Methyl β-Orcinolcarboxylate and Atranol from the Lichen Stereocaulon vesuvianum

Abstract

Extracts of Stereocaulon vesuvianum Pets, showed strong activity against Bacillus subtilis and Escherichia coli and a distinct activity against Penicillium digitatum and Saccharomyces cerevisiae. By preparative hplc, methyl ß-orcinolcarboxylate (strongly antifungal) and atranol (strongly antibacterial) were isolated, and it was shown that both compounds are present as natural products and are not artifacts formed during workup. Methyl ß-orcinolcarboxylate was recently suggested to be present in S. vesuvianum by the revision (1) of an isomeric structure previously reported (2) in this species. Sizable amounts of the common cortical depside atranorin (inactive) were also isolated. EXPERIMENTALPlant material.-S. vesuvianum was collected on the middle slopes (ca. 1300 m) of Mt. Etna. It grows abundantly only on the ancient (2-3 centuries old) lava flows. A voucher specimen is deposited at the University of Catania.

The Antibacterial Activity of Compounds Isolated from Oakmoss against <i>Legionella pneumophila</i> and Other <i>Legionella</i> spp.

“…extracts have been identified previously, including atranol (compound 3), chloroatranol (compound 19), atraric acid (compound 7), everninate (compound 11), haematommate (compound 13), orsellinates (compounds 4, 6, 8) and lecanorin (compound 5). [1][2][3][4] The antimicrobial activity of these compounds against various fungi and Gram-positive and Gram-negative bacteria has also been demonstrated in previous reports. 13,14) However, an examination of the antibacterial activity of these oakmoss components against L. pneumophila and Legionella spp.…”

“…3,4) However, to date there have been no reports concerning the antibacterial activity of these components against Legionella pneumophila strains. We previously demonstrated that 101 natural and synthetic fragrance ingredients exhibit antimicrobial activity against representative Gram-positive and Gram-negative bacteria, as well as various fungi.…”

Novel Abietane Diterpenoids and Aromatic Compounds from Cladonia rangiferina and Their Antimicrobial Activity against Antibiotics Resistant Bacteria

“…In our investigation, two new abietane diterpenoids, called hanagokenols A (1), and B (2), along with 15 known compounds including abietane, [3][4][5] labdane, [6][7][8] isopimarane 9) diterpenoids, monocyclic aromatic compound, 10,11) depside, 12,13) and dibenzofuran 14,15) were isolated from C. rangiferina. We describe here the isolation, purification, and structural elucidation of the unique abietane diterpenes, 1 and 2, primarily by extensive NMR experiments, and the antimicrobial activities of all the isolated compounds against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococci (VRE).…”

“…The AcOEt extract was fractionated into seven fractions by column chromatography (silica gel), followed by repeated separations of their seven portions by chromatography over silica gel. Reversed-phase silica gel furnished hanagokenols A (1), and B (2), obtuanhydride (3), 3) sugiol (4), 4) 5,6-dehydrosugiol(5), 4) montbretol (6), 5) cis-communic acid (7), 6) imbricatoloic acid (8), 7) 15-acetylimbricatoloic acid (9), 8) junicedric acid (10), 8) 7a-hydroxysandaracopimaric acid (11), 9) b-resorylic acid (12), 10) atranol (13), 11) barbatic acid (14), 12) homosekikaic acid (15), 13) didymic acid (16), 14) and condidymic acid (17 . These data suggested that 1 was an abietane-type diterpene, as compounds 3-6.…”

Chemistry and Bioactivity of Physciaceae LichensPyxine consocians. andHeterodermia leucomelos.

“…Atranorin (2): Colorless needles (CH 2 Cl 2 ) (Brassy et al, 1982). Methyl-b-orcinolcarboxylate (3): Colorless small needles (CH 2 Cl 2 ) (Caccamese et al, 1986). Zeorin (4): Colorless needles (CH 2 Cl 2 ) (Yosioka et al, 1972).…”