Mike Adams
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 Preliminary results indicated that flaxseed oil can exert powerful anticancer properties if the oil is high in lignan precursors. Unfortunately, despite the incredible promise of preliminary results, the NCI canceled the project before it was completed. Nonetheless, there is substantial evidence that suggests flaxseed oil exerts significant anticancer properties.
- Michael T. Murray, N.D. |
Dr. Michael Heinrich, Joanne Barnes, Simon Gibbons and Elizabeth M. Williamson
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 The main natural product is the podophyllotoxin lignan class (see Chapter 6) of which podophyllotoxin was the first to be isolated in 1880 and the structure proposed in 1932. There are many components in podophyllin; the most important from the antitumour perspective are the lignans. Podofllox is a purified form of podophyllin which acts as a cell poison against cells undergoing mitosis, and although this extract is not a systemic chemotherapeutic agent it is used topically in creams as a treatment for genital warts. |
| Indian podophyllum, contains these active lignan ingredients at a lower concentration. Podophyllotoxin and related lignans are also found in the rhizomes of another species P. pleianthum, which in Japan and China is used to make a preparation to treat snakebites and tumours of the genitals.
The rhizomes of P. peltatum have a long history as a medicine among native North American tribes (Penobscot Indians of Maine). They are gathered in autumn, dried and ground to a powder, the material being eaten or drunk as an infusion of the powder as a laxative or to get rid of intestinal worms. |
by Michael Murray, N.D. and Joseph Pizzorno, N.D.
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| HEALTH BENEFITS
The major health benefits of flaxseeds are derived from their alpha-linolenic acid and lignan content. Flaxseed oil contains nearly twice the level of omega-3 fatty acids as fish oil, although it contains the shorter-chain alpha-linolenic aci I rather than the longer-chain fats, such as eicosapentaenoic acid (EPA) and docosa-hexaenoic acid (DHA). |
Leslie Taylor, ND
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 Scientists have attributed many of the biologically active properties of the sap (especially its wound-healing capacity) to two main "active" constituents: an alkaloid named taspine, and a lignan named dimethylcedrusine.
Of course, botanists, herbalists, and naturopaths would disagree with such reductionist conclusions (and often do); in this particular case, the matter is actually proven by science. Noted author and ex-USDA economic botanist Dr. |
Simon Mills and Kerry Bone
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 Dietary studies and assays of urinary lignans in postmenopausal women showed that lignan excretion is significantly lower in the urine of women with breast cancer.291
Adverse reactions and toxicology
Epidemiological studies have not found adverse effects from dietary consumption of isoflavones or lignans. However, if quantities well above dietary exposure are used in a therapeutic context, adverse events might well ensue. The phytooestrogens are partial oestrogen agonists similar to the drug tamoxifen. |
Bryan Hanson, PhD
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 Podophyllotoxin, a lignan shown earlier in Figure 4.28, is known to inhibit microtubule assembly by binding at the same site as cholchicine. However, podophyllotoxin is too toxic for clinical use against cancer, and researchers have modified the structure slightly to create two useful molecules called etoposide and teniposide. Curiously, in spite of very similar structures, these two drugs don't affect tubulin as podophyllotoxin does, but instead they treat cancer by inhibiting topoisomerase II. Sometimes a very small structural modification changes the entire mode of action. |
National Women's Health Network
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 Lignan precursors are found in whole grains, seeds, fruits, and vegetables—especially flaxseed, rye, millet, and legumes. Isoflavone precursors are found in soybeans, chickpeas, and other legumes.2'3 Bacteria in our intestines convert plant lignans to mammalian lignans (enterolactone and enterodiol) and convert isoflavone precursors to active isoflavones (genistein, daidzein, and equol). |
Laurie Deutsch Mozian, M.S., R.D.
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 Flaxseed
Flaxseed is an extremely rich source of lignans. lignan bears a structural resemblance to estrogen and can bind to estrogen receptors and inhibit the growth of estrogen-stimulated cancers. In addition, when the omega-3 fatty acid content of flaxseed oil is metabolized, it results in the production of the prostaglandin PG3, a hormonelike substance that enhances the functioning of the immune system.
Phytochemical-Rich Foods That Appear to Be Promising in Fighting Cancer
The following foods are not quite as well studied but appear to have potential in fighting cancer. |
Mark Blumenthal
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 Eleutheroside D is the lignan (-)-syringaresinol di-0-|3-D-gluco-side, and its diastereoisomer is eleutheroside E (Bradley, 1992; Farnsworth et al, 1985). Eleuthero also contains immunostimu-lant polysaccharides (Fang et al, 1985; Huang, 1999). An extensive review of the chemistry of eleuthero with 29 chemical structures has been published (Tang and Eisenbrand, 1992). |
| Mazur WM, Rasku S, Salakka A, et al. lignan and isoflavonoid concentrations in tea and coffee. Br J Nutr 1998;79:37-45.
McGuffin M, Hobbs C, Upton R, Goldberg A (eds.). American Herbal Products Associations Botanical Safety Handbook. Boca Raton, FL: CRC Press; 1997.
McManus R, Jumson J, Finegood D, et al. A comparison of the effects of n-3 fatty acids from linseed oil and fish oil in well-controlled type 1 diabetes. Diabetes Care 1996;19(5):463-7.
Medical Products Agency (MPA). Naturlakemedel: Authorised Natural Remedies (as of January 24, 2001). |
| Flaxseed and its lignan and oil components reduce mammary tumor growth at a late stage of carcinogenesis. Carcinogenesis 1996; 17(6): 1373-1376.
Tunon H. Phytotherapie in Schweden. Z Phytother 1999;20:268-77.
United States Congress (USC). Public Law 103-417: Dietary Supplement Health and Education Act of 1994. Washington, DC: 103rd Congress of the United States; 1994.
USC. See: United States Congress.
Walker B. Maternal diet and brain fatty acids in young rats. Lipids 1967;2:497-500.
Weiss R, Fintelmann V. Herbal Medicine. Stuttgart: Thieme; 2000.
Whitten C, Shultz T. |
| A rapid RP-HPLC method was developed to quantify the lignan SDG in baked goods containing flaxseed or flax meal. Finely ground materials were found to have a significantly greater content of SDG than course materials (Muir and Westcott, 2000).
Pharmacological Actions Crude Preparations
Laxative (Cunnane et al, 1995; Blumenthal et al, 1998). |
David Hoffman, FNIMH, AHG
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 Etoposide and teniposide are semisynthetic lignan derivatives of podophyllotoxin from the mayapples Podophyllum hexandrum and P. peltatum. Although not used clinically, podophyllotoxin is an antimitotic agent that binds to tubulin. Its derivatives, known as epipodophyllotoxins, do not affect microtubular assembly at pharmacological concentrations, but act as inhibitors of topoisomerase II, stabilizing DNA double-strand breaks. Cells are prevented from progressing beyond G2. Etoposide is used in the treatment of small-cell lung cancer and testicular cancer, and teniposide in pediatric cancers. |
Laurie Deutsch Mozian, M.S., R.D.
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| Use a high-lignan oil for extra lignan content. Spectrum Natural, Inc., is a reputable brand.
Taking flaxseed oil in capsules may be more palatable for some, but you pay a higher price for them. I compared the price of a bottle of Organic Flax Seed Oil that contains sixteen servings of one tablespoon each for $7.69 with General Nutrition Centers's (GNC's) store brand of flaxseed oil capsules—ninety in a bottle for $ 14.50. You would have to take fourteen capsules to get the amount of alpha-linoleic acid in one tablespoon of the liquid. The liquid flaxseed oil costs $. |
| Flaxseeds
Flaxseeds are tiny brown egg-shaped seeds that are silken to the touch and notable for two reasons; one is their lignan content. Lignans are phytochemicals that have the ability to mimic estrogen. Sometimes they are called phytoestrogens. The other notable feature of flaxseeds is their high content of the omega-3 fatty acids, which are also found in fish. Flaxseeds also contain flavonoids, coumaric acid, and phenolic phytochemicals.
The benefits of flaxseed can be made available upon grinding the flaxseed into meal or flour. |
David Hoffman, FNIMH, AHG
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| Adlercreutz H, et al. lignan and isoflavonoid conjugates in human urine. The Journal of Steroid Biochemistry and Molecular Biology 1995; 52(1):97-103.
83. Masquelier J, et al. Flavonoids and pycnogenols. International Journal for Vitamin and Nutrition Research 1979;49:307-11.
84. Haslam E, Lilley TH. Interactions of natural phenols with macromolecules. Progress in Clinical and Biological Research 1986; 213:53-65.
85. Chung KT, Wong TY, Wei CI, Huang YW, Lin Y. Tannins and human health: a review. Critical Reviews in Food Science and Nutrition 1998 Aug; 38(6):421-64.
86. |
| In addition, flaxseed oil contains secoisolariciresinol diglyco-side, a type of phytoestrogen known as a lignan, in varying amounts. Flaxseed oil may have anti-inflammatory, antithrombotic, and antiproliferative activities.9
Chaulmoogric acid
Chaulmoogric acid, or (5)-13-(cyclopent-2-enyl) tride-canoic acid, is present in amounts of about 27% as the glyceride ester in chaulmoogra oil, extracted from seeds of Hydnocarpus wightiana. The ethyl ester has been used in the treatment of leprosy.10
Fig. 5.3. |
Phyllis A. Balch, CNC
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 Phytochemicals include tocopherol, choline, betaine, lignan, and phenolic acids.
Walnuts
Shelled walnuts are delicious in baked goods, sprinkled on salads, and as a topping on desserts. The oil from walnuts is high in polyunsaturated fatty acids and tends to lower blood cholesterol. Walnut oil is used in cooking and is high in potassium, phosphorous, magnesium, and vitamin A. |
Judith Wills
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 Lignans are found in various plant foods, especially flax seeds, whole grains, and berries. The lignan enterolactone in this case appears to be the most potent form in helping to prevent breast cancer. The phytoestrogens may also be antioxidant.
Other phytochemicals that may help to fight hormone-related cancers are limonene, found in citrus oils, and certain members of the glucosinolate family (see above) found in sprouts, broccoli, etc. called indoles.
Other interesting phytochemicals
Bromelain, found in pineapples, aids digestion but may also clear blocked arteries and thin the blood. |
Dianne Onstad
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 Flax is a superior source of lignan, a mildly estrogenic compound that helps normalize a woman's menstrual cycle and that has anticancer, antibacterial, antifungal, and antiviral properties. Many women find that the use of flaxseed oil with a good balanced diet and other nutritional support has cleared up PMS symptoms as well as prevented stretch marks from developing after childbirth. Because it provides essential fatty acids as well as vitamin A, minetals, lecithin, and other vital nutrients, flaxseed oil helps to initiate cell renewal after a radiation burn. |
Gary Null, Ph.D.
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 Flaxseed and Its lignan and Oil Components Reduce Mammary Tumor Growth at a Late Stage of Carcinogenesis," Carcinogenesis, 17(6), June 1996, p. 1373-1376.
Results of this study indicated that supplemental flaxseed exhibited protective effects against colon cancer in rats fed a high-fat diet.
—M. Jenab & L.U. Thompson, "The Influence of Flaxseed and Lignans on Colon Carcinogenesis and Beta-glucuronidase Activity," Carcinogenesis, 17(6), June 1996, p. 1343-1348. |
Simon Mills and Kerry Bone
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| Selective antibiotic administration to humans suppressed oestrogenic lignan formation.288
Enterolactone, like isoflavones, inhibited oestradiol stimulated breast cancer cell growth in vitro.289 Increased lignan ingestion has been associated with increased concentrations of SHBG, but this was not confirmed in a clinical study.289 Linseed intake by normal premenopausal women was consistently associated with longer luteal phase (LP) lengths and higher ratios of LP progesterone to oestradiol.289 These findings may reflect favourably on breast cancer risk. |
Dr. Michael Heinrich, Joanne Barnes, Simon Gibbons and Elizabeth M. Williamson
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| By a serendipitous event, a crude fraction of podophyllin was treated with benzaldehyde, resulting in a mixture of products that were mainly benzyl derivatives of lignan glycosides (Stahelin & von Wartburg 1991). The crude reaction mixture was highly cytotoxic and active in the mouse life-prolongation assay against a leukaemia cell line. Some of the components of this mixture were isolated but were not as active as the whole mixture. Condensation of benzaldehyde with the reaction mixture generated a series of acetals that were not hydrolysed by glucosidase enzymes and were less water-soluble. |
| Chemists working at the Sandoz pharmaceutical company developed the hypothesis that podophyllin resin may contain anticancer lignan glycosides that are more water-soluble and less toxic than podophyllotoxin, and several of these natural products were isolated. The compounds did indeed possess greater water solubility but unfortunately less antitumour activity. Much work was done on these glycosides to make them resistant to enzymic hydrolysis, maintain their water solubility and improve their cellular uptake. |
Laurie Deutsch Mozian, M.S., R.D.
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| For menopausal or postmenopausal women who have low estrogen levels, the lignan will act like a source of estrogen, adding to the pool of circulating estrogenic substances, thereby working as an estrogen proxy.
Lignins (LIG-ninz). Lignins are structurally related to lignans, but they differ in their biological effects. Lignin is a type of insoluble dietary fiber that is found in the plant cell walls and can be resistant to breakdown by digestive enzymes.
Limonene (LlGH-mo-neen). Limonene, a monoterpene and phytochemical, is the simplest of the isoprenoids. |
Textbook of Natural Medicine 2nd Edition Volume 1Michael T. Murray, ND
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| Urinary isoflavonoid phytoestrogen and lignan excretion after consumption of fermented and unfermented soy products. J Am Diet Assoc 1995; 95: 545-551
10. Morton MS, Wilcox G, Wahlqvist ML, Griffiths K. Determination of lignans and isoflavonoids in human female plasma following dietary supplementation. J Endocrinol 1994; 142: 251-259
11. Fukutake M, Takahashi M, Ishida K et al. Quantification of genistein and genistin in soybeans and soybean products. Food Chem Toxicol 1996; 34: 457-461
12. Anthony MS, Clarkson TB, Hughes CL et al. |
volker schulz and Rudolf Hansel
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 Ro HS, Lee SY, Han BH (1977) Studies on the lignan glycoside of Acanthopanax cortex. J Pharm Korea 21: 81-86.
Schmidt CH (1977) Unspezifische Steigerung der Phagozytoseaktivitaten von Peritoneal-Makro-phagen nach oraler Gabe verschiedener Hefepraparationen. Dissertation, Freie Universitat Berlin.
Schmidt U, Albrecht M, Schenk N (1990) Pflanzliches Immunstimulans senkt Haufigkeit grippaler Infekte. Plazebo-kontrollierte Doppelblindstudie mit einem kombinierten Echinacea-Praparat mit 646 Studenten der Kolner Universitat. Natur- und Ganzheitsmedizin 3: 277-282. |
Josef A. Brinckmann and Michael P. Lindenmaier
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 Lignan lactones such as trache-logenin, arctigenin or nor-tracheloside contribute to the bitter taste of the drug [4]. Also present are small amounts of volatile ail (about 0.03%), which is composed of p-cymene, fenchone, citral and phenyl propa-tioids (e.g. cinnamic aldehyde) and benzoic icid, among others [5]; the main component is the polyine (= polyacetylene) dodeca-1,11-diene-3,5,7,9-tetraine. Other minor constituents such as pentacyclic triterpenes and flavonoids are unlikely to play a role in the drug's effectiveness. |
Textbook of Natural Medicine 2nd Edition Volume 1Michael T. Murray, ND
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| Adults
Plant lignan and isoflavonoid glycosides are converted by gut bacteria in the intestines to compounds with molecular weights and structures similar to steroid hormones (see Fig. 112.3). The pattern of isoflavonoid and lignan excretion in the urine is similar to endogenous estrogens.47 Studies of the effects of phytoestrogens on hormone levels are conflicting.
Lu et al48 found that the consumption of soy products by premenopausal women resulted in decreased circulating ovarian steroids and adrenal androgens, as well as increased length of the menstrual cycle. |
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