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Isolation of Naturally Occurring Novel Isoflavonoids Natural Product Reports c8np00069g We have presented the Graphical Abstract text and image for your article below. This brief summary of your work will appear in the contents pages of the issue in which your article appears. REVIEW 1 Isolation of naturally occurring novel isoflavonoids: an update Nawaf Al-Maharik* This review covers the literature concerning the isolation and identification of new naturally occurring isoflavonoids from Leguminosae and non-Leguminous species between 2012– 2017. Please check this proof carefully. Our staff will not read it in detail after you have returned it. Please send your corrections either as a copy of the proof PDF with electronic notes attached or as a list of corrections. Do not edit the text within the PDF or send a revised manuscript as we will not be able to apply your corrections. Corrections at this stage should be minor and not involve extensive changes. 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First (given) and Last (family) name(s) ResearcherID ORCID iD middle name(s) Nawaf Al-Maharik 0000-0002-7014-6190 REV C8NP00069G_GRABS Queries for the attention of the authors Journal: Natural Product Reports Paper: c8np00069g Title: Isolation of naturally occurring novel isoflavonoids: an update For your information: You can cite this article before you receive notification of the page numbers by using the following format: (authors), Nat. Prod. Rep., (year), DOI: 10.1039/c8np00069g. Editor's queries are marked on your proof like this 1, 2, etc. and for your convenience line numbers are indicated like this 5, 10, 15, . Please ensure that all queries are answered when returning your proof corrections so that publication of your article is not delayed. Query Query Remarks Reference Please confirm that the spelling and format of all author names is 1 correct. Names will be indexed and cited as shown on the proof, so these must be correct. No late corrections can be made. 2 Ref. 98: Please provide the last name for the 11th author. 3 Please check that ref. 159 has been displayed correctly. 4 Ref. 198: Please provide the initial(s) for the 1st author. REV C8NP00069G_GRABS Natural Product Reports REVIEW 1 Isolation of naturally occurring novel isoflavonoids: 1 an update† Cite this: DOI: 10.1039/c8np00069g 5 1 Nawaf Al-Maharik * 5 Covering: Jan. 2012 to Dec. 2017 10 10 This review describes the 391 new isoflavonoids isolated and identified from natural sources between Received 31st July 2018 January 2012 and December 2017, commenting on their sources, identification and biological activities. DOI: 10.1039/c8np00069g Due to the length of this review, the synthesis of isoflavonoids is not included. Furthermore, new rsc.li/npr applications of analytical techniques for the isolation and identification of isoflavonoids are also reviewed. 15 15 1. Introduction such as isoavans, isoavanones, isoavanols, isoav-3-enes, 2. Isolation and identication and more complex structures including pterocarpans, rote- 3. Isoavones noids, coumestans, arylcoumarins, coumaronochromones, 2- 3.1. Simple isoavones arylbenzofurans and isoavonoid dimers. Isoavonoids vary in 20 20 3.2. Isoavone glycosides several compounds by modication of their basic skeletons 3.3. Complex isoavones through further hydroxylation, methylation, prenylation, acyl- 4. Pterocarpans ation and glycosylation.1 In plants, isoavonoids occur as 5. Isoavanones aglycones or as glycosides (commonly with glucose, rhamnose 25 6. Iso avans, iso avanols and iso av-3-enes and apiose as the sugar constituent), where the iso avonoid 25 7. Rotenoids glycosides are less prevalent than aglycones. 8. Coumaronochromones Isoavonoids exhibit a wide range of biological activities 9. 3-Arylcoumarins including antioxidant, anticarcinogenic, and antiproliferative 10. Coumestans activities, reduction in osteoporosis and cardiovascular disease, 30 11. 2-Arylbenzofurans and is used the treatment of menopause symptoms.2–5 They are 30 12. Isoavonoid dimers, heterodimers and conjugates classically dened as dietary antioxidants, i.e. compounds that 13. Conclusions may protect against oxidative stress linked to inammation and 14. Species checklist the risk of macromolecule damage by free radicals and related 15. Conicts of interest oxygen and nitrogen-based oxidizing agents.2,3 In contrast to 35 16. Acknowledgements other groups of avonoids, the occurrence of isoavonoids in 35 17. References the plant kingdom is relatively sparse, possibly due to the sporadic incidence of isoavone synthase. The majority of natural isoavonoids (more than 1600 at the end of 2011) have 1. Introduction been reported from the subfamily Papilionoideae of the Legu- 40 40 minosae. However, isoavonoids have also been identied from Iso avonoids, which are plant secondary metabolites, are non-leguminous plants, including Iridaceae, Moraceae, Lil- characterized by a B-ring attached at the C-3 position of their C- iaceae, Compositae and Melicacea.5 Comprehensive reviews of ring (3-phenylchroman skeleton). This is biogenetically estab- advances on isoavonoid chemistry including their isolation, lished by the 2-hydroxyiso avanone synthase catalysed aryl modern isolation techniques, biosynthesis and synthesis have 45 1 45 migration of the 2-phenylchroman skeleton of avonoids. been periodically published.6–12 However, the current review is ff Iso avones are further transformed at di erent phases in plants concerned with the isolation of isoavonoids from Legumino- ff to yield een structurally di erent subclasses of iso avonoids, sae and non-leguminous sources, covering the literature pub- lished between January 2012 and December 2017 using the 50 Department of Forensic Sciences, Al Istilal University, Jericho, Palestinian Authority. SciFinder, Reaxys and PubMed (http://www.ncbi.nlm.nih.gov/ 50 E-mail: [email protected] entrez/query.fcgi) databases. † Electronic supplementary information (ESI) available. See DOI: 10.1039/c8np00069g This journal is © The Royal Society of Chemistry 2018 Nat. Prod. Rep.,2018,xx,1–40 | 1 Natural Product Reports Review genistein, irilone, and maackiain, with purity greater than 1 2.
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