New Sphingolipids and Other Constituents of Pancovia laurentii

Abstract

Phytochemical investigation of the bark and leaves of Pancovia laurentii (Sapindaceae) resulted in the isolation of a new ceramide and a new cerebroside, named pancoviamide (1), and pancovioside (2) respectively, together with six known compounds: uracil, (R)-N-[(1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadec-5-en-1-yl]-2-hydroxytetracosanamide, stigmasta-7,22-dien-3-ol, b-stitosterol, b-sitosterol 3-O-b-d-glucopyranoside, and 2,3-dihydroxypropyl pentadecanoate. The structures of 1 and 2 were determined by means of spectroscopic methods. Compounds 1 and 2 were tested in vitro for their antiprotozoal properties against several protozoa and for their cytotoxicity.

A New Bioactive Diterpene Glycoside from Molinaea Retusa from the Madagascar Dry Forest

“…The structure of compound 1 was found to be very similar to 2 and 3 based on comparison of their 1 H NMR and 13 C NMR spectroscopic data. The 1 H NMR and 13 C NMR showed that five methyl groups (δ 1.60, 6H, s; δ 1.60, 3H, s; δ 1.61, 3H, s; δ 1.67, 3H, s; and δ 1.70, 3H, s) together with a broad triplet at δ 5.39 were present, consistent with the presence of a geranylgeraniol group as found in 2 and 3 [3]. The 1 H and 13 C NMR spectra exhibited two anomeric protons, suggesting the presence of two sugar units.…”

“…Plants of the Sapindaceae family are known to contain terpenoids, flavonoids, and ceramides, with varying types of activity, including antiproliferative and antiplasmodial activities [3]. Molinaea retusa is one of ten members of the Molinaea genus, all of which are endemic to Madagascar [2].…”

“…Molinaea retusa is one of ten members of the Molinaea genus, all of which are endemic to Madagascar [2]. During this study, one unreported compound, 2″,3″,4″,6′-de- O -acetylcupacinoside ( 1 , IC 50 15.4 μM) (Figure 1) and two known compounds, cupacinoside ( 2 , IC 50 9.5 μM, 4.0 μM) and 6′-de- O -acetylcupacinoside ( 3 , IC 50 10.9 μM, 6.4 μM) (Figure 1) were isolated (IC 50 values against the A2780 ovarian cancer cell line and Plasmodium falciparum strain Dd2, respectively)[3a]. …”

“…Compounds 2 and 3 were previously isolated from Cupania cinerea (Sapindaceae) with activities of 1.3 μM ( 2 ) and 2.1 μM ( 3 ) against P. falciparum (K1 strain) and activities of 11.6 μM ( 2 ) and 8.7 μM ( 3 ) against rat skeletal myoblast cells (L-6 cell line) [3a]. …”

“…Further bioassay-guided isolation, including the use of C 18 reverse phase chromatography and amino normal phase chromatography, yielded three bioactive compounds with moderate antiproliferative activity exhibited against the A2780 ovarian cancer cell line. Two of the compounds, cupacinoside ( 2 ) and 6′-de- O -acetylcupacinoside ( 3 ) have previously been reported and were identified through comparison of 1 H NMR, 13 C NMR, and HRESIMS spectroscopic data with previously published data [3a]. …”