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- Scyllitol -

General Information:

Names:
Wikipedia entry:
Dr. Ray Shahelien entry: 

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Observations:

Scyllitol (scyllo-inositol, cocositol, quercinitol)

Myo-Inositol
[Often referred to as "inositol".  Not the same as Scyllitol.]

Scyllitol (scyllo-inositol) is one of the six naturally occuring isomers of cyclohexanehexol.

According to a paper published in the journal Nature Medicine on June 11, 2006, mice genetically engineered to have Alzheimer's disease when fed scyllitol either did not develop the disease, or recovered most mental function and life expectancy of normal mice.

Upon some research on the web, it turns out that scyllitol is a naturally occuring sugar found in many plants and in soil, (presumably synthesized by bacteria).  Interestingly, the most abundant source I've found so far is coconut palm leaves, and coconut milk.  However, at something like 5 parts per million, you would probably have to consume enormous quantities of coconut milk to get a dose of scyllitol to have an effect.  But the real significance of this is that scyllitol is a naturally occuring substance found in food, and therefore, could not be patented.  Supplement makers should be able to extract it from food sources.  Perhaps the bacteria responsible for the presence of scyllitol in soil could be identified, and then used in sort of a fermentation process.

But since the chemical can not be patented, I envision that it will be denounced as "quack medicine", "dangerous", or whatever; in order to discourage it's manufacture and use.  In my opinion, this is a major breakthrough, and no delay should be allowed in bringing it to mass availability.  Since it's already present in our food, at most, it won't do anything.

It is interesting that US Patent # 4847082 was filed by Robert Sabin on January 21, 1987 for a "Method of treatment of Alzheimer's disease using phytic acid".  That was over 19 years ago.  The patent sould have expired by now.

More info:  Human Metabolome Database

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Known sources:


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Natural sources:

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References:

Graviola is a fruit tree native to North and South America and the
Caribbean, where it is known by such names as Paw-Paw, Soursop, and
Guanabana. The species native to South America is the Guanabana tree, and
it is prized for its fruit, which is used in drinks, ice cream, and
marmalades.

[Source of scyllitol?]
http://www.amazonnaturalherbs.com/graviola.htm

Scyllitol (scyllo-inositol, cocositol, quercinitol, 1,3,5/2,4,6-Hexahydroxycyclohexane,
             CAS RN: 488-59-5 Mol. Formula: C6H12O6)

Scyllitol
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=892

Scyllo-inositol treatment of Alzheimer's disease
 
"Certain variants of a simple sugar ameliorate Alzheimer's-like disease in mice, according to a new study by Canadian researchers."
scyllo-inositol
http://groups.google.vg/group/misc.health.alternative/browse_thread/thread/1f4bda3485a8dd1a?hl=en
 
A Sweet Solution to Alzheimer's Disease?
 
"The new studies show that some types of a sugar called cyclohexanehexol—also known as inositol—prevented the accumulation of amyloid β deposits, a hallmark of Alzheimer's disease. Scyllo-inositol treatment also improved cognitive abilities in the mice and allowed them to live a normal lifetime. The study appeared in advance online publication of the journal Nature Medicine on June 11, 2006."
http://www.hhmi.org/news/stgeorgehyslop20060612.html

A Sweet Solution For Alzheimer's Disease?
 
"Certain variants of a simple sugar ameliorate Alzheimer's-like disease in mice, according to a new study by Canadian researchers. Although the new studies are still in the early stages, the findings could lead to new therapies that prevent or delay the onset of Alzheimer's disease. The new studies show that some types of a sugar called cyclohexanehexol--also known as inositol--prevented the accumulation of amyloid â deposits, a hallmark of Alzheimer's disease. Scyllo-inositol treatment also improved cognitive abilities in the mice and allowed them to live a normal lifetime. The study appeared in advance online publication of the journal Nature Medicine on June 11, 2006."
http://www.medicalnewstoday.com/medicalnews.php?newsid=45078

A Sweet Solution to Alzheimer's Disease?

Sugar restored cognitive ability, returned mice to live normal lives

June 13, 2006 - "Certain variants of a simple sugar cause improvement in Alzheimer's-like disease in mice, according to a new study by Canadian researchers. Although the new studies are still in the early stages, the findings could lead to new therapies that prevent or delay the onset of Alzheimer's disease.

"The new studies show that some types of a sugar called cyclohexanehexol—also known as inositol—prevented the accumulation of amyloid B deposits, a hallmark of Alzheimer's disease.

"Scyllo-inositol treatment also improved cognitive abilities in the mice and allowed them to live a normal lifetime. The study appeared in advance online publication of the journal Nature Medicine on June 11, 2006."
http://www.seniorjournal.com/NEWS/Alzheimers/6-06-13-ASweetSolution.htm

"13 June 2006. The news this week brings four papers describing different approaches to prevent or treat neurodegeneration. From an inhibitor of aggregation and a DNA vaccine targeted at amyloid-β (Aβ), to a kinase inhibitor for tau and a kinase target in Parkinson disease, there’s plenty to read and heed in these reports.
In the first, JoAnne McLaurin, Peter St. George-Hyslop, and colleagues at the University of Toronto show that certain orally delivered cyclohexanehexol (aka inositol) stereoisomers can block the accumulation of soluble Aβ oligomers in the brain of transgenic mice. The compounds reverse memory deficits (as measured by performance in the Morris water maze), reduce plaque load, and reverse other signs of Aβ pathology. The results strengthen the case that high-molecular-weight oligomers of Aβ (like Aβ*, see ARF related news story) play a major role in producing memory deficits in mice, and pave the way for the testing of these inositols to prevent or reverse Alzheimer disease in people. A phase I trial of their most effective compound, scyllo-inositol, has just been launched under the name AZD-103."
http://www.alzforum.org/new/detail.asp?id=1414

Cyclohexanehexol inhibitors of Abeta aggregation prevent and reverse Alzheimer phenotype in a mouse model.

"When given orally to a transgenic mouse model of Alzheimer disease, cyclohexanehexol stereoisomers inhibit aggregation of amyloid beta peptide (Abeta) into high-molecular-weight oligomers in the brain and ameliorate several Alzheimer disease-like phenotypes in these mice, including impaired cognition, altered synaptic physiology, cerebral Abeta pathology and accelerated mortality. These therapeutic effects, which occur regardless of whether the compounds are given before or well after the onset of the Alzheimer disease-like phenotype, support the idea that the accumulation of Abeta oligomers has a central role in the pathogenesis of Alzheimer disease."
http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&dopt=Abstract&list_uids=16767098

Characterization of scyllo-inositol-containing phosphatidylinositol in plant cells.
 
"The structure of in vivo [3H]myo-inositol-labeled phosphatidylinositols in barley seeds were investigated by chemical degradation. In this report we present data that suggests the presence of scyllo-inositol-containing phosphatidylinositol in addition to the commonly occurring myo-inositol-containing phosphatidylinositol."
http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=7755633&dopt=Abstract
 
Identification of scyllo-Inositol Phosphates in Soil by Solution Phosphorus-31 Nuclear Magnetic Resonance Spectroscopy
 
"A large proportion of the organic P in soils can occur as scyllo-inositol phosphates. These compounds are rarely detected elsewhere in nature and remain poorly understood, partly because conventional procedures for their determination are lengthy and erroneous. We report a straightforward procedure for the determination of scyllo-inositol phosphates in soil extracts using solution 31P nuclear magnetic resonance (NMR) spectroscopy. Solution 31P NMR chemical shifts of a range of synthetic scyllo-inositol phosphate esters were determined in alkaline solution. Of these, only the signal corresponding to scyllo-inositol hexakisphosphate at approximately 4.2 ppm was identified in soil NaOH–EDTA extracts, constituting between 6.5 and 9.8% of the NaOH–EDTA extracted P."
http://soil.scijournals.org/cgi/content/abstract/68/3/802
 
Quantification and bioavailability of scyllo-inositol hexakisphosphate in pasture soils
 
From the PDF...
"Results from both re-analyzed datasets provide tentative evidence that nutrient status regulates scyllo-inositol hexakisphosphate in soil. In particular, it was inversely correlated with nitrogen-to-organic phosphorus ratios and was degraded by ryegrass only in low-nutrient soils. This suggests that phosphorus limitation favours organisms that can access recalcitrant inositol phosphates in the soil, such as Aspergillus ficuum or Pseudomonas spp. Conversely, accumulation of scyllo-inositol hexakisphosphate following the growth of ryegrass in high nutrient soils indicates synthesis by microbes under phosphorus-sufficient conditions."
http://striweb.si.edu/inositol_conference/program/PDFs/tuesday_morning/Condron.pdf

Identification of L-Inositol and Scyllitol and Their Distribution in Various Organs in Chrysanthemum
 
Kazuo ICHIMURA1), Katsunori KOHATA1), Yuichi YAMAGUCHI1), Mitsuru DOUZONO1), Hiroshi IKEDA1) and Mamoru KOKETSU2)
 
1) National Research Institute of Vegetables, Ornamental Plants and Tea
2) Faculty of Engineering, Gifu University
 
(Received September 16, 1999)
(Accepted December 24, 1999)
 
"Two unidentified soluble carbohydrates were isolated from chrysanthemum (Dendranthema×grandiflorum (Ramat.) Kitamura) leaves using HPLC. The compounds were identified as 1 L-chiro-inositol, called L-inositol (1) and scyllo-inositol, called scyllitol (2) from the results of 1H-NMR, 13C-NMR, and CI-MS spectra. L-Inositol and scyllitol were distributed in four cultivars tested. L-Inositol concentration of petals gradually decreased during the flower bud development, but the L-inositol content increased by about 7 times. Scyllitol was detected only at an early stage of flower bud."
http://www.jstage.jst.go.jp/article/bbb/64/4/64_865/_article
 
Nomenclature of Cyclitols
 
Cyclitols with only hydroxyl or substituted hydroxyl groups
http://www.chem.qmul.ac.uk/iupac/cyclitol/I1t5.html

Dr. Duke's Phytochemical and Ethnobotanical Databases
 
SCYLLITOL

Plant species with highest amount
Cocos nucifera L. -- Coconut, Coconut Palm, Cocotero (Sp.), Copra, Kokospalme (Ger.), Nariyal; 3,200 ppm in Leaf; 500 ppm in Endosperm;
Annona muricata L. -- Soursop; in Plant;
Arecastrum romanzoffianum (CHAM.) BECC. -- Feathery coconut, Queen palm; in Plant WO2;
Cornus florida L. -- American Dogwood; in Flower;
Quercus alba L. -- White Oak; in Bark;
Quercus robur L. -- English Oak; in Bark;
http://www.ars-grin.gov/cgi-bin/duke/chemical.pl?SCYLLITOL

scyllo-Inositol [I1060]
Alternative Product ID: Scyllito
Description: Natural occurring isomer of myo-inositol, product # I-1058.
Chemical Formula: C6H12O6
Molecular Weight: M.W.180.2
Solubility: Soluble in Water.
Active Product: N
Appearance: Crystalline Solid
Purity: >99%
Storage: Room Temperature.
Shipping: Priority Courier
Bulk Quantity: Inquire
 
http://www.agscientific.com/Item/I1060.htm

Cat. Number: I666050  CAS Number: 488-59-5
Chemical Name:  scyllo-Inositol
Synonym:  Scyllitol, Cocositol,
Quercinitol,1,3,5/2,4,6-Hexahydroxycyclohexane
Mol. Formula:  C6H12O6
Mol. Weight:  180.16
  Melting Point: 348.5-350°C
Boiling Point:
Appearance: White Crystalline Solid
Application Notes:
 
References:
Carbohydrate Res., 307, 163 (1998)
http://trc-canada.com/product.lasso?product=I666050

New conditions for the synthesis of scyllo-inositol starting from
myo-inositol

Christian Husson, Léon Odier1 and Ph. J. A. Vottéro*

CEA-Grenoble/Département de Recherche Fondamentale sur la Matière
Condensée, Service de Chimie Inorganique et Biologique, Laboratoire de
Reconnaissance Ionique, 17, rue des Martyrs, F-38041 Grenoble, France

Received 27 October 1997; accepted 18 December 1997. Available online 25
May 2000.

Abstract
Equilibration of myo-inositol by Raney nickel in water has been
reconsidered on a preparative scale. An efficient separation of
scyllo-inositol by orthoacetate derivatization of the components of the
crude mixture is proposed which gives the free scyllo-inositol in good
yield.

Author Keywords: Scyllo-inositol; Myo-inositol; Catalytic equilibration
 
1Also member of the Université Joseph Fourier, Grenoble 1, France.

*Corresponding author. Fax: 0033 4 76 88 50 90.

Carbohydrate Research
Volume 307, Issues 1-2 , February 1998, Pages 163-165
http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TFF-40BG3V2-19&_coverDate=02%2F28%2F1998&_alid=420890772&_rdoc=1&_fmt=&_orig=search&_qd=1&_cdi=5225&_sort=d&view=c&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=6979693f38411f0f226b55a9e40004c4

Sulfonate protecting groups. Improved synthesis of scyllo-inositol and its
orthoformate from myo-inositol.
http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12681925&dopt=Abstract

SCYLLITOL FROM FLOWERING DOGWOOD (CORNUS FLORIDA).
BY RAYMOND M. HANN AND CHARLES E. SANDO.
(From the Bureau of Chemistry and the Bureau of Plant Industry, United
States Department of Agriculture, Washington.)

"Scyllitol, CGH6(OH)6, was first isolated in 1858 by Staedeler
and Frerichsl from the kidneys and other organs of certain plagiostomous
fishes. It has since been found in acorns,2J3 in the
leaves of Cocos plumosa and Cocos nucifera,4 and in the leaves
of He&nus ovatus.5 As a result of the present investigation, the
flowering dogwood, Cornus Jlorida, may be added as another
source of the compound."
http://www.jbc.org/cgi/reprint/68/2/399

On the Inositol of Brain and its Preparation
Goro Momose

The Physiological Laboratory, King's College, London
http://www.pubmedcentral.gov/articlerender.fcgi?artid=1258694

Hexitols in coconut milk: Their role in nurture of dividing cells 1
J. K. Pollard, E. M. Shantz, and F. C. Steward

Department of Botany, Cornell University, Ithaca, New York
http://www.pubmedcentral.gov/articlerender.fcgi?artid=406171

Center for Plant Cell Biology, UC Riverside
http://bioweb.ucr.edu/ChemMine/view.php?TYPE=1&i_id=920029

The Comparative Toxicogenomics Database (CTD) identifies interactions
between chemicals and genes/proteins in diverse organisms to elucidate the
molecular mechanisms by which environmental chemicals affect human health.
http://ctd.mdibl.org/voc.go;jsessionid=8F50D909C61F6F6C4DA982C4529175E9?voc=chem&acc=C009217

High cerebral scyllo-inositol: a new marker of brain metabolism disturbances induced by chronic alcoholism.
Viola A, Nicoli F, Denis B, Confort-Gouny S, Le Fur Y, Ranjeva JP, Viout
P, Cozzone PJ.
Centre de Resonance Magnetique, Biologique et Medicale UMR CNRS 6612,
Faculte de Medecine, 27 Bd J. Moulin, 13005 Marseille, France.

Magnetic Resonance Materials in Physics, Biology and Medicine
Publisher: Springer Berlin / Heidelberg
ISSN: 0968-5243 (Paper) 1352-8661 (Online)
DOI: 10.1007/s10334-004-0044-x
Issue:  Volume 17, Number 1

Date:  September 2004
Pages: 47 - 61

Our results suggest that scyllo-inositol is produced within the central nervous system and shows a diffuse but heterogenous distribution in brain where it can persist several weeks after detoxification. Its highest levels were observed in subjects with a clinically symptomatic alcohol-related encephalopathy. When detected, brain scyllo-inositol takes part in a metabolic encephalopathy since it is associated with reduced N-acetylaspartate and increased creatine. High levels of cerebral scyllo-inositol are correlated with altered glial and neuronal metabolism. Our findings suggest that the accumulation of scyllo-inositol may precede and take part in the development of symptomatic alcoholic metabolic encephalopathy.

PMID: 15340856 [PubMed - indexed for MEDLINE]

[Whoa!  Interesting.  Can alcohol consumption cause scyllitol to be created by the CNS?  Or is it a component of the alcoholic beverage?  If scyllitol breaks down amyloid beta plaques, then could a drinking binge rid the brain of amyloid????  ??????  What relationship is there between alcoholism and AD?  Alcohol consumption and AD?  Too much scyllitol causes problems.  Could the CNS be producing scyllitol as a defense mechanism against the constant onslaught of alcohol?  In the case of AD, the CNS just isn't producing enough.  Here is a study that shows alcohol isn't a factor:  http://bjp.rcpsych.org/cgi/content/abstract/163/3/358 ]

http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=pubmed&cmd=Retrieve&list_uids=15340856&itool=pubmed_Abstract&dopt=abstractplus&dr=abstractplus

Keystone Drug News: Phase 2 Anti-oligomer Sugar Alcohol—How Might It Work?
http://www.alzforum.org/new/detail.asp?id=1792

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