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Flaxseed, a Functional Food—Constituents and Their Health Benefits
Published in Robert Fried, Richard M. Carlton, Flaxseed, 2023
Robert Fried, Richard M. Carlton
Plant lignans are phenolic compounds present in almost all plants. They act as both antioxidants and phytoestrogens. Phytoestrogens can have weak estrogen activity in animals and humans. Flax contains up to 800 times more lignans than other plant foods (and their content in flaxseed is principally composed of secoisolariciresinol diglucoside (SDG) (294–700 mg/100 gram), matairesinol (0.55 mg/100 gram), lariciresinol (3.04 mg/100 gram) and pinoresinol (3.32 mg/100 g).
Recent In-Depth Insights of Nature-Based Anti-Worm Therapeutic Medications: Emerging Herbal Anthelmintics
Published in Debarshi Kar Mahapatra, Cristóbal Noé Aguilar, A. K. Haghi, Applied Pharmaceutical Practice and Nutraceuticals, 2021
Ankita Soni, Paras Kothari, Debarshi Kar Mahapatra
The leaves are rich in essential oil and mineral matters, particularly in potash salts. Albuminoids, vitamin C, and nitrogen are also present. The composition includes 89.6 protein, 3.7 fat, 0.4 fiber, 0.8 carbohydrates, 2.9 minerals, 2.6 calcium, 150 phosphorous, 80 iron, 4.2 thiamine, 0.01 riboflavin, 0.14 niacin, 0.6 vitamin C, 24.0 zinc, 0.98 iodine, 6.3 fluorine, and 250 ppm vitamin K. Betalain alkaloids, phenolic acids are present in fruits, betain, and oxalic acid are found in leaves, furanocoumarins and saponins are situated in the seeds, and oleanolic acid and sitosterol are found in flowers.17–18 The hydrodistillation of leaves yield 0.64% v/w essential oil with abundant constituents such as p-cymene (40.9%), ascari-dole (15.5%), pinane-2-ol (9.9%), α-pinene (7.0%), β-pinene (6.2%), and α-terpinol (6.2%).19 A new phenolic glycoside, chenoalbuside has been isolated from the methanol extract of the seeds.20 The hydroalcoholic extract of the leaves led to the isolation of seven imperative lignans (pinoresinol, syringaresinol, lariciresinol with its derivative compound and three sesquilignans).21 Kaempferol, quercetin, and their glycosides have been isolated from the aerial parts.22
Chemopreventive Agents
Published in David E. Thurston, Ilona Pysz, Chemistry and Pharmacology of Anticancer Drugs, 2021
Enterolactone (Figure 12.18) is a mammalian lignan formed by the action of intestinal bacteria on plant lignan precursors in the diet. Many dietary plant lignans, such as seco-isolariciresinol, matairesinol, lariciresinol, pinoresinol, and sesamin, can be metabolized by gut microbes to enterolactone. The richest dietary sources of enterolactone precursors are flaxseed, sesame seeds, and cereals. Since enterolactone is produced by specific species of gut microbiota, it is interesting that the capacity to produce it varies between individuals. Also, the capacity to produce enterolactone in the gut can be significantly reduced by antibiotic treatments, a situation that can take many months to recover from.
The old world salsola as a source of valuable secondary metabolites endowed with diverse pharmacological activities: a review
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2022
Mai H. ElNaggar, Wagdy M. Eldehna, Mohammed A. S. Abourehab, Fatma M. Abdel Bar
Lignans are natural secondary metabolites biosynthesized from the oxidative coupling of two p-hydroxyphenylpropane moieties (C6-C3) linked by a bond connecting the middle (β-β`) carbons of their side chains98. Regarding the genus Salsola, six derivatives from two major subclasses, lignans and cylolignans, were identified. For the lignans subclass, three tetrahydrofuran derivatives, alangilignoside C 6.2, conicaoside 6.3, and lariciresinol-9-O-β-D-glucopyranoside 6.5 were isolated from the aerial parts of S. komarovii89. Regarding the cylolignans subclass, two tetrahydronaphthalene derivatives, namely (8S,8`R,7`R)-9′-[(β-glucopyranosyl)oxy]lyoniresinol 6.4 and (+)-lyoniresinol 9′-O-β-D-glucopyranoside 6.6, were isolated from the same plant89, Table 2 and Figure 7. In addition, another bicyclolignan derivative having a 3,7-dioxabicyclo[3.3.0]octane ring system, namely acanthoside D 6.1 was isolated from S. collina plant60.
Biogenic zinc oxide nanoparticles-enhanced biosynthesis of lignans and neolignans in cell suspension cultures of Linum usitatissimum L
Published in Artificial Cells, Nanomedicine, and Biotechnology, 2019
Bilal Haider Abbasi, Adnan Zahir, Waqar Ahmad, Muhammad Nadeem, Nathalie Giglioli-Guivarc’h, Christophe Hano
Linum usitatissimum, a novel plant belonging to the family linaceae has a rich history regarding industrial applications—linen fiber production and linseed oil extraction—however, currently it is increasingly exploited as a great source of some health-promoting phenolic metabolites known as lignans and neolignans [1]. These metabolites are naturally occurring polyphenols, which have potential therapeutic applications mainly against different types of cancer, some microbial infections and inflammation as well. Major lignans are secoisolariciresinol diglucoside (SDG) and lariciresinol diglucoside (LDG), whereas dehydrodiconiferyl alcohol glucoside (DCG) and guaiacylglycerol-β-coniferyl alcohol ether glucoside (GGCG) are well-known neolignans [2]. Both lignans and neolignans share similar structural conformation, but they can be easily characterized by difference in (a minor but significant) bonding pattern. Generally, lignans consist of phenylpropane dimers that are bonded through the carbon atoms (C8/C8∼) of their side chains, whereas in neolignans, these dimers are connected through bond other than C8/C8∼ [3].
Association between dietary phytoestrogens intakes and prostate cancer risk in Sicily
Published in The Aging Male, 2018
Giorgio I. Russo, Marina Di Mauro, Federica Regis, Giulio Reale, Daniele Campisi, Marina Marranzano, Arturo Lo Giudice, Tatiana Solinas, Massimo Madonia, Sebastiano Cimino, Giuseppe Morgia
Multivariate logistic regression adjusted for age, energy intake, weight status, smoking status, alcohol consumption, physical activity level and family history of prostatic cancer showed that lignans (Q[quartile]4 vs. Q1, OR[odds ratio] = 4.72 [95% CI: 2.34–9.52]) and specifically, lariciresinol (Q4 vs. Q1, OR = 4.60 [95% CI: 2.32–9.11]), pinoresinol (Q4 vs. Q1, OR = 5.62 [95% CI: 2.70–11.70]), matairesinol (Q4 vs. Q1, OR = 3.63 [95% CI: 1.86–7.10]) and secoisolariciresinol (Q4 vs. Q1, OR = 4.10 [95% CI: 2.10–8.10]) were associated with increased risk of PCa (Table 3). Furthermore, we found that isoflavones (Q3 vs. Q1, OR = 0.28 [95% CI: 0.10–0.77]) and specifically, genistein (Q4 vs. Q1, OR = 0.40 [95% CI: 0.21–0.77]) were associated with reduced risk of PCa. We found no other significant association between different phytoestrogen and advanced PCa risk (Table 4).