Phenolic and Glycoside Compounds Obtained from Brucea antidysenterica

Phenolic and glycoside compounds have been isolated from berries of Brucea antidysenterica. Based on spectroscopic data (IR, 1H NMR, 13C NMR and MS), the structure of phenolic compound D1 was identified as: 3-(3-hydroxybutyl)phenol (C10H14O2) and glycoside compound B6 was identified as: ethyl 4-(3-(6-(tetrahydro3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yloxy)hexyl)phenyl)butanoate(C24H38O8).


Introduction
Almost 20 years ago the World Health Organization (WHO) estimated that 'In many countries, 80% or more of the population living in rural areas are cared for by traditional practitioners and birth attendants' [1].It has since revised its view, adopting a rather safer position, now stating: 'most of the population of most developing countries regularly uses traditional medicine.'[2].Natural products have a wide range of diversity of multi-dimensional chemical structures; in the meantime, the utility of natural products as biological function modifiers has also won considerable attention.Subsequently, they have been successfully employed in the discovery of new drugs and have exerted a far-reaching impact on chemicobiology [3][4][5].From the past century, the high structural diversity of natural products has been realized from the perspective of physical chemistry.Their efficacy is related to the complexity of their well-organized three dimensional chemical and steric properties, which offer many advantages in terms of efficiency and selectivity of molecular targets.As a successful example of drug development from natural products, artemisinin and its analogs are presently in wide use for the anti-malaria treatment.This shows how research using natural products has made a significant contribution in drug development [6,7].
Brucea is a genus of plant in the family Simaroubaceae, the family comprises medium sized family of about 25 genera and 120 species which are mainly small trees or shrubs, distributed widely in tropical America and West Africa [8].The fruits, leaves and roots of Brucea antidysenterica are mixed with small amount of water and applied to treat wound [9].Bruceantin (2) and analogues compounds are triterpenes of the quassinoid type isolated from the bark of the Ethiopian tree Brucea antidysenterica.They are capable of inducing an array of biological responses including anti-inflammatory effect with murine models [10].Bruceantin (2) shows marked amoebicidal activity in vitro in the colony assay.At concentration of 0.2 μg/ml and above, all of the parasites Entamoeba histolytica (the dysentery amoeba) are killed.At 0.1 μg/ml, few parasites survive at 48 h, and all of the parasites are killed after 72 h to 0.1 μg/ml [11].Brucea antidysenterica is one of the medicinal plants which are present at various geographical locations and their presumptive folklore used to prescribe for ascaris in the researcher areas.

Plant collection and identification
The berries of Brucea antidysenterica were collected from southern nations, nationalities, and peoples' region of Ethiopia from Humbo woreda, which is around 347.5 km, south of Addis Ababa.The plant was identified by botanist in the department of biology, Wolaita Sodo University.

Characterization of the compounds Characterization of compound D1
Compound D1 was obtained from methanol extract.Its molecular formula, C10H14O2 was determined by negative LC-MS.In the negative LC-MS spectrum, the quasi-molecular ion peak was at m/z 166.56 [M-H] -.In the IR (KBr) spectrum the absorption band at 3435 cm -1 due to hydroxyl group and strong absorption band at 2923 cm -1 due to saturated C-H stretching.

Characterization of compound B6
Compound B6 was obtained as a dark solid from ethyl acetate (EtOAc) extract.Its molecular formula, C24H38O8 was determined by negative LC-MS.In the negative LC-MS spectrum, the quasi-molecular ion peak was at m/z 455.06 [M-H] -.
In the IR (KBr) spectrum the strong absorption band at 2924 cm -1 is due to saturated C-H stretching and medium intensity band at 1466 cm -1 due to -CH2-bend.Strong absorption band at 1745 cm -1 shows ester group and absorption band at 1167 cm -1 due to C-O stretching.

Table 1 1
H NMR, 13 C NMR and DEPT-135 spectral data of D1 in DMSO-d6 Position

Table 2 1
H NMR, 13 C NMR and DEPT-135 spectral data of B6 in DMSO-d6 Position This work has demonstrated that the berries of Brucea antidysenterica are rich sources of different compounds and resulted in the isolation of phenolic compound it were identified as D1: 3-(3-hydroxybutyl) phenol and glycoside compound B6: ethyl 4-(3-(6-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2 yloxy) hexyl)phenyl) butanoate.The structures of the compounds were characterized on the basis of spectral data ( 1 H NMR, 13 C NMR, DEPT-135, IR and LC-MS) as well as comparison with the literature data.Based on TLC analysis the plant contains several polar chemical constituents which were not isolated in this study because of time constraints.It is possible to isolate more polar compounds using advanced chromatographic techniques.Therefore, much more phytochemical and biological study should be carried out on the plant in future.