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Occurrence of “mammalian” lignans in plant and water sources

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Abstract

Enterolignans, also called “mammalian” lignans because they are formed in the intestine of mammals after ingestion of plant lignans, were identified for the first time in extracts of four tree species, i.e., in knot heartwood of the hardwood species Fagus sylvatica and in knot or stem heartwood of the softwood species Araucaria angustifolia, Picea smithiana, and Abies cilicia. They were also identified for the first time in grain extracts of cultivated plants, i.e., in 15 cereal species, in 3 nut species, and in sesame and linseeds. Furthermore, some plant lignans and enterolignans were identified in extracts of water from different sources, i.e., in sewage treatment plant influent and effluent and in humic water, and for the first time also in tap and seawater. They were present also in water processed through a water purification system (ultrapure water). As enterolignans seem to be abundant in the aquatic environment, the occurrence of enterolignans in plant sources is most likely due to uptake by the roots from the surrounding water. This uptake was also shown experimentally by treating wheat (Triticum aestivum ssp. vulgare) seeds with purified lignan-free water spiked with enterolactone (EL) during germination and growth. Both the remaining seeds and seedlings contained high EL levels, especially the roots. They also contained metabolites of EL, i.e., 7-hydroxy-EL and 7-oxo-EL.

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Abbreviations

ASE:

Accelerated solvent extraction

CLar:

Cyclolariciresinol

DHEL:

4,4′-Dihydroxyenterolactone

ED:

Enterodiol

EL:

Enterolactone

GC-MS:

Gas chromatography-mass spectrometry

HEL:

7-Hydroxyenterolactone

HMR:

7-Hydroxymatairesinol

HPLC-MS/MS:

High-performance liquid chromatography-tandem mass spectrometry

Lar:

Lariciresinol

MDMR:

Monodemethylated matairesinol

MR:

Matairesinol

OEL:

7-Oxoenterolactone

RP:

Reversed-phase

Sec:

Secoisolariciresinol

STP:

Sewage treatment plant

TOC:

Total organic carbon

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Acknowledgments

Prof. Pedro Fardim at the Laboratory of Fibre and Cellulose Technology, Åbo Akademi University, Prof. Harzemşah Hafizoğlu at Bartin Faculty of Forestry, Zonguldak Karaelmas University, Turkey, and Prof. Mohammad Arfan at the Department of Chemistry, University of Peshawar, Peshawar, Pakistan are acknowledged for providing the tree samples. This work is part of the activities at the Åbo Akademi Process Chemistry Centre within the Finnish Centre of Excellence Programme by the Academy of Finland.

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Authors and Affiliations

  1. Department of Biochemistry and Pharmacy, Åbo Akademi University, BioCity, Artillerigatan 6 A, 20520, Turku, Finland

    Annika I. Smeds

  2. Process Chemistry Centre, Laboratory of Wood and Paper Chemistry, Åbo Akademi University, Porthansgatan 3, 20500, Turku, Finland

    Stefan M. Willför, Suvi P. Pietarinen & Markku H. T. Reunanen

  3. Plant Production Research, MTT Agrifood Research Finland, 31600, Jokioinen, Finland

    Pirjo Peltonen-Sainio

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  1. Annika I. Smeds
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  2. Stefan M. Willför
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  3. Suvi P. Pietarinen
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  4. Pirjo Peltonen-Sainio
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  5. Markku H. T. Reunanen
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Correspondence to Annika I. Smeds.

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Smeds, A.I., Willför, S.M., Pietarinen, S.P. et al. Occurrence of “mammalian” lignans in plant and water sources. Planta 226, 639–646 (2007). https://doi.org/10.1007/s00425-007-0512-4

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