEMERINE C18H1702N 279.1258 SOURCES: Annonaceae: Guatteria (8) Menispermaceae: Stephania (145) Papaveraceae: Papaver (73) (157) (159) (178)…”

Phenylbutane Derivatives as Main Constituents ofMonanthotaxis capeaEssential Oil

“…Finally, benzylacetone [9] has been mentioned as one of the main constituents (up to 18%) of the oil of Eucalyptus delegatensis, together with relatively high amounts of methyl cinnainate (29,30). The biosynthesis ofphenylbutanoid derivatives is never described in any of the many books dealing with the biogenesis of natural compounds (1,31,32).…”

“…The catalytic reduction of commercial benzylacetone [9] leads to the alcohol 7 whose acetylation gives 8.…”

Additional Alkaloids of Pachygone ovata

“…Isolation of norjuziphine.-Elution of column B with CHCl3-MeOH (95:5) gave a residue (100 mg) that was rechromatographed over silicic acid (20 g). Elution of this column with CHCl3-MeOH (98:2) afforded a colorless residue (35 mg) which on treatment with MeOH gave norjuziphine (20 mg) as colorless crystals, Rf0.34, mp 155-157°(MeOH), [cxJ23d + 12°(c 0.43, MeOH); uv, max (MeOH) 284 nm (sh) (log 3.22), 280(3.26) and 234(3.52); cd, [ ]288 +2,280. 36); ir, v max (KBr) 3260 cm-3010, 2930, 2830, 1612, 1590, 1515, 1490, 1435, 1380, 1340, 1240, 1170, 1160, 1100, 1045, 995, 955, 920, 850, 838, 805, 795, 788, and 750; pmr (MeOH-d4 + TMS), 3.82 (s, 3H, OCH3), 6.53 (d, 2H, J=8Hz, ArH), 6.72 (d, 1H, J=8Hz, ArH), 6.79 (d, lH,/=8Hz, ArH), and 7.09 (d, 2H,/=8Hz, ArH); ms, mlz 285 (<1%)(M+), 178(100), 163 (33) and 107 (10). The structure was confirmed via the preparation of the methiodide salt by the treatment of norjuziphine (15 mg) in Me2CO (10 ml) with methyl iodide (0.5 ml) under reflux fot 48 h. Evaporation of the solvent yielded a residue whose ir spectrum was identical with authentic 2-methyl-7-methoxy-8,4'-dihydroxy-l-benzyl-l,2,3,4-tetrahydroisoquinoline methiodide (oblongine methiodide) (38).…”

“…Stepholidine was first isolated from Stephania glabra (Menispermaceae) (8) in 1969 and subsequently from Papaver somniferum var. album (Papaveraceae) (9) and Monanthotaxis cauliflora (Annonaceae) (10).…”