Benzoquinone, the substance essential for antibacterial activity in aqueous extracts from succulent young shoots of the pear Pyrus spp.
Aqueous extracts of the tissue of succulent young shoots of the pear Pyrus spp. exhibited strong antibacterial activity against the bacterium Erwinia amylovora bv. 4. This activity was investigated quantitatively by a newly developed bioassay method. It was found that the activity changed with the age of the tissue. Extracts of the youngest leaves and stems from the shoot tops showed the strongest activity, and the activity decreased with age of the leaves and stems. The activity also changed with increase in time after preparation of the extract, increasing rapidly in the first hour after preparation, reaching a maximum at about 4 h, and then decreasing slowly. The substance essential for the antibacterial activity was isolated from the extract by steam distillation in vacuo and through charcoal powder column chromatography. It was identified as benzoquinone (2,5-cyclohexadiene-1,4-dione) by NMR-spectra, mass spectra and HPLC analysis. The phenolic metabolism from arbutin to hydroquinone and then to benzoquinone in the aqueous extracts was analyzed quantitatively by HPLC. The changes in the contents of benzoquinone in the extracts of leaves and stems with tissue aging and with increase in time after preparation of the extracts paralleled the changes in antibacterial activity as determined by the quantitative bioassay.
Jin
Shigeki
S
National Agricultural Research Center for Hokkaido Region, Toyohira-ku, Sapporo 062-8555, Japan. sjin@naro.affrc.go.jp
Sato
Norio
N
D000375:Aging / Q000502:physiology; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D016227:Benzoquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D006873:Hydroquinones / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry* / Q000494:pharmacology; D018520:Plant Shoots / Q000737:chemistry* / Q000502:physiology; D031989:Pyrus / Q000737:chemistry* / Q000502:physiology; D013997:Time Factors; D014867:Water
D000900:Anti-Bacterial Agents; D016227:Benzoquinones; D006873:Hydroquinones; D010936:Plant Extracts; D014867:Water; C004532:quinone; C031927:hydroquinone