*Corresponding author. Tel.:#44-1224-262547; fax:#44-1224-262555.
E-mail address:s.sarker@rgu.ac.uk, (S.D. Sarker).
Biochemical Systematics and Ecology 29 (2001) 109}111
Lignans from
Cupressus lusitanica
(Cupressaceae)
Sally Cowan
!
, Barbara Bartholomew
!
, Alison A. Watson
!
,
Colin Bright
!
, Zahid Latif
!
, Satyajit D. Sarker
",
*
, Robert J. Nash
#
!Molecular Nature Limited, Plas Gogerddan, Aberystwyth, Ceredigion SY23 3EB, UK
"Pharmaceutical Sciences Section, School of Pharmacy, The Robert Gordon University, Schoolhill,
Aberdeen AB10 1FR, UK
#Institute of Grassland and Environmental Research, Plas Gogerddan, Aberystwyth, Ceredigion SY23 3EB, UK
Received 20 December 1999; accepted 14 February 2000
Keywords: Cupressus lusitanica; Cupressaceae; Lignan; Arctigenin; Matairesinol; Chemotaxonomy
1. Subject and source
Cupressus lusitanicaMill. (Family: Cupressaceae), commonly known as &Mexican cypress'or &Cedar-of-Goa', is an ornamental plant found extensively in Mexico, El Salvador, Guatemala and Honduras, and also in other parts of North and South America (USDA-ARS-GRIN database, 1999). Plant material was collected from Costa Rica and supplied by Biotics Limited, University of Sussex, Brighton, UK. A voucher specimen of this collection (MNL9606) has been retained at the herbarium of the Institute of Grassland and Environmental Research, Aberystwyth, UK.
2. Previous work
Tropolones have previously been reported from C. lusitanica (Yamaguchi et al., 1997; Sakai et al., 1994, 1997).
3. Present study
The CH
2Cl2 extract of stems ofC. lusitanica (1.05 kg) was fractionated by
Biot-ageTM 75 #ash chromatography on silica gel using a step gradient of increasing
polarity: n-hexane}EtOAc}MeOH with nine fractions of 1000 ml. Reversed-phase preparative HPLC (C
18 preparative column, eluted with a gradient
*water : acetonitrile : 0.1% TFA in acetonitrile"80 : 10 : 10}20 : 70 : 10 in 25 min,
55 ml/min, detection at 205 nm) of the#ash fraction 7 (75% EtOAc inn-hexane) has yielded arctigenin (1, 18.0 mg) (Rahman et al., 1990) and matairesinol (2, 28.0 mg) (Rahman et al., 1990). Compounds1and2were further puri"ed by reversed phase semi-preparative HPLC (C
18 semi-preparative column eluted isocratically at a#ow
rate 25 ml/min with a mobile phase water: 0.1% TFA in MeOH"40 : 60 for1and
water : acetonitrile"70 : 30 for2, detection at 210 nm). Structures of all these
com-pounds have been determined on the basis of UV, 1H NMR, 13C NMR, COSY, HMBC, HSQC, NOESY and LC-MS data, and direct comparison with the respective literature data.
4. Chemotaxonomic signi5cance
In addition to terpenoids, which is the major class of secondary metabolites found in the genusCupressus, benzoic acid derivatives, butenolides, #avonoids, furanone derivatives and sterols have previously been isolated from this genus (Dictionary of Natural Products, 1999). To our knowledge, this is the"rst report on the occurrence of arctigenin (1) and matairesinol (2) inCupressus. Compounds1and2were found in several other species of many di!erent plant families (Dictionary of Natural Products, 1999). The chemotaxonomic or ecological importance of these isolated compounds, either in the genusCupressusor in the family Cupressaceae, is still unknown.
Acknowledgements
References
Dictionary of Natural Products, 1999. CD-ROM Version 8:1, Chapman & Hall, Boca Raton, FL Rahman, M.M.A., Dewick, P.M., Jackson, D.E., Lucas, J.A., 1990. Phytochemistry 29, 1971. Sakai, K., Kusaba, K., Tsutsumi, Y., Shiraishi, T., 1994. Mokuzai Gakkaishi 40, 1. Sakai, K., Yamaguchi, T., Itose, R., 1997. Mokuzai Gakkaishi 43, 696.
USDA-ARS-GRIN database, 1999. National Germplasm Resources Laboratory, Beltsville, MD, USA, available on-line at: www.ars-grin.gov/cgi-bin/npgs/html/taxon.pl?12658
Yamaguchi, T., Itose, R., Sakai, K., 1997. J. Faculty Agric. Kyushu Univ. 42, 131.
