title: Total Synthesis of (±)-Isoperbergins and Correction of the Chemical Structure of Perbergin.
abstract: On the basis of its reported chemical structure, perbergin, a Rhodococcus fascians virulence quencher from the bark of Dalbergia pervillei, and its isomer were synthesized in nine steps with a 13.5% yield. However, the NMR spectra of the synthetic products were inconsistent with those reported in the literature. Re-evaluation of the 1D and 2D NMR spectra of the natural product perbergin revealed that the geranyl moiety of this compound is located at C-6 and has an E-configuration, instead of the reported C-8 geranylation with a Z-configuration. Interestingly, the synthetic isoperbergins demonstrated good antibacterial activity against R. fascians, Mycobacterium smegmatis, and Staphylococcus aureus, but not against the Gram-negative bacteria Pseudomonas aeruginosa and Escherichia coli.
authors: Department of Pharmaceutical Sciences, Oregon State University , Corvallis, Oregon 97331-3507, United States.
authors: Khaled H
authors: KH
authors: Almabruk
authors: Department of Botany and Plant Pathology, Oregon State University , Corvallis, Oregon 97331-2902, United States.
authors: Jeff H
authors: JH
authors: Chang
authors: Department of Pharmaceutical Sciences, Oregon State University , Corvallis, Oregon 97331-3507, United States.
authors: Taifo
authors: T
authors: Mahmud
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D035782:Dalbergia / Q000737:chemistry; D004926:Escherichia coli / Q000187:drug effects; D006090:Gram-Negative Bacteria / Q000187:drug effects; D007529:Isoflavones / Q000138:chemical synthesis* / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D012240:Rhodococcus / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects
chemical_list: C560203:3-(2,3-dihydroxy-4-methoxyphenyl)-8-(3,7-dimethylocta-2,6-dienyl)-5,7-dihydroxy-2,3-dihydrochromen-4-one; D000900:Anti-Bacterial Agents; D007529:Isoflavones; D039821:Monoterpenes