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SEARCH LOG -- Hamna Riaz Comp# 23
Search for a phytochemical found in Gogi berry (Lycium barbarum) – Beta-Sitosterol (also called cinchol)
The first part of the search log consists of sources of information found by searching Web sites.
General Information/Web
Google: (Google requires uppercase OR)

search term hits

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Lycium barbarum 5630

http://www.benefitsofgojiberries.com/

Lycium barbarum also known as “goji berry”


Goji health benefits 33000

http://www.timpanogosnursery.com/site/928760/page/416906

Ways to grow goji (soil type, temperature)

Beta-sitosterol is a beneficial chemical component in them because it is a vasodilator

Contains essential antioxidants.



http://www.vrp.com/articles.aspx?ProdID=art2288&zTYPE=2

Predominantly recognized benefits in China, Himalayas and Thailand. Grows in adundance, not endangered.



http://plants.usda.gov/java/nameSearch

Botanical information of the goji berry.



http://www.uncleharrys.com/infobase/product/goji_berries.php

History of goji berries. Used throughout time to promote health in Asia.

Search within above results for

Goji and Antioxidant 4690

http://gojiscientific.org/

Goji experiment: “Mice were exposed to Hypoxia which means a subnormal concentration of oxygen. In other words by putting the mice in an enclosed bottle they used up the oxygen.


Evidence of increased free radical defending systems were found in the subject mice which means that there was the increased presence of antioxidants. Oxidation is like rust on metal though it happens in the body all the time resulting in cellular stress, lack of energy (fatigue) and the break-down of the body’s’ immune system… Superoxide dismutase found in Goji berries serves a key antioxidant role keeping cells from getting worn out.” Source: researcher, Jeff Scott (2007)
beta-sitosterol 136

http://www.drugs.com/npp/beta-sitosterol.html

Adverse effects to consuming Beta-sitosterols in Goji: “The most important concern about plant sterols is that they reduce the absorption of the fat-soluble vitamins β-carotene, α-carotene, and vitamin E. No effects on vitamins A and K have been noted.”

http://www.hmdb.ca/metabolites/HMDB00852

Beta-sitosterol: gives properties, chemistry, IUPAC name and chemical structure.

Another name: cinchol

Melting Point: 140oC


cinchol OR beta-siosterol and goji 1

http://www.goodhealthco.com/full_product/prostate601.html

Goji berries used for prostate health



cinchol or beta-sitosterol and lycium 2

http://www.naturaldatabase.com/(S(evmsx445v3at2li0x4kjct45))/nd/Search.aspx?cs=&s=ND&pt=100&sh=6&id=939

pharmacology, chemical components and ingredients in beta-sitosterol products. Induce cellular apoptosis


Apoptosis Definition

http://www.sgul.ac.uk/depts/immunology/~dash/apoptosis/

apoptosis definition (what goji berries can induce in tumor cells)


Searching within “beta-sitosterol” for

Tumor treatment 9

http://www.phytochemicals.info/phytochemicals/beta-sitosterol.php

“Epidemiological and experimental studies have suggested a protective role of beta-sitosterol in the development of some types of cancer such as breast, colon and prostate cancer. In-vivo studies have shown that the phytochemical inhibited proliferation and induce apoptosis in human solid tumors such as colon and breast cancers.” Induces cellular proliferation.



Chemical names: (3beta)-stigmast-5-en-3-ol, 22:23-dihydrostigmasterol, alpha-dihydrofucosterol, cinchol, cupreol, rhamnol, quebrachol and sitosterin.

Source: Top Cultures (a Belgium based phytochemical research lab)


http://www.ncbi.nlm.nih.gov/pubmed/16563441?dopt=Abstract

other benefits of goji: testicular health benefits

Goji and Cellular proliferation 2,300

http://www.curehunter.com/public/pubmed17603173.do

abstract for usage of beta-sitosterol in experiment to induce cellular apoptosis and as an anti-proliferator.

Searching within above results for

Tumor treatment 1020

http://www.gojibook.com/BR07.html

Pharmacological Effects: Dr. Earl Mendell, PhD: “Goji is one of the only plant species on earth that contains the anti-cancer mineral germanium. Its antioxidants and unique polysaccharides can halt the genetic mutations that can lead to cancer.” Source: from his book The Himalayan Health Secret
http://www.mayoclinic.com/health/prostate-gland-enlargement/DS00027

Discusses goji’s uses for prostate health. Defines prostate disorders: “…cells in the central portion reproduce more rapidly, resulting in prostate gland enlargement. As tissues in the area enlarge, they often compress the urethra and partially block urine flow. Benign prostatic hyperplasia (BPH) is the medical term for prostate gland enlargement.” Source: Mayo Clinic Staff, 2007



Synthesis of Beta-Sitosterol 814

http://www3.interscience.wiley.com/journal/112693422/abstract

P. P. H. H. L. Otto, A. C. Besemer, W. H. J. M. Wientjens, Journal of Labelled Compounds, 6,2, 2006. Pages 111-123. DOI: 10.1002/jlcr.2590060202.



Database: Wiley Interscience found and will now be used to research beta-sitosterol

Methods to synthesize beta-sitosterol described briefly:

“Starting from stigmasterol, the complete synthesis consists of eleven reaction steps. It is based on methods described in the literature. For some of the steps, a considerable improvement in yield has been achieved. The actual labelling step is the condensation of 4-oxa-5-stigmasten-3-one with phenyl acetate-14C in the presence of sodium hydride. -Sitosterol-3-14C has been obtained with a chemical yield of 23 %, based on 4-oxa-5-stigmasten-3-one. The radiochemical yield was 10.3 %. Chemical and radiochemical purities of -sitosterol-3-14C have been determined by means of thin-layer chromatography, gas-liquid chromatography and mass spectrometry.”

Can by synthesized from crude plant sterols then converted to beta-sitosterol.

This second part consists of searches done using online databases



Scirus

search term hits

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Beta-sitosterol Goji 5 (in pubmed central)

http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=2650746&tool=pmcentrez

doi: 10.1002/ptr.2636. 22, March 2009



Full length article!

Acknowledgement of the growth of alternative, natural treatments in modern ages (called CAM or complementary and alternative medicine).

“This herb root is also known to contain sapogenins, phytosterols, beta-sitosterol and campesterol, which may contribute in part to the tumoricidal properties (Dr Dukes Chemical Database)”

http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=419367&tool=pmcentrez

Jones, Burger, Abumweis. Lipids Health Dis. 2004; 3, 5.

“Plant sterols: factors affecting their efficacy and safety as functional food ingredients” doi: 10.1186/1476-511X-3-5. 22, March 2009

Full Length Article!

Beta-sitosterol is a plant sterol and “In addition to their cholesterol lowering properties, plant sterols possess anti-cancer, anti-inflammatory, anti-atherogenicity, and anti-oxidation activities, and should thus be of clinical importance, even for those individuals without elevated LDL cholesterol.”



Lycium barbarum (goji)

Amagase, Harunobu; Sun, Buxiang; Borek, Carmia, Nutritional Research 2009, 29, 1.Lycium barbarum (goji) juice improves in vivo antioxidant biomarkers in serum of healthy adults” doi:10.1016/j.nutres.2008.11.005. 22, March 2009

Lycium barbarum preparation (GoChi) helps prevent oxidant stress-related conditions in humans, our present study examined the hypothesis that the antioxidant effects of GoChi result from its ability to enhance endogenous antioxidant factors…GoChi increased antioxidant efficacies in humans by stimulating endogenous factors and suggest that continued use beyond 30 days might help prevent or reduce free radical-related conditions”

Under “Related Articles in ScienceDirect” for Lycium barbarum:

Li, XM; MA, Y.L; Liu, X.J, Journal of Ethnopharmacology 2007, 111, 3. “Effect of the Lycium barbarum polysaccharides on age-related oxidative stress in aged mice” doi:10.1016/j.jep.2006.12.024. 22, March 2009

“Antioxidant activities of Lycium barbarum polysaccharides can be compable with normal antioxidant, vitamin C. Moreover, addition of vitamin C to the polysaccharides further increased the in vivo antioxidant activity of the latter. It is concluded that the Lycium barbarum polysaccharides can be used in compensating the decline in TAOC, immune function and the activities of antioxidant enzymes and thereby reduces the risks of lipid peroxidation accelerated by age-induced free radical.”

ACS

search term hits

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Lycium barbarum and Apoptosis 1

http://pubs.acs.org/action/showMultipleAbstracts

J. Agric. Food Chem., 2008, 56 (3), pp 630–635 “Berry Fruits for Cancer Prevention: Current Status and Future Prospects”

DOI: 10.1021/jf072504n, 22, March 2009

“Studies show that the anticancer effects of berry bioactives are partially mediated through their abilities to counteract, reduce, and also repair damage resulting from oxidative stress and inflammation. In addition, berry bioactives also regulate carcinogen and xenobiotic metabolizing enzymes, various transcription and growth factors, inflammatory cytokines, and subcellular signaling pathways of cancer cell proliferation, apoptosis, and tumor angiogenesis.”

Beta-sitosterol Characterization 6

http://pubs.acs.org.mutex.gmu.edu/doi/abs/10.1021/jf00115a012?prevSearch=beta-sitosterol+boiling+point&searchHistoryKey=

J. Agric. Food Chem., 1983, 31 (1), pp 46–50 “Characterization of some oxidation products of .beta.-sitosterol” DOI: 10.1021/jf00115a012

This article was written in 1983, when the connection between beta-sitosterol and its affects on cancer cells was unknown. The researcher in this article attempted to isolate the product then oxidize it to study how it can affect tumor cells. Isolation of beta-sitosterol is discussed.


Science Direct (Elsevier)

search term hits

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Lycium barbarum + Cancer 91

Milbury, Paul E. Complementary and Alternative Therapies and the Aging Population


2009, Pages 347-370
, “Berries and Cancer” doi:10.1016/B978-0-12-374228-5.00017-2 22, March 2009

In vitro experiments have contributed much to the knowledge base regarding probable mechanisms of action that support chemoprotective activities of berry phytochemicals at the molecular level. These chemopreventive mechanisms include prevention of radical damage, DNA stabilization, detoxification, inhibition of inflammatory processes such as cyclooxygenase-2 expression, and induction of apoptosis.”

3D Chemical structure also provided in this article.


PubChem

search term hits

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Beta-sitosterol 25

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=56310589&loc=es_rss#Subinfo

Sitosterol-Substance Summary. 22, March 2009

Molecular weight: 414.7067 [g/mol]

Chemical Formula: C29H50O

Beta-sitosterol Synthesis

http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=2048776&tool=pmcentrez&rendertype=abstract

Chen, Steinhauer, Hammerlindl, Plant Physiol. 2007 November; 145(3): 974–984.

doi: 10.1104/pp.107.106278

synthesis of beta-sitosterol from other sterols in plants



http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=535768&tool=pmcentrez

Salen, Gerald; Ahrens, E.H; Grundy, Scott M .J Clin Invest. 1970 May; 49(5): 952–967. “Metabolism of β-sitosterol in man”

doi: 10.1172/JCI106315

Human metabolism of beta-sitosterols = more efficient than animal cholesterol


Spectral Database for Organic Compounds

search term hits

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Beta-sitosterol (none)

The CAS registration number for beta-sitosterol was then googled with a total of 50,400 hits and the search was performed again using the CAS number instead of the name

[83-46-5] 1

http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi

2D structure given as well as IR (prominent stretching before the 3000cm-1 region indicating that it is an



Aromatic compound. More bending in the 1300 region, indicating the presence of a C—O bond)


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