JJST magazine 2014

JAMAICAN JOURNAL OF SCIENCE & TECHNOLOGY, Volume 21-24 ISSN: 1016-2054 |

Volume 25 | December 2014 | Pages 2-31

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www.src.gov.jm

A Survey of Ackee Fruit Utilization in Ghana The ackee tree (Blighia sapida) is a woody perennial fruit tree species indigenous to the tropical forests of West Africa.

Can Cars Really Run on Water?

The team from Maynex Technology has developed technology described as the MaynexH2-Flex Hydrogen Generator.

Synthesis of Napthoquinone Azoles as Potential Antibacterial Agents Drug resistance within the medical field has pushed research

towards the development of new and effective antimicrobial drugs with different modes of actions.

RESEARCH IN PROGRESS Young Scientists’ Abstracts INSIDE THIS ISSUE.

www.src.gov.jm JJST ISSN: 1016-2054

Published by: The Scientific Research Council, Information Services Division, Hope Gardens Complex, Kingston 6, Jamaica W.I.

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Table of Contents

3 | From the Editor 4 | Editorial Page

5 | Research Briefs THE FORUM 6 | Can Cars Really Run on Water?

(Authors—Harlo Mayne and Maynex Technology Limited [et al])

Can Cars Really Run on Water?

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MAIN ARTICLES 11 | A Survey of Ackee Fruit Utilization in Ghana (Authors—Osei [et al], Joycelyn Anima RESEARCH REVIEW 18 | Napthoquinone Azoles as Potential Antibacterial Agents (Authors—Nadale Downer-Riley [and Latoya Wright) RESEARCH IN PROGRESS [Young Scientists’ Abstracts]

A Survey of Ackee Fruit Utilization...

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Research in Progress...

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25 | Uncommon Fruit Species of Jamaica: Potential for Improved Health and Economic Conditions (Camille S. A. Bowen Forbes) 26 | Investigating the Economic Potential of Jamaican Ackees (Andrea Goldson Barnaby) 27 | Endemic Plants in the Cockpit Country: Jamaica’s Treasure (Andrew S. Lamm et al) 28 | Potential of Two Jamaican Essential Oils Against Mosquitoes and Bacteria (Chenielle M Delahaye McKenzie) 30 | Guide for Authors

ON THE COVER More widely known for its poisonous properties than as an edible fruit, the akee, Blighia sapida K. Konig (syn. Cupania sapida Voigt.), of the family Sapindaceae, is sometimes called ackee, akee apple, or vegetable brain (seso vegetal in Spanish). On the Ivory Coast of West Africa, it is called kaka or finzan; in the Sudan, finza. Elsewhere in Africa it is generally known as akye, akyen or ishin, though it has many other dialectal names. In Ghana, the fruiting tree is admired as an ornamental and is planted in villages and along streets for shade. The akee was brought to Jamaica in 1793 by the renowned Captain Bligh to furnish food for the slaves. The akee was planted also in Trinidad and Haiti and some other islands of the West Indies and the Bahamas and apparently was carried by Jamaican slaves to Panama and the Atlantic Coast of Guatemala and Costa Rica.

SOURCE: https://www.hort.purdue.edu/ SEE ARTICLE ON PAGE 11

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From the Editor

We promised to supply you with relevant and timely issues of the Jamaican Journal of Science and Technology (JJST). For various reasons we have fallen a bit short and are late, but we do hope that our content will have been worth waiting for. Before summarising the content of our present issue, we draw your attention to some current, seminal S&T developments. Notably, the National Commission for Science & Technology (NCST) has been resuscitated with Professor Errol Morrison, formerly President of the University of Technology, at the helm. We congratulate Professor Morrison on this appointment and trust that he will bring his considerable energy and insight to bear upon the burning issues which have been in abeyance for too long during the hibernation of this important institution.

Importantly, the formulation and approval of a pertinent and practical science policy which will guide the governance of critical matters such as science education aimed at producing a scientifically savvy and enthusiastic population and workforce will be paramount. But complementarily, it will be essential to engage our industries in effectively and efficiently using this knowledge and this workforce to generate new and globally competitive products. Policy and action to facilitate such development will be paramount and, indeed, have already begun, as exemplified by the establishment of the National Nutraceuticals Industry (NNI) initiative. In this respect, we note that Dr. Henry Lowe (Eden Garden Nutraceuticals) continues to gain new patents for potential anticancer agents and expect that these will quickly be translated into products which will accrue in positive ways to Dr. Lowe and to our economy in general. Dr. Lawrence Williams (SRC) has announced that his patented formulation from Guinea Hen Weed (Petiveria alliacea) targeting cancers and degenerative diseases has been certified by the Ministry of Health and will be going into production shortly. We note also, that Dr. Daniel Coore (UWI) and his collaborating innovators have licenced their exciting Cardiac Simulator and that manufacture has begun of this device, which has enticed the American College of Cardiothoracic Surgeons to encourage its use in training all its new Fellows. This is hardly a product for the mass market and will be unlikely to have enormous economic impact but its development, wide acceptance as an outstanding innovation and manufacture as a commercially available product are exemplary. So there is significant activity on various fronts in the Science and Technology arena – but we encourage the NCST and our scientific community to remember that it will also be important to formulate policy which will allow for a smooth and synergistic articulation between development and sustainability, which will be of tremendous import in the long run for our economic and social well-being and quality of life. The current drought conditions, concern about the shrinking ground-water reserves and the spate of socially, economically and environmentally disruptive bushfires, highlight these issues. Which brings us to our current issue of the JJST. There are few issues with more urgent environmental and economic importance than the way in which we source the energy required for transportation and the generation of electricity. Harlo Mayne, a winner of the National Innovation Medal (2014) writes in The Forum about his patented system for running cars on water using a cartridge with aluminium metal and caustic soda. The potential impact both locally and globally is enormous.

The ubiquitous availability of bactericidal agents is a two-edged sword - affording us protection against infection, but also generating, through an evolutionary arms-race, new strains of bacteria which are resistant to the most widely used agents. Dr. Nadale Downer-Riley in her article on napthoquinone synthesis introduces us to a systematic approach to chemical synthesis of new varieties of bactericidal agents which could help us to keep pace with the dangerous resistant strains of bacteria turning up in our hospitals - the very places which should be protecting us from microbial predations.

It is said that the ackee, Blighia sapida, brought here from West Africa, is commercially consumed only in Jamaica. Joycelyn A.Osei and collaborators from Ghana seek to emulate our commercial exploitation of this fruit and investigate the current and potential uses of ackee in their market, providing an interesting alternative perspective on a component of a major national dish. As usual, our Research In Progress provides a quick synopsis of some of the topics being researched by our young scientists - focussing on natural products/nutraceuticals (including ackee) and the high incidence of endemic plants in the cockpit country. We trust that you will find here several areas of interest and will write to us giving your comments, criticisms and perspectives not only on The Forum, but also on the general articles. You can provide these responses by email to Ronald.young05@gmail.com or prinfo@src-jamaica.org. We look forward to your involvement and support.

Ronald E. Young

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EDITIORIAL PAGE Chief Editor Professor Ronald E. Young Emeritus Professor, c/o School for Graduate Studies & Research Regional Headquarters, University of the West Indies, (UWI) Mona

Editorial Board Deputy Chief Editor Dr. Lawrence Williams Research Consultant, SRC

Professor Wayne McLaughlin Head, Dept of Basic Medical Sciences UWI (Mona)

Professor Tara Dasgupta Chief Editor Emeritus Department of Chemistry, UWI (Mona)

Professor Robert Lancashire Department of Chemistry, UWI (Mona)

Professor Bertram Fraser-Reid President, NPG Industries, Raleigh North Carolina, USA (Formerly Professor of Chemistry, Duke University, Durham, North Carolina) Professor Trevor Jackson Emeritus Professor Lecturer, UWI (St Augustine)

Dr. Monty Patrick Jones Executive Director Forum for Agriculturale Research in Africa, FARA Secretariat Mrs. Swarna Bandara Open Access Consultant, Jamaica Professor Albert Sasoon Senior Consultant UNESCO

Panel of Referees (8) About the Jamaican Journal of Science and Technology (JJST) The Jamaican Journal and Science and Technology (JJST) (ISSN: 1016-2054) is published by the Scientific Research Council of Jamaica (SRC) since 1990. It is a continuation of the Journal of the Scientific Research Council of Jamaica and beginning with this current volume. JJST will publish two issues for the year in electronic format as well as printed format.

SRC as the public sector agency charged with fostering and coordinating of scientific research and promotion of the application of research results in Jamaica, among other activities, also publishes the JJST to achieve its objectives. Therefore, JJST aims to publish scientific papers based on original data on research of interest and relevance to Jamaica, review papers on current scientific and policy issues. It also publishes research notes, research in progress, abstracts of projects and papers, book reviews, current events in science, profiles of scientists and technologists and perspectives. Manuscripts could be submitted in all disciplines of Natural Science, including Geology, Agriculture and Computer Science.

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JJST RESEARCH BRIEFS SYNTHESIS OF NAPTHOQUINONE AZOLES AS POTENTIAL ANTIBACTERIAL AGENTS Microbes have now displayed resistance to many azole drugs which are widely used in the treatment of fungal and bacterial infections. This drug resistance within the medical field has pushed research towards the development of new and effective antimicrobial drugs with different modes of actions. Napthoquinone azoles and precursor compounds were synthesized and evaluated against Escherichia coli and Staphylococcus aureus using the disc diffusion technique. This initial investigation screened for six compounds. Both organisms showed high sensitivity towards napthoquinone indicating that this compound is an ideal lead structure for the synthesis of other napthoquinones which can be screened for antibacterial activity against a wider panel of microbes.

A SURVEY OF ACKEE FRUIT UTILIZATION IN GHANA The ackee tree (Blighia sapida) is a woody perennial fruit tree species indigenous to the tropical forests of West Africa; it was introduced to the Caribbean by British slave traders. In Ghana, the ackee fruits are cheap but underutilized and consumed in relatively low amounts. The authors conducted an ethnobotanical survey - undertaken in two regions in Ghana - with the aim to address the indigenous knowledge and utilization of ackee fruit.

CAN CARS REALLY RUN ON WATER? The team from Maynex Technology has developed technology described as the MaynexH2-Flex Hydrogen Generator which will generate hydrogen for today’s internal combustion engines. The author describes the process using aluminum, water and proprietary additives.

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2. Can Cars Really Run on Water?

Harlo Mayne, Denver Brown and Maynex Technology Limited www.maynex.com

ABSTRACT: Dependence upon fossil-fuel engines to drive transportation or generate electricity can largely be held responsible for the now undisputed excessive rise in atmospheric carbon dioxide levels. The search for alternative energy sources has risen to the forefront and has become very pertinent to the 21st century. Maynex Technology Limited has injected a simple solution using a well-known chemical reaction between water and other agents to generate hydrogen gas in situ and on demand in a highly controlled process. The gas is used to directly power the standard internal combustion engine, replacing gasoline with little or no modification

INTRODUCTION Of course, James Watt’s steam engine, invented in the 18th century could reasonably be said to “run on water� albeit powered by coal-generated heat. This engine dominated the 19th century until the development of the diesel- and petrol-based internal combustion engines. These engines, developed toward the end to the 19th century, came to rule the industrial landscape through the 20th century up to today. Dependence upon these fossil-fuel engines (coal/diesel/petrol) to drive transportation or generate electricity, can largely be held responsible for the now undisputed excessive rise in atmospheric CO2 levels, the attendant global warming and climate change, and the depletion and hence rising cost of the once cheap and apparently inexhaustible fossil-fuel supplies. Inevitably, the search for alternative energy sources to drive our engines of civilization has risen to the fore, and has become acutely pertinent in the 21st century.

Interestingly, the main alternative that has emerged today has been around and used in engines even before the ascendancy of the fossil-fuel powered, internal combustion engine, but faded into the background because of the greater efficiency and cost-effectiveness of the latter. This alternative is the electric car, powered either by high-capacity batteries or by fuel cells, a battery which generates electricity by the reverse of elec-

trolysis. Whereas electrolysis uses an electric current to split water into hydrogen and oxygen, the fuel cell uses hydrogen gas and oxygen under pressure, with suitable catalysts, to generate electricity, producing water as an end product. Battery operated vehicles such as the Nissan Leaf or the Tesla Model S or Roadster, use rechargeable, high capacity lithium ion batteries and produce no emissions but suffer from low mileage per charge and slow recharge rates, leading to user insecurity. Perhaps, for this reason, the most popular of this type of vehicle is the hybrid electric/gasoline models such as the Toyota Prius, which have the added security of the standard gasoline engine. A broader problem with these vehicles however, is the fact that the avoidance of polluting tail-pipe emissions merely changes

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Can Cars Really Run on Water? the point of discharge of pollutants if the source of electricity for recharge is diesel fired generators, as it is in Jamaica and in many places.

Fuel cell technology avoids the limitations of range, recharge rate and ultimate reliance on fossil-fuel, but also incurs several negative features, including cost, having to carry on board significant quantities of highly explosive hydrogen gas under pressure, the sourcing of this hydrogen gas, and the long lead time and high expense of setting up hydrogen refuelling stations. Fuel cells are easily damaged by fine particles; they are very expensive and have a limited life-span. Top car manufacturers for example Toyota, Hyundai, Honda and others have been trying to roll out fuel cell technology for many years with limited success. The so-called ‘hydrogen 7’ system of the German car maker BMW in the BMW 750i involves bulky and expensive ‘k-cylinders’ installed in the trunk.

The bulky k-cylinders are perceived to be potentially dangerous in the event of an accident although this may be without adequate basis.

Into this clearly unsatisfactory scenario, Harlo Mayne, a Jamaican-born entrepreneur and inventor and his team at Maynex Technology Limited, have injected the startlingly simple solution of using a well-known chemical reaction between water, caustic soda and aluminium to generate hydrogen gas in situ and on demand in a highly controlled process, and to use this gas to directly power the standard internal combustion engine, replacing gasoline, with little or no modification. In the engine, the hydrogen is burnt to form water, the sole emission, demonstrating clearly and unequivocally that cars can indeed run on water.

2Al + 2NaOH + 6H2O → 2NaAl(OH)4+ 3H2 Sodium aluminate NaAl(OH)4 is in fact the watersoluble product used in the purification of bauxite in the Bayer Process, from which, after separation of the insoluble materials, aluminium hydroxide Al(OH)3 is precipitated and then heated to form aluminium oxide (alumina) which is used as the basis for refining aluminium metal.

Perhaps it is more than fortuitous that this process, well established in the Jamaican Bauxite industry, became the core of the invention by a Jamaican who insists that the development of his invention should be carried out in Jamaica to benefit the Jamaican worker.

In the generator, the caustic soda essentially prevents the formation of an insoluble, protective coating of hydroxide on the aluminium, accelerating the reaction between the water and aluminium thereby rapidly generating large amounts of hydrogen gas, raising the pressure in the reaction chamber. A pressure transducer and microcontroller regulate the entry of water so that the chemical reaction effectively regulates itself, providing a safety mechanism against runaway reaction. So long as unspent aluminium remains in the cartridge, the only input needed for the reaction to proceed is water, and the sole product of combustion in the engine is water.

The Maynex H2-Flex converts water of widely variable quality, including wastewater, into 100% pure hydrogen gas on demand. No electricity or external power is required. No oxygen is generated. There is no need for O2 extenders or for Electronic Fuel Injection Enhancer (EFIE) system modifications to the vehicle.

HYDROGEN AS A FUEL

This patented technology, known as the “Maynex H2Flex, Hydrogen Generator”, can provide on-demand hydrogen fuel either for an internal combustion engine or for a fuel cell. It may be used on board a vehicle or in a stationary installation to generate electricity.

The Maynex H2-Flex, Hydrogen Generator allows controlled reaction of water and sodium hydroxide with powdered aluminium in a replaceable canister according to the reaction:

Hydrogen has the most energy per unit weight of any known fuel, while aluminium has the same energy content per unit weight as oil (20,000 BTU’s or 6KW-hrs/ lb). The Maynex H2-Flex, Hydrogen Generator will generate from 1 gram of aluminium, 1 litre of hydrogen at 250 psi – so that the gas can be sprayed directly into a vehicle’s air intake system/manifold or gas tank, with absolutely no need for any major alteration of the engine.

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Hydrogen as a fuel has an octane rating of 130, thus giving the car more power than standard gasoline. High octane is good for high performance vehicles; on the other side of the spectrum the lightness of the gas can cause pre-ignition in some vehicles. This may cause a vehicle to lose power at high speed. The solutions to this include (1) reducing the timing to near top dead centre, (2) adding turbo-charge to the engine, (3) mixing hydrogen gas with other petrol and (4) adding a small amount of nitrogen to the intake.

require the building of prohibitively expensive hydrogen service stations. The Maynex H2-Flex will eliminate these problems and may, indeed, be the death-knell of the service station as we know it. The technology will make hydrogen gas on demand and there will be no need for expensive and bulky systems or more expensive service stations which may not be welcome in some neighbourhoods.

The use of hydrogen as a fuel can eliminate the need for gasoline and diesel, but at the same time greatly improves gas mileage, extends engine life, cleans the engine while driving, increases horsepower, avoids damage caused by E10, E35 and E85; eliminates harmful emissions and will pay for itself in a few months.

When using the H2-Flex Hydrogen gas there will be no need to use any other fuel; a 900 kilo car can run up to 600 kilometres on hydrogen produced from 20 litres of water and 1 kilo of aluminium and a teaspoon of caustic soda.

Like gasoline and diesel, hydrogen can be used to power today’s transportation but without any of the nasty side effects to the environment. In fact, hydrogen can reduce or even reverse global warming by putting more moisture into the atmosphere, blocking some of the damaging effects of the sun.

Our team at Maynex Technology limited is quick to note, with some excitement, that supplementation of a gasoline powered vehicle or generator with even small amounts (5% to 10%) of hydrogen can yield benefits.

Thus, once hydrogen boosted, a normal gasoline engine may effectively run using gasoline, natural gas, diesel, alcohol (methanol and ethanol), propane, castor oil, motor oil or assorted vegetable oils: there is no need to have a diesel engine in order to utilise ‘French Fry Oil’ or biodiesel. It has been noted that “The technology of using hydrogen as a combustion enhancement method in internal combustion engines has been investigated and verified for many years.”; and, further, that “… hydrogen having a catalytic effect causes a more complete burn of the existing fuel and yields significant reduction in exhaust emissions with more power and better mileage.”1 At this juncture, fuel cells can’t work in existing standard vehicles as hydrogen can. Furthermore, the provisioning of hydrogen for the operation of fuel cells may

HOW WILL IT WORK?

The aluminium will be placed in a canister or cartridge which will be able to hold as much as 6kg of powdered aluminium; 1 kg of powdered aluminium will permit a small vehicle (2000 cc) to run for up to 300 miles. The canister is recyclable. It is not expected that the cost of the aluminium would necessarily rise when cars in general start running on ‘water’. With the recycling of the aluminium the costs are expected to decrease. At the moment aluminium prices are low because so much of it is being stored in countries such as Russia, Canada, Brazil and the USA. ELECTROLYSIS VERSUS CHEMICAL REACTION An alternative to the chemical method of producing hydrogen gas from water for burning in the internal combustion engine is by electrolysis.1Producing hydrogen gas as an automobile fuel using the electrolysis of water usually requires power from a car’s 12 volt battery. The problems here are with the rate at which the hydrogen is produced and the consistency over long distances, as well as economic viability. By comparison, the Maynex H2-Flex, Hydrogen Generator needs no external power source to split the hydrogen and oxygen molecules and requires the use only of water and a readily replaceable and recyclable canister of aluminium powder.

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MAYNEX H2-FLEX, HYDROGEN GENERATOR VERSUS E10 The use of E10, a blend of 10 percent ethanol and 90 percent gasoline, has been introduced to cut down on fossil-fuel burning and to reduce the cost of gasoline. It is common knowledge that the current blend of E10 is rated at 98 octane. What is probably not as well known is that the base gasoline used in the fuel is actually rated between 82 and 84 octane. A major local car dealership had flyers warning its customers against the usage of E10. Because the possibility exists for the octane rating to drop by as much as three points, due to the fact that the ethanol will pull in moisture from the atmosphere, and because the fuel is marginal to start with, E10 cannot be considered a “buy it and forget it fuel�. Most cars are not designed to run on less than 87 octane. Clearly, this cannot compare with the direct burning of hydrogen (130 octane) as fuel.

Most new technologies foster improved product performance. These are called sustaining technologies. Some can be discontinuous or radical in character, while others are of an incremental nature. All sustaining technologies improve the performance of established products, along with dimensions of performance most valued by mainstream customers. The Maynex H2-Flex, Hydrogen Generator could conceivably represent a disruptive, discontinuous technology.

SAFETY AND COMMUNICATION Safety is a key feature incorporated into the design and whilst the fuel produced by the unit is no more volatile than traditional fuels several safety features are included in the design. The system will regulate itself shutting off when the pressure reaches a certain level, and turning back on when it falls below that level.

Tests have demonstrated that the unit is highly efficient, safe, improves engine performance and increases the lifespan of an engine due to the cleansing qualities of the addition of hydrogen gas into the fuel mix.

The system has been designed to communicate electronically with the vehicle.

BENEFITS TO THE ENVIRONMENT There are over 1 billion vehicles in use around the world, consuming over 260 billion gallons of gasoline and diesel fuel yearly. Urban transport systems based around the motor car have proved unsustainable, consuming excessive energy, affecting the health of populations, and delivering a declining level of service despite increasing investments.

The combustion of petroleum fuels is responsible for most of the smog and fine particle emissions in the USA, China, and other parts of the world. Add to that greenhouse gas emissions and you have a respiratory health hazard, which will affect future generations.

For example, despite apparent efforts to improve California's air quality, the state still has some of the most polluted areas in the USA. Over 90% of California residents live in areas that perpetually fail to meet national air quality standards. If California adopted super-efficient cars that ran on 64 miles per-gallon equivalent fuel, there would be hundreds of fewer premature deaths, 70% fewer asthma attacks, and $7.2 billion less spent on healthcare each year, says a new report issued by the American Lung Association in California2.

NEGATIVE IMPACTS When used correctly, there will be no known negative impact on the environment. Even if H2-Flex is used incorrectly, there will only be positive outcomes for the environment as the device will prevent millions of tons of carbon dioxide from being dumped into our atmosphere; water vapour from vehicle exhaust will result in cooler temperatures and cause plants and wildlife to flourish. Aluminium is considered a very safe metal and is used as fertilizer in the form of aluminium sulphate. It is used as a soil acidifier as desired by acid loving plants3.

HOW WILL JAMAICA BENEFIT? With this technology, Jamaica will be able to: Save at least 60% on fuel cost annually; the user of the H2-Flex can travel up to 600 kilometres with a J$2500.00 aluminium cartridge. It will cost at least twice as much to travel the same distance with gasoline.

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Revive the ailing bauxite industry as this would have a knock on effect if the use of the device became global Cut emissions of particulates and noxious and greenhouse gases from vehicle tail pipes, thus cleaning the environment by up to 70%, which will in turn assist in cost saving by the Ministry of Health from the monies paid to treat respiratory illnesses.

Last but not least, our technology will help the country to reduce the high unemployment rate especially of our young people. This is primarily because we will be able to employ persons in our factories to assemble the product. It is envisioned that plants would be established for the manufacture and recycling of the aluminium cartridges. These replacement cartridges can be sold in any existing retail outlet and because of their ease of use – they can be inserted into the H2-Flex much quicker than filling up a vehicle with petrol.

FUTURE PROSPECTS

About the Inventor Harlo Mayne is an entrepreneur who was born in Falmouth, Jamaica and he was raised in between Vineyard Town, Kingston and the parish of his birth. As a youth, he moved to the United States. He describes himself as being an inventor and problem solver all his life but his epiphany began with the energy crisis in 2008 and thus he was inspired to create his invention for the future of energy and the world.

In 1986 Mr. Mayne was awarded a United States patent for a 12 Tri-fold Oral Hygiene set and the award winning Cross Action Bristle toothbrush. For his newest invention – The Maynex H2- Flex he was also granted in 2014 a patent by the same US Patent Office and he received the 2014 Jamaica National Innovation Medal.

His experience is varied from manufacturing to product research and development and concept design. Mr. Mayne also finds time volunteering as a mentor to young inventors.

The Maynex Team truly believe that with the appropriate investment in research and development (R&D) the Maynex H2-Flex can replace the presently depleting fossil fuel industry. There is also a future for the development of a hydrogen battery which would allow for the conversion of the hydrogen gas into at least 10,000 w of electricity to power hydrogen electric vehicles and homes with much greater efficiency. It is anticipated that the hydrogen battery will last for approximately 10 years and will keep charged as long as water and the cartridge remain in the H2-Flex.

REFERENCES [1] [2] [3]

Dülgers, Z. & Özçelik, K.R. (2000). Fuel economy improvement by on board electrolytic hydrogen production. Int J Hydrogen Energy25:895-897.

American Lung Association in California; www.lung.org/associations/states/california.

Aluminium Sulphate as Fertiliser; www.aluminiumsulphate.net.

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1. A Survey of Ackee Fruit Utilization in Ghana *Joycelyn Anima Osei,1 Edward Ken Essuman,2 Daniel Owusu Kyeremateng,1 and Jacob Agbenorhevi1 1

Department of Food Science and Technology, Kwame Nkrumah University of Science and Technology, Ghana; 2Ken Consult *Email address: sweetjoy50@gmail.com

ABSTRACT: Blighia sapida is a woody perennial fruit tree species native to West Africa. The fleshy arils of the ripened fruits are edible while the seeds and capsules of the fruits are used for soap making. Our ethnobotanical survey revealed that although the ackee fruit is overlooked by researchers in Ghana, the fresh ackee aril is traded in some local markets. People have different interests in using ackee and variable knowledge of its uses. Preferred bakery products from suggestions in the survey conducted were cake, chips and rock cake.

Keywords: Ackee fruit, Consumer preference, Local names

INTRODUCTION Ghana is endowed with ackee fruits which are cheap, underutilized and consumed currently in relatively low amounts. There is increase in public interest in ackee fruit utilization as in other part of the world especially Jamaica where it forms part of the national dish [1] and Nigeria where it serves as a staple food [2] because of its high dietary protein and many disease preventive properties. The ackee fruit is an African native crop introduced to the Caribbean by British slave traders.

The ackee tree (Blighia sapida) of the family Sapindaceae is indigenous to the tropical forests of West Africa and grows to a height of 10 to 12 m at maturity.

Not surprisingly, there are ackee place-names such as Ackee Walk in Kingston and Ackee Parade in St. Thomas.[3] There are also ackee business-place names: Ackee Tree Hideout and Jerk Pork Center. The capital city of Kingston is named the “Big Ackee”.[4] The economic potential of ackee is largely untapped in West Africa. The ackee industry in Jamaica, which is well developed, generated approximately US$ 400 million in revenues in 2005 [1]. This indicates the potential for developing an ackee industry in West Africa.

The only economic data available from West Africa come from a survey of one rural township in Benin.

An ethnobotanical survey conducted in Benin found that farmers characterize ackee types using criteria that are mostly related to the fruit and its different parts.[5] The trivial name ackee is derived from the terms “anke” and “akye-fufuo” which are used to describe the fruit in West Africa. In Ghana the name Ankye which refers to ackee comes from the Twi language.

The fruit was named by Koenig as Blighia sapida in honor of the infamous Captain William Bligh of Mutiny on the Bounty who transported the fruit from Jamaica to the England scientific community at Kew in 1793.[6,7,8,9,3,10] Consumption of ackee is mainly in Jamaica, Haiti and some parts of West Africa. Unlike Ghana and other parts of West African countries, ackee fruit is freshly sold in the local markets and common on the roadsides of the island of Jamaica. Most Jamaicans eat the fruit cooked, while others consume it raw. Fresh arils, dried arils and soap made from ackee are traded in local and regional markets in Benin providing substantial revenues for farmers, especially women.[11,12]

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A Survey of Ackee Fruit Utilization in Ghana Despite the abundance of ackee fruit in Ghana, information necessary to elaborate a clear domestication strategy is still very sketchy. However, research to increase the value of this underutilized species and to make it more widely available would broaden the agricultural resource base and increase the livelihood options for rural communities. The aim of this investigation is to address the indigenous knowledge and utilization of ackee fruit in Ghana.

MATERIALS AND METHODS

Research location The study was undertaken at two regions in Ghana namely Ashanti region and Brong Ahafo region.

groups. While women conserve ackee for soap making and food preparation, men keep the trees for shade.[5] People have different interests in using ackee and variable knowledge about ackee fruits. Regardless of gender and level of education, only some respondents consumed ackee fruit. Out of 156 respondents, 12 had no knowledge of ackee fruit (Table 1).

Of the 12 who had no knowledge of ackee, 8 had only heard of it and the remaining 4 knew nothing at all about ackee.

About 41.8% of the respondents said the ackee fruit is sold in the market. Among the towns where the survey was conducted, Techiman recorded the highest number of respondents who perceived that the ackee fruit was sold in the market (Table 1). It is sold in a town called Ofuman, near Techiman in the Brong Ahafo Region of Ghana.

Sampling and data collection Open- and closed-ended questionnaires concerning Blighia sapida (ackee fruit) were prepared for the study. A total of 156 respondents were selected from the study area using simple random sampling technique. Each individual was chosen entirely by chance and each member of the respondent has an equal chance of being included in the sample size. Information that was collected includes background data of respondents, local name of the ackee fruit and its meaning in the local language, local uses and processing of ackee products. The different traditional products obtained from ackee trees were recorded.

Statistical Analysis Statistical Package for the Social Sciences[13] was used to analyse survey data using descriptive analysis such as frequencies and percentages and presented using tables, bar and pie charts.

RESULTS AND DISCUSSION Demographic Information and Indigenous Knowledge of Ackee Fruit A total of 158 respondents were used for data collection: 106 females and 52 males. In general, indigenous knowledge about ackee varied among gender

Local names of ackee Ackee is derived from the original name ‘Ankye’ which comes from the Twi language of Ghana. Blighia sapida is commonly known in English as ackee, akee or akee apple. B. sapida is designated in each town by different local names including kyeraa, achin, akyii, finjeri, ache, achiaa, achena, atee, atina, atiaa,

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A Survey of Ackee Fruit Utilization in Ghana peena, semina aba, akye fufo and semina dua. Although 31% of the respondents do not know the local name of ackee, majority called it kyeraa representing 29.7% (Table 2).

Respondents mentioned that the name “semina aba” or “semina dua” is derived from the soapy nature of the ackee capsule. All others local names do not have any particular meaning. In Benin, more than 20 local names are known for ackee, each given by different ethnic groups.[14,7,11] On the Ivory Coast of West Africa and Mali, it is called kaka or finzan and finza in the Sudan.

Reasons for using ackee, forms of consumption and Preservation Consumption of the ackee is mainly in Jamaica, Haiti and some parts of West Africa. In Jamaica, the fruit serves as a major component of the national dish ackee and codfish.[15]

Out of the 158 respondents, only 93 (58.9%) eat ackee fruit (Table 1). At maturity, arils are consumed directly fresh, added to sauce to replace sesame (Sesamum indicum L.) seeds or peanuts (Arachis hypogaea L.), or dried and presumably grounded into powder and added to sauce mainly to release its oil contents. Most of the respond-

ents use the aril in soup preparation in place of okra while others make it into a paste and eat with kenkey.

Consumers eat the aril because of its sweetness (32.3%) followed by its nutritiousness (17.7%) as shown in Figure 1. Ackee is indeed nutritious as it is high in fatty acids and rich in protein, potassium, iron, and vitamin C. [10] Some respondents also eat ackee because of its fats and oils. It is a major food in Jamaica and is noted for its high protein and fat contents.[16] A large percentage of the ackee (arils) consists of lipids, 51-58% by dry weight.

[17] The major fatty acids found are linoleic, palmitic and stearic acids with 55% of this being linoleic acid.[10] Although ackee arils contain linoleic acid (a polyunsaturated omega-6 fatty acid) which is an essential fatty acid (the body does not make it and we have to obtain it from our diet), only 1.3% of the respondents mentioned they eat ackee aril because of its fat and oil. This type of fatty acid is known to be important for membrane development in the eye and brain. However, too much omega -6 has been implicated in prostate cancer.[18] It is therefore advisable to mix ackee with fish (which is rich in omega-3 fatty acids), as in the saltfish and ackee combination.

Figure 1. Reasons for eating ackee fruit

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A Survey of Ackee Fruit Utilization in Ghana Sixty-five (65) of the respondents representing 41.1% do not eat ackee fruit, the reasoning being that they do not know whether the ackee is edible and the benefit they will derive from eating it.

Others say it is not popular and that they have not seen it before or known of it being used as recipe in food preparation, while others say it is poisonous or contains poison. The poisonous nature is the main drawback to its application because of the toxicity which manifests as diarrhea, hypoglycemia, nausea and vomiting commonly known as Jamaican vomiting sickness (JVS) or toxic hypoglycemic syndrome.[18] Ackee fruits are noted for their poisnous effects when consumed unripe or overripe.[19] Both the skin and seeds of the ackee are also poisonous.

The presence of amino acids, hypoglycin A and B, cause the fruit to be toxic. The hypoglycin content diminishes after sunlight reaches the mature arils. The mature ackee fruit splits open naturally when it is ripe, and then is picked and prepared. There is a traditional saying worth remembering - the ackee must ‘smile’ before being picked off the tree.[20] Several papers and review articles have been published on the toxic nature of ackee and the biochemical activity and pathway of hypoglycin A and B.[2123,24,25,26,3,27,28,10] On the whole, properly picked and prepared ackee is delicious and considered safe to eat.

Preferences of the respondents to various form of consumption of ackee aril are shown in Figure 2. Among these, fresh aril is mostly consumed representing 40.51%, followed by fresh and boiled (30.38%). The respondents who said they do not know any form of ackee consumption represent 14.56% (Figure 2).

Large numbers of the respondents use ackee aril mainly in preparation of food such as soups.

More generally, other recipes of ackee aril such as ackee pudding and rum sauce, braco-style ackee bread, jerk ackee gizzada [29], ackee fritters, ackee stuffed breadfruit [20] have also been docu-

mented. Although the arils of ackee fruit can be parboiled with salt and sometime spices, they are mainly dried for conservation purpose and this is usually the commercialized form at local markets [5]. As shown in Table 3, respondents who preserve ackee by drying formed 35.4 % followed by those who have no idea of preservation methods for ackee (32.9%).

Figure 2. Forms of ackee fruit consumption Products derived from ackee Apart from the fleshy arils of the ripened ackee fruits being used as a vegetable in food preparation, other utilizations of the aril have been reported in other West African countries.

[30,31] The seeds and capsules of the fruits are also used for soap-making and for fishing and all parts of the tree have medicinal properties.[5] Out of the 158 respondents questioned, 91 (57.6%) know about ackee fruit products (Table 4). However, most of the respondents mentioned that they themselves do not use the ackee in making these products but heard of other people who use it. This means that the ackee is not being well utilized in Ghana as compared to other West African countries like Benin where they generated US $ 10,000 of revenue[5] representing almost 20% of the family income competing with major staples such as maize (20%), sorghum (21%) and common beans and cowpeas (15%).[12]

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A Survey of Ackee Fruit Utilization in Ghana

shown in Figure 3.

Regardless of variations in proportion of respondents with knowledge of ackee products, respondents showed highest preference for use of ackee fruit for soap making (29.7%) followed by oil (11.4%). The majority of the respondents mentioned more than one product that ackee fruit could be used for. The pods of ackee (capsule or pulp/skin) are mainly used for laundry in times of scarcity. Innovative women trying to cope with the lack of washing soap would remove the pods and rub them on the clothing. According to the respondents, this type of utilization was very popular in the past across the country before the introduction of manufactured soap. This produced suds and left the clothes clean. This cleaning property is due to the high levels of saponins in the pods or capsules which lather in water and are used as a soap substitute and in soap making.[1,5]

Respondents’ preferences on the type of ackee aril product Respondents’ preferences for types of ackee aril product are shown in Figure 3. The bar chart shows that the highest number of respondents preferred cake and chips (20.3 %) followed by chips (19.0 %) and cake (16.5 %). Almost all of the respondents expressed interest in the development of ackee into pastry products, except for 3.8 % of the respondents who do not know the kind of product to be developed from ackee as

Some respondents mentioned other products not listed in the questionnaire, like ackee flour, canned ackee oil, canned ackee and ackee paste, which are not well known in Ghana but are being produced in other countries. Canned ackee has earned Jamaica US $ 4.3 million (J$223.3 million for 1,507,635 kg of ackee) in 1999 and US $ 8.5 million in 2002 [18]. The economic potential of ackee is largely untapped in West Africa. This indicates the potential for developing an ackee industry in Ghana.

CONCLUSION In general, the ethnobotanical survey revealed clearly that unlike other West African countries, indigenous knowledge about ackee (B. sapida) is not well developed in Ghana although a majority of the respondents eat the ackee aril. Ackee has been utilized for centuries and is still an important plant genetic resource today.

Respondents have different names for the species indicating age-old knowledge and uses. Apart from ackee aril being processed into paste, findings in this study have shown the potential for the production of bakery products such as cake and chips.

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A Survey of Ackee Fruit Utilization in Ghana

Figure 3. Respondents’ choices of the type of product from ackee aril

REFERENCES [1] Ekué, MRM. Blighia sapida, ackee. Conservation and sustainable use of genetic resources of priority food tree species in sub-saharan africa. Bioversity International (Rome, Italy); 2011.

[2] Oyeleke GO, Oyetade OA, Afolabi F, Adegoke BM. Nutrients, Antinutrients and physiocochemical compositions of Blighia sapida pulp and pulp oil (Ackee apple). IOSR Journal of Applied Chemistry, 2013; 4(1): 5-8.

[3] Rashford J. Ackee poisoning and the evolutionary biology of Jamaica's ackee motif; 1997. Proceedings of the Thirtysecond Annual Meeting of the Caribbean Food Crops Society, Zamorana, Honduras, Central America, 713 July 1996. St Croix, US Virgin Islands: CFCS. pp. 185-192.

[4] Ulrich R. Destination Jamaica: the official visitor magazine of the Jamaica hotel and tourist association. Ulrich / communications Corp., Miami, Florida; 1998.

[5] Ekué, MRM, Sinsin B, Eyog-Matig O, Finkeldey R. Uses, traditional management, perception of variation and preferences in ackee (Blighia sapida K.D. Koenig) fruit traits in Benin: implications for domestication and conservation. Journal of Ethnobiology and ethnomedicine, 2010; 6:12.

[6] Lewis CB. Information Bulletin of the Scientific Research Council, 1965; 1: 12-14.

[7] ICRAF. Agroforestree Database: Blighia sapida. World Agroforestry Centre; 2009.

[8] Lancashire RJ. The Jamaican national fruit; 2004.

[9] Koenig KD. Blighia sapida Ann Bot (Konig and Sims), 1806; 2: 571, t. 16-17.

[10] Lancashire RJ. Jamaican Ackee; 2006.

[11] Ekué, MRM, Assogbadjo AE, Mensah GA, Codjia JTC. Overview: Ecological distribution and traditional agroforestry system around the ackee (Blighia sapida) in mid Sudanese in northern Benin. Bulletin of Agricultural Research of Benin, 2004; 44: 34-44.

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[12] Dossou MKR, Codji JTC, Biaou G. Role of forest resources Blighia sapida [13] SPSS (Statistical Package for Social Sciences). Application Guide. SPSS Inc.; 2008.

[14] Morton J. Akee, 1987; pp. 269-271. In: Fruits of warm climates. Julia FM, Miami Fl. (http:// www.hort.purdue.edu/newcrop/morton/akee.html) downloaded August, 2013.

[15] McDowell SAC, Walcott JA. A computational study of hypoglycin A, the toxin of the unripe Jamaican ackee fruit. Molecular Physics: An International Journal at the Interface Between Chemistry and Physics, 2011; 109(3): 397-405.

[16] Ashurst PR. Toxic substances of ackee. Review Journal of science resources council, Jamaica, 1971; 2: 4-16.

[17] Odutuga AA, Asemoto HN, Musac I, Golden KD, Kean EA. Fatty acid composition of arilli from ackee (Blighia sapida) fruit. Jamaican Journal of Science and Technology, 1992; 3: 30-32.

[18] Mitchell S, Seymour AW, Ahmad M. Ackee, Jamaica’s top fruit. Jamaican Journal of Science and Technology, 2008; 31: 84-89.

[19] Annongu AA, Joseph KJ, Adeyina AO, Wopetu VA. Investigation on some biochemical and histopathological indices in broiler chicks fed detoxified Blighia sapida seed meal in diets. African Journal of General Agriculture, 2010; 6(4): 295-300.

[20] Rashford J. Those that do not smile will kill me: the ethnobotany of the ackee in Jamaica. Economic Botany, 2001; 55(2): 190-211.

[21] Golden KD. Hypoglycin: a toxic amino acid of the ackee plant. Caribbean Poison Information Network (CARPIN) First Scientific Conference 2006 June; 3-4, [22] Golden KD, Williams JO, Bailey-Shaw Y. High–performance liquid chromatographic analysis of amino acids in ackee fruit with emphasis on the toxic amino acid hypoglycin A. Journal of Chromatographic Science, 2002; 40 (8): 441-446.

[23] Golden KD, Kean EA, Terry SI. Jamaican vomiting sickness: A study of two adult cases. Clin Chim Acta, 1984; 142 (3): 293-298.

[24] Kean EA, Hare ER. γ-Gutamyl transpeptidase of the ackee plant. Phytochemistry, 1980; 19(2): 199-203.

[25] Brown M, Bates RP, McGowan C, Cornell JA. Influence of fruit maturity on the hypoglycin A level in ackee (Blighia sapida). Journal of food safety, 1992; 12(2): 167-177.

[26] Singh P, Gardner M, Poddar S, Choo-Kang E, Coard K, Rickards E. Toxic effects of ackee oil ( Blighia sapida L.) following subacute administration to rats. West Indian Medical Journal, 1992; 41(1): 23-26.

[27] Rashford J.. A critique of Scott’s theory of the relationship between ackee seasonality and ackee poisoning. Tropical Fruits Newsletter, IICA, Trinidad, Newtown, 1999; 32: 7-10.

[28] Storozhenko S, Belles-Boix E, Babiychuck E, Herouart D, Davey MW, Slooten L, Montagu MV, Inźe D, Kushnir S. γ-Gutamyl transpeptidase in Transgenic Tobacco Plant. Cellular location, Processing and biochemical properties. Plant Physiol, 2002; 128: 1109-1119.

[29] Bowen C. Ackee – More than food. Gleaner Nov 24th; 2005. http://www.jamaicagleaner.com/ gleaner/20051124/eye/eye1.html [30] Baumer M. Trees, shrubs and shrubs foster care in West Africa Dakar, Senegal: Enda; 1999.

[31] Ambe GA. The fruit edible wild of Guinean savannahs of Cote d’Ivoire: state of knowledge by a local population, the Malinke. . Biotechnology, agronomy, Society and Environment, 2001; 5:43-58.

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Synthesis of Napthoquinone-Azoles as Potential Antibacterial Agents

1. Synthesis of Naphthoquinone-Azoles as Potential Antibacterial Agents Nadale Downer-Riley* and Latoya Wright Chemistry Department, University of the West Indies, Mona. Kingston 7, Jamaica, W. I. Fax: 876 9771835; Tel: 876 9271910; E-mail: nadale.downer02@uwimona.edu.jm

ABSTRACT: Naphthoquinone azoles and precursor compounds were synthesized and evaluated against E. coli and S. aureus using the disc diffusion technique. Among the compounds evaluated, 2,3-dichloronaphthoquinone, 2-acetamido -3-chloronaphthoquinone, 2-methylnaphth[2,3-d]oxazole-4,9-dione and methylnaphth[2,3-d]imidazole-4,9-dione were promising antibacterial prototypes.

INTRODUCTION Infectious diseases such as HIV/AIDS and tuberculosis are among the leading causes of death worldwide. Concomitant with the widespread use of existing antimicrobial drugs, there is growing resistance of common fungal and bacterial strains., For example, microbes have now displayed resistance to azole drugs, such as fluconazole and metronidazole, which are widely used in the clinical treatment of fungal and bacterial infections respectively (Figure 1)., This challenge within the medical field has propelled research towards the development of new and effective antimicrobial drugs with different modes of actions.

Various 1,4-naphthoquinone derivatives have been synthesized or isolated from plants, animals and fungi. The synthesis and evaluation of the antimicrobial activity of natural naphthoquinones such as juglone (3) and plumbagone (4) has been reported.5 Also the naphthoquinone derivative, atovaquone (5), is the chosen drug for treating pneumonia caused by Pneumocystis carinii. As a group, naphthoquinones display a vast range of biological activities including antitumor,-,, antibacterial, anti-

Figure 1: Examples of Antimicrobial Compounds inflammatory, antimalarial,, antiviral, radical scavenging, antiplatelet, trypanocidal, and antifungal activities., Although the mechanism of action has not been fully estab-

JAMAICAN JOURNAL OF SCIENCE & TECHNOLOGY, Volume 21-24 ISSN: 1016-2054 |

Synthesis of Napthoquinone-Azoles as Potential Antibacterial Agents lished, the wide range of bioactivities displayed by naphthoquinones is thought to arise from their ability to accept and transport electrons owing to the presence of the two ketone groups. Furthermore, the presence of a nitrogen atom at position 3 was reported to enhance antimicrobial activity of naphthoquinones.

In this context, the preparation of 1,4-naphthoquinone azole derivatives and the screening for antibacterial activity presented an attractive challenge. The compounds which were targeted included compounds of types 6-8 in

Figure 2: Targeted naphthoquinone azole systems which the naphthoquinone system is fused on to oxazole, imidazole and thiazole rings respectively (Figure 2). Although naphthoquinone azoles have not been widely studied, a few have been found to display activities inclusive of antifungal and antibacterial activity.-,, There are also several reports of the antifungal activity of precursor molecules and related compounds. It is worth mentioning that although some biological activity studies have been carried out on compounds possessing these frameworks, they have been primarily focused on antifungal activity and no comparative antibacterial study of these naphthoquinone azoles have been reported. By assessing the antibacterial activity of these azole systems as well as their precursors, a better understanding of which system possesses good antibacterial activity will be garnered which may be used to guide further studies in the area. In the present study, a preliminary investigation of the synthesis and antibacterial activity of these naphthoquinones is reported.

RESULTS AND DISCUSSION The literature has shown that dibromoquinones may be converted to quinone oxazoles by heating with the corresponding acid amide in ethylene glycol for 2 hours (to obtain the corresponding quinone amide) and then add-

ing 10% bicarbonate solution and heating for a further 8 hours. Synthesis of naphthoquinone oxazole 6a was first attempted from 2,3-dibromonaphthoquinone (10) by reaction with acetamide in ethylene glycol at reflux. However, neither the corresponding acetamide nor the desired oxazole 6a were isolated from this reaction Scheme 1).

An alternate route which involved the synthesis of the naphthoquinone oxazole from 2 -amino-3chloronaphthoquinone (12) has also been reported. The required aminonaphthoquinone (12) was prepared from dibromonaphthoquinone (10) over 2 straightforward and high-yielding steps. The dibromoquinone was first heated in refluxing ethanol with HCl over 3 hours and after isolation of the crystalline dichloride, it was reacted with ammonium hydroxide in ethanol yielding aminoquinone 12 (Scheme 1). Naphthoquinone oxazole 6a was then obtained in moderate yield by heating a mixture of aminoquinone 12 and sulphuric acid in acetic anhydride for 30 minutes.

Recognizing the similarities in the naphthoquinone derivatives, the possibility of a synthetic approach which involved a common intermediate was considered. Attempts to prepare naphthoquinone thiazole 8a from 2-amino-3chloronaphthoquinone (12), as reported in the literature, by reaction with sodium sulphide (to effect formation of the mercaptoquinone) then acetaldehyde in acetic acid were unsuccessful. We were however able to use compound 12 as a precursor to naphthoquinone imidazole 7a as shown in Scheme 1. Although the direct conversion of chloroquinone 12 to diaminoquinone 14 has been reported, the initial conversion to the acetamide before substitution by ammonia was found to be more practical. Once the diaminoquinone was obtained, then reaction with acetic anhydride in sulphuric acid at reflux yielded the desired naphthoquinone imidazole 7a.

Six compounds were screened for antibacterial activity by the disc diffusion method using Escherichia coli (Gram negative) and Staphylococcus aureus (Gram positive) in this initial investigation. The high incidence of S. aureus resistant strains at some hospitals in Jamaica coupled with the report of E. coli being the most common bacterial pathogen in Jamaican children with HIV/AIDS were key factors in choosing these organisms..

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Synthesis of Napthoquinone-Azoles as Potential Antibacterial Agents

Scheme 1: Synthesis of naphthoquinone derivatives

Six compounds were screened for antibacterial activity by the disc diffusion method using Escherichia coli (Gram negative) and Staphylococcus aureus (Gram positive) in this initial investigation. The high incidence of S. aureus resistant strains at some hospitals in Jamaica coupled with the report of E. coli being the most common bacterial pathogen in Jamaican children with HIV/AIDS were key factors in choosing these organisms., The antibacterial effect observed for compounds 11-14, 6a and 7a is presented in Table 1. It can be readily seen that compound 12, 2-amino-3-chloronaphthoquinone, showed no activity against the test organisms. E.coli and S.aureus respectively showed moderate sensitivity to dichloronaphthoquinone (11) and diaminonaphthoquinone (14). These findings were expected as there has been a previous report on the activity of compound 14 against S. aureus, with IC50 values ranging from 30 to 125 μg/mL. E. coli also showed high sensitivity towards compounds 13, 6a and 7a while S. aureus showed high sensitivity towards compounds 11 and 6a. Both organisms showed high sensitivity towards naphthoquinone 6a indicating that this compound is an ideal lead

Activity Against Test Compound 11 12 13 14 6a 7a

E. coli √

S. aureus √√

√√

√ √√

√√ √√

-

√: moderate activity; √√: good activity

Table 1: Antibacterial activity of naphthoquinone derivatives structure for the synthesis of other naphthoquinones which can be screened for antibacterial activity against a wider panel of microorganisms.

In conclusion, lead antibacterial naphthoquinones with good activity against E. coli and S. aureus have been prepared and identified. These structures will be used to

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Synthesis of Napthoquinone-Azoles as Potential Antibacterial Agents guide the preparation of a series of these compounds for more in-depth antibacterial screening. Additionally, quantitative data on the activity of the naphthoquinones are in the process of being completed.

EXPERIMENTAL The compounds synthesized were analyzed by thin layer chromatography (TLC) and the structures confirmed by 1H-NMR, 13C-NMR, IR and comparison wi8th literature melting points. NMR spectra (Bruker 200 and 500 MHz) were determined in CDCl3 solution and the resonances are reported in ppm downfield from TMS; J values are given in Hz. 2,3-Dibromonaphthoquinone (10) To a cold solution of naphthoquinone (5.6 g, 35.3 mmol) in acetic acid (30 mL) was added a solution of bromine (3.8 mL, 77.5 mmol) in acetic acid (20 mL) dropwise. The mixture was heated at reflux for 3 hours, poured on to crushed ice (150 mL), filtered and recrystallized from ethanol to yield the dibromoquinone as yellow needle-like crystals (12.4 g, 87%): mp 215-217 °C (lit. 218°C).

2,3-Dichloronaphthoquinone (11) To a mixture of ethanol (100 mL) and hydrochloric acid (15 mL) was added dibromoquinone 10. The mixture was heated at reflux for 3 hours, poured into water (300 mL), filtered and recrystallized from ethanol to provide the dichloroquinone as yellow crystals (100%): mp 195-197 ° C (lit.30 195 °C).

2-Amino-3-chloronaphthoquinone (12) To a solution of dichloroquinone 11 (5.8 g, 25.5 mmol) in ethanol (120 mL) was added 35% aqueous ammonia (12 mL). The mixture was heated at reflux for 30 minutes, concentrated and recrystallized from ethanol to provide the aminoquinone as an orange solid (5.3 g, 100%): mp 191-193 °C (lit.24 195-196 °C).

2-Methylnaphth[2,3-d]oxazole-4,9-dione (6a) To a solution of 2-amino-3-chloronaphthoquinone (0.5 g, 2.5 mmol) in acetic anhydride (5 mL) was added concentrated sulfuric acid (0.25 mL). The mixture was heated at reflux for 30 minutes, cooled, filtered and rinsed with cold ethanol to obtain the oxazole as fine brown crystals (0.36 g, 70%): mp 316-318 °C (lit. 317 °C).

2-Acetamido-3-chloronaphthoquinone (13) To a cold suspension of compound 12 0.030 g, 0.16 mmol) in acetic anhydride (0.5 mL) was added 1 drop of concentrated sulfuric acid. After stirring for 10 minutes, the yellow precipitate observed was filtered off and washed with ether (5 mL). The solid was recrystallized from ethanol to give yellow crystals (0.023 g, 69%): mp >250 °C (lit. 230 °C).

2,3-Diaminonaphthoquinone (14) To a solution of 2-acetamido-3-chloronaphthoquinone (13) (0.34 g, 1.35 mmol) in nitrobenzene (3 mL) was added 35% aqueous ammonia (2 mL). The mixture was heated at reflux for 1 hour, cooled and poured into hexane.

The solids were filtered and recrystallized from ethanol to provide the diaminoquinone as an orange solid (0.132 g, 61%): mp 288-289 °C (lit. 230 °C).

2-Methylnaphth[2,3-d]imidazole-4,9-dione (7a) To a solution of 2,3-diaminonaphthoquinone (0.09 g, 0.57 mmol) in acetic anhydride (1 mL) was added 1 drop concentrated sulfuric acid. The mixture was heated at reflux for 1 hour, cooled, poured into water and extracted into ethyl acetate. The mixture was concentrated and then rinsed with cold ethanol to obtain the imidazole (0.03 g, 25%): mp 235-237 °C (lit.24 368 °C).

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[14] Song, G. Y., Kim, Y., You, Y. J., Cho, H., Kim, S. H., Sok, D. E., and Ahn, B. Z. Naphthazarin derivatives (VI): synthesis, inhibitory effect on DNA topoisomerase‐I and antiproliferative activity of 2‐or 6‐(1‐Oxyiminoalkyl)‐5, 8‐dimethoxy‐1, 4‐naphthoquinones. Archiv der Pharmazie. 2000; 333(4): 87-92.

[15] Lien, J. C., Huang, L. J., Teng, C. M., Wang, J. P., and Kuo, S. C. Synthesis of 2-alkoxy 1, 4-naphthoquinone derivatives as antiplatelet, antiinflammatory, and antiallergic agents. Chemical and Pharmaceutical Bulletin. 2002; 50 (5): 672-674.

[16] Salmon-Chemin, L., Buisine, E., Yardley, V., Kohler, S., Debreu, M. A., Landry, V. and Davioud-Charvet, E. 2and 3-Substituted 1, 4-naphthoquinone derivatives as subversive substrates of trypanothione reductase and lipoamide dehydrogenase from trypanosoma c ruzi: synthesis and correlation between redox cycling activities and in vitro cytotoxicity. Journal of Medicinal Chemistry. 2001; 44(4): 548-565.

[17] .Tandon, V.K., Singh, R.V. and Yadav, D.B. Synthesis and evaluation of novel 1, 4-naphthoquinone derivatives as antiviral, antifungal and anticancer agents. Bioorganic & Medicinal Chemistry Letters. 2004; 14(11): 2901–2904.

[18] Santos, M.M.M., Faria, N., Iley, J., Coles, S.J., Hursthouse, M.B., Martins, M.L. and Moreira, R. Reaction of naphthoquinones with substituted nitromethanes. Facile synthesis and antifungal activity of naphtho [2, 3-d] isoxazole4, 9-diones. Bioorganic & Medicinal Chemistry Letters. 2010; 20(1): 193–195.

[19] O'brien, P. J. Molecular mechanisms of quinone cytotoxicity. Chemico-biological Interactions. 1991; 80(1): 1-41.

[20] Tandon, V. K., Yadav, D. B., Singh, R. V., Vaish, M., Chaturvedi, A. K. and Shukla, P. K. Synthesis and biological evaluation of novel 1, 4-naphthoquinone derivatives as antibacterial and antiviral agents. Bioorganic & Medicinal Chemistry Letters, 2005; 15(14), 3463-3466.

[21] Sasaki, K., Abe, H., and Yoshizaki, F. In vitro antifungal activity of naphthoquinone derivatives. Biological & Pharmaceutical Bulletin. 2002; 25(5), 669-670.

[22] Schellhammer, C. W., Petersen, S. and Domagk, G. Naphthoxazolequinone as an antituberculosis agent. Naturwissenschaften . 1959; 46, 81-2.

[23] Babu, B. H., and Rao, N. V. S. Synthesis of some substituted naphtho[2,3-d]thiazole-4,9-diones as potential fungicides. Current Science. 1967; 36(7): 176.

[24] Hoover, J. R., and Day, A. R. Preparation of some imidazole derivatives of 1, 4-naphthoquinone. Journal of the American Chemical Society. 1954; 76(16): 4148-4152.

[25] Hammam, A. S., Youssef, M. S. K., Radwan, S. M. and Abdel-Rahman, M. A. Synthesis of a new Diels-Alder quinone adduct and its use in preparing thiazolo-and oxazoloquinolines. Bulletin-Korean Chemical Society. 2004; 25 (6): 779-785.

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Synthesis of Napthoquinone-Azoles as Potential Antibacterial Agents [26] Rathelot, P., Njoya, Y. and Maldonado, J. Preparation of 2-substituted naphth [2, 3-d] oxazole-4, 9-diones via a radical chain process. Heterocycles 2000; 53(5): 1075-1084.

[27] Brown, P. D. and Ngeno, C. Antimicrobial resistance in clinical isolates of Staphylococcus aureus from hospital and community sources in southern Jamaica. International Journal of Infectious Diseases. 2007; 11(3), 220-225.

[28] Byam P.R., Pierre R.B., Christie C.D.C., Andiman W.A. and Pettigrew M. Antibiotic resistance among pathogens causing disease in Jamaican children with HIV/AIDS. West Indian Medical Journal. 2010; 59(4): 386-392.

[29] Aly, A. A., Ishak, E. A., Alsharari, M. A., Al窶信uaikel, N. S. and Bedair, T. M. (2012). Aminonaphthoquinones in heterocyclization. Journal of Heterocyclic Chemistry. 2012; 49(1): 9-20.

[30] Ebine, S. 3, 4-Benzotropolone and related compounds, III. Nitration of 3, 4-benzotropolone. Bulletin of the Chemical Society of Japan. 1962; 35(1): 122-124.

[31] K. Fries and P. Ochwat. New (observations) on 2,3-dichloro-1,4-naphthoquinone. Berichte der Deutschen Chemischen Gesellschaf. 1923; 56(B): 1291-1304.

[32] Efimova, G. A. and Efros, L. S. Heterocyclic derivatives of substituted 1,4-Naphthoquinones. IV Condensation of 2,3-diamino-1,4-naphthoquinone and its monomethyl derivative with 1,3-diketones. Zhurnal Organicheskoi Khimii. 1967; 3(1): 162-8.

[33] Medina, L. F., Stefani, V. and Brandelli, A. Use of 1, 4-naphthoquinones for control of Erwinia carotovora. Canadian Journal of Microbiology. 2004; 50(11): 951-956.

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Research in Progress Our Young Scientists’ Abstracts Uncommon Fruit Species of Jamaica: Potential for Improved Health & Economic Conditions Camille Stacey Ann Bowen Forbes University of the West Indies, Jamaica Lifestyle diseases have for decades been the principal public health challenge for Jamaica, with diabetes, cancer and cardiovascular disease being leading causes of death. Scientific evidence demonstrates that alterations in diet have strong effects on health throughout life.

Over the last few decades, there has been increased interest and focus on fruits and their role in prevention of chronic non-communicable diseases. Although Jamaica is among the most fruitful countries of the world, many of our edible fruit species are unknown by the masses, resulting in their exclusion from the diet, and their non-exploitation with respect to cultivation and use in research and food and nutraceutical product development. With a view of promoting productive utilization of this natural resource, we have conducted basic and applied research on several fruit species, aimed at investigating their health-beneficial properties- particularly their antioxidant, antiinflammatory, anti-diabetic and anticancer properties.

The fruit species investigated include four berries species from the Rubus genus (three raspberries and one blackberry) and a guava species (strawberry guava Psidium cattleianum). Our research led to the discovery that there are two different varieties of red raspberries in Jamaica. To date, only one variety has been described. These berry species have exhibited significant differences in their phytochemical profiles. We are, in collaboration with other researchers, currently in the

process of comparing the morphology and DNA profiles of the two varieties. To date, our results have showed that the Jamaican berries possess high antioxidant activities and levels of anthocyanins, comparable to those found in similar commercial varieties sold worldwide. Extracts of the Jamaican berries demonstrated superior anti-inflammatory and anticancer properties compared to their counterparts. Additionally, extracts and compounds from the red and yellow raspberries (respectively R. rosifolius and R. ellipticus) showed anti-proliperative activity against several cancer cell lines including colon, breast and stomach cancers. Strawberry guava exhibited significantly greater vitamin C content, antioxidant activity and total polyphenolics content relative to common guavas (Psidium guajava). A compound from a berry extract have demonstrated greater antidiabetic activity than a commercial drug, and is therefore a potential pharmaceutical candidate. We have extended the study to include the leaves of the Rubus plants, with the view of uncovering their potential for producing herbal teas and other nutraceutical products. The tea extracts, as well as organic leaf extracts, have demonstrated high antioxidant activity, and are good sources.

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Investigating the Economic Potential of Jamaican Ackees Andrea Goldson Barnaby

University of the West Indies, Jamaica

Ackee has significant export potential. Research was conducted on the fatty acid profile of the different portions of the fruit. This was performed as there are currently concerns about previously reported high levels of linoleic acid being present in the fruit which was further linked as a potential risk factor implicated in the high levels of prostate cancer in Jamaican males. Knowledge of the fatty acid profile of the fruit is also important with regards to heart health and the stability of the oil.

Ackee is widely consumed by Jamaicans. Knowledge of the lipid profile of the fruit is therefore important.

From the research conducted, a facile method of predicting the presence or absence of linoleic acid in extracts of the fruit has identified, the acid value and iodine value of the oil determined as well as the levels of monounsaturation versus polyunsaturated fatty acid.

The major triacylglycerol present within extracts of teh fruit was also identified. Utilization of the waste generated from the ackee industry was also explored. Ackee has the potential of being considered a golden crop being a significant foreign exchange earner. Cryogenic freezing of the ackee fruit as an alternative processing methods of the fruit was also investigated

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Endemic Plants in the Cockpit Country: Jamaica’s Treasure Andrew S. Lamm*, O’Brien K. Brown and Debbie Ann Gordon Smith University of Technology, Jamaica

The Cockpit Country is one of the last remaining areas of primary forests in Jamaica and is known for its rich biodiversity, history and geomorphology. This area has a large number of plants, animals and microorganisms which are found nowhere else in the world. It is also a major water catchment area and thus a vital source of rivers, streams and wells on both sides of the island. The natural resources of the region are also an integral part of the Jamaica’s heritage, cultural and ethnomedicinal legacy. The Cockpit Country region is currently under threat from bauxite and other mineral mining operations; uncontrolled agricultural practices; invasive species; and the effects of global climate change. This presentation will highlight some medicinal potential of the plants in the region and seeks to promote the preservation of the area through such discoveries. We will show the ongoing work of the Natural Products Research Laboratory in the areas of drug discovery, education, preservation and collaboration in relation to the Cockpit Country.

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Potential of Two Jamaican Essential Oils against Mosquitoes and Bacteria Chenielle M Delahaye McKenzie, Sylvia Mitchell and Dwight Robinson

University of the West Indies, Jamaica

The antimicrobial and insecticidal properties of Callistemon viminalis (bottle brush) and Cymbopogon citratus (lemon grass) is being studied. The results are extraordinary and have the potential to grow as a viable business. C. viminalis and lemon grass essential oils and essences were extracted using a steam distiller apparatus. The essential oils were separated from their essences and tested against three pathogenic bacteria (Staphylococcus aureus, Streptococcus pyogenes and Escherichia coli) using the disc diffusion and tube dilution assays. The insecticidal potential of both essential oils was investigated using an olfactometer-based, spatial repellency bioassay with adult mosquitoes (Aedes aegypti). Both essential oils were very effective inhibitors of microbes producing inhibition zones of > 20 mm and MIC of 0.008 mg/ml against S. aureus. In the spatial repellency assay, the mosquito showed a high mortality and repellancy percentage in response to the essential oils of both C. viminalis and C. citrates, with a spatial activity index ranging from 0.27 to 0.77. Based on these findings products derived from these extracts should be in great demand in Jamaica and the wider world.

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Jamaican Journal of Science & Technology Volume 25 | December 2014 | Pages 2-31 JJST ISSN: 1016-2054 Published by: The Scientific Research Council, Information Services Division, Hope Gardens Complex, Kingston 6, Jamaica W.I.