A potent allelopathic substance in cucumber plants and allelopathy of cucumber

A potent growth inhibitory substance was isolated from an aqueous methanol extract of cucumber (Cucumis sativus L. cv. Phung Tuong) plants and determined as (2S)-2,3-dihydro-2??-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-(1,2,3-trihydroxypropyl)benzofuran-3??-methanol (sisymbrifolin) by spectral data. Sisymbrifolin inhibited the growth of cress (Lepidium sativum) and Echinochloa crus-galli seedlings at concentrations greater than 3???M. Concentration of sisymbrifolin in the cucumber plants was the greatest among four growth inhibitory substances, (S)-2-benzoyloxy-3-phenyl-1-propanol, 9-hydroxy-4,7-megastigmadien-9-one, (6S,7E,9S)-6,9,10-trihydroxy-4,7-megastigmadien-3-one, and sisymbrifolin found in the cucumber, whereas growth inhibitory activity of 9-hydroxy-4,7-megastigmadien-9-one against cress and E. crus-galli was the greatest. Total activities of these substances (concentration of the substance/concentration required 50?% growth inhibition) were 14.4, 13.2, 8.5 and 10.7 for (S)-2-benzoyloxy-3-phenyl-1-propanol, 9-hydroxy-4,7-megastigmadien-9-one, (6S,7E,9S)-6,9,10-trihydroxy-4,7-megastigmadien-3-one and sisymbrifolin, respectively. These total activities were about 100-fold greater than those of phenolic acids, which are often mentioned as putative allelochemicals of plants. Thus, these substances may play important roles in the allelopathy of cucumber plants through the growth inhibition of neighboring plant species.     

Effects of lemon balm (Melissa officinalis L.) extract on germination and seedling growth of six plants

The n-hexane-, acetone- and water-soluble fractions obtained from an aqueous acetone extract of lemon balm (Melissa officinalis L.) shoots inhibited the germination and the growth of roots and shoots of cockscomb (Amaranthus caudatus L.), cress (Lepidium sativum L.), crabgrass (Digitaria sanguinalis L.), timothy (Phleum pratense L.), lettuce (Lactuca sativa L.) and ryegrass (Lolium multiflorum Lam.). The inhibitory activity of the water-soluble fraction was the greatest, followed by that of acetone- and n-hexane-soluble fractions in all bioassays. The effectiveness of these fractions on the roots was greater than that of the shoots of the test plants. Significant reductions in the germination and growth of the roots and shoots were observed as the extract concentration increased. Such rate-dependent responses of the test plants to the fractions suggest that each fraction might contain allelochemical(s), but that the greatest potential was in the water-soluble fraction.     

Isolation and identification of a potent allelopathic substance in Bangladesh rice

Aqueous methanol extracts of Bangladesh rice (Oryza sativa L. cv. BR17) inhibited the growth of roots and shoots of cress (Lepidium sativum), lettuce (Lactuca sativa), alfalfa (Medicago sativa), timothy (Phleum pratense), Digitaria sanguinalis, Echinochloa crus-galli and Echinochloa colonum. Increasing the extract concentration increased the inhibition, suggesting that the BR17 may have growth inhibitory substances and possess allelopathic potential. The aqueous methanol extract of the BR17 was purified and a main inhibitory substance was isolated and determined by spectral data as 2,9-dihydroxy-4-megastigmen-3-one. This substance inhibited root and shoot growth of cress and E. crus-galli seedlings at concentrations greater than 0.03 and 3 μM, respectively. The concentrations required for 50% growth inhibition on cress roots and shoots were 0.22 and 0.47 μM, respectively, and on E. crus-galli roots and shoots were 36 and 133 μM, respectively. These results suggest that 2,9-dihydroxy-4-megastigmen-3-one may contribute to the growth inhibitory effect of BR17 and may play an important role in the allelopathy of BR17. Thus, Bangladesh rice BR17 may be potentially useful for weed management in a field setting. An erratum to this article can be found at     

A novel allelopathic substance, 13-epi-orthosiphol N,in Orthosiphon stamineus

Orthosiphon stamineus (Java tea) has been widely used as traditional herb and several bioactive compounds against animal cells have been isolated. However, no bioactive compound against plants has been reported. Therefore, we investigated possible allelopathic properties and substances in O. stamineus. Aqueous methanol extracts of O. stamineus inhibited root and hypocotyl growth of cress (Lepidium sativum) and lettuce (Lactuca sativa) seedlings. Increasing the extract concentration increased the inhibition, which suggests that O. stamineus may have allelopathic properties. When the extract was divided into an ethyl acetate and an aqueous fraction, the ethyl acetate fraction showed the stronger inhibitory effect. Thus, the ethyl acetate phase was further purified, and the main allelopathic substance was isolated and identified as 13-epi-orthosiphol N, a novel compound, by spectral data. 13-epi-Orthosiphol N inhibited root and hypocotyl growth of cress and lettuce at concentrations greater than 10 μmol/L. The concentrations required for 50% inhibition ranged from 41 to 102 μmol/L. These results suggest that 13-epi-orthosiphol N may be an allelochemical and main contributor to the growth inhibitory effect of O. stamineus and may have potential as a template for the development of new plant control substances.     

Isolation and identification of a plant growth inhibitor from Tinospora tuberculata Beumee

Tinospora tuberculata Beumee has been used widely as a folk medicine and several bioactive compounds have been isolated. However, no herbicidal compound has been reported in this species. Therefore, we investigated the presence of phytotoxins in T. tuberculata. The aqueous methanol extracts of T. tuberculata inhibited the growth of roots and shoots of cress (Lepidum sativum L.), lettuce (Lactuca sativa L.), timothy (Phleum pratense L.) and barnyard grass (Echinochloa crus-galli (L.) Beauv.). The extract was then purified by several chromatographic runs with monitoring the inhibitory activity and the main phytotoxic substance was isolated. The chemical structure of the compound was determined by spectral data as syringin (4-[(1E)-3-Hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenyl β-d-glucopyranoside). It inhibited the root and shoot growth of all test plant species at concentrations >10 µM. The concentrations required for 50 % inhibition of root and shoot growth of cress and lettuce ranged from 78.2 to 412 μM, and that of timothy and barnyard grass renged from 9.8 to 73.2 µM. Effectiveness of syringin on monocotyledonous (timothy and barnyard grass) plants was greater than that on dicotyledonous (cress and lettuce) plants. These results suggest that syringin may contribute to the allelopathic effect caused by the T. tuberculata extract.     

Assessment of Allelopathic Potential of Root Exudate of Rice Seedlings

To determine the allelopathic potential of root exudate from early developmental stage of rice (Oryza sativa L), 6-d-old seedlings of eight cultivars were grown with 3-d-old alfalfa (Medicago sativa L.), cress (Lepidium sativum L.) or lettuce (Lactuca sativa L.) seedlings in Petri dishes under controlled condition. All rice cultivars (cv. Norin 8, Kamenoo, Nipponbare, Kinuhikari, Koshihikari, Sasanishiki, Yukihikari and Hinohikari) inhibited growth of roots, shoots and fresh mass of alfalfa, cress and lettuce seedlings. Effectiveness of cv. Koshihikari was the greatest and more than 60% inhibition was recorded in all bioassays, followed by that of cv. Norin 8 of which effectiveness was more than 40%.     

外来入侵植物小飞蓬化感物质的释放途径

在室内以滤纸为载体用离体生测方法测定了小飞蓬(Conyza canadesiL.)全株水浸提物、茎叶淋溶物、根系分泌物及残体土壤分解物对萝卜(Raphanussativus L.)、黄瓜(Cucumis sativus L.)、马唐(Digitarias anguinalis(L.)Scop.)油菜(Brassica campestris L.)和小麦(Triticuma estivum L.)的化感效应,同时在温室内以土壤为载体通过盆栽植物浇灌的方法测定了小飞蓬茎叶淋溶物和根系分泌物对盆栽植物生长的影响。室内生测实验结果表明,小飞蓬全株水浸提物对5种受体种子的萌发和幼苗生长均有较强的抑制作用;根系分泌物、茎叶淋溶物和残体土壤分解物对受体种子的生长抑制作用不同,根系分泌物的活性高于茎叶淋溶物和残体土壤分解物。温室盆栽实验结果也表明,小飞蓬根系分泌物对受体生长的影响高于茎叶淋溶物。这些结果说明根系分泌是小飞蓬化感物质释放的主要途径之一。     

Inhibition of germination and α-amylase induction by 6-methoxy-2-benzoxazolinone in twelve plant species

6-Methoxy-2-benzoxazolinone (MBOA) inhibited germination of rice (Oryza sativa L.), wheat (Triticum aethiopicum Jakubz), rye (Secale cereale L.), onion (Allium cepa L.), wild oat (Avena fatua L.), barnyard grass [Echinochloa crus-galli (L.) Beauv.], ryegrass (Lolium rigidum Gaudin), cress (Lepidium sativum L.), lettuce (Lactuca sativa L.), tomato (Lycopersicum esculentum Mill.), carrot (Daucus carota L.) and amaranth (Amaranthus retroflexus L) and the inhibition increased with increasing MBOA concentrations. MBOA also inhibited the induction of α-amylase in these plant seeds and the inhibition increased with increasing MBOA concentrations. There were variations in sensitivity of these plant species to MBOA, and species of family Poaceae (barnyard grass, wild oat, rice, rye, ryegrass, and wheat) were less sensitive to MBOA than the other plant species.     

Growth inhibitory activity of ABA-β-<Emphasis Type="SmallCaps">d</Emphasis>-glucopyranosyl ester and ABA-β-<Emphasis Type="SmallCaps">d</Emphasis>-glucosidase

Exogenously applied ABA-β-d-glucopyranosyl ester (ABA-GE) inhibited shoot growth of alfalfa (Medicago sativa L.), cress (Lepidium sativum L.), lettuce (Lactuca sativa L.), Digitaria sanguinalis L., timothy (Pheleum pratense L.) and ryegrass (Lolium multiflorum Lam.) seedlings at concentrations greater than 0.1 μM. The growth inhibitory activity of ABA-GE on these shoots was 26–40% of that of (+)-ABA. ABA-β-d-glucosidase activities in these seedlings were 11–31 nmol mg⁻¹ protein min⁻¹. These results suggests that exogenously applied ABA-GE may be absorbed by plant roots and hydrolyzed by ABA-β-d-glucosidase, and liberated free ABA may induce the growth inhibition in these plants. Thus, although ABA-GE had been thought to be physiologically inactive ABA conjugate, ABA-GE may have important physiological functions rather than an inactive conjugated ABA form.     

Effects of Capsaicin on Plant Growth

Rice (Oryza sativa L.) seedlings inhibited the growth of hypocotyls and roots of cress (Lepidium sativum L.) seedlings when both seedlings were grown together. Two growth inhibiting substances were found in the culture solution in which rice seedlings were hydroponically grown for 14 d. One growth inhibitor was further purified. This suggests that the rice seedlings may produce growth inhibiting substances, acting as allelochemicals to other plants, and release them from their roots into the environment.     

Organ-specific-active allelopathic substance in red pine needles

An organ-specific-growth inhibitory substance was isolated from an aqueous methanol extract of red pine needles and determined by spectral data as 1-mono(16-hydroxyhexadecanoyl)glycerol. This substance inhibited root growth of cress (Lepidium sativum L.) and barnyard grass (Echinochloa crus-galli (L.) Beauv) seedlings at concentrations greater than 0.01 and 0.03???M, respectively. The concentrations required for 50?% growth inhibition on roots of cress and barnyard grass were 0.16 and 3.4???M, respectively. However, the inhibitory activity of the substance on shoots of cress and barnyard grass was very weak. The endogenous concentration of 1-mono(16-hydroxyhexadecanoyl)glycerol in the pine needles was 4.6???mol?kg^?1. Two related compounds, 1-monohexadecanoylglycerol and 16-hydroxyhexadecanlic acid had no activity up to 1,000???M on cress roots and shoots. The effectiveness of 1-mono(16-hydroxyhexadecanoyl)glycerol on root growth inhibition and the occurrence of 1-mono(16-hydroxyhexadecanoyl)glycerol in pine needles suggest the substance may play an important role in the allelopathy of red pine. Root-specific-growth-inhibition by the substance may be one of the strategies for red pine to compete with neighboring plants for nutrients and space because root growth of competitive plants may be very important for their whole plant development.     

Abscisic acid-glu cose es ter as an allelopathy agent from cit rus fruit

Aqueousmethanol extracts of Cit rus junos, C. unshiu and C. sudachi fruit peel in hib ited the growth of the roots and hypocotyls of alfalfa (Medicago sativa L.), cress (Lepidiumsativum L.) and lettuce (Lactuca sativa L.) seedlings. Signifi cantreductions in the root and hypocotyl growth were observed as the extract concentration in creased in all bioassays. The in hibitory activity of C. junos ex tract on the growth of test plants was 3.3-to 17.9-fold and 3.6- to 20.6-fold greater than that of C. unshiu and C. sudachi extracts, respectively. Theconcent rationin C. junos was 3.5- and 4.9-fold greater than that in C. unshiu and C. sudachi, re spectively. Thus, there was a good correlation-between abscisic acid-b-D-glucopyranosylester (ABA-GE) concentrationsin C. junos, C. unshiu and C. sudachi fruit peel and theinhibito ryactivities of the irextracts. The concentration of ABA-GE in C. junos fruit peel was in creased with fruit maturityasgrowthinhibit oryactivity of C. junos fruit peel was reported to be in creased with fruit maturity, in dicating that the concentrations of ABA-GEin C. junos fruit peel was correlated withgrowthinhibit oryactivity of C. junos fruit peel in time course of fruit maturation. These findings suggest that ABA-GE may be involved in the growth inhibitory effect of C. junos, C. unshiu and C. sudachi fruit peel.     

Growth Inhibitors of Lettuce Seedlings From Bacillus cereus EJ-121

The ethyl acetate extract of the Bacillus sp. EJ-121 culture broth exhibited growth inhibitory activity on a lettuce (Lactuca sativa L.) seedlings assay. Bacillus sp. EJ-121 was identified as Bacillus cereus by the morphological characteristic and nucleotide sequence of the 16S rDNA. The bioassay-guided fractionation of the ethyl acetate extract led to the isolation of two compounds. Their structures were deduced by spectroscopic methods and determined as sodium vanillate (1) and 2-aminobenzoic acid (2). Both compounds 1 and 2 inhibited more than 90% of root length at 50 ppm (0.26 and 0.36 mM, respectively) while they had a limited effect on shoot growth at the same concentration level. Roots and shoots of lettuce seedlings showed severe deterioration at 100 ppm. In order to study the fundamental structure–activity relationship, several structurally related benzoic acid derivatives were also assayed. The existence of a polar carboxyl moiety seemed to be responsible for the stronger activity.     

Synthesis and plant growth inhibitory activity of N-trans-cinnamoyltyramine: its possible inhibition mechanisms and biosynthesis pathway

The search for potent, selective bioherbicides has been the focus of numerous studies for several decades. Developing an economically viable total chemical synthesis procedure has been the challenge for commercial-scale application of these nature-derived chemicals. An efficient and low-cost total synthesis of an allelopathic and antitumor N-trans-cinnamoyltyramine (NTCT) first reported in rice (Oryza sativa L.) was successfully achieved by one-step amidation from trans-cinnamic acid and tyramine. The synthesized NTCT inhibited root and hypocotyl growth of cress (Lepidium sativum L.) and barnyardgrass (Echinochloa crus-galli L.) at concentrations as low as 0.24?μM. The means of ED₅₀ (the effective dose required for 50% plant growth inhibition) levels of the compound on cress and barnyardgrass hypocotyl and root elongations were 0.96 and 0.73?μM, respectively. Potential mechanisms underlying NTCT growth inhibition and its biosynthesis pathway were also suggested. The developed synthesis strategy could permit production of this synthesized allelochemical at a commercial scale as a bioherbicide.     

Effect of the saprophytic fungus Fusarium oxysporum on arbuscular mycorrhizal colonization and growth of plants in greenhouse and field trials

Effects of the saprophytic fungus Fusarium oxysporum on arbuscular mycorrhizal (AM) colonization and plant dry matter were studied in greenhouse and field experiments. Host plants: maize (Zea mays L.), sorghum (Sorghum vulgare L.), lettuce (Lactuca sativa L.), tomato (Lycopersicum esculentum L.), wheat (Triticum vulgare L), lentil (Ervum lens L.) and pea (Pisum sativum L.), the AM fungi: Glomus mosseae, G. fasciculatum, G. intraradices, G. clarum, and G. deserticola and the carriers for F. oxysporum inoculum: aqueous solution, thin agar slices, and pellets of agar and alginate were tested under greenhouse conditions. Greatest plant growth and AM colonization responses in sterilized and unsterilized soils were observed with pea, Glomus deserticola and sodium alginate pellets as the carrier for F. oxysporum inoculum. Under field conditions, adding F. oxysporum increased the survival of transplanted pea, possibly through a beneficial effect on AM fungi. Application of F. oxysporum increased shoot dry matter, N and P concentrations of pea and sorghum plants, and the level of AM colonization attained by indigenous or introduced AM fungi. These parameters were similar in plants inoculated with either G. deserticola or with the indigenous AM fungi. Application of the saprophytic fungus increased the number of propagules of AM fungi in field plots in which pea was grown, but this increase was not sufficient to increase AM colonization of sorghum after the pea crop. This revised version was published online in June 2006 with corrections to the Cover Date.     

Isolation and identification of potent allelopathic substances in rattail fescue

Aqueous methanol extracts of rattail fescue (Vulpia myuros) inhibited the growth of roots and shoots of cress (Lepidium sativum), lettuce (Lactuca sativa), alfalfa (Medicago sativa), timothy (Phleum pratense), Digitaria sanguinalis and Lolium multiflorum. Increasing the extract concentration increased the inhibition, suggesting that rattail fescue may have growth inhibitory substances and possess allelopathic potential. The aqueous methanol extract of rattail fescue was purified and two main inhibitory substances were isolated and identified by spectral data as (−)-3-hydroxy-β-ionone and (+)-3-oxo-α-ionol. Both substances inhibited root and shoot growth of cress at concentrations greater than 0.3 μM. The concentrations required for 50% growth inhibition on root and shoot growth of cress, lettuce, alfalfa, timothy, D. sanguinalis and L. multiflorum were 2.7–19.7 μM for (−)-3-hydroxy-β-ionone, and 2.1–34.5 μM for (+)-3-oxo-α-ionol. The concentration of (−)-3-hydroxy-β-ionone and (+)-3-oxo-α-ionol, respectively, in rattail fescue was 7.8 and 3.7 μg g⁻¹ fresh weight. Considering the endogenous level and the inhibitory activity, (−)-3-hydroxy-β-ionone and (+)-3-oxo-α-ionol may work as allelopathic substances in rattail fescue through the growth inhibition of neighboring plant species.     

Allelopathic Potential and Mechanism of Rosebay Willowherb [<i>Chamaenerion angustifolium</i> (L.) Scop.] Demonstrated on Model Plant Lettuce

Allelopathic plants are important resources for the discovery of bioherbicides. Rosebay willowherb [Chamaenerion angustifolium (L.) Scop. syn. Epilobium angustifolium L.] widely distributes in Western Asia, Europe, and North America, and behaves as a dominant species within the community due to the production of substances that restrict growth of other plants. This study aims at investigating the allelopathic potential of rosebay willowherb by evaluation of the effects of aqueous extracts from different parts on seed germination and seedling growth in lettuce (Lactuca sativa L.), as well as measuring the accumulation of reactive oxygen species and structural analysis of root tips via scanning electron and transmission electron microscopy. It was observed that the aqueous extracts from the leaves of rosebay willowherb had the strongest inhibitory effect on the germination index, germination energy and total germination of lettuce seeds, followed by capsular fruits and flowers, and the inhibition effect of stems was the weakest. All aqueous extracts (100 mg/mL) showed a significant inhibitory effect on radicle elongation of lettuce seedlings. Additionally, after treatment with the aqueous extract of rosebay willowherb leaves, accumulation of reactive oxygen species increased in columella cells, which correlated with disruption of root tip structure.     

A Potent Phytotoxic Substance in Aglaia odorata Lour.

Aglaia odorata Lour . (Meliaceae) was found to have very strong allelopathic activity and a bioherbicide PORGANIC^? was developed from its leaf extracts. However, the phytotoxic substances causing the strong allelopathic activity of the plants have not yet been determined. Therefore, we investigated allelopathic properties and phytotoxic substances in A. odorata. Aqueous EtOH extracts of A. odorata leaves inhibited root and shoot growth of garden cress (Lepidum sativum), lettuce (Lactuca sativa), alfalfa (Medicago sativa), timothy (Phleum pratense), ryegrass (Lolium multiflorum), and Echinochloa crus‐galli with the extract concentration‐dependent manner. The extracts were then purified and a major phytotoxic substance with allelopathic activity was isolated and identified by spectral data as rocaglaol. Rocaglaol inhibited the growth of garden cress and E. crus‐galli at concentrations > 0.3 and 0.03 μm , respectively. The concentrations required for 50% inhibition ranged from 0.09 to 2.5 μm . The inhibitory activity of rocaglaol on the weed species, E. crus‐galli, was much greater than that of abscisic acid. These results suggest that rocaglaol may be a major contributor to the allelopathic effect of A. odorata and bioherbicide PORGANIC^?.     

Antioxidative responses and their relation to salt tolerance in <Emphasis Type="Italic">Echinochloa oryzicola</Emphasis> Vasing and <Emphasis Type="Italic">Setaria virdis</Emphasis> (L.) Beauv.

Two gramineous species among wild plants, Echinochloa oryzicola Vasing and Setaria viridis (L.) Beauv., and Oryza sativa L. cv. Nipponbare were subjected to salt stress. The relative growth rate (RGR), Na content, photosynthetic rate, antioxidant enzymes activity (superoxide disumutase (SOD), catalase (CAT), ascorbate peroxidase (APx) and glutathione reductase (GR)), and malondialdehyde (MDA) content in leaves after NaCl treatment were studied. RGR significantly decreased in O. sativa more than in E. oryzicola and S. viridis. Comparatively salt-tolerant S. viridis showed higher growth rate, lower Na accumulation rate in leaves, higher photosynthetic rate, and induced more SOD, CAT, APx, and GR activity and lower increase of MDA content as compared to the salt-sensitive O. sativa. At the same time, the comparatively salt-tolerant E. oryzicola also showed higher growth rate, much lower Na accumulation and no observable increase of MDA content, even though the CAT and APx activities were not induced by salinity. These results suggested that the scavenging system induced by H₂O₂-mediated oxidative damage might, at least in part, play an important role in the mechanism of salt tolerance against cell toxicity of NaCl in some gramineous plants     

Growth inhibitory effect of peel extract from Citrus junos

Extract from yuzu fruit peel (Citrus junos Sieb. ex Tanaka) strongly suppressed the germination of lettuce seeds while that from the peel of other citrus fruits such as navel orange (C. sinensis) and lemon (C. limon Burm. f.) had very little or no effect. The highest inhibitory activity was located in the peel followed by the segment but no significant activity was found in the seed extract of yuzu fruit. The effect of yuzu peel extract was tested on a variety of major crops including 38 crop species. Germination of seeds of tomato (Lycopersicon esculentum Mill.), celery (Apium graveolens L. var. dulce) and watercress (Nasturtium officinale R. Br.) was completely blocked by 27.8 mg dry peel equivalent ml^–1 of yuzu peel extract, while that of cucumber (Cucumis sativus L.) and pumpkin (Cucurbita moschata [Duch. ex Lam.] Duch. ex Poir.) seeds was not affected at this concentration, showing a broad variation in the sensitivity of crop seeds to the extract. The effectiveness of yuzu peel was also tested on some harmful weeds. The extract inhibited the elongation of both radicle and hypocotyl in summer weed quinoa (Chenopodium quinoa) grown on agar plates. Yuzu peel powder added to the soil was also effective in suppressing the growth of C. quinoa, Sonchus oleraceus L. and Digitaria ciliaris, while it had little effect on the spring weed Alopecurus aequalis Sobol. A strong growth inhibitory activity of yuzu peel was found in the aqueous phase after solvent extraction and most of the activity was recovered in the neutral fraction that passed through cation and anion exchange resins.