*Corresponding author. Tel.:#44-1224-262547; fax:#44-1224-262555.
E-mail address:[email protected] (S.D. Sarker).
Biochemical Systematics and Ecology 29 (2001) 209}211
N
-
trans
-feruloyltyramine from two species of the
Solanaceae
Julia Turnock
!
, Sally Cowan
!
, Alison Watson
!
,
Barbara Bartholomew
!
, Colin Bright
!
, Zahid Latif
!
,
Satyajit D. Sarker
"
,
*
, Robert J. Nash
#
!MolecularNature Limited, Plas Gogerddan, Aberystwyth, Ceredigion SY23 3EB, UK
"Pharmaceutical Sciences Section, School of Pharmacy, The Robert Gordon University, Schoolhill, Aberdeen AB10 1FR, Scotland, UK
#Institute of Grassland and Environmental Research, Plas Gogerddan, Aberystwyth, Ceredigion SY23 3EB, UK
Received 4 January 2000; received in revised form 15 February 2000; accepted 28 February 2000
Keywords: Cestrum lanatum;Solanum citrullifolium; Solanaceae;N-trans-feruloyltyramine; Chemotaxon-omy
1. Subject and source
Cestrum lanatum Mart. & Gal. (Family: Solanaceae) is a species of the central American genusCestrum(USDA-ARS-GRIN database, 1999a). The aerial parts of this plant were collected from Costa Rica and supplied by Biotics Limited, University of Sussex, Brighton, UK. A voucher specimen (BT177) for this collection has been retained by the supplier.Solanum citrullifoliumA. Braun, a plant from north America (USDA-ARS-GRIN database, 1999b) of the family Solanaceae, was grown at IGER greenhouse during 1997, aerial parts were collected, and a voucher specimen (IG85) has been deposited at the herbarium of IGER.
2. Previous work
None
3. Present study
The CH
2Cl2extract of the aerial parts ofCestrum lanatum(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. Reverse-phase prep-arative HPLC (C
18 preparative column, eluted with a gradient*water :
acetonit-rile : 0.1% TFA in acetonitacetonit-rile"90 : 00 : 10}00 : 90 : 10 in 25 min, 55 ml/min,
detec-tion at 210 nm) of the#ash fraction 7 (75% EtOAc inn-hexane) has yielded N-trans-feruloyltyramine (1, 15.4 mg) (Sarker et al., 2000; Fukuda et al., 1983). Similar treat-ment of the CH
2Cl2extract of the aerial parts ofSolanum citrullifolium(0.73 kg) also
produced compound1(25.0 mg). Structure of1has been determined on the basis of UV,1H NMR,13C NMR and LC-MS data, and direct comparison with the literature data.
4. Chemotaxonomic signi5cance
Glycoalkaloids are the major secondary metabolites found in the species of both the generaCestrumandSolanum(Dictionary of Natural Products, 1999). While N-trans-feruloyltyramine (1) has never been reported from any species of the genusCestrum, it has been found in the genus Solanum(Keller et al., 1996; Muhlenbeck et al., 1996; Negrel et al., 1996), and also in other genera of the family Solanaceae (Negrel and Martin, 1984; Pearce et al., 1998). Compound1has also been isolated from several other families, notably, Annonaceae (Chaves and Rouque, 1997; Chen et al., 1998, 1997; Wu et al., 1995), Aristolochiaceae (Wu et al., 1994), Balanitiaceae (Sarker et al., 2000), Cannabaceae (Matsunaga et al., 1997), Fumariaceae (Rucker et al., 1994; Hussain et al., 1982), Liliaceae (Latvala et al., 1995), Menispermaceae (Cavin et al., 1998), Papaveraceae (Gozler et al., 1992) and Plumbaginaceae (Yue et al., 1997). The chemotaxonomic or ecological signi"cance of N-trans-feruloyltyramine is yet to be established.
Acknowledgements
We thank David Thomas for his assistance with LC-MS data. BBSRC is thanked for partial"nancial support for purchasing the BRUKER DRX500 NMR spectro-meter.
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