Plant Lignans and Health: Cancer Chemoprevention and Biotechnological Opportunities

Ford, Joshua D.; Davin, Laurence B.; Lewis, Norman

doi:10.1007/978-1-4615-4139-4_38

Cited by 17 publications

(11 citation statements)

References 78 publications

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“…Recent studies have shown that mammalian lignans produced in the colon may have anticancer properties 1–3. The lignans enterolactone and enterodiol, constitute the majority of the lignans in the human colon and derive from precursors provided through food consumption.…”

Section: Introductionmentioning

confidence: 99%

Effects of growing site and nitrogen fertilization on biomass production and lignan content of linseed (Linum usitatissimum L.)

2005

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There is strong evidence that the lignan precursors from vegetable material, secoisolariciresinol (seco) and matairesinol (mata), are major sources to support the development of lignans in the mammalian colon. Recent studies have shown these active agents to have anticancer properties, especially for mammary or prostatic carcinomas. Linseed is currently by far the best‐known source of seco and mata. To support the development of a food supplement, cultivars of linseed were tested at two sites and under increasing nitrogen supply to investigate how the lignan content is affected. The results indicated that the nitrogen supply did not affect the content of seco and mata at either site. A significant difference in seed yield could be measured between the sites, but the overall lignan content—even though significant—was less affected. The main effects were relatively similar at both sites and derived from the cultivars, indicating that the lignan content is very much dependent on genetic predisposition. Copyright © 2005 Society of Chemical Industry

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Section: Introductionmentioning

confidence: 99%

Effects of growing site and nitrogen fertilization on biomass production and lignan content of linseed (Linum usitatissimum L.)

2005

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“…SECO is the major lignan present in flaxseed, which is found as the conjugate diglycoside SDG (Ford and others 1999). Early studies have demonstrated that SDG is part of a larger complex (Bakke and Klosterman 1956).…”

Section: Introductionmentioning

confidence: 99%

“…The first mammalian lignans, END (MW = 302) and ENL ( MW = 298), were identified in humans and animals by Setchell and others (1980). Mammalian lignans are formed in the human body in the gastrointestinal (GI) tract, where GI bacteria hydrolyze the sugar moiety of SDG to release SECO (Muir and others 1996, 1997, 2000b; Ford and others 1999; Thompson, 1999). This is followed by dehydroxylation and demethylation by the colonic microflora to give the mammalian lignan END (Figure 4).…”

Section: Introductionmentioning

confidence: 99%

Flaxseed Lignans: Source, Biosynthesis, Metabolism, Antioxidant Activity, Bio‐Active Components, and Health Benefits

Touré

2010

Comp Rev Food Sci Food Safe

318

226

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Lignans are compounds found in a variety of plant materials including flaxseed, pumpkin seed, sesame seed, soybean, broccoli, and some berries. The major lignan in flaxseed is called secoisolariciresinol diglucoside (SDG). Once ingested, SDG is converted in the colon into active mammalian lignans, enterodiol, and entero-lactone, which have shown promise in reducing growth of cancerous tumors, especially hormone-sensitive ones such as those of the breast, endometrium, and prostate. Known for their hydrogen-donating antioxidant activity as well as their ability to complex divalent transition metal cations, lignans are propitious to human health. The extraction methods vary from simple to complex depending on extraction, separation, fractionation, identification, and detection of the analytes. Flax lignan is also a source of useful biologically active components found in plant foods, such as phytochemicals, and it is considered a functional food. The safety issues in flaxseed are also briefly discussed.

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“…However, in certain other plant species, such as flax (Linum usitatissimum), the opposite stereoselective and enantiospecific transformations can predominate (16,19,20,42), i.e. whereby (Ϫ)-pinoresinol (11b) is preferentially formed and then metabolized into (Ϫ)-lariciresinol (12b) and (ϩ)-secoisolariciresinol (2b), respectively.…”

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confidence: 99%

Crystal Structures of Apo-form and Binary/Ternary Complexes of Podophyllum Secoisolariciresinol Dehydrogenase, an Enzyme Involved in Formation of Health-protecting and Plant Defense Lignans

Youn

Moinuddin

Davin

et al. 2005

Journal of Biological Chemistry

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(؊)-Matairesinol is a central biosynthetic intermediate to numerous 8 -8-lignans, including the antiviral agent podophyllotoxin in Podophyllum species and its semi-synthetic anticancer derivatives teniposide, etoposide, and Etopophos®. It is formed by action of an enantiospecific secoisolariciresinol dehydrogenase, an NAD(H)-dependent oxidoreductase that catalyzes the conversion of (؊)-secoisolariciresinol. Matairesinol is also a plant-derived precursor of the cancerpreventative "mammalian" lignan or "phytoestrogen" enterolactone, formed in the gut following ingestion of high fiber dietary foodstuffs, for example. Additionally, secoisolariciresinol dehydrogenase is involved in pathways to important plant defense molecules, such as plicatic acid in the western red cedar (Thuja plicata) heartwood. To understand the molecular and enantiospecific basis of Podophyllum secoisolariciresinol dehydrogenase, crystal structures of the apo-form and binary/ternary complexes were determined at 1.6, 2.8, and 2.0 Å resolution, respectively. The enzyme is a homotetramer, consisting of an ␣/␤ single domain monomer containing seven parallel ␤-strands flanked by eight ␣-helices on both sides. Its overall monomeric structure is similar to that of NAD(H)-dependent shortchain dehydrogenases/reductases, with a conserved Asp 47 forming a hydrogen bond with both hydroxyl groups of the adenine ribose of NAD(H), and thus specificity toward NAD(H) instead of NADP(H). The highly conserved catalytic triad (Ser 153 , Tyr 167 , and Lys 171 ) is adjacent to both NAD ؉ and substrate molecules, where Tyr 167 functions as a general base. Following analysis of high resolution structures of the apo-form and two complex forms, the molecular basis for both the enantio-specificity and the reaction mechanism of secoisolariciresinol dehydrogenase is discussed and compared with that of pinoresinol-lariciresinol reductase.

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Plant Lignans and Health: Cancer Chemoprevention and Biotechnological Opportunities

Cited by 17 publications

References 78 publications

Effects of growing site and nitrogen fertilization on biomass production and lignan content of linseed (Linum usitatissimum L.)

Effects of growing site and nitrogen fertilization on biomass production and lignan content of linseed (Linum usitatissimum L.)

Flaxseed Lignans: Source, Biosynthesis, Metabolism, Antioxidant Activity, Bio‐Active Components, and Health Benefits

Crystal Structures of Apo-form and Binary/Ternary Complexes of Podophyllum Secoisolariciresinol Dehydrogenase, an Enzyme Involved in Formation of Health-protecting and Plant Defense Lignans

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