Plant antimutagenic agents, 4. Isolation and structure elucidation of maesol, an inactive constituent of Maesa spp.
Maesol, a novel dimeric phenol, was isolated from seeds of Maesa montana and Maesa indica. Maesol was shown to have the formula C28H42O4 with structure 1, a dimeric, symmetrical 1,12-bis(3,3'-dihydroxy-4,4'-dimethyl-5,5'-dimethoxyphenyl)dodecane. It is the first compound with such structure to be isolated from plant material. Structure elucidation was based largely on 1H- and 13C-nmr techniques and comparison with a known synthetic isomeric dimer 3. Although crude extracts showed strong inhibition of 2-aminoanthracene activity against Salmonella typhimurium (T-98), the pure compound was inactive when tested for inhibition of the mutagenic activity of several mutagens.
Wall
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ME
Research Triangle Institute, Research Triangle Park, North Carolina 27709.
Wani
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MC
Gaetano
K
K
Manikumar
G
G
Taylor
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McGivney
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R
D015073:2-Acetylaminofluorene / Q000037:antagonists & inhibitors; D000873:Anthracenes / Q000037:antagonists & inhibitors; D001564:Benzo(a)pyrene / Q000037:antagonists & inhibitors; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010636:Phenols / Q000302:isolation & purification* / Q000494:pharmacology; D010944:Plants / Q000032:analysis*; D012486:Salmonella typhimurium / Q000187:drug effects
D000873:Anthracenes; D010636:Phenols; C058890:maesol; D001564:Benzo(a)pyrene; C006593:2-anthramine; D015073:2-Acetylaminofluorene