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 vetis pyrane skeleton. Lubimin and solavetivone were isolated after treatment wit h Cu2+. Seven sesquiterpenoid phytoalexins were isolated from the culture m edium after treatment with JAMe, including lubimin, solavetivone, 3-hydroxy solavetivone and four new compounds (1-4). Structures of the new compounds were elucidated to be (3R, 4S, 5R, 7S, SR)-3-hydroxy-9-tigloyloxysolavetivo ne (1), (3R,4S, 5R, 7S, SR)-3-hydroxy-9-(3-methylbutenoyloxy)-solavetivone (2), (3R,4S, 5R, 7S,SR)-3-hydroxy-9-isobutanoyloxysolavetivone (3); and (3R ,4S, 5R, 7S,SR)-3,9-dihydroxysolavetivone (4). The induction pattern of phy toalexins in hairy roots treated with JAMe was different in those treated w ith Cu2+, and co-treatment with JAMe and Cu2+ gave only solavetivone.