Biochemical Systematics and Ecology 29 (2001) 869–871
Sesquiterpene lactones from Lugoa revoluta Jorge Trianaa, Jose´ L. Eiroaa, Mariana Lo´peza, Juan J. Ortegaa, Antonio G. Gonza´lezb, Jaime Bermejo Barrerab,* a
Departamento de Quı´mica, Universidad de Las Palmas de Gran Canaria, Campus de Tafira, 35017 Las Palmas de Gran Canaria, Canary Islands, Spain b Instituto Universitario de Bio-Orga´nica ‘‘Antonio Gonza´lez’’, Instituto de Productos Naturales y Agrobiologı´a del C.S.I.C, Avda. Astrofisico Francisco Sa´nchez 3,38206 La Laguna, Tenerife, Canary Islands, Spain Received 3 October 2000; accepted 18 December 2000
Keywords: Lugoa revoluta; Compositae; Anthemideae; Sesquiterpene lactones; Germacranolides; Eudesmanolides
1. Subject and source The genus Lugoa DC is endemic to the Canary Islands and consists of a single species, L. revoluta (Chr. Sm.) DC, localized in the Anaga peninsula, in NE Tenerife (Bramwell and Bramwell, 1990). From a taxonomic point of view, it is closely related to the species of the genus Gonospermum, which is also a Canarian endemic, as evidenced by the formation of fertile hybrids with G. fruticosum Less (Go´mez et al., 1996). The aerial parts of L. revoluta were collected in May 1995 at Roque de las A´nimas (Taganana, Tenerife). A voucher specimen (LPA-18665) is deposited at the Herbarium of the Viera y Clavijo Botanical Garden in the island of Gran Canaria.
2. Previous work None
*Corresponding author. Tel.: +34-922-318583; fax: +34-922-250766. E-mail address:
[email protected] (J. Bermejo Barrera). 0305-1978/01/$ - see front matter # 2001 Elsevier Science Ltd. All rights reserved. PII: S 0 3 0 5 - 1 9 7 8 ( 0 1 ) 0 0 0 2 3 - 0
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J. Triana et al. / Biochemical Systematics and Ecology 29 (2001) 869–871
3. Present study The air-dried material was extracted with ethanol and the extract analysed by column chromatography and preparative TLC on silica gel. The compounds isolated were identified by comparison of their physical and spectroscopic data (IR, 1H and 13 C NMR, EIMS) with those reported in the literature. The compounds identified were the coumarins scopoletin and scoparone (Murray et al., 1982), the flavonoids betuletol 3-methyl ether (Wollenweber and Lebreton, 1971) and apigenin (Sashida et al., 1983) and the germacranolide sesquiterpene lactones tatridins A and B (Sanz and Marco, 1991), 1a-hydroxydeacetyltulirinol4a,5b-epoxide (Rustaiyan et al., 1990), tatridin B-6-O-methacrylate (Bohlmann et al., 1983), 1-epi-tatridin B-6-O-methacrylate (Bohlmann et al., 1983), 1-epitatridin B-6-O-angelate (Bohlmann et al., 1983), 1a,10b-epoxydeacetyllaurenobiolide (Bohlmann et al., 1983), tamirin (Sanz et al., 1991) and the eudesmanolides tanapsin (Bohlmann et al., 1983) and deacylchrysanin-6-O-angelate (Doskotch et al., 1971).
4. Chemotaxonomic significance The taxonomic position of Gonospermum and Lugoa, as with many components of the tribe Anthemideae, has been highly controversial since the morphological differentiations established within the tribe are seldom of any taxonomic value. Cytogenetic and evolutionary studies (Febles, 1990) have led to the conclusion that Gonospermum and Lugoa are taxonomically related, and a proposal has been put forward to group all the species, together with all the endemic Canarian species of the genus Tanacetum, in a single endemic genus, Gonospermum. The results obtained in the chemical study of L. revoluta show a high content in sesquiterpene lactones similar to those described in previous studies of endemic Tanacetum (Gonza´lez et al., 1992) and Gonospermum (Triana et al., 2000) species, all of which supports the proposal to reconsider the taxonomic status of these species.
Acknowledgements This work has been partially supported by Grant No. PB96-1234 (Direccio´n General de Ensen˜anza Superior e Investigacio´n Cientı´ fica) and FEDER (1FD 1997-1831).
References Bohlmann, F., Jakupovic, J., Ahmed, M., Schuster, A., 1983. Phytochemistry 22, 1623. Bramwell, D., Bramwell, Z.I., 1990. Flores Silvestres de las Islas Canarias, Editorial Rueda, Madrid, pp. 294. Doskotch, R.W., El-Feraly, F.S., Hufford, C.D., 1971. Can. J. Chem. 49, 2103.
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