Geranylgeraniol-type diterpenoids, boletinins A-J, from Boletinus cavipes as inhibitors of superoxide anion generation in macrophage cells.
In addition to16-hydroxygeranylgeraniol (1) and cavipetin B (2), 10 new geranylgeraniol-type diterpenoids, named boletinins A-J (3-12), were isolated from the fruiting bodies of Boletinus cavipes. Compounds 1-9 and 11 exhibited inhibitory activities of less than 10% at 25-125 microM in the xanthine oxidase test. A bioassay on superoxide anion (O2*-) generation in macrophage cells revealed that 1 and 4-12 suppressed the generation by more than 20% at 25 microM. Compounds 4 and 5 showed inhibitory activities against O2*- generation of more than 50% at 50 microM and exhibited no or low cytotoxicities against macrophage cells at 25-50 microM, suggesting that 4 and 5 are the most promising candidates for O2*- generation inhibitors. O-Acyl geranylgeraniol derivatives, 2 and 7-12, showed cytotoxicities at 25 microM.
Kamo
Tsunashi
T
Department of Bioscience and Biotechnology, Faculty of Agriculture, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano 399-4598, Japan. kamo274@gipmc.shinshu-u.ac.jp
Sato
Kazuya
K
Sen
Kikuo
K
Shibata
Hisao
H
Hirota
Mitsuru
M
D000363:Agaricales / Q000737:chemistry*; D000818:Animals; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005260:Female; D007564:Japan; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013481:Superoxides / Q000037:antagonists & inhibitors* / Q000378:metabolism
C487915:16-hydroxygeranylgeraniol; D004224:Diterpenes; C487916:cavipetin B; D013481:Superoxides; C017338:geranylgeraniol