title: Ent-trachyloban-19-oic acid isolated from Iostephane heterophylla as a promising antibacterial agent against Streptococcus mutans biofilms.
abstract: From the roots of Iostephane heterophylla, six known compounds, namely, ent-trachyloban-19-oic acid (1), the mixture of ent-kaur-16-en-19-oic acid (2) and ent-beyer-15-en-19-oic acid (3), xanthorrhizol (4), 16α-hydroxy-ent-kaurane (5) and 16α-hydroxy-ent-kaur-11-en-19-oic acid (6) were isolated using a bioassay-guided fractionation method. The known compounds (1-6) were identified by comparison of their spectroscopic data with reported values in the literature. In an attempt to increase the resultant antimicrobial activity of 1 and 4, a series of reactions was performed on ent-trachyloban-19-oic acid (1) and xanthorrhizol (4), to obtain derivatives 1a, 1b, and 4a-4d. All the isolated compounds (1-6) and the derivatives 1a, 1b, and 4a-4d were evaluated for their antimicrobial activity against two oral pathogens, Streptococcus mutans and Porphyromonas gingivalis associated with caries and periodontal disease, respectively. Compounds 1, 1b, 2+3, 4 and 4d inhibited the growth of S. mutans with concentrations ranging from 4.1 μg/mL to 70.5 μg/mL. No significant activity was found on P. gingivalis except for 4 with an MIC of 6.8 μg/mL. The ability of 1, 1b, 2+3, 4 and 4d to inhibit biofilm formation by S. mutans was evaluated. It was found that 1, 1b, 4 and 4d interfered with the establishment of S. mutans biofilms, inhibiting their development at 32.5, 125.0, 14.1 and 24.4 μg/mL, respectively.
authors.affiliation: Departamento de Farmacia, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 D.F., Mexico.
authors.forename: Dulce M
authors.initials: DM
authors.lastname: Hernández
authors.forename: Gloria
authors.initials: G
authors.lastname: Díaz-Ruiz
authors.forename: Blanca E
authors.initials: BE
authors.lastname: Rivero-Cruz
authors.forename: Robert A
authors.initials: RA
authors.lastname: Bye
authors.forename: María Isabel
authors.initials: MI
authors.lastname: Aguilar
authors.forename: J Fausto
authors.initials: JF
authors.lastname: Rivero-Cruz
mesh_terms: D000900:Anti-Bacterial Agents / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D019659:Asteraceae / Q000737:chemistry*; D018441:Biofilms / Q000187:drug effects*; D003731:Dental Caries / Q000188:drug therapy / Q000382:microbiology; D004224:Diterpenes / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D045786:Diterpenes, Kaurane / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use; D010510:Periodontal Diseases / Q000188:drug therapy / Q000382:microbiology; D010636:Phenols / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D018517:Plant Roots / Q000737:chemistry; D016966:Porphyromonas gingivalis / Q000187:drug effects; D013295:Streptococcus mutans / Q000187:drug effects*
chemical_list: D000900:Anti-Bacterial Agents; D004224:Diterpenes; D045786:Diterpenes, Kaurane; D010636:Phenols; D010936:Plant Extracts; C458719:beyerenoic acid; C120248:xanthorrhizol; C039978:trachyloban-19-oic acid