Biochemical Systematics and Ecology 29 (2001) 331–333
Triterpenes and anthraquinones from
Picramnia
sellowii
Planchon in Hook (Simaroubaceae)
Luisa Balderrama
a, Alessandra Braca
b,*, Emilia Garcia
c,
Marcela Melgarejo
a, Cosimo Pizza
d, Nunziatina De Tommasi
daInstituto de Investigaciones Quimicas, Universidad Mayor de San Andres, Calle 27, esq. A. Bello, Cota
Cota, La Paz, Bolivia
bDipartimento di Chimica Bioorganica e Biofarmacia, Universita
di Pisa, Via Bonanno 33, 56126 Pisa, Italy
c
Herbario Nacional de Bolivia, Universidad Mayor de San Andres, Calle 27, esq. A. Bello, Cota Cota, La Paz, Bolivia
d
Dipartimento di Scienze Farmaceutiche, Universitadi Salerno, Via Ponte Don Melillo, 84084 Fisciano, Salerno, Italy
Received 8 February 2000; received in revised form 30 March 2000; accepted 1 May 2000
Keywords: Picramnia sellowii; Simaroubaceae; Triterpenes; Anthraquinones
1. Subject and source
The genusPicramnia (Simaroubaceae, subfamily Picramnioideae) includesca 40 species native to the New World tropics (Sima~o et al., 1991). Picramnia sellowii
Planchon in Hook is a medicinal plant used by the Moseten etnia in Bolivia for skin disease. Aerial parts of the plant were collected in Covendo, Province Sud Yungas, North of La Paz Department, Bolivia, in June 1996. A voucher specimen (No. GQP 107) has been deposited in the National Herbarium of Bolivia.
2. Previous work
Betulinic acid, 3-epibetulinic acid, chrysophanol, emodin, parietin, and benzoic acid were isolated from the bark ofPicramnia sellowiifrom Peru(Juan, 1973; Leon and Juan, 1975).
*Corresponding author. Fax: +39-50-43321.
E-mail address:[email protected] (A. Braca).
3. Present study
We report here the isolation of 4 triterpenes, 2 triterpene glycosides, 2 anthraquinones, and 2 sterols from the aerial parts ofPicramnia sellowii. Ground-dried aerial parts (500 g) of the plant were sequentially extracted at room temperature with petroleum ether, CHCl3, and MeOH. The extracts were concentrated in vacuo, yielding 3.0, 7.9, and 8.3 g of residues, respectively. The chloroformic extract was chromatographed on a silica gel column, using solvents with increasing polarity, starting from CHCl3. Fractions were collected in 25 ml volumes and combined according to TLC separations (Silica gel plates, in CHCl3or mixture CHCl3–MeOH) to give two pure sterols, b-sitosterol and cholesterol, together with ursolic acid and oleanolic acid. The methanolic residue was transferred to Sephadex LH-20 column using MeOH as eluent and collecting 102 fractions of 7 ml volumes. Fractions 21–30, combined according to TLC separations [Silica gel plates in,n-BuOH–AcOH–H2O (12 : 3 : 5) and CHCl3–MeOH–H2O (40 : 9 : 1)] were purified by RP-HPLC on a C-18m-Bondapak column (30 cm7.8 mm, flow rate 2 ml minÿ1
), using MeOH–H2O 1 : 1 as eluent to obtain pure picramnioside A (4 mg) and picramnioside C (4.5 mg). In the same way, using RP-HPLC with MeOH-H2O 7.5 : 2.5 as eluent, from fractions 37–40 oleanolic acid 28-O-b-D-glucopyranosyl ester (6.4 mg) and pomolic acid 28-O-b-D-glucopyranosyl ester (2.3 mg) were obtained, and from fractions 41–48 were separated echinocistic acid (3.5 mg) and pomolic acid (2.8 mg) eluting with MeOH–H2O 8 : 2. The structures of the isolated compounds were determined on the basis of spectral data (UV, MS, 1H and 13C NMR) and confirmed by comparison with literature data (Rubinstein et al., 1976; Mahato and Kundu, 1994; Solis et al., 1995).
4. Chemotaxonomic significance
The family Simaroubaceae are divided into five subfamilies the affinity of which are unclear. Generally plants of the family contain quassinoids with antiplasmodial and cytotoxic activities (O’Neill et al., 1987; Anderson et al., 1991). The genusPicramnia
seems to accumulate triterpenoids and anthraquinones: the latter derivatives were not found so far in any other group of Simaroubaceae and for this reason some authors prefer to remove all the subfamily of Picramniodeae from the Simaroubaceae (Noteboom, 1962; Cronquist, 1981). Our results are fully in agreement with the hypothesis because P. sellowiii does not biosynthesize quassinoids, but only triterpenoids and anthraquinones were separated from the Planchon in Hook plant.
References
Anderson, M.M., O’Neill, M.J., Phillipson, J.D., Warhurst, D.C., 1991. Planta Med. 57, 62.
Cronquist, A., 1981. An Integrated System of Classification of Flowering Plants. Columbia University Press, New York.
L. Balderrama et al. / Biochemical Systematics and Ecology 29 (2001) 331–333
Juan, J.L., 1973. Bol. Soc. Quim. Peru 39, 204. Leon, C., Juan, J., 1975. Bol. Soc. Quim. Peru 41, 14. Mahato, S.B., Kundu, A.P., 1994. Phytochemistry 37, 1517. Noteboom, H.P., 1962. Flora Malesiana Ser I Spermatophyta 6, 193.
O’Neill, M.J., Bray, D.H., Boardman, P., Chan, K.L., Phillipson, J.D., Warhust, D.C., Peters, W., 1987. J. Nat. Prod. 50, 41.
Rubinstein, I., Goad, L.J., Clague, A.D.H., Mulheirn, L.J, 1976. Phytochemistry 15, 195.
Sima~o, S.M., Barreiros, E.L., Das, G.F., DaSilva, M.F., Gottlieb, O.R., 1991. Phytochemistry 30, 853. Solis, P.N., Gutierrez Ravelo, A., Gonzales, A.G., Gupta, M.P., Phillipson, J.D., 1995. Phytochemistry
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