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Wikipedia

Lignan

January 29, 2023

Not to be confused with Lignin.
For the wine and table grape, see Lignan (grape).

The lignans are a large group of low molecular weight polyphenols found in plants, particularly seeds, whole grains, and vegetables.[1] The name derives from the Latin word for "wood".[2] Lignans are precursors to phytoestrogens.[1][3] They may play a role as antifeedants in the defense of seeds and plants against herbivores.[4]

Biosynthesis and metabolism

Structures of some lignans

Lignans and lignin differ in their molecular weight, the former being small and soluble in water, the latter being high polymers that are undigestable. Both are polyphenolic substances derived by oxidative coupling of monolignols. Thus, most lignans feature a C18 cores, resulting from the dimerization of C9 precursors. The coupling of the lignols occurs at C8. Eight classes of lignans are: "furofuran, furan, dibenzylbutane, dibenzylbutyrolactone, aryltetralin, arylnaphthalene, dibenzocyclooctadiene, and dibenzylbutyrolactol."[5]

Many lignans are metabolized by mammalian gut microflora, producing so-called enterolignans.[6][7]

Food sources

Flax seeds and sesame seeds contain high levels of lignans.[1][8] The principal lignan precursor found in flaxseeds is secoisolariciresinol diglucoside.[1][8] Other foods containing lignans include cereals (rye, wheat, oat and barley), soybeans, tofu, cruciferous vegetables, such as broccoli and cabbage, and some fruits, particularly apricots and strawberries.[1] Lignans are not present in seed oil, and their contents in whole or ground seeds may vary according to geographic location, climate, and maturity of the seed crop, and the duration of seed storage.[1]

Secoisolariciresinol and matairesinol were the first plant lignans identified in foods.[1] Typically, lariciresinol and pinoresinol contribute about 75% to the total lignan intake, whereas secoisolariciresinol and matairesinol contribute only about 25%.[1]

Foods containing lignans:[1][9]

Source Lignan amount
Flaxseeds 85.5 mg per oz (28.35 g)
Sesame seeds 11.2 mg per oz
Brassica vegetables 0.3-0.8  mg per half cup (125 ml)
Strawberries 0.2 mg per half cup

Prevalence and Health Effects

Lignans are the principal source of dietary phytoestrogens in typical Western diets, even though most research on phytoestrogen-rich diets has focused on soy isoflavones. Lignan's enterolignan products enterodiol and enterolactone have weak estrogenic activity, but they may also exert biological effects through non-estrogenic means.[1]

A 2021 review found that lignans have a positive effect on lipid profiles of patients with dyslipidemia related diseases.[10] As of 2022 there is limited evidence that dietary intake of lignans is associated with a reduced cancer and cardiovascular disease risk.[1]

See also

References

  1. ^ a b c d e f g h i j k "Lignans". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2010. Retrieved 31 July 2017.
  2. ^ From lign- (Latin, "wood") + -an (chemical suffix).
  3. ^ Korkina, L; Kostyuk, V; De Luca, C; Pastore, S (2011). "Plant phenylpropanoids as emerging anti-inflammatory agents". Mini Reviews in Medicinal Chemistry. 11 (10): 823–35. doi:10.2174/138955711796575489. PMID 21762105.
  4. ^ Saleem, Muhammad; Kim, Hyoung Ja; Ali, Muhammad Shaiq; Lee, Yong Sup (2005). "An update on bioactive plant lignans". Natural Product Reports. 22 (6): 696–716. doi:10.1039/B514045P. PMID 16311631.
  5. ^ Umezawa, Toshiaki (2003). "Diversity in lignan biosynthesis". Phytochemistry Reviews. 2 (3): 371–90. doi:10.1023/B:PHYT.0000045487.02836.32. S2CID 6276953.
  6. ^ Adlercreutz, Herman (2007). "Lignans and Human Health". Critical Reviews in Clinical Laboratory Sciences. 44 (5–6): 483–525. doi:10.1080/10408360701612942. PMID 17943494. S2CID 31753060.
  7. ^ Heinonen, S; Nurmi, T; Liukkonen, K; Poutanen, K; Wähälä, K; Deyama, T; Nishibe, S; Adlercreutz, H (2001). "In vitro metabolism of plant lignans: New precursors of mammalian lignans enterolactone and enterodiol". Journal of Agricultural and Food Chemistry. 49 (7): 3178–86. doi:10.1021/jf010038a. PMID 11453749.
  8. ^ a b Landete, José (2012). "Plant and mammalian lignans: A review of source, intake, metabolism, intestinal bacteria and health". Food Research International. 46 (1): 410–24. doi:10.1016/j.foodres.2011.12.023.
  9. ^ Milder IE, Arts IC, van de Putte B, Venema DP, Hollman PC (2005). "Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol". British Journal of Nutrition. 93 (3): 393–402. doi:10.1079/BJN20051371. PMID 15877880.
  10. ^ Yang, C., Xia, H., Wan, M. (2021). "Comparisons of the effects of different flaxseed products consumption on lipid profiles, inflammatory cytokines and anthropometric indices in patients with dyslipidemia related diseases: systematic review and a dose–response meta-analysis of randomized controlled trials". Nutrition & Metabolism. 18 (1): 91. doi:10.1186/s12986-021-00619-3. PMC 8504108. PMID 34635132.{{cite journal}}: CS1 maint: multiple names: authors list (link)

External links

    January 29, 2023
    lignan, confused, with, lignin, wine, table, grape, grape, lignans, large, group, molecular, weight, polyphenols, found, plants, particularly, seeds, whole, grains, vegetables, name, derives, from, latin, word, wood, precursors, phytoestrogens, they, play, rol. Not to be confused with Lignin For the wine and table grape see Lignan grape The lignans are a large group of low molecular weight polyphenols found in plants particularly seeds whole grains and vegetables 1 The name derives from the Latin word for wood 2 Lignans are precursors to phytoestrogens 1 3 They may play a role as antifeedants in the defense of seeds and plants against herbivores 4 Contents 1 Biosynthesis and metabolism 2 Food sources 3 Prevalence and Health Effects 4 See also 5 References 6 External linksBiosynthesis and metabolism EditStructures of some lignans Matairesinol illustrating the debenzylbutyrolactone motif Secoisolariciresinol illustrating the 9 9 dihydroxydibenzylbutane motif Justicidin A illustrating the arylnaphthalene mofif Pinoresinol illustrating the furanofuran motif Steganacin illustrating the dibenzocyclooctadienelactone motif Podophyllotoxin illustrating the aryltetralin motif Lignans and lignin differ in their molecular weight the former being small and soluble in water the latter being high polymers that are undigestable Both are polyphenolic substances derived by oxidative coupling of monolignols Thus most lignans feature a C18 cores resulting from the dimerization of C9 precursors The coupling of the lignols occurs at C8 Eight classes of lignans are furofuran furan dibenzylbutane dibenzylbutyrolactone aryltetralin arylnaphthalene dibenzocyclooctadiene and dibenzylbutyrolactol 5 Many lignans are metabolized by mammalian gut microflora producing so called enterolignans 6 7 Food sources EditFlax seeds and sesame seeds contain high levels of lignans 1 8 The principal lignan precursor found in flaxseeds is secoisolariciresinol diglucoside 1 8 Other foods containing lignans include cereals rye wheat oat and barley soybeans tofu cruciferous vegetables such as broccoli and cabbage and some fruits particularly apricots and strawberries 1 Lignans are not present in seed oil and their contents in whole or ground seeds may vary according to geographic location climate and maturity of the seed crop and the duration of seed storage 1 Secoisolariciresinol and matairesinol were the first plant lignans identified in foods 1 Typically lariciresinol and pinoresinol contribute about 75 to the total lignan intake whereas secoisolariciresinol and matairesinol contribute only about 25 1 Foods containing lignans 1 9 Source Lignan amountFlaxseeds 85 5 mg per oz 28 35 g Sesame seeds 11 2 mg per ozBrassica vegetables 0 3 0 8 mg per half cup 125 ml Strawberries 0 2 mg per half cupPrevalence and Health Effects EditLignans are the principal source of dietary phytoestrogens in typical Western diets even though most research on phytoestrogen rich diets has focused on soy isoflavones Lignan s enterolignan products enterodiol and enterolactone have weak estrogenic activity but they may also exert biological effects through non estrogenic means 1 A 2021 review found that lignans have a positive effect on lipid profiles of patients with dyslipidemia related diseases 10 As of 2022 there is limited evidence that dietary intake of lignans is associated with a reduced cancer and cardiovascular disease risk 1 See also EditHerbalism Pharmacognosy FlavonolignanReferences Edit a b c d e f g h i j k Lignans Micronutrient Information Center Linus Pauling Institute Oregon State University 2010 Retrieved 31 July 2017 From lign Latin wood an chemical suffix Korkina L Kostyuk V De Luca C Pastore S 2011 Plant phenylpropanoids as emerging anti inflammatory agents Mini Reviews in Medicinal Chemistry 11 10 823 35 doi 10 2174 138955711796575489 PMID 21762105 Saleem Muhammad Kim Hyoung Ja Ali Muhammad Shaiq Lee Yong Sup 2005 An update on bioactive plant lignans Natural Product Reports 22 6 696 716 doi 10 1039 B514045P PMID 16311631 Umezawa Toshiaki 2003 Diversity in lignan biosynthesis Phytochemistry Reviews 2 3 371 90 doi 10 1023 B PHYT 0000045487 02836 32 S2CID 6276953 Adlercreutz Herman 2007 Lignans and Human Health Critical Reviews in Clinical Laboratory Sciences 44 5 6 483 525 doi 10 1080 10408360701612942 PMID 17943494 S2CID 31753060 Heinonen S Nurmi T Liukkonen K Poutanen K Wahala K Deyama T Nishibe S Adlercreutz H 2001 In vitro metabolism of plant lignans New precursors of mammalian lignans enterolactone and enterodiol Journal of Agricultural and Food Chemistry 49 7 3178 86 doi 10 1021 jf010038a PMID 11453749 a b Landete Jose 2012 Plant and mammalian lignans A review of source intake metabolism intestinal bacteria and health Food Research International 46 1 410 24 doi 10 1016 j foodres 2011 12 023 Milder IE Arts IC van de Putte B Venema DP Hollman PC 2005 Lignan contents of Dutch plant foods a database including lariciresinol pinoresinol secoisolariciresinol and matairesinol British Journal of Nutrition 93 3 393 402 doi 10 1079 BJN20051371 PMID 15877880 Yang C Xia H Wan M 2021 Comparisons of the effects of different flaxseed products consumption on lipid profiles inflammatory cytokines and anthropometric indices in patients with dyslipidemia related diseases systematic review and a dose response meta analysis of randomized controlled trials Nutrition amp Metabolism 18 1 91 doi 10 1186 s12986 021 00619 3 PMC 8504108 PMID 34635132 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link External links EditIUPAC lignan nomenclature Retrieved from https en wikipedia org w index php title Lignan amp oldid 1131231964, wikipedia, wiki, book, books, library,

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