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Production of sesquiterpene-type phytoalexins by hairy roots of Hyoscyamus albus co-treated with cupper sulfate and methyl jasmonate.
- Source :
-
Chemical & pharmaceutical bulletin [Chem Pharm Bull (Tokyo)] 2010 Jul; Vol. 58 (7), pp. 934-8. - Publication Year :
- 2010
-
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)).
- Subjects :
- Acetates chemistry
Copper Sulfate chemistry
Cyclopentanes chemistry
Hyoscyamus chemistry
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Conformation
Oxylipins chemistry
Plant Roots chemistry
Plant Roots metabolism
Sesquiterpenes isolation & purification
Sesquiterpenes metabolism
Phytoalexins
Acetates pharmacology
Copper Sulfate pharmacology
Cyclopentanes pharmacology
Hyoscyamus metabolism
Oxylipins pharmacology
Sesquiterpenes chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1347-5223
- Volume :
- 58
- Issue :
- 7
- Database :
- MEDLINE
- Journal :
- Chemical & pharmaceutical bulletin
- Publication Type :
- Academic Journal
- Accession number :
- 20606340
- Full Text :
- https://doi.org/10.1248/cpb.58.934