~ 80 ~ International Journal of Chemical Studies 2016; 4(5): 80-87 P-ISSN2349–8528 E-ISSN 2321–4902 IJCS 2016; 4(5): 80-87 © 2016 JEZS Received: 11-07-2016 Accepted: 12-08-2016 Gloria Ihuoma Ndukwe Department of Chemistry, Rivers State University of Science and Technology, Nkpolu- Oroworukwo P.M.B. 5080 Port Harcourt, Rivers State, Nigeria Chukwunonye Moses Ojinnaka Department of Pure & Industrial Chemistry, University of Port Harcourt, East/West Road P.M.B. 5323 Choba, Rivers State, Nigeria Adebola Omowumi Oyedeji Department of Chemical and Physical Sciences, Walter Sisulu University, Private Bag X1, Mthatha 5117 Eastern Cape, South Africa Correspondence Chukwunonye Moses Ojinnaka Department of Pure & Industrial Chemistry, University of Port Harcourt, East/West Road P.M.B. 5323 Choba, Rivers State, Nigeria Novel bioactive triterpenoid saponin from the fruits of Napoleonaea imperialis P. Beauv (Lecythidaceae) Gloria Ihuoma Ndukwe, Chukwunonye Moses Ojinnaka and Adebola Omowumi Oyedeji Abstract Napoleonaea imperialis P. Beauv (Lecythidaceae) is a medicinal plant commonly found in South-Eastern Nigeria. The ripe fruits were extracted and partitioned into hexane, chloroform, n-butanol and aqueous fractions. These fractions were earlier tested and shown to possess anti-bacterial activities. The chloroform extract was chromatographed and purified to give compounds 1-5 whose structures were elucidated using ir, 1 H and 13 C-nmr as methyl-1,3,5-triene-tricyclopentadecanoate (1); 5-methyl-5-toluyl- 3,4,6-trihydropyran-2-one (2, napoleonapyran-2-one); 4-ethoxy-bicyclodecylbenzoate (3); 3β-O-[β-D- glucopyranosyl(1→2)][β-D-glucopyranosyl(1→4)][β-D-glucopyranosyl]-16α,22α,24,28-tetrahydroxy- 21-β-O-angeloxyolean-12-ene-29-al (4, napoleon aside -B) and 3-O-[β-D-glucopyranosyl]-1,4–dimethyl- 2,4,5,10-tetrahydroxy–bicyclodecane (5). Keywords: Napoleonaea imperialis, Lecythidaceae, fruits, structure, napoleonapyran-2-one, napoleon aside-B 1. Introduction There are ten species in the genus, Napoleonaea [1] , but Napoleonaea imperialis and Napoleonaea vogelli are the most common species found in Southern Nigeria. The bark of Napoleonaea vogelli and Napoleonaea imperialis are used locally as cough medicine. The seed pulp of some species of Napoleonaea is eaten [2] . Different parts of Napoleonaea imperialis P. Beauv are used in traditional medicine for treatment of infectious diseases [3, 4] . The chemistry and pharmacology of different species of Napoleonaea have been reported [5-11] . In our previous studies, the fruits of Napoleonaea imperialis showed great potentials as a molluscicide [12] and anti-bacterial agent [13] . In continuation of our studies, we report the isolation and characterization of novel compounds from the extracts of Napoleonaea imperialis that were earlier shown to be bioactive [13] . 2. Experimental 2.1 General The n-butanol, deuterated chloroform, deuterated methanol and deuterated DMSO used for this work were analytical grade. All other solvents used were re-distilled. The NMR spectra were taken on Bruker 600 MHz and Bruker 400 MHz operating at 600.1 MHz and 400.22 MHz for proton and 150.89 MHz and 100.63 MHz for carbon 13 respectively. NMR of pure compounds were processed using Bruker software. All samples were run at 25 o C. NMR spectra were calibrated using solvent signals ( 13 C : CDCl3 77.23ppm, DMSO-d6(CD3SOCD3) 39.51ppm, 13 C : CD3OH 49.2ppm ) or a signal of the proton of the partly or non deuterated solvent ( 1 H : CHCl3 in CDCl3 δ7.24ppm, DMSO in DMSO-d6 δ2.50ppm, 1 H : CH3OH in CD3OD -3.31ppm, 4.78ppm) with tetramethylsilane as internal reference. Chemical shifts (δ) are expressed in ppm. Structural elucidation was based on the interpretation of 1 H, 13 C, DEPT 90°, DEPT 135°, 1 H- 1 H COSY, NOESY, 1 H- 13 C direct correlation (HSQC) and 1 H- 13 C long- range correlation (HMBC). Ultra violet (UV) spectra were recorded on Perkin Elmer Lambda 25 UV-Visible spectrophotometer. Fourier transform infrared (FT-IR) spectra were recorded on Perkin Elmer Spectrum FT-IR spectrophotometer. Analytical thin layer chromatography (TLC) was carried out on silica gel Merck F254 precoated plates. Detection was made under ultraviolet light at wavelength 254nm and by spraying reagent (anisaldehyde − sulphuric acid)