Neolignans
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Lignans and neolignans are plant secondary metabolites derived from the oxidative coupling of phenylpropanoids. Biological activity of these phenolic compounds ranges from antioxidant, antitumor (terminaloside P, IC50 = 10 nM), anti-inflammatory, anti-neurodegenerative (schibitubin B, IC50 = 3.2 nM) and antiviral (patentiflorin A, IC50 = 14-23 nM) to antimicrobial. In addition, it was observed that several members of this group, namely enterolactone and its biochemical precursors also known as phytoestrogens, possess important protective properties. Most of these lignans and neolignans are presented in reasonable amounts in one's diet and thus the protection they provide against the colon and breast cancer, to name a few, is even more important to note. Similarly, neuroprotective properties were observed (schisanwilsonin G, IC50 = 3.2 nM) These structural motives also serve as an important starting point in the development of anticancer drugs. Presumably the most famous members of this family, etoposide and teniposide, synthetic derivatives of podophyllotoxin, are used in the clinical treatment of lymphocytic leukemia, certain brain tumors, and lung tumors already for nearly 20 years. This review describes 413 lignans and neolignans which have been isolated between 2016 and mid-2018 being reported in more than 300 peer-reviewed articles. It covers their source, structure elucidation, and bioactivity. Within the review, the structure-based overview of compounds as well as the bioactivity-based overview of compounds are described.
- MeSH
- lidé MeSH
- lignany chemie farmakologie MeSH
- rostliny metabolismus MeSH
- sekundární metabolismus MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- přehledy MeSH
Secondary metabolites (SM) from organisms have served medicinal chemists over the past two centuries as an almost inexhaustible pool of new drugs, drug-like skeletons, and chemical probes that have been used in the "hunt" for new biologically active molecules with a "beneficial effect on human mind and body." Several secondary metabolites, or their derivatives, have been found to be the answer in the quest to search for new approaches to treat or even eradicate many types of diseases that oppress humanity. A special place among SM is occupied by lignans and neolignans. These phenolic compounds are generated biosynthetically via radical coupling of two phenylpropanoid monomers, and are known for their multitarget activity and low toxicity. The disadvantage of the relatively low specificity of phenylpropanoid-based SM turns into an advantage when structural modifications of these skeletons are made. Indeed, phenylpropanoid-based SM previously have proven to offer great potential as a starting point in drug development. Compounds such as Warfarin® (a coumarin-based anticoagulant) as well as etoposide and teniposide (podophyllotoxin-based anticancer drugs) are just a few examples. At the beginning of the third decade of the twenty-first century, the call for the treatment of more than a dozen rare or previously "neglected" diseases remains for various reasons unanswered. Leishmaniasis, a neglected disease that desperately needs new ways of treatment, is just one of these. This disease is caused by more than 20 leishmanial parasites that are pathogenic to humans and are spread by as many as 800 sandfly species across subtropical areas of the world. With continuing climate changes, the presence of Leishmania parasites and therefore leishmaniasis, the disease caused by these parasites, is spreading from previous locations to new areas. Thus, leishmaniasis is affecting each year a larger proportion of the world's population. The choice of appropriate leishmaniasis treatment depends on the severity of the disease and its form of manifestation. The success of current drug therapy is often limited, due in most cases to requiring long hospitalization periods (weeks to months) and the toxicity (side effects) of administered drugs, in addition to the increasing resistance of the parasites to treatment. It is thus important to develop new drugs and treatments that are less toxic, can overcome drug resistance, and require shorter periods of treatment. These aspects are especially important for the populations of developing countries. It was reported that several phenylpropanoid-based secondary metabolites manifest interesting antileishmanial activities and are used by various indigenous people to treat leishmaniasis. In this chapter, the authors shed some light on the various biological activities of phenylpropanoid natural products, with the main focus being on their possible applications in the context of antileishmanial treatment.
Bailliere's clinical endocrinology and metabolism, ISSN 0950-351X Vol. 12, No. 4
IX, 543-748 s. : il. ; 24 cm
Plant lignans possess several properties beneficial for human health and therefore, increasing their contents in foods and beverages is desirable. One of the lignan sources in human diet is wine. To elucidate the origin of lignans contained in wine, LC-MS was used to analyze resinol-related lignans in must, seeds, stems, and wine prepared using stainless steel tanks, oak barrels, and Qvevri (clay vessel). White wines aged in stainless steel tanks contained significantly lower amounts of lignan aglycones (20-60 µg/L) than red and Qvevri wines (300-500 µg/L). Generally, white wines aged in stainless steel tanks contained only low amounts of isolariciresinol and matairesinol. Qvevri wines and red wine aged in stainless steel tank contained up to five lignan compounds and in wine aged in oak barrel, six different lignans were identified. Consistently, only low concentration of isolariciresinol has been found in must, whereas more lignan compounds have been found in grape seeds (isolariciresinol, secoisolariciresinol, and pinoresinol) and stems (isolariciresinol and syringaresinol). Consequently, we conclude that lignan content in wine can be increased by maturation in contact with grape berries, seeds, or stems or with wood.
