Phytoalexins from hairy roots of Hyoscyamus albus treated with methyl jasmonate.

The treatment of hairy roots of Hyoscyamus albus with copper sulfate (Cu2+) and methyl jasmonate (JAMe) produced several phytoalexins having the vetispyrane skeleton. Lubimin and solavetivone were isolated after treatment with Cu2+. Seven sesquiterpenoid phytoalexins were isolated from the culture medium after treatment with JAMe, including lubimin, solavetivone, 3-hydroxysolavetivone and four new compounds (1-4). Structures of the new compounds were elucidated to be (3R,4S,5R,7S,9R)-3-hydroxy-9-tigloyloxysolavetivone (1), (3R,4S,5R,7S,9R)-3-hydroxy-9-(3-methylbutenoyloxy)-solavetivone (2), (3R,4S,5R,7S,9R)-3-hydroxy-9-isobutanoyloxysolavetivone (3); and (3R,4S,5R,7S,9R)-3,9-dihydroxysolavetivone (4). The induction pattern of phytoalexins in hairy roots treated with JAMe was different in those treated with Cu2+, and co-treatment with JAMe and Cu2+ gave only solavetivone.