Biochemical Systematics and Ecology 29 (2001) 325–327
Pinoresinol and syringaresinol: two lignans
from
Avicennia germinans
(Avicenniaceae)
Hazel Sharp
a, David Thomas
a, Felicity Currie
a, Colin Bright
a,
Zahid Latif
a, Satyajit D. Sarker
b,*, Robert J. Nash
caMolecularNature Limited, Plas Gogerddan, Aberystwyth, Ceredigion SY23 3EB, UK bPharmaceutical Sciences Section, School of Pharmacy, The Robert Gordon University, Schoolhill,
Aberdeen AB10 1FR, Scotland, UK
c
Institute of Grassland and Environmental Research, Plas Gogerddan, Aberystwyth, Ceredigion SY23 3EB, UK
Received 20 December 1999; accepted 2 April 2000
Keywords: Avicennia germinans; Avicenniaceae; Verbenaceae; Lignan; Pinoresinol; Syringaresinol; Chemotaxonomy
1. Subject and source
Avicennia germinans(L.) L. (Family: Avicenniaceae alt. Verbenaceae), commonly known as ‘‘black mangrove’’ is widely distributed in West Africa, and 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 (MNL10040) has been retained at the herbarium of the Institute of Grassland and Environmental Research, Aberystwyth, UK.
2. Previous work
Iridoid glucosides have previously been reported fromA. geminans(Fauvel et al., 1999, 1997, 1995; Bousquet-Melou and Fauvel, 1998), and from other species of the genus Avicennia (Nass and Rimpler, 1996; Pandey and Garg, 1996; Ko¨nig et al., 1987; Ko¨nig and Rimpler, 1985; Majumdar et al., 1981). Betaines (AdrianRomero
*Corresponding author. Tel: +44-1224-262547; fax: +44-1224-262555.
E-mail address:[email protected] (S.D. Sarker).
et al., 1998), phenylpropanoid glycosides (Fauvel et al., 1993) and megastigmane (Fauvel et al., 1999) have also been isolated from this genus.
3. Present study
BiotageTM 75 flash chromatography (silica gel, eluting with a step gradient of increasing polarity:n-hexane2EtOAc2MeOH) of the CH2Cl2extract of branches ofA. germinans(0.84 kg) has yielded nine fractions (1000 mL each). Reversed-phase preparative HPLC (C18 preparative column, eluted with a gradient water: acetonitrile: 0.1% TFA in acetonitrile=80 : 10:10 to 50 : 40:10 in 25 min, 55 ml/ min, detection at 205 nm) of the flash fraction 7 (75% EtOAc in n-hexane) has
afforded pinoresinol (1, 11.1 mg) (Vermes et al., 1991). Syringaresinol (2, 5.6 mg) (Vermes et al., 1991) has been isolated from flash fraction 8 (100% EtOAc) using the same purification method. Structures of these compounds have been determined by UV, LC-MS and extensive NMR (1D and 2D) analyses, and also by direct comparison with the respective literature data.
Chemotaxonomic significance
To our knowledge, this is the first report on the occurrence of lignans in the Avicenniaceae. The Avicenniaceae comprises only the genus Avicennia which was previously described under the family Verbenaceae. Lignans have previously been reported from the Verbenaceae (Kawazoe et al., 1999; Habtemariam et al., 1995; Chawla et al., 1992). The systematic position ofAvicenniahas not been established yet (Fauvel et al., 1995). Lignans, are widely distributed in the plant kingdom (Castro et al., 1996), and apparently have very limited importance in plant systematics. However, the occurence of lignans (1,2) in A. germinans, a
H. Sharp et al. / Biochemical Systematics and Ecology 29 (2001) 325–327
taxonomically very complicated species in which considerable variations do exist between populations growing in the Old, and New World (Dodd et al., 2000), might have some chemotaxonomic implications.
Acknowledgements
BBSRC is thanked for partial financial support for the purchase of a Bruker DRX500 NMR spectrometer.
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