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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 ----------------------------------------------------------------------------------------------------- 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 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
abstract for usage of beta-sitosterol in experiment to induce cellular apoptosis and as an anti-proliferator. Searching within above results for
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- 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 ----------------------------------------------------------------------------------------------------- Beta-sitosterol Goji 5 (in pubmed central)
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)”
“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” “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.”
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“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
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 ----------------------------------------------------------------------------------------------------- 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.
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Sitosterol-Substance Summary. 22, March 2009 Molecular weight: 414.7067 [g/mol] Chemical Formula: C29H50O Beta-sitosterol Synthesis
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 ----------------------------------------------------------------------------------------------------- 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
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) |
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-