*Corresponding author. Tel.:#44-1970-823201; fax:#44-1970-823209.
E-mail address:[email protected]. (R.J. Nash)
Biochemical Systematics and Ecology 28 (2000) 799}801
Calendin, tyrosol and two benzoic acid derivatives
from
Veronica persica
(Scrophulariaceae)
Satyajit D. Sarker
!
, Colin Bright
!
, Barbara Bartholomew
!
, Alison
A. Watson
!
, Robert J. Nash
"
,
*
!MolecularNature Limited, Plas Gogerddan, Aberystwyth, Ceredigion SY23 3EB, UK
"Institute of Grassland and Environmental Research, Plas Gogerddan, Aberystwyth, Ceredigion SY23 3EB, UK
Received 21 September 1999; accepted 26 October 1999
Keywords: Veronica persica; Scrophulariaceae; Calendin; Loliolide; Vanillic acid;p-salicylic acid; Tyrosol; Chemotaxonomy
1. Subject and source
Veronica persicaPoiret (Family: Scrophulariaceae), the`Common Field Speedwella
or `Persian speedwella, is a neophytic weed originally from south-west Asia and widely distributed in the temperate regions (USDA-ARS GRIN database, 1999; Fischer, 1987; Holm et al., 1979). The plants were garden weeds and collected in#ower near Aberystwyth (Tyn-y-Graig, Wales), and a voucher specimen (N9623) of this collection has been retained in the herbarium at the Institute of Grassland and Environmental Research (IGER) also known as WPBS, Aberystwyth, Wales.
2. Previous work
Previous phytochemical studies on V. persica revealed the presence of iridoid glycosides (Komai et al., 1991; Lahloub et al., 1990, 1991), phenylethanoid glycosides (Aoshima et al., 1994a; Lahloub et al., 1986), and alkaloids (Viladomat et al., 1986).
3. Present study
The CH
2Cl2extract of the leaves and stems ofV. persica(1.0 kg) was fractionated by BiotageTM75#ash chromatography on silica gel using a step gradient of increasing polarity:n-hexane}EtOAc}MeOH with 9 fractions of 1000 ml. Reversed phase prep-arative HPLC (C
18 preparative column, eluted with a gradient 10}100% acetonitrile (ACN) in water in 40 min, 55 ml/min, detection at 210 nm) of the #ash chromato-graphic fraction, 6 (50% EtOAc in n-hexane) has yielded p-salicylic acid (4-hy-droxybenzoic acid, 1, 4.5 mg) (Aldrich Library of 13C and 1H FT NMR Spectra, 1992b), vanillic acid (4-hydroxy-3-methoxybenzoic acid,2, 5.3 mg) (Aldrich Library of 13C and1H FT NMR Spectra, 1992c), tyrosol (4-hydroxyphenethyl alcohol,3, 6.5 mg) (Aldrich Library of13C and1H FT NMR Spectra, 1992a), and calendin, (loliolide,4, 6.2 mg) (Okada et al., 1994). Compounds3 (5.5 mg) and4(2.3 mg) have also been isolated from the#ash chromatographic fraction, 7 (100% EtOAc) using the same HPLC method. Structures of all these compounds have been determined conclusively on the basis of UV,1H NMR, COSY45,13C NMR, and LC-MS data, and direct comparison with the respective literature data.
4. Chemotaxonomic signi5cance
reported here (1+4) has previously been reported from V. persica. However, the
presence of tyrosol (3) inV. persicais in good agreement with the chemotaxonomic distribution of such compounds or their glycosides in the genusVeronica(Ozipek et al., 1999; Aoshima et al., 1994a,b; Lahloub et al., 1986). Calendin (4), also known as loliolide, has been isolated from several plant families (Dictionary of Natural Prod-ucts, 1999), and reported to have inhibitory activities against plant germination (Hiraga et al., 1997) and is repellent to ants (Okunade and Weimer, 1985). Its chemotaxonomic or detailed ecological signi"cance, however, is yet to be established.
Acknowledgements
We thank Felicity Currie, Julia Turnock and Nicola Barnes for the pre-HPLC preparation of the plant extract, and David Thomas for his assistance with LC-MS data. BBSRC are thanked for"nancial support.
References
Aldrich Library of13C and1H FT NMR Spectra. 1992a. 2, 409A.
Aldrich Library of13C and1H FT NMR Spectra. 1992b. 2, 1080A,B; 1081C; 1082B. Aldrich Library of13C and1H FT NMR Spectra. 1992c. 2, 1110C; 1115C; 1116A. Aoshima, H., Miyase, T., Ueno, A., 1994a. Phytochemistry 37, 547.
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Ozipek, M., Saracoglu, I., Kojima, K., Ogihara, Y., Calis, I., 1999. Chem. Pharm. Bull. 47, 561. USDA-ARS-GRIN database, 1999. National Germplasm Resources Laboratory, Beltsville, MD, USA,
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