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. 2019 Jan 9;24(2):220.
doi: 10.3390/molecules24020220.

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

Patrik Eklund  1 , Jan-Erik Raitanen  2
Affiliations

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

Patrik Eklund et al. Molecules. .

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.

Keywords: 9-norlignans; bioactivity; hydroxymatairesinol; lignans; norlignans; semisynthesis.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
Fundamental structures for the lignan and different 9-norlignan and 9-norneolignan structures. Dotted (red lines) lines indicate the missing carbon-9 atom.
Figure 2
Figure 2
The structures of previously reported 9-norlignans with natural origin.
Figure 3
Figure 3
Structures of synthetic 9-norlignans and 9-norlignan related compounds.
Scheme 1
Scheme 1
Preparation of various 9-norlignans from hydroxymatairesinol. This generalized scheme shows the fundamental chemical transformations. For more detailed information on the interconversions and transformations including reaction conditions, see the supplementary material.
See this image and copyright information in PMC

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