2012/01/01 by Tsutomu Hatano, Eerdunbayaer Eerdunbayaer, Akiko Nozaki +4 · 1 citation
Biochemistry, Genetics and Molecular Biology · Chemistry · Immunology and Microbiology · Medicine · #Antioxidant #Chemistry #Ellagitannin #Food science #Gallic acid #Glucoside #Natural product bioactivities and synthesis #Organic chemistry #Phytochemicals and Antioxidant Activities #Polyphenol #Proanthocyanidin #Stereochemistry #Syzygium #Tannin #Tannin, Tannase and Anticancer Activities #Traditional medicine
paper · pdf · doi:10.3987/com-11-12392
openalex publication_date 2012/01/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/04
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 1 H 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--D-glucose (7), 1,2,3,6-tetra-O-galloyl--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)-hexa- hydroxydiphenoy--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.