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. 2021 Sep 26;26(19):5838.
doi: 10.3390/molecules26195838.

Convenient Preparation and Spectroscopic Characterization of 7 R-Hydroxymatairesinol

Eleonora Colombo  1 , Giuseppe Paladino  2 , Umberto Ciriello  2 , Daniele Passarella  1
Affiliations

Convenient Preparation and Spectroscopic Characterization of 7 R-Hydroxymatairesinol

Eleonora Colombo et al. Molecules. .

Abstract

The preparation of 7R-HMR (allo-hydroxymatairesinol) is reported by: (a) NaBH4 kinetic reduction of 7R/7S diastereomeric mixture; and (b) epimerization of the C7 hydroxyl group by Mitsunobu reaction and subsequent ester hydrolysis. The availability of highly pure target compound (7R-HMR) made it possible to confirm the structure of the target compound and to complete the full spectroscopic characterization.

Keywords: 7-hydroxymatairesinol (HMR); Picea abies; allo-hydroxymatairesinol; lignans.

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Conflict of interest statement

The authors declare no conflict of interest. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript, or in the decision to publish the results.

Figures

Scheme 1
Scheme 1
Enrichment of 7R-HMR by hydride reduction.
Figure 1
Figure 1
HPLC chromatogram relative to the reaction after 3.5 h.
Scheme 2
Scheme 2
Conversion of 7S-HMR into 7R-HMR by Mitsunobu strategy.
Scheme 3
Scheme 3
Synthetic strategy for preparation of 7R-HMR.
Figure 2
Figure 2
Most relevant COSY and HMBC interactions for 7R-HMR structure elucidation.
See this image and copyright information in PMC

References

    1. Saleem M., Hyoung J.K., Ali M.S., Yong S.L. An update on bioactive plant lignans. Nat. Prod. Rep. 2005;25:696–716. doi: 10.1039/b514045p. - DOI - PubMed
    1. Smeds A.I., Eklund P.C., Sjöholm R.E., Willför S.M., Nishibe S., Deyama T., Holmbom B.R. Quantification of a broad spectrum of lignans in cereals, oilseeds, and nuts. J. Agric. Food Chem. 2007;55:1337–1346. doi: 10.1021/jf0629134. - DOI - PubMed
    1. Eklund P.C., Sundell F.J., Smeds A.I., Sjöholm R.E. Reactions of the natural lignan hydroxymatairesinol in basic and acidic nucleophilic media: Formation and reactivity of a quinone methide intermediate. Org. Biomol. Chem. 2004;2:2229–2235. doi: 10.1039/B402849J. - DOI - PubMed
    1. Willför S., Hemming J., Reunanen M., Eckerman C., Holmbom B. lignans and lipophilic extractives in norway spruce knots and stemwood. Holzforschung. 2003;57:27–36. doi: 10.1515/HF.2003.005. - DOI
    1. Spilioti E., Holmbom B., Papavassiliou A.G., Moutsatsou P. Lignans 7-Hydroxymatairesinol and 7-Hydroxymatairesinol 2 exhibit anti-inflammatory activity in human aortic endothelial cells. Mol. Nutr. Food. Res. 2014;58:749–759. doi: 10.1002/mnfr.201300318. - DOI - PubMed