Novel A-seco-rearranged lanostane triterpenoids from Abies sachalinensis.
From the needles of Abies sachalinensis, novel rearranged lanostane type triterpenes, 1-4, were isolated along with a known triterpene (5). The structures of the new compounds, 1-4, were elucidated to be 3,4-seco-8-(14-->13R)abeo-17,13-friedo-9beta-lanosta-4(28),7,14(30),22Z,24-pentaen-26,23-olide-3-oic acid, methyl 3,4-seco-8-(14-->13R)abeo-17,13-friedo-9beta-lanosta-4(28),7,14(30),22Z,24-penten-26,23-olide-3-oate, 3,4-seco-8(14-->13R)abeo-17,13-friedo-9beta-lanosta-4(28),7,14,22Z,24-pentaene-26,23-olide-3-oic acid and methyl 3,4-seco-8(14-->13R)abeo-17,13-friedo-9beta-lanosta-4(28),7,14,22Z,24-pentaene-26,23-olide-3-oate, respectively, by means of spectral experiments, especially two dimensional NMR spectroscopy, such as 1H-detected multiple quantum coherence (HMQC), 1H-detected heteronuclear multiple bond connectivity (HMBC) and 1H-1H-correlation spectroscopy (COSY) experiments. These new compounds have novel structures containing A-seco, rearranged spiro structure and a gamma-lactone conjugated with a diene. Some of these compounds showed potent antibacterial activity against gram positive bacteria.
Kuroyanagi
M
M
School of Bioresources, Hiroshima Pretectural University, Shobara, Japan,. kuroyang@bio.hiroshima-pu.ac.jp
Sugiyama
K
K
Kanazawa
M
M
Kawahara
N
N
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D032462:Cycadopsida / Q000737:chemistry*; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D014315:Triterpenes