Vitamin E

12 Jan 2004 23:46:22 -0800 in article
<[email hidden]> [email hidden]

(francispoon) said:

Can vitamin E be used to replace aspirin in doing what aspirin is meant to do for the
blood vessels?

They work by different mechanism, so it's probably advisable to take both. Natural vitamin E is
better than synthetic one. I would consider a product which contains also gamma-tocopherol, other
tocopherols and tocotrienols in addition to the standard alpha-tocopherol.

--
Matti Narkia

On Tue, 13 Jan 2004 10:03:04 +0200, Matti Narkia <[email hidden]>

Quoted message said:

Natural vitamin E is better than synthetic one.

If they are the exact same biochemical formula, why?

antwrp.gsfc.nasa.govap010301.htmlOpen ↗ Lift well, Eat less, Walk fast, Live long.

Tue, 13 Jan 2004 05:59:46 -0500 in article
<[email hidden]> SunNoM_un <[email hidden]>

Quoted message said:

Matti Narkia said:

Natural vitamin E is better than synthetic one.

If they are the exact same biochemical formula, why?

They are not, the natural one is d-alpha-tocopherol, while the synthetic one is dl-alpha-tocopherol.
Google away to find the difference.

--
Matti Narkia

Matti Narkia said:

Tue, 13 Jan 2004 05:59:46 -0500 in article <[email hidden]> SunNoM_un

Quoted message said:

Matti Narkia said:

Natural vitamin E is better than synthetic one.

If they are the exact same biochemical formula, why?

They are not, the natural one is d-alpha-tocopherol, while the synthetic one is dl-alpha-
tocopherol. Google away to find the difference.

The synthetic one is a 50-50 *mixture* of d-alpha and l-alpha. You can take twice as much of the
synthetic for the same amount of "natural."

Humbly,

Andrew

--
Dr. Andrew B. Chung, MD/PhD
Board-Certified Cardiologist
heartmdphd.comheartmdphd.comOpen ↗

On Tue, 13 Jan 2004 14:25:46 +0200, Matti Narkia <[email hidden]>

Quoted message said:

Quoted message said:

If they are the exact same biochemical formula, why?

They are not, the natural one is d-alpha-tocopherol, while the synthetic one is dl-alpha-
tocopherol. Google away to find the difference.

First, that is incorrect and second, I said "if" they are exactly the same.

antwrp.gsfc.nasa.govap010301.htmlOpen ↗ Lift well, Eat less, Walk fast, Live long.

Matti Narkia said:

Tue, 13 Jan 2004 05:59:46 -0500 in article <[email hidden]> SunNoM_un

Quoted message said:

Matti Narkia said:

Natural vitamin E is better than synthetic one.

If they are the exact same biochemical formula, why?

They are not, the natural one is d-alpha-tocopherol, while the synthetic one is dl-alpha-
tocopherol. Google away to find the difference.

Come on, Matti. M_ellowyellow knew it all along. He was just testing you to see if *you* knew.

Poor lightweight M_onkfish. He's very actively involved in health and body issues, you know. Knows
all about this stuff. Says he's a professional in the field with "patients." Brilliant researcher
who can find answers in a second. Talks to the people doing the research in person, doncha know...

Pastorio

Tue, 13 Jan 2004 11:52:51 -0500 in article <[email hidden]>

Dr. Andrew B. Chung said:

Matti Narkia said:

Tue, 13 Jan 2004 05:59:46 -0500 in article <[email hidden]> SunNoM_un

Quoted message said:

On Tue, 13 Jan 2004 10:03:04 +0200, Matti Narkia <[email hidden]> wrote:

>Natural vitamin E is better than synthetic one.

If they are the exact same biochemical formula, why?

They are not, the natural one is d-alpha-tocopherol, while the synthetic one is dl-alpha-
tocopherol. Google away to find the difference.

The synthetic one is a 50-50 *mixture* of d-alpha and l-alpha. You can take twice as much of the
synthetic for the same amount of "natural."

Yes, but why would one do that? L-alpha-tocopherol is a xenobiotic substance, which carries no
benefit, but which body has to get rid of.

Moreover, nowadays there are available tocopherol mixtures containing alpha, gamma, and delta
tocopeherol, sometimes also tocotrienols. Mixed tocopherols for example have stronger inhibitory
effect on lipid peroxidation than alpha-tocopherol alone:

Liu M, Wallin R, Wallmon A, Saldeen T. Mixed tocopherols have a stronger inhibitory effect on lipid
peroxidation than alpha-tocopherol alone. J Cardiovasc Pharmacol. 2002 May;39(5):714-21. <URL:http:-
//www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11973415&dopt=Abstract>

--
Matti Narkia

Tue, 13 Jan 2004 12:33:21 -0500 in article
<[email hidden]> SunNoM_un <[email hidden]>

Quoted message said:

Matti Narkia said:

Quoted message said:

If they are the exact same biochemical formula, why?

They are not, the natural one is d-alpha-tocopherol, while the synthetic one is dl-alpha-
tocopherol. Google away to find the difference.

First, that is incorrect and second, I said "if" they are exactly the same.

Would you mind enlightening us, what exactly, in your opinion, is incorrect in my comment?

--
Matti Narkia

"Dr. Andrew B. Chung, MD/PhD" schrieb:

Quoted message said:

Matti Narkia said:

Tue, 13 Jan 2004 05:59:46 -0500 in article <[email hidden]>

SunNoM_un said:

On Tue, 13 Jan 2004 10:03:04 +0200, Matti Narkia <[email hidden]> wrote:

>Natural vitamin E is better than synthetic one.

If they are the exact same biochemical formula, why?

They are not, the natural one is d-alpha-tocopherol, while the synthetic one is dl-alpha-
tocopherol. Google away to find the difference.

The synthetic one is a 50-50 *mixture* of d-alpha and l-alpha. You can take twice as much of the
synthetic for the same amount of "natural."

Actually, you can't.

First, alpha-tocopherol has *3* chiral centers which means that there are *8* stereoisomers.

That why nowadays natural alpha-tocopherol is called RRR-alpha-tocopherol whereas the synthetic one
is called all rac-alpha-tocopherol.

So you would have to take eight times as much of the synthetic for the same amount of natural.

But there is a second problem. The level of vitamin E in the blood or in cholesterol-particles or
whereever it is needed is not proportional to the amount ingested. If you take eight times as much
vitamin E the levels in your body won't be eight times as high:

"In addition, the capacity of the plasma to increase -tocopherol concentrations is limited. In
subjects with a normal alpha-tocopherol concentration of 25 µmol/L, the concentration cannot be
increased > 2–3 fold, irrespective of the amount or duration of supplementation (10–13). "

" Synthetic all rac--tocopherol increases plasma alpha-tocopherol concentrations only half as much
as RRR-alpha-tocopherol does (15,30,93). Furthermore, the degradation of synthetic all rac-alpha-
tocopherol to alpha-CEHC is 3–4 times that of RRR-alpha-tocopherol (30). "

(Both cites from:

The European perspective on vitamin E: current knowledge and future research

ajcn.org703Open ↗,

in the original instead of "alpha" the greek letter is used)

So with synthetic vitamin E you get less vitamin E in your blood in the first place and then the
body get's rid of it at a higher rate ...

Does not sound like synthetic vitamin E is any good.

Thorsten

--
"Nothing in biology makes sense, except in the light of evolution"

(Theodosius Dobzhansky)

"Dr. Andrew B. Chung, MD/PhD" <[email hidden]> wrote in message news:<[email hidden]>...

Quoted message said:

Matti Narkia said:

Tue, 13 Jan 2004 05:59:46 -0500 in article <[email hidden]>

SunNoM_un said:

On Tue, 13 Jan 2004 10:03:04 +0200, Matti Narkia <[email hidden]> wrote:

>Natural vitamin E is better than synthetic one.

If they are the exact same biochemical formula, why?

They are not, the natural one is d-alpha-tocopherol, while the synthetic one is dl-alpha-
tocopherol. Google away to find the difference.

The synthetic one is a 50-50 *mixture* of d-alpha and l-alpha. You can take twice as much of the
synthetic for the same amount of "natural."

(1)Could people take aspirin and vitamin E 'AT THE SAME TIME'?
(2)How much aspirin is needed used either separately or in conjunction with Vitamin E?

Thank you in advance,

FP
===================================

Quoted message said:

Humbly,

Andrew

Thorsten Schier said:

"Dr. Andrew B. Chung, MD/PhD" schrieb:

Quoted message said:

Matti Narkia said:

Tue, 13 Jan 2004 05:59:46 -0500 in article <[email hidden]>
SunNoM_un <[email hidden]> wrote:

>On Tue, 13 Jan 2004 10:03:04 +0200, Matti Narkia <[email hidden]> wrote:
>
>>Natural vitamin E is better than synthetic one.
>
>If they are the exact same biochemical formula, why?
>
They are not, the natural one is d-alpha-tocopherol, while the synthetic one is dl-alpha-
tocopherol. Google away to find the difference.

The synthetic one is a 50-50 *mixture* of d-alpha and l-alpha. You can take twice as much of the
synthetic for the same amount of "natural."

Actually, you can't.

First, alpha-tocopherol has *3* chiral centers which means that there are *8* stereoisomers.

That why nowadays natural alpha-tocopherol is called RRR-alpha-tocopherol whereas the synthetic
one is called all rac-alpha-tocopherol.

So you would have to take eight times as much of the synthetic for the same amount of natural.

But there is a second problem. The level of vitamin E in the blood or in cholesterol-particles or
whereever it is needed is not proportional to the amount ingested. If you take eight times as much
vitamin E the levels in your body won't be eight times as high:

"In addition, the capacity of the plasma to increase -tocopherol concentrations is limited. In
subjects with a normal alpha-tocopherol concentration of 25 µmol/L, the concentration cannot be
increased > 2–3 fold, irrespective of the amount or duration of supplementation (10–13). "

" Synthetic all rac--tocopherol increases plasma alpha-tocopherol concentrations only half as much
as RRR-alpha-tocopherol does (15,30,93). Furthermore, the degradation of synthetic all rac-alpha-
tocopherol to alpha-CEHC is 3–4 times that of RRR-alpha-tocopherol (30). "

(Both cites from:

The European perspective on vitamin E: current knowledge and future research

ajcn.org703Open ↗,

in the original instead of "alpha" the greek letter is used)

So with synthetic vitamin E you get less vitamin E in your blood in the first place and then the
body get's rid of it at a higher rate ...

Does not sound like synthetic vitamin E is any good.

Still sounds like you can take more of it to compensate.

Humbly,

Andrew

--
Dr. Andrew B. Chung, MD/PhD
Board-Certified Cardiologist
heartmdphd.comheartmdphd.comOpen ↗

Wed, 14 Jan 2004 00:46:21 +0100 in article <[email hidden]>

Thorsten Schier said:

"Dr. Andrew B. Chung, MD/PhD" schrieb:

Quoted message said:

Matti Narkia said:

They are not, the natural one is d-alpha-tocopherol, while the synthetic one is dl-alpha-
tocopherol. Google away to find the difference.

The synthetic one is a 50-50 *mixture* of d-alpha and l-alpha. You can take twice as much of the
synthetic for the same amount of "natural."

Actually, you can't.

First, alpha-tocopherol has *3* chiral centers which means that there are *8* stereoisomers.

That why nowadays natural alpha-tocopherol is called RRR-alpha-tocopherol whereas the synthetic one
is called all rac-alpha-tocopherol.

So you would have to take eight times as much of the synthetic for the same amount of natural.

But there is a second problem. The level of vitamin E in the blood or in cholesterol-particles or
whereever it is needed is not proportional to the amount ingested. If you take eight times as much
vitamin E the levels in your body won't be eight times as high:

"In addition, the capacity of the plasma to increase -tocopherol concentrations is limited. In
subjects with a normal alpha-tocopherol concentration of 25 µmol/L, the concentration cannot be
increased > 2–3 fold, irrespective of the amount or duration of supplementation (10–13). "

" Synthetic all rac--tocopherol increases plasma alpha-tocopherol concentrations only half as much
as RRR-alpha-tocopherol does (15,30,93). Furthermore, the degradation of synthetic all rac-alpha-
tocopherol to alpha-CEHC is 3–4 times that of RRR-alpha-tocopherol (30). "

Thanks for the info. I vaguely remembered RRR-alpha-tocopherol from some usenet discussions, but I
was too lazy to look it up, and therefore resorted to the older terminology.

Quoted message said:

(Both cites from:

The European perspective on vitamin E: current knowledge and future research

ajcn.org703Open ↗,

in the original instead of "alpha" the greek letter is used)

So with synthetic vitamin E you get less vitamin E in your blood in the first place and then the
body get's rid of it at a higher rate ...

Does not sound like synthetic vitamin E is any good.

I agree. If I remember correctly, some (but perhaps not all) of those vitamin E CHD prevention
trials, which gave negative result, used synthetic vitamin E. One of the authors in your reference
study, Jukka T Salonen, is a Finnish researcher, who is also an author in a Finnish atherosclerosis
prevention study using vitamins E and C:

Salonen RM, Nyyssonen K, Kaikkonen J, Porkkala-Sarataho E, Voutilainen S, Rissanen TH, Tuomainen TP,
Valkonen VP, Ristonmaa U, Lakka HM, Vanharanta M, Salonen JT, Poulsen HE; Antioxidant
Supplementation in Atherosclerosis Prevention Study. Six-year effect of combined vitamin C and E
supplementation on atherosclerotic progression: the Antioxidant Supplementation in Atherosclerosis
Prevention (ASAP) Study. Circulation. 2003 Feb 25;107(7):947-53. <URL:http://www.ncbi.nlm.nih.gov/e-
ntrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12600905&dopt=Abstract>

Salonen JT, Nyyssonen K, Salonen R, Lakka HM, Kaikkonen J, Porkkala-Sarataho E, Voutilainen S, Lakka
TA, Rissanen T, Leskinen L, Tuomainen TP, Valkonen VP, Ristonmaa U, Poulsen HE. Antioxidant
Supplementation in Atherosclerosis Prevention (ASAP) study: a randomized trial of the effect of
vitamins E and C on 3-year progression of carotid atherosclerosis. J Intern Med. 2000 Nov;248(5):377-
86. <URL:http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11123502&do-
pt=Abstract>

--
Matti Narkia

Thorsten Schier said:

So with synthetic vitamin E you get less vitamin E in your blood in the first place and then the
body get's rid of it at a higher rate ...

Does not sound like synthetic vitamin E is any good.

Then why not up the dosage?

antwrp.gsfc.nasa.govap040113.htmlOpen ↗ Lift well, Eat less, Walk fast, Live long.

Wed, 14 Jan 2004 00:46:21 +0100 in article <[email hidden]>

Thorsten Schier said:

First, alpha-tocopherol has *3* chiral centers which means that there are *8* stereoisomers.

That why nowadays natural alpha-tocopherol is called RRR-alpha-tocopherol whereas the synthetic one
is called all rac-alpha-tocopherol.

So you would have to take eight times as much of the synthetic for the same amount of natural.

I think this still may need more digging up. In Linus Pauling Institute's article about vitamin E on
the web page

<URL:http://lpi.oregonstate.edu/infocenter/vitamins/vitaminE/>

there are citations like this:

"... 200 mg of synthetic alpha-tocopherol (equivalent to 100 mg of RRR-alpha-tocopherol) ..."

"... 50 mg of synthetic alpha-tocopherol (equivalent to 25 mg of RRR-alpha-tocopherol) ..."

"... 400 or 800 IU of synthetic alpha-tocopherol (equivalent to 268 or 536 mg of>RRR-alpha-
tocopherol) ..."

"RRR-alpha-tocopherol (natural or d-alpha-tocopherol): IU x 0.67 = mg RRR-alpha-tocopherol.
Example: 100 IU = 67 mg

all-rac-alpha-tocopherol (synthetic or dl-alpha-tocopherol): IU x 0.45 = mg RRR-alpha-
tocopherol. Example: 100 IU = 45 mg "

Admittedly this article does not take account the negative effect of synthetic vitamin D you
mentioned.

There is another vitamin E article on the same site:

The Biological Activity of Vitamin E Maret G. Traber, Ph.D. Associate Professor of Nutrition LPI
Principal Investigator <URL:http://lpi.oregonstate.edu/sp-su98/vitamine.html>

And I just found a study, which probably is the best reference about the topic at hand:

Burton GW, Traber MG, Acuff RV, Walters DN, Kayden H, Hughes L, Ingold KU. Human plasma and tissue
alpha-tocopherol concentrations in response to supplementation with deuterated natural and synthetic
vitamin E. Am J Clin Nutr. 1998 Apr;67(4):669-84. <URL:http://www.ajcn.org/cgi/reprint/67/4/669.pdf>
(full text) <URL:http://www.ajcn.org/cgi/content/abstract/67/4/669> (abstract)

I don't have time to go through the full text now, but post the abstract here:

"We report a comparison of natural and synthetic vitamin E in humans using deuterium labeling to
permit the two forms of vitamin E to be measured independently in plasma and tissues of each
subject. Differences in natural and synthetic vitamin E concentrations were measured directly
under equal dosage conditions using an equimolar mixture of deuterated RRR-alpha-tocopheryl
acetate and all-rac-alpha-tocopheryl acetate. Two groups of five adults took 30 mg of the
mixture as a single dose and as eight consecutive daily doses, respectively. After a 1-mo
interval the schedule was repeated but with a 10-fold higher dose (ie, 300 mg). In each case,
the ratio of plasma d3-RRR-alpha-tocopherol to d6-all-rac- alpha-tocopherol (RRR:rac) increased
from approximately
1.5-1.8 to approximately 2 after dosing ended. In an elective surgery study in which 22 patients
were given 150 mg/d for up to 41 d before surgery, the RRR:rac in tissues was lower than in
plasma and the percentage of deuterated alpha-tocopherol was lower in all tissues except
gallbladder and liver. In a terminally ill patient given 30 mg/d for 361 d, plasma and tissue
(x+/- SD) RRR-rac ratios (and % deuterated alpha-tocopherol) at autopsy were 2.06 (6.3%) and
1.71+/-0.24
(2.9+/-2.2%), respectively. In a second terminally ill patient given 300 mg/d for 615 d, the
corresponding values were 2.11 (68%) and 2.01+/-0.17 (65+/-10%), respectively. The results
indicated that natural vitamin E has roughly twice the availability of synthetic vitamin E.
This 2:1 ratio is significantly higher than the currently accepted RRR:rac of 1.36:1.00. Gamma-
Tocopherol, expressed as a fraction of total unlabeled tocopherols in 15 elective surgery
patients, was 1.4-4.6 (mean: 2.6) times greater in adipose tissue, muscle, skin, and vein
than in plasma, which is a substantially larger fraction than had been recognized
previously."

--
Matti Narkia

Wed, 14 Jan 2004 02:16:51 +0200 in article
<[email hidden]> Matti Narkia <[email hidden]>

Quoted message said:

Wed, 14 Jan 2004 00:46:21 +0100 in article <[email hidden]> Thorsten Schier

Quoted message said:

So with synthetic vitamin E you get less vitamin E in your blood in the first place and then the
body get's rid of it at a higher rate ...

Does not sound like synthetic vitamin E is any good.

I agree. If I remember correctly, some (but perhaps not all) of those vitamin E CHD prevention
trials, which gave negative result, used synthetic vitamin E. One of the authors in your reference
study, Jukka T Salonen, is a Finnish researcher, who is also an author in a Finnish atherosclerosis
prevention study using vitamins E and C:

Salonen RM, Nyyssonen K, Kaikkonen J, Porkkala-Sarataho E, Voutilainen S, Rissanen TH, Tuomainen
TP, Valkonen VP, Ristonmaa U, Lakka HM, Vanharanta M, Salonen JT, Poulsen HE; Antioxidant
Supplementation in Atherosclerosis Prevention Study. Six-year effect of combined vitamin C and E
supplementation on atherosclerotic progression: the Antioxidant Supplementation in Atherosclerosis
Prevention (ASAP) Study. Circulation. 2003 Feb 25;107(7):947-53. <URL:http://www.ncbi.nlm.nih.gov/-
entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12600905&dopt=Abstract>

Salonen JT, Nyyssonen K, Salonen R, Lakka HM, Kaikkonen J, Porkkala-Sarataho E, Voutilainen S,
Lakka TA, Rissanen T, Leskinen L, Tuomainen TP, Valkonen VP, Ristonmaa U, Poulsen HE. Antioxidant
Supplementation in Atherosclerosis Prevention (ASAP) study: a randomized trial of the effect of
vitamins E and C on 3-year progression of carotid atherosclerosis. J Intern Med. 2000 Nov;248(5):377-
86. <URL:http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11123502&d-
opt=Abstract>

Here's another vitamin E study by Jukka T Salonen's team. RRR-alpha-tocopheryl acetate was used.

Porkkala-Sarataho EK, Nyyssonen MK, Kaikkonen JE, Poulsen HE, Hayn EM, Salonen RM, Salonen JT. A
randomized, single-blind, placebo-controlled trial of the effects of 200 mg alpha-tocopherol on the
oxidation resistance of atherogenic lipoproteins. Am J Clin Nutr. 1998 Nov;68(5):1034-41.
<URL:http://www.ajcn.org/cgi/reprint/68/5/1034.pdf>
<URL:http://www.ajcn.org/cgi/content/abstract/68/5/1034> <URL:http://www.ncbi.nlm.nih.gov/entrez/qu-
ery.fcgi?cmd=Retrieve&db=PubMed&list_uids=9808219&dopt=Abstract>

--
Matti Narkia

"Dr. Andrew B. Chung, MD/PhD" schrieb:

Quoted message said:

Thorsten Schier said:

"Dr. Andrew B. Chung, MD/PhD" schrieb:

Quoted message said:

Matti Narkia wrote:

> Tue, 13 Jan 2004 05:59:46 -0500 in article <[email hidden]>
> SunNoM_un <[email hidden]> wrote:
>
> >On Tue, 13 Jan 2004 10:03:04 +0200, Matti Narkia <[email hidden]> wrote:
> >
> >>Natural vitamin E is better than synthetic one.
> >
> >If they are the exact same biochemical formula, why?
> >
> They are not, the natural one is d-alpha-tocopherol, while the synthetic one is dl-alpha-
> tocopherol. Google away to find the difference.
>

The synthetic one is a 50-50 *mixture* of d-alpha and l-alpha. You can take twice as much of
the synthetic for the same amount of "natural."

Actually, you can't.

First, alpha-tocopherol has *3* chiral centers which means that there are *8* stereoisomers.

That why nowadays natural alpha-tocopherol is called RRR-alpha-tocopherol whereas the synthetic
one is called all rac-alpha-tocopherol.

So you would have to take eight times as much of the synthetic for the same amount of natural.

But there is a second problem. The level of vitamin E in the blood or in cholesterol-particles
or whereever it is needed is not proportional to the amount ingested. If you take eight times as
much vitamin E the levels in your body won't be eight times as high:

"In addition, the capacity of the plasma to increase -tocopherol concentrations is limited. In
subjects with a normal alpha-tocopherol concentration of 25 µmol/L, the concentration cannot be
increased > 2–3 fold, irrespective of the amount or duration of supplementation (10–13). "

" Synthetic all rac--tocopherol increases plasma alpha-tocopherol concentrations only half as
much as RRR-alpha-tocopherol does (15,30,93). Furthermore, the degradation of synthetic all rac-alpha-
tocopherol to alpha-CEHC is 3–4 times that of RRR-alpha-tocopherol (30). "

(Both cites from:

The European perspective on vitamin E: current knowledge and future research

ajcn.org703Open ↗,

in the original instead of "alpha" the greek letter is used)

So with synthetic vitamin E you get less vitamin E in your blood in the first place and then the
body get's rid of it at a higher rate ...

Does not sound like synthetic vitamin E is any good.

Still sounds like you can take more of it to compensate.

First, I disagree on that. You might even end up with _less_ natural vitamin E in blood than without
any supplementation at all.

Second, how much vitamin E do you want to take? You would have to take considerably more than one
gram per day to get the desired amount of natural vitamin E (for example 200 mg). You probably
want save any money and you don't know what the wrong stereoisomers or their metabolits might do
in your body.

Third, why would someone want to bet their life just on your guess that it should be possible to
compensate? Why not take the natural one that is known to be safe and where there is evidence that
it is effective?

Thorsten

--
"Nothing in biology makes sense, except in the light of evolution"

(Theodosius Dobzhansky)

Thorsten Schier schrieb:

Quoted message said:

Quoted message said:

Second, how much vitamin E do you want to take? You would have to take considerably more than one
gram per day to get the desired amount of natural vitamin E (for example 200 mg). You probably
want save any money and you don't know what the wrong stereoisomers or their metabolits might do
in your body.

I probably shouldn't write so many posting at this time in the night ...

Of course it must be read:

Quoted message said:

You probably _won't_ save any money and you don't know what the wrong stereoisomers or their
metabolits might do in your body.

--
"Nothing in biology makes sense, except in the light of evolution"

(Theodosius Dobzhansky)

Wed, 14 Jan 2004 03:00:22 +0200 in article
<[email hidden]> Matti Narkia <[email hidden]>

Quoted message said:

Wed, 14 Jan 2004 00:46:21 +0100 in article <[email hidden]> Thorsten Schier

Quoted message said:

First, alpha-tocopherol has *3* chiral centers which means that there are *8* stereoisomers.

That why nowadays natural alpha-tocopherol is called RRR-alpha-tocopherol whereas the synthetic
one is called all rac-alpha-tocopherol.

So you would have to take eight times as much of the synthetic for the same amount of natural.

I think this still may need more digging up. In Linus Pauling Institute's article about vitamin E
on the web page

<URL:http://lpi.oregonstate.edu/infocenter/vitamins/vitaminE/>

there are citations like this:

"... 200 mg of synthetic alpha-tocopherol (equivalent to 100 mg of RRR-alpha-tocopherol) ..."

"... 50 mg of synthetic alpha-tocopherol (equivalent to 25 mg of RRR-alpha-tocopherol) ..."

"... 400 or 800 IU of synthetic alpha-tocopherol (equivalent to 268 or 536 mg of>RRR-alpha-
tocopherol) ..."

"RRR-alpha-tocopherol (natural or d-alpha-tocopherol): IU x 0.67 = mg RRR-alpha-tocopherol.
Example: 100 IU = 67 mg

all-rac-alpha-tocopherol (synthetic or dl-alpha-tocopherol): IU x 0.45 = mg RRR-alpha-
tocopherol. Example: 100 IU = 45 mg "

Admittedly this article does not take account the negative effect of synthetic vitamin D you
mentioned.

There is another vitamin E article on the same site:

The Biological Activity of Vitamin E Maret G. Traber, Ph.D. Associate Professor of Nutrition LPI
Principal Investigator <URL:http://lpi.oregonstate.edu/sp-su98/vitamine.html>

And I just found a study, which probably is the best reference about the topic at hand:

Burton GW, Traber MG, Acuff RV, Walters DN, Kayden H, Hughes L, Ingold KU. Human plasma and tissue
alpha-tocopherol concentrations in response to supplementation with deuterated natural and
synthetic vitamin E. Am J Clin Nutr. 1998 Apr;67(4):669-84.
<URL:http://www.ajcn.org/cgi/reprint/67/4/669.pdf> (full text)
<URL:http://www.ajcn.org/cgi/content/abstract/67/4/669> (abstract)

Check out also Vitamin E postings by Steven B. Harris, MD, at

<URL:http://yarchive.net/med/vitamin_e.html>

This is part of Norman Yarvin's Usenet Archives collection at

<URL:http://yarchive.net/home.html>

I haven't had much time yet to get familiar with the above study and with the postings by Steven B.
Harris, but right now it appears that

a) RRR-alpha-tocopherol (formerly d-alpha-tocopherol) has about twice the bioavailability of all-rac-alpha-
tocopherol (formerly dl-alpha-tocopherol).

b) A given dose all-rac-alpha-tocopherol has only about 75% of the vitamin activity of the equal
dose of RRR-alpha-tocopherol.

c) From a) and b): A given dose of all-rac-alpha-tocopherol has only 0.50 * .75 = 0.375 = 37.5% of
the vitamin activity of an equal dose of RRR-alpha-tocopherol.

d) Because the serum and tissue bioavailability of vitamin E does not depend linearly on the dose,
i.e. the dose has to be more than double to achieve double levels, therefore, based on the
evidence we have found so far we don't yet know exactly how much synthetic vitamin E (all-rac-alpha-
tocopherol) we have to take to get the same vitamin effect than with a given dose of natural
vitamin E (RRR-alpha-tocopherol). What we do know is that _more_ than the double dose is
required. And even with a dose with the "same" vitamin activity than a given dose of natural
vitamin E, the synthetic vitamin E may have some undesired effects, so there is a possibility
that the natural vitamin E is functionally never fully replaceable with the synthetic vitamin E.

--
Matti Narkia

Wed, 14 Jan 2004 11:57:57 +0200 in article
<[email hidden]> Matti Narkia <[email hidden]>

Quoted message said:

Wed, 14 Jan 2004 03:00:22 +0200 in article <[email hidden]> Matti

Narkia said:

Wed, 14 Jan 2004 00:46:21 +0100 in article <[email hidden]> Thorsten Schier

Quoted message said:

First, alpha-tocopherol has *3* chiral centers which means that there are *8* stereoisomers.

That why nowadays natural alpha-tocopherol is called RRR-alpha-tocopherol whereas the synthetic
one is called all rac-alpha-tocopherol.

So you would have to take eight times as much of the synthetic for the same amount of natural.

I think this still may need more digging up. In Linus Pauling Institute's article about vitamin E
on the web page

<URL:http://lpi.oregonstate.edu/infocenter/vitamins/vitaminE/>

there are citations like this:

"... 200 mg of synthetic alpha-tocopherol (equivalent to 100 mg of RRR-alpha-tocopherol) ..."

"... 50 mg of synthetic alpha-tocopherol (equivalent to 25 mg of RRR-alpha-tocopherol) ..."

"... 400 or 800 IU of synthetic alpha-tocopherol (equivalent to 268 or 536 mg of>RRR-alpha-
tocopherol) ..."

"RRR-alpha-tocopherol (natural or d-alpha-tocopherol): IU x 0.67 = mg RRR-alpha-tocopherol.
Example: 100 IU = 67 mg

all-rac-alpha-tocopherol (synthetic or dl-alpha-tocopherol): IU x 0.45 = mg RRR-alpha-
tocopherol. Example: 100 IU = 45 mg "

Admittedly this article does not take account the negative effect of synthetic vitamin D you
mentioned.

There is another vitamin E article on the same site:

The Biological Activity of Vitamin E Maret G. Traber, Ph.D. Associate Professor of Nutrition LPI
Principal Investigator <URL:http://lpi.oregonstate.edu/sp-su98/vitamine.html>

And I just found a study, which probably is the best reference about the topic at hand:

Burton GW, Traber MG, Acuff RV, Walters DN, Kayden H, Hughes L, Ingold KU. Human plasma and tissue
alpha-tocopherol concentrations in response to supplementation with deuterated natural and
synthetic vitamin E. Am J Clin Nutr. 1998 Apr;67(4):669-84.
<URL:http://www.ajcn.org/cgi/reprint/67/4/669.pdf> (full text)
<URL:http://www.ajcn.org/cgi/content/abstract/67/4/669> (abstract)

Check out also Vitamin E postings by Steven B. Harris, MD, at

<URL:http://yarchive.net/med/vitamin_e.html>

This is part of Norman Yarvin's Usenet Archives collection at

<URL:http://yarchive.net/home.html>

I haven't had much time yet to get familiar with the above study and with the postings by Steven B.
Harris, but right now it appears that

a) RRR-alpha-tocopherol (formerly d-alpha-tocopherol) has about twice the bioavailability of all-rac-alpha-
tocopherol (formerly dl-alpha-tocopherol).

b) A given dose all-rac-alpha-tocopherol has only about 75% of the vitamin activity of the equal
dose of RRR-alpha-tocopherol.

c) From a) and b): A given dose of all-rac-alpha-tocopherol has only 0.50 * .75 = 0.375 = 37.5% of
the vitamin activity of an equal dose of RRR-alpha-tocopherol.

d) Because the serum and tissue bioavailability of vitamin E does not depend linearly on the dose,
i.e. the dose has to be more than double to achieve double levels, therefore, based on the
evidence we have found so far we don't yet know exactly how much synthetic vitamin E (all-rac-alpha-
tocopherol) we have to take to get the same vitamin effect than with a given dose of natural
vitamin E (RRR-alpha-tocopherol). What we do know is that _more_ than the double dose is
required. And even with a dose with the "same" vitamin activity than a given dose of natural
vitamin E, the synthetic vitamin E may have some undesired effects, so there is a possibility
that the natural vitamin E is functionally never fully replaceable with the synthetic vitamin E.

Further reading about the topic:

A Comparison of Natural and Synthetic Vitamin E Research Summary April 1999 <cognis-cognis-Open ↗
us.com/framescout.html?/cognis/nutritionandhealth/private/productinformation/research/natsynth.htm>

A COMPARISON OF NATURAL-SOURCE AND SYNTHETIC VITAMIN E June 2002
<URL:http://www.cognis.com/cognis/testveris/Vitamin%20E%20June02.pdf>

Kiyose C, Muramatsu R, Kameyama Y, Ueda T, Igarashi O. Biodiscrimination of alpha-tocopherol
stereoisomers in humans after oral administration. Am J Clin Nutr. 1997 Mar;65(3):785-9.
<URL:http://www.ajcn.org/cgi/content/abstract/65/3/785>

Stone WL, LeClair I, Ponder T, Baggs G, Reis BB. Infants discriminate between natural and synthetic
vitamin E. Am J Clin Nutr. 2003 Apr;77(4):899-906.
<URL:http://www.ajcn.org/cgi/content/abstract/77/4/899>

Brigelius-Flohe R, Traber MG. Vitamin E: function and metabolism. FASEB J. 1999 Jul;13(10):1145-55.
Review. <URL:http://www.fasebj.org/cgi/content/full/13/10/1145>

Lauridsen C, Engel H, Craig AM, Traber MG. Relative bioactivity of dietary RRR- and all-rac-alpha-
tocopheryl acetates in swine assessed with deuterium-labeled vitamin E. J Anim Sci. 2002 Mar;80(3):702-
7. PMID: 11890405 [PubMed - indexed for MEDLINE] <URL:http://jas.fass.org/cgi/reprint/80/3/702.pdf>
(full text) <URL:http://jas.fass.org/cgi/content/abstract/80/3/702> <URL:http://www.ncbi.nlm.nih.go-
v/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11890405&dopt=Abstract>

Lauridsen C, Engel H, Jensen SK, Craig AM, Traber MG. Lactating sows and suckling piglets
preferentially incorporate RRR- over all-rac-alpha-tocopherol into milk, plasma and tissues. J Nutr.
2002 Jun;132(6):1258-64. PMID: 12042443 [PubMed - indexed for MEDLINE]
<URL:http://www.nutrition.org/cgi/content/full/132/6/1258> (full text) <URL:http://www.ncbi.nlm.nih-
.gov/entrez/query.fcgi?cmd=retrieve&db=pubmed&list_uids=12042443&dopt=Abstract>

Leonard SW, Terasawa Y, Farese RV Jr, Traber MG. Incorporation of deuterated RRR- or all-rac-alpha-
tocopherol in plasma and tissues of alpha-tocopherol transfer protein--null mice. Am J Clin Nutr.
2002 Mar;75(3):555-60. PMID: 11864863 [PubMed - indexed for MEDLINE
<URL:http://www.ajcn.org/cgi/content/full/75/3/555> <URL:http://www.ncbi.nlm.nih.gov/entrez/query.f-
cgi?cmd=Retrieve&db=PubMed&list_uids=11864863&dopt=Abstract>

Traber MG, Elsner A, Brigelius-Flohe R. Synthetic as compared with natural vitamin E is
preferentially excreted as alpha-CEHC in human urine: studies using deuterated alpha-tocopheryl
acetates. FEBS Lett. 1998 Oct 16;437(1-2):145-8. PMID: 9804189 [PubMed - indexed for MEDLINE]
<URL:http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=9804189&dop-
t=Abstract>

Traber MG, Rader D, Acuff RV, Ramakrishnan R, Brewer HB, Kayden HJ. Vitamin E dose-response studies
in humans with use of deuterated RRR-alpha-tocopherol. Am J Clin Nutr. 1998 Oct;68(4):847-53.
<URL:http://www.ajcn.org/cgi/reprint/68/4/847.pdf> (full text) <URL:http://www.ncbi.nlm.nih.gov/ent-
rez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=9771861&dopt=Abstract>

Dietary Reference Intakes for Vitamin C, Vitamin E, Selenium, and Carotenoids
(2000)Vitamin E <URL:http://books.nap.edu/books/0309069351/html/186.html#pagetop>

Tocopherol (Vitamin E) in Health and Disease <URL:http://www.medicine.uiowa.edu/frrb/VirtualSchool/Veris-
TOH.ppt>

Nomenclature of Tocopherols and Related Compounds
<URL:http://www.chem.qmul.ac.uk/iupac/misc/toc.html>

Natural vs. Synthetic Vitamin E by Jack Challem
<URL:http://www.newhope.com/nutritionsciencenews/NSN_backs/Nov_01/lastword.cfm>

Two New Studies Find Natural Vitamin E Better Absorbed, Retained Than Synthetic By Jack Challem
<URL:http://www.thenutritionreporter.com/natural_vitamin_e.html>

Natural Vitamin E retained two times better than synthetic
<URL:http://www.sdearthtimes.com/et0698/et0698s13.html>

--
Matti Narkia