*Corresponding author.
E-mail address:[email protected] (G.L. von Poser)
Biochemical Systematics and Ecology 28 (2000) 907}910
Constituents of
Valeriana glechomifolia
Meyer
Luisa de A. Salles
!
, Andreia L. Silva
!
, Sandra B. Rech
!
,
Nilo Zanatta", Gilsane L. von Poser!
,
*
!Curso de Po&s-Graduac7aJo em CieLncias FarmaceLuticas, UFRGS, Av. Ipiranga, 2752, 90.610-000, Porto Alegre, Brazil
"Departamento de Qun&mica, Universidade Federal de Santa Maria, CCNE, 97119-900, Santa Maria, Brazil
Received 15 July 1999; accepted 18 November 1999
Keywords: Valeriana; Valepotriates; Valtrate; Diavaltrate; Acevaltrate; 1-b-aceacevaltrate; Didrovaltrate; AHD-valtrate; Dihydrocornin; Chemotaxonomy
1. Subject and source
Valeriana glechomifoliaMeyer is a small herb 5}10 cm high, growing in South Brazil.
The plant was collected in April, 1998 in Sa8o JoseH dos Ausentes, RS, Brazil and identi"ed by M. Sobral (Curso de PoHs-Graduac7a8o em Cie(ncias Farmace(uticas da Universidade Federal do Rio Grande do Sul, Brazil). Voucher specimens (M. Sobral, 7733) are kept in the Herbarium of the Universidade Federal do Rio Grande do Sul (ICN).
2. Previous work
The main compounds isolated fromValerianaspecies are essential oils, valerenic acid and its derivatives and iridoids which are accumulated mainly in the roots and rhizomes (Bos et al., 1998). The most important iridoid compounds found in Val-erianaceae are the valepotriates (valtrate, isovaltrate, acevaltrate, didrovaltrate and their homologues) which are restricted in occurrence to the Valerianaceae and display some special structural features not encountered in other iridoids. Iridoid glycosides
have also been isolated from the family. Reports on the presence of normal iridoid glucosides, with the glucose linked to C1, in Valerianaceae are scarce. Most frequently found are the so-called`valeriana compoundsa, which are characterized by having an isovaleric ester at C-1 and a glycosyl moiety at C-11. Besides Valerianaceae, they have been found in some genera such asViburnum and Sambucus (Caprifoliaceaesensu
Cronquist, 1981) (Bock et al., 1978; Boros and Stermitz, 1991) and, surprisingly, in some species ofPenstemon(Scrophulariaceae) (Jensen, 1991).
3. Present study
V. glechomifoliawas analyzed for the presence of iridoids by TLC. Valepotriates
and iridoid glucosides were found almost in the same amount in both the aerial and subterraneous parts. The freeze-dried plant material, consisting of the whole plant, was extracted successively with chloroform and ethanol in an ultrasonic bath. The chloroform fraction yielded, after preparative TLC (20]20 plates coated with 0.5 mm layers of silica gel GF
254; bands were detected in UV light 254 nm) with chloroform: methanol (50 : 0.5) as eluent, the dienic valepotriates valtrate (1, Thies et al., 1981; Mikhova et al., 1987), diavaltrate (2, Handjieva and Zaikin, 1978; Mikhova et al., 1987; Bach et al., 1993), acevaltrate (3, Thies et al., 1981; Mikhova et al., 1987) and 1-b-aceacevaltrate (4, Becker et al., 1986), and the monoenic didrovaltrate (5, Thies et al., 1981; Mikhova et al., 1987) and AHD-valtrate (6, Handjieva et al., 1978; Mikhova et al., 1987). The ethanolic extract was concentrated and partitioned in Et
2O}H2O. The concentrated aqueous phase submitted to preparative TLC with chloroform: methanol (8 : 2) as eluent, gave dihydrocornin (7, Franzyk et al., 1998; Damtoft et al., 1981). The products were identi"ed by means 1H and 13C NMR, recorded at 400 and 100 MHz, respectively.
4. Chemotaxonomic signi5cance
All the valepotriates isolated fromV. glechomifoliaare commonly found in
Val-erianaspecies. The exception is 1-b-aceacevaltrate which was previously reported only
from Phyllactis pulvinata Rauh et Willer, a plant growing in the peruvian Andes
(Becker et al., 1986). The genus Phyllactis is sometimes included in Valeriana or recognized as a section ofValeriana(Eriksen, 1989).
Among the products isolated fromValeriana glechomifolia the presence of dihyd-rocornin deserves comments. This compound isolated from the polar fraction has so far never been described in Valerianaceae and di!ers from the iridoid glycosides usually found inValerianaspecies. Dihydrocornin was previously found inViburnum
dentata(Caprifoliaceae sensu Cronquist, 1981) (Norn, 1978). The common occurrence
of valeriana compounds in Valerianaceae,ViburnumandSambucussuggests that these taxa may be closer related than is commonly though. The co-occurrence of dihyd-rocornin in a Valeriana and a Viburnum species could further corroborate such a notion.
Acknowledgements
The authors want to thank CNPq, FAPERGS and CAPES for the "nancial support.
References
Bach, K., Ghia, F., Torssell, K.B.G., 1993. Planta Med. 59, 478.
Becker, H., Chavadej, S., Tauscher, B., Abram, A.P., Finner, E., Borchers, F., 1986. Phytochemistry 25, 1250. Bock, K., Jensen, S.R., Nielsen, B.J., Norn, V., 1978. Phytochemistry 17, 753.
Boros, C.A., Stermitz, F.R., 1991. J. Nat. Prod. 54, 1173.
Bos, R., Woerdenbag, H.J., van Putten, F.M.S., Hendriks, H., Sche!er, J.J.C., 1998. Planta Med. 64, 143. Cronquist, A., 1981. An Integrated System of Classi"cation of Flowering Plants. Columbia University
Press, New York.
Damtoft, S., Jensen, S.R., Nielsen, B.J., 1981. Phytochemistry 20, 2717. Eriksen, B., 1989. Nord. J. Bot. 9, 179.
Franzyk, H., Jensen, S.R., Stermitz, F.R., 1998. Phytochemistry 49, 2025. Handjieva, N., Zaikin, V.G., 1978. Planta Med. 34, 203.
Jensen, S.R., 1991. Plant iridoids, their biosynthesis and distribution in angiosperms. In: Harborne, J.B., Tomas-Barberan, F.A. (Eds.), Ecological Chemistry and Biochemistry of Plant Terpenoids. Clarendon Press, Oxford, pp. 133}158.
Mikhova, B.P., Handjieva, N.V., Popov, S.S., Spassov, S.L., 1987. J. Nat. Prod. 50, 1141. Norn, V., 1978. Lic. Tech. Thesis. The Technical University of Denmark, Lyngby. Thies, P.W., Finner, E., David, S., 1981. Planta Med. 41, 15.
