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Isoflavonoids in Non-Leguminous Families: an Update

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Isoflavonoids in Non-Leguminous Families: an Update REVIEW Isoflavonoids in non-leguminous families: an update www.rsc.org/npr NPR Joel¨ Reynaud,* David Guilet, Raphael Terreux, Monique Lussignol and Nadia Walchshofer Universite´ Claude Bernard Lyon 1, ISPB Faculte´ de Pharmacie, 8 avenue Rockefeller, 69373 Lyon Cedex 08, France. E-mail: [email protected] Received (in Cambridge, UK) 3rd June 2005 First published as an Advance Article on the web 30th June 2005 Covering: the literature from the first reported isolation of isoflavonoids from non-leguminous families up to April 2005 This review provides a listing of isoflavonoids reported in non-leguminous families. Reviews published to date have principally focused on plants with the richest isoflavonoid contents, the family Leguminosae.Afterabriefrecallofthe structure of isoflavonoids, we present all isoflavonoid structures encountered in non-leguminous families which may, thereby, become new plant sources for these compounds. Articles reporting on their different functions in plants are pre- sented, as well as a brief summary discussing their potential benefits for human health. A list of 135 references is given. 1 Introduction properties have been reported in humans, their interest as phy- toestrogens has grown considerably among human pathologists. Over the past two decades, few plant secondary metabolism The presence of isoflavonoids is almost entirely restricted to products have received as much attention from biochemists, the subfamily Fabaceae, of the family Leguminosae,butthey plant pathologists, medical researchers, and dieticians as are also occasionally found in some other angiosperm families. isoflavonoids. Numerous papers have described the occurrence of isoflavonoids At the beginning of plant chemistry, isoflavonoids were in the leguminous family. No review, to our knowledge, has studied by phytochemists only and considered useful chemosys- specifically addressed the global distribution of isoflavonoids in tematic markers.1 Later on, as they became known for their families other than the Leguminosae, apart from two studies antifungal and insecticidal properties, they were considered on Rutaceae2 and Mysticaceae,3 the chapter on isoflavonoids as phytoalexins by phytophysiologists. Since their estrogen-like written by Dewick in the 1994 edition of “The Flavonoids”4 Joel¨ Reynaud, PhD, Maˆıtre de Conferences´ (Assistant Professor), teaches botany to pharmacy students. His research interest is phytochemistry, and more precisely the study of flavonoids. He has been particularly involved in the study of flavonoids used as evolution indicators in the complex Lotus corniculatus (Fabaceae). His current research interests include the extraction and purification of natural plant products (flavonoids s. l.) with potential therapeutic properties. David Guilet received his PhD from the University of Angers (France) where he studied natural compounds from Clusiaceae species under the supervision of Professor Pascal Richomme. He undertook a 2-year postdoctoral research position in Kurt Hosttetmann’s laboratory at the University of Lausanne (Switzerland). He is currently Maˆıtre de Conferences´ (Assistant Professor) at the Faculty of Pharmacy of Lyon University and teaches pharmacognosy. His research interests revolve around natural products: isolation, structure elucidation and bioactive potentialities. Raphael Terreux, PhD, Maˆıtre de Conferences´ (Assistant Professor) and specialist in molecular modelling and Quantitative Structure– Activity Relationships (QSAR), teaches physical chemistry. He undertook his PhD at the University of Nice-Sophia Antipolis (France), with a dissertation on drugs against the TAR RNA element of the HIV1 genome. He took a postdoctoral position at the Steacie Institute of The National Research Council of Canada (NRC), where he designed drugs from natural products for cancer therapy. Monique Lussignol, Research Engineer, studies natural plant products: her current research interests revolve around flavonoids and saponins. She is also involved in the laboratory training of students preparing for research in plant chemistry. Nadia Walchshofer obtained her PhD from Universite´ Claude Bernard-Lyon 1, where her work focused on the synthesis of heterocyclic compounds active against parasite organisms. She began her academic career at the faculty of Pharmacy of Lyon as an Assistant Professor of Medicinal Chemistry in 1984, then she was promoted to Professor of Organic Chemistry in 1998. Her research interests include medicinal chemistry, strategies for the synthesis of biologically active molecules, and the development of new synthetic methods. :10.1039/b416248j Joel¨ Reynaud David Guilet Raphael Terreux Monique Lussignol Nadia Walchshofer DOI 504 Nat. Prod. Rep., 2005, 22, 504–515 This journal is © The Royal Society of Chemistry 2005 and a general review on isoflavonoids by Tahara and Ibrahim in rotenoids, and 100% of isoflavans, isoflavanones, coumestans 1995.5 and pterocarpans.20 They were, then, widely used as taxonomic The purpose of this report is to update the non-leguminous markers within this family. In 1995, Tahara and Ibrahim sources of isoflavonoids. To that end, the isoflavonoids present reported that some of these molecules had also been identified in non-leguminous families reported in the literature are listed: in 23 other angiosperm families.5 either by Wong (1975)6 or Dewick (1982, 1988, 1994),4,7,8 in According to Dewick, 465 structures were known in 1982, 630 the different issues of Harborne’s book “The Flavonoids” in 1988 and 870 in 1993.4 Of note, only 26 isoflavonoid aglycones (edn. 1975, 1982, 1988, 1994),9–12 or by other authors,13,14 as were reported in the book by Geissman in 1962.21 well as in “The Handbook of Natural Flavonoids” (1999) Many new isoflavonoid structures have been identified since published by Harborne and Baxter.15 Secondly, for studies the late nineties; their total number now exceeds a thousand. subsequent to the completion of these books, we have re- Several additional families, outside the Leguminosae, have also viewed scientific databases such as SciFinder and PubMed been shown to synthesise these molecules. More than thirty (www.ncbi.nlm.nih.gov/entrez/query.fcgi). We were able to families of flowering plants are known to produce isoflavonoids inventory over 160 types of isoflavonoids reported in 31 non- (mainly isoflavones). Yet, the family Leguminosae remains the leguminous families. most important family of plants involved in the synthesis of isoflavonoids (several hundreds of species for over a thousand 2 Chemistry of isoflavonoids different structures), all the more so as plants from other families often produce only 2 or 3 different molecules, or even only one 2.1. Classification in some cases. Isoflavonoids (over 1000 structures) are a large subclass of Nine isoflavonoid subclasses have been mentioned in non- flavonoids (approximately 5000 structures) with a 15-carbon leguminous families (Table 1). As in the Leguminosae, the largest (C6–C3–C6) backbone arranged as a 1,2-diphenylpropane group consists of isoflavones. skeleton. In plants, isoflavonoids may be encountered as aglycones or as glycosides (with generally glucose, rhamnose or apiose as the 3.1. Isoflavonoids in monocots sugar component), but glycosidic derivatives are less common In monocots, few families (only 6 have been reported) seem than the free state. The number of isoflavonoid glycosides is thus able to produce isoflavonoids. The Iridaceae are the major extremely small compared with the very vast range of flavone and source of isoflavonoids in this group, with more than 50 flavonol glycosides. This paper will only report on the aglycone different compounds described (Table 3), mainly in the genus skeletons, even if the compounds have been found as glycosides Iris where they are present in the rhizomes of approximately in the plants. 20 species. As in the Leguminosae, it has been demonstrated The number and complexity of possible substituents on the that Iridaceae treated with cupric chloride are able to produce basic structural skeleton (methoxyl, aromatic or aliphatic acids, coumaronochromones in the leaves.95,96 prenyl, methylenedioxy or isoprenyl...), the different oxidation A study of green barley (Hordeum vulgare) published in 1992 levels and the frequent presence of extra heterocyclic rings mentioned the presence of a major “isoflavonoid” antioxidant account for the multiplicity of subgroups among isoflavonoids. identified as 2-O-glucosylisovitexin97 in the leaves of the plant. Some isoflavonoids are amino-substituted; these are called “isoflavonoid alkaloids”,16 whereas others may be chlorinated.17 The presence of C-glycosylisoflavonoids has been reported in the Leguminosae12 and in the Menispermaceae.18 Isoflavonoids may also be found as dimers.19 2.2. Isolation and identification Techniques for the isolation and identification of isoflavonoids were previously described14 and will not be discussed in this report. Of note, however, the combination of high-performance liquid chromatography (HPLC) with mass spectrometry (MS) has proved to be a useful tool, particularly when associated with atmospheric pressure chemical ionization (APCI). The use of capillary electrophoresis (CE) is also common, in particular Despite the use of the prefix “iso”, this compound is not in combination with electrospray ionization mass spectrom- an isoflavonoid but a C-glucosylflavone. Unfortunately, the etry (ESI-MS). Two-dimensional nuclear magnetic resonance error that had been made in the title has been duplicated on (NMR) is frequently
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