Antimicrobial activities of the bromophenols from the red alga Odonthalia corymbifera and some synthetic derivatives.
A series of bromophenols was obtained by isolation from red alga Odonthalia corymbifera and by reactions of bis(hydroxyphenyl)methanes with bromine. New bromophenols including 3,3',5,5'-tetrabromo-2,2',4,4'-tetrahydroxydiphenylmethane (10), a regioisomer of the potent antimicrobial natural product, together with known derivatives were synthesized in high yield. All of the isolated and synthesized compounds were tested for antimicrobial activity against gram-negative, gram-positive bacteria and fungi. The preliminary structure-activity relationship, to elucidate the essential structure requirements for antimicrobial activity, has been described. Among the isolated natural products 2,2',3,3'-tetrabromo-4,4',5,5'-tetrahydroxydiphenylmethane (4) was found to be the most active derivative against Candida albicans, Aspergillus fumigatus, Trichophyton rubrum, and Trichophyton mentagrophytes. The synthetic bromophenols 3,3'-dibromo-6,6'-dihydroxydiphenylmethane (13) and 3,3',5,5'-tetrabromo-6,6'-dihydroxydiphenylmethane (14) showed potent antibacterial effect against Staphylococcus aureus, Bacillus subtilis, Micrococcus luteus, Proteus vulgaris, and Salmonella typhimurium.
Department of Agricultural Biotechnology, Seoul National University, Seoul 151-921, Republic of Korea.
Ki-Bong
KB
Oh
Ji Hye
JH
Lee
Soon-Chun
SC
Chung
Jongheon
J
Shin
Hee Jae
HJ
Shin
Hye-Kyeong
HK
Kim
Hyi-Seung
HS
Lee
D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001969:Bromobenzenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000461:Rhodophyta / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000890:Anti-Infective Agents; D001969:Bromobenzenes; D010636:Phenols