Biochemical Systematics and Ecology 33 (2005) 305–307

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Iridoids, lignan, and triterpenes fromOsmanthus cymosus

Ammar Kubbaa, Francois Tillequina,*, Michel Kocha,Marc Litaudonb, Brigitte Deguina

aLaboratoire de Pharmacognosie de l’Universite Rene Descartes, U.M.R./C.N.R.S. n � 8638, Faculte des

Sciences Pharmaceutiques et Biologiques, 4, Avenue de l’Observatoire, F-75006 Paris, FrancebInstitut de Chimie des Substances Naturelles du C.N.R.S., 91190 Gif-sur-Yvette, France

Received 1 March 2004; accepted 26 June 2004

Keywords: Osmanthus cymosus; Oleaceae; Terpenoids; Iridoid glycosides; Lignan

1. Subject and source

The genus Osmanthus Lour. (Oleaceae) includes some 30 species from NorthernAmerica, Eastern Europe, South-east Asia, and the Pacific Islands. Osmanthuscymosus (Guillaumin) P.S. Green (ZNotelaea cymosa Guillaumin) is a shrub or asmall tree endemic to New Caledonia, distinct by its fasciculate inflorescence andslender few-flowered rachises (Green, 1963, 1998). Bark and leaves were collected atthe Dome de la Tiebaghi (New Caledonia) in December 1997. A voucher sample(Litaudon 0227) is kept in the herbarium of the Centre IRD of Noumea, NewCaledonia.

* Corresponding author. Tel.: C33 1 5373 9810; fax: C33 1 4046 9658.

E-mail address: francois.tillequin@univ-paris5.fr (F. Tillequin).

0305-1978/$ - see front matter � 2004 Elsevier Ltd. All rights reserved.

doi:10.1016/j.bse.2004.06.008

306 A. Kubba et al. / Biochemical Systematics and Ecology 33 (2005) 305–307

2. Previous work

To our knowledge, there is no published data on the chemistry of O. cymosus.

3. Present study

Dried leaves of O. cymosus (0.8 kg) were ground and extracted successively withCH2Cl2 (3! 2.5 L) and MeOH (3! 2.5 L) at room temperature. The combinedCH2Cl2 solutions were evaporated to dryness under reduced pressure (65 g) and analiquot of the residue (5 g) was subjected to repeated flash column chromatographyover silica gel (35–70 mm, solvent cyclohexane/ethyl acetate gradient of increasingpolarity), to afford a-amyrine (150 mg), b-amyrine (120 mg), b-sitosterol (52 mg),betulin (66 mg), and uvaol (108 mg). Similarly, the combined MeOH solutions wereevaporated (105 g). Column chromatography over silica gel (20–45 mm, solvent ethylacetate/methanol gradient of increasing polarity), of an aliquot (5 g) gave ursolicacid (1 g), oleoside dimethyl ester (40 mg), and oleuropein (120 mg).

Ground O. cymosus bark (0.7 kg) was extracted with MeOH (3! 2.5 L) atroom temperature. The combined MeOH solutions were evaporated (60 g). Repeatedflash column chromatography over silica gel (20-45 mm, solvent cyclohexane/ethylacetate gradient of increasing polarity) of an aliquot (5 g) gave ligstroside (50 mg),(C)-pinoresinol-b-D-glucopyranoside (200 mg), and syringin (125 mg).

All the compounds were identified unequivocally by comparison of their physicaland spectral properties ([a]D, UV, IR, MS, 1H NMR, and 13C NMR) and, whenrelevant, of those of their peracetylated derivatives, with literature data (Connollyand Hill, 1991; Agrawal and Jain, 1992; Gariboldi et al., 1986; Machida et al., 2002;Sugiyama and Kikuchi, 1991).

4. Chemotaxonomic significance

Results from chloroplast DNA sequencing have recently provided a basis for aphylogenic classification within the Oleaceae (Wallander and Albert, 2000). In thiscontext, the tribe Oleeae, to which belongs the genus Osmanthus Lour., consists ofclosely related taxa, whose strong relationships are reflected in the chemistry. Indeed,all the species of this tribe for which chemical data are available contain esters ofoleoside (Jensen et al., 2002). In good agreement with this statement, the threesecoiridoid glycosides isolated from O. cymosus belong to this series. The three Asianand American Osmanthus taxa previously investigated for their iridoid contentscontained both oleoside and 10-hydroxyoleoside esters (Jensen et al., 2002). Incontrast, the two New-Caledonian species, Osmanthus austrocaledonica (Vieill.)Knolb. (Benkrief et al., 1998) and O. cymosus, seem to have a different chemicalpattern, since they only contain oleoside esters.

307A. Kubba et al. / Biochemical Systematics and Ecology 33 (2005) 305–307

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