Isoterchebulin and 4,6-O-isoterchebuloyl-D-glucose, novel hydrolyzable tannins from Terminalia macroptera.
Two new hydrolyzable tannins, isoterchebulin (1) and 4,6-O-isoterchebuloyl-D-glucose (2), together with six known tannins, 3-8, were isolated from the bark of Terminalia macroptera. Their structures were elucidated by extensive 1D and 2D NMR studies, MS, and chemical transformations. Biological activities of all compounds were evaluated against the snail Biomphalaria glabrata, the bacteria Bacillus subtilis and Pseudomonas fluorescens, the nematode Caenorhabditis elegans, and four cancer cell lines (Hep G2, MCF-7/S, MDA-MB-231, and 5637 cells). All compounds except 3 showed antimicrobial activities against B. subtilis (MIC 8-64 microg/mL), whereas only 1 was active against C. elegans (100 microg/mL) and B. glabrata(LC(100) = 60 microg/mL). 3 and 8 were toxic against 5637 cells with LC(50) = 84.66 and 41.40 microM, respectively.
Institut für Chemie, Universität Hohenheim, Garbenstrasse 30, D-70599 Stuttgart, Germany,
J
J
Conrad
B
B
Vogler
S
S
Reeb
I
I
Klaiber
S
S
Papajewski
G
G
Roos
E
E
Vasquez
M C
MC
Setzer
W
W
Kraus
D000349:Africa; D000818:Animals; D000871:Anthelmintics / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D001700:Biomphalaria / Q000187:drug effects; D017173:Caenorhabditis elegans / Q000187:drug effects; D005947:Glucose / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D047348:Hydrolyzable Tannins; D009682:Magnetic Resonance Spectroscopy; D008975:Molluscacides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D011551:Pseudomonas fluorescens / Q000187:drug effects; D013634:Tannins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D017210:Tilapia; D014197:Trees / Q000737:chemistry*
C429211:4,6-O-isoterchebuloylglucose; D000871:Anthelmintics; D000900:Anti-Bacterial Agents; D000972:Antineoplastic Agents, Phytogenic; D047348:Hydrolyzable Tannins; D008975:Molluscacides; D013634:Tannins; C429210:isoterchebulin; D005947:Glucose