Tuesday, August 6, 2013

Sugars, Sugar Alcohols, and Sweet Taste

Long before we could simply buy foods from a grocery store, our ability to detect the presence of sugars in foods was critical to our survival as a species.  We as humans have evolved to recognize sugary foods as tasting "good," because they are nutrient dense (high in calories) and "good" for us to eat, though today that's not entirely true.   Rather, sugary foods used to be good for us to eat long ago when we were hunting and gathering in the wild.  Back then, we needed the extra calories to survive.  Today, however, many of the foods that we eat are very nutrient dense and have many calories in the form of fat, protein, or sugar.  Sugar is far more prevalent now that we know how to refine and process it on an industrial scale.  Most of us don't really need to gather fruits to get sugar in our diet.  We can just buy a Snickers bar off the shelf at any convenience store. 

This abundance of sugar has made life easier and tastier, but it has also come at a cost.  Increased sugar consumption contributes to the world-wide epidemics of obesity and diabetes.  As a result, there has been a lot of research effort into the development of artificial sweeteners and other products than can cut calories from food.  Sugar substitutes have the potential to positively impact world-wide health and save billions of dollars of healthcare costs per year.  Obesity leads to cardiovascular and liver diseases as well as type 2 diabetes mellitus. 

There are also less altruistic but equally valid reasons for developing artificial sweeteners.  Another major goal is to cut costs in food and beverage manufacturing.  Consider a product like soda, where the major components are water and sugar, often in the form of high fructose corn syrup.  An alternative to sugar that tastes the same but costs less to produce could save companies millions or billions of dollars per year.

When most people think of artificial sweeteners, we first think of diet soda, which is sweetened by artificial chemicals such as apartame, acesulfame potassium (acesulfame K), and/or sucralose.  Many of the products that we consume also contain artificial sweeteners known as sugar alcohols, though they don't get a lot of attention and many people have probably never heard of them.  Let's explore a bit about sweet taste, sugars, and sugar alcohols after the jump....

Three common monosaccharides (shown in linear form)
There are many naturally-occurring sugars that your body can use for an energy source.  Your body processes (metabolizes) these sugars by breaking them down to get energy in the form of ATP molecules.  There are two types of sugars, simple and complex.  Complex sugars are made up of two or more simple sugars.  Simple sugars are also known as monosaccharides (mono for one, saccharide for sugar).  The primary simple sugar in human biology is glucose, the sugar found in your blood and primarily utilized by your body for energy.  Other simple sugars include fructose, found in fruits and vegetables, and galactose, found mainly in milk.  The monosaccharides shown above are in the "linear" form, but sugar molecules can react with themselves in the presence of water and form ring structures.  They typically flip back and forth between the linear form and the ring form, as shown for glucose and fructose below.    

Glucose, fructose, and sucrose, shown in ring form
A complex sugar made up of two monosaccharides is called a disaccharide (di for two).  Lactose is the primary sugar found in milk, and is made up of one glucose molecule convalently linked to a galactose molecule.  The table sugar that we use in cooking is sucrose, which is made up of one molecule of glucose and one molecule of fructose joined together.   Your body can only utilize monosaccharides to make energy, so when you eat a disaccharide like sucrose, your body has to first break it down into its monosaccharide components using enzymes secreted in the gastrointestinal (GI) tract.  

But the first place that your body detects sugars in your mouth, through the sweet taste receptors on the surface of certain cells on your tongue.  There's only one type of sweet taste receptor that we know of, but it can detect multiple types of monosaccharide and disaccharide sugars.  The ability of the sweet taste receptor to detect multiple types of sugar structures is going to be important when we discuss artificial sweeteners.   

When the sweet receptors detect sugar, they stimulate taste cells to send a signal to nerves that connect to your brain.  The exact neural pathways that sweet taste activates in your brain are complex, but they include reward pathways that affect our responses to sweet taste.  Studies have suggested that sweet taste may activate similar reward centers of the brain as those that are activated by opioid drugs or by alcohol in the brains of alcoholics.  This serves to reinforce our preference for sweet tastes.  Genetic variations in sweet taste receptors and/or neural pathways in the brain may create differences in individual preference for sweet foods similarly to how genetic differences are thought contribute to susceptibility to alcoholism or drug addiction.  The neurology and psychology of sweet taste is an active area of research, because sweet taste preferences may have important implications for sugar consumption and thus obesity or diabetes.     

Creating an artificial sweetener is a pretty cool concept when you think about it.  The evolutionary purpose of sweet taste is to identify nutrient-rich foods like fruits.  The goal of an artificial sweetener is to trick your body, specifically the cells with the sweet taste receptors on your tongue, into thinking something is nutrient dense by activating the sweet receptors on the sweet-taste-responsive cells on your tongue.  In reality though, the ideal artificial sweetener is a molecule that our bodies can't metabolize very well or can't absorb and thus can't derive much energy from. 

Two artificial sweeteners that are very different in structure from sugars
Many artificial sweeteners have dramatically different structures than real sugars.  A prime example are the sweeteners acesulfame potassium (acesulfame K) and aspartame.  Many people are familiar with aspartame and acesulfame-K because they are used to various extents in diet sodas and other "sugar-free" products.  Aspartame is sold under the brand names NutraSweet® and Equal®.  Despite the fact that they have chemical structures that are very different from sugars, they can still activate the sweet taste receptors found on your tongue.  This is because the sweet taste
Soda can showing aspartame and acesulfame K as ingredients
receptors on the tongue can bind to and be activated by many different types of chemical structures, and it just so happens to be able to be activated by both of these compounds.  When acesulfame K and aspartame were first discovered was no logic to predicting that they would be "sweet."  That part of their discovery was completely accidental, and the main reasons for originally synthesizing them were quickly eclipsed by their potential as artificial sweeteners.     

Three chloride atoms distinguish sucrose from sucralose
However, sometimes only subtle changes in a sugar molecule can drastically alter both its sweetness as well as its metabolism.  Sucralose is the classic example of this.  Sucralose was discovered while chemists were specifically testing derivatives of sucrose, though its identification as an exceptionally sweet compound was still made by an accidental tasting.  Sucralose is about 600 times sweeter than sucrose, and it is very chemically stable.  Because of the replacement of three hydroxyl (OH) groups with chloride atoms (Cl), your body can't absorb or metabolize it and thus can't get any calories out of it.  At the same time, the slightly different change in structure makes it bind much more tightly to the sweet taste receptor, and thus it tastes much more sweet to you.

Sucralose was first approved for use in the US in 1998, and its use has exploded since then.  Thousands of sweet beverages, candy, and baked goods contain sucralose, often under the brand name Splenda®.  Many people say that sucralose has less of an "artificial" or "metalic" flavor than some other artificial sweeteners.  Part of this is due to cross-reactivity of some artificial sweeteners with other types of taste receptors.  For example, aspartame is also a weak activator of some types of bitter taste receptors, and thus it can impart undesirable tastes along with the sweetness.  Sucralose has much less cross reactivity with other receptors because its structure is much more similar to a real sugar.  Also, because it is sweeter than many other artificial sweeteners, much less of it can be used to achieve the desired sweetness.

While the safety of some "non-nutritive sweeteners" like aspartame has been disputed by some, there is little hard scientific or clinical evidence to support any toxicity in humans at present.  One health concern is that the use of non-nutritive sweeteners can lead to increased consumption of calories by other means.  For example, someone may feel that drinking a diet soda gives them the dietary leeway to eat a candy bar, too, and thus they end up consuming even more calories in the end.  In fact, some studies have linked consumption of "high-intensity" sweeteners like aspartame or sucralose is correlated with increased levels of diabetes and obesity, which may be due to alterations in eating patterns or the ability to interpret or predict the calorie content of foods that due actually contain sugar.  In other words, drinking soda sweetened with hyper-sweet aspartame make make a candy bar sweetened with real sugar not seem so sweet, which may make people think candy bars aren't so bad and that they can eat more.  More research is needed to really tease out how artificial sweeteners affect us, but the American Heart Association and American Diabetes Association stress that limitation of added dietary sugars is a key component of diabetes, obesity, and cardiovascular disease management; non-nutritive sweeteners may indeed have a benefit if they are used in this role as part of a well structured diet.    
Sorbitol is made by the reduction of glucose
Another type of artificial sweetener that people might not be as familiar with are the sugar alcohols, sometimes called polyols.  Sorbitol is a sugar alcohol derived from glucose.  You can see in our diagram of glucose and sorbitol that there is very little difference between the two molecules.  Sugar alcohols are created by the replacement of aldehyde group (containing the double-bonded oxygen shown at the top of the glucose molecule) with a hydroxyl (OH) group.  Speaking chemically, we would say that the aldehyde group is reduced to a hydroxyl group.  In chemistry, an alcohol is any molecule that contains a hydroxyl group bound to a carbon atom.  The type of alcohol molecule that you probably first think of is ethanol, which is the alcohol in wine, liquor and bear, but lots of other types of alcohols exist, and sugar alcohols will not get you drunk.  The conversion of the aldehyde in glucose to the hydroxyl in sorbitol, while seemingly a subtle change, prevents your body from metabolizing sorbitol as efficiently as glucose.   

Some sugar alcohols are produced naturally, but most of the ones used today are chemically derived from sugars.  Thus, most sugar alcohols actually cost more to produce than sugars.  Also, because their sweetness is often not as "high intensity" as other artificial sweeteners like sucralose, more sugar alcohols have to be used to achieve the same relative level of sweetness as other compounds like sucralose and aspartame.  While not as "cost effective" per se, the use of sugar alcohols has many other benefits that we'll discuss below.  

Xylitol is one of the most common sugar alcohols used.  Because it is almost twice as sweet than sorbitol, it is a more attractive ingredient because less of it needs to be used.  Xylitol is considered to be "isosweet" (the same sweetness; iso = the same) as sucrose, while sorbitol is only 50-80% as sweet as sucrose.  Xylitol naturally occurs in very small amounts in certain fruits and vegetables as well as in our own bodies as an intermediate (or a short-lived product that gets converted into something else) in a biochemical pathway called the glucuronic acid cycle, also called the uronic acid pathway.  The glucuronic acid cycle is important because it converts glucose into a reactive form of glucuronate (UDP-glucuronate) that can be used to detoxify foreign substances in the liver as well as to build or break down a class of chemicals called mucopolysaccharides (also called glycosaminoglycans) such as heparin and hyaluronic acid.

Most of the xylitol found in food and pharmaceuticals is made from xylan, a polysaccharide made from long chains of a monosaccharide called xylose that is found in trees and other plants.  Xylitol has been approved in the US as a "food additive" for special purposes since 1963, but its use is limited, because it is more expensive to produce than other artificial sweeteners. However, it is a mainstay of sugar free gum and mouthwashes, and has beneficial effects for oral health that we'll describe later on.   In other countries, xylitol has more widespread use.  In some areas, sugar substitutes that are sold for baking that are nearly 100% xylitol. 

Hermann Emil Fischer
In 1891, the German chemist Emil Fischer first isolated xylitol from beech chips.  Fischer later went on to receive the second Nobel prize in chemistry in 1902 for his work on sugars. He was a brilliant scientist who made many contributions to organic chemistry as well as science education in Germany, but later in his life he became heavily involved in chemical production to support the German war effort in World War I. He was driven to depression by the enormous human costs of the war, which included one of his own sons who was killed in action and another who committed suicide during the war.  Emil Fischer committed suicide in 1918, but because of his legacy of discovery in organic chemistry, monuments and honors to him in Germany survive to this day.  Independently of Fischer in 1891, the French chemist M.G. Bertrand also isolated xylitol from wheat and oat straw, so the discovery of xylitol is usually credited to both men.  

For many decades after xylitol was discovered, no one was very interested in it. It wasn't until the 1960s that the use of xylitol as a food and drug additive began to get serious study, and the use of xylitol has exploded in recent years.  Xylitol is used as a sweetener in products such as sugar-free candy and gum, but also in other "low carb" or "low calorie" products such as muffins and cookies. Additionally, it is found in a countless number of pharmaceuticals, from cold medications to toothpastes to mouthwashes.

One of the main benefits is that sugar alcohols like xylitol and sorbitol (another common ingredient in sugar-free gum) are not able to be fermented by bacteria in the mouth.  Xylitol may actually inhibit the ability of these bacteria to metabolize other sugars.  When one of the most common oral bacteria, Streptococcus mutans, tries to metabolize xylitol, enzymes in the bacteria phosphorylate it to xylitol-5-phosphate; different bacterial enzymes then convert xylitol-5-phosphate back to xylitol, creating a futile "energy wasting" metabolic cycle.  Xylitol may also inhibit the fermentation of Streptococcus mutans and other bacteria by inhibiting key bacterial enzymes as well.  Thus, using xylitol or sorbitol as a sweetener does not contribute to and may actually inhibit bacteria growth, plaque build-up, and formation of cavities.  Interstingly, though, because of this, xylitol cannot be used as a sweetener in products containing yeast, like sweet breads, as xylitol is also a potent inhibitor of yeast fermentation and growth.

Xylitol also absorbs heat as it dissolves in water, an endothermic (or heat absorbing) reaction.  As a result, products with crystalline xylitol can also create a pleasant cooling affect that fits very well in a minty chewing gum or mouthwash. Furthermore, xylitol may be able to associate with calcium ions and contribute to tooth remineralization, possibly giving it an added benefit in dental products like gum and toothpaste.  Further research is needed to more fully understand this role of xylitol.   

For the most part, xylitol is extremely safe in humans. Xylitol is very slowly absorbed in the human intestine. This is because there is no "natural" transport system for you to absorb the xylitol.   None of the proteins involved in sugar transport across the intestinal epithelium recognize xylitol as efficiently as they recognize naturally occurring sugars.   When you ingest xylitol, you typically only absorb about one third of it, with the rest being metabolized by the gastrointestinal microbes that populate your gut.  Through fermentation, they turn the xylitol into gasses (carbon dioxide, hydrogen, and methane) as well as short chain fatty acids that you can then more efficiently absorb.  However, because of the poor and slow absorption of xylitol, high doses (less than 50 grams for the average person) can cause diarrhea because it draws water out of the intestines through osmosis.  Also, the fermentation of xylitol and gas build up can create bloating in some people if enough xylitol is ingested.    

The xylitol that you do absorb is converted in the liver first to D-xylulose and then to fructose-6-phosphate, which your body can then more readily metabolize to glucose and derive energy from.  A given amount of xylitol has approximately 40% fewer calories than an equal amount of sucrose.  However, the incomplete absorption of xylitol also contributes to lowering its calorie content even further.  Also, because the absorption of xylitol and conversion of xylitol to glucose is slow in humans, the ingestion of xylitol does not cause a detectible increase in blood glucose as see when natural sugars like sucrose or glucose are consumed.  The glycemic index is a relative measure of how fast blood glucose levels increase after ingestion of certain foods.  The glycemic index of xylitol is over 10 times lower than that of glucose.  Because of this, xylitol does not cause significant levels of insulin secretion in humans.

Blood sugar levels are controlled by the release of insulin from the pancreas.  After a meal, when nutrients are absorbed, your blood sugar concentration increases.  This stimulates certain cells (beta cells) of the pancreas to release insulin. Insulin is a hormone that tells the cells of your body to take up sugar; when they do, this then lowers the concentration of sugar in your blood.  The condition of elevated blood sugar is called hyperglycemia (hyper = more or above normal), while the condition of lowered blood sugar is called hypoglycemia (hypo = less or below normal).  In diabetic patients, defects in insulin release or in the sensitivity of their cells to insulin results in elevated blood glucose (hyperglycemia), which can cause damage over time. Because of the lower calorie content and minimal effect of xylitol on insulin release, xylitol is also used in sugar-free candies marketed toward diabetics.
All-in-all, the discovery and use of xylitol has had pretty positive effects for humans.  However, there is a hidden danger to xylitol that many people don't know about.  Xylitol is extremely toxic to dogs, as we mentioned in a previous blog post.  Unlike humans, dogs can rapidly absorb xylitol in their gastrointestinal tract.  Peak absorption occurs after only 30 minutes.  Once ingested and absorbed by the dog, xylitol stimulates  insulin secretion that is about 6 times greater than that seen after ingestion of an equal amount of glucose.  Ingestion of large amounts of xylitol (greater than 0.1 gram per kilogram of bodyweight) can cause rapid-onset lowering of blood sugar (hypoglycemia) due to insulin release in the absence of a real increase in blood glucose.  Insulin secretion can start after as little as 20 minutes after ingestion, though it depends on the type of product ingested by the dog and how much the dog actually chews it, as slow release of the xylitol can lead to symptoms of hypoglycemia or liver toxicity taking as long as 12 hours to appear.  The exact reason why xylitol stimulates insulin secretion in dogs (as well as cows, goats, and rabbits) but not humans (or rats and horses) is unknown, but some studies have suggested that xylitol directly stimulates pancreatic beta cells of dogs to secrete insulin.

Higher doses of xylitol (greater than 0.5 gram per kilogram of bodyweight) can also cause liver damage (hepatotoxicity) in dogs.  The exact mechanism of this is also not very well understood, though it is thought that reactive byproducts (free radicals or reactive oxygen species) produced during the metabolism of xylitol may be damaging to liver cells.  Also, as liver cells try to break down xylitol, these cells may become depleted of ATP and energy, a condition that can lead to necrosis, a type of cell death.

It is not surprising that the curiosity and indiscriminate appetite of dogs results in dogs accounting for over 70% of potential poisoning cases seen by vets.  If you have a dog and suspect that he or she ate something containing xylitol, the safest thing to do is call your vet, even if there are no immediate symptoms.  Some dogs require monitoring to make sure that delayed-onset symptoms do not appear.  When there are symptoms (vomiting, decreased blood glucose, lethargy, altered liver enzyme levels, or even seizures), vets can treat the dogs and the prognosis is good. We previously discussed several food that are toxic for pets in a previous blog post, and likewise dog owners have to be aware of the danger of xylitol to dogs and be aware of what their dog eats so that if their dog eats something with xylitol, they can let their vet know that this could be the cause of their dogs symptoms.

Cakes, cookies, gum, or any other product made from xylitol are potently toxic to dogs. There's not good evidence that xylitol has the same type of toxicity in cats, though there are case reports of cats developing hypoglycemia after ingesting xylitol. While xylitol may or may not be safe for cats, the best strategy is still to keep xylitol-containing products away from all pets.  Synonyms for xylitol that might be used on some labels include Eutrit, Kannit, Klinit, Newtol, xylite, Torch, or Xyliton.  While the science behind xylitol and its use in food and pharmaceuticals has may health benefits for humans, we also have to be aware of the potential danger to our furry four-legged friends.

Text © 2013 TheMadScienceBlog.com; Images are public domain. 

Sources and Further Reading
  • B.A. Burt.  "The Use of Sorbitol- and Xylitol-Sweetened Chewing Gum in Caries Control."  Journal of the American Dental Association.  2006.  137:190-196. 
  • C. Gardner, J. Wylie-Rosett, S. Gidding, L.M Steffen, R.K. Johnson, D. Reader, A.H. Lichenstein.  "Nonnutritive Sweeteners: Current Use and Health Perspectives: A Scientific Statement from the American Heart Association and the American Diabetes Association."  Circulation.  2012.  126:509-519.
  • E. Green and C. Murphy.  "Altered Processing of Sweet Taste in the Brain of Diet Soda Drinkers."  2012.  Physiology and Behavior.  107:560-567. 
  • Y. Hirata, M. Fujisawa, H. Sato, et al.  "Blood Glucose and Plasma Insulin Responses to Xylitol administered intravenously in Dogs."  Biochemistry and Biophysics Research Communications.  1966.  24:471-475.    
  • N. Kovalkovicova, I. Sutiakova, J. Pistl, and V. Sutiak.  "Some Food Toxic for Pets."  Interdisciplinary Toxicology.  2009.  2:169-176.   
  • T. Kuzuya, Y. Kanazawa, K. Kosaka.  "Plasma Insulin Response to Intravenously Administered Xylitol in Dogs."  Metabolism.  1966.  15:1149-1152.  
  • T. Kuzuya, Y. Kanazawa, K. Kosaka.  "Stimulation of Insulin Secretion by Xylitol in Dogs."  Endocrinology.  1969.  84:200-207.  
  • T. Kuzuya, Y. Kanazawa, M. Hayashi, et al.  "Species Differences in Plasma Insulin Responses to Intravenous Xylitol in Man and Several Mammals."  Endocrinologia Japonica.  1971.  18:309-320.  
  • K.A. Ly, P. Milgrom, and M. Rothen.  "Xylitol, Sweeteners, and Dental Caries."  Pediatric Dentistry.  2006.  28:154-163.
  • K.K. Makinen. "The Rocky Road of Xylitol to its Clinical Application."  Journal of Dental Research. 2000.  79:1352-1355.
  • R.D. Mattes and B.M. Popkin.  "Nonnutritive sweetener consumption in humans: effects on appetite and food intake and their putative mechanims."  American Journal of Clinical Nutrition.  2009.  89:1-14.  
  • M.S. Mellema.  "Xylitol."  Chapter 83 in Small Animal Toxicology, Third Edition.  Eds. M.E. Peterson and P.A. Talcott.  Elsevier: St. Louis, MO USA.  
  • L.A. Murphy and A.E. Coleman.  "Xylitol Toxicosis in Dogs."  Veterinary Clinics of North America: Small Animal Practice.  2012.  42:307-312.  
  • M.E. Peterson.  "Xylitol."  Topics in Companion Animal Medicine.  2013.  28:18-20.  
  • A. Pihlanto-Leppala, E. Soderling, K.K. Makinen.  "Expulsion mechanism of xylitol-5-phosphate in Streptococcus mutans."  Scandinavian Journal of Dental Research.  1990. 98:112-119.  
  • A. Raben and B. Richelsen.  "Artificial Sweeteners: A Place in the Field of Functional Foods? Focus on Obesity and Related Metabolic Disorders."  Current Opinion in Clinical Nutrition and Metabolic Care.  2012.  15:597-604.   
  • D.R. Reed, T. Tanaka, and A.H. McDaniel.  "Diverse Tastes: Genetics of Sweet and Bitter Perception."  Physiology and Behavior.  2006.  88:215-226
  • S.S. Schiffman and C.A. Gatlin.  "Sweeteners: State of Knowledge Review."  Neuroscience and Biobehavioral Reviews.  1993.  17:313-345.
  • P. Shankar, S. Ahuja, and K. Sriram.  "Non-Nutritive Sweeteners: Review and Update."  Nutrition.  2013.  In Press.  http://dx.doi.org/10.1016/j.nut.2013.03.024  
  • S.E. Swithers.  "Artificial Sweeteners Produce the Counterintuitive Effect of Inducing Metabolic Derangements."  Trends in Endocrinology and Metabolism.  2013.  In Press.  http://dx.doi.org/10.1016/j.tem.2013.05.005 
  • P.A. Temussi.  "New Insights into the Characteristics of Sweet and Bitter Taste Receptors."  International Review of Cell and Molecular Biology.  2011.  291:191-226.
  • P.A. Temussi. "The Sweet Taste Receptor:A Single Receptor with Multiple Sites and Modes of Interaction."  Advances in Food and Nutrition Research.  2007.  53:199-239.   


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    i am so happy to share this testimony with the world because generally there are so many doubts about the cure of hpv and cancer This is real take it serious, i am so happy that today i can give this testimony to the world and also help in savinglife of people who has been condemned for death just as i was ,who will believe that a herbs can cure hpv and cancer completely from thebody, i never believe that this will work, i have spend a lot of money getting drugs from the hospital to keep me healthy, it got to a time that all i was waiting for is death to come because i was broke and i already have strong outbreaks from the hpv, one day i was going through the internet asking questions online just to know more about the latest development in the medical sector to see if there is still hope then i stumbled on a post about about this great man called Dr. Ehiagwina through a publicly made a testimony on how she was also cured of ALS by this herbal doctor who is well known for his strong ancient herbal practice at first i doubted both the woman and the doctor just as so many that see's this post would doubt because medically it has been proven impossible but later i decided to give him a try so i emailed him I did not believe him that much, I just wanted to give him a try, he replied my mail and Needed some Information about me, then I sent them to him, he prepared a herbal medicine and sent it through Courier Service for delivery, he gave my details to the Courier Office. they told me that 3-5 days I will receive the package and after receiving it, i took the medicine as prescribed by him at the end of 13days that the medicine lasted, he told me to go to the hospital for a test, and i went, surprisingly after the test the doctor confirm me hpv negative and cancer disappear i thought it was a joke, i went to other hospitals and was also negative the doctors were speechless and i said it was a miracle, thank you sir for saving my life even if you cannot see this post i shall never stop testifying the impact you made in my life by restoring back my life when i was being stigmatized and even avoided by family and friends , I promise I will always testify of your good works. Dr. Ehiagwina contact: ehiagwinaherbalhome@gmail.com OR call +2348162084504 you can also add him on whatsapp.