Sugar that’s not sugar?

A couple of days ago I was catching up with last Sunday’s Dragon’s Den. For the non-Brits out there, this is a show in which entrepreneurs pitch business ideas to a panel of ‘dragons’ – i.e. successful business people – to get an investment of money and, perhaps more importantly, expertise and contacts. It’s a great show that’s been running for quite a few years now and has resulted in a number of products and brands becoming household names – in the UK anyway.

LinusGorpeDragonsDen

Linus Gorpe on BBC’s Dragon’s Den

The last entrepreneur to pitch in the show was the founder of the Raw Chocolate Company, an interesting character called Linus Gorpe (quote: “I love life. Life is the dance for me. I play a lot. I play in the woods. I eat a lot of healthy food. I love clean living. I love women, oh I love women.” Ahem).

He was promoting his ‘raw’ chocolate products. The Dragons asked what he meant by raw: he said something about heating up apples for two hours in an oven. I don’t think anyone was much the wiser. But I’m not going to pick holes in the ideas behind raw food diets (Science Based Medicine wrote a great article on that topic a little while back, I urge you to check it out).

No, I was more bothered by this little exchange:

Deborah Meaden: “So, the sugar content when comparing it to other chocolate. Same?”
Linus: “No. I use coconut palm sugar, which is um, not refined white sugar. It’s the sugar that’s been made from-”
DM (interrupting): “That’s interesting, so it’s unrefined?”
LG: “It’s unrefined. It’s boiled. So it doesn’t raise your blood sugar levels.”

Peter Jones chimed in at this point on something else entirely, leaving me shouting pointlessly at the telly. Not least because hadn’t he just said heating food was basically bad? And now he’s talking about boiling?!

Saccharose2

Sucrose

But that’s the least of my problems with this. Firstly, what is the difference between refined sugar and unrefined sugar? As the name suggests it’s really just a question of processing. Somehow the word ‘refined’ seems to have become irrevocably linked in people’s minds with ‘horribly unhealthy’ whereas ‘raw sugar’ somehow sounds much better. In reality, in the case of cane sugar (for the sake of comparing like with like), all the ‘refined’ bit means is that any non-sugar ingredients, which mainly provide flavour and colour, have been removed and the water has been rapidly evaporated from the sugar solution to produce fine, white crystals of pure sucrose.

Raw sugar, before the refining process, is still mostly sucrose. And truly raw sugar syrup, i.e. completely unprocessed, doesn’t often work very well as an ingredient. So when people talk about ‘unrefined’ sugar, what they usually mean is ‘a bit less refined’ sugar.

Ah, I hear you say, but he didn’t say cane sugar. He said coconut palm sugar. Yes, he did. So what’s that, then?

Coconut palm sugar, or just coconut sugar, is sugar produced from the sap of the cut flower buds of the coconut palm plant. It is usually less refined than cane sugar: essentially the syrup is harvested from the plant and then simply heated to remove the excess water. It’s a pretty simple process.

But does that make it any healthier? What does it actually contain?

179px-Beta-D-Fructofuranose

Fructose

157px-Alpha-D-Glucopyranose

Glucose

Well, coconut palm sugar is, guess what, about 80% sucrose. The remaining 20% is made up of a mixture of glucose and fructose. Both of which are also sugars. In fact, if you have a look at the images I’ve inserted here, they’re very similar molecules. Chemists describe them as isomers; they have the same number and types of atoms, just arranged slightly differently. If you’ve really been paying attention, you might notice that sucrose is, in fact, just a glucose molecule joined up with a fructose molecule.

When you eat sucrose, your body breaks it down into glucose and fructose. So practically, consuming any of these will have basically the same result, which is to raise your blood sugar. Pure glucose causes the biggest spike, because your body doesn’t have to do anything very much at all in the way of digestion, but just to make this absolutely clear: table sugar is not glucose. It is sucrose.

How much your blood sugar rises when you eat mostly depends on what else is in the food. A whole piece of fruit, for example, also contains a lot of fibre. That fibre slows down digestion, which means the sugar (there’s a lot of fructose in fruit) is absorbed more slowly than if you, say, swallowed a teaspoon of the same sugar on its own.

Coconut palm sugar

Coconut palm sugar

In short, refined sugar raises your blood sugar levels. But so does unrefined/raw/partially-refined/whatever-we’re-calling-it-today sugar. It was frankly flat-out incorrect of Linus to state that coconut palm sugar doesn’t raise blood sugar levels, because it does.

There is a bit of debate around how much it raises blood sugar levels. One oft-quoted study (consisting of a grand total of ten participants, and carried out by the Philippine Food and Nutrition Research Institute – incidentally the Philippines is one of the world’s largest producers of coconut palm sugar) quoted a glycemic index (GI) for coconut sugar of about 35, which would compare quite favourably with table sugar (about 58) and pure glucose (100, by definition).

On the other hand, hunt around a bit and another source pops up quoting a GI of 54 for coconut sugar. Which is… about the same as table sugar (and given the chemical make-up of coconut sugar, it’s hard to think of a good reason why they should be very different).

The truth is, there isn’t any such thing as ‘healthy’ sugar, certainly not in the way we talk about ‘healthy fats‘. If you’re going to eat products made with sugar, any sugar, you have to accept that while they may be jolly tasty (that ought to be a give-away, really) they’re treats, and should probably still be enjoyed only in moderation.

I’m sure that the Raw Chocolate Company’s products are delicious, and I’m not particularly anti-sugar. But let’s not be misleading. If someone genuinely cares, for whatever reason, about the sugar in their food, it’s important they get accurate information. Saying things like “it doesn’t raise your blood sugar” is, well, frankly a bit naughty.

The dragons know their stuff, and Deborah Meaden (who eventually invested) is a very smart lady. There’s no way she’ll allow any inaccurate, or even questionable, claims to persist in the long term, so I daresay this is the last time we’ll hear the blood sugar thing in relation to these products. But still, if he’d quoted dubious sales figures they’d have been all over it. Grrr.

About this time last year I wrote a post about a company claiming that their agave-sweetened products are ‘sugar-free’. They’re still out there. They still say their products are sugar-free (although they are making some that are sweetened with the sweetener xylitol now, which they’ve bizarrely chosen to label ‘no added sugar’). Their products still do, in fact, contain sugar. Sigh.

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Please don’t eat apricot kernels

Capture

Apricot kernels do not cure cancer.

I’ll admit, I’m no huge fan of ‘alternative medicine’, particularly the ones which have been thoroughly tested and shown over and over again to be entirely ineffective (yes homoeopathy, I’m looking at you).

At best these treatments don’t work, and at worst they delay or even stop people getting the effective treatment they need. In fact, there’s an even worse possibility: they stop people from people from giving their children the treatments they need.

Ok, if you’re old enough to make decisions for yourself, and you’ve tried conventional medicine and it hasn’t worked terribly well for your particular problem, and you’ve found that, say, acupuncture somehow does make your chronic back pain a bit better, even if it is just placebo effect, then hey, it’s your money (just please don’t recommend it to anyone else who hasn’t checked out all their other options first, ok?) Also, please, please read this fantastic article which explains clearly what cancer is and what, crucially, it isn’t.

But there has surely has to be a special corner of hell reserved for people who peddle so called ‘cancer-cures’.

Medicine has moved on a lot in the last few decades. Advanced screening techniques and treatments mean that many cancers are no longer the death sentence they once were. 50% of people (in England and Wales) now survive cancer for ten years or more, which is double the figure 40 years ago. But it’s easy for a well person to say ‘cancer treatments’. They are not always quite so easy to get through. Cancer treatments – namely surgery, radiotherapy and chemotherapy – can be brutal and frequently come with a raft of unpleasant side-effects, particularly chemotherapy.

There are some people who decide that the cure is worse than the disease and personally, I think that’s their choice to make. They should have the right to make that choice, so long as it’s well-informed.

So long as it’s well-informed.

But there are people out there who are making money from desperate cancer sufferers. They sell them ineffective treatments, discourage them (directly or indirectly) from seeking or accepting the treatment they really need, and sometimes even encourage those people to use toxic substances that are likely to actually cause even more harm.

People like Roger Shelley, owner and director of The Vitamin Service Ltd. Who has just been given a six-month suspended prison sentence and his company fined £10,000 for selling potentially toxic ‘vitamins’ he claimed could cure and prevent cancer.

512px-Amygdalin_structure.svg

Amygdalin. It’s not a vitamin.

In particular, he was selling apricot kernels, which he claimed contained a ‘vitamin’ called B17. There is no such vitamin. The chemical in question is something called amygdalin (sometimes also referred to as laetrile, although they are not quite the same thing). See the picture of it? See that CN group down at the bottom? That’s a nitrile group. Potassium cyanide, the poison so beloved of crime writers, has the formula KCN, which is a compound made up of K+ and CN ions. It’s the cyanide ions, CN, that do the damage, by interfering catastrophically with the way the body uses oxygen. Now, nitriles (like amygdalin) don’t usually give up their cyanide ions easily and so aren’t, generally, anywhere near as toxic as compounds like potassium cyanide.

Unfortunately one of the enzymes in your small intestine helps to speed up the breakdown of amygdalin. Eating apricot kernels can cause severe toxicity and death due to cyanide poisoning. Yes, severe toxicity and death. Eating apricot kernels can kill you.

Before I cause mass panic I should probably point out that if you accidentally swallow one on a summer picnic, do not fear. It takes more than one to do any damage. The Food Standards Agency says it’s safe to eat one apricot kernel a day (they’re not saying you should, mind you).

The Vitamin Service was recommending that adults take 35 kernels every day. That IS enough to do damage. In fact, it’s above the dose that the FSA highlights as causing severe symptoms. In this statement, they site a case (point 15) of a woman who ate 30 apricot kernels and was later found comatose.

Worse, The Vitamin Service were also recommending that children take 10 kernels a day, “to ward off cancer”. For children, who have a smaller body mass than adults, even this smaller dose could be extremely dangerous.

Patients following The Vitamin Service’s regime reported symptoms of dizziness and cogitative problems. Classic symptoms of cyanide poisoning. When they reported these symptoms they were advised to reduce the amount for a few days before increasing it again, because the symptoms were due to ‘toxins’. Indeed they were, a toxic substance in the very products The Vitamin Service were selling.

To add insult to injury, they were charging in the region of £600 for these kernels along with a raft of other supplements they were recommending.

Shelly admitted to misleading customers and failing to warn them of the risks of B17. He has been given a six month suspended prison sentence, and his company is no longer selling apricot kernels as a cancer treatment. Which you’d think would be a good thing. Problem solved, no?

Just Google “B17 cancer” or “apricot kernels”. There are dozens of sites out there promoting it as a cancer treatment, and many still selling products. I won’t link to them here, I don’t want to give them the traffic. But it’s frightening. Please don’t believe these people. Please listen to your doctors, the real ones, the ones who have studied for years to learn everything they can about medicines and illnesses, and who have sworn an oath to “do no harm”.

There isn’t an easy, painless, magical cure for the cancer that the pharmaceutical industry is hiding from us for some reason. We all wish there was, but there isn’t. Cancer is horrible, but a lot of the time these days it’s beatable with the right treatments. And for those, you need a qualified doctor.

This story was covered in detail on The One Show on BBC One, on Monday 4th February 2015. You can watch the clip here: start at about 4:30 minutes.

There is also an excellent, very easy to follow, summary of the use of laetrile on the charity Cancer Research UK’s website. Read it here.

Finally, once again, if you’re in the unfortunate position of having been diagnosed with cancer, please, please read this excellent article. It really does help to understand the importance of targeted treatment.

Update 8th June 2015

When I wrote this post I focused on the eating of actual apricot kernels, and Roger Shelley’s conviction for selling them. It is worth pointing out that although apricot kernels definitely contain amygdalin, it’s impossible to be certain exactly how much any one kernel contains. This is always a risk with any natural product like this.

This means there is a big, huge, difference between eating apricot kernels – even a known number of them – and being exposed to a small amount of amygdalin in a controlled manner, say as part of a cancer treatment trial. In the first situation you have no idea how much of the chemical you’re being exposed to, and no one is monitoring you to check for ill effects (which you might, or might not, be aware of). It is true that otherwise toxic compounds are utilised in chemotherapy. Arsenic trioxide is used to treat a particular kind of leukaemia for example, but this doesn’t mean swallowing a teaspoon of it every day ‘just in case’ would be in any way sensible or safe.

In 2010 there was a Cochrane review of all the work previously done on amygdalin and laetrile. It reported that there was no clinical data to support the use of these substances to treat cancer, that the risk benefit of using these substances was unanimously negative (the risk of severe poisoning far outweighed any possible benefit), and recommended that no further clinical research into laetrile or amygdalin be conducted on ethical grounds.

However, since I wrote this post I have been made aware that some research is still ongoing. Well, science is about finding answers after all. For example, both of the following papers have been published since the Cochrane review:

Notice that these papers are about the specific chemical amygdalin, rather than apricot kernels. Note also that the second paper contains the words in vitro, which means outside of living organisms. In a test tube in a lab basically. This might be an interesting starting point, but it doesn’t necessarily mean that the same effect can be reproduced in living organisms which have inconvenient things like a digestive system to work around. Also, bear in mind that effective cancer treatments are highly targeted. Tossing unknown amounts of a substance into the general vicinity of a tumour and hoping it’ll have the effect you want is like throwing a bucket of paint at a piece of fine china and expecting to see pretty decorations appear.

Digestion is a particularly thorny problem with this substance: in the first paper I mentioned above (which is a review of the work done to date, rather than new research) the authors specifically point out that amygdalin is a lot more toxic when it’s taken orally than when it’s given intravenously (injected). The reason is that, as I mentioned in my original post, it’s broken down by enzymes in your small intestine. You’re going to have a hard time injecting apricot kernels; you pretty much have to eat them. Which is risky.

Also, while the authors do provide a lot of examples of the therapeutic benefits of amygdalin, they also point out that the (apparent) “antitumor mechanism of amygdalin is not completely clear”, that “clinical trials and large retrospective studies showed that [it] had no stable antitumor effect” and that adverse reactions have been reported, particularly following large doses.

So, while this compound might be a subject for further research, I stand by my original point. Don’t eat apricot kernels.

Further update, 20th August 2015

I’ve recently been made aware of a someone called Dr Philip Binzel and, what appears to be, a rather famous book called “Alive and Well“. In this book, Dr Binzel describes his treatment of cancer patients using dietary changes and supplements, including laetrile. I can find remarkably little information about Dr Binzel and his credentials beyond what’s described in this book. However, it is a matter of public record that he died on June 6, 2003. So take any source discussing his work in the present tense with a large pinch of salt.

Another recent post on this blog which may be of interest addresses this common complaint, “no one wants to research that; they can’t make any money from it!

Follow The Chronicle Flask on Facebook for regular updates and other interesting tidbits.

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Why is chemistry the forgotten science?

I recently had the privilege of talking to radio DJ and author Simon Mayo and he asked me what I thought of his book, Itch.  I said I loved it, and I really do.  (I have yet to read the sequel, Itch Rocks – released at the end of February – but it’s definitely on my list.)  I like Itch for many reasons.  I liked it because the lead character is a teenage boy who’s interested in science and actually finds arty subjects rather difficult, and yet is not a nerdy stereotype.  I like it because there was lots of action and an interesting story, coupled with just the right amount of research.  I liked it because the main female character is strong-willed, principled and absolutely doesn’t get involved in any sort of love triangle (this is not, to paraphrase my favourite film, ‘a kissing book’).  And most of all, I like it because it’s science fiction about chemistry.chemistry

As a chemist, it’s long seemed to me that, when it comes to the media and fiction, it’s the forgotten science. I can think of any number of famous science fiction works that hinge around physics and astronomy.  I can think of things based on biology.  I can even recall one or two that have both, for example Christian Cantrell’s Containment, a novel about a brilliant young scientist living on Venus and working on artificial photosynthesis.  But when it comes to chemistry I’m struggling.  Poisoning turns up in quite a few murder mysteries of course, as does forensics.  I suppose you could argue that some of the medical thrillers with plots that hinge around drugs might count.   Nanotechnology, as in Prey by Michael Crichton, is often thought of as a chemical field in the real world (TM), but thrillers on the subject tend to be less about matter on the atomic scale and more about improbably aggressive tiny robots.

It’s not just fiction.  In recent years there has been a noticeable increase in the amount of science programming, particularly on the BBC.  This is fabulous, but the large majority has been focused on physics and biology.  Radio 4’s The Infinite Monkey Cage often takes great glee in ignoring, and even ridiculing, chemical disciplines (I still listen to it mind you, in the manner of someone poking at a sore tooth).  The current run of BBC’s Horizon has exactly one episode (The Truth about Taste) that might be considered to have a chemistry focus.  At the end of last year Dara O Briain’s Science Club managed a whole series of six episodes without a single one on a chemical topic.  And so on and so on.  At least the most recent Royal Institution Christmas Lectures redressed the balance a bit, even if they were tucked away on BBC Four.  And as I posted recently, the quiz show Pointless seems to be quite fond of chemistry as a topic, so that’s something.

But why the general lack of chemistry?  Especially when you consider that the A-level is not only desirable but an essential requirement for so many degrees, including medicine, veterinary science, dentistry and pharmacy.  Whereas physics and, perhaps more surprisingly, biology aren’t. Since it’s so important you’d imagine there would be a bit more enthusiasm for the subject.

Is it linked to the background of the presenters?  Dara O Briain, in a previous life, studied mathematics and theoretical physics.  Professor Brian Cox, presenter of the Infinite Monkey Cage, is of course a physicist.  The only regular presenter I can think of with anything resembling a chemistry degree (actually biochemistry) is Liz Bonnin of Bang Goes the Theory.  But surely it isn’t impossible to find a chemist capable of presenting?  Peter Wothers did a cracking job with the Royal Institution lectures for starters.  And surely, surely, there’s room for the fabulously eccentric-looking Martyn Poliakoff somewhere?  (Please go and look at The Periodic Table of Videos if you have five minutes – it’s brilliant.)

But I’m not sure that’s the problem.  I imagine presenters largely talk about what they’re told to talk about.  No, I fear it might be simply the fact that chemistry is a bit, well, hard.

Early in my teaching career an exasperated A-level student complained, “miss, I thought chemistry was all setting fire to things and explosions and stuff, but it’s mostly just numbers and symbols”.  I’m afraid there’s some truth to this, particularly by the time we get to A-level chemistry, although I do like to set fire to things wherever possible (in a controlled manner of course – I’m not an arsonist, I swear).

I often joke with students that chemists use equations because we’re lazy.  For example, take this very simple experiment that you probably do every day if you have a gas cooker – it’s what happens when you set fire to methane:

CH4 + 2O2 –> CO2 + 2H2O

Now let’s write that in words: One molecule of methane, which contains one carbon atom bonded to four hydrogen atoms, reacts with exactly two molecules of diatomic oxygen irreversibly to produce exactly one molecule of carbon dioxide, which contains one atom of carbon bonded to two oxygen atoms, and two molecules of water, which contains two atoms of hydrogen bonded to an oxygen atom. 

Phew.  You can see why chemists prefer the equation.  Imagine if we had to write something like that every time we wanted to describe a reaction?  We’d never get anywhere.  Plus, once you understand them, the equations allow you to see similarities between different reactions that could be easily missed otherwise.  The symbols are essential.  But they’re also a bit, well, impenetrable.  A TV show with lots of chemical symbols would be as impossible to understand as one presented in French for many, and rather more difficult to subtitle.

So yes, it can look a bit scary.  But it’s not impossible.  After all you need advanced mathematics to understand physics in depth, but plenty of physics programmes explain their subject matter without even hinting at the dreaded doublet of differentiation and integration.  A good chemist can make the subject accessible with a bit of creativity.

It’s not as if there’s not lots of interesting material (pun entirely intended).  Chemistry is the science behind explosives, cooking, medicines, bubbles, pigments and poisons.  It has a fascinating history, populated with characters such as Fritz Haber, the father of chemical warfare who also solved the problem of global food security, Glenn Seaborg who discovered ten (ten!) of those elements that loiter at the bottom of the periodic table, Henry Cavendish – discoverer of hydrogen and famously so shy he was unable to talk to women, Antoine Lavoisier, tax collector, traitor and the person who named both oxygen and hydrogen and let’s not forget Carl Wilhelm Scheele, discoverer of some of the most dangerous substances known to man.  There are endless stories that could be told, from the legal case of the Carbolic Smoke Ball to Kekule’s dreams of snakes eating their own tails, to bizarre medical practices such as antimony pills and the mystery of the Bradford Sweets poisoning.

If Simon Mayo can write a series of highly successful novels featuring chemistry aimed at young adults, it must surely be possible to make a few more shows on the topic.  So writers, editors and producters I beseech you not to be scared of chemistry.  Find yourself someone with a bit of knowledge in the area and get on with it.  For whatever chemistry is, it’s far from boring.

Do you know of any chemistry science fiction I’ve missed?  Have you got any favourite chemical stories that you think should be on telly?  Please tell me about them!