Chemically identical compounds - Syntetic vs natural

[Jabberwocky]

Hi all.

I just had a discussion with this "everything natural is great and everything syntetic is crap" kind of guy which seemed to take a lot of bullshit for facts.
First of all, he believed that it was IMPOSSIBLE to overdose on vitamins/minerals if they were from food or in the form of natural supplements. Why? He couldnt answer that.
Secondly, he insisted that a natural derived, lets say vitamin c, would act different once consumed from syntetic vitamin C, even if they were the exact same molecyle. Like syntetic ascorbic acid vs natural ascorbic acid - which doesnt make any god damn sense to me.
He went on to give an example of beta caroten, were it has been proven that the syntetic form raises the risks of developing lung cancer in smokers where the natural form has been proven to lower it - 1 minute of googleling showed me that these 2 molecyles are not chemically identical and so once again he made a jackass of him self.

Anyways, my question is this.
Have there ever been ANY kind of science based study that showed that 2 identical chemicals (same vitamin/mineral/whatever on the exact same form) which have acted differently inside the body once consumed? Given that the 2 are taken under the same circumstances. ´Cause I sure cant find it.

 

[flyhighk]

I will use ascorbic acid as an example. (I don't think ascorbic acid is the form of vit C naturally present in plants but let's assume it is)
Ascorbic acid is gonna behave the same way in the human body, no matter where it's coming from. The only possible difference between the natural and synthetic molecule would be isotopes. The natural molecule may have a different isotope of carbon than the synthetic molecule. But that wouldn't change its effects in the human body I think.
I'm moving this to NPD, as this is a more advanced question.

 

[Jabberwocky]

Im pretty sure that the natural occuring vitamin C is indeed L-Ascorbic acid.
Thats what I thought too. But a chemical is not worthy of the term "chemically identical" if one of the compounds have more or less of anything is it?

 

[flyhighk]

I forgot to mention isomers, different isomers may have different effects. Like amphetamine.
What do you mean by "more or less of anything" ? More or less of what?

 

[Jabberwocky]

Isomers, stereotopes and stuff like that? As you can hear, I dont understand these things at all, but Im trying to learn.
In the discussion I mentioned in my opening post, I found out that the difference between syntetic beta caroten and the natural occuring one was the following

"Most, but not all, beta-carotene in supplements is synthetic, consisting of only one molecule called all trans beta-carotene. Natural beta-carotene found in food is made of two molecules—all trans beta-carotene plus 9-cis beta-carotene. "

Both are beta caroten but NOT chemically identical, right?

 

[flyhighk]

All trans and 9 cis are isomers.
Yes both are beta carotene, they have the same molecular formula, but the atoms are arranged differently.
Both are made of 40 carbons and 56 hydrogens but the placement of these atoms in the first isomer differs from that of the atoms in the second isomer.

 

[Wicked702]

2 year Chem degree only, so I know *some* of what I'm talking about. Just qualifying my answer a bit because I'm not a true expert.

Take table salt, NaCl. If I synthesize some in the lab, versus extracting some from sea water, assuming they are both equal in purity they will behave the EXACT SAME WAY in the body. The same will go for any substance. A natural vitamin and a synthetic vitamin, assuming they are ACTUALLY the same composition (rotation, mirror image, atom arrangement, etc.) will again behave the EXACT SAME WAY in the body. So no, your friend is wrong. Here is where it gets tricky. Biochemistry isn't something done in isolation. An extract of a natural compound (assuming it's taken as is and not purified) could contain other compounds/molecules. Those other substances could assist the main compound in some way when used by an organic system. A synthetic substance won't have those other compounds. That CAN change the overall effect.

Here's an example. I like strawberries. So I eat a fresh strawberry and then later I eat a piece of strawberry candy. They taste very similar, but not the same. Why? Well, the candy contains only the "artificial strawberry flavor," which is actually just one specific molecule from a strawberry. In this case, it would be an ester. Esters are molecules that makes things taste sweet. But the real strawberry contains all sorts of other molecules. Fibers, salts, and of course the ester. So you get a different overall effect because of the interference/addition of these other compounds. Make sense? So there's nothing wrong with the artificial strawberry flavor, it's just missing it's natural buddies. But 1:1, the pure ester in a strawberry is the same whether it comes off the vine or out of a beaker.

I should also mention that I'm a Purchasing Agent and I work for a chemical company that supplies 50,000 substances to labs, universities, manufacturers, etc. So I deal with this issue on a daily basis. Sometimes it's cheaper to industrially produce a substance and sometimes it's easier to get it from nature. Better tell your friend, when he takes a vitamin pill it's quite likely that many of the compounds inside it where synthesized in a lab. They're held to a very high quality standard to be ok for human consumption of course, but it doesn't always mean they were squeezed from a plant.

 

[.:Holy::Toast:.]

The molecule is identical, however the form it is present in may not be, whether it be a hcl salt, a citrate salt, an acetate salt, or what have you many molecules can be present in different forms and have different bioavailabilities in their different salt forms.
As well vitamins from natural food sources can have better absorption because the food may also contain other molecules or substances which can enhance absorption of said vitamin or mineral.
Take iron for example, it is often better absorbed from red meat because it is heme iron opposed to non-heme iron from plant sources.
Also ferrous sulfate, the common iron supplement given to iron deficient people is best absorbed when taken along with a vitamin C tablet to increase the acidity in your stomach which promotes absorption.
However from a pharmacodynamic standpoint the same chemical will have the same effects from plant or animal sources.
In terms of psychoactives you can use synthetic mescaline hcl versus extracted mescaline.
As long the extraction yields pure mescaline hcl it will be identical to synthetically made mescaline hcl in both terms of effects and metabolism.

 

[Black]

First of all, he believed that it was IMPOSSIBLE to overdose on vitamins/minerals if they were from food or in the form of natural supplements. Why? He couldnt answer that.

then i suggest he should eat some polar bear liver. it's natural after all and contains a lot of vitamin a. in fact enough vitamin a to kill a human.

but there is some kind of truth to his views (even if he's totally wrong). eating fruits or vegetables is much healthier than taking vitamin pills.
there's a famous study wherein they gave vitamin a to workers who had inhaled lots of asbestos. the reasoning behind this is that people with a diet high in vitamin a had lower incidence of lung cancer. but this study had to be ended prematurely because the patients in the vitamin a group had a much higher incidence of lung cancer than those in the placebo group. this of course is due to the other compounds present in the vegetables/fruits also play their part in the beneficial effects. of course if the vitamin a is extracted and purified, it has exactly the same harmful effects as synthetic vitiman a. the point is that complex mixtures of compounds often have different effects from isolated ones.

shortly after that, it was discovered that vitamin e (tocopherol) can help with free radicals and protect from cancer. soon afterwards lots of "healthy" supplements containing tocopherol appeared. then again, not long ago a study showed that tocopherol as a pure compound rather increases than decreases the risk...


but really, any identical compounds (that is identical including stereochemistry) will of course act completely identical.

 

[sekio]

Have there ever been ANY kind of science based study that showed that 2 identical chemicals (same vitamin/mineral/whatever on the exact same form) which have acted differently inside the body once consumed? Given that the 2 are taken under the same circumstances. ´Cause I sure cant find it.

Nope.

As others have pointed out, though - when we think of nutrients in nature, they are almost always combined with hundreds of other compounds. Synthetic vitamin C, for instance, is different from eating rose hips, because rosehips contain other things like flavones, polyphenols, etc. - even though the vitamin C molecules in plants are mostly indistinguishable from those made in a lab*.

* The only reason I say "mostly" is because of this thing called isotopic profiling. You may have heard of isotopes, which are atoms that are the same functionally but have different mass. It turns out that plants prefer to incorporate a certain ratio of isotopes into their metabolic products. (There is a certain ¹³C/¹²C ratio for the different carbon fixation pathways, and living organisms also have ¹⁴C, which is the isotope used to figure out carbon dates - petroleum does not.)

This is not relevant to the functionality of the compounds though... the isotopes don't change the activity of the compound in any measurable way (unless you start making totally synthetic compounds w/ large amount of labeling)

 

[Jabberwocky]

Thanks for all of your answers guys, great information!

Its funny that you should mention liver Black, ´cause I used the exact same reference in order to put things into perspective for this dude, who btw, is not my friend but just some random "all knowing, all natural, fuck syntetics, fond of pseudoscience asshole" who I got into a little debate with online (not on bluelight). He had some crazy ideas which he proclaimed to be the one and only truth, but Im not going to completely reject anything untill I have enough knowledge on the subject to do so, hence, this thread. But yeah, he also believed that it would be impossible to get a vitamin A overdose from eating liver.

 

[red22]

Show your friend this:


As we took leave of María Sabina and her clan at the crack of dawn, the curandera said that the pills had the same power as the mushrooms, that there was no difference. This was a confirmation from the most competent authority, that the synthetic psilocybin is identical with the natural product. As a parting gift I let María Sabina have a vial of psilocybin pills. She radiantly explained to our interpreter Herlinda that she could now give consultations even in the season when no mushrooms grow.

Albert Hofmann, LSD: My Problem Child