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Molecules 2019, 24(2), 220; https://doi.org/10.3390/molecules24020220

9-Norlignans: Occurrence, Properties and Their Semisynthetic Preparation from Hydroxymatairesinol

Johan Gadolin Process Chemistry Centre, Laboratory of Organic Chemistry, Åbo Akademi University, Piispankatu 8, FIN-20500 Turku, Finland
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Received: 8 November 2018 / Revised: 27 December 2018 / Accepted: 28 December 2018 / Published: 9 January 2019
(This article belongs to the Special Issue Lignans)
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Abstract

Lignans, neolignans, norlignans and norneolignans constitute a large class of phenolic natural compounds. 9-Norlignans, here defined to contain a β–β’ bond between the two phenylpropanoid units and to lack carbon number 9 from the parent lignan structure, are the most rarely occurring compounds within this class of natural compounds. We present here an overview of the structure, occurrence and biological activity of thirty-five 9-norlignans reported in the literature to date. In addition, we report the semisynthetic preparation of sixteen 9-norlignans using the natural lignan hydroxymatairesinol obtained from spruce knots, as starting material. 9-Norlignans are shown to exist in different species and to have various biological activities, and they may therefore serve as lead compounds for example for the development of anticancer agents. Hydroxymatairesinol is shown to be a readily available starting material for the preparation of norlignans of the imperanene, vitrofolal and noralashinol family. View Full-Text
Keywords: lignans; norlignans; 9-norlignans; semisynthesis; hydroxymatairesinol; bioactivity lignans; norlignans; 9-norlignans; semisynthesis; hydroxymatairesinol; bioactivity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Eklund, P.; Raitanen, J.-E. 9-Norlignans: Occurrence, Properties and Their Semisynthetic Preparation from Hydroxymatairesinol. Molecules 2019, 24, 220.

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