Hydrolyzable tannins of tamaricaceous plants. III.1 Hellinoyl-and macrocyclic-type ellagitannins from Tamarix nilotica

Mohamed A.A. Orabi, Shoko Taniguchi, Morio Yoshimura, Takashi Yoshida, Kaori Kishino, Hiroshi Sakagami, Tsutomu Hatano

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Three new hellinoyl-type ellagitannins, nilotinins M4 (7), D7 (8), and D8 (9), and a new macrocyclic-type, nilotinin D9 (10), together with eight known tannins, hirtellins B (2), C (11), and F (12), isohirtellin C (13), tamarixinin A (3), tellimagrandins I and II, and 1,2,6-tri-O-galloyl-β-d-glucose (14), were isolated from an aqueous acetone extract of Tamarix nilotica dried leaves. Nilotinin M4 (7) is a monomeric tannin possessing a hellinoyl moiety. The structure of 8 demonstrated replacement of one of the HHDP groups at the glucose core O-4/O-6 in ordinary dimeric tannins with a galloyl moiety at O-6. This is a new structural feature among the tamaricaceous ellagitannins. On the basis of the results, reported spectroscopic assignments for 2, 3, and the macrocyclic tannins 11-13 were revised. Unusual shifts in the NMR spectra of these macrocyclic tannins are also discussed in relation to their conformations. Several tannins isolated from T. nilotica were assessed for possible cytotoxic activity against four human tumor cell lines, and nilotinin D8 (9) and hirtellin A (1) showed high cytotoxic effects.

Original languageEnglish
Pages (from-to)870-879
Number of pages10
JournalJournal of Natural Products
Volume73
Issue number5
DOIs
Publication statusPublished - May 28 2010

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Hydrolyzable tannins of tamaricaceous plants. III.<sup>1</sup> Hellinoyl-and macrocyclic-type ellagitannins from Tamarix nilotica'. Together they form a unique fingerprint.

  • Cite this