Abstract
A new lactonic triterpene isolated from the heartwood of Austroplenckia populnea (Celastraceae) was characterized as 3a-hydroxyolean-12-en-29,22a-olide (the g-lactone of the 3a,22a-dihydroxyolean-12-en-29a-oic acid), the 3-epimer of the abruslactone A, on the basis of its spectral data, chemical transformations, and single crystal X-ray analysis.
Highlights
The investigation of chemical constituents of plants of the Celastraceae family has aroused considerable attention on account of the antitumoral and anti-leukemic activities found in maytansinoids and quinonemethide triterpenes isolated from plants of that family[1].In previous papers we described the chemical constitution of the root bark[2], bark wood[3] and root wood[4] of Austroplenckia populnea (Reiss) Lundell, specimen of the Celastraceae family
Both triterpenes were isolated from the ethanolic extract of the heartwood of Austroplenckia populnea, from which were isolated the following triterpenes previously found in other parts of the same plant: 3-oxofriedelan-29α-oic acid1,2,3, 3-hydroxy-2-oxofriedelan-3-en-29αoic acid, 3β-hydroxyolean-12-en-29α-oic acid[2], and 3-oxoolean-12-en-29α-oic acid[2]
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Summary
The investigation of chemical constituents of plants of the Celastraceae family has aroused considerable attention on account of the antitumoral and anti-leukemic activities found in maytansinoids and quinonemethide triterpenes isolated from plants of that family[1]. Mp. 319.5-322.0 °C (CHCl3/MeOH), [α]20 -34.2° (c = 1.0, CHCl3), 1H NMR (CDCl3, 200 MHz): δ (m) 5.30 (t, 1H, J = 3.0 Hz), 4.17 (d, 1H, J = 5.0 Hz), 3.2 (1H, dd, J = 6.0, 9.0 Hz), 1.21, 1.07, 0.99, 0.94, 0.93, 0.87, 0.79 (s, 3H each) in good agreement with previously reported data by Budzikiewicz, Wilson and Djerassi[10], Chang, Chiang and Mak[11] and Nozaki et at.[12]. 293 K on a CAD-4 Enraf Nonius diffractometer using Mo Kα radiation monochromated by graphite Intensity data for both crystals were collected in the 2θ range from 1 to 21°, using ω − 2θ scans with the scan width given by (0.8 + 0.35tnθ) and corrected for the Lp factors using the Enraf Nonius Structure Determination Package[6], hkl range: 0 < h < 11, 0 < k < 14, and -2 < l < 16. Total number of reflections measured: 1849 of which 1798 independent and 1677 had I > 2σ, and two standard reflections were monitored every hour which did not present any significant changes in intensities
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