Anticancer and Antioxidant Tannins from Pimenta dioica Leaves

Author:

Marzouk Mohamed S. A.1,Moharram Fatma A.2,Mohamed Mona A.3,Gamal-Eldeen Amira M.4,Aboutabl Elsayed A.5

Affiliation:

1. Natural Products Group, Nobel Project Laboratory, National Research Centre, El-Behoos St., Dokki, Cairo, Egypt

2. Department of Pharmacognosy, Faculty of Pharmacy, Helwan University, Helwan, Egypt

3. Department of Medicinal Chemistry, Theodor Bilharz Research Institute, Giza, Egypt

4. Cancer Biology Laboratory, Nobel Biotechnology Centre, Department of Biochemistry, National Research Centre, Dokki, Cairo, Egypt

5. Department of Pharmacognosy, Faculty of Pharmacy, Cairo University, Kasr-el-Aini St., 11562 Cairo, Egypt. Fax: +2027426807.

Abstract

Two galloylglucosides, 6-hydroxy-eugenol 4-O-(6′-O-galloyl)-β-D-4C1-glucopyranoside (4) and 3-(4-hydroxy-3-methoxyphenyl)-propane-1,2-diol-2-O-(2′,6′-di-O-galloyl)-β-D-4C1-glucopyranoside (7), and two C-glycosidic tannins, vascalaginone (10) and grandininol (14), together with fourteen known metabolites, gallic acid (1), methyl gallate (2), nilocitin (3), 1-O-galloyl-4,6-(S)-hexahydroxydiphenoyl-(α/β)-d-glucopyranose (5), 4,6-(S)-hexahydroxydiphenoyl-(α/β)-d-glucopyranose (6), 3,4,6-valoneoyl-(α/β)-d-glucopyranose (8), pedunculagin (9), casuariin (11), castalagin (12), vascalagin (13), casuarinin (15), grandinin (16), methyl-flavogallonate (17) and ellagic acid (18), were identified from the leaves of Pimenta dioica (Merr.) L. (Myrtaceae) on the basis of their chemical and physicochemical analysis (UV, HRESI-MS, 1D and 2D NMR). It was found that 9 is the most cytotoxic compound against solid tumour cancer cells, the most potent scavenger against the artificial radical DPPH and physiological radicals including ROO, OH, and O2 -•, and strongly inhibited the NO generation and induced the proliferation of T-lymphocytes and macrophages. On the other hand, 3 was the strongest NO inhibitor and 16 the highest stimulator for the proliferation of T-lymphocytes, while 10 was the most active inducer of macrophage proliferation .

Publisher

Walter de Gruyter GmbH

Subject

General Biochemistry, Genetics and Molecular Biology

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