Hydrolysable tannins isolated from Syzygium aromaticum

Structure of a new C-Glucosidic ellagitannin and spectral features of tannins with a tergalloyl group

Li Ming Bao, Eerdunbayaer, Akiko Nozaki, Eizo Takahashi, Keinosuke Okamoto, Hideyuki Ito, Tsutomu Hatano

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Eighteen hydrolysable tannins, including a new C-glucosidic tannin named aromatinin A (1), were isolated from an aqueous acetone extract of dried flower buds of Syzygium aromaticum Merr. et Perry. We determined that 1 had a gallic acid C-glucoside structure, based on the spectral data and synthesis from casuarinin (18) and gallic acid (20). This is a rare example of hydrolysable tannins with gallic acid C-glucoside structure. We also report the 1H nuclear magnetic resonance (NMR) spectral features of syzyginin A (2), bicornin (3), and platycaryanin A (4), which were also isolated from S. aromaticum, based on their structures with a tergalloyl group or its depsidone form. The remaining known compounds were identified as alunusnin A (5), rugosin C (6), 1,2,3-tri-O-galloyl-β-D-glucose (7), 1,2,3,6-tetra-O-galloyl-β-D- glucose (8), tellimagrandin II (9), casuarictin (10), heterophylliin D (11), rugosin D (12), rugosin F (13), euprostin A (14), 1,2-di-O-galloyl-3-O- digalloyl-4,6-O-(S)-hexahydroxydiphenoy- β-D-glucose (15), alienanin B (16), squarrosanin A (17), and 18. The antifungal effects of hydrolysable tannins, 9, 12, and 18 against Candida strains are also described.

Original languageEnglish
Pages (from-to)365-381
Number of pages17
JournalHeterocycles
Volume85
Issue number2
DOIs
Publication statusPublished - Jan 30 2012

Fingerprint

Hydrolyzable Tannins
Syzygium
Gallic Acid
Tannins
Glucosides
Glucose
Candida
Acetone
Magnetic Resonance Spectroscopy
Nuclear magnetic resonance
ellagitannin

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

Hydrolysable tannins isolated from Syzygium aromaticum : Structure of a new C-Glucosidic ellagitannin and spectral features of tannins with a tergalloyl group. / Bao, Li Ming; Eerdunbayaer; Nozaki, Akiko; Takahashi, Eizo; Okamoto, Keinosuke; Ito, Hideyuki; Hatano, Tsutomu.

In: Heterocycles, Vol. 85, No. 2, 30.01.2012, p. 365-381.

Research output: Contribution to journalArticle

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