Synthesis, absolute stereochemistry and molecular design of the new antifungal and antibacterial antibiotic produced by Streptomyces sp.201.
The absolute stereochemistry of the new antifungal and antibacterial antibiotic produced by Streptomyces sp.201 has been established by achieving the total synthesis of the product. A series of analogues have also been synthesized by changing the side chain and their bioactivity assessed against different microbial strains. Among them, 1e (R = C8H17) was found to be the most potent with MIC of 8 microg/mL against Mycobacterium tuberculosis, 12 microg/mL against Escherichia coli and 16 microg/mL against Bacillus subtilis 6 microg/mL against Proteus vulgaris. This was followed by 1b (R = C5H11) with MIC of 10-20 microg/mL range and 1d (R = C7H15) with MIC of 14-24 g/mL, whereas 1a (R = C4H9) and 1f (R = C18H35) were found to be completely inactive. Besides, 1c (R = C6H13) showed certain extent of antibacterial activity in the range of 24-50 microg/mL. Mycobacterium tuberculosis was very sensitive to 1e (R = C8H17) with MIC of 8 microg/mL. Antifungal activity of analogues 1d (R = C7H15) and 1e, (R = C8H17) against Fusarium oxysporum and Rhizoctonia solani were found promising with MFCs in the 15-18 microg/mL range.
Boruwa
J
J
Natural Products Chemistry Division, Regional Research Laboratory (CSIR), Jorhat 785006, Assam, India.
Kalita
B
B
Barua
N C
NC
Borah
J C
JC
Mazumder
S
S
Thakur
D
D
Gogoi
D K
DK
Bora
T C
TC
D000900:Anti-Bacterial Agents / Q000096:biosynthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000378:metabolism* / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D005670:Fusarium / Q000187:drug effects; D007539:Isonicotinic Acids / Q000138:chemical synthesis / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D012232:Rhizoctonia / Q000187:drug effects; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry* / Q000378:metabolism; D013329:Structure-Activity Relationship
C467052:2-methylheptyl isonicotinate; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D007539:Isonicotinic Acids