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1 Chemical Composition and Anti-Microbial Activity of the Volatile J. Chem Soc. Nigeria, Vol. 43, No. 2, pp 141 - 150 [2018] CHEMICAL COMPOSITION AND ANTI-MICROBIAL ACTIVITY OF THE VOLATILE OILS OF AVERRHOA CARAMBOLA L. (STAR FRUIT) GROWN IN NIGERIA *G. I. Ndukwe and J. O. Okhiku Department of Chemistry, Rivers State University, Nkpolu-Oroworukwo, Port Harcourt, Rivers State, Nigeria. *Corresponding author: [email protected] Received 22 September 2017; accepted 18 December 2017, published online 25 March 2018 Abstract The chemical composition and antimicrobial activity of the essential oils extracted from the leaf and fruit of Averrhoa carambola L. (family Oxalidaceae) grown in Nigeria were evaluated. These extractions were carried out via hydrodistillation using a Clevenger apparatus. Essential oils from the leaf and fruit were analyzed using gas chromatography-mass spectrometry. The essential oil of the fruit revealed the presence of seventeen components, whose major compounds were estragole (62.312 %), trans-α- bisabolene (12.209 %) and pinene (8.246 %). Seven components from the essential oil of the leaf were identified; the major compounds were estragole (66.847 %), bis(2-ethylhexyl) phthalate (11.964 %) and α-ocimene (9.699 %). The volatile oil from the fruit showed antimicrobial activity against the test organisms (Escherichia coli, Bacillus subtilis, and Staphylococcus aureus) with minimum inhibitory concentrations ranging from 10 to 20 μg/ml; while that of the leaf inhibited the growth of only Staphylococcus aureus with minimum inhibitory concentration of 20 μg/ml. These results show that the plant, Averrhoa carambola, is a good antimicrobial agent. Keywords: Averrhoa carambola, volatile oil, hydrodistilation, antimicrobial activity, estragole, pinene, α-ocimene, star fruit Introduction leaves, for treating boils, colds, gastroenteritis, Plant extracts and volatile oils have been used postpartum edema, and traumatic injury [2]. for many purposes for centuries. The Phytochemical analysis of Averrhoa carambola antimicrobial activity of plant oils and extracts fruit indicated the presence of saponins, has been the basis of its several applications in alkaloids, flavonoids, tannins [3], antioxidants food preservation, processing, pharmaceuticals, such as polyphenoloxidase, proanthocyanidins, alternative medicine and natural therapies [1]. epicatechin and vitamin C [4], O-glycosyl Averrhoa carambola L. (Oxalidaceae) popularly flavonoid components such as quercetin-3-O-β- known as Star fruit is found in America, Brazil, d-glucoside and rutin [5]. Other compounds Australia, South-East Asia and some parts of isolated from Averrhoa carambola include; β- Africa including Southern Nigeria. The sitosterol, lupeol, anthraquinone, cyanidin-3-0- carambola tree is slow-growing, short-trunked β-d-glycoside, β-amirin and C-glycoside with a much-branched, bushy, broad, rounded flavones [6-8]. crown and reaches 6-9 m in height. The edible Averrhoa carambola has been reported to fruits have thin, waxy, orange-yellow skin and exhibit several pharmacological activities which juicy, crisp, yellow flesh when fully ripe. Slices include: antioxidant [9], anti-inflammatory [10], of the fruit cut in cross-section have the form of antimicrobial and antifungal [11, 12], anti-ulcer a star [2]. In traditional medicine, the fruit is [13] and hypoglycaemic [14]. It also has used for treating ailments such as cough, food electrophysiological effects [15], amongst other poisoning, sore throat and malaria; the root, for properties. treating arthralgia (joint pain), chronic headache, Averrhoa carambola, though not widely and epistaxis (bleeding from the nose); the distributed in Nigeria, has shown in traditional 1 J. Chem Soc. Nigeria, Vol. 43, No. 2, pp 141 - 150 [2018] medicine that the fruit, root and leaves can be thickness with 5 % phenyl methyl silicone as the used in treating several aliments [2]. Its versatile stationary phase. The carrier gas was Helium use in traditional medicine necessitated this (1.2 ml min-1) and the injector temperature was research. This study was aimed at investigating kept at 250 °C. The oven temperature was the chemical composition and antimicrobial programmed at 50 °C (1min) to 180 °C at 10 activity of the essential oils of the fruit and leaf °Cmin-1 (0min) and then 230 °C for 5 °Cmin-1 of Averrhoa carambola. (0min) to 330 °C for 10 °Cmin-1 (2min). The mass spectra were acquired at 70 eV within a Materials and Methods mass range of 38-550 Da with a scan time of Collection and preparation of plant material 0.73 scan s-1 and ion source temperature Averrhoa carambola fruits and leaves were maintained at 230 °C. obtained from a farm at Umuebule 4, Oyigbo Town in Oyigbo Local Government Area of Analysis of essential oil Rivers State, Nigeria on the 28th of June 2017. GC-MS was used to analyze the extracted The plant was identified by Professor (Mrs.) B. essential oils of Averrhoa carambola fruit and Green, a Taxonomist of the Department of Plant leaf. The components of the oil were identified Science and Biotechnology, Rivers State based on the comparison of their retention time University, Nigeria. The fruits and leaves were and mass spectra with those of standards and handpicked, washed to remove debris and National Institute of Standards and Technology cleaned. The fresh fruits (2 kg) and fresh leaves (NIST) Standard Reference Database 69 of the (1.5 kg) were separately chopped in to smaller GC-MS system. sizes using a kitchen knife to allow for easy placement into the round bottom flask and to Bioassay of Averrhoa carambola Essential increase surface area. Oils Preparation of Averrhoa carambola leaf and Essential oil extraction fruit essential oils Extraction was done via hydrodistillation using a Essential oil (0.1g) of both leaf and fruit of Clevenger apparatus [16-18] on the 29th of June Averrhoa carambola were separately dissolved 2017. The chopped fruits and leaves were in 10 ml dimethylsulphoxide (DMSO) and 10 ml respectively introduced into the round bottom 0.5 % Tween 80 [19] to produce 100 µg/ml flask fitted with a Clevenger apparatus, and was standard stock solutions for both leaf and fruit heated for about 1hour 30 minutes at a oils used for the disc diffusion assay. temperature of 60 °C to extract the volatile organic compounds present in the fruit and leaf. Test microorganisms The distillates were collected into airtight glass Antimicrobial and antifungal activities of the vials and stored at 4 °C under refrigeration until volatile oils were evaluated against two Gram- analysis. The following formula was used to positive cocci and two Gram-negative bacilli determine the essential oil yield: bacteria and one fungus by the disc diffusion Essential oil yield (%) = W1/W2 x 100 % method. The microorganisms used were Where: W1 = net weight of oil (grams) Staphylococcus aureus, Escherichia coli, W2 = total weight of the plant sample Pseudomonas aeruginosa, Bacillus subtilis and (grams) Aspergillus niger. All the microorganisms used were clinical isolates obtained from Department Instrumentation of Medical Laboratory Science, Rivers State The instrument used for the analysis is gas University, Nkpolu-Oroworokwo, Port Harcourt, chromatography-mass spectrometry (GC-MS) Nigeria. with Agilent 7890A model GC system coupled with 5975C VL MSD. The GC equipment was Antimicrobial analysis fitted with HP 5MS capillary column, length The disc diffusion method [20, 21] was used to 30m; internal diameter 0.30 mm; 0.25 µm film assess the antibacterial activity as well as the 2 J. Chem Soc. Nigeria, Vol. 43, No. 2, pp 141 - 150 [2018] Minimum Inhibitory Concentration (MIC) of the The yield of volatile oil from Averrhoa volatile oil from Averrhoa carambola leaf and carambola fruit was 1.06 % (w/w). From the fruit. Nutrient Agar plates were prepared and a GC-MS analysis, 17 compounds were identified 24hour old culture of the bacterial suspension (Table 1). The data and spectrum (Fig. 1) (equivalent to 0.5 McFarland suspensions) of interpretations were done using the National test microorganisms were inoculated by the Institute of Standards and Technology (NIST) spread plate method. Sterilized filter paper discs Standard Reference Database 69 of the GC-MS approximately 5 mm in diameter were soaked system. The result showed the oil to be with the already prepared essential oil stock composed of estragole (1-methoxy-4-(prop-2- solutions and placed on the prepared agar plates. en-1-yl)benzene) (62.312 %) (3), trans-α- Each disc was pressed down to ensure complete bisabolene (4-[(1E)-1,5-dimethyl-1,4-hexadien- contact with the agar surface and distributed 1-yl]-1-methyl-cyclohexene) (12.209 %) (12), evenly so that they were no closer than 24 mm pinene ((1R)-2,6,6-Trimethylbicyclo[3.1.1]hept- from each other, centre to centre. The agar plates 2-ene) (8.246 %) (1), ocimene (3,7-dimethyl- were incubated at 37 °C for 18 to 24 hours for 1,3,6-Octatriene) (4.095 %) (2) and other minor bacteria and 25 °C for 5 to 6 days for the fungus; compounds. Among constituents identified, after which each plate was examined, and the terpenoids (63.335 %) were the most abundant zones of inhibition were measured including the constituents (Table 2). diameter of the disc. The zones of inhibitions With respect to Averrhoa carambola fruit observed for the essential oils were within the essential oil composition, there have been some range of 0 mm – 14 mm. While those of the investigations providing informative data which standard control (Ciprofloxacin) were within 0 vary from the result of our study. Butyl acetate, mm – 35 mm. DMSO and 0.5 % Tween 80 were ethyl decanoate and hexadecanoic acid were used as negative controls. They showed no shown to be the most abundant components of activity. Three other concentrations (50 µg/ml, Averrhoa carambola fruit essential oil from 20 µg/ml and 10 µg/ml) were prepared from the Cuba [22]. Higher amounts of esters stock solutions and used for the disc diffusion (predominantly methyl anthranilate) were analysis.
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