Forsskamide, a new ceramide from aerial parts of Forsskaolea tenacissima Linn.

Abstract

Although the various folk medicine uses and the biological activity of Forsskaolea tenacissima L., few chemical constituents of this plant have been reported, this provoked us to make our study. Forsskamide, a new ceramide was isolated from aerial parts of F. tenacissima L. (Urticaceae). The chemical structure was established by different spectroscopic methods (H, C-NMR, HMBC, HSQC, ROESY, FAB-MS and HR-FAB-MS). Forsskamide showed a moderate cytotoxic activity by (MTT) method against human colorectal carcinoma cell line (HCT-116) with IC 33.25 μM in comparison with 5-fluorouracil IC 26.42 μM. While, it did not show any activity against human hepatocarcinaoma cell line (HepG-2).

A New Cytotoxic Ceramide from Dalbergia boehmii Taub. Stem Bark

“…The 1D NMR spectra of this compound, shows characteristic signals, of a ceramide backbone, with generally an amide function and two long aliphatic chains, more or less unsaturated. [11][12][13][14][15] In the 1 H NMR spectrum of compound 1, a signal of a proton exchangeable with D 2 O is observed at δ H 8.57 (d, J = 9.0 Hz) advising the presence of the group -NH-CO-. Moreover, 13 C-NMR spectrum showed at δ C 53.0 a signal of C-N and a C=O signal at δ C 175.2 confirming the presence of a secondary amide function in this compound.…”

“…Moreover, 13 C-NMR spectrum showed at δ C 53.0 a signal of C-N and a C=O signal at δ C 175.2 confirming the presence of a secondary amide function in this compound. [15,16] 1 H NMR spectrum also exhibited resonances for terminal methyls of two aliphatic chains at δ H 0.87 (6H, t, J = 6.9 Hz), an azomethine proton at δ H 5.12 (1H, m), signals at δ H 4.51 (m) and 4.42 (m) for an hydroxymethylene group, three carbinylic protons at δ H 4.29 (H-4), 4.36 (m, H-3) and 4.61 (m, H-2ʹ), as well as signals of four -OH groups at δ H 6.21 (1H, brs), 6.68 (2H, brs) and 7.68 (brs). Two alkyl long chains were also observed as a broad signal at δ H 1.20-1.34.…”

“…Interpretation of the HMBC spectrum revealed correlations of the proton of amide group at δ H 8.57 and -C=O group at δ C 175.2 and the -CH-NH at δ C 53.0; correlations of H-2 (δ H 5.12) and C-1 (δ C 62.1) and C-3 (δ C 76.8); correlations of H-3 (δ H 4.36) and C-1 (δ C 62.1), C-2 (δ C 53.0), and C-4 (δ C 73.1), confirming positions of -OH groups on C-1, C-3 and C-4 (Figure 2). [15] Correlations between H-2ʹ (δ H 4.61) -C=O (δ C 175.2) and The length of the long chain base and the fatty acid was determined by EI-MS, which showed significant fragment ion peaks at m/z 384, 357 and 339 that were congruent to the long chain base moiety (Figure 3). The length of the fatty acid chain was deduced from the fragment at m/z 280 resulting from the cleavage in α of the carbonyl group of the amide function.…”

Phytochemistry and biological activity of family "Urticaceae": a review (1957-2019)

“…Many families of medicinal plants have biological importance viz., Urticaceae, Bignoniaceae,…etc. [1][2][3]. Urticaceae (syn.…”