Four compounds were isolated from the stem bark of Antiaris africana. One of them, a γ-lactone named antialactone (1a), is reported for the first time as a natural product. The structures were determined by comprehensive analyses of their 1D and 2D NMR spectra and EI MS data. The absolute configuration of antialactone acetate (1b) was established by TDDFT CD calculations and comparison with measured CD spectra. The remaining three known compounds were identified, by comparing their spectroscopic data with those reported in the literature, as lichenxanthone, β-sitosterol, and betulinic acid.
BerhautJ. (1979). Flore Illustrée du Sénégal, 402–405.
3.
OkogunIJ, SpiffAI, EkongDEU. (1976) Triterpenoids and betaines from the latex and bark of Antiaris africana. Phytochemistry, 15, 826–827.
4.
BissetNG. (1962) Cardiac glycosides. VI. Moraceae: the genus Antiaris. Planta Medica, 10, 143–151.
5.
WehrliW, SchindlerO, ReichsteinT. (1962) Glycosides and aglycons. CCXXXI. Glycosides from the latex of Antiaris toxicaria from Malaya as well as from Antiaris africana from Kenya. Isolations. Helvetica Chimica Acta, 45, 1183–1205
6.
OguraK, KayanoA, AkazomeM. (1997) Bulletin of the Chemical Society of Japan, 70, 3091–3101
7.
CrawfordTD. (2006) Ab initio calculation of molecular chiroptical properties. Theoretical Chemistry Accounts, 115, 227–245;
8.
DiedrichC, GrimmeS. (2003) Systematic investigation of modern quantum chemical methods to predict electronic circular dichroism spectra. Journal of Physical Chemistry A, 107, 2524–2539.
9.
HussainH, KrohnK, FlörkeU, SchulzB, DraegerS, PescitelliG, AntusS, KurtánT. (2007) Absolute configuration of globosuxanthone A and secondary metabolites from Microdiplodia sp. - A novel solid-state CD / TDDFT approach. European Journal of Organic Chemistry, 292–295 and references cited therein.
10.
GrossEKU, BurkeK. (2006) Basics in Time-Dependent Density Functional Theory, Springer: Berlin. p.1–13;
11.
RappoportD, FurcheF.Excited States and Photochemistry ibidem, p. 337–354.
12.
KlyneW, ScopesPM. (1973) The carboxyl and related chromophores in fundamental aspects and recent developments in optical rotatory dispersion and circular dichroism, CiardelliF, SalvadoriP. (Eds), Heyden, London. p. 126ff;
13.
BeechamAF, (1968) Circulat dichorism in lactones. Tetrahedron Letters, 9, 2355–2360.
14.
KurtánT, PescitelliG, SalvadoriP, KenézÁ, AntusS, IllyésT-Z, SzilágyiL, SzabóI. (2008) Circular dichroism of diglycosyl dichalcogenides in solution and solid-state. Chirality, DOI: 10.1002/chir.20458.
15.
JimenezC, MarcosM, VillaverdeMC, RigueraR, CastedoL, StermitzF. (1989) A chromone from Zanthoxylum species. Phytochemistry, 28, 1992–1993.
16.
RubinsteinI, GoadLJ, ClagueADH. (1976) A 220 MHz spectra of phytosterols. Phytochemistry, 15, 195–200.
Navarro-VázquezA, CobasJC, SardinaFJ, CasanuevaJ, DiezE. (2004) A graphical tool for the prediction of vicinal proton-proton 3JHH coupling constants. Journal of Chemical Information Modeling, 44, 1680–1685.
