(22S)-6-O-acetyl-21betaH-hopane-3beta,6beta,22,29-tetrol from oakmoss (Evernia prunastri).
A novel hopanoid triterpene, (22S)-6-O-acetyl-21betaH-hopane-3beta,6beta,22,29-tetraol, was isolated from oakmoss (Evernia prunastri (L.) Ach.), as identified from 1H, 13C, DEPT, COSY, NOESY, HSQC and HMBC NMR, MS and IR spectroscopy. During recrystallisation a new compound, 30-nor-6-O-acetyl-3beta,6beta-dihydroxy-21alphaH-hopan-22-one, was formed by a formal loss of methanol from the dihydroxypropyl moiety. No biological activity was found for the naturally occurring compound upon testing against a series of fish and human pathogenic bacteria.
Lutnaes
Bjart Frode
BF
Department of Chemistry, Norwegian University of Science and Technology (NTNU), NO-7491 Trondheim, Norway.
Bruun
Torger
T
Kjøsen
Helge
H
D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology*; D004926:Escherichia coli / Q000187:drug effects; D005399:Fishes / Q000382:microbiology; D006801:Humans; D008826:Microbial Sensitivity Tests; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D012116:Resins, Plant; D013211:Staphylococcus aureus / Q000187:drug effects; D013729:Terpenes; D014315:Triterpenes / Q000737:chemistry / Q000494:pharmacology*; D014733:Vibrio / Q000187:drug effects
C489880:6-O-acetyl-21H-hopane-3,6,22,29-tetrol; D000900:Anti-Bacterial Agents; D010936:Plant Extracts; D012116:Resins, Plant; D013729:Terpenes; D014315:Triterpenes; C044724:oakmoss