Inhibitory activity for chitin synthase II from Saccharomyces cerevisiae by tannins and related compounds.
In the course of search for potent inhibitors of chitin synthase II from natural resources, seven tannins and related compounds were isolated from the aerial part of Euphorbia pekinensis and identified as gallic acid (1), methyl gallate (2), 3-O-galloyl-(-)-shikimic acid (3), corilagin (4), geraniin (5), quercetin-3-O-(2"-O-galloyl)-beta-D-glucoside (6), and kaempferol-3-O-(2"-O-galloyl)-beta-D-glucoside (7). These and nine related compounds, (-)-quinic acid (8), (-)-shikimic acid (9), ellagic acid (10), kaempferol (11), quercetin (12), quercitrin (13), rutin (14), quercetin-3-O-(2"-O-galloyl)-beta-D-rutinoside (15) and 1,3,4,6-tetra-O-galloyl-beta-D-glucose (16), were evaluated for the inhibitory activity against chitin synthase II and III. They inhibited chitin synthase II with IC(50) values of 18-206 microM, except for two organic acids, (-)-quinic acid (8) and (-)-shikimic acid (9). Among them, 3-O-galloyl-(-)-shikimic acid (3) was the most potent inhibitor against chitin synthase II of Saccharomyces cerevisiae with an IC(50) value of 18 microM. The inhibition appears to be selective for chitin synthase II, as they did not appreciably inhibit chitin synthase III.
Hwang
E I
EI
Antibiotics Research Laboratory, Korea Research Institute of Bioscience and Biotechnology, Yusung, Taejon, Korea.
Ahn
B T
BT
Lee
H B
HB
Kim
Y K
YK
Lee
K S
KS
Bok
S H
SH
Kim
Y T
YT
Kim
S U
SU
D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002240:Carbohydrate Sequence; D002687:Chitin Synthase / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D019665:Euphorbiaceae / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry; D012441:Saccharomyces cerevisiae / Q000201:enzymology*; D013634:Tannins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*
D000935:Antifungal Agents; D004791:Enzyme Inhibitors; D010936:Plant Extracts; D013634:Tannins; D002687:Chitin Synthase