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Isolation and characterisation of selected germander diterpenoids from authenticated Teucrium chamaedrys and T. canadense by HPLC, HPLC‐MS and NMR
Author(s) -
Sundaresan P. Ramnathan,
Slavoff Sarah A.,
Grundel Erich,
White Kevin D.,
Mazzola Eugene,
Koblenz Daniel,
Rader Jeanne I.
Publication year - 2006
Publication title -
phytochemical analysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.574
H-Index - 72
eISSN - 1099-1565
pISSN - 0958-0344
DOI - 10.1002/pca.912
Subject(s) - teucrium , chemistry , high performance liquid chromatography , chromatography , terpenoid , proton nmr , organic chemistry , botany , stereochemistry , biology , lamiaceae
Teucrium species, such as germander, are rich in neo ‐clerodane diterpenoids and have been used in traditional folk medicine for their stimulant, diuretic, antipyretic and antiseptic properties. However, the furano neo ‐clerodane diterpenoids present in germander have been implicated in the in vivo hepatotoxicity of this botanical. In this study, authenticated germander ( Teucrium chamaedrys L. and Teucrium canadense L.) was used as the source material. Methanol extracts of powdered plant material were prepared and analysed by HPLC using Synergi ® Max‐RP columns with monitoring at 220 nm. Limited amounts of teucrin A and other diterpenoid standards were analysed on a Synergi Max‐RP column in order to determine their retention times and to generate calibration curves. The same standards were subjected to concurrent mass spectral analysis. Teucrin A and diterpenoids such as dihydroteugin, teuflin, teuflidin and teucvidin were tentatively identified in the plant extracts by HPLC‐MS and 1 H‐NMR experiments. For the isolation of teucrium diterpenoids on a semipreparative scale, a solid‐phase extraction method was developed for the first time using styrene divinylbenzene and strata‐X sorbents for teucrin A and teuflin, respectively. Semi‐preparative HPLC of the methanol extract of the powdered aerial parts of Teucrium plants was carried out on a semipreparative Synergi Max‐RP column with photodiode array detection in order to confirm the identities of some diterpenoids by HPLC‐MS and NMR. Copyright © 2006 John Wiley & Sons, Ltd.