Hydrocarbons and sterols of Alstroemeria aurantiaca

Phytochemistry, Vol. 34, No. 2, pp. 581 582, 1993 Printed in Great Britain

0031-9422/93 $6.00+0.00 © 1993PergamonPress Ltd

HYDROCARBONS AND STEROLS OF A L S T R O E M E R I A A U R A N T I A C A B. E. MALDONI, M. T. LOCKHART and O. L. TOMBESI Instituto de Investigaciones en Quimica Org~inica,Depto. de Quimica e Ing. Quimica, Avenida Alem 1253, 8000 Bahia Blanca, Argentina (Received in revisedform 14 January 1993) K e y W o r d lndex--Alstroemeria aurantiaca; Alstroemeriaceae; n-alkanes; sterols.

Abstract--The sterol mixtures were isolated from the leaves, roots, flowers and seeds of Alstroemeria aurantiaca. Analysis of the mixtures by GC and GC-MS allowed the identification of A5- and A 7- sterols. The n-alkanes from each plant part were also identified by GC.

Table 1. n-Alkanes in Alstroemeria aurantiaca

INTRODUCTION Alstroemeria species are native to South America and have recently been introduced into Europe as ornamental plants, and hybridized in Europe. Anthocyanidins and flavonoids have been isolated from Alstroemeria species 11-3]. The only work on A. aurantiaca (Amancay) has been the isolation of anthocyanidins from its flowers [3]. We now wish to report the results of our research on A. aurantiaca, which include the characterization of hydrocarbons and sterols from the leaves, roots, flowers and seeds of the plant. RESULTSAND DISCUSSION Roots, leaves, flowers and seeds of A. aurantiaca were collected in San Carlos de Bariloche (Argentina). The dried and powdered plant material was extracted with petrol in a Soxhlet apparatus. The extract was saponified under reflux with ethanolic potassium hydroxide followed by extraction into diethyl ether to give the non-saponifiable lipid. This was chromatographed on a silica gel column to give fractions containing hydrocarbons and sterols which were purified by preparative TLC (HF366+254, hexane-diethyl ether, 7 : 3). The sterol fraction obtained from the seeds showed, under UV (360 nm), two bands with different fluorescence, which were scraped off and eluted with chloroform. One of the bands give AT-sterols. The leaves (110 g) yielded hydrocarbons (90 mg) and sterols (50 mg); roots (200 g) yielded, hydrocarbons (37 mg), sterols (32 mg); flowers (270 g) yielded hydrocarbons (90 mg), sterols (20 rag); seeds (600 g) contained hydrocarbons (93 rag), sterols: fraction a (98 rag) and fraction b (14 mg). Alkanes were identified by comparison of their retention data with those of standard alkanes and from a plot of hydrocarbon number vs log Rt. The relative amounts of each alkane were determined by peak area measurements (Table 1). PHYTO 34:2-R

Carbon No.

Seeds %

17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33

-7

4 3 4 2 1.5 1 2 1 7 3 30 3 18 1 11

Flowers %

Roots %

Leaves %

2

--

--

5

2

--

6 4 3 3 4 4 5 4 l0 11 14 8 8 8 --

3 2 3 2 4 4 12 7 26 6 14 4 8 ---

----2 1 12 2 63 l 18 -1 ---

The sterol fractions were acetylated and analysed by GC and GC-MS. The mass spectra of sterol acetates were in accord with published mass spectra [4-9] (Table 2). EXPERIMENTAL

GC was performed with a Varian model 3700 gas chromatograph equipped with a F I D detector and a metallic column (2 m x 2 mm); using temp. programmed from 180 to 2800 at 10° min -1. GC-MS analysis of the acetylated sterols was performed on a Varian Mat CH7 A mass spectrometer at 70 eV coupled to a Varian 1400 gas chromatograph and interfaced to a Varian Mat Data System 166 computer. Chromatographic conditions were as previously indicated. 581

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Table 2. The sterols identified in the seeds, flowers, leaves and roots of AIstroemeria aurantiaca Sterols

RR r

Seeds %

Flowers %

Leaves %

Roots %

Cholest-5-en-3fl-ol 24-Methylcholesta-5,22-dien-3fl-ol 24-Methyicholest-5-en-3fl-ol 24-Methylcholesta-5,24 (24')-dien-3fl-ol 24-Ethylcholesta-5,22-dien-3fl-ol 24-Ethylcholest-5-en-3fl-ol 24-Ethylidene-cholest-5-en-3fl-ol 24- Methylcholesta-7,22-dien-3fl-oi 24-Methylcholesta-7,24 (24')-dien-3fl-ol 24-Methylcholest-7-en-3fl-ol 24-Ethylcholest-7-en-3fl-ol

0.85 0.91

Traces Traces

11 --

--

1

39

--

--15

1

--

28

--

--

1.05

--

--

1.15

61

-85

73

--

--

--

1.01

27 34 30

--

--

--

1.13

25

--

--

--

1.17

38

--

--

--

--

--

--

Acknowledgements--We thank Ing. S. Lamberto (Universidad Nacional del Sur) for botanical classifications. We are grateful to Dr E. G. Gros (Universidad de Buenos Aires) for G C - M S of sterols. REFERENCES

1. Pena, S. W., Fern:mdez, B. E. and Diaz, P. J. (1984) Rev. Latinoam. Quire. 15, 131. 2. Saito, N., Yokoi, M., Yamaji, M. and Honda, T. (1985) Phytochemistry 24, 2125. 3. Saito, N., Yokoi, M., Ogawa, M. and Honda, T. (1988) Phytochemistry 27, 1399.

1.24

1.30

7

17 I0

4. Knights, B. A. (1967) J. Gas Chromatoor. 273. 5. Wyllie, S. G. and Djerassi, C. (1968) J. Org. Chem. 33, 305. 6. Wojciechowski, Z. A., Goad, L. J. and Goodwin, T. W. (1973) Phytochemistry 12, 1433. 7. Smith, A. G., Rubinstein, I. and Goad, L. J. (1973) Biochem. J. 135, 443. 8. Seldes, A. M., Rovirosa, J., San Martin, A. and Gros, E. G. (1985) Comp. Biochem. Physiol. 81B, 119. 9. Romero, M. S. and Seldes, A. M. (1985) A. Asoc. Quire. Argent. 73, 215.