Details

Autor(en) / Beteiligte

• Schmidt, Thomas J.
• Klaes, Michael
• Sendker, Jandirk

Titel

Lignans in seeds of Linum species

Ist Teil von

• Phytochemistry (Oxford), 2012-10, Vol.82, p.89-99

Ort / Verlag

England: Elsevier Ltd

Erscheinungsjahr

2012

Quelle

Elsevier ScienceDirect Journals

Beschreibungen/Notizen

• The lignan profiles of seeds of 23 Linum taxa as determined by HPLC/ESI-MSMS are described and compared. Two major groups of species exist that accumulate cyclolignans mainly of the aryltetralin- and arylnaphthalene/dihydronaphthalene types, respectively. The latter also contain 8R,8′R-secoisolariciresinol diglucoside whereas the former were neither found to accumulate this lignan nor its 8S,8′S-stereoisomer. The occurrence of this latter lignan is restricted to L. usitatissimum and some of its close relatives, which, on the other hand, do not accumulate significant amounts of non-polar cyclolignans. This distribution of lignans correlates strongly with the molecular phylogeny of the genus Linum. Chemosystematic and biosynthetic aspects are discussed. [Display omitted] ► Seeds of 23 Linum taxa were analyzed for non-polar as well as polar lignans by HPLC/ESI-MSMS. ► The overall distribution of 23 lignans (some aryltetralin esters) correlates with phylogeny. ► 8R,8′R-SDG co-occurs with arylnaphthalene-/dihydronaphthalene cyclolignans. ► 8S,8′S-SDG is restricted to the L. usitatissimum group (insignificant amounts of cyclolignans). ► Seeds of taxa accumulating aryltetralin lignans do not contain SDG in either form. Mature seeds of 20 Linum species were analyzed for their content of lignans. The seeds of common flax (Linum usitatissimum L.) are known to contain as characteristic lignan sesoisolariciresinol diglucoside (SDG), whose presence in seeds of some other Linum species has also been reported. In order to investigate the material for the presence of such very polar lignans as well as for less polar non-glycosidic lignans as frequently found in aerial parts of Linum species, polar and non-polar extracts of each sample were analyzed by HPLC/ESI-MSMS. SDG was detected in 15 of 16 investigated seed samples of taxa representing sections Linum and Dasylinum. None of eight samples of taxa from sections Syllinum and Linopsis contained detectable amounts of SDG. Quite interestingly, most of the SDG-positive samples contained the 8R,8′R-isomer exclusively while only three (including L. usitatissimum) contained the 8S,8′S-stereoisomer as the predominant form. As a most noteworthy finding, the dichloromethane extracts obtained from seeds of several Linum species were found to contain significant concentrations of non-polar cyclolignans of the arylnaphthalene/-dihydronaphthalene lactone type or, alternatively of the aryltetralin lactone type. Thus, seeds of Linum perenne L. as well as those of several other representatives of sections Linum and Dasylinum were found to contain significant concentrations of the arylnaphthalene justicidin B along with further compounds of this type and some aryldihydronaphthalene-type lignans. On the other hand, seeds of Linum flavum and further representatives of section Syllinum were found to contain aryltetralin-type lignans, mainly in the form of esters with aliphatic carboxylic acids, such as 6-methoxypodophyllotoxin-7-O-n-hexanoate, whose occurrence in L. flavum seeds has very recently been reported by us for the first time. Various chemosystematic and biogenetic aspects are discussed in the light of these results.