title: Hydrolyzable Tannins of Tamaricaceous Plants. 7.1 Structures and Cytotoxic Properties of Oligomeric Ellagitannins from Leaves of Tamarix nilotica and Cultured Tissues of Tamarix tetrandra.
abstract: Partially unacylated new oligomeric hydrolyzable tannins, nilotinin T2 (1, trimer) and nilotinin Q1 (2, tetramer), together with four known trimers, nilotinin T1 (3) and hirtellins T1-T3 (4-6), and a dimer, tamarixinin B (7), were isolated from the aqueous acetone extracts of leaves of Tamarix nilotica. Among them, the new trimer 1 and the known trimers 4 and 6, in addition to the partially unacylated new trimer nilotinin T3 (8), the known dimers nilotinin D3 (9) and tamarixinin C (10), and the monomer tellimagrandin I (11), were isolated from the cultured shoots of Tamarix tetrandra. The structures of the new hydrolyzable tannins were established by chromatographic analyses and extensive 1D and 2D NMR, HRESI-TOFMS, and ECD spectroscopic experiments. Among the new oligomeric tannins, the particular unacylated position of a glucose core is attributed to a possible biosynthetic route. Isolation of the same oligomeric tannins from cultured shoots of T. tetrandra emphasizes the unique biogenetic ability of the obtained cultures on production of the structurally and biologically characteristic tamaricaceous tannins commonly produced by the intact Tamarix plants. Additionally, tannins obtained in the present study together with gemin D (12) and 1,3-di-O-galloyl-4,6-O-(aS)-hexahydroxydiphenoyl-β-d-glucose (13), from our previous investigation of the leaves of T. nilotica, exhibited variable tumor-specific cytotoxic effects. The ellagitannin trimers 4, 6, and 8 and the dimer 9 exerted predominant tumor-selective cytotoxic effects with high specificity toward human promyelocytic leukemia cells.
authors.affiliation: Faculty of Pharmacy, Al-Azhar University , Assiut 71524, Egypt.
authors.forename: Mohamed A A
authors.initials: MA
authors.lastname: Orabi
authors.affiliation: Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University , Tsushima, Okayama 700-8530, Japan.
authors.forename: Shoko
authors.initials: S
authors.lastname: Taniguchi
authors.affiliation: Division of Pharmacology, Department of Diagnostic and Therapeutic Sciences, Meikai University, School of Dentistry , Sakado, Saitama 350-0283, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Sakagami
authors.affiliation: College of Pharmaceutical Sciences, Matsuyama University , Bunkyo-cho, Matsuyama 790-8578, Japan.
authors.forename: Morio
authors.initials: M
authors.lastname: Yoshimura
authors.affiliation: College of Pharmaceutical Sciences, Matsuyama University , Bunkyo-cho, Matsuyama 790-8578, Japan.
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Amakura
authors.affiliation: Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University , Tsushima, Okayama 700-8530, Japan.
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Hatano
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004534:Egypt; D005707:Gallic Acid / Q000031:analogs & derivatives; D005947:Glucose / Q000032:analysis; D005960:Glucosides; D006801:Humans; D047348:Hydrolyzable Tannins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015473:Leukemia, Promyelocytic, Acute / Q000188:drug therapy; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D032363:Tamaricaceae / Q000737:chemistry*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D005960:Glucosides; D047348:Hydrolyzable Tannins; C013515:ellagitannin; D005707:Gallic Acid; C087926:tellimagrandin I; D005947:Glucose