Autotoxicity and Allelopathy of 3,4-Dihydroxyacetophenone Isolated from Picea schrenkiana Needles

Abstract

Bioassay-guided fractionation of the diethyl ether fraction of a water extract of Picea schrenkiana needles led to the isolation of the phenolic compound 3,4-dihydroxy- acetophenone (DHAP). The allelopathic effects of DHAP were evaluated under laboratory conditions on P. schrenkiana, rice (Oryza sativa L.), wheat (Triticum aestivum L.), radish (Raphanus sativus L.), lettuce (Latuca sativa L.), cucumber (Cucumis sativus L.) and mung bean (Phaseolus radiatus L.). DHAP significantly inhibited seed germination and seedling growth of P. schrenkiana at concentrations of 2.5 mM and 0.5 mM (p < 0.05). Soil analysis revealed that P. schrenkiana forest soils contained exceptionally high DHAP concentrations (mean = 0.51 ± 0.03 mg/g dry soil), sufficient to inhibit natural P. schrenkiana recruitment. DHAP also exhibited strong allelopathic potential. It significantly inhibited wheat and lettuce seed germination at concentrations of 1 mM and 0.5 mM (p < 0.05). The active compound also completely inhibited root growth of the six test species at high concentrations. Our results suggest a dual role of DHAP, both as an allelochemical and as an autotoxicant. The potential for a single plant needle-leached compound to influence both inter- and intra-specific interactions emphasized the complex effects that plant secondary metabolites might have on plant population and community structure.

Physiological effects of autotoxicity due to DHAP stress on Picea schrenkiana regeneration

“…Schrenkiana , so it was hypothesized that 0.25 mM DHAP might be the inflection point of changing action direction. It was near to the concentration of 0.224 mM in natural forest conditions [32]. Thus, our investigation provided evidence on the phytotoxic potential of P .…”

A new phenolic compound with antioxidant activity from the branches and leaves of Pyrus pashia

“…Compound 1 (7) (Machida & Kikuchi, 1993), p-hydroxyphenyl 6-O-cis-p-Coumaroyl-b-D-glucopyranoside (8) (Machida & Kikuchi, 1993), 4-hydroxybenzoic acid (9) (Rukachaisirikul et al 2010), 4-(methoxymethyl) phenyl-1-Ob-D-glucopyranoside (10) , 3,4-dihydroxyacetophenone (11) (Ruan et al 2011), 3,4-dihytroxy benzaldehyde (12) , p-hytroxy benzaldehyde (13) (Yang et al 2013 ), 3-O-(b-D-glucopyranosyl)-1-(3 0 5 0 -dimethoxy-4-hydroxyphenyl-1-propanone (21) , myzodendrone (22) (Desmarchelier et al 2005) were identified by comparisons with spectroscopic data of literatures.…”

Effects of climate warming on plant autotoxicity in forest evolution: a case simulation analysis for Picea schrenkiana regeneration

“…In natural forest conditions, one gram of dry soil from a mature P. Schrenkiana forest was determined to contain 0.51 ± 0.03 mg DHAP (Ruan et al. 2011). If DHAP in 1 g field soil was dissolved into 15 mL snow or rain water, the concentration of DHAP would be 0.224 mmol/L which was near to the concentration of inflection point.…”

“…The phenolic compound 3,4‐dihydroxy‐acetophenone (DHAP) isolated by bioassay‐guided fractionation from the diethyl ether fraction was proved to be the major autotoxic chemical in P. Schrenkiana needles (Ruan et al. 2011). …”