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Laportea Aestuans (L.) Chew Inhibits Oxidation and Microbial Growth in Vitro

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Laportea Aestuans (L.) Chew Inhibits Oxidation and Microbial Growth in Vitro EXCLI Journal 2013;12:894-906 – ISSN 1611-2156 Received: August 27, 2013, accepted: October 21, 2013, published: October 28, 2013 Original article: CHRYSEN-2-OL DERIVATIVE FROM WEST INDIAN WOOD NETTLE LAPORTEA AESTUANS (L.) CHEW INHIBITS OXIDATION AND MICROBIAL GROWTH IN VITRO Ganiyat K. Oloyede*, Martha S. Oyelola Natural products/Medicinal Chemistry Unit, Department of Chemistry, University of Ibadan, Nigeria * corresponding author: Ganiyat Kehinde Oloyede, E-mail: [email protected], Telephone: +234 803 562 2238 ABSTRACT Bio-active compounds present in West Indian Wood Nettle Laportea aestuans (L.) Chew (Ur- ticaceae), used in ethno medicine as antioxidant and antimicrobial were studied. The aim of this research work was to isolate and characterize the bio-active compounds in the n-hexane fraction of L. aestuans, determine the toxicity and subject it to in-vitro antimicrobial and free radical scavenging activities. The chemical constituents were isolated by gradient elution co- lumn chromatographic technique and Ultra Violet/visible (UV), Infrared (IR) and Nuclear Magnetic Resonance (NMR) spectroscopies were used for structural elucidation. The free rad- ical scavenging activity of the isolate was assessed using three methods; scavenging effect on 2,2-diphenyl-1-picrylhydrazyl radical (DPPH), hydroxyl radical generated from hydrogen peroxide and ferric thiocynate method. Antimicrobial screening was done by agar well diffu- sion method while toxicity was determined by Brine shrimp lethality test. Structures were proposed for the white crystalline solids isolated; (4E)-3,6-dimethylhep-4-en- 3-ol (AB) and 1,2,3,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11-hexadecahydro-1,1,6a,10b-tetrame- thyl-7-((E)-4,7-dimethyloct-5-enyl) chrysen-2-ol (AC). Percentage yield of AC was 91.2 and was non-toxic with LC50 (µg/ml) value of 1581233000.0. AC significantly scavenged free radical at 0.0625 mg/ml in the DPPH (64.73 %) and hydrogen peroxide (99.22 %) tests. It al- so showed 65.23 % inhibition at 1.0 mg/ml in the ferric thiocyanate test. AC also inhibited microbial growth significantly when compared with gentamicin and tioconazole which are an- tibacterial and antifungal standards respectively. The presence of Chrysen-2-ol derivative in L. aestuans which was non-toxic and possessed significant antimicrobial and antioxidant ac- tivities supports its ethno medicinal application. Keywords: Laportea aestuans, (4E)-3,6-dimethylhep-4-en-3-ol, chrysen-2-ol, toxicity, antimicrobial, antioxidant INTRODUCTION ries and books (Gbile, 1986; Ghani, 1986; Dokosi, 1998). Secondary plant metabolites The potential of plants as a veritable also referred to as natural products are re- source for pharmaceuticals and other thera- nowned for their potent pharmacological peutic materials have been emphasized. activities; as antimicrobial, insecticidal, an- Plants with medicinal values often referred ticancer, antioxidant, pesticidal, amongst to as secondary metabolites have been do- others. Some are odoriferous and find ap- cumented in herbal pharmacopeias, directo- 894 EXCLI Journal 2013;12:894-906 – ISSN 1611-2156 Received: August 27, 2013, accepted: October 21, 2013, published: October 28, 2013 plication in perfumes and cosmetics, for Britigan, 1997). It was also suggested that flavoring foods and drinks and for screen- free radicals, such as superoxide radical - - ing incense and household cleaning prod- (O2 ) and hydroxyl radical (OH ) and non- ucts. They include alkaloids, flavonoids, free radical species, such as hydrogen per- 1 steroids, coumarins, anthocyanins, terpe- oxide (H2O2) and singlet oxygen ( O2) noids and essential oils (Brinker, 1998; within the human body facilitate cellular in- Burkill, 1985; Gbile, 1986; Abu-Rabia, jury, ageing, development of neurodegener- 2005; Gilbert and Martin, 2006). In recent ative and cardiovascular diseases (Stadt- years, there has been an extensive growth in man, 1992; Ames et al., 1993; Alan and natural product chemistry. This is due to Miller, 1996; Knight, 1998; Pinzino et al., advances in isolation, characterization, 1999; Cadenas and Davies, 2000; de la identification, purification and synthesis of Fuente, 2000; Stanner et al., 2004). Con- new natural products. Many of today's med- sumption of fruits and vegetables has prov- icines are obtained directly from natural en to substantially reduce the risk of cardi- sources and a renewed interest in the ovascular diseases and neurodegenerative screening of plants for biological activity is diseases, including Parkinson’s and Alz- due to the developments of in vivo and bio- heimer’s diseases (Di Matteo and Esposito, chemical screening methods (Kokwaro, 2003; Bjelakovic et al., 2007). Paul (2008) 1993; Heywood, 1993). isolated a mixture of methyl esters of ali- Laportea aestuans, the West Indian phatic acids from Laportea aestuans. Also, wood nettle, is an annual herb of the Urti- the essential oil from the plant was found to caceae or nestle family. It is native to tropi- be dominated by methyl salicylate and had cal Africa, although it is now widespread as significant antioxidant and antimicrobial an introduced species throughout both the activities (Oloyede, 2011) while phyto- western hemisphere and eastern hemisphere chemical, toxicity, antimicrobial and anti- tropics and subtropics, including the USA. oxidant screening of extracts obtained from Laportea aestuans (Linn) Chew have the Laportea aestuans (Gaud) had also been following synonyms; Urtica aestuans, investigated (Oloyede and Ayanbadejo, Fleurya aestuans (Gaud) and Fleurya aes- 2013). Based on our findings, there was tuans (Linn.) Miq. It is used as abortifa- need to isolate and characterize the bio- cient, antimicrobial, laxative, in eye treat- active compounds in Laportea aestuans. ments and pain-killers. It is also used in The prevalence of microbial infection and treating pulmonary and stomach troubles, oxidation reaction is also a major driving diarrhea and dysentery (Chew, 1969; Bur- force for this study. This current study is kill, 1985; Friis, 1993; Nadine, 2001). therefore aimed at isolating and characteriz- Laportea aestuans (L.) Chew is recorded as ing the plant’s secondary metabolite using an ethno veterinary species that is used for chromatographic and spectroscopic tech- urinary problems of ruminants in Trinidad niques (UV, IR and NMR). Antioxidant and and Tobago and also to shorten labour and antimicrobial screening of the isolated pure remove the placenta during childbirth compound was also carried out and the tox- (Lans, 2006, 2007). Epidemiological stud- icity level was determined using Brine ies indicated that consumption of L. aes- shrimp larvae eggs. tuans inhibits the damaging activities of free radicals in human body (Morrison and MATERIALS AND METHODS Twumasi, 2010). Free radicals find their Chemicals and reagents way into the human body via metabolic Dimethylsulphoxide (M&B, England), pathways within body tissues and also from hydrogen peroxide (Merck, Germany) and external sources such as food, drugs and 2,2-diphenyl-1-picrylhydrazyl (DPPH), sil- pollution from the environment (Miller and ica gel 60-200 mesh size, ascorbic acid, bu- 895 EXCLI Journal 2013;12:894-906 – ISSN 1611-2156 Received: August 27, 2013, accepted: October 21, 2013, published: October 28, 2013 tylated hydroxylanisole (BHA), rutin and α- Test organisms tocopherol were obtained from Sigma Escherichia coli, Staphylococcus aure- Chemical Co (St Louis, MO). Brine shrimp us, Bacillus subtilis, Pseudomonas aeru- larvae eggs were obtained from Ocean Star ginosa, Klebsiellae pneumonae, Salmonel- International, Inc. Company, USA. Ace- lae typhi, Candida albicans, Aspergillus tone, chloroform, ethyl acetate, n-hexane, flavus and Fusarium moniliformes (Micro- methanol, butanol, chloroform, hydrochlo- organisms were collected from the stock of ric acid, ammonia solution, naphthol, bis- the Department of Microbiology, Faculty of muth nitrate, potassium iodide, sodium hy- Science of University of Ibadan). The test droxide, copper acetate, NaOH, ferrous organisms were maintained on nutrient agar chloride, sodium chloride, copper sulphate slopes and kept in a refrigerator at 4 °C. Al- pentahydrate, ferric chloride, conc. tetra- iquots of nutrient broth (100 ml) were inoc- oxosulphate (VI) acid, conc. HCl, ammonia ulated with the culture of test micro- solution, sodium potassium tartarate, linole- organisms using a loop and then incubated ic acid, ammonium thiocynate, ethanol, hy- at 37 °C for 24 h. drochloric acid, potassium chloride, glacial acetic acid, disodium hydrogen phosphate Reference standards and dihydrogen potassium phosphate were Gentamicin (80 μg/ml) and nystatin all BDH general purpose chemicals and (80 μg/ml) were standards for bacteria and solvents were distilled prior to use. fungi respectively for the antimicrobial screening. Ascorbic acid, butylated hydrox- Equipment and apparatus yanisole (BHA), α-tocopherol and rutin Rotavapor RII0 (Buchi, England), were used for antioxidant activity. Dime- Soxhlet apparatus, Ohaus analytical balance thylsulfoxide (DMSO) was used for cyto- (USA), Steam Bath (Gallenkamp), silica gel toxicity studies. GF254 (precoated aluminium sheets - Merck Germany), pH meter (Jenway model), Sample preparation Gallenkamp melting point apparatus, UV- Whole plant of L. aestuans was collect- Visible spectrophotometer (UVD-2960 ed, sorted to remove dirt, weighed and air model equipped with a UVWIN software dried for 3 weeks until the weight was con- version LABOMED INC, USA). IR Spec- stant
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