Department of Chemistry

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Browsing Department of Chemistry by Author "Nkeh-Chungag, B.N."

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    Biological Evaluation and Semi-synthesis of Isolated Compounds from (Syzygium aromaticum (L.) Merr. & Perry) Buds.
    (University of Fort Hare, 2014) Rali, Sibusiso; Oyedeji, O.O.; Nkeh-Chungag, B.N.
    Natural products play a fundamental role in modern drug discovery as they continue providing diverse bioactive lead compounds for new drug formulation. However, isolation of these valued compounds is problematic. On the other hand, the morbidity and mortality rates caused by non-communicable diseases are increasing with improved longevity. Thus, the study herein focused on the isolation of plant-derived compounds from Syzygium aromaticum and evaluated their biological properties. Syzygium aromaticum is a well-known plant which belongs to family Myrtaceae. Dried flower buds of S. aromaticum were subjected to sequential solvent extraction. The ethyl acetate extract (15.535 g) was subjected to column chromatography using a silica gel (0.063-0.200 mm) for isolation. This has led to the isolation of three distinct compounds that were identified as eugenol, maslinic acid (MA) and oleanolic acid (OA). The structural elucidation of these valued compounds was done using NMR, GC-MS, LC-MS, FT-IR and Mp. Further semi-synthesis of the oleanolic acid afforded acetate and ester OA-derived compounds with better solubility properties. All these compounds were evaluated for analgesic and anti-inflammatory properties. All tested compounds were administered at a dose of 40 mg/kg to both Wistar rats and Swiss mice. Significant (p<0.01) analgesic and anti-inflammatory properties are obtained for all compounds. The effects of eugenol in all experiment were better except in the thermal-induced pain or tail flick test. In the case of modified compounds, the formalin induced pain test disclosed that oleanane derived compounds confessed analgesic and anti-inflammatory effects better than OA, whereas, in tale flick test oleanolic acid proved superior analgesic effects compared to all its derivatives with the exception of the acetyl- derivative. Acute anti-inflammatory test showed that acetyl-derivatives were more active than other compounds. In conclusion, chromatographic techniques and semi-synthesise of oleanolic acid have resulted to several plant-derived compounds with analgesic and anti-inflammatory properties. The semi-synthesized compounds may serve as alternative drug candidates for new analgesic and anti-inflammatory drug formulation derivative. Acute anti-inflammatory test showed that acetyl-derivatives were more active than other compounds. In conclusion, chromatographic techniques and semi-synthesise of oleanolic acid have resulted to several plant-derived compounds with analgesic and anti-inflammatory properties. The semi-synthesized compounds may serve as alternative drug candidates for new analgesic and anti-inflammatory drug formulation.
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    Chemical Constituents and Biological Studies of Tagetes minuta L. and Rauvolfia caffra Sond.
    (University of Fort Hare, 2015) Mlala, Sithenkosi; Oyedeji, O.O.; Nkeh-Chungag, B.N.
    Green plants synthesize and store a variety of biochemical compounds some of which are extractable as raw material and can be used for various scientific investigations. Different plant parts have different effects as they often contain different active chemical components. Consequently, specific parts or the whole plant can be used for various treatments. The aim of this study was to extract, isolate and characterize the biologically active volatile and non-volatile compounds from Tagetes minuta and Rauvolfia caffra respectively. Tagetes minuta plant was considered for extraction of essential oils using hydrodistillation method. Cis-β-ocimene (38.03%), caryophyllene oxide (18.04%), alloocimene (25.35 %), isopropyl tetradecanoate (17.02 %), cis-ocimene (38.14%) and trans-β-ocimene (37.03%) were the major components of essential oil analyzed from fresh stem, dried stem, fresh leaf, dried leaf, fresh flower and dried flower respectively. The volatile compounds were identified by Gas Chromatography-Mass Spectrometry (GC-MS) and Gas Chromatography (GC). Essential oil of dried stem leaf and flower parts of T. minuta exhibit antioxidant activity as demonstrated by the DPPH and FRAP bioassays. Crude extracts were extracted from R. caffra stem bark using sequence of solvents namely n-hexane, dichloromethane, ethyl acetate, methanol and ethanol. A white powder, a β-sitosterol (non-volatile compound) was isolated by column chromatography from ethyl acetate fractions of R. caffra stem bark and identified on various spectroscopic techniques such as FTIR and (1D and 2D) NMR. Melting point was also determined to be a sharp 129-130 ºC. DCM, EA, MetOH and EtOH fractions as well as β-Sitosterol (compound SM/01), showed antioxidant activity when tested on DPPH, FRAP, total phenolic and flavonoid bioassays. This antioxidant activity might be due to the presence of hydroxyl groups in the compound and crude fractions. On the other hand, T. minuta’s essential oil showed high antioxidant activity when evaluated on the DPPH and FRAP bioassays, which can be attributed to the presence of oxygenated monoterpenes and sesquiterpenes known to act as free radical scavenging and reducing agents. The use of R. caffra stem bark extracts against hypertension and other diseases by traditional healers could be attributed to the presence of phytochemicals (polyphenols and flavonoids) with known health benefits. Thus, it is recommended that the plant should be exploited further using modern techniques involving separation and purification of compounds that can be used for drug formulation. This study supports the use of T. minuta and R. caffra as the potential natural antioxidant source to manage various diseases including hypertension.