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.
Kuroyanagi
M
M
School of Bioresources, Hiroshima Prefectural University, 562, Nanatsukacyo, Syobara-shi, Hiroshima, 727-0023, Japan.
Arakawa
T
T
Mikami
Y
Y
Yoshida
K
K
Kawahar
N
N
Hayashi
T
T
Ishimaru
H
H
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000302:isolation & purification* / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D005658:Fungi / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D018517:Plant Roots / Q000737:chemistry*; D010944:Plants / Q000737:chemistry*; D012717:Sesquiterpenes / Q000302:isolation & purification / Q000494:pharmacology*; D013056:Spectrophotometry, Ultraviolet
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000972:Antineoplastic Agents, Phytogenic; D012717:Sesquiterpenes