TY - JOUR TI - Comparative study of naphthoquinone contents of selected Greek endemic boraginaceae plants - Antimicrobial activities AU - Tufa, T. AU - Damianakos, H. AU - Graikou, K. AU - Chinou, I. JO - Natural Product Communications PY - 2017 VL - 12 TODO - 2 SP - 179-180 PB - Natural Product Incorporation SN - null TODO - 10.1177/1934578x1701200209 TODO - 1,4 naphthoquinone derivative; acetylalkannin; Alkanna sfikasiana extract; alpha methylbutyrylalkannin; amoxicillin; amphotericin; beta hydroxyisovalerylalkannin; beta,beta dimethylacrylalkannin; clavulanic acid; Cynoglossum columnae extract; deoxyalkannin; flucytosine; isobutyrylalkannin; netilmicin; Onosma erecta extract; Onosma graeca extract; Onosma kaheirei extract; plant extract; propionylalkannin; unclassified drug, Alkanna sfikasiana; antimicrobial activity; Boraginaceae; Candida albicans; Candida glabrata; Candida tropicalis; carbon nuclear magnetic resonance; comparative study; Conference Paper; controlled study; Cynoglossum columnae; drug isolation; drug structure; electrospray mass spectrometry; Enterobacter cloacae; Escherichia coli; Greece; Klebsiella pneumoniae; nonhuman; Onosma erecta; Onosma graeca; Onosma kaheirei; plant root; proton nuclear magnetic resonance; Pseudomonas aeruginosa; separation technique; Staphylococcus aureus; Staphylococcus epidermidis TODO - The cyclohexane (Ch) extracts of the roots of five Greek endemic Boraginaceae plants, Onosma kaheirei Teppner, O. Graeca Boiss., O. Erecta Sibth. & Sm., Alkanna sfikasiana Kit Tan, Vold and Strid and Cynoglossum columnae Ten, were investigated for the presence of alkannin/shikonin-related compounds. All species,s except C. Columnae and O. Erecta, were found to contain this type of compounds. Seven compounds were obtained after several chromatographic separations from the Ch extracts of the investigated plants: deoxyalkannin (1), 2''-(S)-α-methylbutyrylalkannin (2), isobutyrylalkannin (3), propionylalkannin (4), acetylalkannin (5), β-hydroxyisovalerylalkannin (6), and β,β-dimethylacrylalkannin (7). All structures were identified by 1D 1H-/13C- and 2D NMR spectroscopy, assisted also by ESI-MS. The extracts and the isolated compounds exhibiting an interesting antimicrobial profile when evaluated for their antimicrobial activity against six Gram-positive and -negative bacteria and three human pathogenic fungi. ER -