title: Production of sesquiterpene-type phytoalexins by hairy roots of Hyoscyamus albus co-treated with cupper sulfate and methyl jasmonate.
abstract: The production of sesquiterpene-type phytoalexins with a vetispyradiene skeleton by Hyoscyamus albus hairy roots induced by methyl jasmonate (MeJA) was reported in a previous paper. The production pattern on co-treatment with cupper sulfate and MeJA (CuSO(4)-MeJA) showed a TLC profile differing from that on treatment with MeJA. Thus, we studied the production of phytoalexins on hairy root culture involving co-treatment with CuSO(4)-MeJA. In the experiment, many sesquiterpene-type phytoalexins with a vetispyradiene skeleton were isolated, most of which were different from the products reported in the previous paper. Here, we isolated four new phytoalexins (1-4) along with known compounds 5-10 from the culture medium of H. albus hairy roots co-treated with MeJA-CuSO(4). The structures of the new compounds (1-4) were determined as: (3R,4S,5R,7S,9R)-3-acetoxy-9-(2-methylpropionyloxy)solavetivone (1), (3R,4S,5R,7S,9R)-3-hydroxy-9-(3-methylbutanoyloxy)solavetivone (2), (3R,4S,5R,7S,9R)-3-acetoxy-9-(3-methyl-butanoyloxy)solavetivone (3), and (3R,4S,5R,7S,9R)-3-acetoxy-9-(3-methyl-2-butenoyloxy)-solavetivone (4) based on MS and NMR including 2D-NMR data. These findings indicated that the production of phytoalexins in H. albus hairy roots yielded different products based on treatment with different chemicals (CuSO(4), MeJA, and MeJA-CuSO(4)).
authors.affiliation: Department of Life and Environmental Sciences, Prefectural University of Hiroshima, Hiroshima, Japan.
authors.forename: Moriyuki
authors.initials: M
authors.lastname: Kawauchi
authors.forename: Morihiro
authors.initials: M
authors.lastname: Kawauchi
authors.forename: Toshihide
authors.initials: T
authors.lastname: Arima
authors.forename: Osamu
authors.initials: O
authors.lastname: Shirota
authors.forename: Setsuko
authors.initials: S
authors.lastname: Sekita
authors.forename: Takahisa
authors.initials: T
authors.lastname: Nakane
authors.forename: Yoichi
authors.initials: Y
authors.lastname: Takase
authors.forename: Masanori
authors.initials: M
authors.lastname: Kuroyanagi
mesh_terms: D000085:Acetates / Q000737:chemistry / Q000494:pharmacology*; D019327:Copper Sulfate / Q000737:chemistry / Q000494:pharmacology*; D003517:Cyclopentanes / Q000737:chemistry / Q000494:pharmacology*; D032304:Hyoscyamus / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D054883:Oxylipins / Q000737:chemistry / Q000494:pharmacology*; D018517:Plant Roots / Q000737:chemistry / Q000378:metabolism; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D000094162:Phytoalexins
chemical_list: D000085:Acetates; D003517:Cyclopentanes; D054883:Oxylipins; D012717:Sesquiterpenes; C072239:methyl jasmonate; D019327:Copper Sulfate; D000094162:Phytoalexins